Dreamscaping, Visioneering, and LifeCrafting — A New Years’ Goal-Setting Practice

Every year between Christmas and New Year’s, I take a week in solitude, isolating myself, ignoring email, avoiding the phone and all other distractions — and I dream. Most years I go away to LA, but just as often I stay here in Toronto and go through a specific practice I’ve put together over the last decade or so. It’s incredibly enriching and something I recommend everyone give themselves some time to do, but it’s not something I’ve ever shared in writing before.

You don’t have to do it around new years — I’m starting late, myself — but I find it a good time to catch up, reflect, and reset. It’s particularly useful if you’re in transition or looking to reinvent yourself because it’s designed to help you step back and figure out what really calls you.

If I ask “what’s the most important, impactful, significant thing you want to do — in the next hour?”… well, that’s too small a window in which to really do anything meaningful. If on the other hand, I ask you “what’s the most impactful thing you want to do with the rest of your life?” — but I give you thirty seconds to answer, that’s also too small a window. To really get a sense of what’s important to you, you need both a big window in which to contemplate and a big window about which to contemplate.

Not everyone can get a week, particularly around new years. I was coaching an impact investor years ago who was considering starting his own firm. He had two new babies, so getting a week to himself was impossible, but he was able to negotiate a day in a hotel. He ended up starting the firm.

I recently co-presented some of these ideas with a wonderful facilitator, Trae Aishley-Garen for the Unity Team, an impact-focused subgroup of tech billionaire Salim Ismael’s Exponential Organizations Open ExO community. One of the leaders in the group commented that he, having kids too would be lucky to get a few hours to himself. Perfect. Carve out whatever amount of time you can.

I break the process down into three rough phases:

Visioneering, and

The first phase of the practice involves dreaming big. Using sharpees and a ton of blank paper, I’ll create a page for every area of life — relationship, work, finances, health, purpose, and more. As an idea comes to me for something I’d like to do, be, or have, I jot it down. I’ll litter every surface, from couches to tables to counters with a page. Your mind is like a tree of ideas. When you keep them bunched up in your head or a 1–2 square foot screen or notepad, you in a way compress them. When you give yourself a large canvas, lots of space, you allow your mind to stretch out. I’m fortunate to have three giant whiteboards and I still use my computer throughout the process, but I give myself that unlimited canvas.

I’ll try to create a relaxed setting where I don’t have to worry about anything external. I’ll prep and order in food, I’ll give myself all of the coffee and other treats I want so I can clear my head and start asking a few eye-opening questions. The first few are more about “purpose attunement” — tuning into your purpose — while later ones are more grounded in the present and immediate future. Use the ones that are appropriate for where you’re at.

  1. There’s an expression “most people overestimate what they can do in a year and underestimate what they can do in ten. The current average lifespan is between 72 and 75 years — before all of the advances in medicine and human longevity. So, depending on your age, you may have between 20 and 50 years left — let’s say an average of 30. What could you do in that time? What could you not do? The world has been changed in less time. Countries have been formed and destroyed, billions have been raised and lost, movements have risen from nothing and created revolutions. When you give yourself that kind of time scale, that size of canvas, you really take the limits off.
  2. If you had all the time, all the money, and all the support in the world, what would you do? Again, this takes any limitations off, which allows you to really dream big.
  3. It’s not just for the long term. The above questions are good for figuring out the big picture and your purpose if you don’t already feel you know it. It’s also about today, this year, and the next. Create a page for relationships, health and fitness, finances and life position, activities you want to do or stop, habits you want to build, books you want to read, skills you want to learn, and even things you want to acquire, and the ask one of (I believe ) Tim Ferriss’ questions for this kind of reflection “what do I want to be, have, and do?” in each of these areas. If you want some ideas on areas of life to create pages for, check out my LifeMap introduction, here. Treat it like brainstorming — there are no bad ideas. Don’t filter yet. This allows you to really imagine.
  4. In systems thinking, there is the concept of idealized design — creating the optimal design, independent of what currently is there. Entrepreneur and community builder Jayson Gaignard asks “it’s one year from now, we are cracking open a bottle of champagne in celebration — what are we celebrating?” For each page you create, think about where you want it to be in a year. One of the most rewarding parts of doing this process annually is looking back at the last year. Seeing something that seemed impossible to accomplish in a year — that happened in March — reminds you to dream big, even in the short term.
  5. This isn’t just about dreaming, there may be very practical things I have to do — file taxes, fix something in the home, get back to someone, etc. I’ll give space for that type of thing as well. Otherwise, they will occupy your mind and limit your ability to really explore.

