#23: Chronicles of the Career Breakers 💼

a synthesis of sabbatical stories

Dec 13, 2022

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Over the last year, whenever I met someone who had taken a career break, I was eager to hear their story. Voluntarily leaving a job without having another one lined up seemed daunting to me, but the seed was planted in my mind and I couldn’t help but wonder. I recently asked over a dozen Career Breakers to share their stories for my own curiosity and for anyone else out there stuck in a state of paralyzing contemplation. Looking at the responses, it’s clear that there’s no one-size-fits-all formula to follow. With the help of my friends, I hope we can demystify the notion of taking a break from work, show how diverse each individual’s path is, and encourage everyone to check-in with themselves and their relationship to work.

The made-up term ‘Career Breaker’ describes an individual taking a break from their career. But maybe it’s also someone who’s breaking out of the default narratives and instead going off the beaten ~~path~~ corporate ladder. Hmmm, or maybe I misspelled it and its actually ‘Career Braker’, someone who has decided to hit the brakes on their always-on career. To slow down, for just a bit.

Resetting assumptions

Recently, I’ve been probing myself all sorts of questions about our relationship with work. I’ve never seen any job description break down how long each responsibility should take, yet we still anchor to 40 hours as the standard.

Retirement as a concept is mind-boggling to me. Why do we wait until we’re 62+, when our bodies are in the most feeble state, to finally have the free time to do what we want? Why do we wait until our minds maturely fixate and habits entrench to attempt new things?

Currently, the default is to work continuously until your net worth peaks and only then exit the workforce. I question the entire narrative that we should work continuously for decades until a single point in time when we leave and never return. To me, the optimal point to take a career break is once you have enough saved up to live off savings for a bit and have an initial sense of what to do with the extra time. Even if it’s not something specific like traveling the world or pursuing a ‘passion project’. It could just be taking a few months off to rest and read.

Chronicles of the Career Breakers

I recently sent out a questionnaire to over a dozen Career Breakers. Most are friends, but a few are fellow online writers who I’ve never met before (the power of the internet!). I asked them to reflect on their end-to-end experience from when they first had the idea to quit all the way until now. I realized that there isn’t a script to read off of or a syllabus to follow.

While the pre-career break vocations fall within a narrow set of labels like software engineer, doctor, investment banker, the post-career break activities have a wide range. It’s so dope to read about what people are up to now. They’ve been self-studying quantum mechanics, pursuing acting, learning a new language, writing a newsletter, and more. I wonder about all the uncaptured curiosity, creativity, and craft as a result of society steering us to have a singular defined full-time job, rather than a multi-dimensional, fluid set of projects.

I mapped out the recurring themes from the Career Breakers. Let’s dive into some of those👇

The initial seed
Planning the career break
Crossing the chasm
Emotions of quitting
Navigating uncertainty
Exploring new skills and curiosities
Rest and recovery
Avoiding boredom
Relationship with money

From when you decided to quit, how long did it actually take for you to leave?

Responses ranged from 2-3 months all the way to 7 years! For most people, it took them about a year from the initial idea to actually quitting.

my reaction: Everyone has to process things at their own speed. Unwiring our prior assumptions about work and career can take time since it’s such a big component of our livelihood.

How long did you think your career break would last? How many months of savings did you prepare?

Most people planned for their career break to between six months to a full year, but there were also some that wanted to go for the foreseeable future. Most people conservatively saved up more than they actually needed (planning for 6 months, saving up for 12 months).

my reaction: Practically, it’s hard to save up for anything longer than a year. The fact that people saved up a lot more than needed seems debunk the risk-seeking stereotype. In reality, people were quite pragmatic.

