No More Regrets: How to Bet on Yourself and Live Without 'Shoulda, Woulda, Coulda'
The Biggest Regrets of the Dying: Lessons from Those Who Wish They Had More Time
When people are on their deathbed, their regrets are rarely about the things they tried and failed at. Instead, the deepest regrets stem from acts of omission—the things they didn't do. Bronnie Ware, a palliative nurse who worked closely with the dying, identified some of the most common regrets:
"I wish I had the courage to live a life true to myself, not what others expected of me."
"I wish I hadn’t worked so hard."
"I wish I had expressed my feelings."
"I wish I had stayed in touch with my friends."
"I wish I had let myself be happier."
At the core of these regrets is fear—fear of failure, rejection, or stepping outside of what’s familiar. Most people know what they truly want but hesitate to take action. The question is, why? And more importantly, how can you break free so you never look back with regret?
Understanding Fear: Why We Avoid the Things We Truly Want
The Psychology of Fear and Avoidance
Fear is a survival mechanism designed to keep us safe. But in today’s world, it often holds us back from what would actually improve our lives. Two major psychological phenomena play into this:
Loss Aversion: We fear losing something more than we value gaining something. So, even if success is possible, we stay where we are because failure feels more painful.
Familiar Hell vs. Unfamiliar Heaven: Even if our current situation is stressful or unfulfilling, it’s predictable. The unknown—even if it holds better opportunities—feels risky, and our brains are wired to avoid uncertainty.
The Fear of Success
It may seem counterintuitive, but success itself can be terrifying. Achieving what we truly want means:
New responsibilities and expectations
Increased visibility and scrutiny
Leaving behind old identities and comfort zones
This fear keeps many people stuck in a loop of playing small, convincing themselves that now isn’t the right time. But if not now, when?
How to Build the Confidence to Bet on Yourself
1. Identify What You Really Want
Many busy professionals have spent years following a career path dictated by external expectations—family, society, financial pressures. To avoid regret, you must get clear on what you truly want.
Reflect on moments of excitement: What activities or goals have made you feel most alive?
Journal your ideal day: If money or obligations weren’t an issue, what would your life look like?
Check for jealousy: Sometimes, envy signals unacknowledged desires. Who do you admire, and why?
2. Reframe Fear as Proof You’re on the Right Path
If something scares you, it likely means it matters. Instead of interpreting fear as a stop sign, view it as confirmation that you're moving in the right direction.
Ask yourself, “What’s the worst that can happen?”
Shift from “I’m scared” to “I’m excited.” Fear and excitement feel the same physically—harness that energy.
Accept that discomfort is part of growth. If you’re never uncomfortable, you’re not evolving.
3. Start Before You Feel Ready
Confidence doesn’t come before action; it follows action. The best way to become confident in something is to do it, even in small steps.
Take micro-risks daily: Send that email. Sign up for the class. Speak up in the meeting.
Create a low-risk experiment: Test your dream in small ways before making a big leap.
Don’t wait for permission: No one will hand you the green light—create it yourself.
4. Eliminate the Illusion of “Perfect Timing”
Life will always be busy. Waiting for the perfect moment means waiting forever. Instead, integrate your dreams into your current reality.
Commit 10 minutes a day: Small, consistent effort compounds over time.
Use habit stacking: Attach your goal to an existing habit (e.g., write for 10 minutes after morning coffee).
Protect your energy: Set boundaries with work and obligations that drain you.
Practical Steps to Avoid Future Regret
Adopt the “Regret Test”
Imagine yourself at 80 years old. Will your current decision make you proud or fill you with regret?
Surround Yourself with Expanders
Spend time with people who have taken risks and succeeded. Their courage is contagious.
Practice “Future Self” Thinking
Act as if you’re already the person who has achieved your goal. How would that version of you behave today?
Normalize Failure as Part of the Process
Every successful person has failed—many times. View failure as data, not a dead end.
Remember: The Only Way to Guarantee Regret Is to Never Try
You cannot fail if you take action. You either succeed or learn. Either way, you win.
Final Thoughts: Choosing Boldness Over Regret
You don’t have to make drastic changes overnight. But you do have to start. Your dreams won’t wait, and neither should you. If you take even one step today toward what you truly want, you are already ahead of most people.
So ask yourself:
What is one small action I can take today that my future self will thank me for?
If I knew I couldn’t fail, what would I do?
The answer is your next move. Don’t wait until it’s too late to live the life you actually want.
Need Help? Living your values doesn’t just change your life—it elevates the people around you.
Authenticity is contagious. Fulfillment is magnetic.
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Article References
The sources cited in the article:
Forbes. "The Art of the Comeback: Building Resilience in the Face of Setbacks." Forbes - The Art of the Comeback
Harvard Business Review (HBR). “Research: Setbacks Can Actually Boost Your Career.” HBR - Setbacks Can Boost Your Career
Harvard Business School. “Thriving After Failing: How to Turn Your Setbacks Into Triumphs.” Harvard - Thriving After Failing
Harvard Business Review (HBR). "The Secret to Building Resilience." HBR - The Secret to Building Resilience
Psychology Today (PT). “New Research on How to Overcome Setbacks.” PT - How to Overcome Setbacks
