The Cost of Playing It Safe
Why Your Biggest Risk Is Taking None At All
"You miss 100% of the shots you don't take." - Wayne Gretzky
Here's a truth I rarely admit: For most of my life, I was terrified.
Not of failing. Of wanting.
I was the good girl who colored inside every line. College degree? Check. Marriage? Check. Graduate school? Check. Children, community involvement, the "flexible" job that let me be the parent I thought I was supposed to be? Check, check, check.
From the outside, I was winning at life. From the inside, I was suffocating under the weight of all that certainty I'd built around myself like a fortress.
The truth I couldn't face then: I made almost every decision from a place of fear, not vision. I needed to know I was doing everything right, on time, on schedule. I needed guarantees. I needed safety.
And I wasn’t happy.
When I finally listened to my inner wisdom—that voice that had been whispering and then screaming for years—I realized my marriage wasn't aligned with my truth. And as it happens, divorce wasn't the end of my story. It was the beginning of my unfolding.
That's where I learned what it means to take big swings.
Recently, I had two separate conversations that landed in the exact same place. One with a dear friend, another with my son. Both entrepreneurial spirits who see possibility where others see risk. Who believe in abundance when the evidence isn't there yet. Who aren't tied to what they're supposed to do because they're too busy creating what they want.
We talked about taking big swings. About belief. About courage.
And I was reminded again that: Big swings get big results.
Yes, you might miss sometimes. But you'll also hit those home runs far more often than if you never stepped up to the plate.
Small swings? That's what we tell ourselves is "responsible." That's chipping away at our lives slowly, carefully, safely—while our deepest desires gather dust on a shelf marked "someday."
What Taking Big Swings Really Costs (And What It Gives You)
My post-divorce life forced me to take bigger swings. Not because I was suddenly brave, but because playing it safe had already cost me so much.
And here's what I discovered:
When you take big swings, you:
Discover capabilities you didn't know you had
Build a level of self-trust and strength that changes everything
Create experiences that become part of your story, not your regrets
Model bravery for everyone watching (yes, they're watching)
Access a version of yourself that's been waiting for permission
When you play it safe, you:
Trade possibility for the illusion of control
Slowly erode your trust in your own inner wisdom
Build a life that looks good on paper but feels hollow in your heart
Model fear and scarcity to everyone who's learning from you (especially your children)
Miss the life you were actually meant to live
Here's the part that still catches me off guard: Even after everything I've built, that deeply grooved "good girl" identity fights me every single day. The one who believes being responsible means being small. The one who thinks courage is reckless and safety is virtue.
I practice every day—inviting in my voice of courage, confidence, belief, and boldness. And I've grown so much stronger. I'm hitting more balls out of the park now.
Because there is a cost to staying safe. To being "responsible" in ways that keep you small. To chipping away at your life rather than experiencing it boldly, loudly, and full-on. To missing experiences that your heart and soul really want.
Why We Don't Take Big Swings (And What To Do About It)
So, let’s look at what holds us back:
1. We Crave Certainty
Our brains are wired to prefer known misery over unknown possibility. We'd rather have a guaranteed mediocre outcome than take the risk for something extraordinary.
The shift: Start small. Take one swing this week that scares you a little. Not everything-at-stake scary. Just enough to remind your nervous system that uncertainty doesn't equal danger.
2. We Confuse Responsibility with Self-Abandonment
Somewhere along the way, being responsible became code for ignoring what we actually want. We wear our self-sacrifice like a badge of honor while our dreams die of neglect.
The shift: Ask yourself: What would I do if I trusted myself completely? Write down the answer. Then ask: What's the smallest step I could take toward that truth today?
3. We're Terrified of Disappointing People
We've built entire identities around being dependable, reliable, safe. Taking a big swing feels like betraying everyone who needs us to stay small and predictable.
The shift: Recognize that your courage gives others permission to be courageous. Your big swings show them what's possible. The people who truly love you want you to be free, not small.
4. We Don't Believe We're Worth the Risk
This is the deepest truth: We don't take big swings because somewhere inside, we don't believe we deserve the home run. We're more comfortable with comfortable.
The shift: Start tracking your wins. Every single one. Build the evidence that you are, in fact, someone who succeeds when you try. Your inner wisdom already knows this. Your scared self needs proof.
Building Your Big Swing Practice: 5 Strategies That Actually Work
1. Name Your Non-Negotiables What matters so much that you'd risk everything to protect it? This is your North Star. Every big swing you take should align with these values. When you know what you stand for, decisions get clearer and courage gets easier.
2. Start Where You Are (But Start) You don't need to quit your job and move to Bali. Big swings aren't always dramatic. Sometimes they look like: having the hard conversation, saying no to what drains you, investing in yourself, choosing the path that excites you over the one that looks good.
3. Build Your Truth-Telling Muscle Practice telling yourself the truth about what you actually want. Not what you should want. Not what would be responsible. What do you want? Get uncomfortable with your own desires. Get familiar with them. Honor them.
4. Create Your Courage Circle Surround yourself with people who swing big. Who believe in possibility. Who won't let you play small just because it's comfortable. This isn't about cheerleaders—it's about people who see your potential and refuse to let you forget it.
5. Track Both Your Swings and Your Misses Here's what most people don't tell you: The misses teach you more than the wins. Keep a journal of every big swing you take. What happened? What did you learn? What would you do differently? This becomes your playbook for bold living.
So let me ask you what I ask myself almost daily:
Where are you not taking swings?
Where have you convinced yourself that small and safe is the same as smart and responsible?
Where have you traded your truth for the comfort of certainty?
Where have you built a life on the outside that feels empty from the inside?
And here's the follow-up: What would it take to swing bigger?
Not recklessly. Not irresponsibly. But aligned with your deepest truth and your boldest vision.
What would it mean if you did? What might become possible?
The Truth About Time
Here's what I know now that I wish I'd known at 25: Time doesn't wait for you to feel ready.
Your life is happening right now. Not when you're more prepared. Not when the conditions are ideal. Not when you've checked all the boxes and earned your permission slip.
Now.
The question isn't whether you're ready to take big swings. The question is whether you're willing to look back at your life and wonder what would have happened if you had.
Because playing it safe? That's the biggest risk of all.
