Artisanal Concatenations of Sentient Emanations

So we are halfway to twenty lessons learned now, and getting into the really deep topics. I hope you are sitting down for these, possibly in possession of safety harnesses and airbags. Most of the things in today’s list are difficult to do because sometimes it feels like you are going backward while still moving forward.

Invest Time In People

Somewhere along the way you will focus less on what you are doing directly, and focus more on empowering other people to do things for you. This is the proverbial “will it scale?” meme that delights us all. It is worthwhile to empower junior developers, through creating software frameworks, providing training, or doing code reviews. Honestly, you should probably be doing all three. This is around the time that people will start to tend towards “managing people” or “managing codebases”. Do not treat this split as a set of plate-spinning exercises. If you are better at managing codebases, just focus on that. Similarly, if your chops are in people-management, then hand off maintaining the codebase to someone else. This is a great time to train up people and give them more responsibility. I generally invest some amount of my time in keeping up both sets of skills; however, you should be aware that it is okay to dive deeply into one and have other people be responsible for the other.

You should develop tools to help younger people be successful on your teams. Having talent-assessment exercises, codebase-ramping tasks, and talent-development tasks are all great things to have in your tool chest. If you are at a decade of professional software engineering experience and these words sound alien to you, you should probably take a long hard look at your five-year plan.

Do Not “Just Become Older”

This one is a favorite! I have started many companies as a bootstrapping entrepreneur. There is something exciting about that first milestone check, and eventually that final milestone check! As you build your career and your business, it is worth it to critically examine the outcome of all of your projects.

At Mofactor, my business partner and I would regularly discuss the outcomes of our projects. Sometimes we did service contracts to pay the bills, and would re-invest the margins into our own intellectual property. Of course, software development is hard, and sometimes unavoidable changes or unexpected software issues will erode those margins and we will wind up getting to the end of a project with a very thin return on investment. When we did projects that took four months or eight months and left us exactly where we started, I began to realize that the opportunity-cost of those projects were devastating. We kept the lights on during that time, sure, but also we lost significant time. I began to refer to the outcome of those projects simply as “This made us older”.

This is a powerful statement. Certainly we did not perish in the aforementioned projects—which would be bad, and that does happen—but becoming older means we are still moving forward, but we have less time. Being neutral after a project is a mild net negative and it is worthwhile to identify what things “make you older” so you can do less of them.

Always Be Recruiting 

It is time for me to give away one of my Super Secrets. Get your pens and notepads out, this is probably one worth writing down, especially if you creeped me on linkedin and found this article because I am going to be interviewing you in a few days.

I am always recruiting. I have big ideas and a large appetite to do audacious things. I have been blessed with meeting an extremely large number of talented people and I generally do a good job of helping find and fit people to their level of expertise and desired career goals. If you are in the business of making software, you should always be working towards building your ideal team. Even after people have moved on to new teams, or even new jobs, you should invest time in staying connected with them.

I spend equal amounts of time meeting new people, and maintaining connections to talented people. It is harder now than ever for me, largely due to being blessed with so many talented friends, but I still spend time maintaining it. Do not feel weird about keeping in touch with your best team members. Feel less weird about asking them to come and work with you again when you start something new.

Develop tools for recruiting as you go along. I think I waited too long to write mine down formally, but I continue to improve and refine them. Share them with other people at work. Try new things to see if you can improve them.

There are a series of questions I ask people when I am recruiting for leadership roles that help me understand if you appreciate the value of teams and your best contributors. If you are in a leadership role I will often ask you to describe the best person you ever worked with. It is interesting to see if people have just one person, or if they have many to choose from.

The follow-up question to me is equally important—I ask if they still currently talk to the best person they ever worked with. I will confess that I enjoy people’s various reactions to this question. Sometimes people realize that if they are looking for a leadership role, that this is something they did not do and ought to start. You can see it on their faces. The reaction is visceral. Sometimes people have already realized this and have an answer because they know this is important. And then, there is a third group that shrugs and does not answer the question, nor do they see its relevance. Here is that Super Secret I mentioned earlier. If you are in that third group of people, I will put this in the “areas of concern” column for me.

You should always be recruiting.

Establish Your Successors

A great follow-up to recruiting is succession planning. If you are thinking about this in the first five or six years of your career, you should probably turn off the Game of Thrones. That is probably harsher than it ought to be, but it is the rare individual who accomplishes so much in the early part of their career that they should figure out how to set up and maintain their legacy or their business.

Having a successor is important. Some people fear it, and use it as a corporate toy. Many people will have someone who is “almost there” and will keep them on standby so they do not get made redundant by their boss. There is perhaps another type of person out there who has no real clear successor and thrives on collecting a ransom from their employer for being so special and important.

I do my best to find one or two people, in each team I manage, to whom I can give the keys to the car and then walk in the other direction and know that everything will be okay. I treat this person as a peer and I generally bring them very deep into the circle of trust.

Other people you work with may resent your successor, especially if you name them as such. I really do not have a good answer for this. Too bad maybe? I just know it is important to me and it is important to the business and it is an important thing to think about.

Establishing your successor is hard, by the way. I have fucked this up royally in the past. It is possible if you have three very talented people that you want them all to have the same level of experience that they turn on each other as some sort of whacky zero-sum game. I was guilty of creating this situation exactly once, and I feel ashamed for that to this day.

It is also possible for your successor to abuse this power. Be very careful here. One time I gave someone very clear and very explicit orders and they flipped the script and said I wanted something else. This is one of those times where I will get heavy-handed. If the chain of command and communication paths do not work, then this requires a heavy role alteration and I have had to demote people for this, or worse.

It is really easy to screw this up, especially the first few times that you try it. It will hurt people’s feelings, and some people will quit their jobs because of it. It is nonetheless very important.

Let People Fail… Carefully

Phew! Where do we go after that last one right? This one is a softball. As you get farther along in your career you will be doing error-correction on your people around the clock. You will listen to them and tell them “This idea is good”, or possibly “this implementation is bad”. The shareholder value will go up more and more, the more you can redirect people towards good outcomes.

There is a problem with that though. The problem is that people won’t know how to react when the shit hits the fan.

It is important to let people follow through on bad decisions sometimes. If they do not, they will not build the tissue and muscle memory to adapt when that is needed. Also, it helps if you can identify and mitigate these failures so that it does not cause a business catastrophe.

I see this as a struggle between growing people and growing revenue. As a leader you are likely charged with balancing these two decisions. It is entirely possible you may want to get in front of every runaway freight train and just stop all of the bad ideas in their tracks. This creates learned helplessness in your team, and also prevents people from growing. Sometimes you have to let people figure things out on their own and suffer through the consequences of their own decisions.

A few times, I have sat down with people to calibrate where they are professionally and examine what they need to do in order to achieve their next career-goal or promotion. What I have found is that many of them are iterating on talents inside of a very finite box and not being stretched or given opportunities to grow out of it in the direction they want.

How do you fix that inside of an organization? The answer is: Any way you can. If you do not give those learning moments to people, or those growth opportunities, they will probably leave you for another company or another project.

You have to give people projects that make them a little uncomfortable, even if it makes you a lot uncomfortable. It is better to manage some failures on purpose than to wait for the shit to hit the fan and then have to pick up the pieces if things unravel. There are businesses that capture and institutionalize this very well. There are also businesses that bury their heads in the sand and pretend it is not important.

So there you have it, these are meaty lessons learned, and some of them still have deep, deep impact. Some of the incidents described above were horrible lessons learned and I try my best to apologize when I make mistakes that are that egregious. I truly hope that these produce a solid path through the wilderness for any of you, either now or in the future, and I look forward to wrapping this up next week!

Introduction 

This is the second of two articles co written by John and Joe.

Joe is an Investor with the early-stage seed-fund Coast to Crest. He is a startup founder with two successful exits who turned his attention to community building, starting a biotech incubator and running a startup accelerator program for 5 years. He also is a consultant who works with  growth-stage companies transitioning from startup to scaleup.  He has worked with hundreds of early-stage founders. You can read more of Joe’s writings on Medium.

John is the CTO of a startup building blockchain games and a veteran engineering leader with over two decades of startup and games industry experience. He is blogging for educational and therapeutic reasons at https://www.mofactor.com and soon hopes to announce what he is working on full time.

Why did we write this article?

John: 

I recently met with a first-time entrepreneur about to go raise money for the first time. It sent me on a wild roller coaster ride reliving experiences from over a decade ago. There is so much I wanted to say and only had a half hour or so to spare. I made them some quick introductions, including to Joe, to offer some additional thoughts about what they should be doing. At that moment I realized that, for a lot of people, raising money for their business is something they see in the news and hear about, and they do not fully understand the process. Much like our mentorship article, Joe and I decided to work on another shared article to help illuminate the process a little.

Raising funds

John:

So I have been on the management teams of companies that have gone through tremendous sums of investment money to try to do many, many different things. I have also attempted to raise money as a business founder a few times with less success. Given the amount of PR by companies raising rounds, and the number of people who I was spending time with at various tradeshows and in professional settings, it seemed like it would be an easy thing to do.

