Is health insurance calling? Weighing the pros and cons of an FTE role.

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“When are we going to start living the dream?” I asked a friend, who also owns her own business.

“Dude, this IS living the dream.”

We both sighed.

The freelance life is a hard row to hoe. Yes, we get to set our own schedule and choose our projects, but we also have to act as business manager and entrepreneur. We have to worry about stuff like quarterly taxes and covering our own health insurance. Last month, Regence Blue Shield sent out letters informing freelancers and sole proprietors across the state that they were eliminating their individual plans save for three counties. Premiums have steadily increased over the past few years, and my friend and I were already choosing “bronze” plans with less coverage and higher deductibles to get by each month. Now our options are further limited.

So it’s not surprising that we are contemplating giving up the freelance dream to return to full-time positions. In the current state of our nation, the benefits package that comes with a full-time position can trump the freelance life. That said, being your own boss is a glorious thing. Let’s weigh both options.

Consider the FTE

Health insurance: As I get older, health bennies sound like a perfectly sound reason for taking a job. When negotiating an FTE (full-time employee) role, ask for plan specifics, including vision and dental.

Retirement contribution: Does the employer offer a 401(k)? If so, what’s the max you can contribute and do they offer any matching funds? Is there a vesting period and do they offer any other financial incentives, such as stock options?

Consistency: I do love a regular paycheck and even appreciate a consistent schedule and workload. But I like variety as well. Ask what a regular workday and week look like, and what your core responsibilities would be. Is there room to veer out of your lane occasionally?

Collaboration: Working for yourself often means working in isolation. Do you work better when you fly solo or are you game for working in teams?

A freelance state of mind

Control: As a freelancer (or even a contractor), you are ultimately your own boss, for better or worse. Do you want to hold the reins or are you comfortable handing them over to someone else?

Variety: As a solo artist, you can develop a pu pu platter of projects that play to your strengths and interests.

Flexibility: You have the opportunity to take your work on the road, work from home or take lengthy vacations, in addition to setting your own office hours. Is that important to you?

Opportunity for greatness: With risk comes reward. Working as a freelancer can pay off financially and in other ways as well. It’s profoundly satisfying to develop or create your own successful new product or service. What do you want to shepherd to completion?

Jennifer Worick is a veteran freelancer/contractor, publishing consultant and New York Times bestselling author. Email her at