• I've worked on the web since it's been possible, typically for start-ups, agencies, and new product groups where everyone wears a lot of hats. Nearly every role has been a hybrid of UX / visual design, content strategy, and marketing. I love clean, artful, scalable information design that makes it easy for people to do what they want to do. (And what you want them to do.) I'm a strong team lead, mentor, and an exceptional verbal and visual communicator.

How to Sabbatical, Pt 1: Jump Off the Train

This article was originally published on Medium.

Last summer I did one of the scariest things I’ve ever done: I quit my job to restore my health, live my dreams, and find my way to my next professional life.

Spoiler alert: It worked.

I figured out how to do it and got the courage and inspiration to do it from others’ stories, so I’m writing this in the spirit of paying that forward to you.

Jumping off the train

My identity, in more ways than one. (And yes, that is Comic Sans.)

I do not take employment or financial security for granted. I come from a refugee family, and as an adult have myself lost everything twice — in a recession and from a health challenge that made me think I’d never work full-time again. I do not jump easily.

I’ve also always strongly identified and defined myself by my profession, for better and worse. The times I thought I’d lost my career and livelihood shook me to the bone. Those times I did not choose. To choose it now and risk it? Terrifying.

So how did I buy my freedom? And how could you? The logistics are maybe another article, but I’ll just put this here: I worked a lot, paid off debt, and saved money. I’d even sold my home the year before to have some professional freedom and general peace of mind. My girlfriend and friends were emotionally supportive. And I do not have children or pets, though people with these take sabbaticals, too.

For further practical info, may I direct you to this fine book, which I used to build my courage and plan my own sabbatical: Reboot Your Life: Energize Your Career and Life by Taking a Break.

For further inspiration on why and how this can be a sane, constructive, and game-changing thing to do for your life, check out this TED Talk: Stefan Sagmeister: The power of time off.

The Powerpoint slide that made me quit my job. (via Stefan Sagmeister)

Why I did it

I could. I wanted to. I needed to.

I’d been working hard at a breakneck speed for over 5 years at a famously hard-driving (and exciting) company. Vacations were rare, short, and usually taken nearby or at home. The health breakdown I’d experienced years earlier was triggered by a similar pattern and I could feel it on the near horizon again. Burnout was nigh.

Me as a stock photo on Amazon Careers site.

I’d just passed my 5-year anniversary at the company, which I’d had in my mind’s eye as a point to maybe move on. While my job as a designer was intellectually challenging and interesting work, in many ways I felt in a rut, with neural patterns carved so deeply in my mind that I glided all too easily on their tracks. My work brain had become the default, and I wanted to feel my creative mind outside of that environment and identity again. I changed my computer password to have this in it: freeyourmind. As in the glorious 1990s En Vogue song: Free your mind / And the rest will follow.

Also, in recent years, I’d seen several friends about my age become very ill or die. As their days or health diminished, they tried to do everything they’d ever wanted to do. I didn’t want to wait until I was old or dying to do what I’ve always wanted to do. If I didn’t seize this opportunity now when I finally could, I’d never forgive myself. I finally had it all at once: health and money and now, if I dared — TIME.

The crash

Just prior to leaving my job, I was giddy with plans, still riding fast on the pace and adrenaline of my daily work life. There were a million things I’d do immediately after leaving: write an Ignite (or TED) talk, volunteer at the photography center and JCC, go to every event I’d been too tired or busy to go to, see all my friends constantly, make smoothies every day and, of course, exercise all the time and get super fit.

What happened? I slept and hid out and cleaned my apartment, and had at any given time 20+ tabs open on my browser to Expedia, Pilates classes, and health insurance options. (Thanks, Obama!) I slept and slept and slept. I enjoyed being home and losing track of days. I slowed down insofar as my temperament is capable. I did not set an alarm. I ate when I wanted. I kayaked on weekdays. I saw two friends, a lot. Time was strange and unwieldy. I freaked out. What have I done? And the only thing I stretched was my imagination: WHAT NOW.

Setting the stage

Travel would be the core of everything. Any physical, spiritual, or creative exploration would happen through it. It was my framework. And I’d wanted to travel around the world my entire life. I always thought I’d do it my 20s… then 30s… and then and then… nada. So you better believe it was going to happen now in my 40s. This is it.

Other than this, I set as my intention: Follow your passion for travel and photography and feast on the most beautiful things in the world. See what happens when you take the considerable time and energy you’ve put into your job in the prime of your life into your creative work. Follow that drive. Improvise. Seek out beauty and excellence. Find inspiration and let it inform what work you want to do in the future.

Around this time, I was coming back to life creatively: I had more time to walk about feeding my love of street photography, and I started writing articles on Medium on topics that it inspired in me, like public privacy. I’d suddenly be consumed with a need to write, and I’d sit sweating in my hot west-facing summer apartment all day with words pouring out of me, forgetting to eat and totally in the flow. To my surprise, most of these articles were picked up for reprint in online photography magazines. It was heady and thrilling, and also deeply vulnerable, as the work out there being praised and criticized could not be more personal: my words with my photos. As a designer, critique is central to my professional life, but this was a new and powerful exposure. I could feel my voice growing stronger.

It was July 2016. I’m obsessed with Japan and knew I wanted to go there for a month(!), so I just sort of picked a random set of dates post-monsoon and pre-cold weather (and the U.S. election): September to October. Then I randomly found a must-must-must-have Airbnb rental, that was non-refundable, and just went for it. There. I was doing it. This was happening. Omg.

While still employed, I’d already planned (and paid for, thankfully) a vacation to Iceland with my girlfriend in August. One day I was researching and looking at a map of Iceland and zoomed out a bit: Europe is right there. A few cheap-o discount carrier flight searches later, I decided: Fuck it. I’m not coming home after Iceland. I’m going around the world.


Stay tuned! Coming soon: How to Sabbatical, Pt. 2: F*ck It, I’m Going Around the World and How to Sabbatical, Pt. 3: What I Learned + Re-Entry.