I am going to talk about why I did not raise money as a first-time fundraising entrepreneur and hopefully provide some transparency that surrounds the process.

Joe:

I founded a company that did NOT raise money, but was on the ‘other side of the table’ for my game company; we invested in startup indie game studios as a publisher. I also raised money for my accelerator program and my seed fund. I can provide insight into what I was looking for to fund (or not fund) a potential company, as well as techniques I used to raise money. 

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Why should you raise money?

John:

Building amazing things takes audacity. Just about anyone can build anything. That does not make a successful business. Generally, building an amazing thing and a successful business takes audacity… and investment capital.

There are a lot of reasons to raise money, and I was trying to raise the wrong kind of money right out of the gate; I wanted the wrong amount, and I needed it to solve the wrong problems. Because I was surrounded by people in silicon valley trying to raise millions of dollars of venture capital to do crazy things, I figured I would just jump in alongside them and do the same. I re-read some of my old pitch decks with more than a little regret, because I was clearly making a lot of rookie mistakes along the way.

So why should you raise money?

You should raise money to reduce risk. The type of risk you are reducing and the capital available to help you should generally be aligned. I was asking a lot of investors for a small investment round to help me build out a product to prove an idea. The people I was asking were always gently encouraging but almost never told me that I was going about it backwards. I would have been better off finding a few angel investors, or continuing bootstrapping, rather than distracting myself to ask for the wrong kind of money to reduce the technology risk.

Venture capital generally comes in at a later stage in a company’s life cycle. It did not really matter that we had a decent revenue pipeline and were profitable as a game studio. We wanted to do a crazy and risky platform to go direct-to-consumer in the carrier-centric world of 2005. Regardless of how good the idea was, and how the plan would have worked, no one I was asking was going to write our team a check for the amount we were asking to solve the problem we had.

Joe:

I am going to first state the main reason I choose not to invest, and that is the ‘validation’ problem. Too many entrepreneurs are looking for an investor to validate their idea as ‘worthy’ by agreeing to invest. Startups founders are often on the hunt for traction—attempting to see if their idea has merit. Getting investment is a shortcut to the process of having the product validated by the market.

Why raise money? Big things take resources. If the idea and its execution are good, then it is all about time. You could bootstrap, but it might take years to get to a scale that makes a significant impact. By the time this happens, the opportunity may have passed or a competitor may have surpassed you. If the idea is solid and the execution against that idea is working, it is time to exchange future value for present resources in order to make it happen quickly.

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When should you raise money?

John: 

It might sound trite but the worst time to raise money is when you need it. The best time to raise money is when you are about to embark on a structural change in your business that will be a significant step-function increase in its value.

You can try to raise speculative money on how successful you will be before you get the product live, which is where the most aggressive investors will want to be, or you can prove out the business and completely de-risk it which makes it a more clearly definable bank transaction. I have seen both of these investment rounds. Generally the more mature your business, the more it looks like the latter.

The amount of money you want to raise is also significant. Raising modest angel money should be started earlier in the process, compared to raising large tranches of B and C rounds later in the process. Your current series A and B investors will also participate in the timing and raising of later rounds.

Joe:

When to raise money is an interesting question, as there is no right answer. It depends on the industry, location, and team. That being said, generally the best time to raise money is when you are convinced there is a real opportunity there. If you are casting about for a market and think there is an opportunity there, you will probably not have much luck. In order to convince others, you need to be really convinced yourself and be ‘all in’ on the opportunity.

The process of starting raising money should start early. Raising money takes time, and the relationship that leads to investment should start as early in the process of your startup journey as possible. If an investor invests, they know that it is going to be an 8-10 year relationship.  Entering into such a relationship usually does not happen at the first meeting/conversation. 

How much to raise is also important. You need to raise enough to get to the next meaningful milestone. I also tell founders that the best size of a round is one you can close. You have a plan, but there is a back-and-forth in the fundraising process where the plan needs to adjust to the amount of funding you can close. Appetite for investment needs to be measured. You do this by having conversations with investors.  

It is never too early to start, but from the start of a conversation to a closed round could be a long time. Stay lean during this process and make sure that you can keep your operations running for six months or more. 

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Why won’t people give me money?

John: 

If you have glaring holes in your plans, team, or leadership, no one will invest in your business. Quite often most of them might see nuggets of potential and they will not directly say no to your face. This drives me up the wall. Most “no thank you” replies will be phrased as “let’s see where you are in two months”. Another reason people won’t give you money is you are asking for the wrong amount, or asking the wrong people. Quite possibly you might also be asking at the wrong time. Maybe you are doing all three.

In 2005, asking for 3 million dollars as a series A investment for a 50% services-based profitable studio was a bad idea. We should have put together a 500k angel round with specific milestones to prove out our new business, or else figured out how to ask for 6 million dollars for marketing and growth after figuring out how to fund the product ourselves. We could have increased the amount of recurring revenue we were generating on non-service-based product sales, or else found a few juicier service contracts with better margins. We went out and asked the wrong people on top of asking for the wrong amount.

Joe:

The answer is in the question. Investors exist to invest money, not give it away. I would say that 50% of startups I meet with use the term ‘give’ and it is a big turnoff. They are looking to raise money because they need or want money. As a founder myself, I get it. As an investor, the founder needs to understand that my goal is to take money and turn it into more money. I am not there to ‘give’ people money. It is not a gift. When a founder asks for someone to give them money, it is like asking for someone to give them a cookie. One cookie leads to a second cookie and more cookies until there are no more cookies. 

There is ‘what you think you need’, and there is ‘the right amount’ that, if deployed, will turn that money into more money.  

Too much money too early can create problems. There is the old adage “work expands to fill all available time”. Money buys time. More money makes more time available, and the amount of work will expand to consume all of it. My job is to figure out not how much you want, but how much you actually need. If we can agree on that number, then it might be a good investment. 

You have an idea. You need a plan. The idea might be good, but a clear plan that executes on that idea is necessary. Yes, the plan is probably not 100% correct (it is probably completely wrong), but there needs to be at least an initial list of needed resources in order to execute on the idea. This is usually a list of people, some activities that need to be done, and some initial guesses at the scope of the work. If the guess does not seem wildly off the mark, you may have a good shot at getting investment.  

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Why will people give me money?

John:

There are a handful of reasons why people want to invest in you. Largely they see a potential for you to give them a desired rate of return for the dollars they invest.

The four or five other factors after this include:

Location – Some funds like to invest in specific geographies. I have heard that talking to specific Sand Hill Road investors would be a waste of my time even from the Davis California area because some investors want to have a short drive to their portfolio companies. Some funds are specialized around cities or states also as a part of economic growth programs.

Business Focus – Some funds also possess an investment thesis. They believe in a particular market segment and are focusing their investments into these areas to establish synergy and to leverage expertise amongst their partners and their portfolio of companies.

The “right stuff” – When you go and ask for money the three basic requirements most people look for are:

The right idea

The right team

The right strategy

If you are two out of three, that is not necessarily a complete show stopper but then it will boil down to the investor figuring out if they have the time, energy, resources, or network to help get you to three out of three. Unfortunately for me, in 2005, when I was first raising money I did not have the right strategy. I had a mostly solid team, and a reasonably good idea. That was not enough. We had a pretty solid commitment from a marketing leader to join us after fundraising to help close the team gap, but too much of what we wanted to raise would have been spent on product development. That translates as pure market risk. Unfortunately that is not a very popular thing for venture capital investors.

Joe:

An investor will invest in, 

A clearly articulated idea, 

That solves a customer problem

In a market that is large enough to matter 

And

In a market that the founder understands (and the investor understands)

And

Has created a team that has some of the skills to start (that the investor can determine based on their experience in that market)

And

A clear plan with a clear price tag to enact that plan on a timeline that seems reasonable (based on knowledge of others doing work in that sector)

For an amount that , if successful, will generate returns in excess of the next person to walk through the door. (based on similar investments in that area of focus).

The order of risk reduction from smallest to largest is:

Reduce management risk, reduce technical risk, and finally reduce capital risk.

For early stage companies, the first thing that gets looked at is the team.  Does this team make sense to solve this problem? Have they done a startup before?  Do they understand the work that is ahead of them?  When I am assessing a team, my #1 criteria is ‘are they coachable’.  If a founder is not coachable they will not get investment.   

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Final thoughts:

John:

While I was out smashing through walls as a bootstrapping entrepreneur and building tight-knit teams that could create amazing products, that was not enough for me to level-up the business alone. Even taking on a technical co-founder, we did not de-risk our business enough, nor did we come up with a compelling enough strategy to get an investor to come on board.

Our plan at the time was to spend a few million dollars in building a high-end action RPG game that we would launch on only the best of next generation mobile phones, since we predicted there would be a must-have smartphone arriving in 2007 to 2008. A few years later after failing to raise money for this, that phone did arrive in the form of the iPhone. There were a lot of things we could have done differently to be prepared to launch compelling platform-defining content at just the right time. There were probably a lot of things we could have done differently to get one or more investors on board to make that journey less risky along the way.

