Life Goals

I started this goal list at age 20, inspired by Jim Wiltens. Completed goals are in red.

A few notes about my method:

  • I only post big, exciting, and slightly intimidating goals—not the little stuff.
  • I may retroactively add goals I’ve already completed, even they weren’t “goals” to begin with.
  • I may remove goals that become irrelevant. (The list isn’t sacrosanct.)
  • I post my goals publicly because I believe that publicly sharing goals gives me a better chance of completing them. (Others disagree.)
  • I post failures as well as successes. (Thanks, Tina Seelig.)
  • I link to digital evidence of completed goals whenever possible.

[Last updated: Feb 2024]

Traditional Goals

  • Start a family
  • Get a dog
  • Graduate from collegeB.A., UC Berkeley 2004

Writing & Speaking Goals

  • Blog every day for a year – failed in 2011 and 2013
  • Hand-write a letter or postcard to someone every day for a year – failed in 2015
  • Write the first draft of a 50,000-word novel in one month (the NaNoWriMo challenge) – failed in 2006 & 2009
  • Do a speaking tour in the U.S.2018
  • Publish a book about going to college without high schoolCollege Without High School, 2009
  • Publish a book about giving yourself a higher education without college – Better Than College, 2012
  • Publish a book about self-directed learning – The Art of Self-Directed Learning, 2014
  • Give a TED talkTEDx YouthDay Palo Alto, 2010
  • Publish 10+ original audio or video episodes onlineOff-Trail Learning podcast, 2015
  • Speak in Europe – 2017, 2018, 2019, 2021…
  • Independently publish a professional-quality book – Better Than College, 2012
  • Give away 10,000 digital copies of Better Than College – 2014

Work Goals

  • Create a brick-and-mortar “school” (i.e. long-term structured learning program)
  • Teach an online courseSelf-Directed Learning 101 (2020)
  • Earn passive incomeLaunchpad (2017) + book sales via Amazon (2012)
  • Start an international trip leading companyUnschool Adventures, 2008
  • Create a leadership program for homeschoolers – Homeschool Leadership Retreats, 2010 (merged with U.A.)
  • Direct a summer campDeer Crossing Camp Deputy Director, 2008
  • Run a “how to do college without college” program – ZTC Camp 2011
  • Organize a conference – Trailblazer Gathering, 2013
  • Run an Unschool Adventure trip without me on it – UA Writing Retreat + New Zealand 2019
  • Work at Not Back to School Camp – Advisor, starting 2006
  • Work as a summer camp cook – Deer Crossing Camp, 2008
  • Lead a workshop at a major homeschooling conference – 2009
  • Be self-employed for a whole year – 2010
  • Work a full season at a ski resort – Heavenly Ski Resort, 2007

Travel Goals

  • See the Aurora Borealis with Matt & Patrick
  • Travel the world with a girlfriend for 6+ months
  • Live abroad with child(ren) for 12+ months
  • Live in the California Sierra Nevada for one year straight
  • Live in Lake Tahoe – 2007
  • Live in Portland – 2009
  • Live in Buenos Aires – 2017
  • Live in New Zealand – 2019
  • Live in San Francisco – 2014
  • Live in New York City – 2019
  • Live in Europe – 2020 (Germany)
  • Live in one place for one year straight – Asheville, NC, 2012
  • Go on an expedition with Jim Wiltens – tree climbing expedition in Guatemala, 2011
  • Explore the Himalayas – India (2011), Nepal (2014 + 2019)
  • Explore South America – 2007
  • Explore Western Europe – 2002

Outdoor Goals

  • Cycle the Carretera Austral2024
  • Thru-hike the Bay Area Ridge Trail2023
  • Thru-hike the Pacific Crest Trail – failed in 2005
  • Do a long solo ramble (a la John Muir) in the High Sierra
  • Slow bike trip around the Bay Area with 100% Warmshowers hosts
  • Walk a 100′ slackline and a high-line
  • Fast-pack the Tahoe Rim Trail – 2021
  • Do a long bike tour2020, 2021, 2022
  • Day-hike Mount Whitney2017failed in 1998, 2006, 2016
  • Hike the Te Araroa (NZ) – kinda, 2019
  • Thru-hike the Sierra High Routemostly, 2018
  • Hike the Southern Sierra High Routemuch, 2019
  • Hike the Camino de Santiago – 2017 (Norte/Primitivo)
  • Run 30+ miles on trail – 2015 (John Muir Trail), 2016 (Tahoe Rim Trail)
  • Run 26.2 miles on trail2014
  • Run 13.1 miles on trail – 2010 (Asheville, NC)
  • Windsurf in the Columbia River Gorge2014
  • Backpack the Lost Coast (CA) – 2015
  • Roll a kayak – 2003

Experience Goals

  • Do a 10-day silent meditation retreatdid half in 2019
  • Dance with a stranger in a Buenos Aires tango milonga – 2014
  • Hold a handstand for 30 seconds

Meet-in-Person Goals

  • Grace Llewellyn – 2006
  • Daniel Greenberg – 2004
  • John Taylor Gatto – 2010
  • Russell Roberts – 2014
  • Tina Seelig – 2010
  • Seth Godin – 2012
  • Daniel Pink – 2014
  • William Deresiewicz – 2014