Benefit From a Think Week, Just Like a CEO.
How to successfully contemplate the bigger picture with your own Think Week.
Bill Gates, Mark Zuckerberg, and Steve Jobs popularized the term “Think Week”, and now many entrepreneurs and creatives know about the benefits of such annual or bi-annual solo retreats. As a professional freelance journalist, a copywriter, and an unpaid short fiction writer who works from home, my time and attention are often divided between income-generation, keeping my abode in order, and creative writing. This overreaching makes for a fuzzy life depleted of inspiration.
But something changed after I embarked on my first Think Week. By physically extracting myself from life-as-I-knew it and from the distractions of my hyper-connected urban environment (I live in Hong Kong, a city that I’ve heard described by Manhattanites as “New York on steroids”), I began to see which goals and projects best aligned with my values, interests, wants and needs, and found the momentum needed to move forward with them.
What is a Think Week?
The idea behind the Think Week isn’t new, though it seems more relevant and necessary now than before as a prophylactic against information overload and burnout. Think Weeks are meant to help us lower the volume on our noisy, hyper-connected urban lives, to recenter, to recharge creatively, and to reinvigorate our thinking.
Long before Gates and other technopreneurs started opening up about their Think Weeks, another great thinker was already tapping into the transcendental power of going out alone into nature to get a better perspective on one’s life. In 1864, American essayist Henry David Thoreau published Walden: Or, Life in the Woods chronicling his time away from civilization, living deliberately, and fronting “only the essential facts of life” in a self-built cabin near Walden Pond in Concord, Massachusetts.
“I did not wish to live what was not life, living is so dear;” wrote Thoreau, “nor did I wish to practice resignation, unless it was quite necessary. I wanted to live deep and suck out all the marrow of life, to live so sturdily and Spartan-like as to put to rout all that was not life, to cut a broad swath and shave close, to drive life into a corner, and reduce it to its lowest terms.”
Escaping to the woods might sound idyllic, but a Think Week is not a solo vacation. The minimalistic existence that Thoreau describes is diametrically opposite to what most people do when on holiday — sunbathe at the beach, ski, visit museums and UNESCO heritage sites, watch an opera, drive to purchase oysters for a family brunch, shop and dine till they drop. Instead, Think Weeks are times set aside to contemplate the things that matter, and to let solutions to big problems arise. Because of this, they demand a level of austerity and require the right balance of structure and flexibility in order to be effective.
So why do it? Because all that solitude and hard work will pay off big time. That’s why Think Weeks are popular among CEOs and venture capitalists:
- Jessica Stillman profiled the rise of Think Weeks among top entrepreneurs in Why So Many Top Entrepreneurs and Investors Swear by Regular ‘Think Weeks’.
- Venture Capitalist Steve Schlafman detailed his own experience in a recent Medium article.
But it’s not just CEOs, VCs, artists, or entrepreneurs who can benefit from direction and clarity. Knowing where we want to go and how to get there can help us all live more effectively and allocate our time, attention and resources appropriately. Anyone who wants to live with more purpose can benefit from a Think Week. Here’s how to plan one, and my own example of the one that helped me prioritize my own creative work.
Designing Your Think Week
Planning is the key to a successful Think Week.
Permission to exit
If you’re an employee, you’ll need to apply for a week’s leave before making travel plans. If you’re a business owner, delegate your responsibilities to your number two, and inform your staff that you’re not to be disturbed for the duration of your retreat. If you’re self-employed, create an out-of-office email responder to let clients and associates know you’ll be off the grid and when you’ll be available again. If you’re married with children, you’ll need to let your spouse and kids know why you’ll be leaving them for a week or two, and where you’ll be going. When you speak with family, help them understand why they won’t be able to call you five times a day, and agree on set times (preferably at night) to speak. Be open about your goals and what you’ll be doing during your Think Week, so no one at home gets anxious.
