Opinion – Joining the Ranks of the Self-Employed: My Three Simple Rules

The post-COVID aftershocks are many. But a most interesting one to me is the trend towards self-employment. A recent survey conducted by Intuit reported that 28 percent of U.S. workers are self-employed and growing. Since I’ve been self-employed for 21 years, it’s a good time to share lessons learned.

I still remember the day I made my decision. I had been caught in a horrendous traffic jam on my way home. Then-President Bill Clinton was in town and his motorcade made me a full hour late in picking up my children. I viewed the moment as a sign from God that the time had come. The next day I gave notice and have never looked back.

While I never looked back, I also couldn’t see what awaited. The roller coaster ride is not for the meek, but three simple rules anchored me.

Rule #1: Maintain an elastic ego. Our ego needs to be big enough to continuously extend ourselves to the point of vulnerability and small enough to manage our pride.

The need for an elastic ego can be as simple as considering projects that come your way. Projects can feel bigger than your skillset or so rudimentary as to be insulting. If they are a stretch, find your courage and vote on yourself. If you’re about to eat humble pie, recast the work as a way to build relationships and excel.

A pliable ego is also needed when the occasional but inevitable chorus is heard of, “The time is not right,” or “The budget isn’t there,” or “We need to evaluate options.” It is difficult not to take these words as an “assault,” and yet you shouldn’t. That is why my playlist starts with “The Boxer” and ends with Lady Gaga’s “The Edge of Glory.” I find my mojo, assert my value, and move on.

Rule #2: Attitude is everything. It does little good to be Chicken Little who perpetually sees the sky as falling. I have remained self-employed because I believe that “positive” will win out, and irritants and setbacks are just that. Nothing more.

Implicit in this rule is recognizing that we manage our own attitude. We need to hold ourselves accountable as the boss of us. That is why I carry a figurative pompom and boot in each hand—the pompom to cheer me on and the boot to give me a kick in the pants when I think I’m slacking off.
From accountability flows positivity. As the legendary coach Vince Lombardi once said, “Sooner or later, the man who wins is the man who thinks he can.”

Rule #3: Sell, deliver, rinse and repeat. Here is a typical conversation when someone asks me about self-employment.

Them: Do you enjoy going solo?

Me: Yes.

Them: Do you have any tips?

Me: Many. First though, do you like to sell?

Selling is my starting point as the be-all, end-all of successfully running a solo business because it’s what gives us the opportunity to deliver our goods. I didn’t realize this at the start and would only have described myself as curious, people-centric, and hard working.

There was a dark moment when I tired of selling and approached a trusted colleague who was a successful executive recruiter. I thought it was time to close up shop and be thankful for my long run.

After fielding many questions, I received John’s wisdom.

“Jill, you are tired, which is inevitable when we sell, sell, sell. But for as long as I’ve known you, you’ve been able to sell your ideas and sell yourself.  Take a break. Recharge your batteries. Then get back on the horse and start selling. That’s where you’ll be happiest.”

So what did I do?

I played tennis. I wrote. I walked a dog. I baked and baked and baked until my family said, “No more.” And then I got back on the horse and landed some work.

The good news is that after you do the rinse-repeat of “sell and deliver,” it becomes easier because delivery is the best sales tool ever.

Deciding to work for yourself is a big decision, and the challenges experienced along the way can be daunting. But I believe Walt Disney had it right. His motto was: “Dream, Believe, Dare. Do.”

Simple to say, harder to do, but not bigger than us—especially with three simple rules.

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