Lessons Learned After a Decade of Being Self Employed

June, 2007, was the month that my husband and I sold our printing business and home, and headed out on an open-ended road trip sabbatical with our three legged dog. The blog we share, LiveWorkDream, chronicles our never-ending journey in search of our “next big thing.”

This post was written in August, 2008, during our stint as “workampers” on a Western Colorado dude ranch.

On Being Self Employed: Freedom from Motivational Posters

Vickers Ranch Hwy 149 Lake City COThis has been a rough week at the ranch. In the span of three days, two workampers quit, the chef got into an accident and might be out for the season, and some guests are being a challenge. I see the look on my boss’ face, and I can relate.

Back in the day, whenever things would get rough while we were running our old business, I would read this quote on the wall above my computer:

“I’d rather be the captain of my own dinghy than a junior officer on the Titanic.”

Dr. James Chan, Author of “Spare Room Tycoon; The 70 lessons of sane self-employment.”

It was a constant reminder of why Jim and I were working countless 12 hour days, jumping through flames to deliver impossible client demands, and barely stopping to catch our breath to show Jerry some love. Yet, despite the endless agonies that go along with being self-employed, I’ve never been happier while making a living.

It took me a long time to figure out that I was meant to run my own business.

I think I went through eleven different office jobs between the time I finished college, in 1992, to the time we got our business going, in 1997. I wouldn’t say I was a bad employee, just easily bored. At almost every place I punched a clock, I hated being expected to fit into a predefined role, and towing the company line. Oftentimes, I wanted to throw a brick at every motivational poster that plastered the cafeteria walls. So I became self-employed. The mistress of my own dinghy.

Gold Hill Vickers Ranch CO

I’m Wearing the Other Shoe Now
After a few years of running our business, it didn’t take me long to gain a real appreciation and understanding of what my former employers went through. Money worries. Taxes. Technology. Unappreciative employees (if any of my old bosses are out there, I wholeheartedly apologize for any bad attitudes and laziness I might have expressed while working for you!).

Yet, despite the headaches that come along with running my own company, I’ll never go back to punching a clock again. If I have one for-sure goal in life, it’s to always stay self-employed.

Meanwhile, back at the ranch, my boss Paulette continues to roll with the punches. She keeps on smiling, and her positive attitude will help her and everyone else get through whatever comes our way this season. Like small business owners everywhere, she does what needs to be done to keep the business galloping along.

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