Choose the right place
When choosing your accommodation, think about your budget and the type of setting that most inspires you. The good news is you don’t need to spend a lot of money to rent a cabin in the woods. A simple, clean space with a bed, kitchen, bathroom, a table, chair, and good lighting are all you’ll need. Of course, if you have a bigger budget, you can choose a place that is more luxurious — but keep in mind that cluttered interiors can result in cluttered thoughts.
For myself, small, one-bedroom cabins or cottages work best. Nature is not always a requisite, but it definitely adds more value to the experience. Being in nature is a wonderful psychological relaxant, and a relaxed body and mind are more conducive for creative problem-solving.
Think about the types of natural landscapes you like best. Some people love tranquil lakes or desolate beaches, others like dramatic cliffs and mountains, meadows might appeal to some, while others enjoy being nestled in a forest. Pick an environment that lifts your spirits, and find a property in such a setting that you’ll be comfortable living in for at least a week. If possible, choose a place without a television, or unplug it once you arrive.
Isolate and remove distractions
When choosing where to stay, removing distractions should be your top priority. I usually pick locations where I won’t be tempted to stop by the local shops, watch a movie, or check out cool local restaurants. Remember, this is not a holiday. You want to ensure you have as little contact with people and other distractions as possible.
I don’t drive, and my Cornwall cottage was an hour-long walk to the nearest town. This was ideal because there was no temptation to leave my work to entertain myself with shopping or sightseeing.
Deciding where and when to have meals can take up more headspace than you think. To free myself from fussing over where and what to eat, I purchased enough groceries for a week and planned my meals ahead of time, so I could focus on reading, writing, and thinking. A self-catering accommodation works well for Think Weeks. You can order your groceries online and have the supermarket deliver them a day before or when you arrive at your accommodation.
How long to stay
How much time can you take off from your regular life? One to two weeks is the ideal duration for Think Weeks. Any longer might diminish returns as you may feel you have all the time in the world and become a little too relaxed. When you know you have a limited time to work things out, your subconscious — aware that has a deadline to meet — exerts itself in an attempt to respond to your questions and solve your problems.
The longer version of the Think Week is the artist’s residency or writer’s retreat. These longer retreats, however, aren’t about finding direction and clarification (though they can include such time), but periods devoted to completing a single, large-scale project.
What to bring
Pack light and bring only comfortable and weather appropriate clothes. You will be spending a lot of time alone, so you won’t need to look chic. I do yoga in the mornings, so I bring a yoga mat too. You should always have a reading list and the books on it with you. I download the books I plan to read on my Kindle so I don’t need to carry excess weight in paperbacks. If you have music that helps you unwind or think, bring those with you too. You’ll also need your laptop, a notebook, and pens and pencils.
Consider how many emails will you need to reply to, and how many or phone calls you will need to take during your Think Week. The less time you spend online or on the phone, the better. If being completely offline is not possible because you have to reply to urgent emails, or your project requires research, then disconnect for at least the first half of the day.
I usually only allow myself to check emails or do online research in the late afternoon after I’ve completed some work and taken my daily walk. I usually only take one call in the evening with my husband.
Create a daily schedule
This is crucial. You will have time to rest and relax, but sleeping in until 10 a.m. or staying up late watching television is a no-no. You will be feeding your mind and stretching it beyond its comfort zone during your Think Week, so expect some mental exhaustion and resistance. Stick with a schedule to keep yourself disciplined.
Split your time between these four main activities:
- Brainstorming: This is when you identify ideas that you want or need to work on. If you lead a team, you can think about the key issues and challenges that you need to address. If you’re a designer or artist, you can use this time to create sketches or jot down themes and concepts that you’d like to find out more about. If you’re a writer, this is when you’ll select ideas that you’re most passionate about, think about titles, create character sketches, or plot outlines.
- Working: This is when you haul the results of your brainstorms and begin coming up with action steps, proposals, drawings, or written content.
