I did something this year that I thought might never happen again during my career. I got a “normal job”. I’ve been working exclusively on startups for at least the last 25 years. With the few exceptions being times when we’ve sold a project to a larger organization and I was there to help transition. And those transitions haven’t always been very positive. That made me think that I was just a startup person. Maybe I was just too feral to be able to exist in a structured organization for any length of time. I was very wrong.
Because of a long list of things that would only distract from the main point if I let myself get too much into them, I was at a fork in the road at the end of last year. I could either start up a new business or try to find myself a job somewhere. I was of course leaning toward the former. But also when I spoke to folks I kept hearing how horrible the job market is currently. I’m over 50 now, and particularly for folks in my age group I kept hearing that finding a good technical role is extremely difficult. Technical management not as much of a problem, but an individual contributor role would be different.
I certainly understand part of what folks see there. But I decided to go counter to the advice and at least try to find something inside an existing organization as an individual contributor.
Along the way I’ve found that many startup skills have translated insanely well to working inside a larger organization. That’s part of why I wanted to put a post together about this. For the older tech folks who maybe are having some issues, there might be a bunch of skills you have that you just need to figure out how to highlight. This is my partial list of things that surprised me in a positive direction when going into a more established company.
The set of skills around having a bias towards action work well in a number of different contexts. In the startup world when I’m working with a cofounder or talking to a potential customer I try to not just flat out say “no” to things. Interesting ideas come from all over the place. And even when something on the surface doesn’t seem workable, there’s often a core of interesting insight in the direction. I didn’t think the set of techniques I’ve built up for those interactions would be that valuable inside a bigger organization. But I’ve found the more often I apply it the smoother everything goes. I just treat everyone around me like my customers. I try to understand what they really want and not just what they’re currently asking me for. If they’re asking me for things that don’t seem to make sense I try to figure out what they’re trying to get done and how I can do something that progresses them in that direction. Everyone is my customer. The people managing the projects I’m helping with most obviously. But I found that the more I applied the idea all over, the smoother everything went. My teammates are my customers, my manager is my customer, whoever owns any of the repos I’m checking things in to is my customer. I try to find some way to make whatever I’m doing into something that helps them too. To my surprise it’s pretty easy to do after a few decades of startup life. I figured it might be hard to navigate the competing objectives in a larger organization, but I’m not feeling that part at all.
Juggling competing objectives feels almost trivial in a normal job compared to life in a startup. Sure, I have an actual task list to work my way through, with expectations that I track what I’m doing, contribute to reviews, handle a few async requests from other teams, keep an eye on what my coworkers are doing, and learn about the systems I don’t already know along the way. And I’m sure as I get more embedded in the organization the cadence of a bunch of those things is probably going to change. But I’m used to that list of concerns plus hiring a few new people, onboarding someone or getting an existing person ready for a new role they’re taking over, investor discussions, fund raising, customer onboarding, partner management, budgeting, product planning and tradeoffs, support, and some bit of legal review. Now, for the most part, I just need to get some bit of tech working. Sure, I might have to do it while the person who would normally help get it done is overloaded with other stuff. But compared to the average challenge I had to navigate before, totally doable.
And finally, the intensity is turned completely down. It’s easy to stay calm, cool, and collected when most of the problems you have are just that there’s a lot of work to get done. Sometimes it’s a bit of a scramble, and you might have to get inventive in how you stage things so that you can ship a partially working version while you figure out how to make the real version. But on my scale of intense projects that’s like a 1 or 2 out of 10. It doesn’t make it above a 7 until the current month payroll is hanging on the success or failure of the prototype you’re trying to hack together in the reception area of your next meeting. And if you can use that difference in your outlook to find a way to make the rest of the team feel more comfortable, or use your perspective to spot something that simplifies the situation for the rest of the team, you’re also getting a leveraged value from that. Helping not just keep your part of the project on track, but helping the whole team find a way through. I’m sure some of that is just from raw experience now, I’ve been doing this stuff for more than 30 years now. I should be good at it. But the startup side of the experience in particular seems to have cranked up the effectiveness of the methods I’ve ended up being comfortable with.
So for the folks out there who maybe are wrestling with the idea of what comes next. If you’ve been startuping, and you love your techie life, but it sounds like maybe you really need to get into management because it should be “the right thing to do” for someone your age. Please don’t accept that it’s what you need to do. The world still needs good technical people building things. Please don’t stop.