20 Things I’d Tell My 25 Year Old Self

Kit Bobko
5 min readMar 13, 2020

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Photo by Tobias Tullius on Unsplash

I recently turned 50, which is a milestone in anyone’s life. It’s old enough that it sounds weird to say it out loud.

It’s also an age where, whether you like it or not, you realize that there’s likely more track behind you than lies ahead.

So I thought I’d write down things that if I could, I would tell a 25-year old Air Force Captain Patrick K. Bobko, who was then stationed at Shaw Air Force Base, in Sumter, South Carolina.

These are the 20 things I came up with:

  1. You are the limiting factor in your own life. There are many things you aspire to be, and do, and without exception you alone are the reason you will either be or do those things. You are also the reason you will not.
  2. Don’t wait for people to tell you that you are good enough because if you do you’ll be waiting for a very long time.
  3. Start before you’re ready. Whether it’s going back to Graduate School or running a marathon, you’ll never be smarter, taller, fitter, or have more time to do whatever it you’re thinking about doing than right now. Stop preparing to do it and just go do it. You’ll surprise yourself.
  4. Learn to drink whisky. It doesn’t matter if it’s Irish, Japanese, or the single malt Scotch variety, a young man should have an idea about whisky. There will be a moment in your life when you’ll be with a prospective business partner, a date, or just killing time at the hotel bar when the bartender will lean in and ask what you’re having. All of the people I just mentioned will pay attention to what you say, and each will be impressed in different ways by a man who knows a little bit about his booze.
  5. And buy the good stuff. You really can taste the difference between Jack Daniels and a 21-year old Hibiki Suntory.
  6. Pay attention to who your friends are. Somebody once said that you are the average of the four people with whom you spend the most time, so make sure to spend that time with people whose lives are on an upward trajectory. That doesn’t mean the people who are making the most money; it means people who have an internal purpose that propels them. You know who these people are.
  7. Nobody gives a tinker’s damn what kind of car you drive. Not your bosses, your friends, or the guy who pulls up next to you at a stoplight. Contrary to what they think, the 25-year old with the sparkling-new BMW or Mercedes doesn’t announce “success,” it loudly proclaims “lease.”
  8. Put the money you don’t spend each month on that BMW into a Roth IRA instead. The interest that accrues on that money you didn’t spend will give you much more joy than any car you drove 10 years ago. Compounding interest is a mathematical miracle and you should gift that miracle to yourself.
  9. Take vacations. At least 2-weeks off every year. You don’t think you need to because you’re young, but you do.
  10. Whenever your Dad takes the time to talk to you about money or women, listen. There are countless ways to make mistakes in these two areas of life and he’s passing on knowledge he accumulated the hard way. But don’t worry, no matter what he says, you’ll figure out your own unique ways to screw up with both.
  11. Listen to the little voice. It’s the one in your head that tells you to pass on the after-dinner drinks when you have to give an 8:00 a.m. presentation at work the next day, or to do more research on that job offer because something about the guy who interviewed you seems a little off-kilter. You have to really listen because the little voice typically speaks softly, but it’s almost always right. Over the coming 25 years I promise there will be countless times you will look back over the smoking wreckage of some self-induced calamity and think to yourself, “Damn, what the hell was I thinking?” Whatever it was you did was against the advice of the little voice. Don’t do those things.
  12. Know that you are currently worried about a whole litany of things that seem unbelievably important that don’t matter a solitary whit. You’ll soon look back and laugh that these things were ever a concern at all, if you even remember them.
  13. Send handwritten notes. Not e-mail. Not drugstore cards. Actual handwritten notes on nice stationery. There is something uniquely personal about receiving a note from someone in their own hand that they took the time to send. Make it a habit. You’ll be surprised at how many people will mention your note the next time you see them.
  14. If you want something, don’t be afraid to ask for it. Whether it’s a job, an upgrade on a cross-country flight, or to see if a restaurant can put a scoop of vanilla ice cream on your dessert, the only way to find out is to ask. If you do it nicely, with a smile, you’ll be surprised on how many times the answer will be “Yes.”
  15. Talk to your parents. Call them whenever you think about them.
  16. Network more. It’s not a coincidence that the guy with the 2.3 GPA somehow landed the job that everyone else dreams about. Being a person other people simply want to be around is maybe the most valuable thing in the world. Be likable. Smile more. Make an effort to take a genuine interest in other people’s lives. You will learn that as you move further away from graduation that where you went to school and how you did there will matter less and less, and the people whom you know who like you will matter more and more.
  17. Have a plan for the future and use it the way a hiker uses a compass. It should keep you pointed in the right direction, generally.
  18. Go buy a nice made-to-measure suit. Spend more than you think you can afford and make sure it fits correctly. Make a point to wear it. Like it or not, when you walk into a room in a well-tailored suit people will assume certain things about you that will always work in your favor. You’ll look nicer in pictures, too.
  19. Work hard away from the ball because people notice. You’ll never get cut from the team because you play too much defense or rebound too much.
  20. You are going to experience many, many failures. Lots. A handful will be absolutely crushing and some of them will be completely unexpected. Know that each of these failures will lead to something else and often the path that reveals itself in the wake of the initial wipeout will take you to a new place you could not have imagined. It’s ok to be disappointed when you work for something that for whatever reason doesn’t come to pass, but keep in the back of your mind that other opportunities will present themselves. If you focus on the thing you didn’t get, you’ll miss them.

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Kit Bobko
Kit Bobko

Written by Kit Bobko

Lawyer | Veteran | Former Hermosa Beach Mayor | Start-up Founder | Author of Nine Secrets for Getting Elected - www.KitBobko.com

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