Pretirement: When Early Retirement Isn’t Early Enough

I was too young and too unwealthy to retire, so I "pretired" instead. This is my pretirement story.


My friends and colleagues chuckled incredulously when I told them I was “pretiring” at the tender, naive age of 27.

“No, really,” they’d ask, “what are you going to do next?”

“Not sure.”

I’d saved quite a bit during my 4.5-year corporate career, but not nearly enough to cover me for the rest of my life. Even FIRE (financial independence to retire early) would have taken me another five years of paychecks. But I couldn’t wait that long.

I needed an indefinite career break to catch my breath and reassess my path. Then I figured I’d find a way to become the universe-denting CEO I believed I could be.

That was six years ago.

If anything, the universe dented me rather than me dent it. The only thing I’m CEO of is this humble little blog. But I’m happier than ever. So I’d say my pretirement was a great success.

This is my story.

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Chris traveling during pretirement
Me on my victory lap. Fittingly, the company I pretired from owned the Pringles brand.

The Factory Reset

Like many real retirees, the first thing I did after pretiring was travel.

And, let me tell you, traveling when you’re pretired is the best.

You have no obligations, no upcoming deadlines, and plenty of money, so you can go wherever and do whatever for as long as you want, worry-free. And you don’t need to pack a laptop.

For six post-pretirement months, I:

  • Explored the jungles, mountains, and beaches of South America,
  • Hopped from one friend’s place to another in Switzerland, France, Spain, Germany, and the Netherlands,
  • Toured my friends around Panama, where I’d been living and working for two years, and
  • Spent my first carefree summer in my hometown of Vancouver since my early teens.

By the end, I was traveled-out. And my mind felt like a computer that had been factory reset. The junk had been cleaned out and I never felt fresher.

So I settled down in Vancouver for the next stage of my pretirement.

Had I not given myself an extreme self-makeover, I would never have met and held onto Kim (pictured here on our first extended time together, which is a whole other story).

The Upgrade

With nothing but time on my hands, I got around to things that I “was too busy for” during my working days:

Putting My Money to Work

The costliest mistake of my life was not putting my money to work for me while I was working. I just stuffed my savings into a checking account and let them slowly deflate.

Worst of all, Finance was my profession!

So stupid.

I could have about twice as many savings today had I put my money to work for me starting from my first paycheck.

But better late than never. Pretirement gave me the time to get my financial act together. I wasn’t working so my money had to work extra hard.

And did it ever!

Thanks to patience, thriftiness, and lucky timing, my savings grew faster during my pretirement than they did when I was working.

Investing Tip

Read Millionaire Teacher, one of the “sledgehammer” books that changed my thinking, to get comfortable with investing and to learn it doesn’t have to be complicated. And don’t dilly-dally!

Embracing the Simple Life

Being tight with my money (my friends would say “cheap”) allowed me to pretire in the first place, but I had to clench up a couple more notches to keep my pretirement going indefinitely.

These financial “sacrifices” turned out to be super rewarding:

I used to believe most of the above was hippy nonsense—stuff broke people rave about to justify their inability to afford anything better.

But, as is the case more often than I’d like to admit, the hippies were right.

Embracing the simple life gave me the freeing realization that I could thrive on much less than I once thought.

Getting an Extreme Self-Makeover

I redirected all the mental energy I didn’t need for meetings, emails, and Excel to research and experiment with ways to improve myself.

I learned to:

  • Eat healthier and way less frequently.
  • Change my fitness routine to build a useful, long-lasting body rather than a show-off-y one.
  • Value my time more by logging everything I do.
  • Appreciate new hobbies like writing and photography.
  • Not to be a self-centered prick (not as much of one, at least).

Thanks to these upgrades, I felt like Chris 2.0—healthier, happier, wiser, and better-off financially than ever.

So I was eager to put my new powers to work.

My friend Jorge and I trying to sell bug butter and protein in one of my pretirement misadventures:


It was time to step out swinging into the universe to see what damage I could inflict.

  • Taxi Disruptor. I followed my hate of cars and traffic to get really into the future of urban transport. This led me to nearly managing Uber in Vancouver, pitching a municipally-owned ride-sharing app to City Hall, and, most improbably, interviewing to be GM of Vancouver’s largest taxi company. But, in all cases, I was left sitting on the curb.
  • Blueberry Baron. An acquaintance from my old employer called me out of the blue (literally, as you’ll see..) with the most random request: Could I find and ship 40 tons of frozen blueberries to Mexico City in less than two months? Up until then, my biggest blueberry purchase was a 1kg bag at Costco. But, somehow, I made it happen! And we profited big-time. Just like that, I was in the export business. But easy come, easy go. Things got complicated, our partnership went rotten, and within a year I was deported from the company.
  • Bug Guy. My interest in healthy, sustainable food led a friend and me down a worm-hole with a crazy idea: feeding perfectly safe food waste to the world’s most eco-friendly and economical animal, black soldier fly larvae, and processing those maggots delicious critters into protein powder and a coconut oil alternative. We got a government grant, got into a start-up accelerator, and got partnerships with bug farms… but never got regulatory approval to sell our bug guts.
  • Hostelier. I accepted an invite to form an unlikely triumvirate with my mom and my brother’s friend, buy a property in an up-and-coming outdoor adventure destination near Vancouver, Squamish, and turn it into a hostel. This business was a hit from the start. Not a universe-denter, for sure. But at least not a blow to my ego.