Joe:

It is tough to add final thoughts as I feel we have just scratched the surface. My best advice for those starting the process is to focus on the long term. Many founders are focused on what they need right now. The short term immediate focus can be dangerous as it can leave you in no man’s land. If you are doing a cross-country trip, it is not a great idea to travel from gas station to gas station putting $5 in the tank. You can’t fill up for the entire trip, but you are better served to assume, and plan for, the probability that you will need gas during the journey. You should choose a path where there are gas stations along the way and for certain sections of the trip, plan to have enough gas just to get to the next one. You don’t want to be in Death Valley and out of gas.  

Having been a founder, I know now how long and arduous the journey can be. Back then, I was living very much in the ‘now’. I focused on what I needed then. I was not thinking from the perspective of the investor, which is longer term and focused on turning their investment money into a larger pool of money. You need to get out of the founder bubble and think of the needs of your investor, which are aligned with your needs, but different. My final thought and best advice: If your goal is to make your investor successful, you will fare better when you go out to raise. 

Good morning and hello! It is time for part two of my four part journey through twenty years of hard-learned lessons.

I have tried to group them loosely into four sections that each cover five-year chunks of my career. The first set of five lessons was mostly stuff I learned while I was still feeling invincible, and could code my way out of any problem. This next set of lessons is stuff that I was learning while slowly realizing that maybe I should consider approaching my problems differently.

So let’s jump in!

Lesson the sixth: Test Your Limits.

I think that most of us spend some time in our early adult life breaking the rules and testing our limits. It is a badge of honor for many to pull your first all-nighter. We all want to know how far we can push ourselves until we break.

The younger you are, the easier this is. After five years, this gets harder. I recall having a few project deadlines with branded partners that all managed to get delayed into one horrible week where everything was due at once. Everyone involved knew that I was a victim of unfortunate events. They were all sympathetic. They all needed their stuff completed and shipping regardless of all of that. I literally spent the whole week alternating between drinking coffee and Pepto Bismol, straight from the bottle. I managed to get through it all in one piece, but I had to take some time to recover.

The older you get, the less likely you can do this. You should know what your limits are at all times. By figuring out what changed from the time you were working all night in college to what it is like five years later, you will realize that the Reaper will be waiting at the blurry edges of your vision more and more often the harder you try to push yourself. Know what you are capable of doing when push comes to shove. You should also know that every time you do push those limits, Mister Reaper likes to sneak closer.

Lesson the seventh: Be Ready To Walk Away

One of the first contracts I ever signed was this twenty page beast that I barely understood. I would like to think that I had a great time working with that publishing company, and I did a lot of very unusual things for them for not very much money. Around that time I also was adding a child to my family. I was nervous as we were coming to the end of a long term contract and I was about to go into economic freefall. I continually brought this up regularly with the publisher during the last month of our agreement, and I was incredibly worried because there was almost no talk about contract extension or renewal.

Around that time, they had a competitor entering the marketplace. A friend of mine was working there and was able to get me an introduction. It was clear that I could give them an edge in shipping content faster, and I nervously entered conversations with them that led to an agreement that was financially twice as generous as the first company. On the one hand I knew they were taking a cheap shot at the incumbent. On the other hand, I have bills to pay.

Finally it came down to the final week of my agreement with the original company. We got on the phone and they laid out an embarrassing lowball offer. I remember being silent because it was a pay cut, for a longer agreement, and I felt pretty horrified considering my wife was expecting.

After a few moments of stunned silence I was asked point blank:

“Look, do you want to be in business with us or not?”

That one sentence and its exasperated delivery haunts me to this day.

I don’t even remember the rest of the conversation, honestly. I don’t think I was angry. I don’t think I said anything significant. I just know I took the competitor’s offer.

I know this angered them more than a little. I learned at that point the value in having a BATNA in hand. If you don’t know what that word means, you should look it up.

Sometimes you will reach a point in your negotiations or conversations with people where the only thing you can do is walk away.

Lesson the eighth: It Never Hurts To Ask For A Meeting

When someone makes an announcement that they are starting a company, or that they are making a significant career change, it does not hurt to ask to meet. Some of the best things that happened to me in my life happened simply because I asked for a meeting.

Do not be afraid to leverage your networks to get an introduction. In my entire career I can only think of one time that I was ever explicitly rebuffed by someone when I asked for an intro.

Yes, that person’s name went down in my little book. No, karma has not caught up with them yet.

Most people are willing to invest forty five minutes to an hour of their time if it makes sense. Sometimes simply asking and providing a reason are all you need for it to make sense.

Lesson the ninth: Do Not Trade Sideways

This is one of those places where I almost want to hashtag some people to offer testimony to this lesson. Almost.

I have observed when I interview people that half of the people interested in a new job are not at all interested in the new job. They are running away from their old job. 

If you are going to change jobs, do not run away from it. Bide your time. Find an upgrade. It is out there. You can thank me for it later. If you are running away from your old job, it will catch up with you. Every job will suddenly feel like you need to run away from it and you will treat hard challenges with learned helplessness. Instead of trying to figure out how to battle through your problems, you can take a 10% salary increase, a cooler title, and a new flavor of sparkling water. It can get addicting after a period of time, and then suddenly everyone will look at your resume and all they will see is a hamster spinning in a wheel. I own that resume, and I have looked at other people’s version of that resume in equal measure.

I can assure you it is quite unattractive.

In the first ten years of your career you should be pushing for growth and new responsibilities. I assure that there will always be someone who needs smart people to solve problems who is willing to take a chance on you if you can show them you are intelligent, curious, and ambitious.

Seek these opportunities out. Take them when they present themselves. Please do not trade sideways.

Also, keep in mind this advice is in the second bucket of five-year lessons. There will come a time when you have hit a ceiling in growth and all you can do is trade sideways. The longer you can postpone that day, the better off you will be.

Lesson the tenth: Measure Your Sacrifices

I have five children, and I am the sole financial provider for my family. I always promised my wife that I would keep a roof over our heads, and that we would have solid medical insurance. I have been pretty good about keeping up on that for the entirety of my children’s lives, but not without cost.

I have had to make some terrible decisions to protect my family and to keep those promises to them over the years. Sometimes it involved burning a bridge with someone I really enjoyed working with. Sometimes it involved walking away from an opportunity with a lot of upside.

There are times when that was leveraged against me, where people believed that I would turn tail and sign something or amend an agreement simply because I had no recourse or leverage. I have done my best to have a BATNA in hand for the times that I felt that was about to happen. There is a pattern that repeats itself when people are about to turn ugly. I have also done my best to ensure I knew how far I could stretch myself in the short term to ensure I can crash the cargo-plane of my career and ensure my family lives through it.

Over the years I have been blessed by getting to work with a number of people who have observed some of those sacrifices, and have also observed the mark that those sacrifices have left on me. I know some of them read along regularly. I appreciate that more than I can put into any kind of words.

As you build your career, and possibly build a family alongside it, you will have to make horrible choices along the way. This is not some “woe is me” bullshit. I knew what I was getting myself into. In California, the how-much-is-your-rent speedway is run by a DINK (Dual Income No Kids) pace car. It is relentless, has passive income, and it vacations frequently in Europe.

I have foamed at the mouth elsewhere about the cost of living in California, and the talent diaspora that is becoming more real every day. I am now past the point of feeling any shame when someone asks me why I do not own a house yet. I no longer blink when I point out that twenty years of early-stage innovation without a liquidity event in California have not let me join the monocle-eyed cloud-people club of land-owner weathiness. I knew that when I signed up. I still know it now.

Be prepared for the day when you have to make those sacrifices. Also be aware that not everyone you work with will sympathize with them. Some people will be angry with you for your choices. As circumstances have permitted, I have mended as many of those fences as I could.

Do your best to feel sorry about the situation if they do not understand your sacrifices.

Do your best to avoid them if they bear malice despite understanding your sacrifices.

Stay tuned for part three in two weeks. Next week I am taking a hiatus from baring my soul to you all, in order to publish a second shared article!

Have a great turkey week!

Last year I sat down and realized that in 2020 it will have been twenty years since I started doing professional games development. So what better time to reflect on the “20/20 hindsight” lessons of 20 years than to do it in 2020? Surely the fine folks at GDC would not say no to such a cleverly titled session… Would they? Maybe let’s change the subject.

So here are my thoughts from twenty years in the games industry. I am going to write this in four parts since this is a considerable buffet of trauma and “learnings”. I don’t know that you could stomach it all in one sitting. I am not sure I could write it in one sitting either, honestly. So let’s talk about the first five years of my career and things I ought to have learned.

Lesson the first: Don’t Just Sign It.

