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The Road Less Traveled

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Nobody ever said living the freelance and/or small biz start-up life was easy.  And they definitely didn’t say it during the getting-it-off-the-ground phase.  In the beginning, your emotions run rampant – nervous, excited, optimistic, anxious, scared shitless.  Your laser focus is on acquiring that first client, your flagship partner that will help launch a hundred other clients on the way to your ultimate goal of industry dominance and financial independence.  Mix all that together and you get a recipe for potential questionable decision making.

My first client was a close friend who owned a very successful personal training operation.  Like many small business owners, he had a strong desire to grow the business but didn’t have the time, budget or marketing savvy to get the process moving forward.  That’s where I came in.  Knowing I desperately wanted that first chance, that initial shot at executing the plan I had worked for months to develop, I dove in head first.

Things started off swimmingly at first – we developed a social media strategy, instituted an aggressive partnership program with other local small businesses, even discussed expanding his activity to weekend long boot camps.  I was so wrapped up in the excitement of actually doing the work I had thought about for years – “Hell, maybe my business can be successful after all!  What was I so worried about anyway?!” – that I now realize I had those entrepreneurial blinders on.  Being so caught up in the action, I never once stepped back and asked myself, “Is this the right client for you?”.

You see, my dear friend came with some baggage, to put it mildly.  Great kid, super knowledgeable in his industry’s finer points.  But there were some mental and emotional issues there, of which I had known about since we were children.  Looking back, I knew deep down that our success together would be limited by these challenges.  But, at the time, my enthusiasm towards my newly birthed career trumped any notion of logic or deserved skepticism.

It wasn’t until a few months in, when my girlfriend met my friend and first client, that my tunnel vision began to fade.  He was having a particularly difficult day and after spending a little time with him, she privately asked me how I felt about his behavior.  I told her my concerns along with my sense of loyalty to him as a close friend…and a friend in perpetual need, at that.  Understanding my emotional connection to him, she very softly wondered, all things considered, if I thought it was wise to link my yet-to-be-forged brand to his.

It was not the type of decision I had anticipated making with my first client.  We had already experienced success as a team and had several projects (and accompanying fees) in the hopper.  Yet here I was, giving serious contemplation to essentially firing my first and only client.  All on speculation that he just wans’t fit to be in business and would eventually do himself and me harm.

Fast forward to the present.  I write this post today with a healthy roster of clients whom I absolutely adore and who offer me opportunities and endearing trust I would have never dreamed of.  You already know how the story played out with my troubled friend – I left, we remained compadres, he eventually folded the business under mental fatigue.  And to this day, I am very proud of myself for making an extremely difficult – yet necessary – decision that could have devastated my business had I gone the other way.

There are countless moments like these encountered by entrepreneurs everywhere.  And I truly believe that it is in those exact moments where we make the choices that eventually form the foundation of who we are and what we’re all about.



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Growth obsessed startup co-founder (MusicBox) and strategist-for-hire.

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