When It Feels Easy

Read time: 5 minutes

Welcome to The Ascend Archives, a weekly newsletter where I share a story about a transformation, revelation, or change in thinking that has improved an aspect of my life.

This is a follow up to Part 1 and Part 2 of my Fly Fishing Adventure stories.

Quick Note Before Today’s Story:
I’ve been working behind the scenes on the launch of my friend Nathan’s new course, Storytelling: Zero to One. It’s been a blast working with Nathan, especially on a topic I love.

I’ve never promoted anything in this newsletter before, but I’ve gone through the content myself and it’s genuinely improved my storytelling. If that’s something you’re working on or want to become a better storyteller, I think you’ll get a lot out of it.

Click here to check it out

Let me know what you think if you end up jumping in!

I was sitting outside Manana, my favorite coffee shop in Austin, when the voice memo came in.

It was a sunny Tuesday and I was cranking out a few LinkedIn posts for a client. March was shaping up to be my biggest month yet. Things were steady and I was in a solid routine with work, fitness, and life.

The message was from Barrett.

It was long…over three minutes. I didn’t press play right away. Just stared at the text on my screen for a second, then locked my phone and went back to work.

A few hours later, I went for a walk.

No headphones. Just walking the trail around Lady Bird Lake, watching folks enjoy the sun, and anticipating what could be on the voice memo. 

I pressed play. 

“I’m reaching out to you more in a friend and peer capacity than as your coach…”

My heart skipped. 

My mind went straight to worst-case scenarios. Did I say something wrong in the group coaching call? Did I cross a line I wasn’t aware of?

Then he said:

“I went back and forth about whether I should even reach out to you with this…”

I braced.

“But I see an opportunity for us to work together.”

I stopped walking. A grin crept across my face. I could feel the pressure release from my chest.

Barrett, someone I’d looked up to, someone I’d flown across the country to fish with, someone who had once felt out of reach as a speaker at a conference, was now asking if I wanted to collaborate.

He needed help growing his podcast. He had the vision and the ideas, but not enough time to execute. His ambition was to grow the podcast into a self sustaining business and thought I could help him do it.

I left that walk buzzing.

But I also remembered something I learned from my first job after leaving EY: don’t rush into a long-term partnership just because it feels exciting. Date before you marry.

So I sent Barrett a voice note back. I told him I appreciated the thoughtfulness and transparency. I was aligned. I wanted to explore it. And I proposed we try a three-month project to see how we worked together and what we could build.

He replied the next day: “Let’s do it.”

That’s when the “sales process” began.

We jumped on a short call later that week. Barrett shared more context. I asked questions. We talked openly about what success would look like. We co-created a vision that we both felt good about. 

The next day, I put together a proposed scope of work for this initial project. The goal would be to increase the distribution of his podcast through social channels. I laid out two options: one focused on LinkedIn, the other expanded to include Instagram and recorded a Loom walking through my thinking behind the deliverables, the timeline, and the pricing.

And that’s when the nerves hit.

Pricing is always the hardest part for me. There’s the math of how many hours and what’s my time worth. But then there’s the emotion. The stories I tell myself. Will they think it’s too expensive? Will they say no? Am I overreaching?

This time, it felt even more loaded.

Because I wasn’t just pricing a project. I was pricing an opportunity with someone I respected and who I wanted to work with long term. I wanted to get this right.

So I used Barrett’s own advice, his framework for value-based pricing that he’d taught me a few months earlier in our group coaching program. I considered how much time this project would save him. How it could help him maintain a full client load. How it might raise the ceiling on his business. I did the math. Backed into the value. And sent the Loom.

It was noon on the first Friday of March Madness—my favorite weekend of the year. Four games at a time from morning to midnight. A tradition that started when I was ten and my mom used to let me skip school to watch.

I closed my laptop, cracked a drink, and settled into the couch.

At 5 p.m., my phone buzzed.

“Hope you’re enjoying the games. Just watched your Loom—love the direction. Let’s do the three-month trial. Here’s what I’d tweak…”

By Monday morning, the contract was signed and the invoice was paid.

No chasing. No second-guessing. No “just following up.”

It felt… easy.

And for a moment, I wondered: Was this what it feels like to finally get lucky?

But a few days later, I was out on another one of my no headphone walks. 

And it hit me that the “sales process” didn’t start last week from Barrett’s voice note. 

It started eight months ago.

When I replied to a tweet about a last-minute spot on Barrett’s annual fly fishing trip.
When I booked a flight to Oregon to spend three days floating down the Deschutes River with a group of strangers I’d never met.
When I sat around a dinner table full of seasoned entrepreneurs and said, “I’m not really sure what’s next—but I’m here to figure that out.”
When I stayed in touch afterward.
When I joined his coaching program.
When I offered ideas, shared feedback, and asked nothing in return.

Putting in all that work is what made this week-long sales process feel easy.

I thought back to another sales process I went through a few weeks earlier.

That one felt heavy.

The client wasn’t clear on what he wanted. I was the one pushing things forward. I spent hours writing proposals that never got reviewed. I was waiting around for months. And every time I followed up, it felt a little more desperate.

With Barrett, it was different.

We built the scope together. He knew what he wanted. I knew how I could help. There was history.

And most importantly, there was trust.

As I kicked off the project with Barrett, I started thinking about the cost of that trip to Oregon and the investment in his coaching program. And then I did the math. It almost perfectly matched the value of the 3 month project we had just signed.

This wasn’t luck.

This was the return on a deposit I made eight months ago.

And the best part? This isn’t a one-time return.
It’s just the beginning of something that’s starting to compound.

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