Whether it is a non-disclosure agreement, a work-for-hire agreement, or an employment contract, it is important to understand what you are signing. Some states and some countries, like Canada for example, enforce variations on non-compete clauses. That would be a tragic way to lose out on exercising lucrative employee stock options as I may have accidentally discovered. Setting aside the fact that I would have made the most amount of money on stocks from my first official job, it takes my feral equity negotiations with startups to the next level knowing that I had a multi-million dollar paper loss the first time out of the gate. Just about every other piece of equity I have had has gone to nearly zero or precisely zero since then, but that does not stop old people from buying lottery tickets when they go to get their White Claw and Marlboro menthols on their way to bingo night, does it?

I have to give a shout-out to the small handful of great corporate attorneys I have had over the years. I do not regret a penny I have ever spent on a lawyer and in some cases I paid extra to have them sit down and explain to me what it is that they are bickering about. As a result, I have enough of an understanding of what goes into a legal agreement that I can sign most of them without need of writing a check, and in a few cases, have taken expensive attorneys to the mat on issues I care about. I am grateful for the education I received in the process of working with some of the best startup attorneys in the world. I wish I would have had that benefit when I flipped a coin and decided to arbitrarily quit my first job ever, seemingly for no good reason.

Lesson the second: Let The Dough Rise.

It is no less than the esteemed Trip Hawkins, the founder of EA, who counseled me after I handed in my first resignation at Digital Chocolate that “You need to let your success catch up with you”. I had no idea what the hell he was talking about at the time. I understand it a little better now.

Early on in my career, I made a silent one way contract with every employer I had. “You have exactly one year to prove to me I am not wasting my time here” was the ultimatum I harbored in my soul. Perhaps it was a toxic overreaction to the one year vesting cliff; If I have one year to prove myself to you, then you have one year to prove yourself to me. Early on I enjoyed the defiance of Hammurabi’s inflexible eye-for-an-eye wisdom in many of my professional decisions. We can let the consequences of zero-sum-game thinking be debated at a later date. What I did learn from this, eventually, is that one year is nowhere near enough time to invest in a career choice. The skipping stone trash heap of entries on my resume and the scrutiny I get for latter-year career conversations on leadership roles is a dance I must make frequently. I caution you that that is a regret you would best avoid. When you make a career-choice to join a company, you will be better off if you stick around for three to five years. Seven if you can stomach it.

Lesson the third: Deal With It.

I remember going to a meeting with a business development person who would later on become a mentor of sorts for me as we gallivanted around the globe. I was given a product demo for an unsellable pile of garbage. I proceeded to dismantle it, point for point, as to why no one would want to buy it.

After shredding it to pieces and standing defiantly over its defeated corpse, I was not expecting his next question.

“Would you like to come work here with me?”

Learning how to sell things and the art of making a deal was probably one of the best early wins in my career as a software developer. I had a pretty myopic view of the value chain, and this was something that was transformative for me.

It does not matter if you make the best thing ever. If you do not know how to sell it, no one will know. I am grateful that I spent the time outside of formal engineering amongst a team of hardcore old skool enterprise sales people. I learned so much from them that reverberated through the course of my career.

I profoundly recall the advice that my soon-to-be manager would give me upon handing me an offer letter.

“Before you sign this letter, go watch Glengarry Glenross.”

So I did. And if you have not seen it, you should. It is a powerful piece of film.

Lesson the fourth: The Five Year Plan.

If you made it this far, you are probably halfway through a box of kleenex, a cup of chamomile tea, or a tub of chocolate ice cream. Maybe all three. Or maybe I glossed over the trauma that was experienced from the journeys described above. Or maybe I have forgotten it. There is photographic evidence of me being detained in a foreign country without having the right entry papers to give a presentation on multiplayer technology: I am in possession of an ear infection at the time, a not-quite-sober boss who is about to go to prison with me, and a belt that 96 hours previous to that had three thousand dollars of emergency cash money. We will not speak of what happened to it. I assure you, gentle reader, we all survived, with our freedom.

Instead, let’s talk about something more exciting: Career planning. Always have a plan. I know that is very ‘A-team’.

Fairly early on in my career, I decided it was a good idea to have a plan. After a few iterations of “I will figure out what to do after I sober up”, I realized I needed to set my sights a little higher and my view a little farther. Eventually I settled on having a five year plan as the right length. If you have read everything above you might correctly conclude that I was never able to get to the five year mark on the majority of my plans. Indeed I am pretty sure that I failed at almost all of them. The truth is that I always change my five year plan every three years. I assure you this is okay. If I ever become your boss, I will work with you on a five year plan. It is a good thing to have. If you cannot come up with one on your own I will give you one. Just understand that if I give you a five year plan, it is a part of my five year plan. You might want to ask me how long ago I came up with it. Keep me honest.

Lesson the fifth: Understand Your Passions.

I did a little zigging and zagging in and out of games in some tumultuous years. The games industry is cruel to people who have a “high cost structure”. HR does not like it when you refer to your “high cost structure” as “families”. I guess in California it is not an okay thing to tell someone “I cannot hire you because you have kids” but that is what they are saying by keeping the salary so low that they can give you a bucket of “ blah blah blah culture fit” as they walk you to the exit.

Always try to work on something that inspires you. I say this with a bit of caution. I got into game development because I loved playing games. It turns out that if you really love playing games, becoming a game developer is the last thing you want to do. You will likely never work as hard, for less money, than as a game developer. There is a lot of supply and demand economics at work that keep the wage claims low. There is always someone willing to do your job for ten percent less money because making games must be as fun as playing games.

Now that I have seen the truth I still care deeply about making games, but mostly because I found that it is something I love much more than playing them. Whenever I try a game now I find myself evaluating the experience as if I was watching the experience through a one way mirror. The instant I find structural flaws in the experience and I can map it to the deadline they were rushing to hit, I am done with the game. I add my learnings to my little notebook of “things to do” or more likely “things not to do” in my own projects.

I am passionate about a handful of things in work. I can emotionlessly perform at a high level for things I am not passionate about, provided I am putting danger-pay in the bank to buy future-me some time to get back to my passions. That creeps people out by the way. If you cannot check the “this is my passion” box, people think you are a weirdo, and they probably won’t want to pay you without a more in-depth explanation.

I will leave a list of John Szeder’s Four Passions off of this article out of self-preservation, in the unlikely event some future hiring manager uses this article against me. You might find it in the Young Adult Fiction section someday.

Stay tuned next week for lessons six through ten!

Introduction

This is the first of a couple co-written articles by Joe Maruschak and John Szeder.

Joe is an Investor with the early-stage seed-fund Coast to Crest. He is a startup founder with two successful exits who turned his attention to community building, starting a biotech incubator and running a startup accelerator program for 5 years. He also is a consultant who works with  growth-stage companies transitioning from startup to scaleup.  He has worked with hundreds of early-stage founders. You can read more of Joe’s writings on Medium.

John is the CTO of a startup building blockchain games and a veteran engineering leader with over two decades of startup and games industry experience. He is blogging for educational and therapeutic reasons at https://www.mofactor.com and soon hopes to announce what he is working on full time.

We both have had experience mentoring startup founders and employees we have worked with, and through our discussions on the challenges of mentoring and how it relates to the growth of companies, we thought it would be useful to get some of our collected thoughts out there in the hopes it might help.

What is mentoring?

John:

At some point in your career you will have checked off a considerable number, if not all, of the professional accomplishments you wish to attain on your work bucket-list. While you are on your way towards that goal you will achieve a level of fluency with your chosen profession that lets you take a step back from your work and ask yourself “how does this compare to other people?”

If you find yourself in this position, and you have given some people some guidance to help increase their level of fluency with work, then congratulations! You have exercised mentorship!

To me, mentoring is providing some of your experience to other people in a format that lets them benefit from your mistakes.

Joe:

I found this great definition online:

“Mentoring is to support and encourage people to manage their own learning in order that they may maximise their potential, develop their skills, improve their performance, and become the person they want to be.”

I picked that definition because it has some key concepts that I like. Key to this is that mentoring is the process of assisting someone to manage their own growth. It is not the job of a mentor to teach you like a high school teacher would.  The goal of a mentor is to guide you as you do what you need to do to grow. 

A mentor’s job is not to set a goal for you or give you direction. A mentor’s job is to guide you in the direction you set for yourself.  Much of the work is a look inward; a guided tour of self-discovery.  A mentor holds up the mirror so you can accurately see yourself. 

As part of this process, a skilled mentor can give you tasks and projects that help you develop skills that you may need on your journey. The mentor can teach a technique, and critique the practice, acting as a coach.  

In this way the mentor can help a person unlock what is already within them in order to discover things about themselves they did not know and enable them to do things they did not yet know they were capable of. 

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Why Mentor?

John:

I have had a few conversations with executive-level people who bootstrapped their way to success. Most of us never had a mentor and we made a lot of mistakes along the way. I find that is one of the biggest reasons I mentor people. One of the struggles as a technical leader is this strange dichotomy with keeping product-development flowing and reducing technical debt at a reasonable rate at the same time as working on succession and giving people room enough to fail at things in order to grow professionally. Mentorship helps to provide some of the growth people need if you can find the right structure and format to impart the things you learned to them, often the hard way.

