I had already decided to change my career.
But the moment that pushed me there didn’t come from a job offer.
It came from a conversation.
But before that…
There was a moment I couldn’t ignore.
Earlier that year, my friend Kyle Goodman brought me with him on a Chairman’s trip.
We were at the Four Seasons in LA.
All paid for.
And I was surrounded by people my age…
making half a million… a million a year or more.
Traveling.
Living well.
Enjoying their lives.
At the time, I was doing residential real estate.
I was busy.
Closing deals.
Posting online.
Working nonstop.
From the outside… it probably looked like I was doing okay.
But being there…
I could feel the difference.
Because outside of that trip…
I wasn’t living like that.
I was on a $3,000 a month draw… against my commission.
Borrowing against myself just to stay afloat.
No savings.
No cushion.
Just trying to keep things going.
Even though I was active…
I knew I wasn’t doing great.
I just didn’t realize how far off I actually was.
The year before…
I had heard one of my best friends, Jay, made $200,000 in one month.
October.
That stuck with me.
So I called him.
I told him it wasn’t good.
And I asked him what he thought I had made so far that year.
It was July.
He said $250,000.
Just like that.
No hesitation.
Because to him…
That’s what “bad” meant.
I laughed.
And told him the truth.
It was $18,000.
I had another $18K in escrow…
So technically, about $36,000 for the year so far.
As a 1099.
That moment hit me.
Hard.
Because we weren’t even talking about the same level.
What I thought was me grinding and figuring it out…
wasn’t even close to what was actually possible.
And the crazy part?
Jay didn’t feel any different than me.
Same background.
Same type of person.
No superpowers.
He was just my old roommate with a food allergy to Cilantro.
What I didn’t realize at the time…
was that he was the number one producer in the entire company.
Way above average.
But I didn’t think about that.
I just saw what was possible.
And in that moment…
I made a decision.
I was going to change my career.
So I stepped away from residential real estate.
And I started applying for a corporate sales role.
Inside.
Commission-based.
In-house sales.
Working with existing owners, not chasing new prospects.
That’s where the real money was.
I only applied for that position.
But I also applied to their main competitor.
Not because I thought I would get hired with no experience…
but as leverage.
I wanted options.
And I wanted the company I actually wanted to work for…
to see that.
I didn’t want a job.
I wanted the opportunity to change my life.
Kyle helped me through the process.
How to apply.
How to interview.
He told me to flip it.
Don’t just try to get the job.
Interview them.
Ask what their top people make.
Ask what the training looks like.
Ask what the real opportunity is.
So I did.
Before I even went into the interview…
Another opportunity showed up.
Sam.
My old business partner from the tour company I had worked with on the streets of Waikīkī.
He heard I was making a move.
And he reached out.
At first, it wasn’t a real decision.
Because I still thought I had that $15,000 real estate commission coming in.
So I wasn’t really considering it.
But then…
That deal fell through.
Zoning issue.
Buyer backed out.
Just like that… gone.
Now everything changed.
Now I needed money.
And fast.
And suddenly…
That offer became very real.
Go back to Waikīkī.
Be the trainer.
Salary.
$10,000 sign-on bonus.
Immediate money.
Guaranteed.
Something I already knew I could do.
Something I had already proven I could be great at.
So right before my training for the new career started…
I went back for a couple of weeks.
$200 a day plus commission.
And it felt easy.
Same streets.
Same people.
Same system.
And I knew exactly how it would play out.
I’d make money.
I’d do well.
I’d be comfortable.
And that’s when I felt it.
Those golden handcuffs.
Not bad…
just comfortable.
But I had already lived that life.
I had finally broken free of that.
And now…
I was being offered a way right back into it.
Same streets.
Same system.
Same results.
Just with a better title…
and a bigger check.
Because now the decision was real.
Take the guaranteed money…
Or stay committed to something that hadn’t paid me yet.
I wasn’t going back to that version of my life.
So I stayed with it.
Not because I felt ready.
Not because it was safe.
But because I knew something simple:
If it didn’t work…
I could always go back.
But if I walked away from it now…
I’d never know what it could’ve been.
Looking back…
That decision changed everything.
Not because it was guaranteed.
But because I believed in myself enough to take the shot…
even when it felt uncomfortable…
even when it was uncertain.
I knew I could always go back.
But I didn’t want to look back…
and wonder what would’ve happened if I didn’t try.
Almost a decade later…
I’m still in commission-based sales.
Over 20 years now.
More than $30 million in sales.
A $600K year in 2022.
Multiple $500K+ years since.
Top 1% in the company.
And it all traces back to that decision.
