The Second Climb

Shawn Weston💥
May 21, 2018 · 5 min read

There I was, trying to design 14 websites at once. Most of them were past due, the money was gone, and I couldn’t afford to take any more projects — I was already working 20 hours a day trying to catch up. People were screaming at me, and it was all on my shoulders.

It was a literal nightmare.

I had two kids under the age of two, and I never got to see them. The “business” I had built for myself was just another prison of a job, only without the regular paycheck. I knew I was talented, and I had been doing this a long time… but I was missing something. There were people who did this without going bald, right? People ate and slept?

I started having chest pain, but I didn’t go to the doctor. Insurance is one of those things you give up for a while in pursuit of “the better life,” so I crossed my fingers and kept going.

I realized that I could get more done if I slept a few hours during the day and worked through the night instead, while the rest of the world was dead. I kept pressing through. I worked more and more, saw my spouse less and less. They found another man who could pay attention to them. And then I was alone.

Daddy, um, playing in a fort with the kids.

Four months later, the projects disappeared again, as often happens in the feast-and-famine struggle of being a solopreneur. No matter how many calls I made, no matter how many Craigslist ads I responded to, I just couldn’t close them.

It was like that episode of Twilight Zone where the book lover is finally left alone with his books, only to step on his glasses.


I went through this rollercoaster cycle more than a dozen times in my career, trying to navigate life as a freelance web designer, before I realized the truth:

Design school doesn’t prepare us for the real world.

Not even close. The lessons they taught us are useless. I learned more in one internship than I did in six years of school.

So I quit. The Universe (and my ex) had gifted me with a dead end — in life, in relationships, and in business. And as long as I was starting over, I was going to do it right.

I spent a year shadowing the best, most successful agency owners I could find. I studied them. I took notes. And then I started at the end — my dream life — and engineered my way backwards to make it a reality.


Fast forward.

This morning, I woke up without an alarm. I made coffee, took Cooper (our dog) for a walk, and checked in with Pepper (my assistant). He tells me that I have a meeting with TLP, a nonprofit I’m helping in my free time. That gives me three hours of deep work this morning, so I grab a notebook and go work in the park.

I feel like doing strategy work today, so I map out two new websites using the research and data that my team has compiled for me. I enjoy top-level branding work, so I do some brainstorming and pull together two strong directions for a client’s new logo. I fire all of that off to the production team from my iPhone, who works on making that a reality.

Then, I stop to grab lunch and sneak in a quick nap.

Life is very, very good.

I’m no longer stuck in a rat race. I have the bandwidth to take on as many projects as I’d like. Income is predictable and growing, and I’m only hands-on in the parts of business that I truly enjoy, those things which utilize my strengths to the fullest. I can take a vacation and still get paid. I’m not a lonely freelancer; in fact, I’m surrounded by team members who have become close friends.

I’ve learned the secrets that can turn a struggling freelancer into the owner of a solid web design agency. Now, I’m an Agency Boss.


When I was 17 years old, I earned my first black belt. I worked toward that goal for nine years — it wasn’t your average martial art. Tae Kwon Do schools looked like belt factories compared to the training we had to endure.

But I digress.

I stood there on that day, the evening of my black belt ceremony. My family and friends were all there, and I cried. And my father, one of my instructors, told me that even as my training was coming into a close, an entirely new phase of learning was now ahead of me, as the clarification of mastery lies not in learning, but in teaching.

Once one reaches the top of Mount Everest, the second climb happens through others as he turns around and helps them get to where he’s been.

Yesterday, I got an Instagram DM from a freelancer who had quit his job to chase his solopreneur dreams. Six weeks later, he found out his wife is expecting. He needs a strategic plan in place, yes… but mostly, he needs hope.

This next climb is for him. It’s for me.

And it’s for you.


Hey there! It’s no secret that design school doesn’t prepare you for the real world, so I started the AgencyBoss community to bridge that gap for you. Check out your new mentorship community! Just click here and get ready to learn.

Shawn Weston is an author, award-winning designer, #AgencyBoss, and daddy of two. Follow me on Twitter | Connect with me on Facebook


This story is published in The Startup, Medium’s largest entrepreneurship publication followed by 326,962+ people.

Subscribe to receive our top stories here.

The Startup

Medium's largest active publication, followed by +492K people. Follow to join our community.

Shawn Weston💥

Written by

The Startup contributor. Author, award-winning designer, and daddy of two. Founder of the #AgencyBoss community. (AgencyBoss.co)

The Startup

Medium's largest active publication, followed by +492K people. Follow to join our community.

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch
Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore
Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade