How to Quit (or take a break)

One might argue that it’s harder to quit than it is to start. Quitting is deciding to stop doing something that was initially worth your time and energy - that you were probably pretty excited about at one time. And then something changed. Maybe You changed. Or was it the job? . . . All that matters is that you don’t want to be doing what you’re currently doing. Period.

It’s fascinating how often we arrive at this decision and yet don’t end up quitting. We keep doing the thing that’s making us unhappy or sick because it’s easier to just keep on keepin' on, we tell ourselves. And for the short-term it absolutely is.

Quitting is Daring

Someone once told me that quitting inevitably involves hurting someone’s feelings. And unless you’re a robot, that’s a difficult thing to do. Even if you're quitting a habit that you've deemed unhealthy - you risk disappointing the people you shared that habit with.

Quitting requires making a bold statement. Where starting can sometimes mean “I’ll just try this on and see how it fits". . . quitting can mean “No, I'm certain this doesn’t fit.” And you’ll inevitably have to defend your stance over and over with direct challenges and casual asks, requiring a certain amount of mental fortitude. (It's also difficult to explain why you're quitting when you have nothing else lined up, but I can assure you - quitting and not doing anything is a valid plan.)

Be True to Yourself

When I quit my job in 2021, I found that I would tell half-truths about why I was quitting. I would say something like "I just need to take some personal time off" or "I'm burnt out." Yes, these things were true. But the overarching reason was that I wasn’t living a life that was true to myself and I had been doing that for so long, I was beginning to feel unwell. I was riddled with anxiety, having a hard time sleeping, and going days without laughing... taking time off was the solution to a problem I could feel with my whole body but couldn't yet put into words.

My moment of clarity (or breaking point) occurred in a campground in Bryce National Park, in September 2020. It was near the end of a two-week vacation, the longest I'd ever taken. Sitting in the grass after a hike, I felt the most calm I had ever felt in my entire life. (I get goosebumps just thinking about it.) I realized then and there that I had to make drastic changes to my life. I couldn't bear the thought of continuing on the same trajectory. I wrote a note to myself and vowed to quit my job within 6 months and leave Houston forever. (I quit my job 9 months later.)

Make the Decision

To quit, you have to first make the decision. Like really make the decision. This typically involves trying on the decision in your mind for a while (although some people have events that bring instant clarity, like a near-death experience.) Finally, you say it out loud to yourself or write it down. You start to gain resolve around the decision - fully understanding why you need to quit, not just want. Until finally, you speak your truth to others and you execute the decision. Actually quitting is hard no doubt, but knowing that it's bringing you closer to a life that's more true to yourself will help you push through the difficulty.

The Logistics of Not Working

Several people reached out to me on LinkedIn after I posted about my return to work, asking about the nitty gritty details of taking time off. So I'll do my best to describe how I prepared for my mini-retirement. Let me preface this by saying that my risk tolerance is probably a bit higher than the average person's. I know this because I lived without health insurance for almost 3 years while also skiing, mountain biking, trail running, etc. Some might call this stupid . . . I would also call this stupid(ly optimistic regarding my health and very low propensity for injury) and also an unfortunate circumstance of living in America and having insurance tied to your job.

Health Insurance

When I applied for health insurance at Connect for Health Colorado, my lowest-priced option was around $500/month. I believe this was because they based it on my previous year's tax return, where I had worked full-time for the entire year. (So when I applied in December 2021 for health insurance for 2022, they looked at my salary from 2020, not my salary from 2021 where I worked half the year.)

So I politely declined and decided to live dangerously. Then when the next year came around, I simply missed the deadline 🤷🏻‍♀️ When I did apply for health insurance through Colorado in January 2024, I was finally approved for $100/month. I had this health insurance for exactly 1 month before starting my new job.

Let it be known that COBRA does exist, although I didn't take advantage of it. For your specific state, google "Affordable Care Act" and the name of your state to find publicly available insurance in the US. The process of searching for insurance is quite seamless, although beware of the price tag.

"Retirement" Fund

Let me start by saying, you will never have enough money to retire. I repeat: You will never feel like you have enough money to quit your job forever. Because once a magic retirement number is decided and then achieved, most people don’t quit or retire. The goalposts move to a new goal. Why? Fear. But also because our minds trick us into thinking more money equals more happiness, when we have copious studies that prove otherwise.

This seems similar to the uncertainty surrounding the "best time" to have a baby. No one is ever ready. It's always a leap of faith, no matter the circumstances.

That being said, I’ve never heard any retirement or wealth planner say you need less than $3 million to retire . . . And here’s the part where I tell you that I absolutely did not have that much money when I quit my job. However, I did start saving and investing the moment I graduated college (thank you IWT) and it has made me feel more financially free than I ever thought possible. By that I mean, I had at least 20 years of living expenses in the bank.

Although I don’t follow the FIRE movement, Mr Money Mustache has some intriguing advice on how much money you need to retire. He recommends calculating your retirement number by:

💡

$ needed to retire = annual spending x (20 - 30)

Yes, he argues, it is that simple. You'll quickly see that the lower your annual spending, the sooner you can retire (which I believe is the whole basis of the FIRE movement.) I multiplied my annual cost of living by 25 and was elated to find I (almost) had this number in my bank account. Therefore, I felt comfortable quitting engineering for the foreseeable future.

Length of Not Working

In the end, I took off way more time than I and all of my peers expected. This is probably because I intentionally didn't have anything lined up and not even an inkling of what I wanted to do next. I also had no deadline for myself of when I would return to work. I treated it as an indefinite retirement.

Knowing that it took me almost 2 months just to decompress and have the work-induced anxiety fully dissipate from my body, I would encourage people to take off more than that to reap the full benefit. Matt Mullenweg who founded WordPress encourages his employees to take a 3-month sabbatical every 5 years and that's probably the most generous sabbatical offering I've heard of, at least in the US. (Matt also describes a sabbatical as a mini-death, where you prepare your co-workers to work around and without you, while you're gone, and I can't stop thinking about how that should actually be the status quo - no company should be completely derailed if an employee leaves or takes a break.)

Another option is to quit your job and ask for it when you're ready to come back. (I know a couple people who have executed this successfully.) In the end, one of the lessons I've learned from my break is that work will always be there; there will always be more opportunities that come your way. (Yes, in this economy.)

Everyone’s relationship with money is different, and everyone’s tolerance for risk is different. However, I'm confident that if you can find a way to take a significant break from work to do whatever it is you want or need, you will not regret it. Goodness knows I haven't; it's been the biggest and best turning point of my life.