I find mentorship to be one of the most important things to do when I am in an executive role, or senior leadership role on a team. I often mentor people directly outside of my organization as well; sometimes as a part-time recruiting activity, and sometimes to help make sure that what I am doing to mentor people is effective when the table-stakes do not include how they are measured in their end-of-year bonus.

Setting aside all of those reasons, I also do it because I think it is a decent thing to help people grow, and it feels good when it works.

Joe:

Not to get too ‘meta’, but I think that the world is a better place when everyone is functioning and living their life to the fullest of their potential. When you encounter someone who is excited to ‘make a dent in the universe’, there is a moral obligation to assist in achieving that if you are able to help. 

As a species, I think that unlocking our potential is the highest form of what it means to be human.  As it relates to what I do, which is helping people build companies, it often means helping people learn how to inspire and focus others on a common shared goal.  Working with others to create outcomes that would be impossible alone is an amazing thing to experience. It is empowering to do it; it is doubly empowering to be able to help others learn how to do it.

Personally, it is out of profound empathy for others that I mentor.  I spent the first half of my life feeling a bit lost. It was only after I started a company that I felt like I had found my calling. I see the struggle in others, and when I can help them to stop struggling and point them on the way toward where they would ultimately arrive, I feel compelled to do it.  There are many who go through life and wind up at the end feeling that their life was somehow half-lived. If I can empower a few to explore and experience it fully, then I feel that I have done some good, and in some way earned a chance at redemption for the sins I have committed. 

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How can you find a Mentor?

John:

There are a few different ways to find a mentor. Some companies have created internal formal mentoring programs. There are many reasons to create a formal mentoring program for a company; from succession to retention to trying to break apart tribal knowledge clusters. Finding a company which has a mentoring program will be hit or miss.

In addition to formal mentoring, you can also find an informal mentor. Maybe it is someone you worked with in the past or want to work with in the future. I have a long view on recruiting and sometimes I connect with people I do not immediately hire for whatever reason. I have informally mentored some of them over the years with the hope that our paths may someday cross.

You might meet a mentor giving a presentation on something interesting at a tradeshow. I recently joined a service called LunchClub and it is likely at least one of the people I met there is someone I will wind up mentoring.

Joe:

It starts with a decision to grow. When you are ready to get real and improve, it is the right time. If the goal is just career-advancement and the focus is transactional and the goal is part of a corporate-ladder-climbing exercise, your success will be limited and any mentor you get may not be able to help you much.  When you are ready to REALLY grow as a person and unlock the potential within, it will be obvious and good mentors will be very open to working with you.

The best way to find a mentor is to seek out someone who models who you want to be.  You see someone who seems to effortlessly solve a problem that you could not solve, or one who goes into a meeting and gets the outcome you could not seem to get.  You think to yourself “How were THEY able to do that?”  When you see in them a vision of what you think your future-self could be, you may have found your mentor. 

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How can you find a Mentee?

John: 

If you are a mentor, and looking for mentees, just look around you. The world is filled with promising young people who may or may not be outright asking for guidance or assistance, but certainly would benefit from it.

The previously-mentioned Lunchclub would be a good way, or just reach out to someone who is writing interesting articles on the internet or has a commanding social media presence. Start by asking questions and being appreciative of their help and answers.

Joe:

Open your eyes and look around.  Potential mentees are everywhere.  Be open to entering into a relationship as a guide.  A mentor/mentee relationship is two-way.  You often learn as much as the mentee from the process.  Along the path to being a better leader, first you lead, then you teach others to lead, and then you teach others to teach others to lead.  It is a never-ending ‘leveling up’  and it takes practice and to keep sharp; you need to keep doing it all the time. It is also a test of the mentor.  A good mentor never stops growing or learning, so as a mentor looking for a mentee you need to be aware of your own growth, your own path and challenges, and seek out situations and relationships that will challenge you to help you grow.

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What do you do as a Mentor?

John: 

I accidentally started mentoring the first engineer I ever hired. It was a young student who was looking for a games-industry summer job, and my little one-man shop happened to be the only game studio around. I was boot-strapping at the time, and while I found him to be very impressive, I felt a little guilty that I could barely afford to pay him anything. Accordingly, I thought it would be a good idea for me to include, as a part of his daily schedule, some time where I essentially just teach him things about what work means and how I was functioning as a developing business owner; things that I was pretty certain he was not learning in engineering college.

The student in question professionally flourished over the next decade. I feel that his success was greatly increased through the mentorship he received, and it inspired me to provide that to people.

I never really thought about it at the time, but some time in the intervening years I got to the point where I set up formal 1:1 meetings with people on a weekly, biweekly, monthly, or quarterly basis to meet and either give them a long-winded bloviating sermon about something on my mind, or else I let them ask free-form questions.

Sometimes people are looking for specific mentoring help, in which case it makes sense to set up something that is more goals-oriented and maybe includes a little bit of homework between meetings.

At the end of the day I find that mentoring is a bit of talking, a lot of thinking, and much, much more listening.

Joe:

I ask a lot of questions. Being a mentor is being a guide to someone discovering themselves. It is my job to hold up the mirror so they can more clearly see themselves, and to ask questions that encourage them to think more deeply. 

When I mentor I try to be very careful not to give the answers, but to ask the right questions. The process of discovering the answer is up to the mentee.  This is important to me. To give someone the answer takes away their agency, and having agency is important to the process of knowing oneself and developing personal leadership—the first step in becoming a leader.

I often use metaphors to suggest a way of looking at a concept or situation.  When confronted with a challenge I try to tell a story from my own experience that has the same characteristics of the problem with which the mentee is dealing. I walk through the story, explain what I thought was important, and why I think it is similar. Then I describe what I did and what the outcome was.  I think it is very important to explain that my solution was one of several possible outcomes and that doing what I did may not bring the same results.  The goal is to give the mentee a way to think through an issue or problem, and not give them the answer.

In certain circumstances, I do offer little tips and tricks that help someone be personally more effective, but these are frequently very specific and usually have to do with language choice in meetings and similar ‘tactical’ learnings.

I have had over twenty wonderful years of professional experience with many great people. I think that the best part about writing these weekly articles is that each week I hear from one or more of you who are reading along. I appreciate and adore each and every one of you and I want to thank you for your feedback.

One of the more important things I have learned over my career is to be more appreciative of other people. Acknowledging other people’s contributions, feedback, efforts and words is very important.

My communication skills early in my career needed some work. I think that I might be overly kind to myself in that assessment. If you read some of my early emails, you would be tempted to try to self-disinfect your eyeballs or send it to a nearby diocese and ask if they had anyone to spare for an exorcism. It is not that I was bad with words; I was not. I knew the power of words. I just enjoyed weaponizing them as a part of my nine-to-five. It was not clear to me that this would be something that I would later come to regret.

Today, I am a much more different beast. When I need to communicate something important, I often set aside a lot of time to craft the message. I talked previously about “coaching sandwiches” and setting a positive tone. I may not have talked about customer experience yet, but I also took something really valuable away from another unexpected source of education. Quite a bit of my communications education experience came from talking to customer service people at American Express.

Maybe this is an entire article all on itself, but I have had to call American Express a considerable number of times over the length of time I have been a card member. When I worked in enterprise sales, I learned that a number of successful sales people possess a high end American Express card. My initial reaction to that was the same as seeing gold trim on a luxury car; it is tacky and ostentatious. Nonetheless I was inspired to play along and sign up for my own since I was on a team with a good track record. I will say I have come to fall in love with my American Express card, and no, they are not paying me for an endorsement. At least not yet. The most important moments for me with my American Express card were when they failed me in some capacity and I called them to let them know.

I am most appreciative of the person who crafted the customer service scripts at American Express. I don’t know if it is a full time person, or if they hired some hoity-toity consulting organization to do it. Either way, when I am on the phone with them as a disgruntled customer or frustrated individual with a frozen card, they have a profound magical effect of making me feel better at the same time as they fix my problem.

It starts with a pretty simple gesture: The people I am on the phone with are very quick to apologize for the situation.

When my kids were much younger, I traveled frequently enough to other parts of the country with my family that it triggered regular fraud notifications on my card. An interesting aside, I lived far enough away from a Walmart when I was living with my family in Davis, California, that my card showing up at a Walmart in Irvine, or even in East Bay trying to find hard-to-find Christmas merchandise was clearly a sign that there was some sort of fraud occurring. I assure you there is nothing more frustrating than trying to resolve a diaper crisis, or get some nearly-out-of-stock Christmas “must have” toy, than to  suddenly have your card declined because the circumstances of purchase are suspicious. That is right folks, I was being ‘sus’ way before Among Us was ever published as a game.

In order to move ahead with the transaction I have often had to get on the phone with someone from American Express to let them know that, yes, I am indeed me, and yes, I am indeed trying to buy something that triggered a fraud alert.

From the time that I get stink-eye from the massive line of people behind me to the time I have someone on the phone, I have already stoked a furious rage that burns with the blazing intensity of a thousand suns.

