I have no real regrets about my 20s, because I needed every experience to get to wherever it is I am today. I had to go through all of them, even if some took too long, etc.

But if I was stronger or better, or who I am today doing it over again, my top re-do ideas:

  • Grad school for 3 years was way too long. Maybe skip it. Grad school is great for some, and I needed it as an enabler. But 3 years? That was a loooong time. You can do so much more with this time, unless you really need it.
  • Be with who you want to be — in work and otherwise. We learn this later. In personal and if possible, business relationships. This is one of the best parts of starting a start-ups. You can pick who you want to work with, which you don’t get in almost any other job. Do this in your personal life, too.
  • Living somewhere else, far away, was very helpful. I lived for a year in Japan and experienced a very different culture. This has helped me a lot later in life. Backpacking through Europe though? Less so.
  • Do what you are great at, and work incredibly hard at it. I didn’t start working incredibly hard again until I was about 26. It was good to take a mellow break after college, but you don’t really get anywhere without insanely hard work. Don’t follow your dreams necessarily (they may be folly), but do follow what you are actually good at. Do more of that, a lot of it, and you will get really, really good. That puts you ahead of the pack.
  • Move on from a bad boss fast. There is no upside here.
  • Get one iconic experience on your resume, and do enough to leave a lasting impact. Work at a super hot start-up — for a boss that loves you and will recommend you. One A+ recommendation from a top startup will carry you for 10+ years. Or do the same at Google, Facebook, Salesforce, wherever for 2–3 years. Let this be your grad school, maybe. Do an incredible job, and only move on once you have accomplished something meaningful and referenceable. I’ve had 2 bosses whose references carried me my entire career.
  • No real shortcuts. I tried to take some shortcuts in my early 20s. Never again. I do still try to fast forward everything. Launch early. Hack it. A good product today is far better than a perfect product tomorrow. But while you can cut some corners, you still have to do the real work. Do what it takes to get where you want to go. Maybe do the steps as fast as possible, and skip the optional ones. But put in the time in the mandatory steps.
  • Believe in what you do. Find what is great in the job you have today. And lean in there. There are great things in almost every company, even the most flawed ones. Find a way to enjoy that and celebrate that. It will be infectious, and you will become a leader on at least some level quickly.

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