I spent three days with a group of multimillionaire entrepreneurs in Montana.

10 key learnings (that everyone needs to hear):

1. Freedom is the real goal. Once you’ve achieved a certain level of financial success, everything becomes about a quest for freedom. Being able to do what you want, when you want, with who you want is what everyone prizes above all else, but few have it.

2. Success isn’t loud. The most successful entrepreneur at the event has built a holding company that will be worth over $1 billion. He wasn’t the loudest in the room. On the contrary, he was quiet and highly observant. When he did speak, it was with an incredible ability to penetrate to the heart of the topic or issue. Listening, observing, and thinking is a superpower.

3. Insecurity is a natural human condition. These entrepreneurs have built incredible companies and personal wealth, but all open up privately about their personal and professional insecurities. The feeling that we may get exposed as an imposter is natural. Opening up about those insecurities, rather than trying to mask them with bravado, is the key to managing their influence on our lives.

4. Always know the game you’re playing and whether you want the prize for winning that game.

5. If you create value with no expectation of return, you will experience the greatest returns.

6. Owned distribution is a cheat code. All of the entrepreneurs realize what a massive business advantage it is to own your distribution via a personal platform and audience. They are building it into the fabric of their businesses. Everyone views it as a cheat code—a way to do business on easy mode.

7. Environment is EVERYTHING. It’s hard to explain, but thinking big is contagious. Just sitting in the room, the energy gets injected into your veins. Note to self: Get in more of these rooms. Another note to self: Create more of these rooms where others can benefit from them the way I have.

8. No one knows what they want to be when they grow up. The group ranged in age from 30 to 60, but no one seemed to have everything about their future figured out. It’s comforting as a young person to know that you aren’t really supposed to “figure it out” when it comes to your future. Just focus on pointing your compass in the right direction, embracing curiosity, getting around great people, and good things will happen.

9. Entrepreneurial loneliness is a real problem. You don’t have to do it alone. Most of these entrepreneurs had built support systems to make sure they had people around them.

10. Sometimes you need to see the problem differently to solve it. I had several “a-ha!” moments around some problems I was facing during the retreat. All of the solutions felt very obvious in hindsight. The different perspectives allowed me to see the problem differently and break through.

When stumped by a lifechoice, choose “enlargement” over happiness. I’m indebted to the Jungian therapist for the insight that major personal decisions should be made not by asking, “Will this make me happy?”, but “Will this choice enlarge me or diminish me?”

There will always be too much to do – and this realisation is liberating. The only viable solution is to make a shift: from a life spent trying not to neglect anything, to one spent proactively and consciously choosing what to neglect, in favour of what matters most.

Andrea Zittel: These things I know for sure

– as of January 6th, 2020

1. It is a human trait to want to organize things into categories. Inventing categories creates an illusion that there is an overriding rationale in the way that the world works.

2. Surfaces that are “easy to clean” also show dirt more. In reality, a surface that camouflages dirt is much more practical than one that is easy to clean.

3. Maintenance takes time and energy that can sometimes impede other forms of progress such as learning about new things.

4. All materials ultimately deteriorate and show signs of wear. It is therefore important to create designs that will look better after years of distress.

5. A perfected filing system can sometimes decrease efficiency. For instance, when letters and bills are led away too quickly, it is easy to forget to respond to them.

6. Many “progressive” designs actually hark back towards an ideal of something lost – for instance a more “natural” or “original” form.

7. AAmbiguity in visual design ultimately leads to a greater variety of functions than designs that are functionally fixed.

8. No matter how many options there are, it seems to be human nature to narrow things down to two polar, yet inextricably linked, choices.

9. The construction of rules is more creative than the destruction of them. Creation demands a higher level of reasoning and draws connections between cause and effect. The best rules are never stable or permanent but evolve naturally according to context or need.

10. What makes us feel liberated (and consequently more creative) is not total freedom, but rather living in a set of limitations that we have created and prescribed for ourselves.

11. Things that we think are liberating can often become restrictive and things that we think of as controlling can sometimes give us a sense of comfort and security.

12. Ideas seem to gestate best in a void—when that void is filled, it is more difficult to access them. In our consumption-driven society, almost all voids are filled, blocking moments of greater clarity and creativity. Things that block voids are called “avoids.”

13. Sometimes, if you can’t change a situation, you just have to change the way that you think about the situation.

14. People are most happy when they are moving forward toward something not quite yet attained. (I also wonder if this extends as well to the sensation of physical motion in space... I believe that I am happier when I am in a plane or car because I am moving towards an identifiable and attainable goal.)

15. What you own, owns you.

16. Personal truths are often perceived as universal truths. For instance, it is easy to imagine that a system or design that works well for oneself will also work for everyone else.

17. Thoughts are “designed” just like everything else around us.

18. The easiest way to establish a new desirable habit is by bundling it with an already established habit or pattern. For instance, I remember to feed the dogs and cats while I am waiting for water to boil for my morning tea. Or, I water the plants when I am waiting for the bathtub to fill.

19. Demands are more oppressive than restrictions. A to-do list is an example of a demand – you become so caught up in the list that you lose the ability to actively prioritize what is most important at any given moment. Restrictions, however, create parameters that limit certain activities in order to allow room for other things that are often hard to find time for (reading, listening to oneself think, crocheting sweaters). In other words, it is better to restrict yourself from doing certain activities than it is to add more things to your to-do list.

20. Space can’t be “made”, instead it is denoted by boundaries, divisions, walls, compartments, etc. In essence, space is created by the physical boundaries that we build to contain it.

21. Creating quotas is the best way to make sure that basic needs are met without falling into the mindset of always wanting more. Once your quota is met, you must give up something that you already own in order to acquire something new. Sample quotas for an individual are: seven t- shirts, seven pairs of underwear, seven socks, two skirts or pairs of jeans, two fitted sheets, four pillowcases, two comforter covers, and two bath-towels.