Ten Things I Wish I Could Tell My 23 Year-Old Self


1. Being hurt by a woman (or by multiple women) doesn’t give me the right to pay that hurt forward in future relationships. It is hard to keep being vulnerable, but you have to. There are good people out there who want to love you, warts and all.
2. Enjoy now. Appreciate what you have. Stop running.
3. Talk to your family. They want to help you. Really. Open up and trust them.
4. Start playing basketball. It’s fun, and you will be thankful for those years of practice in a few years. Actually, can I just tell my 10 year old self to keep it up through high school?
5. Dressing like a hippy is cute for a while…but please: buy clothes that fit!
6. Don’t get into debt. Never get to a place where you are relying on credit. Get your finances together early and avoid heartache later on.
7. If you can, buy property in the city.
8. Don’t worry about social obligation. Don’t worry about status, or impressing people.
9. Your metabolism will slow down soon. Eat better. Exercise. Start biking.
10. Take a moment to appreciate the people in your life right now. Your life may change drastically, and you may lose contact with many of those people.

With thanks to idatedthatdouche.com for the inspiration.


Photo courtesy of Flickr/pursanovd

About Josh Bowman

Josh Bowman is a professional fundraiser, story-teller, comedian, and blogger. He has worked and consulted in Vancouver, New York, and now Toronto for almost a decade. Josh improvises around Toronto, including regular shows with Opening Night Theatre, and also blogs for the Huffington Post. You can email Josh here.. If you want to know more about Josh, check this post and this post out first.


  1. Richard Aubrey says:

    Jeff WTF WFT?
    If directed at me. I was a fraternity grad adviser back in the day, loosely affiliated with the Dean of Students’ office. I was a semi-professional watcher, listener, and talker-to, with people thinking I was the one to come to….
    I knew of a number of cases where women were trying to get a guy’s attention and he wasn’t seeing it. He didn’t reject them. He didn’t avoid them. He didn’t hear them. He heard, as I say, compliments.
    Now, since a compliment could be construed as an invitation to show some initiative, I presume a woman would be careful with it, not bestowing it where it might start something she didn’t want. Therefore, it’s probably worth presuming a bit of initiative might be in order, whichever way it turns out.
    This was going on half a century ago where women didn’t overtly initiate, but had a suite of behaviors which were supposed to work. Compliments and personal pleasantries were up the ladder a ways, so taking them as a “message” wasn’t a long bet.

  2. WFT? That was stupid…

  3. Richard Aubrey says:

    When a woman is being particularly kind/pleasant/cheerful/complimentary toward you, she may not be being kind/pleasant/cheerful/complimentary. She may actually like who you are. Big surprise, I know.
    But, having put herself out there, she can’t very well object if you try to find out what’s actually happening, so give it a shot. Carefully.

  4. Not buying iti says:

    Life is what you make of it, personal freedom & choice is the basis of happiness.

    1- marriage & common law are extremely risky proposition for a male even with a pr-nup, avoid both until 40something.
    2- yep say No more often & avoid being coerced into chivalrous behaviour by traditionalist or worse the politically progressive.
    3- your first hunch is usually correct.

  5. 6, 7, and 8 are contradictory tough nuts, collectively considered.

    They seem like a recipe for waking up at age 46 and ditching all the things you strove for in an attempt to recapture that lost freedom. And then you’ll want a cookie for being in touch with your feelings.

  6. (1) “Just say ‘no’ more”

    (2) ” Just say that you want orange soda, instead of ‘whatever'”

    (3) “Maintain your boundaries…maybe the ‘friend’ is really a ‘frenemy'”

  7. Joanna Schroeder says:

    Mine would be, “Don’t be so afraid of heartbreak and being alone.”

  8. Where were you 20 years ago?!

  9. Tom Matlack says:

    Great list. I would add (for me) “Don’t be so scared all the time, of people, of failure, of what is going to happen next”

  10. “There are good people out there who want to love you, warts and all.”

    If only that were remotely true, my life would be infinitely better.

  11. Definitely a good list – I’m glad to come across it so close to 23 :).

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