Founder Focus
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Founder Focus

Starting is Not a One-Time Decision

On recognizing and coming to terms with the never-ending process

People say starting is the hardest part of any new venture. What they don’t tell you is that you’ll have to face the “starting” hurdle countless times, and the gumption that helped you get past the first hurdle will be long gone by the 97th hurdle. Every entrepreneur I know — regardless of education, experience, or past success — has to embrace the endless cycle of starting; myself included. Realizing you have to get used to starting over and over again is half the battle; the other half is finding what drives you to keep doing it.

I was fortunate. The first starting hurdle I faced was not exactly by choice. I didn’t have to build up the guts to walk away from a steady paycheck with benefits. I was thrown off course due to unexpected circumstances, and had no choice but to figure something out. It wasn’t until I looked back a few months later that I appreciated the value of getting catapulted off of the safe route. I had been moseying along with the crowd, uninspired by the traditional law firm ladder and stuck waiting for it to eventually get better.

It’s no small feat to take the first step towards starting something completely new, but on the other side of that first step is an optimistic freedom that energizes you…at least in the beginning.

Rinse and Repeat

Not long after John Fallone and I decided that we were going to start our own firm (and do it our way), it occurred to me that I wasn’t going to make meaningful progress until I came to terms with the process of starting over and over again. I had always been able to pick up on unfamiliar tasks quickly — that is, until that magical power didn’t transfer to the new venture like I had expected it to. “Where do I start” was not a question I had encountered much before, and it was nowhere near the vicinity of my comfort zone.

I’ve probably asked John, myself, and Google where to start on a given project at least 3,000 times in the past 10 months. And if you’re waiting for me to say it’s gotten easier after I had to figure out how to start something new the 2,467th time, well, don’t hold your breath. When you’re starting a business, you can’t just start with the things you’re already good at and expect the rest to follow. You have to start everything: build a website, SEO, marketing, social media (non-pro tip: it’s not for amateurs), client development, client engagement, administrative tasks that you used to have an assistant for, integrating these platforms with those platforms and using them correctly, and the list grows on a daily basis. Starting sucks as much the 2,468th time as it did the 2nd time; but, the sooner you accept that it’s an endless cycle, the sooner you can identify your reasons to keep starting.

This is where it gets better…

Find your “even so”

Starting new and unfamiliar work on a daily basis is humbling and difficult. It’s not for everyone, and it may sink your battleship if you don’t have a driving reason (or two) to anchor your perspective. On hard days when you feel like you’re starting everything and finishing nothing and getting nowhere, try thinking of some reasons that the hard days of what you’re doing now are still better than the predictable days of what you used to be doing. I like to think of them as “even so” reminders, because these reasons are not necessarily going to be the same as the reasons you started in the first place (aka your “why”). Here are a few of mine:

Even so, I’d rather be working directly with clients who are building amazing companies than spending my days reviewing documents for clients I won’t meet for years.

Even so, I wouldn’t trade my business partner and his enormous (and sometimes daunting) ideas for a predictable 9–5 gig with a steady salary anywhere.

Even so, I’d rather be part of a community of badass entrepreneurs who are fun to work around and eager to share valuable insight from the lessons they are learning along the way.

Even so, the safe route isn’t going anywhere if we end up failing miserably.

A few “even so” reminders can go a long way to help you start something new and unfamiliar again today, and the next day, and the next day. I haven’t been doing this long enough to know if the starting process ever feels comfortable. I’m inclined to think it probably won’t. Even so, you should keep starting.




Insights for founders and entrepreneurs from lawyers who can relate.

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Katelin Kennedy

Katelin Kennedy

Startup Attorney & Co-Founder.

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