Jared White Photo of Jared

Expressively publishing on the open web since 1996.
Entranced by Portland, Oregon since 2017.

Why I Regret Not Taking a Sabbatical When I Was 25

I needed to take some time off work to think, to dream. Instead I listened to the advice of family and friends and charged into a new business opportunity. Was it successful? Was it an utter disaster? Read my story to find out.


This essay is over four years old. It's possible my views have changed since I first wrote this, but I choose to leave it online nevertheless. Cheers, Jared

A fascinating question turned up on Quora entitled Should I quit my job to rest? As it turns out, I have some thoughts about that. Here’s what I wrote in answer:

If you have enough savings and a reasonably concrete idea of what you want to go for, then I would say you can definitely take some time off between jobs. When I was in my early 20s I had a decent amount of savings and had been working steadily since my teens, and I felt like I desperately needed a month or two sabbatical to wrap my head around the next phase of life and the values that were most important to me. But I let family and friends talk me out of that, and unfortunately it directly resulted in a disastrous string of career-related decisions that took years to undo. I only somewhat recently began to feel like I’m fully past that mess and on the right path. Of anything I’ve ever done or not done, I regret not taking that sabbatical.

I’d like to unpack some of this in further detail here on the blog, not only because this references one of the most pivotal moments in my life, but because my hope is that others don’t end up making the same mistake I did.

Jared White, Cubicle Dweller

When I was in my early teens, I embarked on the career path of performing and recording Celtic music (shockingly, I actually made some real money doing this), as well as designing websites. Being an artist and a creative freelancer suited my personality and my drive well, and I flourished during this period of blossoming into adulthood.

Fast forward to my early 20s. I was ready to move into a place of my own, and in particular I was yearning to set up a fully-fledged music project studio. My parents were of the opinion that renting a house made little financial sense, and they offered instead to assist me with a down payment to buy a house. But in order for me to afford the mortgage payments, I’d have to leave freelancing behind and get a full-time job.

Thus I became a salaried employee at a tech consultancy and joined the ranks of cubicle-dwellers. The very thing I swore I would never do, I did. My earlier teen-era conviction that I’d never become one of those 9-5 office workers sitting under florescent lightbulbs day in and day out proved to be nothing more than shouts into the wind.

It Was Great, Until It Wasn’t

Less than a year after I officially joined the workforce, my mom passed away due to cancer. Because my professional music career had been fully intertwined with the family band my mom had founded, I lost both my mom and my musical world in one fell swoop. I had been pretty involved in a local church for a while and it had become my primary support mechanism, so it should come as no surprise that my coping mechanism to deal with the loss of my mother was simply to put all my waking efforts into work and church. If I wasn’t working, I was at church. If I wasn’t at church…well, I was probably working.

For a time, I did all right. I learned a lot as a technology consultant. I gained a variety of useful skills, and I even ended up being placed at BabyCenter (based in San Francisco) which gave me a good taste of the Bay Area startup scene. It’s not a scene I’ve been particularly keen to revisit ever since, but I value the time I spent there.

After a couple of years of cubicle-dwelling and commuting regularly, I was feeling burnt-out. My career trajectory was not headed in the direction I had envisioned for myself. I wanted to get back to creative direction, to working with a diverse array of clients (not just a single large enterprise). I needed enough “margin” in my schedule on a daily basis to pursue artistic projects on my own terms. I wanted my life to be defined by far more than the concept of simply being a “computer programmer for hire.”

I decided to take a sabbatical.

I’d recently come into a bit of money from an unexpected inheritance—not a huge amount, but large enough that I could easily take a month or so off work and still have plenty left over. It was January just after the holidays, and I figured business is often slow this time of year anyway. If there were ever a time when everything appeared to come into alignment to afford me this time off, it was now.

The Intervention

“We want to come over and talk with you.” It was my dad and my step-mom (he had just recently remarried) along with my church pastor. At the time, my pastor was a major authority figure in my life and someone I respected greatly, and my parents…well, they were my parents. So how could I refuse?

Needless to say, they tried to talk me out of the idea of taking a sabbatical. A few days off, sure, everybody does that — but some extended period of time seemed reckless and irresponsible. Not only that, but I had only recently started dating the woman who would later that year become my wife, and at that time they felt I would be sending the wrong message to her. Perhaps she’d conclude that I’m a flaky dude who can’t keep his head down and get the work done.

Other elders at my church encouraged me to stick with my job even if I was unhappy (apparently working at a job you hate for decades is a badge of honor for some people). None of my immediate friends proved sympathetic to my cause…they were all still trying to figure out college life and how to make a few extra dollars working side jobs. The concept of “young man who already owns a house, has a large savings account, and desires to take a month off to contemplate his fate” was just too foreign, too ostentatious.

So with literally no mentor or close friend at hand who would tell me “go for it! Take some time off. Work on yourself. Decide what your values are. Determine the ideal career path you really want. Write out a detailed plan of how to get from Point A to Point B. Dare to dream…” — well, I capitulated. I canceled my sabbatical. I did take about a week off, but that was only long enough to catch up on bills and laundry and decompress after all the work and holiday hoopla from before. Then it was back to the daily grind all over again.

