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9 Learnings from an Entrepreneur Retreat

Sahil Bloom

Welcome to the 242 new members of the curiosity tribe who have joined us since Wednesday. Join the 57,887 others who are receiving high-signal, curiosity-inducing content every single week.

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How to customize formatting for each rich text

Headings, paragraphs, blockquotes, figures, images, and figure captions can all be styled after a class is added to the rich text element using the "When inside of"

nested selector

system.

Last week, I co-hosted a retreat for a small group of very successful entrepreneurs in Cabo, Mexico.

The group had collectively built businesses and media platforms that have positively impacted millions of people around the world. On the surface, all of them had reached the summit of their mountain, but each one is at an inflection point in determining what comes next.

The explicit goal of the retreat was to help work through this challenge—to wrestle with the big questions, address the insecurities, harness the excitement, and unlock the next phase of growth.

Whenever I find myself around people I admire, I make a point of documenting what I’m observing and learning—partially for my own benefit, and partially so that I can share those insights with all of you, to include you in that growth journey that I’m on.

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

With that in mind, here were my 9 non-obvious learnings from the experience:

Learning 1: If you want to think bigger, get in bigger spaces.

Your environment creates your entire reality. When you spend time in big, open, inspiring spaces, your mind becomes big, open, and inspired.

I don’t know how it happens, but within minutes of arriving, staring out at the grand expanse of the ocean, seeing the beautiful villa, and breathing the fresh air, everyone independently mentions feeling inspired to think big.

If you’re feeling stuck (on a project, or in life), go outside for a short walk in nature, spend a day at the beach, get yourself into a big, open, bright space. I guarantee your entire mindset will shift.

Big spaces catalyze big thinking.

Learning 2: Vulnerability breeds strength.

We start the formal retreat programming on the first night, with each person introducing themselves and providing context on who they are and what their current challenge is (what we call the “most important thing”).

As co-host, I went first and opened with a raw story of my journey, struggles, and insecurities.

Leading with vulnerability, rather than bravado, immediately set the tone for the group—everyone that followed shared raw, real, personal stories that cut to the heart of who they are and their true motivations.

We all assume that masking our insecurities is the way to be strong, but it couldn’t be further from the truth. Opening up about these insecurities breeds strength—it encourages others to do the same and brings everyone together in a web of support and love.

It’s a reminder that we’re all struggling our way through this journey together. Being honest about that fact with yourself and others is how you become strong.

Learning 3: Freedom is the real goal.

For all the financial and business success in the room, it was clear that many of the attendees did not feel rich.

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

Conflating money and freedom is the mistake that people often make—they assume that more money equals more freedom. In reality, money is a tool that can be used to gain freedom, but more often, it becomes a liability that keeps you running for more.

Once you’ve achieved a baseline 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.

Learning 4: Being impressive to others is overrated.

One of the attendees was a legendary hockey player named Chris Pronger.

When another attendee opened up about the fact that he was pursuing a specific path because he wanted to sound impressive to others, Chris delivered a point that hit me hard:

“Being impressive to others is overrated. You know what’s much more important? Being impressive to yourself.”

He had been at the pinnacle of his field, but he realized that everyone thinking you’re great means nothing if you don’t think you’re great.

Focus on the internal, not the external. Be impressive to yourself.

Learning 5: You’re never too far along to change the narrative.

Many of the attendees had a broad desire to rebrand themselves in some way, shape, or form. They no longer wanted to feel trapped by a single narrative, but had a fear that it was too late, that they had come too far and couldn’t make a change after so many years.

In my experience, that is a common struggle—the same struggle someone feels when they’ve been on one track and have a deep desire to be on another.

One powerful realization: You’re never too far along to change the narrative. You are in control of your story. If you’re inspired, it doesn’t matter how many years you’ve been on a path, or how many people know you for that one thing, you can make a change. Slowly at first, then all at once.

Learning 6: Planning is overrated, doing is underrated.

While I was at the private club in Cabo, I was lucky to have a long conversation with a billionaire industrials entrepreneur.

I asked how he had come up with the idea for his business. He said the big idea had come to him in the ninth year of struggling through the mud.

It reminded me of an amazing quote:

“As you start to walk on the way, the way appears.” - Rumi

Ambitious people place so much emphasis on planning: Creating the perfect strategy, business plan, and roadmap. But the reality is that the people we admire just started walking—and the way eventually appeared. That "a-ha!" moment of blinding insight is often on the other side of years of gritty effort.