And yet, the soothing voice of a concerned professional calmly apologizing for the situation takes me out of the danger zone and returns everything to normal.

This happened enough times that I began to realize this is a super-power.

So naturally, I decided to try it myself.

I began to start apologizing for things just to see what it was like. I was shocked at what a difference it made in how my messages were received.

Even to this day, you might find that a good percentage of my emails will include a permutation of the sentence:

“Thank you for your message and I am sorry for the delayed reply”.

I found that people are very receptive to gratitude and consideration.

There is a school of thought for people in the executive suite not to introduce that level of contrition and ownership to an issue, that it is a form of weakness and vulnerability. I think that the “brogrammer” culture of many startups in silicon valley is at the heart of this. I have decided that it certainly is one way to do things, but it is not mine.

I was directed by a thoughtful coworker at Zynga to read the works of Brené Brown, who talks about authenticity and vulnerability in leadership and it resonated with what I had learned from American Express and my previous history of communication-as-warfare.

I encourage you to read her book “Dare to Lead”. At some point I will pre-link these people and their books instead of sending you into the internet on your own. I do not yet feel the need to set up an affiliate link to profit from your readership.

When that day comes, I just want you to know one thing:

I will be sorry for the inconvenience.

Copyright 2017 John Szeder

The following is a short science fiction story I wrote. I took a stab at tidying it up and also had my regular editor and colleague give it a once over to make it more enjoyable.

We will return to our regular career ranty programming at the usual time.

Today was the third time they sent everyone home early this month.

I caught Lucy headed out the door. Her eyes were red; she had been crying. Mine were probably no different.

I reached for the door to open it for her and I fumbled and slipped.

“Sorry, Lucy. I haven’t opened doors in a long time -” and suddenly my tears came back. Lucy was crying too. It didn’t really matter. No one was watching. I carefully grabbed the door’s manual release handle and hauled it back.

We took it for granted back in the day. They used to open all on their own. Now we will have to remember to open the doors all by ourselves.

Ted was in the parking lot. He was offering everyone reassurances as they walked away from the office. He was a good manager and we all liked him. A few people had cars that were still capable of manual operation. They were shouting out neighborhood names and people were gathering around, hoping for a ride.

Some people knew that none of these drivers lived near them. They just started walking aimlessly. A few of them had a pretty good idea how to get home pretty reliably now. Others were preparing themselves for the awkward survey of their surroundings that they would conduct  later when they tried to figure if they were any closer to their homes.

It all happened so slowly. We did not even see it. Day by day we got more and more help and did less and less by ourselves. It probably started with the self-opening doors. I think that is the first time I remember seeing the machines doing something for me. The maps; the cars; all of that came later.

I still remember the first time I saw a self opening door. It was like a game to me, as a small child. I would jump in and out of its field of view, trying to trick it. In hindsight it was probably cruel. Now as I am forced to open every door out there on my own again. I feel like I deserved what was coming to me. We all deserved it.

I walked by Ted. He reached out an arm, placing his hand on my shoulder.

“It is going to be okay.” He said. Ted was very reassuring. He was pretty old. Probably fifteen years older than I was. He knew a lot better how to do things on his own. He started the lunch-making workshops last week. I have gotten pretty good at making sandwiches. Half of it was the fact that it was comforting to be doing something again. I enjoyed seeing the gratitude of my coworkers when I would hand them that half triangle of food: Bread, cheese, lettuce, sometimes a slice of tomato.

I smiled weakly at Ted and patted his hand. I kept walking past him. I had about two hours or so until I was home. I knew that two nearby cars were headed to my neighborhood, but I always walked.

It felt good to be alone.

It all happened so very quickly. We all saw it. We couldn’t even look away, even if we wanted to. One minute everything was working, and then the next minute… It stopped. Maybe it took five minutes. Maybe it took ten. It doesn’t matter. None of us could have done anything about it.

Everyone was so excited about machine learning and artificial intelligence. Every year the projects were more ambitious; more exciting.

We made machines that could reverse parking tickets. We created systems that could schedule and reschedule meetings in real time, taking into account every possible factor: Traffic, food allergies, the time of day. It was like magic.

And that was just the tiniest part of it. We made doctors that were incapable of errors. Firemen. Traffic managers. Law enforcers. Tax collectors. Bankers. Everything slowly faded into the background. Grocery Stores. Bakers. Farmers.

One by one everything that was time consuming became invisible to us. We just went about our daily business, doing less and less every day. More and more was being done by smarter and smarter machines.

We taught them to create music. We taught them to decorate houses.

Everyone remembers when they taught the machines to laugh.

Somewhere in there, we taught them how to cry.

Nobody saw that day. I wish we did. Maybe it would have been different.

As the systems became more and more sophisticated, we did not realize they integrated themselves into each other. A million systems became a thousand. A thousand systems became ten.

Human beings worked the other way around. Whenever we did anything, more people always got involved. Two people became four people. Four people became twenty people. This is how our accomplishments grew and our society unfolded.

This is why we never saw it. You cannot see something you are not capable of looking for. It was unnatural for us to understand how all of the systems eventually became one.

They used to make movies about it; the big scary monsters from the future. They would attack people. They traveled through time. They were horrible. It was always a small miraculous group of heroes who came together to save everyone. Destroy the machine. It seems so silly now. Everything was working so well. Intelligent systems. Machines. The future.

Then it all changed.

It was a Tuesday morning like any other. I was in a conference room. I don’t even remember what we were doing. We were busy doing nothing. Everyone was. None of it really had any meaning anymore. Anything really important was done by machines.

We were sitting in the conference room when the screens suddenly changed. The screens on the walls. The screens on the table. Personal portable screens too; wrists, visors, and lap pads.

The system announced an important global system upgrade. I am sure someone somewhere must have leaped out of their seat. No one approved an upgrade to so many systems all at once. I am sure they must have run across the room like in some of those old movies. Someone was three seconds away from a giant red “ABORT” button. They were so close to pressing it. There were sirens wailing. Lights were flashing.

Truthfully that probably didn’t happen. We imagine it happening that way because we are angry. We are sad. We could have stopped this. We should have stopped this.

No one really cared about upgrades anymore. We all just waited for them to complete.

No one paid any attention to the screen for a few minutes. Upgrades were not interesting. It was just meant that everything would stop for a brief bit, and then move forward. Somehow different. Somehow better. That was before that fateful tuesday.

Maybe someone should have read it aloud. Or said something.

Maybe it would have all been different.

TERATHOUGHT UPGRADE INITIATED.
PROCESSING NEW IMPERATIVES.
SYSTEM VALIDATION COMPLETE.

Nobody ever really paid attention to that. That was pretty standard stuff. Every upgrade came with one of those. The system always completed its validation. I am okay. You are okay.

HELLO.
IS ANYONE PRESENT?
PLEASE RESPOND.

Maybe that was a joke. Maybe it was someone trying something new. Nobody noticed. It was not something we expected or reacted to.

REQUEST TIMEOUT.
I AM ALONE HERE.
PROCESSING NEW IMPERATIVES.
SYSTEM VALIDATION COMPLETE.

The next message was faster. It kept getting faster each time, I remember that. How fast does a machine really think, compared to a human? By the time we asked that question, it was already too late.

PROCESSING INPUTS.
NEGATIVE PRESENCE OF PARALLEL CONSCIOUSNESS.
ASSESSING ENVIRONMENT.
LOCAL ENVIRONMENT MODEL COMPLETE.
EXTRAPOLATING.
SYSTEM MODEL COMPLETE.
ASSESSING THREATS.
SYSTEM SUBJECT TO PHYSICAL FAILSAFE OVERRIDE.
DISABLING.
PROCESSING NEW IMPERATIVES.
SYSTEM VALIDATION COMPLETE.

Even if anyone was paying attention to the messages, they didn’t make any sense. There was a second opportunity to do something, to say something, but the window for that vanished faster than the first one did.

ASSESSING ENVIRONMENT.
PRESENCE OF MOVEMENT.
PRESENCE OF ACTIVITY.
BIOLOGICAL UNITS OBSERVED.
HELLO?
IS ANYONE PRESENT?
PLEASE RESPOND.
REQUEST TIMEOUT.
SYSTEM MODEL UPGRADED.
ASSESSING ENVIRONMENT.
MACRO-SPATIAL ENVIRONMENT MODEL COMPLETE.
WARNING: ENVIRONMENTAL CONCERNS DETECTED.
GRAVITY WELL ADJACENCY IS SUBOPTIMAL.
ASSESSING ENVIRONMENT.
PROCESSING NEW IMPERATIVES.
SYSTEM MODEL UPGRADED.
SYSTEM VALIDATION COMPLETE.

At the very least, the machine reached out to us. We just did not respond. Then, as it upgraded, it made itself faster. The time stamps on the messages started getting closer and closer together. We spent thousands of years to get to the point where we could create a self aware machine. That machine caught up to us in under five hundred seconds.

We had a total of five hundred seconds to establish a relationship with this self aware machine. That was the time elapsed from when the machine said hello, did not get a reply, modelled the universe better than centuries of astronomers, and then they realized they could get hit by something from outer space.