I Got Married. And Then Everything Unraveled…

The rest of that year proved to be nuts. I got engaged, and then I got married. The planning and execution of the wedding and everything surrounding it took up all my mental and emotional bandwidth. When it came to work, I was on auto-pilot.

Soon after becoming a married man, I ended up forming a new web design agency as a “subsidiary” of the tech consultancy I was a part of. They knew I wasn’t super happy with the kind of enterprise software work I had been doing, so they were willing to give it a shot to support the smaller-scale web design clients I wanted to work with again. At the time this seemed like a reasonable compromise, and I felt I should be grateful for their proposal.

It proved to be an utter disaster. It wasn’t long before the consultancy was running out of money, partly due to the new markets I was pursuing but mainly due to losing some large enterprise contracts. Other people in the company had not taken the time to train and learn the ropes to join my web design subsidiary, which meant I was still a lone wolf in that department. In a rare moment of clarity and courage, I decided it would be foolish to wait until things got completely out of hand. It wouldn’t help the company to stick around, and I was stressed to the breaking point. So I cleared my throat and announced my resignation and intent to pursue independent work as a freelancer.

They did not take the news well. Rather than perceiving my actions as an well-intentioned attempt to relieve them of the burden of subsidizing my web design business any further, they saw my actions as a rat cowardly leaving a sinking ship. I had “betrayed” them and the cause. This in spite of the fact that I had actually made them an offer to purchase the rights to continue servicing a couple of clients on my own. If I were truly a rat, I would have just left without explanation and then contacted those clients directly to bring them over to my new business. But I wanted everything to be on the up and up.

Long story short, in the midst of all this turmoil, I launched my new freelance career and started my business tens of thousands of dollars in the hole. At the same time, there was a lot of behind-the-scenes drama with my church and immediate family members as well which won’t go into here. Suffice it to say, I had finally struck out on my own, yes, but I was walking on very shaky ground and felt alienated by everyone around me.

I didn’t have an adequate support network, nor did I have a fully-fledged idea of how I would grow my business. All my energy had gone into the act of becoming a freelancer again, and now I had to figure out how to make that work as a full-time job. My wife tried to be supportive as best she could, but this was a lot of strain to put on a new marriage. The next couple of years proved to be among the most difficult times in my whole life.

Years Later, I’ve Been Able to Put the Pieces Back Together

Since that dreadful sequence of events, I’ve made a living as a freelance web designer and software developer. I’ve created two startup products (one failed, one currently in development). I’ve composed and recorded lots of new music in the electronica genre. My wife and I have had kids—the two most adorable little girls in the entire world. We’ve moved to another state (Oregon) and have gone through many other transitions. At this point, I feel like I’m finally living a life congruent with my values and my priorities. I have margin to pursue creative projects, like my podcast. I enjoy working with my clients. My business has had many ups and downs, and finances are often challenging (all my inheritance had ended up funding our wedding/honeymoon and then subsequent business investments when I went freelance). But despite that, overall I’m excited about where my career is headed. I absolutely love living in the Portland area, and I’m having a blast going on fun family adventures every weekend.

Yet I often reflect back on that year when I almost took an extended sabbatical. I wonder what would have happened if I had taken the time off to plan, to dream, to listen to my heart. Maybe I would have started my web design company then, when I had way more money in the bank and more options for how to proceed. Maybe I would have decided to pursue a different career entirely.

I know it’s dangerous to get caught up in all the “what-ifs” and imagine doing it all over differently. But I can’t help but feel that the series of mistakes I made in my thinking and my decision-making leading up to that “horrible year” was a direct result of my lack of clarity and focus. I didn’t really know what I wanted to do with my life. I didn’t have a solid strategy. I didn’t take the time off to get my head on straight and chart a course forward. And instead of taking life by the horns and making good things happen, life happened to me. I got completely swept overboard, and barely made it back to shore relatively unscathed.

In the words of James Altucher: “Choose Yourself”

There comes a time—and probably many times over the span of a lifetime—when you have to make a choice. You have to draw a line in the sand. On the one hand, it’s what other people want for you, what other people expect you to do, what other people say is the “right thing” or the “responsible” path. On the other hand, it’s what you want for you, what you expect you to do, what you say is the right and responsible thing for you to do because deep down in your gut you know it to be true.

When that time comes, don’t hesitate. Choose yourself. Yes, you might feel selfish. You might feel cruel. You might feel like you’re letting others down. You might even feel like you’re letting God down. But believe me, I’ve been there. I’ve made both kinds of choices. And I’ll tell you this: as painful as it is to choose yourself in the midst of difficult circumstances, the opposite is far more painful. I’ve never regretted making a decision based on what my instincts tell me is right. But when I’ve capitulated and let others talk me into taking the course of action they think is best, it has usually ended in disaster. Those are the times I regret more than anything else.

I hope you’re not facing this kind of choice right now. But if you are, I hope you’ll consider my words and my story. Don’t make the same mistake I did. Deep down, you know what you want. You know what your life’s all about.

So go for it.


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