Leap Anyway. Taking Risks Creates a Life Worth Remembering
“In the end, we only regret the chances we didn’t take.” — Lewis Carroll
When people look back on their lives, it’s rarely the failures that haunt them. It’s the missed opportunities. The dreams deferred. The conversations never started. The adventures never taken.
A growing body of research supports this deeply human experience. A study from Cornell University found that our biggest regrets tend to come from not pursuing our ideal selves—what researchers call “the road not taken” (Psychological Science). We regret the risks we didn’t take far more than the ones we did.
Why? Because inaction lingers. It leaves us wondering “what if?”—without the clarity that action (even imperfect action) brings. The good news? It’s never too late to change that narrative.
Whether you’re 30 or 90, you can still make bold, aligned choices that lead to a life of purpose instead of a list of regrets. Here’s how to reframe risk, trust your instincts, and design a future your future self will thank you for.
1. Understand the True Cost of Playing It Safe
Avoiding risk may feel comfortable, but it can slowly erode your sense of vitality. As we age, it’s easy to mistake routine for security. But too much “safety” can lead to stagnation—mentally, emotionally, and spiritually.
Research from The Journal of Personality and Social Psychology shows that people who live too cautiously often experience lower life satisfaction and higher levels of “existential regret” in later life (JPSP).
Action Step: Make a list of “safe choices” you’ve made that still leave you wondering. Which one might you revisit—with new courage and wisdom?
2. Redefine What “Risk” Really Means
Risk doesn’t always mean skydiving or quitting your job. Sometimes it’s emotional: starting therapy, saying “I love you” first, or launching a new project at 70. Risk is about choosing growth over comfort—and alignment over approval.
“You don’t have to leap off cliffs. You just have to step out of the shadows.”
Try thinking of risk as an investment in your future clarity. Even if it doesn’t go as planned, you’ll gain experience, wisdom, and confidence.
Action Step: Reflect on one area of your life—health, career, relationships, creativity—where fear has been holding you back. What’s one small, brave action you can take this week?
3. Learn from Those Who Regret—and Choose Differently
Author and palliative nurse Bronnie Ware famously shared the five biggest regrets of the dying. At the top of the list? “I wish I’d had the courage to live a life true to myself, not the life others expected of me.” (Bronnie Ware: Top 5 Regrets)
That insight is echoed by thousands of people across age groups. We long to be bolder, more authentic, more expressive.
Action Step: Write your “anti-regret list.” What are five things you’d deeply regret not doing? What’s stopping you—and how could you begin?
4. Reframe Failure as Data, Not Defeat
We often avoid risk because we fear failure. But in reality, failure is feedback. It gives us new information, builds resilience, and opens unexpected doors. Most successful people didn’t avoid mistakes—they embraced them.
A study in Harvard Business Review found that people who frame setbacks as part of growth are more likely to persist, adapt, and ultimately succeed (HBR).
Action Step: Revisit one past “failure.” What did it teach you? How can you apply that lesson now?
5. Use Tools to Practice Brave Decision-Making
Fear often clouds clarity. But decision-making frameworks can help you choose courage over comfort with confidence. Try:
- WOOP (Wish, Outcome, Obstacle, Plan) from Gabriele Oettingen
- The 10/10/10 Rule: How will this choice feel in 10 days, 10 months, and 10 years?
- Journaling apps like Day One to reflect on daily choices and align with your values
Action Step: Pick a small but meaningful decision you’ve been delaying. Use one of these tools to work through it, and take a step forward.
6. Surround Yourself with People Who Encourage Boldness
Taking risks is easier when you have people who believe in you. Surround yourself with encouragers, not naysayers. Find a mentor. Join a mastermind group. Or lean into platforms like GetSetUp to learn alongside other purpose-driven adults.
Action Step: Reach out to someone who’s taken a risk you admire. Ask them: What did it feel like before and after? What do you wish more people knew about choosing boldly?
7. Let This Be the Chapter Where You Choose Differently
It’s easy to assume that big changes belong to the young. But boldness is ageless. Whether you’re 55 and pivoting careers or 75 and finally writing that memoir, remember this:
“You are never too old to become who you might have been.” — George Eliot
Your next chapter can be bold, curious, loving, liberating—and uniquely yours.
Action Step: Write a note to your future self 10 years from now. What will you be proud you started today?
What’s one risk you’re glad you took? What’s one you’re ready to take now?
Join us in the Age Brilliantly Forum and share your bold vision—or your quiet first step. Let’s inspire each other to trade regrets for real experiences, and live intentionally at every age.
We want to hear from you:
What’s a risk you’ve been contemplating lately?
What held you back before—and what’s changed?
What would your 90-year-old self thank you for doing today?
Let’s talk about it in the forum. You’re not alone—and your next brave move might inspire someone else’s.