Top 40 Under 40

This would have been the title of my novel if I had written one...

Each year, Caldwell Partners International chooses 40 Canadians who were under 40 in the past year to honour for their outstanding achievements. Once again this year, I’ve been excluded from this list. I know it baffles me too!

The problem is, time is running out. I’ll be 40 in July and unless I do something outstanding in the next four months, like broker peace between Israel and Iran, I’m afraid I won’t make the list.

So I’ve come up with a solution. Allow me to present the first ever Project 40, Top 40 under 40.

Of course I’ve nominated myself as the first ever recipient of this prestigious award.

In honour of this historic event, I’ve asked 20-Year-Old Me to interview present day me in this Project 40 exclusive.

20-Year-Old Me: It’s quite an honour to be sitting in front of you right now. You are honestly one of my favorite people in the world. I have so many questions to ask you. This is really exciting.

Present Day Me: Settle down young fella. Ask me any question you wish.

20-Year-Old Me:  Well for the readers let me get some background from you. When and where were you born?

Present Day Me: July 10, 1972 in Toronto

20-Year-Old Me: How long did it take you to write your first book?

Present Day Me: Umm… I’ve never written a book.

20-Year-Old Me: I see that you’re not a pro basketball player?

Present Day Me: Correct.

20-Year-Old Me: How old were you when you first pulled in that multi-million dollar paycheque?

Present Day Me: Umm… well, that has never happened. I won’t say it never will, but it’s not like that now.

20-Year-Old Me: But I thought we were going to be filthy rich by the time we were 40? What happened?

Present Day Me: Hey, I’m doing pretty well. I had some lofty goals 20 years ago but at some point reality sets in and you find the path in life that’s right for you. Everything comes with sacrifice and you have to choose what you are willing to sacrifice in order to reach your goals. The path that would have taken me to the multi-million dollar paycheques required sacrifices that I wasn’t willing to make. My current path allows me time on the weekend with my wife and daughters and provides for a very comfortable life. I’m happy with the career choices I’ve made.

20-Year-Old Me: Okay, so how much do you make?

Present Day Me: Well that’s a very personal question. But, since you are me, I guess it’s okay. I’ll actually write it down. I don’t want to share that information with everyone. [Pass 20-year-old me a piece of paper]

20-Year-Old Me: Okay then, not bad. I can work with this. So you must be living it up, how many times a year are you in Vegas?

Present Day Me: I haven’t been to Vegas and I really don’t party anymore. Not the kind of partying you’re talking about. I remember when I was you, I’d go out every night of the week. I’d never get hung-over and I’d never get tired. I was only responsible for paying my tuition so anything that was left over went to having fun. Now I have two children, a wife at home on extended maternity leave, a mortgage,  car payments and retirement to save for. I don’t have the time, money or desire to party every night. In fact a good night out for me now means dinner and a nice bottle of wine with friends.

20-Year-Old Me: Fine, you grew up, you have responsibilities. I get it. Do you still play basketball?

Present Day Me: Not really, I have a hard time finding time to play. I’d like to join a men’s league next fall.

20-Year-Old Me: Are you serious? Do you even watch basketball on TV any more?

Present Day Me: I try to watch a game here and there. I go to a few games every season but I don’t have the time like I did 20 years ago.

20-Year-Old Me: Wow, I don’t really know you anymore.

Present Day Me: Yes you do. We’re the same person. Remember when we were in the career centre wondering if it would be possible for us to go to graduate school. Well we have a Master’s degree now. And remember when we applied for a million bank internships only to get one interview and not even get that job. Well we’re a Vice-President at that very bank. Oh, and remember when we thought we’d never get married or have children. We have both and we’re very happy. Life hasn’t been a straight line up for me. I see younger people in leadership positions at work. I haven’t become the tycoon I thought I’d be. I haven’t published a novel. I haven’t surpassed my dreams. But when I look back at what I have achieved in my first 40 years I’m very proud of myself. I’ve turned into the man I thought I’d be.

20-Year-Old Me: Okay old man. I have to run and get my hair cut. Wednesday is ladies night at Stages. Can’t miss that.

Present Day Me: Yes, I remember those days young buck. Have fun.


    • Thanks! Good luck, 5 years is a long time… If all else fails you’ll make the Project 40 Top 40 under 40 list. I’d like to get a second crack at it myself… there has to be a Top 50 under 50 list. That’s what I’m shooting for now!

  1. Love this one! So funny how our expectations for ourselves change over the years. But in the end, it sounds like you ended up exactly where you were meant to and are happy!

  2. Love your approach! I know that if my 20-year old self interviewed me, she’d be very surprised at the directions my life has taken. Lots of unexpected detours, t-junctions, roadblocks, and also lots of unanticipated opportunities and memorable moments. Life, and age, are what you make of them, aren’t they? Thanks for visiting my Dream BIGGER blog (and liking it!) You might also be interested in another one I write that’s totally focused on having some fun with the age thing. It’s at

    • Thanks! I do like your fab fifty five blog…. I’ll be sure to follow it. I’m looking forward to getting older and I really like hear stories from like-minded people.

    • Thank you very much! Maybe some day there will be a book… I just don’t have time now.

      I enjoyed reading your blog today… it’s well done.

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