Greetings, friends. (LXXI)

Greetings, friends. This past week, I went to San Francisco primarily to attend a day-long manager training at my employer’s office. This first session of this nine-week management training course consisted of an eight-hour kickoff workshop, during which the dozen or so of us management trainees were asked to put away our laptops and phones for the day.

If there is one thing I learned from having sat in this management training for the better part of eight hours, it is that I am not cut out for classroom learning.

Having recently re-read my grade school report cards, I realize this is not a surprise. In fact I have always been this way. Classroom learning moves too slow to hold my attention. I haven’t been subjected to this kind of mandatory learning in years. Even at professional conferences, I and about 85% of the other attendees all have phones out or laptops open. I watch most YouTube videos and listen to podcasts at 1.5x speed or faster, unless I am doing something else at the same time.

It wasn’t all bad. The day was peppered with prompted one-on-one and small group discussions which served to anchor the material in practical experience, and offered the chance to get to know some of my colleagues a little better. I just feel like the whole workshop could’ve been about two hours, and I’d have gotten the same amount of value out of it. All of my colleagues seemed engaged so I did my best to hide my considerable discomfort and look like I was paying attention.

The kicker was the final exercise: After about eight hours crammed in a fluorescent-lit conference room with poor ventilation and no other stimulation, we were asked to take a piece of easel paper, stick it on the wall, and draw our “professional timeline” using magic markers in whatever format we saw fit, noting the highs and lows of our careers with as much candor as we could muster. We were shown an example of a classic horizontal timeline with vertical ticks. We were further asked to mention two hopes for our career, as well as two fears.

I raised my hand. “What is the purpose of this exercise?”

“It’s so we can get to know each other better.”

I panicked and froze. I had already been in cognitive agony for most of the day. I was exhausted and my blood sugar was crashing. I didn’t want to get to know anyone better; I just wanted out of there. I felt depressed and cynical and cranky and couldn’t think of anything nice to say about my career. I tried drawing a horizontal line on my easel paper in a loud pink. Nothing came to me. I thought about fleeing again. Finally I took a black pen and wrote four short bullet points that took up the entire paper.

Most people played it straight and drew an actual horizontal line with tick marks. The design director drew a vertical line. The data scientist drew a curving path. One other manager drew a map.

Having children was the most commonly referenced high-water-mark life event. The death of beloved pets was the most commonly referenced low point. One respondent, bless him, mentioned a divorce. “Continuing to grow in my career” was the most commonly mentioned professional goal. I couldn’t tell whether my colleagues were serious or just playing it straight to be safe.

Whether deliberately or by chance, I was chosen to present last. Here’s what I had written:

1. don’t kid yourself about product-market fit

2. never forget the iron triangle

3. first, do no harm

4. you don’t have to self-actualize at work

Here’s what I had to say:

I know we have been asked to be vulnerable, but what I have learned is that, in a professional setting, that means “be vulnerable, but not too.” I hope I don’t overstep my bounds here, but it is late and I am tired and hungry, so I hope you will forgive me if I do.

I got into information technology as a passionate Open Source developer. I firmly believed that the economics of software — the way in which it could be replicated at zero cost — meant that a few volunteers could have an outsized impact. I care the same as you do about my actions having a positive impact in the world.

I think the most impactful thing I have ever done was to help launch a Free Software project called OpenLayers, a client-side cartographic library which has been used by probably millions of people, and is still under active development. That was about fifteen years ago.

The problem I found was that volunteering on Free Software and working for public institutions like the New York Public Library and UNICEF was rewarding… but I was never really able to afford the lifestyle I wanted to live in places like New York and San Francisco, or set myself up for long-term financial stability.

Of the five startups I’ve worked for since, four of them are defunct, or might as well be, as far as the common stock value is concerned. I think that the specific companies I worked for, or what I did there, matter less than what I learned in the process.

Ten years ago, I wrote a blog post about what I thought I knew about winning the dot-com lottery. Note that I have never had a “successful exit”… but two friends took me aside years later, and told me that they had followed my recommendations to the letter, and gotten modestly wealthy doing so. So that was nice.

Nevertheless, here are four more things I have learned since then:

Every single one of the four startups I have worked at previously was engaged in some kind of fantasy about the existence and size of the market for the product they thought they were building.

I cannot emphasize enough how easy it is to fall into groupthink and other fallacies around this. It is so common as to be a trope and yet people continue to engage in wild, get-rich-quick fantasy. Blockchain, anyone?

