Eddie Pinero
Posts
I dare you to....

I dare you to....

September 17, 2025

What if I told you the greatest risk you’ll ever take is…. not taking one at all?

The real gamble isn’t the exam, the job interview, or the leap into the unknown. The real gamble is waking up every day, clinging to comfort, and slowly trading your dreams for regret.

I was talking to a friend recently about the LSAT. He told me how nervous he was. How the test felt like a giant wall standing between him and his dream. I asked him what felt scarier: walking into that exam room or living the next ten years wondering what could have been if he didn’t try.

That’s the cost of risk. Not the trembling hands. Not the pit in your stomach. But the much heavier price of never stepping forward at all.

Risk is everywhere. It’s in applying to a school or job you’re not sure you’ll get. It’s in telling someone how you really feel. It’s in waking up every morning and choosing happiness before circumstances give you permission.

The mistake most of us make? We measure risk only in terms of loss: What if I fail? What if I look foolish? What if it doesn’t work out?

But we rarely measure the bigger loss: What if I never even give myself the chance?

Because here’s the truth:

When you don’t take the test, you’ve already failed it.
When you don’t start the project, you’ve already abandoned it.
When you don’t risk joy, you’ve already settled for something less.

Life is a gamble either way. Playing it “safe” doesn’t actually protect you. It just guarantees that you’ll pay with regret instead of growth.

Maybe your “LSAT” isn’t a literal exam. Maybe it’s a conversation you’ve been avoiding. A passion project collecting dust in the corner. A dream you’ve written off as “unrealistic.”

The question isn’t whether there’s risk involved. The question is: which risk are you willing to carry, the sting of trying and falling short, or the lifelong ache of never knowing?

I’ve come to believe happiness itself is risky. To say, “I choose joy” each morning is to risk disappointment, to risk being misunderstood, to risk not fitting the mold. But that’s a cost worth paying because the alternative is far too expensive.

Here’s the paradox: the more you risk, the less risky life feels. Courage is a muscle. The fire becomes familiar. And one day, you realize the real danger was never the leap… it was standing still.

So, what’s your LSAT right now? What risk are you staring at? And are you ready to pay the cost of not taking it?

Continue to live inspired,

P.S. So excited to have officially launched my new apparel brand, Always Grateful, Never Satisfied. You can join our email list here, where you’ll get daily inspirational quotes, access to new limited drops, and a code for 20% off the entire store. Thanks for being part of the journey!

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