take a career break mini-retirement on a beach

How To Successfully Take A Career Break Worry-Free

Let’s face it – we all want to take a career break. Who doesn’t want to relax with family and find new inspirations? But your fear brain is asking, “how will you find a job again?” or “what will others think about your joblessness?.” Time to snooze that fear and do you. Since you’re already working multiple jobs, you are in a strong financial position to take a career break. In fact, disconnecting from work for a year might just help you sustain your 2-3x income in the long run! We’ll explain more. Now, let’s get scheming on how to make a mini-retirement happen…

It’s time for a mini-retirement…

But Wait, What’s This Crazy Mini-Retirement Idea

Mini-retirement is a concept popularized by Tim Ferriss in The 4-Hour Workweek that you need a clean break from work to reset. I dislike the book because most OEs don’t hate our work but rather thrive in context switching and launching projects. But alas the idea is powerful.

You have probably heard or seen something similar, like the four-to-six weeks paid sabbatical after “x” years that tech companies offer as retention incentives. Other examples are the merchant mariner working for six months at sea followed by a long break on land; the oil rig engineer operating on a two-weeks-on, two-weeks-off schedule; the flight attendant flying on a rotating 5-day schedule. Expand on this concept and you’ve got the mini-retirement.

To be clear, a mini-retirement isn’t a vacation or short, unpaid leave. It’s a complete break from work as you know it, and there’s no desk for you to come back to unless you’ve planned ahead (more on this later). However, it’s a finite period, usually six to twelve months, depending on your budget. Now, combine mini-retirement and OE, and you’ve got a powerful motivation to earn and rest on repeat.

Naysayers Objecting To A Career Break

For most people, taking a career break is like committing career suicide. They’re worried about killing the cash flow golden goose. But for the Overemployed (OE), this fear is irrational. OEs are working two jobs at the same time, at the same desk, and at home – who would think that was possible? Time to update your mental model and design mini-retirements into your life.

Forget about traditional retirement – work your whole life, save up a nest egg, and ride out into the sunset. That was for your parents and grandparents. Now, you can work multiple jobs and take a year off to live overseas. Who knows, you might just come back rejuvenated about 2-3X-ing your income again.

Now go tell your boss and other naysayers to buzz off. Embrace the fear. Live your life. Are you ready?

Steps To Taking A Mini-Retirement

Mindset is the first thing. You already know that looking for a job again after your mini-retirement isn’t a deal-breaker thanks to OE. You’ve got your network and past clients to fall back on. You understand work is a two-way street, you’re dispensable and so are the jobs. There’s always another gig or job on the horizon. Let’s talk about planning and executing your mini-retirement.

1. Don’t jump into mini-retirement right away, tiptoe in instead

Like all things OE, we try things out incrementally, like overlapping jobs to test out the concept of OE itself. Start by taking a 3-week break from all your jobs. See how you like it. Then up the ante, and try a 6-week break from all your jobs, and see if they’ll pay for it (“oh Mr./Ms. Boss, I’m so burnt out…”). See what I did there? Play the burned-out card. Did you like your time off? If not, stop here (you must be weird, just kidding).

If your boss tells you “no way I can let you take six weeks off,” then it’s time to brush up on the HR handbook and look into the company’s leave of absence policy. The most likely scenario is you take a 30 to 60 days unpaid leave of absence. At the end of the trial run, you’ll still have two jobs waiting for you. This is the safe play. But as you guessed, OEs like to go big or go home.

So you played the burned-out card and didn’t get that early paid sabbatical. But don’t quit for free. Take a page from How to Engineer Your Own Layoff and engineer your own mini-retirement. Ask for a severance to recoup from being burned out. Is there a better way to start off your career break than successfully negotiating a couple of sign-off bonuses?

2. Create a budget for your mini-retirement

You’ve decided you want a career break. Wonderful. The next step is to look at your finances and create a budget. If you’ve been avoiding lifestyle creep while earning six figures, then chances are you should have plenty saved up. Use a portion of it to fund your mini-retirement. It’ll be well worth it.

Now let’s look at your expenses, such as housing, school/child care, utilities, food, transportation, insurance, debt service (why do you still have debt ?!?), among others. Leave no stones unturned by giving them a set of critical eyes along with your spouse or a neutral third party. Differentiate between needs versus wants. Derive at a number you’ll need to live a year without any income. Now multiply that number by 1.25 to give yourself a 25% buffer. Life happens, so you’ll need a buffer in case you get into an accident or encounter unanticipated expenses.

Were you able to negotiate partial pay or severance for your mini-retirement? If yes, then put that money in your budget. That’s just icing on top.

3. Plan what you want to do while on your career break

First, it’s also ok to have no plan at all. But in case you need some cash flow during your mini-retirement, or think you’ll get bored, now is a good time to consider keeping one or two contract jobs while on your break. This will slow the budget burndown as well as keep your skills sharp. I also understand if you want to unplug completely – to each their own – just depends on what you can afford.

