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 if 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: March 2024]
[Also see: No More Goals]
Traditional Goals
- Start a family
- Get a dog
- Graduate from college – B.A., UC Berkeley 2004
Writing & Speaking Goals
- Publish a book about going to college without high school – College 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
- Publish a more personal, vulnerable book – Do What You Love and Die Trying, 2023
- Give a TED talk – TEDx YouthDay Palo Alto, 2010
- Do a speaking tour in the U.S. – 2018
- Speak in Europe – 2017, 2018, 2019, 2021…
- Publish 10+ original audio or video episodes online – Off-Trail Learning podcast, 2015
- Independently publish a professional-quality book – Better Than College, 2012
- Give away 10,000 digital copies of Better Than College – 2014
- Blog every day for a year – failed in 2011 and 2013
- Write the first draft of a 50,000-word novel in one month (the NaNoWriMo challenge) – failed in 2006 & 2009
Work Goals
- Work at Not Back to School Camp – 2006
- Work as a summer camp cook – 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
- Start an international trip leading company – Unschool Adventures, 2008
- Create a leadership program for homeschoolers – Homeschool Leadership Retreats, 2010 (merged with U.A.)
- Direct a summer camp – Deer Crossing Camp Deputy Director, 2008
- Earn passive income – Launchpad (2017) + book sales via Amazon (2012)
- Run a “how to do college without college” program – ZTC Camp 2011
- Teach an online course – Self-Directed Learning 101 (2020)
- Organize a conference – Trailblazer Gathering, 2013
- Run an Unschool Adventure trip without me on it – Writing Retreat + New Zealand 2019
- Create a brick-and-mortar “school” (i.e. long-term structured learning program)
Travel Goals
- 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
- Dance with a stranger in a Buenos Aires tango milonga – 2014
- 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
- See the Aurora Borealis with Matt & Patrick
Outdoor Goals
- Roll a kayak – 2003
- Do a long bike tour – 2020, 2021, 2022
- Day-hike Mount Whitney – 2017 – failed in 1998, 2006, 2016
- Hike the Te Araroa (NZ) – kinda, 2019
- Thru-hike the Sierra High Route – mostly, 2018
- Hike the Southern Sierra High Route – much, 2019
- Hike the Camino de Santiago – 2017 (Norte/Primitivo)
- Run 13.1 miles on trail – 2010 (Asheville, NC)
- Run 26.2 miles on trail – 2014
- Run 30+ miles on trail – 2015 (John Muir Trail), 2016 (Tahoe Rim Trail)
- Windsurf in the Columbia River Gorge – 2014
- Backpack the Lost Coast (CA) – 2015
- Cycle the Carretera Austral – 2024
- Fast-pack the Tahoe Rim Trail – 2021
- Hike the Bay Area Ridge Trail – 2023
- Do a long solo ramble (a la John Muir) in the High Sierra
- Slow bike trip around the Bay Area with 100% Warmshowers hosts
- Thru-hike the Pacific Crest Trail – failed in 2005
Experience Goals
- Do a 10-day silent meditation retreat – did half in 2019
- Walk a 100′ slackline and a high-line
- 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