How to plan a Learning Sabbatical

How to plan a learning sabbatical

If the format of school is lectures and tests, what's the structure of a learning sabbatical? How will you choose what to focus on? Where will you find community for motivation and feedback? How will you apply what you've learned?


Even though formal education has its challenges, self-led learning isn't necessarily better. Most self-led learners, myself included, don't spend enough time thinking through meta-learning (learning how to learn) prior to starting.

Allocating time to meta-learning throughout a sabbatical is time well spent because it adds leverage to future learning efforts. Below are a few resources that helped me (re) learn how to learn.

Ultralearning by Scott Young - This book details strategies for self-directed learning. It's a must read for anyone embarking on a learning sabbatical. Here's a high level summary of his framework:

  • Metalearning: First draw a map. Start by learning how to learn the subject or skill you want to tackle. Discover how to do good research and how to draw on your past competencies to learn new skills more easily.
  • Focus: Cultivate the ability to concentrate. Carve out chunks of time when you can focus on learning, and make it easy to just do it.
  • Directness: Learn by doing the thing you want to become good at. Don’t trade it off for other tasks, just because those are more convenient or comfortable.
  • Drill: Attack your weakest point. Break down complex skills into small parts; then master those parts and build them back together again.
  • Test to Learn: Testing isn’t simply a way of assessing knowledge but a way of creating it. Test yourself before you feel confident, and push yourself to actively recall information rather than passively review it.
  • Feedback:  Feedback is harsh and uncomfortable. Know how to use it without letting your ego get in the way.
  • Retention: Don’t fill a leaky bucket. Understand what you forget and why.
  • Intuition: Develop your intuition through play and exploration of concepts and skills.
  • Experimentation: Explore outside your comfort zone.

This advice may sound generic. Don't let that dissuade you. If you're planning a stint of self-led learning I promise you'll get a lot out of this book!

How We Learn by Stanislas Dehaene - This book, from cognitive neuroscientist Stanislas Dehaene, provides a high-level overview of the science of learning. Engaging and evidence-backed, it helped me better understand the immense potential of young minds as well as the constraints of brains as they age.

In Search of Deeper Learning by Jal Mehta - Although this book is about the learning models of American high schools, I found it extremely applicable to thinking about the challenges of self-led learning. It details the tension between project-based and scaffolded learning. It also highlights the importance of community, identity, and apprenticeship.

Learn how to Learn by Barbara Oakley on Coursera - This course has over 66k ratings and 2.5M students enrolled. I didn't learn much new but it's a good primer that is engaging and well produced throughout.

Other important meta-learning concepts.


  • Write down your motivations. Prior to starting a learning sabbatical, it's important to reflect on your motives and validate that self-led learning is a viable route to success. Decide whether you're spending time on topics for intrinsic (the joy of learning) or extrinsic (get a job) motivations. If extrinsic, find a few people who have made a similar transition previously and interview them about it.
  • Search for predicates. When you begin to research a new subject, search for someone who has gone on a similar learning journey before you. Gather and compare curriculums. Search for roadmaps/guides.
  • Create a curriculum. Build your own curriculum and iterate as you go. As you progress, consider creating a concept map (on something like Coggle) to help organize what you encounter. Here's the curriculum I put together as an example.
  • Only read 3-star reviews. When looking for books or courses, 3-star reviews tend to be less biased and include valuable snippets like "This book is great at X but this other book was better at Y." Both 5-star and 1-star reviewers tend to be less objective.
  • Never stop revising. I spent about a year and a half compiling learning resources prior to quitting my job. During the sabbatical, I allocated a few days each month to reflect and iterate the learning plan.
  • Don't neglect a financial plan. While learning sabbaticals are much cheaper than grad school, it's not exactly easy to finance them. I spent 6 years saving and worked part-time (1-2 days a week) during much of my sabbatical so I didn't have to worry about cost of living.


Without the infrastructure of a formal educational environment, it can be easy to get sidetracked and demotivated. Here are a few tips on how to structure your self-directed learning experience:

  • Constrain by deliverables. Schedule external deliverables throughout the sabbatical that force you to complete work and get feedback on it publicly. This could include blog posts, videos, or working products.
  • Constrain by time. Time-box explorations of topics. I broke my sabbatical into semesters and focused on one subject at a time. This worked better for me than trying to juggle many topics simultaneously.
  • Teach to learn. The best way to ensure you really understand a topic is to teach it to someone else. Said another way, learn in public.
  • Pay for tutors. As mentioned above, 1on1 tutoring is a very effective pedagogical technique. Reallocate money you might have spent on tuition towards personalized feedback. Tutors also help with accountability. Find tutors via Wyzant, Codementor, or UpWork
  • Treat memory as a conscious act. When reading books, take notes or use Kindle's highlight functionality to capture important passages. Highlights get automatically uploaded here. Review the highlights when you're finished with the book. Then, synthesize the important concepts in your own words and create flashcards in a spaced repetition system like Anki.
  • Give yourself permission to drop bad educational material. If the book, course, or project you selected isn't engaging you, find a better one. A better alternative almost certainly exists.
  • Track your routines / habits. I built this spreadsheet for tracking mine and reviewed it weekly with a friend.
  • Read Atomic Habits by James Clear. This was a great resource for thinking about behavior change.
  • Document your journey. Depending on your field, self-led learning's lack of credentials can either be a benefit or a curse. For someone in software, a learning sabbatical can give you the time to build a portfolio of work, proving your competency. For most other fields, employers equate "self-taught" with "weird" at best. Because of this, it's important to document your journey and produce work that's easily digestible. This enables others to give you feedback. It also serves as a stand-in credential for future employers. DataScienceJourney is one of the better examples of this that I've seen.


Willpower is grossly overrated. Productivity comes from systems of accountability and social pressure, not self-restraint. Here are a few ways to stay motivated during your learning journey:

  • Find an accountability buddy. Schedule a weekly call to 1) Review the prior week's goals 2) Review your daily habits and 3) Set new goals for the coming week. Consider choosing one task to wager $$ on if you fail to complete it. Accountability buddies work best If they're also doing a learning sabbatical or freelancing or something else similarly self-directed.
  • Cowork with friends. I was vastly more productive coworking with friends than working alone. Try Caveday if you're looking for virtual accountability.
  • Find a community of practice. To learn a new skill, join a culture where your desired behavior is the normal behavior. Deliberate practice is achievable when you see others doing it every day. If your learning sabbatical plans include software skills, I highly recommend the Recurse Center, a phenomenal organization that facilitates (free) self-led coding retreats.
  • Find sabbatical peers. At the beginning of my sabbatical I was lucky enough to get connected with four other people also embarking on self-led learning. For the next year, we scheduled a monthly call to share updates and lend one other emotional support. This peer group was invaluable to me.