An Open Letter From My Driver’s Seat

I’m sitting here in my 2002 Acura MDX, atop a large plateau overlooking the Northumberland Strait outside of Inverness, Nova Scotia. My odometer reads 338,814 km and the “check engine” light has been on since I left Calgary. It’s 9:29pm on Wednesday night. While I’ve felt more comfortable at many other points of my life, I’ve never felt more "all in" than I do right now. I’m exactly where I need to be.

I turned in the keys at my corporate job in Calgary exactly 69 days ago with an employer that treated me well since I graduated from university. This wasn’t "just a job" where the opportunity cost of leaving was minimal. It was a career path where I had forged many great relationships along the way and took on many roles within the company. Had I stayed for another year or two, I would’ve been making a six-figure salary; a benchmark figure that many university graduates aspire to, including myself.

Nothing was wrong with my job; however, it just wasn’t for me anymore. I wanted more skin in the game. Making $100,000 in exchange for “putting in your time”, “waiting your turn”, or "going through the motions" is one thing. Captaining your own ship is another. I’m in the midst of attempting the latter.

In the two months since leaving, it hasn’t been easy or comfortable in any sense of the matter. A romantic relationship has fallen by the wayside. I’ve made less money the last two months than I earned in a week in my corporate job. I drove 5,294 kilometers across Canada solo and currently find myself living out of my car for the week (until my June accommodations kick in this weekend).

But let me be clear, this is not a letter to make you feel pity for me. This is a letter meant to inspire you; kick your passions into full gear and pursue them!

If you’re sitting at a screen thinking about all the reasons you can’t leave your job/bad relationship/whatever situation that is holding you back from a passion project or dream you’ve always wanted to pursue, I’m calling your bluff. So would my friend, Chris, who unbeknownst to him, is the person that inspired me to go all in and embark on this journey. Thanks for the inspiration, Chris.

I moved to Inverness, Nova Scotia (a seasonal town of ~1500 people on the coast of Cape Breton Island) this summer for three reasons: a) to caddie at Cabot Links & Cabot Cliffs and b) take action on some personal real estate endeavors and c) meet a ton of interesting people from all walks of life on the golf course and in the local pub and coffee shop.

The golf season officially kicks off into full gear this weekend and I will earn my living off the tips I receive from caddying. It is as direct drive as one could desire. Zero guaranteed money but an infinite ceiling on the high end if you work your tail off.

The funny thing about this whole journey is that while it’s been incredibly uncomfortable at times, its also been very enriching. There’s nothing more raw, yet motivating, than waking up and realizing that the only person you have to depend on is yourself. Society doesn't provide you with a handbook telling you where you need to be every morning and the things you need to be doing. It takes initiative, discipline, perseverance and commitment to your craft. By necessity, I have to make new friends every day, hustle day in-day out for my compensation on the golf course, take care of my body (which is more difficult than you think looping 36 holes a day of links golf 6 days a week), and stay ahead of the curve on real estate opportunities. Bundled together, I deem this “chasing down a dream”.

That’s really what it is… I can’t totally articulate what my dream is but perhaps that’s the beauty of it. The element of the unknown. I know I’m on a path somewhere, I just don’t know where exactly it is leading.

There is a famous John Maynard Keynes quote that reads “worldly wisdom teaches us that it is better for reputation to fail conventionally than to succeed unconventionally.” However, ever since a certain conversation on this very subject took place five years ago with a favorite professor of mine, Dr. Rick Nason, I’ve approached my life differently and frankly, this Keynes quote has scared the bejeebers out of me ever since. I’ve changed the wording of it to read “I’d rather risk failing while trying to succeed unconventionally than failing to try and living my life conventionally.” Thanks for this memorable conversation, Rick.

My goals look very different than they were three months ago, yet alone a year ago. Namely, taking action on a few real estate initiatives, to caddie over 150 rounds this summer, qualify for the Canadian Amateur Golf Championship, qualify for a Canadian PGA Tour event here in Cape Breton, and put the pieces in place for my next big professional endeavor.

We’ve all heard the stories about Steve Jobs eating at the Hare Krishna temple so he could get one good meal a week or Elon Musk living out of his office on $1 dollar a day and showering at the local YMCA around the corner. Surely these two gentlemen didn’t know exactly where they were going to end up at the time, and by no means am I insinuating that I will have a similar impact on the world as these two pillars of humankind, but I am saying there is something to be said for going all in. It takes a great deal of conviction, sacrifice and gathering your cojones.

This week, almost by fluke, I caddied for a really nice 13-year old kid from New Hampshire who had a nicer golf swing than I’ll ever have. I received an e-mail from his mom a few days later that her son thoroughly enjoyed his Cabot experience and a picture she took of us is now the background on his phone. It was my favorite loop of the year and hearing this made my week, not just day!

If experiences like this continue and I keep putting myself in positions ripe with opportunity, I have faith good things will happen. A good friend of mine, Will, sent me a text message a few days ago that meant a lot to me. He said, “Mike - I meant to tell you that everyone I know that’s done what you’ve done has ended up in a better spot than before they began the adventure.”

I have no idea where the dots will connect for me but I do know I need to be ready for my 10:48am loop in the morning.

Mike

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* For the record, I’m not against the corporate world. It is the backbone of a functioning society that provides for its people. But the reality is that it is not for everyone and/or sometimes you have to take a break from it. If you’re currently in your dream position, that's amazing and I’m genuinely happy for you. Be grateful for that feeling and take solace in the fact that you have that much conviction about your path forward at a young age.

** I did actually write this from the driver’s seat of my car.

*** If you liked what you read and want to follow along, you can check out more of my published headspace at www.mikesmailbag.org.