What is something I wish I could tell my 20-year-old self?
Well, the first thing I’d do is hand him $4,000 and say, “Put $2,000 in Apple and $2,000 in Microsoft. Then try very hard not to sell it when you need pizza money.”
Then 59-year-old me would step back into the present, check the balance, and enjoy the roughly $13 million that little bit of time-traveling financial wisdom would have produced.
That would be my first choice.
Possibly my second, too.
But if we are not allowed to use time travel to manipulate the stock market and retire comfortably, then I suppose I’d have to go with actual advice.
I’d tell 20-year-old me to stop worrying so much about what other people think.
That sounds simple, but I don’t mean it in the usual refrigerator-magnet way. I’m not saying other people’s opinions don’t matter. They do. There is wisdom in seeking counsel. There is value in listening to people who have walked farther down the road than you have. There are times when someone outside your own head can see things more clearly than you can.
But there is also such a thing as taking advice from the wrong people.
And I did a lot of that.
When I was younger, I gave other people’s opinions far too much authority over my own life. I didn’t just listen to advice. I let it steer. I let it decide. I let it close doors I had barely even knocked on.
That was especially true with relationships.
There were girls I didn’t ask out because friends told me not to. There were girls I didn’t ask out because I imagined my friends would tell me not to. I spent a lot of time worrying about how things would look, what people would say, whether I would be laughed at, whether I would seem foolish, whether someone else might think I had made a bad choice.
The result was that I made plenty of bad choices by making no choice at all.
One of my friends back then — and I mean girl friends, not girlfriends, because that would imply a much more impressive social life than I actually had — was a girl named Jamie.
Jamie and I had gifted English together. She was cute, smart, fun to talk to, and we were getting pretty close. There was only one problem.
I was an idiot.
Jamie was a swimmer, which meant she had broad shoulders and looked strong. She probably was strong. Possibly stronger than me, which, looking back, was not exactly clearing a high bar. But some of my friends told me I shouldn’t go out with a girl who could beat me up.
And because I was 16 and apparently outsourcing my romantic decisions to the Council of Morons, I never asked her out.
Then I moved before my senior year, and that was that. No date. No awkward teenage movie night. No funny story from a school dance. Nothing.
I haven’t talked to Jamie in a long time, but I’ve seen enough from a distance to know she seems to be doing great. She still swims. She still looks beautiful. She seems to have built a good life. I don’t pretend some high school dating relationship would have turned into anything permanent. Most don’t. But we probably would have had fun. We probably would have made some good memories.
And that alone would have been worth telling my friends, “Thanks, but no thanks. I’ll decide this one for myself.”
That’s the kind of thing I wish I had understood earlier.
Not every decision in life has to be approved by committee. Not every instinct needs to be run through a focus group. Not every possibility needs to survive the opinions of people who are mostly just talking because talking is free.
There is a difference between wise counsel and random commentary.
Wise counsel usually comes from people who have wisdom, experience, courage, humility, and something worth imitating. Random commentary often comes from the guy sitting next to you who has no more idea what he’s doing than you do, but says it louder.
When your buddy who spends every night watching television and playing games on his Commodore 64 tells you the girl you like is weird, maybe you should go out with the girl and find out for yourself. He can look in the mirror later and ponder the true nature of weird.
I’m not saying I wish I had ignored everybody. That would have been terrible advice, too. Twenty-year-old me did not need less guidance. He needed better filters.
He needed to learn who had earned the right to speak into his life.
He needed to understand that some people give advice from wisdom, and some people give advice from fear. Some give advice because they love you. Some give advice because your courage makes them uncomfortable. Some people want to protect you from danger. Others just want to protect themselves from having to watch you try something they were too afraid to try.
That doesn’t only apply to dating.
It applies to work. It applies to leadership. It applies to creativity. It applies to faith. It applies to almost every meaningful decision you make.
I spent too much of my young life trying to avoid looking foolish. The problem is that almost everything worth doing carries at least some risk of looking foolish. Asking someone out. Applying for the job. Speaking up. Leading. Writing. Trying. Failing. Trying again.
You can avoid embarrassment by doing nothing. But doing nothing has its own cost. It just sends the bill later.
So if I could talk to 20-year-old me, after giving him the Apple and Microsoft stock tip and begging him not to waste it on a used Camaro, I’d tell him this:
Listen to wise people. Respect good counsel. Be humble enough to know you don’t have all the answers.
But do not hand the steering wheel of your life to people who are not going where you want to go. Do not let people who are not living your life make your life smaller.
Ask the girl out. Take the chance. Try the thing. Make the decision.
And if the Council of Morons objects, thank them politely for their service and keep walking.
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Copyright © 2026 Doug DeBolt.
