Lost

[…] Not all those who wander are lost […] — J.R.R. Tolkien

Some of us are lost, at least for a time. I know I was.

My problems are definitely first-world problems. I was sharing this with a friend, along with the thought I should just shut up about it. He said, “Yeah, but they’re your problems.” He also suggested I should write about it on the off chance others might find it helpful.

This isn’t my origin story. Maybe I’ll share that another time. Suffice it to say, I’ve never had a career plan, a ten-year plan, or anything like that. If you asked me where I’d be in 5 or 10 years, I could give you a nice sounding answer, but it was just something I put together on the fly, no real commitment on my part. I’ve lived a charmed life. I’ve not needed a plan. Except…

Towards the end of 2022, about a year before I wrote this, I was negatively impacted by a reorg. I want to be clear and not overstate. I wasn’t shafted. I didn’t get the worst of it. I wasn’t the direct target, and my day job mostly stayed the same, except for one critical detail. Previously, my boss, a senior director, reported directly to the SVP of Software for a Fortune 100 company. I had my boss’ respect and confidence. Unfortunately, my boss was directly impacted by the reorg. This lead to me being pushed down a level and a different senior director in my chain reporting to the SVP.

Now, here, I should call out one of my many failures. I didn’t reach out to my new senior director. I didn’t request the time to see how, or if, my work might align with his vision. That’s a failure on my part. I ascribe no malice to this senior director. I know he was working on very important initiatives, and how could he be expected to know how I might feel about the changes?

Separately, I was hearing from trusted, but secondhand, sources my work at the time wasn’t conducive to my continued advancement. This wasn’t a complete shock to me. Completely reasonably, there is a fair amount of emphasis placed on contract work for advancement in the Fellowship, working on programs making actual money for the company. My work in open source wasn’t directly contributing to the bottom line. (Though, perhaps failing to be able to articulate the value is yet another failing on my part.)

And separate from all of that, I was struggling to come to grips with how I could best provide value to any organization. I’ve been a software engineer for my entire career, always an IC, often a lead, and never a people manager. Even just veering into being an architect, multiple times, had ended in personal dissatisfaction. I like writing code, leading, and community engagement. And for the last few years, in my day job, I found myself writing remarkably little code. Add to that now feeling like less of a leader, an increasing distance between my role and the seat of power…

I volunteered to be reassigned. So, no coding, decreasing involvement with leadership, and I volunteered to walk away from the bulk of my community engagement. How many mistakes am I up to in this story? But, hey, I’ve got another one coming. Let’s throw some hubris in there.

I was offered some great opportunities, roles people would legit kill for. I chose one in a research-focused part of the company. Again, I should recognize my privilege, “I chose one.” That’s not even the hubris. My hubris came in the form of me assuming my new leadership knew not only what I was good at but also what I was interested in doing.

Let’s pause there a second.

What was I interested in doing? Truthfully, I had no idea.

I had had some conversations about executive roles at different organizations, none of which had gone anywhere. I thought I might like that. Besides, that’s where you’re supposed to go, right? Problem was, I don’t want to be a people manager.

I had turned down a couple offers at big name tech companies to go be an IC because I thought I really wanted to be in leadership.

So, I didn’t really know what I wanted to do. One of my close friends, a mentor, was convinced I knew, but my pride wouldn’t let me see it. Maybe, but I can say at the time, I definitely didn’t know consciously.

How did I get clarity? First, I can’t say I’ve achieved true clarity. I still sometimes can see myself pursuing alternative paths in the future. And being a founder still has a little allure (though Glauber may have convinced me otherwise); I’m looking at you Wasm-space. Second, let’s answer the actual question. I spent a lot of time thinking about the people I respect, the kinds of things I would like people to respect me for. I don’t have any idols, but I respect a lot of people. I spent hours trying to figure out commonalities of the people I respect most in my career field.

What did I find? I found technical leadership. Most, though not all, were ICs with no direct reports. All had either influence or direct authority to shape technical direction for their organizations. They had enough autonomy to explore new technical directions. They shared what they learned. They made time and space for others. Those were things I wanted, things I wanted to be respected for.

But, back to my story about how I failed to let my new leadership know what I wanted to be doing. The problem was, I didn’t know what that was at the time.

Unfortunately, like most people, there are plenty of things I don’t want to be doing full-time. That’s what I ended up doing, work I wouldn’t mind as part of my job had become all the job. I did let my manager know, but I could have done a better job of explaining my growing discomfort.

So, I looked for something else. There were lots of dead ends, but I’m super excited about where I am now and the impact I hope to have.

This isn’t a knock on my former organization. I still fully believe it is a great company, is a great place to work, and has great people.

I made mistakes. I was wandering. I was lost. It made me miserable, almost physically ill. My poor, amazing wife had my back the whole time. Additionally, I had plenty of friends listening and trying to help.

I still don’t have a five- or ten-year plan. But, I’m no longer lost.