Guide: How to Structure a Deep Learning Retreat

The 5 steps to structure a deep learning retreat

Guide: How to Structure a Deep Learning Retreat
Photo by Cara Fuller / Unsplash

I have been experimenting with a new habit in 2021: deep-learning retreats. I've never done a "think week" (popularized by Bill Gates) until this year, but I tried one out in the spring when I escaped to the mystical and barren New Mexico desert and holed up in an Airbnb to read, study finance, write in my journal, and explore future trends. It ended up being one of the best things I have ever done, so I made plans to do it again in 2021.

In August, I took two weeks off to attend a full-time, enthusiast cooking course taught at a professional culinary school in Vancouver (I've always wanted to learn the first principles of cooking). With early mornings and evenings free, I set an additional learning agenda for myself on topics of decentralized finance and climate change policy.

In total I’ve taken three weeks off this year to focus on deep learning, and I'm more convinced than ever in the power of deep learning retreats. This post offers a framework for how to design your own deep learning retreat. I'll continue to refine this framework as I embark on additional deep learning weeks and refine the model.

I’ve found there are five steps to designing deep learning retreats, and, in my experience, their order is important:

  1. Carve out the time first
  2. Identify your learning goals
  3. Leverage your unique learning style
  4. Create the conditions for focus
  5. Embracing learning as struggle

1. Carve out the time

The first step is to carve out the time by creating the protected container for yourself. Learning is scalable across different amounts of time, so don't be ashamed of how short your learning retreat is. You can learn a profound amount in an hour (see this article) or just one day. Multi-day retreats are valuable because you can more completely shift into a different mental space that is distinct from your daily routines. No matter if it's one hour, one day, one week, or longer, carve out the time first and block it on your calendar. If you can, consider doing it now before reading on.

2. Identify your learning goals

You likely fall into one of two categories:

  1. You don't know what you want to learn, but you have a vague sense that a deep learning retreat would be productive and enjoyable for you.
  2. You know exactly what you want to learn (which could be one specific thing like going to cooking school or a specific set of topics).

I embarked on my first learning retreat unsure of what I wanted to learn because there were multiple topics capturing my attention. Should I take an online course on investment analysis, spend more time with my Spanish language tutor, read about the invisible caste system in America, do some reflecting and writing about the learnings and mistakes of my leadership journey, or something else? It was such an unbounded set of options that it took some effort to narrow down, which is why identifying your learning goals can be the hardest step if you want to explore and learn many things. (If you know exactly what you want to learn, you can skip down to Step 5 below).

Here is a 5-step framework I created to determine where to focus your time during a deep learning retreat:

Step 1: Framing Questions

  • Do I want to focus on one topic or multiple topics?
  • Do I want my learning to be outcome-based (where you produce something) or do I want it to be more of a journey without an outcome at the end?
  • What meaningful benefit will I gain from this act of learning?

Step 2: Go wide and Brainstorm

Brainstorm everything you want to learn. Set a timer for 15 minutes and start listing out topics you’re curious about. Use up the whole time and focus on the quantity of topics or ideas. You can pare down later, so don’t let your mind evaluate the quality of your ideas. Add as many as you can.

Step 3: Create a criteria to narrow your list

Your criteria is personal to you. Here are some examples I’ve used before:

  • Barrier to learning: Topics that require more space and time to dive into (which lend themselves well to multiple protected hours or days of study). For example, I signed up for an online course on learning the principles of artificial intelligence. It’s taught asynchronously, so I can watch lectures on my own time, but it’s hard to make progress through the course without dedicating multiple hours to it.
  • Curiosity: Topics I am most curious about
  • Professional development: Topics I believe are strategic for me in my professional career
  • Deliverables: Topics or ideas I want to turn into deliverables (for me, this is often in the form of writing). Perhaps you want to learn how to sketch portraits and you are going to dedicate time during a deep learning retreat to grow in your sketching ability. A deliverable here might be four produced sketches.
  • Goals: Topics or areas of study that will help you achieve specific goals. For example if I want to be conversational in Spanish by the time I travel to Mexico City in three months, then I might dedicate time to brushing up on my Spanish.

Step 4: Narrow down your list

It’s easy to over-schedule yourself for deep learning retreats, so be judicious and selective in how you apply your criteria. There aren't helpful heuristics on the number of things you should learn simply because some things take much longer than others and the length of a learning retreat varies as well, but resist overcrowding your deep learning retreat schedule (this is something I struggled with).