Crossing the chasm

Deciding to walk away from a stable, full-time job can seem like taking a leap of faith. Not only are you walking away from a guaranteed paycheck, you’re choosing an opposing path to your sense of identity:

In my observation, physician burnout is an amorphous, existential feeling that occurs due to the gap between what we entered our field to do: help people vs. what it actually feels like we are doing. Everyone has different reasons on different days, but the ultimate feeling is one of meaninglessness and futility.
I suffered from a pathological addiction to work, titles, accolades. I grasped firmly at my role in society and fused my identity with my career. This socially acceptable form of addiction was reinforced when I saw the powerful reaction that saying "ER Doctor" had on the people I met. My external career served as a way for me to ignore my internal pain.
When I stripped this away, I had nothing but myself. This was uncomfortable, compounded by my own stigma toward unemployment. At first, my reaction was to fill time by learning, training, or scheming my next gig. Because I intended to stay unemployed for 9-15 months, I eventually hit a wall.
This uncomfortable space of nothing to do made me recognize that I had to deal with my demons in order to not repeat the cycle and end up in a job that would be a poor fit. There's no timeline, and there's no blueprint. My guess is that this is a lifelong process. I'm gathering tools and addressing key points so that I can continue working on self in my next role. - Ted

I grew up in a Chinese immigrant household. It definitely influenced my risk tolerance. I was the first son and had always been the good kid. Plays nice, follows instructions.
My dad penny-pinched on lots of small things, and I think that rubbed off on me. I didn’t like to spend money on anything. Money was for saving, not for spending.
The family went through some money troubles while in college, and I felt like it was my responsibility to support my parents.
I definitely felt like I had golden handcuffs, that I was throwing away a guaranteed six-figure salary and lots of benefits for guaranteed no income for a while (because I knew I wanted time to explore, not necessarily start a new business right after quitting).
I didn’t know anyone personally who was succeeding in a creative career. That scared me that it might not be possible for someone in my position. - Kevin

The hardest part was probably getting my parents' buy-in. They knew that I was unhappy, but because they'd lived their lives with general risk-adversity, the industry-wide layoffs, hiring freezes, and upcoming recession made them nervous. Ultimately, though, my dad has always been a vision-oriented entrepreneur himself, and I think he was proud to see me try that path myself. - Tiffany

The emotional aspect of walking away from your job

I noticed a common theme of nervous excitement among almost everyone as they approached the finish line of quitting, the end of the beginning. They were also plenty of worries that turned out to not be true at all:

I felt a lot of nervous excitement. I had my own worries about whether I'd ever get a job that paid as much again (I did) and whether I was making a mistake (I wasn't). I was shaking when I put in my two weeks notice. - Sanjeevi

I felt nervous uttering the actual words to my boss that I had made a decision. But he said he was proud of me for making the decision. He agreed a sabbatical would be good for me. On my last day, I was surprised at all the warmth and support I got. I thought maybe people would be resentful of me for leaving and putting more work on their plates, but I realized if I were in their position, I wouldn’t feel that way at all. - Kevin

[I felt] nervousness/relief, because the startup I was working on was really busy. I was the only point person for certain tasks, and I felt like I was disappointing my teammates. None of that was true, my teammates were actually really happy for me. - Raymond

Known downside, unknown upside

Any big change is inherently asymmetric. The nature of change requires us to leave what we’re familiar with and enter uncertainty. Whether it’s positive or negative, we know what we’re walking away from. But what lies ahead is unknown. This biases us to have a visceral sense of what the downside is (running out of money), yet also leads to a limited perception of the upside.

Lawrence Yeo writes: “While you can easily predict the concerns of making any leap, there is no way to predict the numerous rewards that await you on the other side. As long as that chief concern is one you think you can manage, the most rational thing to do is to actually make the jump. By not making that leap, you are voting to give up all unimaginable future rewards for a single concern you can predict and prepare for today.” - Kevin

In a lot of ways the best case scenario was harder to imagine -- that I develop more as a person, that I have fun? It felt radical to spend money on that. - Sanjeevi

It’s a bit silly, but this reminds me of the Mr. Beast video where he walks around Walmart asking if people want to buy a $5 mystery box. The first few people turn him down, worried that there’s nothing inside and they’ll end up losing their precious $5. They fail to imagine that there could be $10k inside (narrator: There was.) For further exploration, read Lawrence Yeo’s Take the Leap.

Exploring the edges of the unknown

Given that most people planned their career break for months, you might presume that they all had a concrete plan. However, there are so many unknown unknowns. Every Career Breaker had a compass, but no map. A sense of direction, but no designated path to follow.

