Humble Canyon asked

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Hi Philip, I’m in my mid-30s. I started as an E3 at Meta and have since grown to L7 at an AI company. Long term, I want to lead something big, and entrepreneurship is one path I’ve always been drawn to.

My career so far feels like it’s happened inside a big-tech bubble. I’ve grown a lot technically, but my sense of self isn’t as strong as I’d like. I also sometimes struggle to express ideas clearly and concisely, especially when speaking English, my second language. I don’t have much of a network outside it, or much exposure to customers, investors, and the practical side of building a business.

I’ll probably stay at my current company for at least another year or two. In the meantime, I’m using my work to practice communication and influence, and to get better at defining problems and deciding which ones are worth solving. But sometimes it feels like practicing in a vacuum, far removed from starting and running a business. I’m not sure how much of this will translate.

If you were in my position, what would you prioritize over the next year or two, both inside and outside work? How would you tell whether you’re making real progress toward entrepreneurship, rather than just getting better at your current job?

Thanks for being so generous with your time and experience. I really appreciate it.

Philip's answer

You mention you're "using [your] work to practice communication and influence, and to get better at defining problems and deciding which ones are worth solving." This definitely sounds to me like you're making progress toward real entrepreneurship. Those skills will transfer well.

The biggest question I have about whether you're making "real progress toward entrepreneurship" is whether you, like many people, keep telling themselves this for decades until they lose the motivation, or whether you will take that concrete leap at some point. I have a friend who has been talking to me about his life desire to start a company of his own... for literally two decades. There's a way in which the idea of a future self who's an entrepreneur can be a form of work escapism that quiets some dissatisfaction within us, a sense we aren't doing all we're capable of.

The only way you will know whether you're making real progress is if you set a timeline for yourself and keep it. You can definitely start your own company; literally anyone can. And if you save enough, you'll definitely be able to go a year without income given your strong past track record. The real question, which only you can answer, is whether you'll set that timeline for yourself and keep it.

Starting a company is in a way like pregnancy. I don't think anyone is truly ever ready for parenthood. Yet it's done all the time, sometimes successfully. I bet you'll find 90% of the learning is on-the-job.

You sound to me like someone who'll follow through on this. I'd love to hear back from you once you've started your company!

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