The "I Can't Believe I Did That" Life
Jun 11, 2026
How and Why the Risks You Never Took Will Haunt You
Are you after a life of deep personal and professional satisfaction? Then default to and prioritize "I can't believe I did that" experiences over playing it safe. This is key.
Taking action to create those moments is about opening yourself up to the new, the novel, and the things you've never done before. The phrase "I can't believe I did that" almost always follows an unorthodox leap of faith — a decision to step well outside your comfort zone. This is what Behavioral Scientist Daniel Pink calls the antidote to Boldness Regret.
Boldness Regret stems from inaction and hesitation. Boldness Regret is the most common, deep, and lingering regret people carry. Doing the risky, the uncomfortable, the unexpected is the cure. Even when an adventure ends in an unexpected or perceived-failure way, you learn, you grow, and you walk away richer for it. Choosing to leap cures the sting and void of "I wish I had."
What about failure?
Most people don't fail because they lack talent. They fail because of fear — and because they stopped before the process was finished. People are so afraid of failing that they count themselves out before they even begin and never go after their big audacious goals.
Those who make things happen get up. And get up. And get up again. That is the bottom line.
How do we overcome fear and naysayers to keep showing up for our goals? Start by reframing fear entirely — not as something to eliminate, but as something to subordinate to what matters more.
When you frame failures as necessary learning opportunities, as reps that make you stronger, you discover that consistent repetition is what separates those who break through from those who quit midway. Every setback produces data — data that informs, compounds, and becomes impossible to ignore. The work may not get easier, but you'll become someone who no longer needs things to be easy.
The 7 Rules of the "Can't Believe" Life
1. Ask who, not what. What kind of person do you want to be? Figure out your true priorities, what actually matters to you, then make sure the ways you spend your time, money, and energy reflect your true priorities.
2. Default to growth and adventure. Fill your life with "I can't believe I did that" moments. Rich, character-building experiences are the direct antidote to Boldness Regret.
3. Break the rules. Arnold Schwarzenegger has long advocated for this — not breaking the law, but breaking the rules. It's impossible to be a true original if you're too well-behaved. Think outside the box, even if it upends a few things and makes people uncomfortable.
4. Frame mistakes as teachers. You won't always win and you won't always succeed — but don't be afraid to decide, act, and sometimes fail. There is no growth without mistakes and no learning without setbacks. Have a vision, learn as you go, and get back up.
5. Ignore the naysayers. People who say something can't be done are usually living lives you don't want. Be the person who cuts a path, finds a way, and makes things happen.
6. Work. Then work some more. Rest and downtime are important, but know that to get where and how you seek to be, there's no substitute for putting in the hours and doing hard work.
7. Be a lifting force for good. Lifting people up in ways both large and small will bring you more satisfaction than virtually anything you'll ever do. Focus on what's good and working. Be grateful and glad, and never underestimate the power a kind word.
Defaulting to Growth and Adventure over Status Quo
Rule #2 deserves special attention. Defaulting to growth and adventure over status quo isn't just motivational language — it's a way of living that delivers deep psychological, personal, and professional benefits. Choosing the novel, the new and unexpected means that even when an adventure is messy or misses the mark, you earn stripes and a story rather than a permanent question mark.
As per Daniel Pink, life satisfaction leans heavily toward rich experiential memories over the safety of the familiar. When you make room for spontaneity, surprise, gratitude, and surpassing what you thought you could do, you build self-assurance, grit, confidence, and a personal narrative that loops back and skews ever more powerfully toward opportunity and possibility.
Now — Go Do Something
You've been sitting on something: a trip you haven't booked, a conversation you've been avoiding, an opportunity that scares you enough that's it's probably worth taking.
That discomfort you feel? That's the signal, not the warning.
You don't need more time, more certainty, or an optimal perfect plan. You need to decide and act knowing that real decisions are soon followed by action. No Action = No Decision.
Pick the thing that's been living in the back of your mind and take a concrete step toward that thing today — not Monday or when conditions are ideal. Today.
Your "I can't believe I did that" life is waiting. Go get it by earning your stripes and story.
