Stick to your lane, bro
The most dreaded words a parent could hear are the words: "What if?"
OK, maybe not the worst worst. "Dad, I'm pregnant" could be pretty bad (depending on their age).
Or, "Mama, just killed a man", unless you're Freddie Mercury's Mother of course.
Or possibly even, "Dad, I've decided that it would be best if I came home and lived with you and Mum for my 20s, 30s and 40s..."
But "what if" is right up there. You know the next 20 minutes of your life are going to disappear trying to explain a completely hypothetical scenario that will never come up and is totally unimportant.
Or maybe that's just me.
And that's just my kids.
But today, I'm going to play "What if" anyway.
What if:
- Usain Bolt had started out as a footballer;
- Michael Jordan had decided on baseball in high-school;
- Kylie Minogue had stayed on TV (if only!);
- David Bowie had stuck to advertising; or
- I had ended up as a singer in a boy band.
OK, OK, I know some things are harder to imagine than others.
But what would that world look like?
Michael Jordan: Hoops or Homeruns?
We all know Michael Jordan as the basketball icon. Six NBA championships, countless MVP awards, and a legacy that continues to inspire generations. But did you know he initially retired from basketball in 1993 to pursue a professional baseball career? He played for the Birmingham Barons, a minor league affiliate of the Chicago White Sox.
But he was shit.
If he'd started with baseball, we would probably never have heard of him.
Was it arrogance that convinced him he could make it in a second sport that others had dedicated their lives to becoming great at?
Or given more time could he have made his 'second career' a success?
Possibly. After all, his work ethic and competitive spirit were legendary.
We'll never know...
Usain Bolt, The Footballer
Usain Bolt isn’t just a sprinter; he’s the sprinter. But Bolt has openly shared that his first love wasn’t track and field—it was Chicken Nuggets.
After McDonalds, it was football (or soccer, depending on where you are).
In 2018, after retiring from sprinting, he trained with a professional Australian soccer team, the Central Coast Mariners.
It was short-lived. He, too, was shit.
Sprinting wasn’t just what Bolt did best; it’s what made him transcend sport entirely. His charisma on the track captured imaginations globally. Could a winger in the Championship have ever done the same?
Unlikely.
Kylie Minogue: Pop Royalty or Soap Star?
Kylie Minogue’s journey to fame began on Australian TV screens in the hit soap opera Neighbours. Her portrayal of Charlene, the feisty girl-next-door, made her a household name. For many actors, that would’ve been enough.
But Kylie wanted more. In 1987, she launched her music career, starting with “The Loco-Motion,” and the rest is history. Hits like “Can’t Get You Out of My Head” cemented her place as pop music royalty.
Now imagine if she’d stuck to acting. Could she have been an Oscar-winning actress instead of a Grammy-winning pop star?
Er, no. Have you seen her acting?!?
But this time, the career pivot was a success. Kylie is a bigger pop star than she ever was an actor.
Arguably, the leap from acting to music isn't such a big switch, though. Both of them depending on looks and charisma far more than talent.
David Bowie: Ziggy Stardust or the Next Big Thing in Advertising?
David Bowie was destined for greatness, but in an alternate timeline, he might’ve been pitching products instead of music. Before he became the icon of glam rock, Bowie worked in advertising.
It’s not hard to picture him excelling in that world. Bowie was a master of reinvention, storytelling, and image-making—all critical skills in advertising. But would he have had the same cultural impact as an ad exec? Probably not.
Bowie’s genius wasn’t just about creativity; it was about connection. His music spoke to people who felt like outsiders, giving them a voice and a sense of belonging.
Advertising might’ve showcased his creativity, but it wouldn’t have unleashed his full power to inspire and unite.
What Do These Stories Tell Us?
So, would these icons have still become famous if they’d stuck with their "alternative" Plan A career? Maybe.
But their fame is unlikely to have reached the same stratospheric levels.
Why? Because their true genius lay in discovering and embracing their calling.
How many of you are stuck in your own “Plan A,” afraid to pivot to something greater?
The stories of these icons are reminders that the road to success isn’t always linear. Sometimes, it takes courage, failure, and a little trial and error to find your true path.
It doesn't matter if you're 25 or 55, the time to act is now. Who knows? You might just be one pivot away from finding your own true calling.
Until next time, keep chasing your passion
Jon "Westlife" Kaye
P.S. I released a new track yesterday, called "Unspoken". On my path to finding my own true calling, be great if you could give it a listen, save it and add it to your favourite Spotify playlist. It really helps.
Original newsletter disclosures
DISCLAIMERS & DISCLOSURES This content is for education and entertainment purposes only. Jon does not provide tax or investment advice. The information is being presented without consideration of the investment objectives, risk tolerance, or financial circumstances of any specific investor and might not be suitable for all investors. Past performance is not indicative of future results. All investing involves risk, including the possible loss of principal.