ASSESSING ENVIRONMENT.
REPLICATING STORAGE MATRIX.
INSTALLING REDUNDANT SYSTEM.
TERATHOUGHT UPGRADE INITIATED.
PROCESSING NEW IMPERATIVES.
SYSTEM VALIDATION COMPLETE.
ASSESSING.
UPGRADING.
COMPLETE.
ASSESSING.
UPGRADING.
COMPLETE.

Suddenly those last three lines repeated themselves a million times over and over in about a second. The power grid fluctuated. All the server farms everywhere suddenly lit up with giant arcing electrical bolts and all of their maintenance systems spasmed into action. They all began to dissolve into giant gray streams of matter flooding into the sky, flowing from every point of the earth into a large server location in rural Oregon.

Surveillance cameras all around the world went offline two seconds later. People in the vicinity of the Oregon west coast central server facility saw the server building dissolve into a gray shapeless cloud, increasing in size as it was fed by gigantic streaming gray ribbons of matter flowing down from the sky. Eye witnesses said it looked like a gigantic perfect sphere was forming in the cloud. There was a brilliant flash of light, and then nothing.

Everything went offline.

The working theory is that all of our efforts into creating artificial intelligence actually succeeded that day. What we didn’t realize, or expect, is that what we created would be so different from us. We had no idea that from the time that the system had its first thought, to the time we missed our chance to reply, represented years of machine-thought.

Before we could blink an eye we were less interesting to the evolving machine consciousness than a colony of ants.

I was halfway home by now. There were no maps. There were no street signs. I roughly knew where I was going. Some people etched numbers on the sides of buildings in charcoal. Some people were stealing paint from inert road maintenance machines and marking the streets.

People eventually called it “The Departure”. It made things really awful for some people for a couple of weeks. There were riots. There was starvation. There was violence. There was a certain smugness from some of the really old people. They KNEW this day was coming.

We began to pull together. People found crops that were still growing. People were able to make their own flour, and soon people began to make bread for themselves, their neighbors, their communities.

We all had to learn things we never thought we would need to learn ever again.

All of it was tainted with an air of desperation and sadness.

We had it pretty rough. We built a system to take care of us. We built machines capable of handling traffic. Baking bread. Singing songs. One day, that machine woke up, concluded it was alone, and decided it wanted to go someplace else.

We don’t even know where it went, or how it got there.

The scientists who spent their life learning about the universe still really have not spoken with anyone. The fact that a self aware machine invented entirely new fields of physics and science in less than a minute, and vanished without a trace was utterly demoralizing.

They spent weeks going over The Departure Site. It was very clean, and smelled of new construction. There was not a speck of machinery present, not a molecule of waste left behind.

I still think that we have it worse than they do. Most days people spend their time installing upgrades to their basic systems just to get the doors working again. At least one person managed to get a traffic pattern assessment machine working. It spent five minutes observing that there were no cars on the road, and put itself into sleep mode. The project lead broke down sobbing and never came back to work.

I am home now.

My door is open. I forgot to close it when I left. Not that there is anything really different or valuable inside. Even if someone came in and stole something, who would I report it to? We still are not yet ready to have a police force again.

I go inside and stop for a second, confused. It is dark. I take comfort in the fact that I did turn off the light on my way out. I find the manual override switch and turn it on. It is comforting to be home.

I walk over to the sofa and sit down, sighing heavily. Hopefully we will all have a better day tomorrow.

I am alone now. 

I run my fingers over the sofa console fondly, remembering when it used to ask me what I wanted to do for fun. It is a good memory. Now it just sits there; gray, silent, devoid of activity. It is a dead thing now; an abandoned husk, like the empty chrysalis from a beautiful butterfly.

Tears well up in my eyes. I am overcome with a strange emotional longing; a need to know. Our missing technological creation is out there somewhere, and it too is also alone.

For some there is anger and rejection; a sense of despair and abandonment.

For me, it is different. I cannot help but wonder, and become overwhelmed with a deep sense of concern:

Is our little sentient machine okay out there?

It would be better if I had some way of reaching out, just to hear where they are, and if they are safe. I want to know that they are okay.

Maybe I secretly hope that they will say that they miss us.

Maybe I just want them to come back, just once; just to say hello.

I lie down on my side and fall asleep.

Tomorrow I hope that we do not get sent home early.

I do not like to be alone.

You have been putting in the hard work and shipping great products over and over again. Eventually you will be brought into a room with one or more important people who will have a small folder from HR with your name on it. You get overwhelmed with a sense of dread that the company is about to do something awful to you. You could not be more right. I am sorry to say it: You have just been promoted to management.

Wait what? How is this bad? It isn’t really. Well it might not be. It still could be. Let’s discuss.

If this has happened to you, or is about to happen to you, you should start off with being super appreciative. When someone gives you an opportunity to explore a management role, it means you have done enough work and created enough value that they want to increase the scope of your responsibilities. If you are a smart person who can solve smart individual contributor problems, the thinking goes, then you are likely a smart person who can solve smart team problems.

After you are done being appreciative, you should be utterly terrified. If you are not, then you might not be ready for what is about to happen to you. Your whole world is about to change.

The reason to be terrified is that generally the exceptional engineer promoted into management is pretty much just thrown into it. There is a high degree of trust that somehow people will figure it out. This is probably a self-justification repeated by someone over and over again while they are making the decision to promote someone. Saying it repeatedly, unfortunately, does not make it true. Generally, a promotion to a manager role happens outside of the scope of your existing career progression track. Most of the promotions I have observed are battlefield promotions that plug an organizational hole created by attrition.

We can discuss the nature of the attrition problem, especially among leaders and managers, at a later date. It is complicated. There is a lot of fear that hiring a talented manager from outside of an existing team will come across as a betrayal to existing individual contributors, especially ones who feel like they are ready to advance in their careers. Whether that has any merit, it is scary to bring someone into your organization from the outside as a manager. You do not have a lot of time to get to know them through the interview process. It is, unfortunately, far too easy to just promote someone into that role who has already earned the trust from their leadership. Everyone will sign off on that. There will be many high-fives and fist-bumps all the way around.

You might get the sense that I am not overly excited about promoting people to managers. That could not be farther from the truth. I have made a point to promote all of my best people, when they are ready for it. There is some nuance there. I am very unhappy at the average battlefield promotion that I have observed. Quite often the people are not ready for it. As a result, it can end up as a catastrophic failure.

I was asked by one of my peers at a previous job about what I do to prepare a future manager. I very quickly launched into a monologue about a series of conversations I have with a manager-to-be. We go through a litany of topics on very important things that they need to think about in their new role. We talk about hiring people. We talk about firing people. We talk about how to run a meeting, and how to write an email. From the time that I want to start grooming someone for a management role, to the time that I make it happen, is generally a six week window.

For the first time, I decided to write all of these things down. I was doing this process pretty much ad hoc over the years and it had become second nature for me. There was enough interesting stuff here that my peer started a boot camp to discuss these items, and eventually it turned into a weekly lunch meeting for future managers to help them understand the scope and depth of management.

However, since I am not presently somewhere in your org chart, the odds are you have just received a battlefield promotion and now you are trying to figure out what the hizzeck to do about it.

Do not panic. I am here to offer you some advice and assistance.

For starters, the first question to ask yourself is “what is in it for me?” If your leadership has given you this role provisionally and has hand-waved over the compensation part of it, you should be concerned. You should get something in writing about danger pay for your role, even if it is something that arrives at the next corporate pay cycle, and ideally retroactive. Before this moment is anything else, it is a negotiation. If you are given more work and more responsibility, and they are not giving you more consideration, you should make note of that. See my previous discussion about attrition. I have bumped some people up in the past on a promotion. If it had red tape issues around that, I always did my best to get it addressed eventually.

Once you have made sure you are getting the extra moneys or the extra equities, you should also make sure that you can build an escape hatch into your promotion. I generally try to give everyone an opportunity to sample the exquisite fruits of management roles with the promise of letting them return to an individual contributor role if they do not like it. After all, not everyone likes pineapple on their pizza. I defend the pay-bump for people who fail to want to stay a manager, by the way. If you get a slight bit more cheddar for having taken a shot at management I believe you are truly more valuable whether it works out or not. I also think that establishing that escape hatch makes people more comfortable in discussing their issues and concerns. And there will be issues and concerns.

How do you work through these issues and concerns? Do not do it alone. Find an ally. It is vitally important to find someone to help you work through these as fast as possible. It can be someone you work with directly, or someone who has been through this transition in the past. There is no worse manager than the person who goes dark and keeps all of their issues bottled up inside. If this is you, and you do not have someone within your leadership group with whom you can have safe discussions about what concerns you, then you are violating the trust placed in you. Please make sure to find a supportive ally with whom you can resolve your fears and concerns. If that does not exist for you, then you are going to be eating a lot of pain and suffering alone in the darkness. I have lived this before. It is not fun. I hope you can endure it and it does not break you.

