Two Things My Last-Ever Job Taught Me

Two Things My Last-Ever Job Taught Me

“What is that?” my wife said.

“Well, it’s a fax machine,” I said with a tone that was like, duh!

“But why did you buy a fax machine? I just don’t get it!”

My wife was upset and she was ruining the thrill that normally comes when unwrapping a shiny new electronic toy from its packaging.

“I just don’t understand, when we have like zero money, how you can justify buying a fax machine?”

“I told you already. I need it so that clients can fax me their contracts.”

“But you don’t have any clients! You haven’t even made a single sale!”

She was right.

Deep down I knew she was right. It stung. It hurt. And it was a huge wake up call.

Would you like to know why I bought the fax machine?

Wait for it… wait for it… I wanted to be a life coach. Yep, but not just any life coach! A professional, “certified” life coach. I already spent $2,500 of borrowed money to pay for a certification and yet, I came out of it with no business plan and no paying clients whatsoever.

Don’t misunderstand me – there’s nothing inherently wrong with being a life coach… as long as it’s founded on real business practices. Which I wasn’t doing.

But I did what I thought I was supposed to do! In my mind, I was already a hugely successful professional, certified, life coach. Now all I had to do was to “create the space” and the business would follow…


I got busy setting up an office for myself. I bought a brand new desk, telephone (yes, a landline), pens & pencils, business cards, and even a freaking fax machine…

For $230…

That we didn’t have.

I had the entrepreneurial desire. I just didn’t have any skills to back it up.


Still no clients and still living on borrowed money. With my tail between my legs, and a kid on the way, I returned to the land of employment. After some searching on Craigslist and schmoozing some placement agencies, I landed a good-paying job that was close to home.

I wasn’t free to hang out with my family whenever I wanted, but at least we had money for rent.

With the new job, something marvelous happened.

I learned two very important things:

  1. I just wasn’t cut out to have a job – my personal freedom was way too valuable for me to give up
  2. I needed to learn how to create a real, profitable business that would allow me to leave the land of employment forever

The best way to predict the future is to create it.


With a head full of Tim Ferriss (The 4-Hour Workweek) and Gary Vaynerchuk (Crush It), I started my own business. This time I knew exactly what I needed to do. I already spent every spare moment I had learning general business skills and focusing heavily on sales and marketing. After all, in business if you don’t have sales, you don’t have anything.

I wasn’t interested in creating the next Google. I didn’t want investors. I didn’t want a job. I didn’t even want millions of dollars.

What I wanted was a lifestyle.

I wanted to do whatever I wanted, whenever I wanted, with whomever I wanted. And I wanted a business to pay for it. In other words, I set about to create a lifestyle business.

I got started by bootstrapping and selling services to real paying clients. In my first 30 days, I made $2,450. Certainly nothing to brag about but I was ecstatic. I had proof that I could sell and that I could make money without a job.

After that first month, I spent the next two years scaling the business. I put systems in place. I put a team in place. I got on top of my business. And then I took off to live in the Caribbean for 2 1/2 years together with my family.

Then I spent a year back home in Southern California. And then another two years in Cozumel, Mexico. And now I’m living in Edinburgh, Scotland.

All paid for by the business I created.

When I reflect on that previous Sean, the Sean who desperately wanted to be free but had no idea how, I can’t help but think of all of the emails I’ve received.

They’re emails from people also looking to free themselves from their jobs, start a profitable business, and just plain have a better life together with their loved ones.

And that’s who this blog is for.

It’s for all the “Sean’s” out there who can’t stand sitting in traffic only to sit in a cubicle all day. It’s for all the people out there who see photos of tropical beaches or castles in Europe or safaris in Africa or outback adventures in Australia and dream of being there themselves.

It’s for all the people who want to start a business and make their own money but aren’t sure where to begin. It’s for all of the people that just plain want to decide what they’re going to do on a Tuesday morning.

If this describes you in any way, well then my new amigo, you’re in the right place. Let’s discover together how you can create your own business and start living the life of your dreams.

It’s not fluff. There’s no rah-rah here. Just real principles from a guy lucky enough to have pieced it together. If you’re ready, let’s get started towards the lifestyle you deserve.


This is part of an ongoing series of posts all pulled from the book: The 60-Day Entrepreneur – Create Your Own Lifestyle Business, Scale Your Income, & Live Life on Your Terms

For your own free e-version of this book, click on the image below60 Day Entrepreneur