A powerful reminder for everyone out there waiting for the perfect moment, idea, or insight to strike: Just start walking.

Learning 7: Lack of structure is one of the greatest challenges of entrepreneurship.

In my opinion, the single greatest challenge facing new entrepreneurs is a lack of structure in the days.

If you’re coming from a traditional path, you’ve grown accustomed to knowing what to do, when to do it, and how to do it.

Entrepreneurs know none of these things, but still need to find a way to thrive.

The best advice I can offer: If you’re making the change from a traditional path to an entrepreneurial one, create clear structure to your days. Even if it’s malleable and subject to change, having a general sense of what you do at specific times of day will help ease the tension of the transition to a naturally structure-less environment.

Learning 8: Every day you start at zero.

From the most successful entrepreneur to the person just starting out on the journey, everyone shares one reality: Every single day, you start at zero.

You have to earn your keep, day in, day out. Rent is due daily.

Build your showing up muscle—take pride in punching the clock and you’ll thrive.

Learning 9: The word “yet” will completely change your life.

You have no idea what you’re capable of. To find out, you have to embrace a “yet” mindset:

"I'm not capable of that" becomes "I'm not capable of that...yet."

"Yet" is your one word reminder that you can achieve anything that you set your mind to. You are dynamic and capable of so much more than you realize.

The only way to find your true capability is to push yourself out of your comfort zone. To take that risk. To embrace that pain. Sometimes you'll crash and burn. But sometimes you'll find that you were capable of much more than you ever thought possible.

Embrace the "yet" and change your life.

Those were my 9 learnings from the event.

One important truth I’m consistently reminded of: If you put yourself in the right rooms, the right things will happen.

I’m making it a personal mission to create more of these rooms—physically and digitally—so that others can benefit from being in them the way I have. I don’t have a formal plan to do so, but I’m just going to take my own advice and start walking…

I hope this piece was one tiny step in the right direction.

My co-host, business partner, and dear friend, ​Matt Schnuck​

9 Learnings from an Entrepreneur Retreat

Sahil Bloom

Welcome to the 242 new members of the curiosity tribe who have joined us since Wednesday. Join the 57,887 others who are receiving high-signal, curiosity-inducing content every single week.

What’s a Rich Text element?

The rich text element allows you to create and format headings, paragraphs, blockquotes, images, and video all in one place instead of having to add and format them individually. Just double-click and easily create content.

Static and dynamic content editing

A rich text element can be used with static or dynamic content. For static content,

just drop it into any page and begin editing. For dynamic content, add a rich text field to any collection and then connect a rich text element to that field in the settings panel. Voila!

  • mldsa
  • ,l;cd
  • mkclds

How to customize formatting for each rich text

Headings, paragraphs, blockquotes, figures, images, and figure captions can all be styled after a class is added to the rich text element using the "When inside of"

nested selector

system.

Last week, I co-hosted a retreat for a small group of very successful entrepreneurs in Cabo, Mexico.

The group had collectively built businesses and media platforms that have positively impacted millions of people around the world. On the surface, all of them had reached the summit of their mountain, but each one is at an inflection point in determining what comes next.

The explicit goal of the retreat was to help work through this challenge—to wrestle with the big questions, address the insecurities, harness the excitement, and unlock the next phase of growth.

Whenever I find myself around people I admire, I make a point of documenting what I’m observing and learning—partially for my own benefit, and partially so that I can share those insights with all of you, to include you in that growth journey that I’m on.

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

With that in mind, here were my 9 non-obvious learnings from the experience:

Learning 1: If you want to think bigger, get in bigger spaces.

Your environment creates your entire reality. When you spend time in big, open, inspiring spaces, your mind becomes big, open, and inspired.

I don’t know how it happens, but within minutes of arriving, staring out at the grand expanse of the ocean, seeing the beautiful villa, and breathing the fresh air, everyone independently mentions feeling inspired to think big.

If you’re feeling stuck (on a project, or in life), go outside for a short walk in nature, spend a day at the beach, get yourself into a big, open, bright space. I guarantee your entire mindset will shift.

Big spaces catalyze big thinking.

Learning 2: Vulnerability breeds strength.

We start the formal retreat programming on the first night, with each person introducing themselves and providing context on who they are and what their current challenge is (what we call the “most important thing”).

As co-host, I went first and opened with a raw story of my journey, struggles, and insecurities.

