Sabbaticals and Gap Years

Have you ever considered an intentional period away from work, aside from the usual reasons of stressful layoffs, parental leave or medical issues? The times that I've taken to step away from work have been enormously impactful to my life. I've spoken to many people who are interested in a sabbatical, but held back by a combination of factors that can essentially be summarized as fear. I'd like to take a little time to share my experiences, encourage you if this is a path you're considering, and extend an open invitation to receive questions on this topic.

I've taken three sabbaticals in my career thus far:

• The first was in March 2012, and was six weeks long.
• The second was September 2012, and was three months long.
• The third was in 2019, and though I intended to take around a year off, it lengthened into four.

I was interviewed about the first two back in 2014 with some others that had also taken time off, that article is here. I'll go into some more details in this article, if you're interested in my personal journey.

I'm also going to do a brief FAQ section right up front, since many people have targeted questions.

FAQ

How did you do it?

My first two were unpaid leaves of absence, I did not quit my job and was able to return to work immediately afterwards. For my third and longest, I did resign.

How did you pay for it?

This is much less of an issue if you're just taking a leave, it's like setting aside funds for a long vacation. During my second, it was indeed stressful living in the Bay Area and watching my savings quickly get spent with no money coming in. For the third, I minimized my expenses and restructured my finances before quitting to have investment income coming in monthly (dividends from stocks, ETFs and REITs); after 4 years, I never touched capital and was still cash flow neutral.

Did you have health insurance? How did you cover medical/dental/vision?

Health coverage is definitely a concern, but not impossible. Again, if you're doing this short-term on a leave, you might be able to retain your work coverage, or simply purchase short-term gap coverage if you're really concerned. Either way you'll get it back as soon as your employment resumes.

When I resigned, I used the U.S. healthcare exchange to purchase my own medical coverage. It's scaled for your income, so if you're under certain thresholds, your premiums are reduced. Coverage isn't as good as private insurance, but for the routine care I used it for, it was fine. Vision was easy, online eye exams are about $20 to get prescriptions renewed for glasses and contacts. Dental was the most problematic: network coverage isn't great on the cheaper plans, and waiting lists are long for the more accessible dentists. I suggest finding a favorite dentist, negotiating a discounted cash rate, and paying out of pocket. I did this for my mom as well (her dental coverage under Medicare Part C is terrible), we got her services at about 60% of list price.

I also built up a nest egg in my health savings account, to help cover any unexpected medical expenses.

Did it slow down your career growth during "prime earning years"?

The short ones? No, not really.

The long one? Yes.

There's really no dancing around this one, not working while others are getting in line for promotions will definitely stunt growth.

Were you able to find a job afterwards?

Everyone's situation is unique. In my case, I felt very blessed to end up with three different offers at the same time to choose from.

I know four other people who took long-term sabbaticals (2+ years), and all four also returned to positions within Big Tech afterwards.

Surprisingly, I didn't get as many interview questions about my time off as I anticipated.

Why did you do it?

This is the hardest question to answer succinctly, and it's never just one reason.

I have a general philosophy that life isn't meant to be deferred until old age. Some pursuits can fit inside a standard two-week vacation slot, and some can't. (Europeans have a better perspective on this, in general, than Americans do.) This is partially shaped by two of my early coworkers, Bill and Bo, who died before they ever reached retirement age.

The shortest answers are: boredom/trying something new for my first, taking on a new challenge and career change for my second, and family for my third.

Sabbatical 1: Cultural Exchange Program

After a few years at my first job, I was interested in expanding my skills, and joined a Masters program. That kept me busy for a while, but after graduating, I was looking for the next way to grow outside of work. I joined a Young Professionals group, and was volunteering at some of their fundraisers, when I noticed an advertisement from the local Rotary Club looking for applicants to a "Group Study Exchange". This was advertised as both a cultural and vocational exchange program, where we'd get to meet others overseas in similar professions and tour the country visiting different Rotary Clubs. Professionals age 25-40 were eligible to apply, and if accepted, travel, room and board were all provided. I applied and was accepted along with four others who'd be in my cohort. (Looking at you, Tiffany Paine-Cirrincione, MID and Nikisha Ridgeway !)

In practice, this program was much more of a cultural exchange (i.e., just learn from living with your host families, and be a nice American) and a recruiting tool for Rotary to try and pull in younger members. I had a great time, however, and have so many stories and memories from this period of my life. I spent one month traveling all over the Philippines, with two other weeks of personal travel: Singapore for a weekend, to visit my old college roommate and his wife, plus Dubai and Abu Dhabi for a week on the way back, to visit a colleague and his family living there as ex-pats.

