I just co-hosted a retreat for a small group of very successful entrepreneurs in Cabo, Mexico. The explicit goal of the retreat was to help work through a big challenge facing each attendee.

My goal is to “bring you into the room” so that you can feel the impact of the experience in your own careers and lives.

With that in mind, this piece shares my 9 non-obvious learnings from the retreat.

Question: How am I creating the situation that I don’t want?

Framework: The Bricklayer Mentality

Because of the gigantic shift in my life over the last three years, I'm often asked about how to take the metaphorical leap of faith. To answer that question for anyone who has asked, and anyone who might be thinking about it, here's my definitive player's guide to the leap of faith.

The leap of faith you want to take in life is so scary because of the size of the change. It is a 100 foot gap from where you are to where you want to be, with nothingness in between. The 100 foot gap is the problem to be solved.

3 steps to shorten the gap into something manageable: (1) Gather information, (2) Create evidence, and (3) Address the fear.

Question: If you knew you would die in 10 years, what would you do today?

Framework: Use the Difficulty

If you've been reading my work for a while, you know that I'm a big proponent of the simple, boring basics. I don't have any e-books to sell you. I just want to see you make progress. This piece shares my favorite—very simple, very boring, and very effective—strategy for making dramatic progress in any arena: The 30-for-30 Approach.

With whatever you're trying to improve at, do it for 30 minutes per day for 30 straight days. It works because the 30 minutes is low intimidation, the 30 days is a meaningful commitment, and the 900 minutes of accumulated effort creates surprisingly significant results.

Question: When was the last time you allowed yourself to celebrate good enough?

Framework: The Click Test

"There's a guy in my head, and all he wants to do is lay in bed all day long, smoke pot, and watch old movies and cartoons. My life is a series of stratagems, to avoid, and outwit that guy." - Anthony Bourdain

We all have "that guy" somewhere in our head. It may look a bit different from person to person, but the general archetype is universal. You can never silence the voice, you simply learn to resist.

Everything meaningful in life is on the other side of hearing that voice loud and clear and acting in spite of it. Today, and all days, I hope that you outwit "that guy" in your head.

Question: What are you going to be celebrating one year from today?

Framework: The Pygmalion Effect

Last Friday in London, my friend Ali Abdaal and I hosted a live event at the London School of Economics in front of a sold out crowd of 500 people. We covered 10 ideas that changed our lives, on areas ranging from careers to relationships and more.

The 10 ideas we shared: (1) There's no such thing as a loser who wakes up at 5am and works out, (2) Energy is not finite, (3) No one has it all figured out, (4) Direction over destination, (5) Who not how, (6) Increase your luck surface area, (7) Default to trust, (8) The waiting room is always full, (9) The good old days are happening right now, and (10) Time is your most precious asset.

Question: How would the best version of myself show up in this situation?

Framework: Winner's Game vs. Loser's Game