The Serial Entrepreneur’s Rash or How To Decide What Your Newest Venture Will Be (Part 1)

When I originally started my UX design consulting business in Silicon Valley over 8 years ago, the single biggest driver was the passion to create something of my own. In fact, it was the very same passion that led me to a career as a product designer. That passion outweighed any trepidation I had about not being successful (and believe me, I had more than enough of those annoying “trepidations” to stop me).

On one hand, I was totally thrilled to be running my own show, to be able to energetically put into action all the ideas I had harbored when creating and managing UX teams for other companies. On the other hand, I was scared silly of taking on a challenge in an area where I had little experience. After all, in the world of business creation aka enterpreneurship, I was an absolute beginner. But being a beginner also made me quite happy because, for the first time in my career, I felt that I was truly in charge of my own business destiny.

Or so I told myself in the bathroom mirror each morning when I dutifully recited those daily affirmations. “I’m good enough, I’m smart enough, and DOGGONE it – I’m an…an…an..[deep breath] I’m an entrepreneur!” Can you say entrepreneur, Sarah? I knew you could….

I also remember several well-intentioned mentors asking what my exit strategy was. Exit strategy? What exit strategy? What is this exit strategy thing and how did it pertain to me? In my experience, exit strategies were for tech startups, stunt pilots, and maybe white collar hedge fund criminals, not for brand-spanking-new UX design services businesses like mine. I was only just getting started, and the thought of an exit was so far in the future that it didn’t seem relevant to consider. While basking in the rosy glow of my new business venture, I couldn’t imagine myself doing anything else but building my services business.  

Fast forward several years. A little voice in my brain started telling me that I would be starting other new ventures.

After a few more years of navigating the wild and woolly roads of building and running my business (and absorbing all the learning and, ahem, character-building experiences that came with it), the little voice turned into a loud holler; it could no longer be ignored. I began asking myself the question I’d not contemplated when I started my business: “So, what is next for me?”

For as much as I’d learned running my first business, I’d developed what I call The Serial Entrepreneur’s Rash: I was itching and scratching and frankly longing to start a new venture. My time as a service provider had only whetted my appetite to design and build something of my own, a product that I could cultivate beyond a standard short-term consulting engagement.

And so I started imagining what my next business venture would be. As soon as I allowed myself to open up to it, new ideas flooded in.

Almost too many ideas, and they all seemed shiny and do-able, at least at first blush.  I was a kid in a proverbial candy shop of business venture ideas, and I could see myself being enthusiastic about all of them.

How to pick just one? Did I even have to pick just one? And if I did pick just one, what would I do with my current business, the one that was still technically not only my day job but another venture that needed regular care and feeding and business focus?

Finally, with the help of my business mentors, I took a long hard look at why I wasn’t moving forward past a point with any idea. It was then I realized that it wasn’t for lack of good ideas or due to the fact the I had too many choose from.

I was simply scared of being business beginner again, of starting over.

I resisted exiting the comfort zone of my current business. I worried about starting over at something that had no guarantees of success.

Clearly, I’d developed temporary amnesia about what it was like when I started my first business, about the heady combination of excitement and trepidation that comes from attempting to peer into the unknown with the possibility of success (or not).

Ultimately, the passion of creating something new has been greater than the sum of any worries. I picked an idea that resonated with me and ran with it.

But more on that in Part 2 ,so stay tuned for my next installment, “How to pick one idea to run with when a jillion of them all seem really, really good.”

One thought on “The Serial Entrepreneur’s Rash or How To Decide What Your Newest Venture Will Be (Part 1)

  1. Pingback: Just Breathe, It’s only the Holidays |

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out / Change )

Twitter picture

You are commenting using your Twitter account. Log Out / Change )

Facebook photo

You are commenting using your Facebook account. Log Out / Change )

Google+ photo

You are commenting using your Google+ account. Log Out / Change )

Connecting to %s