How to Take a Career Break: 8 Steps to Reset and Find Your Calling

This post on how to take a career break was featured in Vol. 1, Finding Your Calling of The Unconventional Monthly, a newsletter that gives you fresh ways to live a little more extraordinarily on a new topic every month.

From Career Break to Breakthrough

Fed up with work, feeling uninspired and unfulfilled, and thinking of taking a career break?

I know the feeling. I broke after only four-and-a-half years.

The last straw, actually the last email, for me was being told I’d been taken off the fast-track and put into a boringly comfortable assignment. It wasn’t enough to get me to focus on Excel spreadsheets instead of the palm trees outside my windows anymore. So I handed in my key card and hung up my khakis to reassess and redirect my career.

Some call it a career break. I called it my “pretirement.” 

Whatever you want to call it, it lasted five years—an unforgettable, unpredictable time I wrote about here—and it ended with a breakthrough: finding a new career I love.

Maybe I was fortunate, but I believe if you follow these eight steps for how to take a career break, you might have a breakthrough, too.

8 Steps to Finding Your Calling on a Career Break

Chris practicing giving speaches
Practicing for when one day I get on the big stage.

1. Set a Big, Broad Goal

A big, broad long-term goal will motivate you to keep trying new and meaningful things and guide your decision-making in the right direction during your career break.

My big, broad goal was to give TED Talk. Not TEDx. The real-deal main stage. Achieving it would mean I’d found something valuable to contribute to society, which was missing from my previous career.

It’s still my goal. I’m nowhere close, but I’m still moving in the right direction.

minimalist packing list for men
Keeping a minimalist packing list was part of my freedom-granting pretirement package.

2. Assemble Your Pretirement Package

You’ll need the following five things to have a successful career break, especially if you too are starting from scratch on your path towards your big, broad goal: 

2.1 Money

Money enables you to travel and reset, cover minimal living costs, and invest in ad-ventures. We’ll get to each of these in a bit. 

In my case, I had stashed away about $250k in cash in the bank by the time I pretired.

2.2 Freedom

Free yourself from as many obligations as you can: jobs, responsibilities, pets, debts, property, etc. 

That way, you can live anywhere and pursue anything (…or anyone, as was the case for me going after my now-fiancée, Kim).

2.3 Understanding Friends and Family

Do the best you can to explain your career break and your goals to your friends and family to get them on board. You don’t want them to hold you back and pressure you to “get serious” and to go back to a “real job.”

2.4 Tall Fences

“The grass is always greener on the other side,” as they say…

….so build up some towering fences to block the view. 

That way, you can focus on your own plot and not feel discouraged by comparing yourself to friends and ex-colleagues, whose grass will seem a lot greener while you’re on your career break.

But install some gates in your fence, just in case they invite you over for a barbecue.

2.5 A Backup Plan

Don’t pretire without a solid resume in your back pocket. It’s your insurance policy. It lets you take risks knowing that, if worse comes to worse, you can always find a job. 

 3. Get Your Money Working While You’re Not

Since you’re not working, your money needs to work extra hard for you.

Ideally, you’ve been investing your savings ever since your first paycheck. But if you’re stupid like me and were “too busy” to properly manage your money while working, make it your first pretirement priority.

Investing can be intimidating but isn’t as complicated as expensive-suited financial planners want you to believe. Read Millionaire Teacher for a quick and easy guide.

Consider checking out these books, too:

I went on the llama and didn’t even alpaca computer.

4. Factory Reset Yourself

You know how after you factory reset your phone it works so much faster and the battery lasts way longer?

Well, factory resetting yourself gets you the same benefits.

Here’s how to do it:

  • Trash all non-essentials and eliminate all obligations, worries, deadlines.
  • Shut yourself down.
  • Spend whatever time it takes to start back up again. 

My factory reset took six months. For the first couple, I roamed around South America with just a small backpack and no computer. Then I hopped around from one friend or family member’s place to another to re-establish connections with them. And then I returned to my hometown of Vancouver, Canada to spend my first carefree summer since I was a kid.

