Second Sabbatical

It was hard to return to work after hiking the JMT in 2016. Usually when I get back from vacation, I feel refreshed and excited. I’m not sure why this time was different. Perhaps it was my approaching 4-year anniversary at Sincerely—I had never worked anywhere longer. I had the itch to go off on an adventure, perhaps attempting something like the PCT. There was only one problem: Stephanie had just started her first semester at SFSU, with 2 years to go before she’d complete her degree.

The challenge of staying in sync as a couple (at a macro/career level) had become a recurring theme. Stephanie was ready to quit her job at Federated Media a full year before we actually set sail, and she was again ready to “chuck it all” two years before my post-JMT itch, when she quit her advertising job. In both cases, I wasn’t ready to leap. Now it was my turn to sit tight. That fall I distracted myself in search of La Jeep, and essentially accepted my lot. There was a silver lining: more time working meant more time saving, so I doubled-down on saving as much as I could. But we never really resolved the underlying tension between my desire for freedom and the constraints of her education.

A corporate reorg the following summer (immediately preceding our trip to France) left me feeling unmoored, and ultimately brought things to a head. Captive for eleven hours on the flight home, we went round and round, trying to put words to feelings, proposing all manner of hypothetical solutions. Two remarkable things came out of that experience. We decided to sell our condo—but more importantly, I came to realize that Stephanie’s educational track (and future career) was more important than my own. Hitching my desire for adventure and change to the wagon of her future grad school dreams was a revelation. A weight lifted. I just had to wait one more year for her to finish undergrad.

Enter 2018. Selling our condo meant I didn’t need to worry about immediate job security (or frustration). In the spring, I informed FTD (our parent company) that I intended to leave by the end of August, to sync up with Stephanie’s graduation. However, when I learned that another company had expressed interest in acquiring our apps, I agreed to stay on through the end of the year to ensure a smooth transition. After 6 incredible years, my last day at Sincerely was December 21st.

Gmail app inbox zero: you're all done
“Inbox Zero” on my last day at Sincerely

We have few concrete plans for what’s next. Everything depends on where Stephanie goes to school, and we probably won’t be able to make that decision until the end of February. The incredible thing is that between now and the start of her program (likely in August), our schedules are in sync. We are both free!


Congratulations! It’s such a luxury to not have something planned right away and yet have enough security and future plans to not be anxious about it.


In the day and age when one person was the sole breadwinner and the other partner followed along I love the idea that both of you have formed a wonder-filled balanced ballet of your lives together – sometimes leading, sometimes following.


So come visit us in NC!!!


Congrats man! Wow!

Great to hear, and especially love the frank description of how you discuss and work things out as a couple. So important these days when there are no longer gender-proscribed roles for breadwinning/housekeeping. Let me know if you will be in the Austin area anytime.

Thanks for all the comments and support! Filled in a few details about our plans for the upcoming months in my next post: San Francisco Sunset. Kathleen, unlikely we’ll make it to NC during this sabbatical, but the idea of a pan-US roadtrip to visit our far-flung friends and relatives has definitely come up. Would love to one day!


Incredible picture! Brings a tear of happiness to my eye. Remembering good times fondly and sending you virtual hugs!

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