Last week, after I sent my newsletter, my friend Lindsay (a loyal Browns fan) replied with a simple question.

She wanted to learn more about my 90 Conversations in 90 Days project.

At the bottom of my newsletter, I'd included a link to where I'd documented the experiment on LinkedIn. After clicking around for a while, she wrote back and said, "It's really hard to follow."

She was right.

At first, I thought the problem was the link.

It wasn't.

The problem was that I'd left one of the most valuable things I've ever created buried inside dozens of LinkedIn posts.

I'd forgotten how much was actually there.

A couple of years ago, I found myself in a season where life looked very different than I expected. COVID had changed my business almost overnight. Many of my clients had either lost work or put projects on hold. Around the same time, my dad became seriously ill, and caregiving became a much bigger part of my life than I'd ever imagined.

By the time things began to settle, I realized something else had quietly disappeared.

Conversation.

I've always done my best thinking with other people.

Around that time I was listening to a podcast when the guest mentioned that whenever he needed to refill his creative tank, he talked to people.

At that moment, I realized…

Me too!!!!

Almost immediately I remembered hearing about a challenge another entrepreneur had given herself when she was starting her business: 90 conversations in 90 days.

I love a good challenge.

Give me a silent retreat, a juice cleanse, or a clear finish line, and I'm in.

So I borrowed the idea and made it my own.

The goal wasn't networking.

It wasn't selling.

It wasn't collecting leads.

It was simply to become curious again.

Over the next few months I met with people from every stage of life…

Old friends, former colleagues, people I admired, complete strangers.

After every conversation, I wrote about what I'd learned.

Looking back through the data recently, one insight surprised me.

It took almost three weeks before I found my rhythm.

At first, reaching out felt awkward. Scheduling took effort. Some conversations were canceled. Some people didn't show up to our Zoom meeting. I wondered whether the project was worth it.

Then something shifted.

Conversations became easier to schedule.

Introductions started happening naturally.

Ideas multiplied.

Momentum replaced resistance.

People showed up unexpectedly.

As I considered past challenges, it reinforced what I already knew from my past experiences as an actor preparing for auditions, building a business, and even beginning this newsletter.

And now, introducing The Possible-ist to the world, and writing my book.

We often mistake the awkward beginning for evidence that something isn't working.

Sometimes it's just the price of getting back into motion.

As I revisited the project, I realized something else.

The conversations themselves were only half the experiment.

The other half was learning to capture what I was discovering. Those conversations became inspiration for LinkedIn posts. Later, they became data I could analyze. More recently, they've become material I've been exploring with AI to better understand patterns I couldn't easily see on my own.

One conversation became dozens of ideas.

That's the gift of documenting your work.

So thank you, Lindsay.

A broken link ended up pointing me back to something I'd forgotten I already had.

Over the next few weeks, I'm going to start sharing some of the lessons from that project, not just because I think everyone should challenge themselves to 90 conversations in 90 days, but because I think every meaningful chapter in our lives begins with one conversation we're willing to have.

What's one conversation you've been putting off that might be worth having?

And if it's with me… double your points. ;)

Here's a link to schedule a coffee conversation to get you started.

Until next time,