Breaking Free

How To Get a Second Chance at Life the First Time Around

Photo of Andrew Henderson

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3 min read

How To Get a Second Chance at Life the First Time Around

If I could go back and give my younger self one piece of advice, it would be this:

“Never settle.”

When I think back on earlier versions of me—especially the moments when opportunity was right there for the taking—I see it clearly:

The only thing that held me back… was me.

I doubted myself.
I thought I needed more time.
I assumed I'd get another chance.

But that’s not always how life works.
Sometimes the door closes—and it doesn’t reopen.
And the path you’re forced to take instead?

It’s longer.
Harder.
Steeper.

That’s what self-doubt steals from us.
Not just opportunities—
Years.

Regret Doesn’t Come from Failure—It Comes from Inaction

People like to say “If I knew then what I know now…”

But what they’re really saying is: “If I believed in myself then the way I do now…”

Because when you look back at old photos, old work, old opportunities—you often think, Damn… I actually had it. I was more capable than I realized. More talented. More attractive. More ready.

But in the moment, you were too critical to see it.

That’s how insecurity works—it distorts the view from the inside.

Fear Shrinks Our Lives

From the moment we’re old enough to desire something, that inner voice shows up to whisper: That’s not for you. You’ll embarrass yourself.

  • Want to ask someone out? Fear.
  • Try out for the team? Fear.
  • Apply to your dream job? Fear.
  • Start your own business? Fear.

And when we listen to that voice—when we let it win—our world gets a little smaller. Until, little by little, we're practically invisible.

We shrink from the challenge.
We tolerate relationships we’ve outgrown.
We settle for the lot we didn’t want—but convinced ourselves was destiny.

The People We Admire Are Just People Who Went for It

We celebrate the bold ones. The artists, the athletes, the entrepreneurs.
We say things like “I could never do that.”

But that’s not true.
They’re not different. They just went for it.
They walked toward fear, when we stood still.

So What Would Your Future Self Say to You Now?

That’s the question I’ve started asking myself.

Because I know I’m going to look back at this current version of me one day and say:
“You had more in you than you knew.”

And I don’t want to keep repeating that story.

So I’ve started giving myself the encouragement I wish I had years ago.

Not to be reckless.
Not to chase validation.
But to stop waiting to feel perfectly ready.
To just throw myself into things and trust that I will figure it out.

I started my business with this mindset.
Not because I was fearless—but because I was tired of regretting the times I let fear win.

You Still Have Time

No matter how old you are—30, 50, 75—if you're still breathing, you still have time.

Time to try.
Time to change.
Time to live.

Take care of your dreams the way your future self would want you to.
Appreciate your body the way your older self will look back and wish you had.
Give yourself the love, belief, and confidence you would give your past self—right now.

Because if you do that, it’s like getting a second chance at your whole life.

You Deserve to Believe in Yourself

You’ve survived every day so far.

Whatever risk you're contemplating? You’ll make it work.
Whatever dream you’re afraid to chase? You’re ready for it.
Whatever version of you you’re becoming? That person is waiting.

So give yourself the gift of boldness.
Be the version of you that knows everything will work out—even if it looks messy along the way.

Because confidence doesn’t come from success.
It comes from choosing to believe you deserve to try.

And you do.

Marcus Aurelius may have said it best: “Think of yourself as dead. You have lived your life. Now take what's left and live it properly.”

You don’t need a second life to make the most of this one.
Start now. Start here. Start with belief.

You’ve waited long enough.
It’s time to stop holding back—and start living like your life depends on it.
Because it does.

Tags

Breaking Free,Personal Growth,Spiritual Entrepreneurship,Purpose-Driven Business,Entrepreneurial Journey,Creator Mindset
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