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Geometric Pattern

An entrepreneurial litmus test for risk-averse control freaks

February 02, 2018

Or, the scaredy cat’s guide to starting your own business.

This is not a post for the wild ones, the rebels or the free spirits. Instead, this one goes out to the nerds, the planners and the ones who play it safe. I am here to tell you that you, my friends, my people, just might be able to strike out on your own. Here’s one safety-first account of how it could happen…

My dad didn’t dole out much career advice, but the lessons he imparted were legit. First, he aptly pointed out that you spend more time at work than anywhere else, so you’d better do what I love.

Good advice! I followed it from day one.

The owner of his own law firm, he had worked for himself from the age of 30. So it’s no surprise he also advocated for the entrepreneurial life. In fact, I can still hear him saying,

“Trust me, Kate…you want to be your own boss.”

It was one of those life lessons he repeated constantly to make sure it sunk in. And it turned out, he was right…but I didn’t fully comprehend his message for the first decade or so of my career.

Then, I had a kid.

La vida post-baby, I craved flexibility, freedom and ownership for the first time. I wanted to leave my mark, make my own money and never be bound to a desk.

But with all that freedom comes a healthy dose of risk, and as a new mom I wasn’t sure I could shoulder it. So here’s a little test I drew up to gauge my readiness to eschew working for the man and start my own business. If it helps nudge one scared, would-be entrepreneur toward happiness, my work here is done.

1. Audit your past work happiness.

Once I decided it was time to make a move from my old position, I looked back on each job I’d had for the last ten years and tried to remember what about them I loved, and what about them I hated. It looked something like this:

9 to 5 or flexible? Big company or small shop? In-house or consultant? Team or solo?

Think back. If the words autonomy, flexibility and freedom set off neon lights in the happiness quadrant of your brain, maybe consider going solo. And even if you prefer to work in teams, entrepreneurship might be for you — ya just gotta find the right team.

In my own audit, I netted out as a team-oriented worker with a severe aversion to bureaucracy, who prioritizes the flexibility to work when and how I want over the stability and salary of a job with the big guys.

This helped me realize working from home alone was not an option, and partnership was something to explore. But I also knew I’d need partners with the shared goal of creating something small and mighty, not looking to build an empire. (←THIS IS IMPORTANT)

2. Determine your risk tolerance.

You know that thing when you’re starting your 401K at a new job and they ask you questions to determine how risk averse you are? If you’re someone who keeps their savings in shoe boxes under their bed, the small biz life may not be for you.

But if you can accept some calculated risk for ultimate gain, you have options. Can you squirrel up enough savings to float you if the whole thing goes awry? And do you feel pretty confident you could get another job in a few month’s time if you had to? If yes, maybe there’s not as much risk as you think.

(You might say the mere mention of these thoughts assumes failure, and ultimately impedes success…but if you think that, you’re not one of my people. We, the people, who assume that literally everything that can go wrong will, choose instead to take surprise and delight when something in this life goes right. It’s not pessimism, but a rare breed of realism that allows you to see the beauty of the universes’ many gifts.)

All this leads me to the next step…

3. Test the market.

Remember that no one human being determines your value as an employee: the market does. (And there you have it, I buried the lede.) Before you decide to go solo, get your name and your resume out there. If the market responds like a pack of hungry wolves, um, you might be onto something. And you can be pretty sure that with your current skill set, plus the experience of starting your own business, you’ll only be more desirable if you want or need to shill for the establishment someday in the future.

All this sounds great, you say, but I don’t even know where to start! Well, in closing, I believe it was Mark Twain, or perhaps Biggie Smalls who said, never let school get in the way of your education. Don’t let a lack of formal business education stop you, that’s why you have the internet! Get thee to the google machine, post haste.

And hey, if it all goes sour, at least you’ve got those shoeboxes of cash under your bed to fall back on.