Forgive me if I seem presumptuous in my advice here. You've done things in your career that I can only dream of doing. What I can say is that I've somehow managed to survive a quarter-century in a string of Big Tech companies without dropping out (yet).
It sounds like you may have been looking at the currents and picking the one that seemed best one to swim in. I found there's often -- but not always -- another option: build a dam. In other words, change it up. Alter the landscape. Seek to change the business in a way that nobody's been willing/able to do before. Looking back at my career I found I was happiest and most successful when I was able to tell my boss what I was doing vs. waiting for my boss to tell me to do something interesting/impactful/etc.
When that option doesn't seem to be presenting itself, it's probably time to move on. But I've found it's often worth giving it a try first.
A couple of times I needed to earn the right to create my own destiny by pushing through some grunge work, but once I established a degree of trust with my management chain, that was capital I could "cash in on" by proposing something big, new, and interesting. It never ceases to amaze me to see how boldness often gets rewarded. I just saw a co-worker of mine draw blood from a stone (funding-wise) by proposing something ambitious and controversial last week. Suddenly they're a TL of a new team this week. They've built a reputation for "just getting it done," so management has confidence in their ability to execute and drive results.
Whenever I'm starting to feel stuck in a rut, that's when I open a blank document and start hammering out a design for something new. I'm not even thinking about promotion when I do that. But somehow, somewhere down the road, either a promotion or a bigger opportunity with another company has always come of it.
Context for others: steelframe and I were teammates at Microsoft in the late 2000s.[0]
Hey steelframe! Good to see you here again!
This is good advice and something I wish I'd recognized earlier at Google. For the first few years there, I was under a manager who had 20+ direct reports, so he probably didn't have time to think of the best projects for me.
I probably would have been better off figuring out my own high-impact project rather than focusing on fighting short-term fires that kept popping up for my team.
In certain ways, I solved this with the founder route because I get to skip the "earning the right to create my own destiny" phase, but in other ways, there's inescapable grunge work like legal compliance, taxes, vendor issues, etc.
Can you explain how this doesn’t amount to saying “You seem like you’re brave. There’s another option: be a coward.”
You don’t seem to be proposing an alternative strategy with equivalent risk/reward dynamics, rather, it seems like what amounts to anathema to entrepreneurship.
I saw your post about selling TinyPilot, congratulations! FWIW I agree with all your points in your 2018 article, and I wish I had left Google sooner too.
I was wondering if you could share if you are working on a new project? I saw your posts about fuzzing a PDF parser but there's no context if this is for a new project, or I missed it :-).
No, the fuzz testing is just for fun and probably not anything serious, although it would be fun to find a fuzzing target that has a good bug bounty program.
My wife and I just had our first child, so I'm mainly focusing on family time for now and slowly easing back into work over the next few months. My main priority is to finish the book I've been promising to write for the past four years.[0]
I've been following your story for the past several years since you wrote this post and it helped me understand the realities of indie hacking and startups more than most articles, so thanks for writing in public and documenting your journey, I'm sure I'm not the only one you helped. By the way, whenever I see your username, I always seem to read it as Mount Lynch, haha.
I don't have anything useful to add but just want to say, like many others have said, I really appreciate the way you have continued to document your journey from start to today and not shied away from sharing details. Thank you for that!
Nice to see you on HN :-) Too bad we couldn’t reach a deal on your Keto site, but hopefully the new owner takes care of it well. Can’t wait to see what you will do next! Cheers!
I was 32 and single, so I had a lot of freedom to take the risk at that point.
I don't want to say my exact net worth at the time, but I earmarked $400k to last me five years of trying to make it on my own.
$400k was kind of extreme because I assumed I'd maintain the lifestyle I had at Google, including my $4.2k/mo apartment in downtown Manhattan. I ended up moving to Western Massachusetts, where my burn rate was significantly lower and could have been even lower if I rented an apartment instead of buying a house.
Happy to answer any questions about this post.