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I Wish I Knew

This is a post about things I wish I knew when I started my career.

I Wish I Knew


This is a post about things I wish I knew when I started my career.


Management is a job description, not an honorific. Lots of managers get their positions through some combination of seniority and being a good individual contributor. Turns out, this is a poor model for choosing and promoting managers. Early in my career, I had some very bad managers. Seeing that they were good individual contributors, I blamed myself as they innocently but relentlessly scarred my professional development, self esteem, and productivity. I’m just bad at being managed, I thought. They seemed to agree. Eventually I experienced good managers, and as I got to a place in my career where I was hiring and managing a multi-disciplinary team myself, I realized my thoughts about management were all wrong. Yes, you need to be a strong individual contributor. You need to have experience in the functional areas you are managing. But your main job is to make it possible for your team to do awesome work together. Management might ultimately be a broken and unsaveable institution, but it’s a beautiful thing when managers realize it isn’t about power or control or accolades or their individual work. It’s about being 100% focused on making your team amazing - facilitating prioritization, optimizing processes and workflow, creating space to learn, bringing talent together, resolving conflicts, putting a bitter end to the forces of randomization and destruction wherever they come from, and making sure people are happy, fulfilled and working on what matters.

Reliable is better than brilliant. Our industry has a toxic mythology of the wonderkid. The visionary, rockstar, ninja, mad scientist, genius. From dust, they emerge fully-formed with strategies both vast and seductive, divinely inspired prototypes, and rousing bits of analysis, ideology, and declarative. They are prone to phenomenal periods of output, brilliance, even mania … and just as abruptly disappear. They do their best work alone and generally fail to start or finish group work. I’ve worked with people like this a few times. I now actively avoid them. Companies tend to be indulgent of these individuals and even promote them, enamored with the flashes of genius and primed by industry lore to inflate their value. But teams suffer as these “rockstars” are held to a different set of standards than other employees, don’t meet their commitments and can’t be relied on for long-term projects. After observing many of these individuals in action, I’ve realized that the output of hard, reliable, focused work over time, while less glamorous, always outweighs the value of short, ego-centric storms of genius. Now I strive to be and to work with people who can be counted on, who are reliable and trustworthy, who act as part of a team rather than a lone hero, and recognize that execution is more important than inspiration.

Burn bridges. It will be fine. When I started working in tech, everyone told me: “Just remember, you’ll be seeing these people for the next forty years.” In some ways, tech is a much smaller and more incestuous scene than I ever imagined - and I grew up in the midwest. There are also people in it who are dishonest, manipulative, abusive, bullying, mean-spirited, harassing and destructive. Early in my career I was very paranoid about maintaining amicable relationships with these individuals or staying quiet despite my moral qualms about their actions, because I was always told I’d have to work with them again, and that someday they might be on the other side of a hiring board or committee or collective I needed something from. I’ve since realized that these very fears ensure these assholes will have long prosperous careers, where we’re all forced to see them again. If someone is a bad actor, I no longer fear telling them that their behavior is damaging or wrong, or bringing it up in the workplace or community if merited. I’ve only made a handful of enemies in my career, but I’m proud of each one - because they represent a stand I took against people I would never want to be associated with or work with anyways.

Quit your job when the time is right. Often the work we do in technology can be extremely consuming, intense, rewarding and personal. You can grow extremely attached to a job or a startup, especially one that you’ve watched and helped grow, maybe over the course of years. Each time I’ve left a job so far, I waited way too long to do it because of the profound existential angst - and guilt, and fear, and attachment. Now I count “waiting too long to leave” as one of my top career mistakes. Look, you’re joining a startup early in your career. You’re learning and growing and changing, and so is the company. If you leave, it will be okay - you will fall in love with another company. Looking back, I’ve tried to put my finger on symptoms I was ready to go, and here are a few: difficulty staying focused on work, starting lots of side projects, thinking much more about other companies and problems, feeling I was no longer learning new things, and being anxious or depressed about politics and internal drama. Now I try to watch for these signs so I don’t make the same mistake again.

Enjoy the “tech community” in moderation. At the very beginning of my career, I went to countless meetups, conferences, happy hours, un-conferences, hackathons. For a time, it was even part of my job as I did a great deal of technical evangelism. Later, focusing more on product, design, marketing and eventually management, I still attended many of these events. Frankly, it can be hard to avoid them, no matter what role you have in a company. I have eaten more bad pizza in my life than anyone should have to eat, drank more flat beer than anyone should have to drink, seen more shitty apps demoed than anyone will ever use, watched more dull, contentless presentations than I like to admit. Sadly, much of the so-called “tech community” is essentially a corporate-sponsored marketing machine. Events and meetups can be exciting. You meet lots of people. You can build community, awareness and partnerships through them. But ultimately both individuals and companies can place too much emphasis on them. Over the past few years, I’ve actively sought to cut down how many events I attend, spending that time instead building 1:1 relationships, trying new things and reading/writing. I’ve become both more well-rounded and happier.