Letters to My Younger Self: What I Wish I Knew

As I gear up for the release of my new book, Hey Dad…: Everything You Should Have Learned About Life But Didn’t, I’ve been thinking a lot about the younger version of myself.

The kid fresh out of school trying to land his first job. The young professional chasing the next title without a clue about work-life balance. The entrepreneur learning (often the hard way) how to manage money, motivate people, and stay standing after setbacks.

If I could go back and write a letter to my younger self, it would probably be 30 pages long and mostly bolded in red ink. But since I only have a newsletter’s worth of space, here are just a few things I’d include:

1. Learn the rules of the game before you try to change them. Whether it’s how a mortgage works, how compound interest builds, or how companies actually make money—get the basics down. Don’t outsource your understanding of the things that affect your freedom.
2. The first version of anything—your resume, your pitch, your career—is just a draft. The magic isn’t in the launch; it’s in the refining. Don’t get discouraged when something isn’t perfect. Adjust. Iterate. Move.
3. You’ll never regret asking the extra question. Curiosity will always take you further than charisma. Learn to listen. Really listen. It’s amazing what people will tell you if you’re not just waiting for your turn to talk.
4. Money can solve problems—but only wisdom keeps them from recurring. Make a budget. Stick to it. Understand that living below your means isn’t scarcity—it’s strategy. Save before you splurge. And yes, buy the insurance.
5. Feedback isn’t failure. You’ll be rejected, criticized, overlooked. It happens to everyone. What separates the good from the great is what you do next. Keep your ego in check and let your curiosity out front.
6. Don’t confuse being busy with being effective. The longer your to-do list, the more important it becomes to focus on the right things. Learn to prioritize. Learn to say no. Learn that rest is part of the job.
7. You are the average of your calendar and your conversations. Surround yourself with people who challenge and inspire you. And spend time on the things that move the needle. The rest is noise.
8. Life is long—but moments are short. Be present. Celebrate wins. Call your parents. Show up to the game. These are the things that matter 20 years from now.

I wrote Hey Dad… as the book I wish I’d had when I was just starting out. It’s for every young adult who’s navigating life without a playbook—and every parent, mentor, or friend who wants to help, but doesn’t always know how.

The book is filled with lessons along with advice from 30 experts in their field—each offering hard-earned wisdom that doesn’t sugarcoat adulthood but also doesn’t make it feel so overwhelming.

It’s also meant to be personalized. There's space to write your own notes, your own stories, your own advice. Because sometimes the most meaningful gift you can give someone is a nudge in the right direction—and a reminder that they don’t have to figure it all out alone.

So here’s my question to you: What do you wish you knew at 18? Or 21? Or 25?

Drop your answers in the comments—whether it’s something you learned from experience, or something you wish someone had told you sooner. Who knows… your lesson might just change someone’s trajectory.

Hey Dad… comes out April 29. If you know a young adult who could use a guide—or a little encouragement—it’s a great graduation gift (especially with your wisdom written inside the cover).

Thanks for reading and for always being part of this community. It means more than you know.