I want to preface this by saying how grateful I am. I’m gainfully employed. I’m alive when software engineering is not only possible but one of the most lucrative, opportunity filled careers.
From the first time I started writing code in my high school CS class (shoutout Mr Simon), it was something I was passionate about. I could immediately drop into flow state.
I love working on the internet. I love the creativity behind building beautiful UIs or intuitive APIs. I love impacting the bottom line of a business. I love problem solving. I love making people’s lives a little better.
Some of my favorite moments in my career were when there was a critical outage, it’s fucking go time, and I’m moving as absolutely fast as I can to debug or fix something. It feels almost like sport at that level.
I’m one of the lucky people who is in a career they have a natural aptitude for.
That said, I’m having an existential career crisis at the moment.
Brief career recap
I’m 33. I’ve worked at a number of different software companies and industries for the last 10+ years.
I have been an IC my whole career. My “peak title” was when I was at NerdWallet ~5 years ago as a “Staff Software Engineer”. Since then, I have expanded my skillset across the stack and learned a lot from a few different companies but have been around an equivalent level of responsibility and impact.
While I’ve generally be a high performer, my career trajectory feels like it has flattened quite a bit. I thought I would have done more by now. And with the steady march of AI threatening to dramatically change the landscape, I am feeling the pressure.
This has left me asking myself some existential career questions.
Is there more to my career than being an IC software engineer? How do I get more fulfillment, and have more impact and responsibility in my career? How do I better position myself for the AI revolution? Where do I go from here?
An honest reflection of my decision making
Looking back on my career so far, I have made some decisions that, I don’t want to call mistakes, because that’s easy to say with the power of hindsight, but they were too emotionally driven. They were more controlled by wounded parts of my psyche than I’d care to admit.
So I’d like to reflect on some pivotal decisions that shaped my journey. I’ll start with one win and the rest will be areas of improvement.
✅ Going to DevBootcamp in 2014 was the best decision I’ve ever made in my career. It jumpstarted my career as a software engineer and gave me a world of opportunity. For someone who wasn’t a very good student in most of my academic life, I locked the fuck in for this 6 month bootcamp and learned as much as I could.
Things I might have done differently
- ❌ Not chased money or status
- ❌ Kept pursuing entrepreneurship
- ❌ Fostered more professional relationships
When I went to Dropbox, a big driver was both it was the highest comp offer I had at the time and it felt the most prestigious. It felt like I was officially validated as an engineer by getting to work there. Imposter syndrome begone.
I learned a ton at Dropbox but in hindsight the reasons I joined were not that healthy. I was playing a status game. Funnily enough, some of the other offers I had ended up being far more financially lucrative, so it ended up being the wrong choice on that metric as well.
I aspire to be more altruistic but a part of me is eager to for material success / external validation. Going forward I want to be more aware of this. Just mindful that this part of me exists. I don’t need to suppress it, but I should at least acknowledge it very well may be a perverse incentive.
A better guiding principle in my career is probably to focus on building things that are interesting to me, and let the material success follow naturally.
I have an entrepreneurial spirit. I would love to create something that doesn’t exist in the world. To shape the future, even if just a little. I love the game of business. It’s the ultimate sport.
A few times in my career I’ve tried to build a side project or startup but what has now unfortunately become a recurring theme is I’ve given up on them relatively early. It’s easy to let self doubt creep in when working alone on a business that doesn’t seem to be taking off.
I have to internalize that building a business will take time, require many iterations, and let time compound and work for me.
NerdWallet in particular was a great place and time for me to meet people. However when I was there I was grinding super hard. I told myself “I’m here to work”. I didn’t socialize that much and didn’t foster too many relationships. This was in hindsight quite naive. NerdWallet had a beautiful people culture. I think there would have been a lot of tailwinds to fostering more professional relationships, for example having more potential cofounders to build something with.
In general I have let way too many professional relationships fall by the wayside and now don’t feel great about the health of my professional network.
Where do I go from here?
Look, I’m no spring chicken anymore but I still have a really strong drive and ambition. I want more meaning out of my career. I am hungry to do more winning. I think my ceiling is still pretty high and it would be sad for me if I don’t get closer to actualizing what I feel is my potential.
At the same time I have to accept that maybe my career will not pan out quite how I think it should. Enough time has passed where there is a real possibility my career ends in a state I’m not thrilled about. Maybe I won’t align what I feel I’m capable of internally with what I actually achieve.
But I’m also in the best state mentally and physically I’ve ever been in. I think I am in a position to do better than just extrapolating the last few years into the next decade.
Below are some possible career paths I’m thinking about. The overarching theme is I want more responsibility, impact, and meaning.
Do the best work of my career as an IC
This is probably the most stable path to a successful outcome from here. I still have room ahead of me to grow potentially into a principle engineer. But I would really need to lock in and become more technically proficient and well rounded to get there.
Picking the right industries or companies to work for is also a big part of this. Frankly my track record hasn’t been that great here.
Bootstrap my own small business or startup
Getting a startup or small business successfully off the ground would make me the most personally fulfilled.
There’s flexibility here in terms of bootstrapping and how much of it is “mine”, e.g. if I joined an existing early stage startup I think that could suffice. But the best version of this is something I create, myself, bootstrapped without any external funding and build it to a significant outcome.
The success case indiehacker bootstrapper model is also the best outcome as far as personal freedom. Lots of “successful” VC funded startups don’t always up in that much of a success for the founders. With both AI tools at my fingertips and AI impacting many different areas of software, it’s maybe never been a better time to bootstrap a software business.
As mentioned above however I have a history of both not choosing the right things to build and not being able to sustain the level of resilience needed over a long period of time to work on them. Can I overcome that? I’d like to think so. But going this route also carries the most risk.
If I spend some years trying to build a small business or startup and it doesn’t work out, would that leave me in an even deeper existential crisis? Maybe not because I would at least have been proud for taking the shot on goal.
Become a people manager
I love being a doer but I think I also have the people skills to go into management. This is also the most stable path to a leadership position.
I have been offered to do management at various points. As you can see I’ve recently done a ton of introspection and personal growth so I am better equipped to help others on their own journeys now than I’ve ever been.
As I get more senior in my career, more delegation will be required anyway. So maybe it’s natural to go the management route. This would also open up the most opportunities for me. It keeps me upwind.
Hard pivot
Maybe I should just start preparing for the AI apocalypse as best as I can and hard pivot. I don’t know what this would be. Go back to school? I’ve always wanted to be a comedian, should I start doing standup comedy? 🤣
I’m mostly kidding but I do feel a career reset of some sort is on the table. I’m not sure what that would look like yet.
Ending with a promise
At the end of the day, I know that my career progression isn’t going to be linear. It’s going to zig zag. I haven't always made the best choices, but I'm learning from them. I’m optimistic I can course correct, adapt to the changing environment, and get back on a trajectory that will make 80 year old me proud.
If I’ve learned anything from Interstellar, it’s that no one is coming to save us, we have to save ourselves. So I promise to my future self, I am going to figure this out… if it’s the last thing I do I’m going to figure it out.