What if the promotion you didn’t apply for, the business you didn’t launch, or the truth you didn’t speak… becomes the thing you regret most, not because you failed, but because you never tried?
Let’s get real.
We’ve been taught to fear risk like it’s a career-ending monster. But here’s the plot twist: regret is sneakier, stickier, and far more soul-sucking in the end.
The Risk Myth: “Play it safe and you’ll be fine.”
Nope.
Playing it safe might keep your LinkedIn profile clean and your inbox manageable…but it rarely leads to legacy.
Risk, on the other hand, is messy. It’s vulnerable. It’s the moment you say, “I don’t know how this ends, but I’m doing it anyway.”
And that’s where the magic lives.
We need to Remember:
Regret doesn’t come from failure. It comes from inaction.
From the “Woulda, Shoulda, Coulda” loop that plays in your head when you see someone else living the life you talked yourself out of.
And when regret shows up, it’s formative. It doesn’t knock, it settles in. And once it does, you can’t rewind.
Real Talk from the DaBoss Frontlines
I’ve seen executives pass on dream roles because they didn’t feel “ready.”
I’ve watched brilliant minds stay silent in meetings because they feared being “too much.” And I’ve coached leaders who finally took the leap, launched the business, moved provinces, spoke their truth, and said the same thing:
“I should’ve done this sooner.”
How to Choose Risk Over Regret (Without Losing Your Mind)
- Start small: Say yes to the stretch assignment. Speak up in the next meeting. Post the bold thought on LinkedIn.
- Build bounce-back muscle: Failure isn’t fatal. It’s feedback.
- Surround yourself with actual risk-takers: People who challenge you, cheer for you, and remind you that playing small isn’t your style.
- Ask this question often: Will I regret not doing this a year from now?
If the answer is yes, you already know what to do. Jump. Take the Risk!
Final Word from DaBoss
Your career isn’t a checklist. It’s a legacy. And legacies aren’t built on comfort; they’re built on courage.
So take the leap. Risk the thing. Say the words. Launch the idea.
Because regret rewinds the same old story. While risk writes a new one.
Connect with DaBoss Consultants Inc today, if you are looking for more insights, hiring, employment coaching or training: info@dabossconsultants.ca or (289) 409-8344.