Next is the fun part. Get together with your loved ones and brainstorm on where to live and what to do. Personally, we’ve always wanted to live in Europe and travel for a year, so we’ve been eyeing cities like Trieste, Italy, or Strasbourg, France as a home base for our upcoming mini-retirement. Whatever you decide, it should be an adventure and a wonderful life experience, the good with the bad. Take it all in good stride.

4. Exit mini-retirement and back to work

Don’t let this be a downer. In fact, you should be excited for what’s ahead – another change in your OE-to-FI adventure. Who knows what new professional challenge awaits you. What’s more, you’ll be looking forward to your next mini-retirement again in 2-3 years. Time to fire up the job search, land multiple gigs, and fund that next mini-retirement. Along the way, you continue to max your tax-advantaged accounts and make strides in becoming FI early.

Doesn’t A Career Break Delay My Financial Independence?

I’m not going to lie, the simple answer is yes. But I’d also say seeking financial independence (permanent sabbatical) is overrated because that’s living in the future. What’s more important is financial resilience, and living in the present. If you OE and live in the now, that day when you’ve achieved financial freedom will come. And when it does you won’t even notice it. Don’t make achieving FI your sole goal in life or you’ll wind up feeling empty in the end. Of course, this is my personal opinion. But I felt it when I crossed my first million years ago. I was like, is that it? Huh!

What I do know is your earning endurance is what makes FI certain. That’s why I OE, switch jobs, upskill, and network. And also why buying insurance and annuity to de-risk future cash flow is important (more on that in another post).

Put it this way – if taking a mini-retirement means you can come back and sustain your 2-3x income for a little longer, then you should think of mini-retirements as a cost of the OE lifestyle. You have to take mini-retirements in order to get to FI. I’ll let that thought sit with you for a moment.

Reasons For Taking A Career Break

You’re young-ish only once (yes, even for yours truly, and I consider 60’s as young-ish). Don’t wait to live life in the now, like eating at that Michelin 3-star restaurant or driving that super fast (rental) sports car on the Autobahn. Take the opportunity to vacation and backpack with your kids. Make memories. Time doesn’t wait, it just keeps ticking.

Part of the OE ethos is to never forget the main reason why you’re working two or more jobs: so that you and your family can live a better life. There’s no point in OE if you haven’t prioritized health, wealth, relationships, and purpose. Money is a renewable resource; time isn’t.

More importantly, if you’re already 2xing, or your income is built on leverage such as code, new media, or any kind of intellectual capital, you’re set to make back that money in no time.

Apart from that, taking a mini-retirement is for the greater good. Sometimes you have to slow down to go faster. All of us need some time in life to reflect and do mid-course adjustments to stay on the right path. Without the buzz of work running in the background, our minds are free to contemplate where we are, what we want, and how to live in the now. And who knows, you just might come up with an idea that could 5x – 10x your income.

What Happens Next?

There are a ton of potential outcomes after your mini-retirement.

Plan A. You could plan for re-integration. Set yourself a 3-6 month runway to do your job search if you want to return to working full time. If you’re able to, pick up a new language or skill, or do volunteer work so you can explain this gap in experience when re-interviewing for jobs.

Plan B. Or who knows? Maybe you’ll be inspired to go into a completely new field, start a business, meet someone or decide to have another child. Maybe while you’re sipping a piña colada on a beach, you’ll meet a potential investor or business partner who can help you start that coffee business you’ve always wanted to run. Or while making new friends on a backpacking trip, you realize being a digital nomad is what you really want now.

Regardless of what happens, you’ll be re-inspired, re-aligned with your goals, and ready for wherever life takes you. And that’s the beauty of taking a pause. Similar to OE, taking mini-retirements is like cheating in the game of life.


  1. Have a friend who is self employed describe freelance or contract work you did for them during your time away. The employer doesn’t need to know you’re friends – just that you had employment continuity to put their mind at ease. Mix in some courses you took (and be able to demonstrate those new abilities if they’re relevant) to show initiative. As long as you can show you didn’t just surf Netflix for six months, they will tend to gloss over it and return to focusing on how you can solve their problems. That’s what most want now: how can you help me solve the problem I have?

  2. Will this mini retirement affect the carrer in general? Let’s say you are a software engineer, what would be a good explanation for this year gap in your CV? Thank you for the answer in advance!

    1. As the article suggests, one of the options is to have a contract gig running in parallel with your mini-retirement just to show employment continuity for concerns you’re alluding to. I, for one, don’t have such concerns. An SWE’s skills are always in demand, especially if you’re good.

    2. Or keep one of your jobs and just slow play it while you hit the beach.

      Or start an LLC and do some work part time, or some pro bono stuff (or just start an LLC and _say_ that’s what you were doing).

      Or tell them you used the time to upskill, do some bootcamps or whatever.

      The possibilities (real and fictional) are endless. Mix and match.

Leave a Reply

Your email address will not be published. Required fields are marked *