Why I Hesitated to Take Risks, and How Failure Helped Me Grow
I’ve always been a careful person.
Not afraid of challenges, not even afraid of failure, really. But regret? That haunted me.
It wasn’t the fall that scared me. It was the moment after — when you’re lying there, staring up at everything you hoped for, and realizing it didn’t go the way you dreamed. It was the thoughts that crept in after:
"Did I make a mistake?"
"What if I had chosen differently?"
"Was this even worth it?"
For the longest time, I let that fear hold the steering wheel. I played it safe. I made the choices that felt smart, practical, low-risk. And for a while, it worked. I avoided disappointment — but I also avoided growth. I avoided pain — but I also avoided depth.
Until life pushed me anyway.
When Playing It Safe Starts to Hurt
I remember one opportunity in particular. A chance to start something new. Something bold. Something mine.
I had the vision, the drive, and the support. But I also had that voice in the back of my head:
"What if you regret this? What if it doesn’t work?"
So I hesitated. I stalled. I watched that window slowly close while I tried to decide if it was worth the risk. And when it was gone, the regret I had tried so hard to avoid found me anyway. Only now, it came with a heavy side of what could’ve been.
Turns out, inaction hurts too.
This realization changed something in me. Because for the first time, I saw that the cost of never trying was just as steep — maybe steeper — than the cost of failing.
The Psychology Behind Regret and Risk
It wasn’t just me — there's actual science behind this. Psychologists Thomas Gilovich and Victoria Medvec studied regret and found that while short-term regrets tend to revolve around actions that didn’t work out, our long-term regrets are mostly about the things we didn’t do (Gilovich & Medvec, 1995). The dreams we didn’t chase. The chances we didn’t take. The words we didn’t say.
That hit me hard. Because when I looked at my own story, I could see it was true. My deepest regrets weren’t about the risks that didn’t work out — they were about the ones I never gave myself a chance to try.
And when I did start taking risks, yes — some of them didn’t go as planned. But every one of those “failures” gave me something that staying still never could: growth, resilience, a deeper understanding of myself.
How Failure Became My Teacher
There’s one moment I come back to often.
I took a leap — a real, terrifying, heart-racing one — on something that mattered deeply to me. It didn’t go the way I hoped. There were tears. Doubts. Sleepless nights where I questioned everything. But a few months later, I looked back and realized that even though I didn’t “succeed” in the traditional sense, I had changed.
I had more courage. I had clearer boundaries. I had a better sense of what I wanted — and what I didn’t. And maybe most importantly, I realized I survived. The world didn’t end. The regret didn’t crush me.
In fact, it lifted me. It clarified me. It gave me direction.
Psychologist Angela Duckworth calls this grit — the power of passion and perseverance in the face of difficulty. And it’s true. I wouldn’t have developed grit if I’d kept hiding from failure. I had to face it, feel it, and get back up anyway.
What I Know Now: The Risk Is Worth It
I still get scared. I still overthink. But I’ve stopped letting regret be the villain in my story.
Now, when I stand at a crossroads, I ask myself:
“Will I be proud that I tried?”
Not “Will this work?” Not “Will I regret it?” — just, “Will I be proud of who I became for trying?”
And that simple shift changes everything.
I’ve learned that becoming who we’re meant to be doesn’t happen in our comfort zones. It happens in the uncertainty. In the bold choices. In the risks we take, even when we’re afraid.
To Anyone Else Who’s Hesitating – the pain of failure is temporary. The growth is not.
And regret? It will show up either way. So why not earn it trying to become everything you’re capable of?
You won’t always get it right. But you will become.
And that’s more valuable than any guarantee.
–HumanityECW







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