10 Learnings from a Mastermind

Last week, I spent three days with a group of successful entrepreneurs on a retreat in Big Sky, Montana.

The group had collectively built businesses worth billions of dollars and created thousands of jobs around the world—but while my old self might have been in awe of their financial success, my new self was much more focused on the deeper layers to these individuals, including their purpose, motivations, insecurities, and failures.

I left the event with a new energy to grow and a lot of interesting, non-obvious learnings.

On the flight home, I went through my pocket notebook and attempted to synthesize the most important takeaways from the event.

My 10 key learnings (that everyone needs to hear):

#1: Freedom is the Real Goal

For all the financial success in the room, it was abundantly clear that many of the entrepreneurs did not feel rich.

Why? They lacked freedom (and wanted to fix that).

Conflating money and freedom is the mistake that people seem to make—they incorrectly assume that more money equals more freedom, and wind up disappointed when it does not.

Money is a tool that can be used to gain freedom, but more often, it becomes a tool that keeps us running for more.

Once you’ve achieved a certain level of financial success, everything becomes about a quest for freedom. The ability to do what you want, with who you want, when you want is what everyone prizes above all else.

Freedom is the real goal.

#2: Environment is EVERYTHING

Thinking big is contagious.

When you get a group of ambitious big thinkers in a room, incredible things happen.

Just sitting in the room, the energy gets injected into your veins. When you’re around others who are battling in the arena, you can’t help but follow suit.

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.

#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.

When I was younger, I used to think that achieving some external rewards would rid me of my insecurity—that getting promoted, making more money, or winning some awards would suddenly make me feel perfectly comfortable.

What I've come to realize: The feeling that we aren't doing enough, or may suddenly get exposed as an imposter, is natural.

Opening up about these insecurities, rather than trying to mask them with bravado, is the key to managing their influence on our lives.

#4: Know the Game You're Playing

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

The biggest failures the group had experienced stemmed from either (a) playing a game without understanding it or (b) playing a game with a prize they didn't really want.

It's easy to default into the game that seems most obvious—the one your parents selected for you, the one your course of studies selected for you, the one your risk aversion selected for you.

Before you join the game, always ask:

• Do I know the game I'm playing?
• Do I want the prize for winning this game?

If you can answer "yes" to both, dive in. If not, pause and reassess.

#5: Create Without Expectations

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

Living life as one big transaction, with a constant quid pro quo mentality, will get you nowhere (or at least nowhere worth going).

Those who give to others, to the community, and to the world with no expectation of return will always experience the greatest comprehensive returns.

#6: Owned Distribution is a Cheat Code

All of the entrepreneurs have come to realize what a massive business advantage it is to own your distribution via a personal brand platform and audience.

The older entrepreneurs wish they had it when they were younger—the younger entrepreneurs are building it into the fabric of their current business models.

Everyone views it as a cheat code—a way to do business on easy mode.

#7: Success Isn't Always Loud

The most successful entrepreneur at the event has built a holding company that will be worth over $1 billion. I would have expected him to be assertive, aggressive, and even a bit arrogant.

But he wasn’t the loudest in the room. Not even close.

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 of the modern age.

#8: You Never "Figure It All Out"

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

If you do that, good things will happen.

#9: Entrepreneurial Loneliness is Real

All of the participants talked about the struggles of loneliness while building their companies.

Success is celebrated in the warm light, but the journey is often experienced in the cold dark.

Remember: You don’t have to do it alone. Most of these entrepreneurs had built support systems to make sure they had people around them with whom they could open up and share.

Find your people and walk the path with them.

#10: See It Differently

Sometimes you need to see the problem differently to solve it.

I had several “a-ha!” moments around some business problems I was facing during the retreat.

All of the solutions felt very obvious in hindsight, but somehow my default approach had not worked. The different perspectives from the group allowed me to see the problem differently and break through.

If you've only looked at a problem one way (the way you know how), try looking at it differently. Ask others how they would think about it. Have them pressure test your thinking. Novel perspectives generate novel solutions.

The Room Where It Happens

A few months ago, I was at an event with ~50 entrepreneurs building cool stuff. There was a 21-year-old who had come as a guest of an attendee. We were chatting and he told me he was stressed about his lack of a career plan and asked for my guidance.

"You're crazy," I told him, "If you’re 21 and in these kind of rooms already, the sky is the limit."

This is grounded in a truth I’ve found over and over again in my life: If you put yourself in rooms with smart, ambitious, kind people, great things will happen.

At this stage of my life, my primary professional goal is to spend more time in those rooms. I don't have a specific path or 10-year plan, but I trust that if I am in those rooms, and create value for the others with no expectation of return, I will be just fine.

My Rule for Life: Find the room where it happens. Get in that room. Once you're in it, help others get there.

P.S. Montana is spectacular!

Weekly Reader Question & Advice

I am a Chartered Accountant (equivalent to CPA in US). I've spent almost a decade studying for it but deep down, I developed a love for writing. And now, I have discovered that I can write online and make that a business. I have a job offer for audit but I don't want to pursue that. It's good money. But I just don't see myself there.
On one hand I think that I should stop looking for a job and go head first in freelancing. On the other hand, I think that I should take up the job and start freelance side by side and when I'm confident that I can do this full-time, then leave my job.
I'm very, very confused. I constantly think all the time about what should I do with my life, how my life should be, what my goal is in life. And the worst part is there is no one to guide me. I share everything with my boyfriend and he helps a lot but I have no guide who has been in the same situation as me.​
Can you guide me?
- Twinkle

Hi Twinkle -

6 months of execution will bring a lot of clarity.

I would take the job in audit, but design your days so that you have at least ~1 hour per day to dedicate to your business of the future (freelance writing?). If you do this, after 3-6 months, you’ll have a great body of work on your “new thing” while maintaining the stability of the full time job.

When people dive all in on a side path with no safety net, they make short term decisions out of fear. Example: If I had quit my job before making any money on my writing, I would have “sold out” early for random sponsor deals and money that would have infringed on the quality of the content I was producing. Having the safety net will allow you to think and build for the long term.

As long as you maintain a discipline around the daily action of time towards your next thing, you’ll do great.