Because I’m using sharpees and can see the ideas from across the room, the ideas cross-pollenate. Suddenly a project idea and a travel goal start dancing with a relationship goal. Having the ideas visible, while giving yourself time and space to relax and reflect offers a new perspective. Something happens when a big dream sits there staring at you for hours or days. The imagination starts asking how to make that happen. Which leads us to the next phase.

Though it often overlaps and even happens throughout the dreamscaping process, visioneering is more about synthesizing everything that comes to you into one vision of your where you want get and how you get there. So visioneering — engineering our vision — is the process of both honing a cohesive vision for our lives and strategizing and planning for how to actualize it.

You may feel you want to leave your job and start a new endeavour, but feel not in position to do so. This is where you identify and hone the vision of that new endeavour and then brainstorm how to make it happen. If you run into problems, use Mental Jiu-Jitsu — turn the problem into a question. If the challenge is “I don’t have the resources to start,” ask “how could I get those resources?” or “how could I make it happen without those resources?” The brain will come up with answers — Mental Jiu-Jitsu allows us to use problems to identify where we can make progress.

Sometimes the challenge is that we have too many options. One way I think of how to choose is best explained through a metaphor, the idea of virtue (Te) in the Tao Te Ching — not virtue as in the Judeo-Christian sense of moral piety, but virtue as a superpower. How does this work? Imagine you’re trying to go from point A to point B — what’s the shortest distance? A straight line. Does that change if you’re in a pool? Not really. But if you think you’re in a pool, but you’re really in a slow-moving river, you would have to swim hard upstream in order to get there. If instead, you realize you’re in a river, realize which way it’s flowing and were you want to get, you can simply make the slightest change in direction and the river will take you there effortlessly. A nice-sounding idea, but nonetheless a little “woo woo”. How do we apply this? What’s the river? Passion.

If you love painting and hate accounting, which would be more draining — nine hours of painting or one hour of accounting? One energizes you, one drains you. Seek those things — activities, people, goals — that charge you up. If you’re considering an occupation shift, dream of work that you would enjoy so much it wouldn’t feel like work.

Visioneering is were I begin to collect all of the pages and try to amalgamate them onto one or a few, whatever makes sense. Perhaps you’ve dentified a dozen things that have to happen for your business, home, or relationships. Which is number one? What’s last and what’s everything in between? If dreamscaping is allowing the mind to wander and wonder, visioneering is reigning it in. Some ideas won’t resonate as strongly as others. Cut them, defer them, or schedule to revisit them later.

Dreamcasting is imagining the dream life you want and visioneering is setting the destination and the plan for getting there, but those are different from our day-to-day reality — our lifestyle. Ferriss uses the term lifestyle design and Gaignard asks “what does your perfect day look like?”. Now that we have aspirational ideas for life generally and areas within it, as well as a plan for moving towards them, we want to design our reality — both our days and our year.

Big things take time. The Art of War, teaches that you overcome big challenges by breaking them down into little challenges. I’ll start with the year by taking blank paper and drawing two lines across and three lines down it, creating twelve squares. This allows me to quickly and more freely than a computer calendar see the year. Even more powerful is to take a monthly calendar — one of those large calendars with 31 squares on it and treat each as a month instead of a day. If you’re dreaming big, you may have a very long plan in mind. Give yourself the space to chart it.

Your fitness goals translate into a daily and weekly routine — what does that look like? When, generally, are you getting up, what are you doing — and not doing — first thing? Are you more productive cognitively in the morning or at night? Do you find it easier to get your fitness in first thing in the day or later on? Do you connect with friends, family, and community every day or make a point of it once/week? How are you ending the day?