- Walking: This is when you get to “go out and play.” This is your reward for staying put in your chair all morning. This is the time to leave your work alone, let your mind roam free, and feast on new sights, sounds, smells, and sensations. Forest trails or country paths are usually very peaceful. Strolling through them is a great way to unwind while getting exercise and increasing oxygen supply to your brain. Walking also gives your subconscious the chance to make new connections and provide you with unexpected solutions.
- Reading: It’s difficult to expect substantial output without substantial input. That’s why so many successful people and industry leaders make reading a daily habit. The trouble with regular life is that it usually offers only pockets of time for reading. Use your Think Week as an opportunity to read voraciously. Select books that are relevant to your field of work, or what you hope to achieve.
My Own First Think Week
In 2017, I took myself to a cottage set between forest and meadows near a small village in north Cornwall called Goonhavern. At the time, I hadn’t yet read about Think Weeks and didn’t know that this seven-day break would shape up to become one. What I knew was that I was overworked, attending more meetings, lunches, and coffee dates than I wanted to, irritated with my family for requiring more time than I was willing to give them, and angry with myself for repeatedly taking on low-value but well-paid work rather than doing what I really wanted — to complete and publish a collection of short fiction that I had spent the last four years working on in my spare time.
I was in a career and creative rut, and I needed to find a way out. At this time, my bread and butter came from writing eight to twelve feature stories a week for well-known interior design publications in Asia and America, and producing press releases for companies that manufactured cargo handling equipment and battery chargers. There are worse things one can be doing for a living, but there’s only so much time a writer can spend writing about chaise longues, vintage hydraulic tiles, Wegner Wishbone Chairs, Louis Poulsen Artichoke Lamps, forklifts and nickel-cadmium versus lithium-ion without turning into a zombie. I had a draft manuscript of 15 short stories that wanted my attention, and my Cornish retreat was the chance to spend some time with it.
During my seven days in the cottage, I woke up at 6 a.m., did 30 minutes of yoga in the garden, meditated for twenty minutes in the woods at the back of the property, then returned to the cottage to prepare and eat a leisurely breakfast. After breakfast, I sat by the kitchen window and reworked my manuscript until noon. Then I packed myself a sandwich and some fruit and head out for a walk through open fields, rolling hills, peat bogs, streams, and woodlands. I’d find a nice spot and stop to eat my sandwich. Depending on the weather, I’d walk for about 1.5 to 3 hours.
I took my time on these walks, stopping to watch foxes and hares that crossed my path, listening to birdsong, or contemplating a magical-looking tree or a rock with a mossy face. Ideas and dialogue sometimes came to me and I’d jot them down in a notepad I carried in my backpack, but mostly I just took in the beauty of my surroundings. After returning from my walk, I sat at my work station/kitchen dining table and brainstormed ways that I could publish and sell my book, and also how I could change my daily routines and adjust my monthly expenditures so I could take on less paid work and spend more time writing fiction. At sunset, I put away my laptop, had a bath, cooked and ate some dinner, got a fire going, then hunkered down on the couch to read. At around 11 p.m., I went to bed. I woke up at 6 a.m. and repeated the same activities the next day.
During my time at the cottage, I realized that I needed to accept the reality that short story collections are incredibly challenging to sell, especially for unknown authors. My query letters had been rejected by half a dozen agents. But as disheartening as this was, I didn’t give up. I had worked hard on my manuscript. I had it critiqued, rewritten, edited, and rewritten again. I had let it rest and revised it, tweaking each sentence to make it the best it can be. I had worked through the big-picture issues, as well as the details. I knew this was the best I could do for now. I sensed that if I didn’t do something with my manuscript soon, I’d lose my drive to write fiction, and would take the easier route, forget about short stories and just follow the cash. I concluded that making money from the book was not a priority for me at this time and that it was more important that I release the book into the world so that I could move on and write another.
I discovered all this and got realistic about my expectations during my Think Week in Cornwall. And I also used this time to come up with an action plan to self-publish and market my book.
