Please ease feel free to read the below blog but, I added the podcast version for audio.
All of my podcast link can be found on the homepage!.
E45: Retire TO something instead o fFROM something!
🎙️Side Hustles & Backup Plans in Retirement
Retire TO Something, Not Just FROM Something!
We’re flying into Episode 45, with a plane towing my banner over Rocky Point, Mexico!
Even my podcast can’t stay in one place!
Today? Side hustles and backup plans in retirement!
They say don’t just retire FROM something. Retire TO something.
I was laid off at fifty-two in February 2024, after eighteen years in telecom and seven in fintech.
I decided to take a run at early retirement.
Turns out, when every day is Saturday, you eventually forget what the hell day it is.
I don’t have kids or grandkids. School pickups and soccer games aren’t my retirement. Nothing wrong with that life. It’s just not mine.
I need to create my own reasons to get up in the morning.
NorthAmericanDarrell.com is my hobby: blogs, podcasts, YouTube, and slow-travel stories.
I run a one-man media empire.
The boss is questionable, and HR has given up!
Then there’s my side hustle: my Airbnb condo in Mesa, Arizona.
For four years, it’s brought in twelve to seventeen thousand dollars a year before hosting expenses.
That helps offset the three thousand dollars a month I distribute from my retirement investments.
It’s not a replacement for a retirement plan.
It’s another leg holding up the stool.
And when somebody rents my home, I have to move out and go somewhere else.
Poor me!
Rocky Point, Mexico, is right there, and my condo is waiting!
Sometimes I’m off exploring a whole different country.
My condo makes money while I make memories.
After staying in more than a hundred Airbnbs, I know the difference between a welcoming home and a place you’re afraid to touch.
I clear out my personal belongings, make sure the place is spotless, and leave returning guests their favorite nightcap.
And the coffee station? I may have gone a bit overboard.
If the caffeine supply ever becomes a national emergency, my condo might qualify as a strategic reserve.
Solana has two pools, a hot tub, a gym, and a clubhouse.
Great for remote work or retirement.
But the best part? The people.
Ted’s returning for his third stay: nine weeks with his other daughter.
Ted takes fantastic care of the place.
My neighbors love him.
Rumor has it he walks the complex picking up stray trash.
That’s more than I can say for a few owners.
Some of them may actually be his suppliers.
He prepaid months in advance.
I trust him, he trusts me, and that’s worth a lot.
At the beginning of September 2026, though, Ted’s was my ONLY booking.
Every year, I convince myself bookings are drying up.
Maybe everybody moved to Mars.
Every year, it works out.
A guest from my hometown of Edmonton booked a three-week stay in November.
Then another guest booked three weeks, with check-in the very next day!
I was sitting in the sauna at Lifetime Fitness when the message arrived.
“Can I check in tomorrow?”
Sure!
I was only planning to continue existing peacefully.
Book the maid. Rent a trailer. Store my stuff. Arrange the Rocky Point shuttle. Get ready in twenty-four hours.
Retirement suddenly felt like owning a hotel, a moving company, and an emergency dispatch center.
It worked.
My guest arrived and messaged me that everything was fine.
What a relief!
Some guests need a home for work.
Some are in a tough spot.
Others are escaping winter.
We’re helping each other.
Here’s what I’m learning: retirement takes more than a pile of money.
Investments are my foundation.
Airbnb adds flexibility.
My website is a hobby that travels with me.
Travel keeps me curious.
And I still have to protect what I’ve earned.
Watch the withdrawals.
Keep emergency savings.
Stay on top of healthcare coverage and unexpected expenses.
Cheap flights are wonderful.
Cheap flights followed by an expensive medical surprise? Not my favorite itinerary!
As Freedom Fifty-Five approaches, things are lining up.
I don’t need a conventional retirement.
I need one that works for me.
Some days, it’s a blog, a guest, or a flight halfway around the world.
And some days, I just hope I can sit in the sauna without starting a moving company!
Don’t just retire FROM something. Retire TO something!