Leading with vulnerability, rather than bravado, immediately set the tone for the group—everyone that followed shared raw, real, personal stories that cut to the heart of who they are and their true motivations.

We all assume that masking our insecurities is the way to be strong, but it couldn’t be further from the truth. Opening up about these insecurities breeds strength—it encourages others to do the same and brings everyone together in a web of support and love.

It’s a reminder that we’re all struggling our way through this journey together. Being honest about that fact with yourself and others is how you become strong.

Learning 3: Freedom is the real goal.

For all the financial and business success in the room, it was clear that many of the attendees did not feel rich.

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

Conflating money and freedom is the mistake that people often make—they assume that more money equals more freedom. In reality, money is a tool that can be used to gain freedom, but more often, it becomes a liability that keeps you running for more.

Once you’ve achieved a baseline 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.

Learning 4: Being impressive to others is overrated.

One of the attendees was a legendary hockey player named Chris Pronger.

When another attendee opened up about the fact that he was pursuing a specific path because he wanted to sound impressive to others, Chris delivered a point that hit me hard:

“Being impressive to others is overrated. You know what’s much more important? Being impressive to yourself.”

He had been at the pinnacle of his field, but he realized that everyone thinking you’re great means nothing if you don’t think you’re great.

Focus on the internal, not the external. Be impressive to yourself.

Learning 5: You’re never too far along to change the narrative.

Many of the attendees had a broad desire to rebrand themselves in some way, shape, or form. They no longer wanted to feel trapped by a single narrative, but had a fear that it was too late, that they had come too far and couldn’t make a change after so many years.

In my experience, that is a common struggle—the same struggle someone feels when they’ve been on one track and have a deep desire to be on another.

One powerful realization: You’re never too far along to change the narrative. You are in control of your story. If you’re inspired, it doesn’t matter how many years you’ve been on a path, or how many people know you for that one thing, you can make a change. Slowly at first, then all at once.

Learning 6: Planning is overrated, doing is underrated.

While I was at the private club in Cabo, I was lucky to have a long conversation with a billionaire industrials entrepreneur.

I asked how he had come up with the idea for his business. He said the big idea had come to him in the ninth year of struggling through the mud.

It reminded me of an amazing quote:

“As you start to walk on the way, the way appears.” - Rumi

Ambitious people place so much emphasis on planning: Creating the perfect strategy, business plan, and roadmap. But the reality is that the people we admire just started walking—and the way eventually appeared. That "a-ha!" moment of blinding insight is often on the other side of years of gritty effort.

A powerful reminder for everyone out there waiting for the perfect moment, idea, or insight to strike: Just start walking.

Learning 7: Lack of structure is one of the greatest challenges of entrepreneurship.

In my opinion, the single greatest challenge facing new entrepreneurs is a lack of structure in the days.

If you’re coming from a traditional path, you’ve grown accustomed to knowing what to do, when to do it, and how to do it.

Entrepreneurs know none of these things, but still need to find a way to thrive.

The best advice I can offer: If you’re making the change from a traditional path to an entrepreneurial one, create clear structure to your days. Even if it’s malleable and subject to change, having a general sense of what you do at specific times of day will help ease the tension of the transition to a naturally structure-less environment.

Learning 8: Every day you start at zero.

From the most successful entrepreneur to the person just starting out on the journey, everyone shares one reality: Every single day, you start at zero.

You have to earn your keep, day in, day out. Rent is due daily.

Build your showing up muscle—take pride in punching the clock and you’ll thrive.

Learning 9: The word “yet” will completely change your life.

You have no idea what you’re capable of. To find out, you have to embrace a “yet” mindset:

"I'm not capable of that" becomes "I'm not capable of that...yet."

"Yet" is your one word reminder that you can achieve anything that you set your mind to. You are dynamic and capable of so much more than you realize.

The only way to find your true capability is to push yourself out of your comfort zone. To take that risk. To embrace that pain. Sometimes you'll crash and burn. But sometimes you'll find that you were capable of much more than you ever thought possible.

Embrace the "yet" and change your life.

Those were my 9 learnings from the event.

One important truth I’m consistently reminded of: If you put yourself in the right rooms, the right things will happen.

I’m making it a personal mission to create more of these rooms—physically and digitally—so that others can benefit from being in them the way I have. I don’t have a formal plan to do so, but I’m just going to take my own advice and start walking…

I hope this piece was one tiny step in the right direction.

My co-host, business partner, and dear friend, ​Matt Schnuck​