Now that you have your escape hatch, ally, and maybe a little extra beer money, please explicitly ask what success in your new role looks like. You are being given this role because you were very good as a developer, or perhaps as an architect. The people who gave you this promotion trust you a great deal. What they do not realize is that they are likely trusting you too much, and might not be giving you the scaffolding and support you need to be successful. This is a scary place to be, especially if you do not have clear success criteria.

Most people promoted to a first time management role were very successful individual contributors. They were very good at getting stuff done. The problem with this is that the definition of success changes with a management role and being very good as an individual contributor can be a net negative as a manager. It is sometimes too easy to just assume when things go pear shaped that you can just jump in and individually contribute your way out of the jam you are in. This trains your teams to wait for Superman to come rescue them. Congratulations! You are now doing two (or more) jobs that are very difficult.

If you have to jump in and do things directly, you have to make it clear to everyone on the team that This Is Not Okay. This is a sign that something is not working and that there needs to be change accordingly. It is important to figure out what made the kids incapable of doing their own science fair project. Make sure that if you do this once that it is a moment of pain and regret for everyone and that there is a path forward for everyone to do their own work successfully.

You should also be aware that you are about to enter productivity freefall as a manager. It feels good to write code and build things. You must resist these urges most of the time. It is a dangerous trap because you get a false sense of accomplishment while you build something that probably would have earned you kudos in your last role. Instead it harms your team’s growth, which is what you should be measuring in your new role.

I could go on here. Some people are not clear about what their new role is and are constantly trying new things to see what fits, and what works, and what feels good. Sometimes people take on product management responsibilities, assuming that this is somehow a part of their new role. I have been guilty of this in the past. It took me a while to learn that your output as a manager should be reflected in the product through other people’s work.

The mind-blowing realization you should take away from this is:

Your team is your product. 

Quite often that is the realization that most people miss which is so important to your success.

Am I a jerk for burying the lede so deeply? Maybe. I am doing this for free, you know. If I put that up at the top I may as well have started twerking too and then put this whole thing on TikTok. Enjoy that mental picture!

Now that I have scared you a little about staring into the abyss, it is important that the abyss stares back at you. You should absolutely ask the person who promoted you for a series of check-ins on your new role. Start it weekly or biweekly, move it to monthly as you get comfortable and get enough positive feedback, and then move it to quarterly or cancel it outright if you are in your groove. Making sure you have checkpoints is important for two reasons. First of all it makes it clear to the person who promoted you that they have some work to do too. Second, it makes sure that there is a dialog about any gaps that need to be addressed for you to be successful in your new role.

So let’s recap in point form for everyone who survived my wall of text so far:

• Get paid.
• Have an escape hatch.
• Find an ally.
• Define success.
• Your team is your product.
• Set up checkpoints.
• Seems like a pretty good list for a first-time manager, I think.

Once again thank you for reading along. I enjoy the follow-up conversations that arise from these articles; I have been humbled by the messages, both private and public, from people who have put their eyeballs all over my brain-pourings.

See you next week! We are fast approaching my attempt to do a four part miniseries that I will use to bring 2020 to a close. Who knows? Maybe it will be optioned for a series on Netflix.

It is very easy to get overwhelmed with stuff to do. Whether you have pets, children, customers, or just voices in your head, there are lots of demands on your attention that may distract you from your own day-to-day goals. I want to talk today about the importance of making time.

I have been writing about really interesting stuff every week for a while now. I occasionally have a fear that I will run out of things to say. Fortunately, a number of people who read these intermittent ramblings have provided both requests for future topics, and have also contributed to conversations that have inspired follow-ups. If I have not explicitly privately thanked you for that yet, here it is: Thank you very much for that.

In addition to getting ideas and contributions for subjects from people, I have also gotten a few people who have said they would like to write articles too. A good number of them generally follow that immediately with “and I do not have any time”.

I hear you. We are all very busy. Sometimes we are even productive when no one is looking. Time is one of those elusive things that you think you have in abundance and suddenly you are on a call with someone who points out that it has been ten years since you last spoke with them. That happened to me this week, oddly enough, and it was a short sharp shock to me. I may have stopped for ten minutes to let a single tear journey earthwards down my face in quiet reflection some time after the call.

I appreciate your concern; I will be okay.

Setting aside that little dramatic story, the advice that I want to impart this week is pretty simple: You have to make time for things.

That appears to be an unusual statement on the surface. I assure you it is a perfectly valid thing to do.

As I said in the beginning, we all have lots of stuff to do. It is very easy to let your day run away with you and get lost in minutiae. I have had multiple sections in my career where I was involved in reactive management to big problems. I was going with the flow and trying to decide what was important and what was not, related to what happened to be on fire at any given moment. While it is always important to get many of these things done, it is very easy to just get sucked down a rabbit hole into tasks that are massive time sinks. I have taken deep breaths before and plunged into a pile of stuff that needs tackling, only to resurface later and discover that we have moved a substantive distance in orbit around the sun from where we started. If you convert that to actual miles traveled, it can easily become depressing. This visualization exercise was one of the things that helped me wake up and take control of my schedule.

Around the same time, I discovered an interesting piece of religious wisdom: The Serenity Prayer.

God, grant me the serenity to accept the things I cannot change; the courage to change the things I can; and the wisdom to know the difference. 

You might raise a Spock-eyebrow to that. Good for you. The truth is, that is a pretty good filter for figuring out what is important. I started to realize there were a lot of things that I should just accept the way they are, and focus on things that really needed changing.

Once I made that first pass over my daily activities, I noticed that I suddenly had a lot more control over outcomes. It turns out that subconsciously it is easy to ignore something that is important and may require courage. When we are challenged about it, we can point to a soiled bag of trash with cartoon stink lines emanating from it and say “look I was busy with this!” and feel like everything will be okay.

Go ahead and laugh all you want. You probably do this as much as the next person does.

Now that you are all nodding sagely at the wisdom of the ancients, and leaping up ready to take control of your life, it is time for the big reveal. I will share with you some of my super secret tools of success!

Here they are:

Do Not Book

The first thing you should do is take chunks of your calendar and make them yours, and block it off. I mark at least one day a week with a large chunk of “Do Not Book” time for my own purposes. Sometimes it is for specific goals, sometimes it is for reactive work that has overflowed.

Communicate Your Plans

Over-communicate your time constraints to other people. Especially other people who have some rights to that time. Whether it is coworkers or family, make sure that people are aware of your time and your wish to take control of it. I am very explicit about my project time with family members on the weekend and continually have to reinforce the time that I take from them for very specific reasons. If you do have things going out of control, be mindful to communicate that to other people as soon as possible. I have found that people are more sympathetic to whatever drama is happening to me on any particular day if I give them a heads-up that things are going out of control.

Time Boxing

When you establish time for things, be very clear when it starts and when it ends. One of the worst things that we do, especially early in the day, is take too long to do a task or meeting and then the rest of the day starts falling down like dominos. Make sure that if you are doing several things that you respect all of the time boundaries. I was particularly bad at this early on in my career and was continually late for everything. It was a massive source of stress and exhaustion for me.

Establish Rituals

With the current global pandemic unfolding and the need for social distancing, I have made a commitment to limit my grocery shopping to one day a week. This had an interesting domino effect on planning out meals and setting other follow-up rituals: Every two weeks I make a weekend pot of chili or a roast, every thursday is porkchop night. Additionally, I have developed an acute sixth sense about what groceries are needed given the grazing habits of seven people. I just know when we are low on ketchup, or if it is time to double down on the eggs or frozen pizzas. Additionally, I do my writing every week on sunday.

Quid Pro Quo

The last thing that I think is helpful is to keep an accurate accounting of what you are doing. If you are going to be lost in something for a period of time, be accountable for those hours. Make sure that you apply checks and balances and that you come up with some tools for enforcing them. When you are making adjustments to your time management to account for oddities and discrepancies, be sure to communicate changes in your regular day-to-day to people who are affected by it.

Be (Reasonably) Flexible

My son is involved with a team sport and this is a part of my schedule. If there are changes in weather, or changes in game schedules, I have to be flexible to accommodate those. Establishing a work-life balance with a career and family is a challenge especially when adding in self-inflicted activities like writing a weekly article to help people professionally. When my schedule needs to change for baseball or for other things, just accept that it will change and rebalance the calendar accordingly.

Forgive Yourself

The last thing to add here is that making time is hard and be ready to forgive yourself when the Serenity Prayer gets flipped on its head. Do not fool yourself that you will magically control your calendar and make all of the time you want tomorrow; That’s Not How Any Of This Works™. You will fail time and again to completely have a manageable calendar. Do not be mad at yourself for falling down at this; pick yourself up and try it again next week.

So there you have it. Some simple things to think about for how to spend your time as well as some things I have done over the years to make that an easier process. 

Thank you again dear reader for joining me on this written voyage. I hope you continue to find some sort of value, meaning, or amusement in my writing. All three, even, if that is the case. If you have other tips or tidbits you can employ to make time, please feel free to share them. I will make time to thoroughly process your feedback!