I ultimately gave up my fruitless fight to become a universe-denting CEO when my then-girlfriend, now wife, Kim and I were told we’d have to vacate our apartment for redevelopment.

Instead of struggle to find a half-as-good apartment in Vancouver for twice the price, we took off for somewhere warmer and cheaper: Medellin, Colombia.

Back to South America, where my pretirement began.

Back to square one?

I’m living a cliché, taking cliché photos like this, and loving it.

Back to “Work”

Lucky for me, my invested savings were having a lot more success than I was. So Kim and I didn’t feel the pressure to make money selling trinkets on Amazon or teaching English online, which is what it seemed all the other gringos in Medellin were doing at the time.

We could enjoy exploring Medellin and its surrounds instead.

And we discovered a lot of extraordinary things travel blogs and guides didn’t mention. So, thanks to the website-building skills and aptitude for writing I developed during my misadventures, we started to blog about it.

We couldn’t find a perfect domain name, so we settled on

Unlike my previous ventures, people seemed interested in this one. Traffic grew and grew. And we were having tons of fun working on it.

Within just over a year, we started making money! Nothing close to enough to make us rich. But it was enriching work. It covered our expenses. And I still had my pretirement savings working for me.

Then it dawned on me: this was it. My pretirement was over.

You Never Know What’s Next

My 27-year-old pre-pretirement self would be horrified that I’ve become a blogger.

I hated English in school, never wrote anything more than emails, never designed anything more than PowerPoint presentations, didn’t own a camera, and had no interest in marketing. And I wanted to be rich.

But my pretirement misadventures taught me otherwise.

That’s the magic of pretirement. It enables you to stumble into living by the cliché, “Find a job you enjoy doing, and you will never have to work a day in your life.”

Blogging’s not lucrative nor impressive, but who cares?

I like to think I’m contributing some value to the nearly two million people who visited this site last year. My financial situation’s stronger than ever. And so are my health and my mind.

So yeah, life’s pretty awesome right now.

Will it stay that way? Who knows?

Worse comes to worse, I can always pretire again.

What’s Your Pretirement Plan?

Only a tiny minority of people are fortunate enough to be able to pretire like me. Even still, too few people do it. It seems people don’t seriously consider a pretirement plan because:

  1. They aren’t aware it’s an option.
  2. They’re afraid to “risk it.”

Well, seeing as you’ve made it this far, excuse A is off the table.

As for excuse B, ask yourself this:

If you pretired, did a factory reset, reconstructed, and pursued (mis-)(ad-)ventures, how likely is it you’d regret it and crawl back to your current job?

Probably not very likely, or you wouldn’t have read this post in the first place. So consider risking it.

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About the author

👋 I'm Chris. Everything you read on is my fault. This site is like a gym for your comfort zone, full of challenges to make your status quo sexier. Join my 'Consider This' newsletter for a fun new challenge every 10 days. Try it!

6 responses to “Pretirement: When Early Retirement Isn’t Early Enough”

  1. Glenn Avatar

    Never heard the ‘pre-retirement’ term before…sounds better than me referring to testing retirement waters. I’m 52 yrs old and probably wouldn’t have even tried the FIRE movement had it not been for cryptocurrency investments (largely unrealized gains at this point).

  2. Chris Avatar

    Yeah, “testing the retirement waters” sounds a bit tepid. Some of the older retirees have undoubtedly peed in the retirement waters’ pool, too. I’m glad you like the “pretirement” term. And congrats on the good luck with crypto… assuming you get out at the right time.

  3. Rick Weldon Avatar
    Rick Weldon

    Doing what you are doing. I have to admit “pre-tirement” is a great way to put it. I’m at the travel around phase. So far Ecuador, Peru, Portugal, Spain, Austria. In London as I type this and headed to Albania next. I haven’t worked in 1 year and 9 months. (Airbnb for the win). I’m 58 now and trying to do a reset; get my head clear. I want the “non-job” too. The problem is I don’t want to go to an office. I may just do the “nomad’ thing. It is weird traveling like this. I avoid the touristy stuff and find people can’t handle it when you have no agenda. In every country I’ve gone to, I’ve been through the “How Long You Here For?” my reply, “till I get tired of here” 🙂

    1. Chris Avatar

      Haha, either “till I get tired of here,” like you said, or “until my tourist visa expires,” right? Enjoy Albania and best of luck stumbling across your non-job soon!

  4. JESSE OWENS Avatar

    I work as a janitor for a community college and get every weekend and holiday off – something that I never had working previously in Foodservice, Security, or Retail. My side hustle is e-commerce. I set up a blog and an online mall last August; didn’t see any real gains until the beginning of this year. All it took was a friend or two buying from my site to boost my confidence to place more ads. Been using the term “pretired” w/o considering all the parameters you mentioned (lol). To me, it just sounded cool to say b/c I’m “traditionally” too young to retire. I’m 45, unmarried, and no kids. I feel like I should’ve done this years ago, but the pandemic really put things into perspective:

    When it comes to your health, well-being, and finances, what better time than NOW, if not ANY time to improve?

    I wish all of you luck & success!
    Thank you, Chris for sharing your story. May we all inspire each other.

  5. French Life Community Avatar
    French Life Community

    Excellent Article, Excellent Blog , Excellent Site ✅✅✅

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