The Stupidest Thing I Ever Did As a Business Owner.

In 2007, I worked as a freelancer at the biggest, baddest¹ agency in town building Flash websites.

I would show up every morning, sit in my cubicle, write code, and make big bucks.²

And I was miserable.³

The illustrious views from the 25th floor of that downtown highrise were stunning, yet I felt trapped behind the floor-to-ceiling glass.⁴

I was expected to be on site 9–5, and my co-workers were driven to succeed.⁵

My customer controlled where, when, and with whom I did business.

Umm….anyone see a problem here?

The ONLY 3 Benefits of Owning a Business

There are only three benefits to owning a business:

  1. You get to decide where you work.
  2. You get to decide with whom you work.
  3. You get to decide when you work.

Exactly like this:

There Is Hope.

If you own a business or are freelancing and you are giving up any one of those three benefits (where/when/who), then strongly-consider either:

Throwing in the towel and working for someone else.
Altering your business to better align your why/when/who with your life.
If you are going to stay in business, then get curious about why you are doing things the way you are.

It’s likely there is a path to a better future sitting there right in front of you.


p.s. If you’d like to work on getting your business better-aligned with your life, drop me a note with some times we can chat next week:


¹ a.k.a. conceited & arrogant

² Dollar amounts are relative to a 24-year-old living in a 1-bedroom apartment with his cat and no furniture — literally no furniture. Yeah.

³ My misery having nothing to do with aforementioned lack of furniture…

⁴ I am totally aware that this is something of a WPP. Still, if we can make our lives marginally-better without hurting anyone, no matter what our place in the world, why not do it?

⁵ i.e. They were passive-aggressive assholes. Or maybe I sucked at my job — either way, there was a problem with communication, to say the least…

Toby Cryns

Toby Cryns is a freelance CTO and WordPress Guru. He also writes for