Turning 50: The Top 14 Things I’d Tell My 23-Year-Old Self

Don’t wait too long to get started on your dreams.

Turning 50. Yes, it’s just a number. But it’s a weird feeling. Like I’ve crossed a line in the sand. Back when I was a kid, this age seemed ancient. Now that I’m here, it doesn’t feel so bad. In fact, I feel about the same as I did in college. Time is relative, right?

I have many people in my company, Simpler Trading, that were born just after I graduated from college. Their perspective on life is different than mine. They have fewer bumps and bruises from life’s curve balls. They are figuring out their likes and dislikes. What to do next. As if they have all the time in the world. Well, it goes by quick. Don’t hesitate too long.

Upon turning the big five-oh, here’s what I’d say to my 23-year-old self:

1. If you aren’t sure what to do next with your life, do the thing that scares you the most.
2. That thing that’s keeping you up at night filled with worry? You aren’t even going to remember what it was at this age. Even if it seems like the biggest, most fearful or shameful thing you can imagine. It’s just experience.
3. Learn to enjoy eating that shit sandwich for the lessons you will learn and the skills you will develop next time around. I promise, you’ll appreciate it later, so learn to appreciate it while you are in it.
4. Trying to only do or say things that make you look good or smart will be the single biggest obstacle to growth and the greatest rate limiter in your life.
5. When you hold a grudge towards someone, they own you. Forgiveness is for you, not for them. Cut the chains that bind.
6. If you have your health, you have 1000 dreams. If you lose your health, you have 1 dream.
7. It’s easier to ask for forgiveness than permission. Don’t waste a breath trying to justify your “why” to anyone. Just start.
8. There are no rules, only guidelines. Rules are for sheep.
9. It’s the little things now that become the big things in your memory later. One day your kid won’t want to hold your hand when crossing the street.
10. Once in a while, tear up your to-do list and give yourself the gift of a clean slate. Forgive yourself and all of your mistakes and stupid decisions, take a deep breath and make today the first day of your new life.
11. Just keep swimming, without judging others or fearing their judgment in return.
12. If you think the world is out to get you, you’re right. And if you think the universe is rigged in your favor, you’re right. Pick one.
13. In the beginning, the road to opportunity starts with saying yes. In the middle, the road to freedom starts with saying no.
14. Tell your friends and family that you love them. Even if you feel it strongly, it’ll only be real for them if you tell them.

Aging is an extraordinary process where you become the person you always should have been. — David Bowie

Thanks for listening. Here’s to the next 50 years.