You might be an entrepreneur if . . .

Remember Jeff Foxworthy’s redneck bit?


My favorite: You might be a redneck if you’re too drunk to go fishing.

But seriously people.

Thanks to Jeff we all know how to gauge our redneckness, but what about those of us who want to figure out whether they “might be” an entrepreneur?  I meet with lots of new entrepreneurs and those thinking about making the leap. And this question is always front and center.

How do I know if I’m cut out to be an entrepreneur?

There’s been some debate about whether entrepreneurship is innate or can be taught.  I actually think it’s a bit of both. Rather than jump into that debate, I’m going to channel my inner Jeff Foxworthy (in a serious way) to help you figure out if you “might be” an entrepreneur.  Here goes.

You might be an entrepreneur if . . . 

You are restlessly curious about how the world works

When you work for an established organization, they train you. They teach you. You slowly discover the nuances of how the world actually works. And you slowly add the skills necessary to advance inside their world. Many find comfort in this track. But entrepreneurs don’t like this slow pace. They have a burning desire to look underneath the surface of things and into their core. Human nature, business models, evolving technology, company politics, you name it; they want to understand it and exploit it. And they are self-motivated to find the answers now rather than waiting for an expert or mentor to feed the answers to them. Are you restlessly curious about how the world works?  If so, you might be an entrepreneur.

You focus on what your contribution is actually worth

Because you understand how the world works, you also understand the true value of your contributions. I remember this lesson vividly from my Dad, who was always in business for himself. I remember asking him why he worked for himself and his answer was “why would I want someone else to make lots of money off of my efforts?” Do you think past your paycheck to what the organization is actual making from you?  If so, you might be an entrepreneur.

You hate gatekeepers & rules

The world is full of gatekeepers and their rules for passing the gates. We learn this at a very early age, when a coach picks us for the starting lineup or a teacher gives us a poor grade. And when you join the adult world, you find that big organizations are chock full of gatekeepers and rules. The size and complexity of their org’s require them. I faced the prospect of gatekeepers when I was considering joining a big law firm after school. I would need to impress the partners I worked for, and the compensation/leadership committee.  But I didn’t see this as a ladder—complete with mentors and a nice salary. Instead it appeared to me as a negative, as I envisioned working a ton of hours for someone else, toiling away, putting in my time, and kissing lots of golden rings to get ahead.  Do you grate against rules and the gatekeepers that enforce them?  If so, you might be an entrepreneur (and a coincidentally, a redneck).

You don’t suffer fools—or crappy work—easily

To an entrepreneur, mediocre work is a tiny slice of hell. And so is the thought of working shoulder to shoulder with folks doing crappy work. It’s like nails on a chalkboard. This drives many entrepreneurs out of larger organizations, which unfortunately have pockets of mediocrity in many places. Have a beer (or two) with anyone in a big organization and turn the conversation to work and I almost guarantee you’ll hear frustration with some inept person or department they must deal with on the job. Just yesterday, I listened to someone at a big firm complain about how it took his company’s procurement department a year to approve a new vendor that was critical to his efforts. I think he enjoys his work, and simply views this delay as part of life in a big company. Entrepreneurs have a really hard time dealing with this kind of stuff.  Do you like living in a world where the pressure of failure requires everyone to do excellent work or hit the road?  If so, you might be an entrepreneur.

You like to sell people

I’m not talking here about the classic sales person. What I mean is that entrepreneurs LOVE to influence people, convince people, inspire people to follow them and buy into their way of thinking. They draw energy from seeing someone’s body language turn positive in an investor meeting, an employee interview, or a prospective customer pitch. The best entrepreneurs are on a mission, and they love convincing others that that mission is an exciting one.  And it doesn’t matter whether they do this in person, in writing, or through a user interface. Do you get huge energy from changing hearts and minds?  If so, you might be an entrepreneur.

You look to work to create meaning in your life

An entrepreneur thinks about her work as a core part of who she is, and a big part of her life’s story and legacy. This doesn’t mean that you can’t have balance as an entrepreneur. I speak from experience in saying that balance is possible, especially with a co-founder. It simply means that entrepreneurs don’t seek out a “job” that pays the bills so that they can explore their true passions. Do you want your passions and your job to meld together as much as possible?  If so, you might be an entrepreneur.

You draw energy from risk

Everyone has a unique tolerance to risk, but entrepreneurs tend to draw energy and motivation from risk. They like being out there in a place where the risk of mistakes makes them sharp and where the rewards for doing great work are magnified.  Does risk and living on the edge excite you and motivate you to get up every morning?  If so, you might be an entrepreneur.

You hate the zoo

I remember this vividly when Microsoft bought our startup Brian Wiegand and I had been working post acquisition inside of Microsoft for a few months. The people were smart, the work was interesting and the earn-out pay was great (so great that I hate even thinking about it now). But I’d often get a blank stare on my face as I sat at work. It was the same look that I remembered seeing on zoo animals as they stared back at you from their cushy habitat enclosure.   Sure they were fed well, they had no predators, they got all their vaccinations, and they never got really scared or cold. They had fans shuffling by everyday reading the plaque outside their office. But there was something missing. Inside they knew at a subconscious level that they wanted to be out there in the wild doing their own thing, relying on their wits and skill. Staying sharp. And living out the life that they chose. And they were willing to risk death to get out there. I pitched this analogy to Brian and he agreed. And we both left the safety of Microsoft and went back out into the wild.

So there you have it. Is the wild calling you? Does the risk and reward of succeeding or failing on your own and with your own team of people call to you? I hope so, because the world needs more entrepreneurs.

I’ll leave you with one more thought. The zoo is an illusion. The industrial economy is transitioning to a new economy. The middle class is shrinking. The days of working at the same firm for your career and retiring with a nice pension are gone. As the zoo walls crumble, we see two types of people: creators that create value themselves and everyone else. So no matter where you are, you should think about yourself as an entrepreneur leading the unique startup that is you. Figure out how the world around you really works. Develop your own personal business model and unique value proposition. Invest in yourself and create a secret sauce that makes you valuable. At least in this way, we are all entrepreneurs now.

Hat tip to my friend Brian Wiegand, from whom I learned many of these lessons.

3 thoughts on “You might be an entrepreneur if . . .

    • Thanks Heidi! I’m glad you enjoyed the post. I know you’ve been in the startup trenches long enough to appreciate what makes an entrepreneur tick! I have a few book ideas I’ve kicked around but they are mostly half baked at this point. Hopefully blogging will help to crystalize some of them.

  1. Hey Mark, good write up! I think heading off cruising as a form of “lifestyle entrepreneurship”. It’s stepping outside of the bounds, or the zoo, of normal society, living for yourself, relying on yourself, and being accountable to yourself. Now that I’m back and working for others again I can barely stand to think about the value I hold and what they are getting so I’m looking into various avenues to output my talents. Have fun and be safe on your cruise!

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