The Fear of Regret vs. The Courage to Act Part 2 of Your Year of Purpose and Possibility

Welcome back! If you joined me for Part 1 (Permission to Dream Big—Reclaiming Your Boldness), you’re already getting a taste of what it means to step boldly into 2025. If you missed it, no worries—you can catch up here. For now, let’s talk about something that keeps far too many of us stuck: the fear of regret and why courage is your secret weapon.

Let’s face it—regret is sneaky. It doesn’t slap you in the face like failure does. No, it lingers in the background, quietly whispering, “What if you had just tried? What could have been?” And while fear can sometimes keep us safe, it often does something far worse: it keeps us small.

Why Regret Hurts More Than Failure

Here’s a hard truth: regret stings way more than failure. Sure, failure isn’t fun. But at least when you fail, you gain something—clarity, experience, a story you can share at brunch. Regret, on the other hand, leaves you spinning in the what-ifs, wishing you’d had the courage to act.

Think about it: when was the last time you regretted trying something bold, even if it didn’t pan out? Now, when was the last time you kicked yourself for not even trying? That ache of “I should’ve…” hits differently.

Here’s the perspective shift that keeps me going: you can fail and recover, but you can’t go back and reclaim the chances you didn’t take.

Lessons From a Major Courage Moment: Blue Ivy Carter

Let’s talk about someone who gets this. Blue Ivy Carter just made her major movie debut in the upcoming Lion King movie, Mufasa. Imagine being the daughter of Beyoncé and Jay-Z. How easy would it be to let fear stop you from stepping into the same arena where your parents have dominated for decades?

But guess what? Blue Ivy didn’t let that fear win. She stepped up and, by all accounts, knocked it out of the park. And while we’re here, BEYONCé just made history, carving her space in country music with Act II: Cowboy Carter, making her the first Black woman to top the Billboard country chart. Talk about courage, legacy, and owning your moment.

These moments are a reminder that courage doesn’t mean the absence of fear. It means showing up, even when you’re afraid.

My 2024 Courage Moments

2024 had me flexing my courage muscles in significant ways. I wrote a book—The Lie: An Enchanted Revelation—that explores some of the pivotal lessons I’ve learned. I took my first solo vacation to Maui (10/10, highly recommend—it’s as magical as Instagram makes it look). I launched a business in a space largely dominated by white men, added my voice to the ever-growing cacophony of podcasts, and even started publishing fiction on Substack and Wattpad under a pseudonym. That last one was a little love letter to my 13-year-old self, the girl who dreamed of being the next Toni Morrison or Judy Blume.

None of these moves came without fear. Trust me, I questioned myself every step of the way. But here’s what kept me going: I’d rather face the sting of failure than live with the weight of regret. Fear passes; regret lingers.

Courage Is a Muscle

Here’s the good news: courage is a muscle, and the more you use it, the stronger it gets. You don’t need to wait until you feel fearless to act. Fear doesn’t have to disappear; it just can’t drive the car.

Taking calculated risks—whether that’s starting a new project, stepping into a new role, or finally pursuing a long-held dream—is how we grow. And trust me, courage doesn’t always look bold in the moment. Sometimes, it looks like sending the email, signing up for the class, or just showing up for yourself when staying in your comfort zone feels safer. Often, it looks like doing it with shaky hands, a wobbly voice, and no one standing beside you.

And let me be clear—this isn’t me sugarcoating failure. Failure isn’t fun. It’s messy, uncomfortable, and sometimes downright embarrassing. But you know what’s worse? Not trying at all. Wayne Gretzky said it best: “I skate to where the puck is going to be, not where it has been. You miss 100% of the shots you don’t take.”

Sure, failure stings. But regret? Regret leaves you wondering what might have been. Calculated risks are how we meet our future selves—those wiser, braver versions of us waiting on the other side of the leap. It’s not about recklessness; it’s about intention. It’s about seeing where the puck is headed and having the courage to skate toward it, even when the ice feels unsteady.

So, no, I’m not here to sell you a fairytale version of courage. It’s hard. It’s scary. But it’s also worth it. Every step you take toward your dreams, no matter how wobbly, is a step away from regret—and that’s a move worth making.

3 Ways to Turn Fear Into Action

If fear of regret has been keeping you stuck, here are three things that help me keep moving:

1. Ask Yourself the Future Question. Whenever I’m scared to act, I ask myself: If I don’t do this, how will I feel in a year? Five years? Imagining future regret is often all the motivation I need.
2. Take One Bold Step. Courage doesn’t mean doing everything at once. It’s sending that DM, making the phone call, or finally booking the ticket. Boldness grows one step at a time.
3. Reframe Failure. I’ve learned to see failure as a teacher, not an enemy. Every stumble gets me closer to clarity and success.

Why Calculated Risks Matter

Let me be clear: courage isn’t about acting recklessly—it’s about being intentional. When I decided to write my first book, I didn’t just dive in without a plan (okay, maybe a little—self-publishing, anyone? Whew, what a ride). But I made it happen by setting clear goals, carving out time, and staying committed, even when it felt overwhelming. Courage doesn’t mean having it all figured out; it means taking the leap while figuring it out along the way.

A mentor once told me, “You don’t have to know how the story ends to write the first chapter.” That’s the power of calculated risks. They create momentum, and with momentum comes clarity.

Choose Courage

Here’s the thing: fear will always be there. It’s part of the human experience. But so is courage. The choice is yours—do you let fear of regret keep you stuck, or do you choose the courage to act?

Because let’s be real: no one looks back on their life and says, “I’m so glad I played it safe.” The best stories, the ones worth sharing, are the ones where you chose courage over comfort.

So, what’s one bold move you’ve been putting off? What’s one small, intentional step you can take this week to move closer to it? Write it down. Take the leap.

2025 is waiting, and it’s yours for the taking.

Stay tuned for Part 3 of this series: Unlearning Perfectionism—The Power of Imperfect Action. Because sometimes, just starting is the bravest move of all.