By the end of your factory reset, you should feel good as new.

stone training workout
Upgrading my body with full-body rock workouts.

5. Upgrade

Once you’re good as new, get better than ever. Use the bandwidth you’ve freed up from your factory reset to go on a self-improvement spree.

Here’s what I did to upgrade to Chris 2.0:

  • Learn how to learn: Rather than stuff myself with mental fast food that went right out the other end, I taught myself how to focus on the right knowledge, consume it carefully, digest it, and apply it.
  • Better diet: I beat my addiction to snacking and processed foods and got into fasting and making my own food.
  • Smarter exercise: Instead of trying to be more jacked and stronger than everyone, I ditched the gym and shifted my focus to functional strength and mobility.
  • Closer relationships: I learned how to be less of a prick and used that skill to somehow win over my soon-to-be-wife, Kim.
  • Wiser spending: Rather than be bogged down by tons of unnecessary crap and expenses, I freed myself up mentally and financially by only spending money on the best of what I truly needed.
One of my failed ventures: Butter made from insect fat.

6. Put Your New Powers to the Test

After your upgrade, you’ll feel like Peter Parker after he got bit by a radioactive spider and discovered his new powers: super excited to put your new abilities to the test. 

Do it!

Just prepare to smash into a lot of walls and fall on your face plenty before figuring out how best to use them. 

I sure did. I…

  • Failed at disrupting the Vancouver taxi industry
  • Ended up in a lawsuit in a fruit export business
  • Gave up on trying to sell protein powders and butter made from bugs
  • Got restless and got bought out from a hostel I co-owned.

When the going gets tough, keep in mind that these “failures” are the conflict that’s necessary for any great story. They’re also teaching you way more about yourself than your old job could ever do.

Chris smelling his stinky synthetic shirt.
Huh… my sh*t does stink. (So I started wearing merino wool.)

7. Get Real

As if we’re looking at some distorted funhouse mirrors, we all see ourselves as someone we’re not.

This is the reason we get ourselves in the position of needing a career break in the first place, the reason we fail early on, and our biggest hurdle to finding our true calling. So straighten out that self-reflection of yourself ASAP.

Your early career break failures will help. Be open-minded enough to take responsibility and learn from them instead of making excuses. If not, you’ll soon be begging for your old job with your tail between your legs.

For instance, my repeated failures made it clear that I’m not caught up to be a superhero startup founder. My true self prefers the independence of working on my own, being creative, and having the freedom to follow my fleeting interests.

Your straightened-out self-reflection may also not be as impressive as you’d imagined. Or maybe you’ll discover you’re more impressive than you thought. Either way, it’ll clarify the path you should take to find a fulfilling career.

Chris blogging in Rwanda
I love what I do so much that even when we’re away in places like Rwanda, I can’t stop doing it.

8. Make a Breakthrough

If you’re patient enough to follow the previous seven steps for how to take a career break, you’ll eventually make a breakthrough and stumble on something worth ending your “pretirement” for and getting back to work on. 

For me, that turned out to be blogging. I never would have suspected it, but thanks to my misadventures I discovered a deeply-buried passion for writing, marketing, and tinkering with websites.

My pre-career break self would be disappointed. My post-career break self can’t be happier.

And that’s the point. You can’t know what’s best for you until you take a career break to go looking.

Yes, it’s scary not to know where to look and how long it will take to find, but it’s even scarier to wonder what will happen if you don’t.

Are You Ready For a Career Break?

I’d make a horrible career counselor, but if you leave a question about your situation in the comments, I’ll do my best not to screw you up even further.

And if you have advice or experiences from your own career break, please share with us and fellow readers, too.


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Chris and Kim

Kim and Chris started The Unconventional Route in 2018 to share their experiences exploring extraordinary places, things, and ideas. Now, over 150,000 people a month read their questionable advice. Every week, they share a new complacency-challenging and curiosity-tickling idea in their newsletter, Consider This.

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