I became a lot more comfortable with living life without the structure. I also realized I have a lot of passions and would explore them more if I didn't have a demanding job. … I’m actually saying yes to more things now because I’m more open-minded versus I would have to say no to more things while I was working. - Abe

I knew I had many informal goals that I wanted to focus on at some point in my life but had no sense of priority or order to any of them. A random sample of these goals include from living in new countries, studying physics and philosophy, learning how to sing and dance, and creating art and music. - Evan

I think one of the biggest "AHAs" for me came when I started writing online and realizing how much energy I felt from it. I caught myself thinking about writing more than I was thinking about my job every day. For over a year, I would wake up early to get in a few hours of writing before going to work. I hadn't felt so motivated or drawn to something in such a long time. The state of flow I feel when writing started to outweigh the other things I valued that I was getting from my job (money, stability, prestige to some extent). Writing like this reminded me that there were other creative interests that I've also forgotten somehow along the way - acting, filmmaking, etc. I started asking myself: could I test out a life where I was spending the majority of my day on these creative interests?- Shiv

My goals were to improve my Chinese, exercise more, practice an instrument and learn to produce music, and study a new field on my own (like biology, economics, or physics). In my mind, it was probably going to be all focus. In practice, it's probably been about 50/50 discovery vs focus. - Dan

Using time to rest and recover

Without the proper time to step off the proverbial hamster wheel, it can be difficult to know how you’re really doing. We often end up burying ourselves even deeper in our work as a way to mask the symptoms. Taking painkillers instead of rehabilitating. Slamming espresso shots instead of sleeping.

I lost my motivation for months, so initially [the break] was about "finding my curiosity", which can be a sign of burnout. Talking to strangers and old friends helped with this. - Daniel

[The most unexpected part of my career break] was wrestling with existential identity issues and mental health ups and downs. It turns out work is an easy scapegoat and provides a lot of structure. Without those boundaries, you find yourself accountable for your life and your mindset at a whole 'nother level. … I got through a lot of potential anxiety by just doing things. I changed how I thought of myself. - Sanjeevi

Being forced to quit in a way was the best thing to happen to me. Though I knew I was burned out, I didn't understand the extent that my clinical job affected my health, mood, and wellbeing until months later. In early 2022, I took a hard break on all work to spend time focusing on recovery and to re-assess priorities. - Ted

Not actually being bored

Without the repetitious confines of a full-time job, boredom can be a legitimate concern. Fortunately, that doesn’t seem to materialize once you’re actually in the career break.

Most unexpected thing? That I haven't been bored at all this whole time.
- Chris

When I was preparing to quit and talking to friends about it, a common thread that people would mention is that they would get bored with all that free time. While I was employed, I never found myself getting bored, but I did wonder if that would change with dramatically more free time. But after 16 months off I am thrilled to report that I still have yet to find myself getting bored and I'm pretty confident that I will never get to that point now.
Separately, a surprising finding for me was that my mind is able to wander a lot more than before. I didn't realize how much of my time was spent thinking about work until after I quit and all that mental real estate disappeared. Since then I've found that what I am thinking about changes pretty drastically depending on what goals I am focusing on at the moment. - Evan

How your relationship with money has changed

While quitting your job to live off savings does require cash in the bank, what ultimately prevents people from actually taking the leap rarely has anything to do with money. I tried to see if there was any correlation between salary and the subsequent career break. Now I can conclude there is zero correlation. Take two people both making over $200K per year. For one, it took them just a month to realize they wanted to take a short (<6 month) career break. For the other, it took them seven years to actually quit and their goal is to go for as long as possible..

Growing up, for the longest time I thought the norm was to have just one pair of shoes. One for each foot. What would more do? I distinctly remember in college carefully considering whether I should pay an extra $2 for guac at Chipotle. I still do sometimes. Looking back, I was going through the mental gymnastics of factoring in when the last time I had guac was, how stressed I was in the moment, how hard my last workout was, and what my next meal was going to be, just to make this two buck decision.