Beyond the logistical, how do you talk to yourself? Do you have a mantra or optimal state of mind you want to start the day with? Are you hard on yourself, kind to yourself, or a balance of both? How do you treat others? How do you make decisions? Who are your influences, supporters, and supportees? Not that you’ve dreamed big and honed a vision, map out the life you want.

Additional Thoughts

Starting The Year Clear
If, say, I have a week, I'll take the first day to just catch up on emails, admin tasks, accounting, etc. Throughout the year, so many open loops get formed - they each take a small amount of mental space. Clearing them out of the way not only allows you to better relax into thinking freely and big, it helps you start the year feeling free and light.

Pamper Yourself
In addition to removing the typical distractions and stresses, we actually want to inject a little comfort and pleasure. Pampering oneself, whatever that means for each of us, allows us to get out of the fight or flight nervous system and into the rest and digest nervous system. Often this means something we really enjoyed as a kid — for me, it’s comic books and video games. What is it for you? I try to carve out enough time and space to feel like I'm on a vacation.

Cannabis and/or Dopamine Support
While some find it a contentious suggestion, peak performance and flow-state author and journalist Steven Kotler describes a real “hippie speedball” - 25 minutes of exercise, cannabis, and coffee (a hippie speedball is typically described without exercise) - as an incredible way to get into a flow state. Some work well with it, some do not and as Alex Berenson recently pointed out on Joe Rogan's podcast, it actually comes with severe mental health risk for a small percentage of the population (I mention just to be responsible when suggesting it). Both coffee and cannabis release dopamine, the pain-killing, feel-good hormone. Creating a relaxed environment without distractions and time to yourself, supported by whatever feel-good activities and items you enjoy really helps get into a mood effective for this kind of work.

It's Not Always About Change
Allowing yourself the temporal, mental, and physical space to really dream won't always take you towards something new. It may simply confirm that you love the path you're on.

Design For Bad Days, Too
I was coaching an executive recently who felt awful about having a day where he felt completely unproductive. Through discussing, it came out that the day before, he had closed the deal on what was a many months-long engagement. While it's natural to think "ok, it's done, it's time to move on", that can be a very emotionally draining experience - win or lose. It may simply be the case that in some instances, something will cause you to need to step back and recharge, or simply recognize you won't be at your best. Rather than feel bad if and when that happens, plan for it. Set a small number of days aside that you expect to be off so that when they happen you give yourself permission, rather than beat yourself up.

Batch and Sprint
These retreats are not just to imagine and plan, but to work. Perhaps the greatest benefit of good amounts of time to yourself is to give yourself the opportunity for extended deep work. Computer science professor and renown self-help author Cal Newport describes deep work as

Professional activity performed in a state of distraction-free concentration that push your cognitive capabilities to their limit. These efforts create new value, improve your skill, and are hard to replicate.

Last year, I took three weeks in an Airbnb in LA and spent the first week taking Sales Jiu-Jitsu from rough draft to nearly the final edit. With time to yourself and isolation you can sprint and get an incredible amount done in a relatively short window. In a full week or an hour per day over a few months, you can ready many books, educating yourself on a topic or learn the most important 20% of a new skill. Depending on the amount of time and space you're able to get, you can use these practices as an opportunity to produce a great amount of work.

Pick Your Time and Frequency
My co-facilitator from the Open ExO presentation, Trae Ashlie-Garen follows her process quarterly. You may like it twice per year or once per month. You may find this nowhere near New Years, but be in a position where you could both benefit from it and be able to get a good amount of time. Use as much or as little of it for as long as you like, whenever you like.

I'm not sure it is a word — if not it should be — but cognisthesia evokes the idea of being able to feel thoughts. I get a visceral sense that feels like an extension of my brain spreading out when I see all of my ideas and dreams mapped out across a room. It's incredibly freeing and adds an invigorating dimension to goal setting-type practices - and something you may enjoy, too.

This has been an immensely helpful process for me and I’m actually about to jump into it now, a bit late, at the end of 2020. In different ways, it has been a tumultuous, disruptive year for each of us, not to mention the world as a whole. There is good and bad in everything and we have the capacity to take bad things and make them good. But that starts with figuring out what we (really) want and giving ourselves the tools to get it.

Wishing you an incredible new year, full of health, connection, inspiration, and impact!


Martial Artist, Philosopher, Writer

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