Sabbatical 2: Startup School

After returning from my trip, I was still restless at work and trying to decide what I wanted to do next. I'd been researching how electronic devices could help broaden access to free educational materials, had a hardware prototype of a solar-powered Kindle, and got to conduct some research at a school while I was in the Philippines. I wanted to explore taking this idea further in a startup, and recorded a video application to the Founder Institute, a business accelerator in Palo Alto. I got accepted, and had to make a pretty rapid decision if I was going to go. I'd have to take another three months off work, less than half a year after I'd just taken unpaid leave. How would they receive it? If it was denied, did I have enough conviction to quit for this?

I decided to go, and my leave of absence was approved (though with unpaid leave, there's no guarantee your employer will take you back afterwards). I spent a couple of months sitting at Wilson Sonsini every Tuesday night listening to other founders presenting on topics like pivots, raising venture capital, corporate structure, and pitching ideas to a panel Shark Tank style. During the week, we were talking to advisors, helping our teams, and working on our ideas. We had weekly challenges that weeded out participants; by the end of the first month, our class was already half the size.

Two months in, we had to incorporate to go to the next phase. This was an inflection point for me: did I really want to continue pursuing this startup idea as a sole founder, did I want to jump to another team to support them (I had an offer to do this, along with a $50k yearly stipend to cover my living expenses), or did I want to return to corporate life? As positive as I found this experience, I decided I wasn't ready for a startup with this idea, and withdrew from the program at the end of the second month. I used the third month in California to job hunt for something new and different, interviewed for a new role in Seattle the day after Christmas, and accepted in January. I returned to my old job for just six weeks before resigning.

Sabbatical 3: Family / "Life"

By 2019, I'd been on the West Coast for almost 7 years, while my family was all back east. With limited vacation time and no real ability to work remotely in my field pre-covid, at most I got to see them for a week in the summer and a couple of weeks around Christmas.

That wasn't enough.

I enjoyed my work, and living in California, but as my parents approached 80, I became increasingly convicted that I should prioritize spending time with them while they were still in the condition to enjoy it. They didn't yet need care-giving in a medical sense, but they'd benefit from a little extra looking after.

I don't have a cool "North Star" moment for this time off, like living in a castle on a tropical island, so I'm self conscious that it's boring to recount. Yet the time I had to connect with my family and re-connect with old friends all over the U.S. was really special.

A short list of activities:

• Driving most of the CA coast along Highway 1
• Ten days driving cross country with my niece
• Visiting family and friends across the East Coast, from NY to Florida, and meeting all of my friends' kids
• Being present for birthdays, weddings, and job changes
• Taking my mom and sister on their first cruise (and my mom to visit Times Square, 60 years after her last visit at 19)

The mundane:

• Fixing a leak on my parents' house the first week I arrived home (on a very steep 11/12 pitch roof)
• Lots of remodeling projects to stay active during covid
• Driving to shopping and appointments, fixing technology, cooking meals

Family time: Lots of eating, playing cards on the weekends, games, fishing.

The unknowns I was present to help with:

• My mom tripping and fracturing her hip in August 2022, just a few weeks before my nephew's wedding. This was a difficult period but she recovered quickly with all of our help.
• Mom again, labored breathing that became a heart arrhythmia in Fall 2023. A cardioversion shocked her heart back into rhythm and she's been well since.

The last, and most important unknown: years of extra time spent with my brother-in-law, Bill King, who was diagnosed with cancer in September 2023 and passed away on July 12, 2024. I'm very grateful for the time I got to spend with him, not knowing what was coming.

Returning to Work

This section could be an entire article of its own, but there were a couple of main contributing factors.

One, I missed working, especially work in an office with the socialization of coworkers. This is one reason I waited until return to office was happening in full force, I personally enjoy it.

Two, many tech companies shifted to officially allow 4 weeks of remote work per year, from anywhere. This was a game changer for me. No longer would I have to choose between seeing my family or having a break, using up all my vacation time to fly cross-country or missing my relatives. I could have time off AND still see my family in longer chunks of time.

What's your Why?

Have you thought of taking time off to pursue something big? What does that "What if" look like for you? It might be more attainable than you think.

If your plans can fit inside a shorter period (e.g. 12 weeks), and you have a good relationship with your employer, an unpaid leave of absence might let you achieve all your goals in a low-risk way, without leaving your career behind.

Taking the leap to quit and pursue a long-term break is definitely scary, and something to carefully consider. However, for myself and those I know that have done it, there are no regrets.

Thanks for reading, I hope this was encouraging or informative for you. If you're considering time off and have questions about my experiences, please feel free to contact me here via Messaging or by email.