Now that I make cushy tech money, I’ve started spending on things like an Equinox gym membership and occasionally taking an Uber to the airport instead of the subway. The vast majority of these purchases are worth it to me and I think I have a healthy relationship with money. I still wonder how can I be more grateful for what I have. Maybe it takes not having income (temporarily) to fully appreciate what I have right now. Maybe it’s time to give up the eucalyptus towels and Kiehl’s and lug a couple suitcases down the steps of the MTA.

So I asked the Career Breakers: How has your relationship with money changed?

Money felt the most precious when I was burnt out at a job and saw it as a source of freedom. Maybe also when I saw it as a pile that was being depleted by my time off. Now that I'm working a job I like and accumulating again, I feel the most comfortable spending that I ever have. - Sanjeevi

Extreme conscious of budget. Much less anxiety and more realistic about how much I spend. No shame, just numbers. - Daniel

More frugal, cooking more, spending less. I actually think of money more when doing things which I don't necessarily like. Right now in the state of meandering and exploration I am a bit more aware of my money and spending. I’ll optimize less, cook more, walk more because time is less of an issue. - Abe

Graduating with debt made me more comfortable with the idea of hitting a $0 balance. While I don't intend to put myself there, I am training myself to see money as a gift. Sometimes there will be abundance and sometimes it will be a trickle; both are okay. - Ted

Evolved to more of an abundance, as opposed to scarcity mindset. I used to think that the best way to be financially free was to save up, but the much easier thing to do is just to make more. - Raymond

Advice for those considering

Maybe you find yourself watching Youtubers vlog a lifestyle that you find fascinating. Or perhaps you find yourself feeling a little jealous of that one friend (yes, that friend). If there’s any inkling that you might consider a career break, here is some advice for you:

If you’re considering it, it’s inevitable. Start building up your savings and define a number you would feel comfortable drawing down from. Conduct a mini-experiment by taking longer PTO (maybe around the holidays) and see what you do with your time. Are you energized and looking for more? Name the fear: do a fear-setting exercise and recognize what the cost of inaction would be for you. - Kevin

One guideline I use when deciding between life choices is if I am ever choosing between risky dramatic options and safer options, I lean to the riskier change because the safe choice will always make me wondering what could have been. The risky choice at the very least provides the answer. Not a hard rule of course but just general guideline. - Evan

Like a newly grad? Don't try to have an objective. You won't end up where you think you will anyway.
1) Chase interest over anything else. 2) If it's common knowledge, question it.
- Chris

Think less about what you want to do with your life, and focus more on why. By practicing this, you'll get more in touch with the intangible aspects of life that contribute to your individual sense of fulfillment. Does your happiness depend on others noticing? If so, will their approval keep you happy in the long run? If no, then what do you know makes you happy over long periods of time? - Ray

I highly recommend anyone considering this path to start with some sort of vacation where you commit to doing nothing for defined period of time before jumping into any specific/time-bound projects.
…
Find community amongst others who have done something similar. - Shiv

Take time off work, ideally >10 days. Then, after 10 days think about what you want. Does it fit?
…
Be patient and think on a 30 year horizon. - Daniel

Enjoy the journey. If your body/soul sends you a message, listen to it. - Ted

Recommended Resources

Articles
Crash Only Thinking
The Trouble with Optionality

Podcasts
Afford Anything with Paula Pant
Mr. Money Mustache episode of the Tim Ferriss Show podcast

Books
Four Hour Workweek (specifically the idea of mini-retirements)
The Pathless Path (recommended multiple times + my 👍 too)
Whatever You Think Think The Opposite
Shoe Dog
Range
Designing Your Life
Books on spiritual materialism and shadow work from Joseph Campbell, Ram Dass, James Hollis, Eckhart Tolle, Gabor Mate

Closing thoughts

Thank you 🙏 to everyone that helped out on this one. I’ve been thinking about taking a career break myself for a while now and was never quite sure if my feelings were shared or if I was just being an irrational, ungrateful loner. In that sense, putting this together was as much for me as (I hope) others. If you enjoyed this, please share it with a friend or colleague! At the end of the day, we’re all just standing on the shoulders of giants.