When I returned home to Hong Kong, the manuscript for my short story collection Without: Story of Lack and Longing was ready. I sent it to an editor, self-published it with Amazon Createspace, and distributed it to more than a dozen bookshops in Hong Kong and Singapore. I organized four book launch events: one for my own circle of friends and acquaintances, another two at bookshops in Hong Kong, and one at the Singapore Writers Festival. Within three months, I had sold more than 200 copies, which was more than I had hoped for. I hadn’t felt so fulfilled in ages. I knew I was moving in the right direction.
A week after my Cornwall trip, Californian holiday home rental brand Boutique Homes commissioned me to write an introduction to a chapter about rural escapes for their eponymous coffee table book. The chapter was titled “Unplugged in Nature”, and it had me thinking about why the change of scene and slower pace of life in the Cornish countryside had been so beneficial. This was my analysis, which I included in the chapter introduction:
“I think time in the countryside [you can substitute this with forest, remote beach, mountain or dessert] is particularly important for artists, or anyone who wishes to bring passion into whatever they do. Country living [substitute with any other environment close to nature] with its quietude, privacy, and wide-open green spaces affords the artist — and shouldn’t we all be allowed to be artists? — time to idle and daydream, processes which hectic city life have made almost impossible. This ‘down time,’ I believe, is essential for gaining insight into how to best approach one’s work, as it is often during such restful sojourns that the muses awaken.”
I now plan a Think Week every year and continue to enjoy their rewards.
If you’re trying a Think Week for the first time, you will face challenges. Think Weeks require that you get comfortable with your own company and strike the right balance between doing and being. If you’re not accustomed to spending long periods of time on your own without distractions and switching between deep work and complete relaxation, here are some tips to help you through the rough spots.
You might feel lonesome at times. For me, this sometimes happens around sunset. Unconnected and unmoored, you might miss your loved ones, perhaps you’ll get swept up in waves of regret about the past, or you may feel despondent and wonder “what’s the point of it all.” Everyone feels bluesy now and then, but being isolated can make such feelings more acute.
Rather than allow melancholia to overwhelm you, tap into these uncomfortable feelings, and ask yourself where they come from, and what you can do with them? Why does my family matter so much to me? What is the point of writing fiction? How can I translate nostalgia into heartfelt storytelling? How can I avoid making the same mistakes I made in the past? Why do we all have to die?
By embracing your not-so-pleasant emotions, you can engage your inner philosopher and address the big questions to ensure you make the right maps. This is a week for thinking, after all, so channel your inner Plato or Socrates to help you fearlessly look within. By syncing your thoughts with your emotions, you’ll discover new ways to improve your life and rise above the limitations of your instincts and social conditioning.
There were mornings when I sat in front of my laptop, feeling an overpowering urge to play Candy Crush or watch old “Saturday Night Live” YouTube clips. When this happens, I know that my mind doesn’t want to work with me. The solution is doing something physical. I usually stand up and do some stretches, or ten sun salutations, or I might take a brisk walk around the cottage. When I return to my workspace, some of the mental restlessness would have been released and I can then get back to the task at hand.
Learning to relax
“Quiet the mind, and the soul will speak,” said interfaith spiritual guru Ma Jaya Sati Bhagavati. If you’re accustomed to running at a million miles a minute, and your day is one big to-do list, cultivating a state of inner quiet can feel incredibly unnatural. A tired, overworked mind isn’t as useful as a well-rested one, so it’s important to regularly unclench your mind and allow it to wander free at least once each day. Those long afternoon walks are the perfect countermeasure against mental fatigue. You can also relax by meditating, having a warm, soapy bath with music, or just lazing on the couch and gazing out the window.
What You’ll Take Home From a Think Week
When you return from your Think Week, hopefully you will have worked through your doubts about your professional abilities and the work you do. You will have identified flaws in your thinking, methods and practices, or in your organization and processes, and discovered ways to reduce or remove them. You will now know where to focus your energies.
You will have a roadmap that enables you to confidently carry out your vision for a better life or a better world. And you will be on track to achieving your personal and professional goals.