This will take practice: narrow your list, complete your deep learning retreat, and then recalibrate the number of topics for the next retreat. Remember, one of the most under-acknowledged choices we have in life is where we place our attention.  

Step 5: Define success

I love unbounded, undefined learning retreats where I meander and explore a topic without a specific outcome or goal, but I still try to define what success looks like. In this case, it could be the number of hours I would dedicate to a specific topic. You will feel far more accomplished at the end of your deep learning retreat if you believe you’ve achieved your goals for the retreat. One of the beauties of learning is that it doesn’t necessarily have to result in a deliverable or a work-product (which is why I use metrics like hours spent instead of words written or articles read). But regardless of if you want to spend six unstructured hours exploring a topic or if you want to score an 85% on a Spanish Test or master the art of roasting vegetables, define your success. Here are a few success metrics you might consider:

  • Number of hours spent on a topic
  • Original point-of-view on a topic (e.g. “I have a working theory and point-of-view on the steps my organization can take to become anti-racist in its hiring processes.”)
  • Work-product produced (e.g. piece of music, culinary dish, piece of writing, etc.)
  • Mastery of a topic (e.g. “I can clearly explain the relationship between a balance sheet, income statement, and cash-flow statement”).
  • Number of articles or books read
  • How you want to feel: This is not a quantitative metric, but it is a powerful one. How do you want to feel at the end of your learning retreat? Do you want to feel unhurried and rested? Do you want to feel educated and convinced?

3. Leverage your unique learning style

Everyone learns differently. I find that I learn through synthesis where I absorb something, take notes, summarize it in my own language, integrate into my existing mental models, and then build upon this new knowledge with additional questions, ideas, and patterns until I form a point-of-view and am capable of articulating it cogently to others.

For you to be most fulfilled, you’ll want to leverage your unique learning style. If the content is what you’re learning, then your learning style is how you best engage with that content.

I’ve never had much success in categorizing myself in the typology of being a visual learner or verbal learner or something else. Instead, I’ve found the following bright-spot questions help me to uncover what learning style best suits me:

  • Is there an example of a time when you effectively learned something? How did you learn it? (Don't mistake learning speed for effectiveness).
  • What topics do you have mastery of? How did you learn those topics?
  • What topics have deeply stuck in your memory? How did you learn them?
  • What approaches to learning did you find least effective? Where did you most struggle in learning? (Pay attention to times when you were not successful at learning something, not just what felt like the biggest struggle.)

The goal is to craft a learning environment and learning style that best suits you. Use the answers from these questions to identify the ways you best engage with content (you might decide to watch Youtube videos instead of reading books, or you might decide to punctuate your learning with journaling time). Then prioritize those learning styles. For example, there is research proving that handwriting notes is one of the best ways to remember something (as opposed to taking notes on a computer).  

Collaboration vs. Solitude

I’ve found that I do my best learning in dialectical conversations with people who challenge and refine my ideas. I have a few of these “intellectual sparring partners” and we have monthly meetings on the calendar for us to spar with each other around contemporary topics. When I was attending cooking school, I found it helpful to cook alongside other amateur chefs and learn from their techniques, get corrected when I made mistakes, and fill in gaps in my mental models of culinary learning. That said, I am an introvert, and I need time alone to further attach new learning to my existing mental models. For everyone one hour I spend learning with someone, I need another hour on my own.


I’ve found that a full seven days of deep learning gets heavy and monotonous if I’m learning everything through the same learning style (like reading books). I just can’t power through 8 hours of reading x 7 days. Varying the learning style has worked well for me on my retreats. During my first learning retreat, I would read in the morning, go for a walk at lunchtime in the New Mexico desert and listen to a podcast, then return to write in the afternoon, followed by a nap. When I was in Vancouver learning how to cook, I would wake up early and wander to a nearby coffee shop to read cook books, then spend 9am to 3pm each day in the kitchen cooking through trial and error, and then in the evenings, I’d come home and direct my attention towards learning more about climate change.

How structured or unstructured do you want to be? Only you can answer this question, and the best answer is a function of the learning style that works well for you. I’ve found loose structure works well for me. The beauty of a learning retreat is that you aren’t accountable to anyone else than yourself; let your curiosity propel you forward and be willing to change your plans if you feel like your learning has become obligatory. If it has become frustrating, perhaps press on (more on this below).

