How to Take a Career Break: 8 Steps to Break Through

Worth the Risk?

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. I was assigned to a boringly comfortable role instead.

It wasn’t enough.

I couldn’t shift my focus from the palm trees outside my window toward my Excel spreadsheets anymore. So I handed in my corporate key fob and hung up my khakis to reassess and redirect my career.

Some call it a career break. I call 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 got lucky.

But I’m willing to wager that if you follow these eight steps for how to take a career break, odds are good you’ll make a breakthrough, too.

1. 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: 

1.1 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.

1.2 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 wife, Kim).

1.3 Understanding Friends and Family

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

1.4 Tall Fences

I don’t agree anymore with the saying that “the grass is always greener on the other side.” My lawn’s pretty sweet these days.

But it certainly helped to build up some tall fences while I was sodding my soil during my career break. I didn’t need the discouragement of comparing my uncertain situation to my friends’ and ex-colleagues’ established, and seemingly very green, ones. 

1.5 A Backup Plan

Don’t leave a perfectly good job for a career break without a solid resume in your back pocket. It’s your insurance policy. You can take more risks knowing that you can always find a job if worse comes to worst.

2. Start Setting Your Mission

This might sounds corny to you. It did to me too. But it has motivated me to keep trying new and meaningful things and guided my decision-making in the right direction throughout and after my career break:

A personal mission statement.

A personal mission statement is no different from a corporate mission statement. It captures the problem you seek to solve with your life, how you intend to do it, and your vision of what the result will be.

My business is my life and I’m the CEO. Successful business have mission statements. So why shouldn’t I?

Here’s how my ever-evolving personal mission statement stands today:

 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 isn’t as complicated as expensive-suited financial planners want you to believe. Read Millionaire Teacher for a quick and easy guide. Your future self will thank you.

Consider checking out these books, too:

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, you get the same benefits from factory resetting yourself.

Here are the buttons to push:

• Trash all non-essentials and eliminate all obligations, worries, deadlines.
• Shut yourself down.
• Take longer than you think 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 around Europe to re-establish those connections. After that, I returned to Vancouver to spend my first carefree summer since I was a kid.

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

And ready for an upgrade.

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, blind taste testing, palate training, 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. I’d rather be the world’s fittest 100-year-old.
• 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 unnecessary crap and expenses, I freed myself up mentally and financially by only spending money on the best of what I truly needed.

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 these “failures” happen, keep in mind that they are the conflict that’s necessary for any great life story. They also teach you way more about yourself than your old job could ever do.

…If you heed the lessons, that is. Which brings us to the next career break step.

7. Get Real

The biggest reason we get ourselves in the position of needing career breaks in the first place, what causes fail early on, and our biggest hurdle to finding our true calling is this:

We all see ourselves as someone we’re not.

It’s as if we’re looking at distorted funhouse mirrors, So straighten out that self-reflection ASAP. If not, you’ll soon be begging for your old job with your tail between your legs.

Your early career break failures will help you get real with yourself. Be open-minded enough to hold yourself accountable for them and learn from them instead of making excuses.

Be prepared for your straightened-out self-reflection to be less impressive than you’d imagined. For instance, my repeated failures made it clear that I’m not caught up to be a superhero startup founder. I’m an independent, creative, lifestyle business type of guy.

At the same time, you may discover you’re more impressive than you thought. At the very least, I discovered some people enjoyed my writing.

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. That means stumbling on a job you love worth ending your “pretirement” for. 

For me, that turned out to be blogging.

My pre-career break self would be disappointed at what I’ve become. 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.

For more of a push to take your life down exciting directions, you might choose to check one of these related posts out: