Sabbatical Stories

Ryan’s Bucket List Adventures

Gap year of adventuring, parenting, and writing to find new purpose in my career

After 20 years in enterprise software, it was time for a sabbatical… to tackle some of the adventures on my bucket list, including the unplanned adventure of my boys’ online education. It was time to spend more time giving back to the causes I care deeply about. And it was time to take a few steps towards becoming an agent for change, using technology and community to help the world prepare for our biggest challenges.

Describe any changes you made in your life post-sabbatical:

I know that I ended my sabbatical as a different person than the one who started it, even if the mountain I’m climbing post-sabbatical is similar to the one I climbed before.


What catalyzed your sabbatical?:

I was in a season of life where everything was going great on the surface, but not so much underneath. I was quietly being re-orged out of my role. I had recently lost my father, my first role model for the “good life,” after a long battle with alcoholism and dementia. Success, Failure, Loss: I felt like all three of these things were happening to me at the same time. I was entering a valley. I needed a sabbatical.


List some activities you engaged in during your sabbatical: 

Changing, Learning, Writing, Biking, Backpacking, Mountaineering, Snow-shoeing, Skiing, Volunteering, Fundraising, Coaching, Road-tripping, Parenting, Barbecuing, and Dog-adopting.

Tell us about your sabbatical: 

My sabbatical started with the pandemic– my projects at work were canceled and I started wondering what my teenage boys were doing all day during their “online learning.” I decided to take some time off, focusing on family, adventures with my boys, and developing a sense of purpose to fuel the second half of my career.

I committed to sharing what I was learning with my LinkedIn community, and raise some money to help kids get outdoors as part of a Mt. Shasta fundraising climb. Although I never expected to take a full “gap year”, one adventure led to the other and I was learning and growing the entire way. Not everything went according to plan– I failed to summit Mt. Shasta, failed to complete the Death Ride, failed to circle the Tahoe Rim Trail, failed to complete the Collegiate Loop, and failed to discover some magical new career. But my sabbatical was perfect… because of whom I was becoming.

Ryan's sabbatical has him on a hiking adventure with his sons
Describe the impact of your sabbatical in one sentence: 

I’m now committed to becoming my “next mountain” self, the person that I was discovering over my period of sabbatical: Who is in constant search of a cause bigger than me. Who gives in order to grow. Who is always seeking to know myself better. Who learns from all of life’s journeys. And who views both victories and defeats from a position of humility.

How long was your sabbatical (in weeks)?



Why do you think others should (or shouldn’t) take sabbaticals? Are there occasions in life where it’s particularly helpful?

Maybe you’ve dreamt of taking some time between things to take a step back and reflect, and are afraid you’ll never actually do it. Maybe you remember being told “never leave a job until you have a new one.” Maybe you worry about what it will “look like” to push out a start date, or have a strange gap on your resume. Maybe you worry about the financial insecurity. Maybe you worry if you’ll actually enjoy spending more time with the kids, or if they’ll enjoy spending more time with you. Maybe you worry that you’ll get bored quickly, without a day job. Maybe you want to write, but worry that no one will want to read. That was me. All of it.

So I decided to take one, and learn and write and share about topics I cared deeply about: knowing when it is time to move on from a job that you love, how to give as you go, how to broaden your search to include the proverbial “second mountain,” and the power of an outdoor pilgrimage as part of this process. I don’t have anything close to all the answers to these questions, but decided to jump in and share what I was learning. If you are thinking of doing anything along these lines… go for it!

Ryan and his sons on an adventure, hiking up a snowy mountain — parent with 2 boys
60 Awesome Moments from my Sabbatical
  1. Driving down Baja without a work worry
  2. Heading to Park City in the days before the total shutdown
  3. Hiking Big Basin before the summer fires
  4. Family tournaments: outdoor games, board games, card games
  5. Adopting Jax
  6. Road biking to the ocean every few weeks
  7. Desolation Backpacking with Jax
  8. 20 mile hike to Mt. Rose
  9. Spending July in Tahoe
  10. A week in Coronado Beach
  11. Starting a “backyard cocktail” tradition with friends
  12. Orange Skies in the Bay Area
  13. Spending a weekend solo in a Teepee
  14. Backpacking Alamere Falls with my Son
  15. Writing postcards for Biden
  16. Canyoneering with my Son in Capitol Reef
  17. Biking Moab
  18. Solo backpacking the Escalante Route of the Grand Canyon
  19. Maui Road to Hana
  20. Outdoor thanksgiving
  21. San Francisco walking tour with the family
  22. Christmas on the Lost Coast with the boys
  23. Tailgating Northstar
  24. Spending January Skiing, Hiking, Snowshoeing in Tahoe
  25. Hiking and Skiing Sawtooth Ridge
  26. Tahoe Spring Break with My Son: Snowmobiling, Snowshoeing, Cross Country Skiing
  27. Palm Springs / Joshua Tree with extended family
  28. Birthday bike ride to Zotts
  29. Nevada Falls hike with my best friend
  30. Biking Tioga Pass Road closed to cars
  31. Camping & Biking with our Life Group
  32. 20 miles hike through Purisima
  33. Preparing a summer’s worth of backpacking food
  34. Attempting Mt.Shasta with my brother
  35. Backpacking Lassen National Park
  36. Camping with the Family in Black Sands
  37. Backpacking the Lost Coast with my Boys
  38. Volunteering at Camp Royaneh
  39. 20th Anniversary Week in Healdsburg
  40. Anniversary Dinner at Singlethread
  41. Backpacking with family friends in Desolation
  42. Boating around Lake Tahoe
  43. Doing Training rides up Mt. Baldy
  44. Attempting the Death ride with my bud
  45. Attempting the Colorado trail with my son
  46. Rafting the Arkansas
  47. Reliving Blanco Basin & Durango with My Son
  48. Backpacking Chicago Basin, Climbing Mt. Eolus 14er with my Son
  49. Finishing a home remodel
  50. Spending a day brainstorming business ideas with my brother
  51. Getting together with old friends
  52. Showing my family DC
  53. Showing my family NYC
  54. Graduating from MEA
  55. Doing Executive Coaching with Chris – Finding My Mantra
  56. Volunteering at Second Harvest every week
  57. Raising thousands for BAWT in their AWK fundraiser
  58. Posting every week on LinkedIn
  59. Being there for my step-mom after her stroke
  60. Weekend with a group of guys with whom I have no secrets

You can check out Ryan’s articles here!

Interested in more stories of people leaving corporate roles to take sabbaticals? Check out Renee’s story here.

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