Money Advice for My Younger Self

If I could go back in time and do it all over again with everything I know now, I’d make one helluva 17-year-old.

There’s no question. I’d be at least 10x more successful. Richer. Stronger. Healthier. Better looking. And blah blah blah blah blah.

Of course, I probably wouldn’t appreciate all the knowledge I’ve gained the hard way. Nothing leaves the lasting boot imprint of wisdom quite like the lessons learned from life delivering a good ass-kicking.

Still, it’s fun to think about. If for no other reason to avoid the folly of my own mistakes again. Naturally, by sharing, I hope somebody can get something useful from it without having to experiencing the same setbacks.

A Few Money Tips for 17-Year-Old Me

If I was 17 again, I’d have spent more time brushing up on my own financial literacy. Obviously you don’t know what you don’t know. But I knew approximately jack shit about personal finance coming out of high school. That was a hindrance.

Beyond learning, I’d also lay a strong(er) foundation.

TIP NUMBER 1: I would have held down a job from as early as I could land one. Everybody is a bit happier, more confident, better version of themselves when they have a little jingle in their pocket. But it’s also a good prescription for keeping the right mindset: that we’ve all got to earn our own way.

TIP NUMBER 2: I would’ve set out to become financially independent as soon as possible. I would have cut the proverbial umbilical cord, so to speak, much sooner. You can’t grow up when you’re living in a state of dependency. (Sorry mom and dad. I wish I would’ve learned that one sooner.)

TIP NUMBER 3: I’d have saved at least $1,000 into an emergency fund. This would’ve helped me navigate the unexpected expenses that pop up. Without a ton of anxiety, or forcing me to sell off a kidney every time I needed a spare buck. πŸ˜‰

TIP NUMBER 4: I would not have gone to college. At least, if I did, I would’ve spent even more time working, making money, and attempting to learn useful skills. I definitely would’ve spent even more time reading during this span of my life (and probably a bit less time being a dip shit).

TIP NUMBER 5: I would’ve aimed to save $100,000 before making any major investments. Knowing what I know now, if I’d have realized the power of leverage at a much younger age, this would’ve been huge. It would’ve set me up to have much more optionality – to change jobs, start businesses, travel, or spend my time however I wanted. AND – it would’ve been hard as hell. So the discipline I would’ve needed to develop to do this would have laid a strong foundation of good money habits much earlier.

TIP NUMBER 6: I’d have bought a house and rented it out to cover my own living expenses + generate some income. This is, of course, easier when you’re holding down a job and have some liquid savings. But it’s also a strong financial move in the early innings. Even if you decide to move, you can hire a property manager to keep it fully rented, cover your mortgage, and keep an income-generating asset.

TIP NUMBER 7: I’d have deliberately sought out apprenticeships sooner. Rather than just “jobs” I would’ve pursued opportunities that allowed me to pursue my interested. I’ll pat myself on the back a bit here because I made some very solid moves here between ages 19-25. But I would’ve doubled down on this.

TIP NUMBER 8: I would’ve aimed for clarity rather than credentials. I spent 7-8 years out of high school spinning my wheels. I allowed inertia to carry me through those years. That period truly felt like a waiting game. If I could go back, I would deliberately set out to try more things and cross more options off the list sooner – with the goal to find one or two “career targets” to aim at.

TIP NUMBER 9: I would have prioritized relationships more. Especially with my parents. There were a few years there when I was first getting started that money became a hindrance for going home for holidays or visiting more often. I can always make more money. But I won’t ever get that time back.

TIP NUMBER 10: In the interest of rounding out this list with 10, rather than 9 (because what kind of psycho makes a list of “9 Tips’), here’s one more. I would’ve challenged conventional wisdom more. Instead of listening to the experts, I would’ve investigated more for myself. I would’ve read more books, interviewed more people, and tried more things. Especially as it relates to money. (For instance, I never would’ve started throwing money into “qualified retirement plans” and instead prioritized control and liquidity.)

This is just a small part of a bigger thought experiment I’ve been working on. It’s already been a lot of fun, too.

We would all probably be better off if we could go back and do things over with wisdom we have now.

But that’s the fun of life, right? Trying to navigate through it all with incomplete information.