From Freelancing to Start Up

Much of what we lost while freelancing can largely be attributed to the short time we did it.   It takes time to build a business and 18 months just isn’t very long.  Sure, our venture started with rosy illusions of what would be.  We had reasonable goals based on the research we had done, but other people’s facts only take you so far.  Once we started applying them to our particular situation, we needed to tailor the facts to meet our particular needs.  Those needs didn’t really become apparent until about 18 months in and at 18 months, we went full time with The Start Up.

The Start Up was a client.  There were two guys (a just-finishing his Masters single guy set on being the next Fortune 500 CEO and a married father with a day job he didn’t want to quit designer) who came to us with a broken website.  It was a simple contract project.  Fix it and walk away, like most of our jobs.  Then they realized they needed more long term help.  Time to bring on a technology guy.

However, The Start Up was just in it’s infancy living on it’s original round of funding, no money to hire anyone.  Topher was offered investment in exchange for hours with the likelihood of full time work when the next round of funding occurred.  I said sure.  If that’s wanted he wanted to do with a few hours of his free time, then he should.  Nothing seemed like it would take away from our freelancing goals and, really, who get the kind of money they were looking for.

They did.  The funding came thru.  The CEO couldn’t imagine moving forward without bringing on Topher full time for a two year commitment as the CTO, a decision making partner.  Of course, they couldn’t pay us quite what we needed, but, hey, we were part of building something, earning our investment.  This is just part of the process.

Christmas 2011 was spent “discussing” which direction to go:  do we join The Start Up full time or do we break away and continue freelancing (which, of course, was starting to flourish).  “Discussing” works if you define it as a WWF match where three factors (wants, needs, and what direction is best for the family) fought it out with no possible way to determine a clear victor.  None of the answers were tangible.  Neither of us could see the future.  Add to the mix a current project we were behind on that could have been managed better (tho that might have only been visible with hindsight) and the stress level was high.

I voted no.  I wanted to be our own boss.  I wanted to continue to grow our freelancing business.  I wanted to stay as far away from the corporate world as we could possibly get and I saw the signs for what life under the CEO was going to be.  I’d already been there for about 6 months and I didn’t like it.  I wanted a lot, but like most situations when dealing with what’s best for everyone, what one person wants can only matter so much.

Instead we focused on what was best for the future.  Were we willing to suffer some pain to build a better tomorrow?  Was it worth making more sacrifices now to provide more opportunities in the future?

(Are you missing the pain, the bleakness, I promised?  Stick with me.  It’s all so much uglier from here.)



1 Comment

  1. Working for yourself is not easy. It scares me every single day. I’m looking forward to the rest of this story, and the lessons it reveals. Thanks for your bravery in documenting your own path, Cate.

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