“Could I have done more?”
The man sitting across from me was on track for $20 million in revenue that year. He had the wife, the kids, the public success—everything we’re told to want.
And yet, every night, when he laid his head down, this was the thought that haunted him:
“I could have done more.”
I wasn’t ready for it. For a moment, I wasn’t even at that lunch table anymore—I was retreating inward.
If he still lives under the shadow of regret… what does that mean for me?
That question planted a seed that changed my life.
Today, I’m going to share three steps that guarantee you never have to ask it.
1. Always Aim Toward the Highest Future You Can Imagine
That lunch happened about a year into my real estate career.
By then, I had hit my stride—closing more deals than almost anyone in the company, which was the largest in the state. I had momentum. I had money. And for the first time, I started thinking long-term:
“What should I actually do with all this?”
So I asked my CEO to connect me with someone who could teach me the investment game—someone who had already walked the path I wanted to walk.
He introduced me to one of the most successful home builders in the state. I expected that lunch to be all about tactics, strategies, and spreadsheets.
But instead, I walked away with something I’ve never been able to forget.
Here was a man with everything you’re supposed to want:
- Wealth
- Legacy
- Family
- Accomplishment
And yet…
Every night, he laid his head down with that lingering question:
“Could I have done more?”
I couldn’t escape it.
If a man at that level felt that way, what chance did the rest of us have?
But what haunted me more than his regret…
was that he believed it was too late.
He wasn’t actively exploring how to fix it.
He wasn’t shifting course.
He had already resigned himself to endure the rest of his life—to just carry the weight to the grave.
And listen—he was only in his fifties.
That was the moment I realized something that would change my life:
The only thing that makes it too late…
is believing that it is.
So if you want to live without regret, it starts here:
Tell yourself the truth.
Listen to the voice whispering from the deepest part of you, beckoning you out of safety toward something greater.
And aim toward the highest possible future you can imagine—before the world convinces you to settle.
2. Never Settle for Less Than the Life You’re Capable of Living
In the end, this whole thing really comes down to two options:
- Aim upward and become the person you know you’re capable of being.
- Settle for less—which always, always leads to regret.
That’s it.
It’s not more complicated than that.
It’s just more convenient to pretend it is.
Because the first path is scary right now.
It demands your courage. It stretches you. It asks you to change.
But the other path—the path of settling—
That one’s quiet. Subtle. Painless… at first.
Until one day you wake up and realize:
You don’t want the life you’ve built.
And the tragic part?
By the time most people realize they’ve settled… they’ve made it permanent in their own minds.
So don’t wait for it to hit you that hard.
Don’t wait until you’re decades deep.
Choose the scary thing.
Do the uncomfortable thing now.
Or prepare to live with the pain of what could’ve been.
3. Your Greatest Life Lies on the Other Side of Your Greatest Fear
I’m not interested in clichés.
So no—this isn’t about “getting out of your comfort zone.” That’s a throwaway line.
Let’s go deeper.
There’s a quote from The Hero with a Thousand Faces by Joseph Campbell that changed my perspective on that lunch:
He said, “The cave you fear to enter holds the treasure you seek.”
That’s not poetry.
That’s reality.
Because here’s the truth:
The life you know you’re capable of living—the one that would light your soul on fire—is hidden inside that cave.
It’s dark. It’s unknown. You can’t see what’s in there from the outside.
So most people just… don’t go in.
They live their whole lives outside the cave, convincing themselves they’re happy with the safety.
But here’s the part no one talks about:
You already know the treasure is in there.
And you already know it won’t come to you.
It will cost you something.
But if you don’t go in, it’ll cost you everything.
That man I had lunch with never stepped in.
He had everything on the outside—but he ignored the cave.
And now he lives under the shadow of what could have been.
Please—don’t let that be your story.
Because here’s the final truth:
Regret is the default.
Courage is the only way out.
And yes—the gate is narrow. But if you find the strength to walk through it,
What’s on the other side is worth everything.
Conclusion
That question—“Could I have done more?”—has haunted me ever since that lunch.
And I never want to live a single day where I don’t already know the answer.
Because the truth is…
You already know what your cave is.
You know why it scares you.
And deep down, you even know the treasure waiting for you inside.
The only thing missing…
is a plan to go in after it.
That’s exactly why I built the Big Bad Plan Program.
It’s not motivational fluff. It’s not a goal-setting course.
It’s a system that helps you take what’s buried deep inside of you—and bring it out into the real world.
If you’re done settling, if you’re ready to make your next chapter the one you’re proud to look back on…
This is your first step.
And right now, you can lock in $50 off at checkout using the code FINDPURPOSE, one word and all caps. Learn more at www.bigbadplan.com.
This isn’t about hype. It’s about building a legacy you’re proud of.
Don’t let “I could have done more” be the final chapter of your story.
Let today be the day you started doing something about it, so that when your head hits the pillow at night, you never have to wonder: Could I have done more?
There you have it: 3 steps to avoiding the regret of a life left unlived.
- Always Aim Toward the Highest Future You Can Imagine
- Never Settle for Less Than the Life You’re Capable of Living
- Your Greatest Life Lies on the Other Side of Your Greatest Fear