What I’d Tell My 20-Year-Old Self

I recently turned 45. While it was a disappointingly ho-hum event (Ryan Seacrest did NOT show up at my house, if you can believe that nonsense), I caught myself wondering what I’d tell my 20-year-old self if I were able to go back and dispense the modicum of “wisdom” (do finger airquotes here) I’ve picked up along the way. I can’t say there’s much, but I have a few things I wish someone would have told me when I was 20. They are:

Take chances. It’s easy to play it safe, and you’ll want to later when you have more obligations. For now, take chances, screw up, do what you can to make things happen that you are passionate about. Who cares if you fail. Now’s the time to chase what you really want, because you’ll never be this unencumbered again.

Fear is a useless emotion. It paralyzes you, clouds your decision-making, makes you second guess yourself. Fear is a mind killer. Do everything you can to realize the fear you feel is almost always massively disproportionate to even the worst possible outcome. We are not being hunted by tigers anymore. Do everything in your power to put fear into a corner and not let it out.

Your care-o-meter for what anyone else thinks of you should be pegged at zero. Live your life with integrity and character, and admit when you mess up. Acklowledge your mistakes and put them behind you. But do not care one bit about others think about you or your path, not even for a second. Live your life or you’ll wind up living someone else’s.


Adult life is full of complex issues that cannot fit into simplistic reductionist labels designed for 24-hour news channel talking head debates. If you are forming an opinion on an issue and you find yourself thinking in black vs. white, us vs. them, yes vs. no terms, take a break. Your thinking is wrong.

Bring a challenge to yourself, or a challenge will find you. We live in period when life is laughably easy: we all have computers in our pockets, and we have the sum total of human knowledge a search query away. This leads to a ton of potential idleness. You must challenge yourself – in a gym, in martial arts, by learning an instrument, writing a book, mentoring someone, confronting your fears. If you don’t find your own challenge to which to apply your strength, idleness and a lack of gratitude set in, and a challenge will find you – addiction, money problems, relationship problems.

Chasing material status is a tremendous waste of time, and it doesn’t lead to happiness.

If you have to ask if something is the right thing to do, it isn’t.

Find a mentor and ask questions. Someone out there has done the things you want to do, and they’re willing to help.

Meditate or practice mindfulness in another way. Quiet time is undervalued in our society, and we need it more than ever. If you can’t get away from the pings and tweets and emails and status updates and analytics of the modern age, you’ll never find time to be creative or reflect. Make time for stillness.

Lean into discomfort. Yeah, a lot of things in the real world suck and aren’t going to be pleasant. Learn to embrace the pain of a task or endeavor to make yourself stronger and more tolerant to everyday suffering. Full-time hedonism is a punchline.

Grit and toughness might be the most important character traits you can have.

Say yes far more than you say no. Open doors more than you close them.

Help your fellow man even when they don’t ask for it. Pay things forward. What you put into the machine is what you get out of it.

When your child is young and wants to play with you, put his head on your shoulder while watching TV, or tell you about his art class painting, be present for every second, no matter how tired or distracted you may be. You’re his hero for only a few years, and you’ll never be loved in this way again. Make amazing memories and cherish them.

Have a great weekend, everyone.

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