Roll the Dice - Career Growth Mindset

Being British, we often carry a natural tendency to hesitate, weigh things up, and hold back until the timing feels just right. That’s where the self-deprecating humour and cautious mindset sometimes get in the way. Contrast that with the never-say-die optimism we often see in American culture, and it’s easy to understand why they seem more willing to take a leap.

The quote, “Rolling the dice doesn’t guarantee a win, but it does get you in the game,” resonates deeply with this. It’s a reminder that while success isn’t guaranteed, taking a chance is the only way to give yourself the opportunity to do so.

I noticed the above quote from an American Entrepreneur - Brad Lea.

It's the attitude him and many others have applied to their life and career, and to great success.

I wanted to explore this further and how it could change your career prospects for the better.

The Trap of Waiting for the Perfect Time

One of the biggest challenges I’ve faced is waiting for the “right” time to take the plunge. It’s why it took me over six years to start my own business. The truth is, the timing never feels perfect. There’s always a reason to put it off—another project, another milestone, another excuse to stay where you are.

The problem is, those six years can turn into ten. Then twenty. And before you know it, you’ve forgotten what the dream was in the first place. Time isn’t infinite, and life has a funny way of slipping by when we don’t act.

Sometimes, you just have to bite the bullet and go for it—whether that’s starting your own business, changing careers, taking a course, or asking for a promotion. The time is now.

The Power of Taking a Risk

When I think about the future—when I’m older and greyer (currently getting older, and yes, greyer)—I want to be able to look back and say, I gave it a go. I want to remember the times I rolled the dice, took a risk, and tried something new. Sure, I’ll remember the wins, but I’ll also remember the lessons learned from mistakes.

Every chance you take, whether it’s a success or a stumble, becomes part of your story. It shapes your path, builds resilience, and often leads to unexpected opportunities. At the very least, you’ll have better stories to tell and a more fulfilling life.

How to Get in the Game

1. Accept That the Timing Will Never Be Perfect There’s no “perfect” moment to take a chance. Life will always have uncertainties, and waiting for the stars to align could mean waiting forever.
2. Start Small Rolling the dice doesn’t always mean a massive life overhaul. It could be as simple as starting a side project, signing up for a course, or reaching out to someone for advice.
3. Focus on the Bigger Picture When fear or doubt creep in, think about how you’ll feel years from now. Will you regret not trying? More often than not, the answer is yes.
4. Learn from Every Outcome Not every risk will pay off, but every risk will teach you something. Even mistakes are valuable when they help you take a smarter chance next time.
5. Time is not Infinite - Not to sound morbid, but this is perhaps the most important point. Life moves quickly, and the sooner you start taking chances, the more you’ll make of the relatively short time we have to create, grow and achieve.

Final Thoughts

Occasionally, a phrase stands out amidst the noise, and for me, “Rolling the dice doesn’t guarantee a win, but it does get you in the game,” is one of those. It’s a powerful reminder that taking action, even when the outcome is uncertain, is the key to growth, progress, and fulfilment.

When you’re older—much older—you’ll want to look back and see a life filled with bold moves, lessons learned, and achievements earned. The stories you’ll tell won’t be about the times you played it safe; they’ll be about the times you took a chance.

Of course, this doesn’t mean being reckless. Everyone has responsibilities that need attention, and it’s important to consider them. But as I said earlier, there’s rarely a perfect time—there’s just now.

So, roll the dice. Get in the game. Your future self will thank you.

Best,

Richard

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