Did You Work for a Bad Boss?

This winter, my body has decided that it would pick up every cold going around.  Being sick sucks for anyone, but being sick when you’re an entrepreneur is especially stressful.  There is no one to carry the torch when you’re ‘out of the office’, and often you just have to push through.

There are a lot of reasons to start a business.  The best reasons usually involve a level of passion and expertise which carry us through the hard times (like having a cold).  But so many of us started our own business because we had a bad boss.  We felt a lack of empowerment, misdirection, overcomplication of our jobs, lack of acknowledgement, and sometimes were penalized for not being ‘yes men’.  Are you nodding yet?  You’re definitely not alone, and your reasoning isn’t wrong.  However, it’s important to jump in with eyes wide open.

My Entrepreneur Story

My first business, a nonprofit organization, was started for the first reason — passion.  I wanted to help people serve my community.  My second business, a web company still running today, was started as a reaction to a bad boss.

Honestly, I didn’t know what else to do.  I watched a talented young man with little business savvy hire 16 contractors, then fire them two months later due to ‘budget cuts’.  One week we were buying Dom Perignon to celebrate landing a six-figure client, the next he was raging around the office because Google had once again changed the algorithms on which his business was built.

Finally, he realized he was better suited to do the job and not run a business (a lucrative offer came through from a larger company which helped).  He sold the company to our main client — someone I had had to teach to use Facebook three times.  Needless to say, he was ill-equipped to buy a web company.

At that time I was Director of Content Marketing.  It fell to me to train my new boss and, for a while, he listened.  Sooner than later, he started pushing his own ideas through, as was his prerogative.  But I knew they weren’t right for that type of company or my employees.  I saw the writing on the wall, started designing websites on the side, and had a small portfolio ready the day I was laid off.

What I Did Right

There was a lot I did during the ‘building’ process that allowed me to launch my business the moment I needed to.  I took a few classes at a local entrepreneur organization and had an idea of what it took to run a for-profit business.  I started doing the work I planned to do way before I needed to, and had a legitimate portfolio ready when the time came.  With that portfolio and experience came a client list that I could lean on for referrals.

What I Did Wrong

I’ve had a lot of time to reflect on the things I wish I’d done.  There are days when the list is really long (bad days), but most of my mistakes were built on ignorance, not actual wrong-doing or inadequacy.  I didn’t know how to reach out to peers, how to find a mentor, and how to build systems for growth, to name a few.

The biggest mistake I made was starting a web company because that’s the industry I had been in for two years.  I more or less took the myriad of work that was involved during my time with my former employer and repackaged it to fit what I saw as the industry opportunity.

There was no passion involved.

I’m good at web design.  I enjoy working with clients to help support their endeavors.  My background in Anthropology makes developing a website that communicates well with the end user a breeze.  Being a visual thinker, design was a pleasant change from the cold math of SEO.

But it was a strategic move — not a passionate one.

Passion is what gets us out of bed in the morning.  It keeps our engines running when we’re exhausted.  The nonprofit sector sees this every day.  Despite having petit budgets, a bootstrapped team, and competitive resources, nonprofits find their staff working 40+ hours / week easily.  The board of my nonprofit was comprised of extremely busy people, but they all gladly made time for a cause they believed in.

Stop & Think

If you’re considering starting a business, stop and think for a moment.  Consider your WHY.  What draws you to entrepreneurship?  I’ve heard the following from many of my clients:

  • I had a bad boss and I never want to work for someone again.
  • I don’t want anyone to control my livelihood.
  • I’ve been doing it for years and know I could do it better.

These are all legitimate reasons, but if there is nothing further from this, you’re going to burn out.  There must be something more to it.  “I’ve been doing it for years — and it would be my dream job — but I know I can do it better.”  There’s a big difference, there.  Four years down the road, when you’re going through a dry spell or need to make a difficult transition, that difference will mean everything.

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