Are You Successful Enough?

You’re in bed at night, thinking about your life and job.

I feel stuck, like I’ve stagnated. With my years of experience, I should have come further by now. I’ve only ever been an Individual Contributor, fixing bugs and building new features. I’ve never led a team.

I Should Be Leading a Team By Now

Be careful what you wish for.

I followed the Default Path—the standard path society tells you is the road to success. I was a Developer, then a Senior Developer, then a Tech Lead, then a Team Lead. One night, I was lying in bed thinking about my life and job, and I realized I didn’t like it at all. I did not look forward to getting up in the morning and getting to work. In fact, I dreaded it. Why, though?

As long as you’re not homeless and your fundamental human needs are covered, your baseline happiness will stay the same, even when you get a raise, a bonus, or a fancy title. You might get a brief high, but then you wake up again, and your bar for what’s normal has reset itself, and you’re just as happy or unhappy as before. You’re on the Hedonic Treadmill, and as soon as you accomplish something, your mind defines this as the new norm, and you start wanting more.

You might say you need that raise. Why though? Do you really need all that stuff you are buying, or are you just buying it because that’s what everyone does?

Too many people spend money they haven’t earned, to buy things they don’t want, to impress people they don’t like.

• Will Rogers, ca. 1920.

Optimize for everyday happiness, and forget about prestige.

You’re a great developer, and now you want to be a leader, too. When jockeying for that promotion to management, many fail to consider how different that job is. This is an entirely different skill set, and what you’ll be doing all day is very different. You’ll find yourself in endless meetings. Lots of planning and performance reviews. You’ll be in charge of the growth of everyone on your team. You have to cater to the personal needs of all of them and have regular 1:1s all the time. You’ll learn about Performance Management—how to coerce the most out of your subordinates. You may even have to stack rank everyone on your team, having to let the ones you ranked lowest know that they are Low Performers.

Do you like to make things?

I once overheard my manager say something like, “Wow! I’m getting so much work done today! I’ve had 11 meetings!”

Did you ever feel that being in meetings is how you get things done?

There are two types of schedule, which I’ll call the manager’s schedule and the maker’s schedule. The manager’s schedule is for bosses. It’s embodied in the traditional appointment book, with each day cut into one hour intervals. You can block off several hours for a single task if you need to, but by default you change what you’re doing every hour. ​> When you use time that way, it’s merely a practical problem to meet with someone. Find an open slot in your schedule, book them, and you’re done. ​> Most powerful people are on the manager’s schedule. It’s the schedule of command. But there’s another way of using time that’s common among people who make things, like programmers and writers. They generally prefer to use time in units of half a day at least. You can’t write or program well in units of an hour. That’s barely enough time to get started. ​ When you’re operating on the maker’s schedule, meetings are a disaster. A single meeting can blow a whole afternoon, by breaking it into two pieces each too small to do anything hard in. ​>

• Excerpt from Maker’s Schedule, Manager’s Schedule, by Paul Graham (2009)

There is a whole field of education for becoming a manager, entirely skipping the part where you work as a developer for years first. Ask yourself why you didn’t do that in the first place.

I’ve known highly talented developers who did not enjoy being in a management role and went back to being Individual Contributors. I am one.

So what should I do then?

If you work in Big Tech, there are senior ​​IC​​ paths (architect/staff/principal engineer) that are generally much more pleasant roles for those of us who enjoy making stuff.

Show initiative. Demonstrate why you are valuable. Talk to your manager about what you want, and see if you can join a mentor program or pitch a project you could own. If your company can’t offer a clear path onward, consider switching somewhere that does.

Or, for an alternative path to self-growth, join a small startup or make extra income from a side project.

Just don’t become a manager.