Friday is Why Day: first in a series.

Why I never wanted to work for myself:
“I need the benefits.”

Can’t tell you how many times I’ve heard this from people in the past month, citing why they have no options outside of full-time employment with another company. And each time I hear it, a little song plays in my head… I remember thinking that!

If you know me, I hesitate from presuming to understand someone else’s situation – so if you say, “I have to get a job because I need the benefits,” I’ll listen. But if you admit to an inkling of desire to work for yourself, I’ll offer why that same reason held me back for almost 18 years.

“I’ll never work for myself — I need the benefits.”

I used to say that, too. When I was single, childless, and shall we say, dewy with youth. Free-wheeling and roaming about the Twin Cities, going to the gym 6 days a week and living a healthy, blessedly health-problem-free life. (translation: insanely affordable coverage, compared to what I carry now.)

Fast forward to 2010. I’m married, with two mortgages, a family of 4, and a stay-at-home husband who cares for our children. In other words, I’m the breadwinner with a LOT of fiscal responsibilities on my shoulders. Including… our healthcare premium. (let’s take a break so I can laugh hysterically again in order to fend off the panic)

Taking that leap to work for myself was a pretty gigantic transition. But luckily, I DID have 17 years of agency experience and – I admit – some savings to help us manage the financial inconsistencies of starting a business.

If you’re reluctant to go out on your own because you “need the healthcare benefits” – I challenge you to look at the whole picture:

* Do you know what your health coverage would actually cost? Whatever it is, all of your health care costs plus the policy premium would be a business expense for your LLC.

* What other benefits do you think you’d miss out on? If you’re still in your 20s or 30s, and if you even have a small nest egg started, you’re not in dire straits (my opinion) if you miss a few years of that company-matched contribution – if you’re lucky enough to get one.

* So, your company did X for you – sent you to grad school or something else? Look at the whole picture of your life and consider whether it’s worth putting your dreams on hold. I can guarantee your boss isn’t sitting up at night thinking about your dreams.

“I’ll always work for an agency – I need the benefits!”

There’s nothing like a surprise pregnancy to make you was to run screaming for better health coverage. HA – just ask me about it!  Go back a few paragraphs and read that list of responsibilities again, I’ll wait.

Ok, now figure in a new baby – including a c-section, hospital stay – and an extremely high deductible because we didn’t account for another child in our original plan. My gut instinct was, “Holy crap, I have to get a job. I need the benefits!” But that didn’t last long.

In the first two years of working for myself, I learned where there’s a will, there’s a way. And I was Not. Going. To. Fail. Myself or My Family.

In the third year of working for myself, I learned how to dig deeper: because I had to. I learned how to manage self-employment and morning sickness. I learned how to manage client expectations, project deadlines, new business and pregnancy. Our little surprise became a great blessing. I barely took an official maternity leave because I already had such freedom and flexibility in my schedule. Rribbitz Bbaby even joined me at work, where we were warmly welcomed by the coolest of clients.

Don’t get me wrong, we’re still paying the hospital bills. And making payments on a new car. And breadwinning for a family of 5 makes things even more interesting these days. But the thing is – today, I know more than ever:

I love working for myself.
Because I absolutely love the benefits.

Friday is Why Day. So I’m asking: why are you waiting to do what you love – and are the barriers truly insurmountable? Consider the other benefits that could be awaiting you – after the leap.

Note from my 6-year old: "I love you. You are love. I'm your love. You are mine."



First in a series of “Friday is Why Day.” By yours truly: independent writer and consultant for creative, web, PR and social media content; with 20 years of ad agency experience. Hopelessly eternal optimist.

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