The Serial Entrepreneur's Dilemma: How To Decide What Your Newest Venture Will Be

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Postponing your newest venture? See how this founder chose a direction, broke through her comfort zone  and got started. 

By Sarah Kling (Founder, TattyTat)

When I originally started my UX design consulting business, 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 enough trepidations to stop me).

On one hand, I was 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, I was an absolute beginner, but being a beginner made me quite happy because I was in charge of my own business destiny.

I also remember several well-intentioned mentors asking what my exit strategy was. Exit strategy? What exit strategy? 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 glow of my new business venture, I couldn't imagine myself doing anything else but building my services business.

Starting My Next Venture

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 windy roads of building and running my business (and absorbing all the learning and 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 was itching and 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.

Where to Start?

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.

I was as surprised as anyone at my choice. Of all the great ideas I had examined and rejected, the one I selected was something I'd never even imagined: custom temporary tattoos.

From Ideas to Reality

In a sea of many creative ventures, the custom tattoo idea popped up as the result of inspiration that came from one of my consulting projects. And I love it because it combines design and creativity with a monetizable m-commerce business.

And so TattyTat has come to be my next venture --  it's a mobile app that lets users design and buy personalized custom temporary tattoos from a mobile device for any event or occasion.

And once I decided to run with TattyTat, the new venture just all seemed to come together seamlessly -- I found a fantastic partner to share my enthusiasm for making TattyTat a reality and a talented team to assist in developing and delivering it. Even better, I leveraged my existing UX design business and team to help support the early costs of starting TattyTat.

As a way of funding this new venture, we've opted to go the crowdsourced-funding path to jumpstart the creation of TattyTat and to build excited around this for a larger audience. We were also fortunate enough to leverage a new crowdsourced platform created to support women founders - Moola Hoop. So not only do I get to launch my own new venture, but in doing so, I support other women launching theirs as well.

As for my current business - it's still alive and well on its own and feeding my new ventures. So being a [repeat] business beginner has it's perks. And while I have no idea whether this will be successful, I'm back in the place of being thrilled (and a little scared) while doing it.

And I know I'll do it again. And again.

What's keeping you from starting your newest business venture?

SarahAbout the guest blogger: With 14 years of experience designing software systems, web applications, mobile apps, and websites, Sarah is an authority on designing and delivering the perfect product user experience. Prior to founding UEVision and TattyTat, Sarah served as user experience consultant, usability evangelist, and user experience team leader for a number of companies.