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When Your Why is Wrong: A Cautionary Tale for Millennials

  • colinrgbishop
  • Jan 1
  • 3 min read

I’m the son of two incredibly hardworking boomers who started with nothing and built a life they could only dream of. My dad, one of six siblings raised in a two-bedroom council house in the Midlands, told me he would walk the long way home so his friends wouldn’t see where he lived. My mum had an equally challenging childhood, raised by a single mother in Blackpool. Together, they worked tirelessly to provide my sister and me with the life they never had—a safe, middle-class upbringing filled with opportunities.

This story is familiar to many boomers who clawed their way up from nothing after the war. For their generation, success was about providing stability, security, and opportunities for their children. Their why was clear, heartfelt, and deeply rooted: to give their families what they never had.

But the waters got murkier for millennials like me, raised in comfort and opportunity.

The Millennial Trap: When Money Becomes the Goal

Growing up, stories of vast fortunes being made in the city were everywhere. The mantra of "success equals money" was passed around schoolyards, parent gatherings, and media. For parents who had worked so hard to escape poverty, money was seen as the solution to everything.

So, millennials set their sights on finance, tech, and the "gold rush" industries. Business degrees became the default choice for those unsure of what they wanted. Finance and insurance companies dangled ballooning salaries like golden carrots, luring us into the fold.

But here’s the reality:

  • Early retirement is like making it in the Premier League—millions dream it, only a handful achieve it.

  • The more you earn, the more your lifestyle expands to fill (and exceed) your income.

And when money is your why, it’s a shallow motivator. Enough is never enough.

The Wrong Why: My Own Experience

For years, my why was simple: make money. I didn’t realize how toxic that why was until I was deep in the grind, chasing goals that left me feeling empty.

My parents’ why—providing a better life for their family—was noble and fulfilling. But for many millennials, raised in relative comfort, the fire wasn’t about never going back. It became about more: more watches, more cars, more stuff.

Rethink Your Why

If your why is rooted only in material goals, it’s unlikely to bring lasting happiness. Research shows true happiness isn’t tied to money, fame, or popularity. These are fleeting victories, not deep fulfillment.

Ask yourself:

  • Is your why bigger than you?

  • Does it serve your family, your community, or the world?

  • Will it bring you joy even on the hardest days?

When your why is meaningful, every step toward it becomes fulfilling.

How to Build a Better Why

  1. Start With Health: Without your health, you can’t be there for anyone else. Make it a priority.

  2. Make Time for People You Love: Connection is the heartbeat of life. Don’t sacrifice it for fleeting goals.

  3. Focus on Impact: Structure your why around positively impacting others.

Money is a tool, not the destination. Build a life that uses it wisely, but don’t let it define you.

Final Thoughts

Life is precious, and the thrill isn’t in hoarding wealth—it’s in the moments, connections, and joy you create along the way. Be brave enough to ask yourself, What is my why? If it’s not deeply rooted in something meaningful, now is the time to recalibrate.

You can live a life that impacts others profoundly while also bringing yourself happiness and fulfillment every day. Don’t wait until it’s too late to figure that out. Make the corrections now and set your sights on a why that truly matters.


 
 
 

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