4. Create the conditions for learning

Designing optimal learning conditions is overlooked as a key driver of effective learning. Given your time, your topic(s), your goals, and your learning style, what are the conditions you need to be most successful?

Location and Environment

If possible, conduct your deep learning retreat in a location set apart from your daily routines and daily locations. This will create a psychological separation from the modes of thinking you employ normally and invite you to consider this time and space as sacred and distinct. This article and podcast outlines the benefits of how changing your environment can lead to boosts in creativity. If you're taking a multi-day retreat, leave your normal surroundings and spend time set-apart in a location that has few associations or distractions. If you're taking an hour out of your day to learn, leave your office or home and go to the park, a coffee shop, or the quiet halls of a public library.


It’s hard to overstate the relationship between sleep and learning. The data are clear: sleep improves our ability to learn. In Why We Sleep, Matthew Walker enumerates the research on how sleep enhances our ability to learn:

  • Sleep before learning refreshes our ability to make new memories
  • Good sleep the night after learning helps us retain information we learned
  • Sleep clears our short-term memory capacity to absorb more learning
  • Sleep perfects. Practice doesn’t make perfect, but practice, followed by sleep, makes perfect.

If you can, prioritize at least 8-hours of sleep per night. I have written a summary of the key takeaways in Why We Sleep, which you can read here.

Movement + Dopamine

I like to run, and I’ve observed that running is a form of mental hygiene for me: my mind wanders, it processes information from the day, and it helps me to arrive at insights and draw conclusions that might be more elusive when just sitting at my desk.

You’ve probably heard this before, but we often have our best ideas in the shower. The neurological reasons for this are similar to those for the mental hygiene of running and provide a framework for creating the conditions to be most creative. Creativity is enhanced when we are:

  1. In a relaxed state
  2. Willing to be distracted (distraction is the opposite of focus. Focusing on a specific task can be an impediment to making non-obvious connections and drawing insights)
  3. In a place (or headspace) that releases dopamine (like exercise or the shower)

Use of Technology

Technology has been an important tool during my deep learning weeks, so I am not one to advocate for completely disconnecting from the internet. I have taken vacation days to protect these deep learning retreats, set auto-responders on my email, and removed myself from any work-related activities, so that separation from work has been important for me to guard my attention.

Here is how I’d approach thinking about your relationship to technology (or any other addicting distraction) during your deep learning retreats:

  • On a normal day when I’m not on a retreat, what are the distraction traps I most often get caught in? How might I remove these during this time?
  • What connectivity or use of technology is essential for me to maintain during this time away? It's been helpful to remind myself that I shouldn’t give my personal sense of importance too much credit and that, as much as my ego likes to think otherwise, I can disappear for a few days and everything will be fine.
  • What connectivity or use of technology will enhance my goals for this retreat? How can I keep my use of technology within these bounds?

5. Final Thought: The Power in the Struggle

In his book Range, David Epstein talks about the relationship between learning speed and learning retention. His draws from multiple research studies to point out that the most durable learning (as measured by learning that is retained) is learning that happens slowly and happens through a person struggling, failing, and experiencing set-backs.

In other words, show me something that was "learned" effortlessly and I will show you something you are likely to forget. The things that stick with us are the things that didn’t come easily. Epstein distinguishes between actual learning versus the feeling of learning. The feeling of learning is based on progress you can observe, whereas actual learning is something more imperceptible and deeper. (You can check out a brief book summary of Range I wrote here).

I’m convinced that adult learners don’t spend enough time in intentional learning spaces. This is both a prioritization problem and a time problem. But I’m also convinced that our relationship to learning is also optimized for ease and enjoyment.

We love listening to that viral TED talk, to reading that The New Yorker article, to digesting the news snippets in the email every morning that compiles yesterday’s top stories. But all of this is effortless, passive learning. This is learning without struggle. This is learning without frustration and vulnerability.

Deep learning retreats create the opportunity not only to prioritize learning, but to change our relationship to give us permission to learn in ways that our society and our schedules don’t usually permit.

Perhaps, then, the most important piece of advice about a deep learning retreat is this: give yourself permission for your learning to be messy and (seemingly) unproductive. Carve out the space to wrestle and let go of the need for constant optimization and progress, and you’ll be able to carry this learning posture beyond the confines of a retreat and into the rest of your life.