Don’t join a startup to ‘get rich quick’: Career advice from a 30-year Silicon Valley veteran

Photo credit: Carolina Pimenta / Unsplash

Ever since I retired last year, I’ve received a lot of requests from former colleagues for career advice. These usually boil down to a few broad categories. I figured it might be useful to write them down.

Caveat Emptor: I don’t claim to have made good choices in my own career, only to have learned from making bad ones. Hindsight is 20/20. My only hope is that others don’t make the same mistakes I did.

And if you don’t like my advice, remember: It’s worth every penny you paid for it.

Should I stay or should I go now?

Perhaps the most common question comes from colleagues who are disillusioned with their current situation: either because they feel trapped in a dead-end job, or a declining company, or because they don’t feel valued by upper management. Let’s just say there is a lot of discontent in the industry right now.

My advice, simplistic as it may seem, is to echo Steve Jobs: do what you are passionate about and don’t worry too much about the financial aspects of the decision. We all make mistakes in life, but I for one would rather look back fondly at all the lessons learned while trying out new experiences than remorsefully at the opportunities missed.

Every job comes with a dose of daily frustrations. Don’t run away from those problems. Run towards something you feel passionate about.

If you are aligned with the company strategy, believe in what you are delivering to the customer, have a strong team of collaborators around you, and can’t wait to get up in the morning to go to work — then, by all means, stick around. In all likelihood, the grass is not greener on the other side. Another 10 or 20 percent of annual compensation will not change your life. And I bet the other company has as many, if not more, problems than your present employer.

If, on the other hand, you feel miserable every day when you go to work, if you feel you’re stuck in a rut and are not learning anything new, if you disagree with the strategic direction of the company, if you see key decisions being made for political reasons — then I guess you know what to do. Go find something you can be passionate about again.

Here’s another factor to consider: I claim that 99 percent of all software written today will be obsolete, abandoned, irrelevant, or otherwise replaced within the next five to seven years.

OK, maybe that statistic is intentionally high to catch your attention. There is a bit of hyperbole in that statement, but not much. And I’m not talking just about consumer software, but also enterprise and cloud software. I wish the creative process wasn’t so wasteful, but I’m afraid that rate is only accelerating.

So, ask yourself: what’s the most important thing you can do for the next five years of your career? Maintain software that was architected a decade ago, became legacy five years ago, and will be around for at least another five years? Or would you rather roll the dice and try working on “new stuff?”

Remember what Enzo Torresi said about software: “The reason that God was able to create the world in seven days is that he didn’t have to worry about the installed base.”

I want to do my own startup.

Stop. Think. There are already thousands of startups out there. I bet there are already a dozen working on exactly the idea you have. I bet there are a dozen things you haven’t thought about — from supply chain to marketing plan to developer evangelism to ecosystem support to release maintenance to competitive landscape.

Private or public? Clouds, that is.