Pretirement: When Early Retirement Isn’t Early Enough


When I was 27, I did the most privileged-millennial thing possible:

I retired.

My friends and colleagues laughed incredulously when I told them. They’d ask, “No, really, what are you going to do next?” And I’d tell them, “Nothing. I have no plans.”

But while I had no future plans, I had been planning this step for the past five years, ever since I started my corporate career. I’d even come up with a name for it:


Unlike real retirees, I hadn’t saved enough to cover me for the rest of my life, so it wasn’t a true retirement. I also didn’t want to just play golf, hang out somewhere warm, and drink wine. And I hated bingo.

I just knew I needed an indefinite career break to decide if the path I was going down was the one I wanted to continue on.

That was six years ago.

Turns out I ended up doing a whole lot more than nothing during that time. I factory reset, reconstructed, ad-ventured, and stumbled into a money-making non-job I love.

And somehow I have twice as many savings as I did when I pretired.

In other words…


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

Factory Reset

Like many 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, and spent my first carefree summer in hometown Vancouver since my early teens.

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

I settled down in Vancouver to figure out what to do next.

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).


With nothing but time on my hands, I got around to things that I “didn’t have time 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 50% to 100% more 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 for me.

And did it ever! Thanks to fortunate timing and patience, my savings grew faster than they did when I was working.

Investing Tip

Read Millionaire Teacher 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 (friends would say “cheap”) allowed me to pretire in the first place, but I had to tighten up a couple more notches to keep my pretirment going indefinitely.

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

I used to believe this was hippy nonsense—stuff people without money used to justify their inability to afford anything else.

But 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

Another pretirement realization:

I wasn’t the hot shit I thought I was during my corporate career. I was full of it.

Pretirement gave me the time and freed up my mental energy so I could fix my shit: self-assess, study, and experiment.


  • Started eating healthier and way less frequently.
  • Changed my fitness routine to build a useful, long-lasting body rather than a show-off-y one.
  • Valued my time more by logging everything I do.
  • Dove into new hobbies like writing and photography.
  • Most importantly, learned how not to be a self-centered prick (not as much of one, at least).

Healthier, happier, and more financially stable than ever, 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 ad-ventures:


Knowing I eventually needed to work again, but without strict time pressure to earn money from it, I followed my interests and unexpected opportunities into various (ad-)ventures:

  • Taxi Man. 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 publicly-managed ride-sharing app to City Hall, and, most improbably, interviewing to be GM of Vancouver’s largest taxi company.
  • Blueberry Baron. An acquaintance from my old company 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? I had no idea where to start, but I somehow made it happen! This led to a brief, lucrative, and eventually litigious tenure as co-owner of a Mexican import-export business.
  • Bug Guy. My interest in healthy, sustainable food led a friend and me down a worm-hole to the crazy idea of making protein powder and a coconut oil alternative out of insects fed on food scraps. We got a government grant, got invited to an accelerator, and got partnerships with bug farms… but never got off the ground.
  • Hostelier. I accepted an invite to be part of an unlikely triumvirate with my mom and my brother’s friend, buy a property in an up-and-coming outdoor adventure destination near Vancouver, and turn it into a hostel.

None of these ad-ventures proved to be worth permanently ending my pretirement for, but they were way more rewarding and educational than what I was doing pre-pretirement.

And they led me down a path toward the perfect non-job I never would have imagined myself doing…

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

The Perfect Non-Job

The perfect non-job is what you’re looking at right now. This blog.

My 27-year-old pre-pretirement self would be horrified.

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 marketing. And I wanted to be rich.

But my pretirement ad-ventures 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?

Hundreds of thousands of people read my words every month (and I like to think I’m doing more good than harm). My financial situation’s stronger than ever. So is my health and my mind. Life’s pretty awesome right now.

Will I keep it up? Who knows?

Worse comes to worse, I can always pretire again.

Should You Have a Pretirement Plan?

I know I’m lucky to be one of a small minority of people fortunate enough to have been able to pretire, but I also know there are many more people who should do the same but are afraid to try.

Ask yourself this:

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

If you’re not sure, you might want to consider making a pretirement plan.

See my post on How to Take a Career Break: 8 Steps to Reset and Find Your Calling to get started. And maybe also check out my Framework for Finding a Job You Love, for some questions to ask yourself to help you choose a fulfilling career path.

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4 thoughts on “Pretirement: When Early Retirement Isn’t Early Enough”

  1. 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. 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. 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” 🙂

    • 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!


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