Thankfully, my current employer actually has an actual product that actual customers are actually paying for. The executive leadership seems to understand the evolving market for Human Resource Information Systems in a fairly deep way, and are placing big bets on where it is going. They have evidently not become complacent in the belief that what we are selling today is what we will be able to sell tomorrow.

However, the big bets could still fail. Without getting into detail, I will say that our current plans are ambitious and it is possible that we might not succeed. But at least the company is still trying to move where we think the market is going.

The next thing I learned is to never forget the Iron Triangle, which is the name for the “fast-cheap-good, pick two” trope of project management. Basically all project work has risk involved at some level, and that risk must be accommodated by allowing elasticity in at least one of timeline, deliverables, or cost.

The Iron Triangle is almost like a law of physics in software development. Actually, in IT, your biggest cost is almost always labor. Hiring good engineers takes long enough that, at a practical level, most software projects that take less than six months to build essentially have to do so with a fixed team size. And that’s before we get into the diminishing returns from adding engineers to a project. All of which is to say that, for software, you can only really choose either the deliverables or the delivery date, never both.

Every managerial job has some kind of inviolable constraints that are intrinsic to the task or domain under management. I have worked in environments where I was expected, as a manager, to violate these constraints regularly, whether it was to deliver a fixed set of features on a set date, or to try hiring very senior engineers with offers of ISOs instead of market-rate salary.

What I learned is that it is my sacred duty to tell the people I report to when I think they are full of shit. I should have quit those jobs rather than agree to the impossible and doom everyone around me to fail.

The third bullet point is “first, do no harm” which paraphrases the Hippocratic oath, of course. Basically, as I said, I got into this industry with a tremendous amount of idealism about the world-changing potential of technology. I, and so many of the people I came up with, believed fervently that, if we could give people more access to information, and better ways to connect with one another, then the world would automatically become a better place.

We have learned to our dismay that nothing could be further from the truth. The creeping rise of fascism and autocracy at the expense of democracy goes to show that what we have actually done is merely give evil people better access to influence the credulous and under-educated.

Technology is never more than, at best, morally neutral. We naively failed to imagine what malign, selfish individuals could do with the Internet. Now our entire society is paying the price.

My current job does not have such a blast radius. The worst possible use of our product is that we might someday accidentally leak someone’s performance reviews or compensation numbers. Not great, but not society destroying. Meanwhile, the product could be used to help employees get feedback that might help them actualize their professional potential.

Speaking of which, my fourth point is that you don’t have to actualize your potential as a human being while on the job. It’s a great myth we have in Silicon Valley, that you should be passionate about your work, that it should be the thing that gets you out of bed in the morning.

I agree that it would be nice. I came to my current job feeling that leadership was my calling in life, and that my purpose was to have more and bigger impact by leading bigger organizations with more people and more scope.

Well, in the three years I have been with the company, I have only seen one Senior Engineering Manager get promoted to Director, and that one person is so talented that they cannot be taken as an example of anything. Meanwhile, I have watched plenty of Engineering Managers leave, and more than one engineer who had become a manager later make the choice to switch back.

For a company whose original product is aimed at supporting performance management, it had started to seem like the cobbler’s children were going around unshod.

Certainly I have worked my ass off and not gotten promoted for my efforts. Equally unquestionably, it was me who worked hard on the wrong things, or did so in the wrong way. I am not saying I should have been promoted for my work.

But it had become equally clear that I was not going to get the support from the company to change that reality on the job. So I changed tack. I started working more reasonable hours, and maintaining a better work-life balance. My mental and physical health improved dramatically. I took up blacksmithing, woodworking, gardening.

I learned that it is not only my job to support my reports in their self-actualization on the job, if that’s what they want, but also to model for them what good work-life balance looks like. To make sure they know that they can treat their job as, well, just a job. If you look at my teammates, they work hard during the workday, and then… they go home to their families and their hobbies and other activities.

Only one of my direct reports has quit in over three years, and that’s because he was offered VC money to build his dream. May God help him and see fit to remind him of the bit about product-market fit.

All of this is to say, working at a startup is an adventure, and every adventure comes at a cost, with the possibilities both of reward and also of failure.

My biggest professional hope is that my current employer becomes fabulously valuable, and that everyone at the company gets to take home some of that value. My biggest fear is that we do not. This last comment got a laugh from my audience. I thanked them for the opportunity to be on this adventure with them.

I hoped I hadn’t rambled. I didn’t want to be that guy who overshared at work. I probably should’ve played it straight, or at least gone and gotten a snack. But that’s not really who I am.

If you’re still reading this, please write and tell me if you think I shot myself in the foot. Ceterum censeo imperdiet vigilum cessandam est. Thanks.