Majestic Cheetah asked
answered 1h ago
Hey Philip, your experience is impressive, and thanks for putting in the effort to share your thoughts.
I find myself in a bit of a career dilemma and would really appreciate your perspective.
I genuinely enjoy systems, coding, engineering, math, and solving technical problems. What I’ve struggled with is the corporate environment around engineering — deadlines, organizational politics, people management, and sometimes spending more energy navigating the organization than actually building things.
I also came to financial literacy relatively late in life, but over the years I've become much more interested in investing, capital allocation, and thinking about businesses from an investment perspective. Through saving and investing consistently, I've reached a point where my family has a solid financial foundation and I don't feel much financial pressure to start to work immediately at all cost.
Earlier in my career, I was quite focused on titles and career progression. I eventually reached a fairly senior engineering position at a large tech company, but I was working in an area where I didn't have as much depth or passion as I would have liked. I was eventually laid off after about a year.
I then joined a smaller startup, but that experience also didn't work out and I left after only a few months. With the current job market being difficult, I'm increasingly concerned that these short recent experiences may make my resume harder to position.
At the same time, I'm genuinely excited about data and AI and would love to spend the next few years working in this area. I'm even willing to optimize for learning, technical depth, and long-term opportunity rather than maximizing near-term compensation.
The confusing part is that, looking further ahead, I increasingly wonder whether my natural strengths may actually be closer to capital allocation / investing / evaluating businesses than being a career engineer. I still believe I have a lot to contribute technically, though, and I don't want to walk away from engineering prematurely simply because I've had a couple of difficult experiences.
At the same time, I am bullish to the AI trend and willing to join one of the AI labs both for more financial security and personal learning and fulfillment.
How would you suggest me position myself? What career advice would you give for me? Should I just focus on preparing interviews and trying to get into those companies and also finding a matching team?
Philip's answer
Recent experiences, especially with being laid off, can understandably affect self-confidence. It's completely understandable you're hesitant about re-entering the interview cycle and seeking another employer in the tech space.
You have several potentially great choices before you, but there will be unresolvable ambiguity as to how to move forward. A few thoughts:
How much do you want to explore or lean into your interest in capital allocation as a potential full time job? For instance, would a stint at a VC be of interest? Or even an EIR at a VC, which gives you a chance to interact weekly with the capital allocators while exploring your own projects?
Are there companies outside of the main labs that are also interesting to you? I ask simply because getting into the main labs is incredibly competitive, such that I'd recommend backup plans for even the most qualified people. If you're interested in AI, there's hardly a major tech company which doesn't have significant investments, or at least teams which focus on AI (whether that's fine-tuning models or building their own).
My guess, given only what you've communicated, is that you might enjoy a stint at a VC quite a lot. During my time as an EIR at Madrona, I was able to sit in on the weekly partner meetings where investments were discussed, but also meet with a bunch of founders and research my own startup ideas. If you were to do the same, you might find you enjoy the partner role, or perhaps find an operational role you love.