The Diary of a CEO from 7 Years Ago

Read time: 6 minutes

Welcome to The Ascend Archives Friday Edition where I share insights from the brightest minds in business and life and how I'm applying them to my life.

For months, I’d scan past the Diary of a CEO on the top of the Spotify podcast charts.

The title never sparked my interest. I'm not a CEO. I never really aspired to be one.

But during my Adam Grant deep dive, I decided to give it a listen when Adam was interviewed. Out of all the podcasts I listened to with Adam as the guest, this one was my favorite. Not because of Adam, but because of the host, Steven Bartlett.

The best podcast hosts spend hours researching their guests, asking thoughtful questions, and effectively communicating. Steven checks all of those boxes. But he goes a step further. He connects with the guests like nobody I have witnessed.

Through his own vulnerability, storytelling, and listening, he creates an environment that makes his guests feel seen and heard. He allows his guests to show up as their authentic selves because he sets the tone with his own authenticity.

While listening to a recent episode, a guest asked Steven about the start of the podcast and if he would ever return to that format. It was Steven by himself talking directly into the microphone reflecting on his diary entries from the previous week. No script. No interviews. Just raw emotion off the cuff.

For context, Steven is a 31-year-old investor on England’s version of Shark Tank, founder of 3 multi-million dollar companies, and host of a top ranked global podcast.

I wonder what was in Steven’s diary 7 years ago at the age of 24.

I decided to go back in the archives and listen to the first 3 episodes of The Diary of a CEO from 2017. Four topics that Steven was contemplating at the time really resonated with me so I reflected on them myself.

It was difficult answering some of these questions so if any of these resonate with you, I'd love to hear your answers!

1. Why do we believe the grass is always greener on the other side of the fence?

Why do we want things we don't have?

Some of the first examples that come to mind are:

• Someone in a relationship wanting the freedom of being single vs a single person wanting the comfort of a partner

• A corporate employee wanting the autonomy of their own business vs an entrepreneur wanting the stability of a bi-weekly paycheck

• An analytical person wanting to be more artistic vs an artist wanting to be better with finances and investments

I have felt this desire to pursue a life that I didn’t have.

I was in a corporate job where I was making good money, enjoyed the people I worked with, and found the work interesting enough. But there was always this thought in the back of my head about what it would be like to be an entrepreneur. Eventually that thought got loud enough that I quit the stable job to try it out.

It came down to curiosity. I had read books, listened to podcasts, and talked to many entrepreneurs. But eventually I wanted to see for myself what entrepreneurship felt like.

Most people think it’s bad to check out the grass on the other side of the fence because we’ll just realize that we prefer what we already have.

I disagree.

Maybe they are right, we might prefer what we already have. But how do we know for sure until we try? I think it’s totally fine to hop the fence and check out the world of being single, joining a rock band or starting a business. It’s not a one way fence, we can always jump back to where we are today.

2. Our lives are defined by how we spend our time

We can always make more money. But we can't make more time.

How do we make the most of our time on this planet?

I believe it’s by having an abundant mindset and prioritizing doing what I want, when I want, and with who I want.

Last week I was in Costa Rica. The trip ended up costing more than I had budgeted for. All of the hiking was on private property and had entry fees, I ate out more than I planned, and ended up having to rent a car.

I could have let that stress me out and ruin the trip. Instead, I thought about this concept from Steven. I could make more money to pay for this trip, but I couldn’t make more time.

I was in freaking Costa Rica! I was allocating my time doing things that bring me joy: meeting new people, exploring new places, learning about new cultures, and spending time outdoors. I was doing what I wanted with my time and I could find a way to make back the money.

Sure enough on day 8 of my 10-day trip, a client that I hadn’t heard from in over a week agreed to a proposal I had sent. This new client relationship has the potential to more than offset the extra $1k I spent last week.

We can make more money. We can't make more time.

3. What is the end game in this game of life?

We are all going to die. What do I want to achieve before that happens?

Steven talked about it being ok not to have a clear answer here. And I agree.

We are all pressured from an early age to "have it all figured out". But what I’ve learned as I’ve grown older is that nobody has it figured out and nobody can see into the future. On July 12, 2023, I could have never guessed that one year later I would have traveled to 7 more countries, have my own business consulting for creators, and be living back in Austin.

The end game is not about having a perfectly defined life. To me, it’s just being able to look back and say I lived the life I wanted to live; not the life anyone else wanted me to live. And whatever achievements come with that is great.

The life I want to live is an infinite game where success is a feeling. A feeling of flow, of connection, of challenging myself, of gratitude, and of helping others. If I can continuously have those feelings throughout my lifetime, then that’s a win in my book.

4. The thing that connects you to other people is your story

Steven’s story is of a kid from Africa, raised in the UK as the poorest kid in his neighborhood. A kid who was embarrassed of how he looked and where his family came from. A kid who didn’t do well in traditional education so he dropped out of college and started his own businesses at the age of 18. He always had a desire to help people, but instead of helping others first, he focused on himself. He built a massive business empire that now allows him to impact hundreds of thousands of people across the world.

What is my story?

My story is about a guy who was crushing it on the traditional path. The straight A student, captain of the basketball team, editor in chief of the newspaper, and student government treasurer. The guy who attended a top university and landed a prestigious job at a consulting firm. The guy who was engaged to his high school sweetheart by 26 years old where they had the dog, the house, and the perfect wedding planned. The guy who had everything just as it was designed.

But then it blew up in his face. The relationship abruptly ended. The condo and ring were sold off for a loss. It was time to start over from scratch. After months of mourning, it was time to figure out who he was and what he wanted. He began to build his life by design.

That's what led me…

To Austin

To writing

To start my business

To go on epic adventures

To race in Ironman competitions

To meet new people and build relationships

To form deeper connections with my friends and family.

That is my story. And the best part? It’s only Part 1.

Thank you for reading! As always please reply and let me know what resonated, what didn’t, or what you question. I love chatting about this stuff!

Cheers,

Andrew