The Madness of the Entrepreneurial Mind

In Chronicles of a CEO by Rebecca Liston

Ever stop and ask yourself just what you were thinking when you made the decision to run your own company, to be an entrepreneur?

I mean, really, what kind of madness overtook your mind the moment you quit your full-time corporate job, or made the choice to leave college, or borrowed that $10K from your grandmother to strike out and have “a go” at building your own business?

I don’t use the term “madness” lightly here!

I actually think it is a certain kind of madness that prompts those of us who have “done it” to venture out on our own, to forge our own path, to go where “no (wo)man has gone before.”

What I call “madness” is somewhat related, I think, to what Steve Jobs referred to in his famous quote:

“Here’s to the crazy ones, the misfits, the rebels, the troublemakers, the round pegs in the square holes…the ones who see things differently… they push the human race forward, and while some may see them as the crazy ones, we see genius, because the ones who are crazy enough to think that they can change the world, are the ones who do.”

Because let’s face it: the one thing that each of us entrepreneurs has in common is the belief that somehow, some way, we can change the world.

That’s our own “special blend” of madness, I think! And it makes us, as Jobs says, “the crazy ones.”

Now I, myself, am pretty much okay with the fact that I am a “crazy one” but it took me some time to reach that place of acceptance.

I come from a long line of Employed People – and not just “employed” but “employed by the same company for pretty much their entire lives” sorts of people.

I love my family, and I appreciate who they are and the way that they function, but boy-oh-boy we are truly not the same in so many ways!

I remember when I tried to be an Employed Person. I had this defining moment when I had landed what would have then been seen as my “ideal job.” It was my first day, and as I stood in my office, looking about, assessing the view, contemplating the new drapes I would need, my colleague came into the room and said, “Isn’t this amazing? Here you are, 26 years old, you’ve landed your dream job, and you’ll be able to be here until the day you retire! Isn’t it great?”

She was so sincere…and was likely quite startled when I looked up at her with panic in my eyes. “Oh, dear God, NO!” I screamed in my head. “No, no, no, no, no!”

And that was the moment when I realized: I was not an Employed Person by nature. In fact, the very idea that I would have that job (that same, repetitive, job) day in and day out for another 39 years filled me with panic and dread.

Three months later I left that company and went back to school. My entrepreneurial journey had begun.

Now, let’s be honest, because it doesn’t just take a particular brand of madness to start one’s entrepreneurial journey. No, it also takes a certain amount of crazy to keep going despite all the odds.

In those moments when you’ve no idea how you’ll pay your mortgage, or when your clients don’t pay you, or when you’ve no clue how you’ll get your next customer through the door…those are also moments when madness prevails.

It’s still that same madness that Jobs refers to as the desire to change the world. But in this case, it comes with a post-script: “At any cost.”

In order to keep going on the entrepreneurial journey, you must at certain points accept that your desire to make a difference is far greater than your fear, far greater than your worries, far greater than your concerns. Your desire to make a difference, to change the world, becomes the only thing that matters.

And you go on.

Despite adversity. Despite fear. Despite the dwindling bank account.

You keep moving. You keep making calls. You stay in action.Because you know that the one thing you must do is keep going – you tread water to keep from drowning, so that one day, you can swim again.

I had a great call with serial entrepreneur and all-around cool guy Mitch Wilder last month and we found ourselves sharing War Stories about being in business. And I was telling him that I had recently been interviewed about what it was like to be an entrepreneur. One of the questions was: “What’s the number one quality you need to be successful in running your own business?”

“Tenacity!” Mitch and I shouted at the same moment!

We laughed then, and talked of how, like “dogs with bones,” an entrepreneur just simply has to have the tenacity to keep going. In looking back on that conversation, I think “tenacity” could just be another word for “madness!”

Obviously this is something that’s been on my mind for a while now…this notion of the madness that IS the entrepreneurial journey. Last year was one of the craziest rides of my life in terms of the business, and I’ve heard from many others  a similar story. My sense, however, is that 2015 was all about treading water, staying afloat, doing whatever it took to keep from drowning, and that 2016 will be all about swimming forward towards our goals swiftly, efficiently, and with renewed strength that comes from understanding that we can, indeed, do it.

We can make a difference, despite all the odds, because we are, each of us, just a wee bit crazy. And I, for one, wouldn’t want it any other way.

Big love,
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Rebecca Liston helps her clients predict, pivot, and compete in an increasingly complex global marketplace. Her clients quickly uncover the root of their challenges and know the actions to take to overcome them. A six-time nominee for the RBC Canadian Woman Entrepreneur Award, Rebecca combines business strategy with intuition, giving her clients the edge on forward-thinking, elegant answers to their most complicated problems. Her clients are entrepreneurs with CEO-mindsets and executives with entrepreneurial instincts. She is based in London, Ontario. What if you could get the answer to your biggest business challenge, in one sitting? Visit to find out more.