Career Paths

My career path, while slightly unusual (Disney–Department of Defense–NASA–Freelancing), is not the only one by a long stretch. Your path will likely be the result of a mix between your interests, skills, aspirations, and job market. The bottom line here is that there is no ONE or RIGHT path to achieving career success. Every path can have advantages and disadvantage.

100% Employee

Some individuals are happy to join someone else’s team because they prefer to have someone else handle things like paperwork, marketing, business planning, selecting healthcare plans, etc. That was me for most of my career, and I was pretty comfortable with it. The larger the company, the more things you can have done for you. You might have a family or significant other and require steady working hours, steady pay, and reliable benefits. All of those are legitimate concerns and needs. And you might prefer being part of a team than working on your own.

That’s not to say your career won’t change as an employee. You might shift industries. You might find yourself managing others and moving “up the pyramid” until eventually you become CEO. Don’t laugh: Michael Eisner, one of the most successful executives to ever run the Walt Disney Company, was an English major.

100% Freelance

You might know from an early age that you want to work on your own. You might have the confidence and gumption to go straight from school to the working world, finding and supporting individual customers without any intermediaries. Good for you! Mind you, depending on your customers, what they want, and what they pay, you might or might not have to hustle more often to find the next job and keep the money flowing. You might be willing to face those risks for the magical freedom of living by your own rules and setting your own schedule.


Some individuals are even more ambitious. They don’t just want to go off and start their own one-person business, they’re interested in starting whole companies with a few to hundreds of people ultimately reporting to them. This might require additional education or some experience as an employee in a large or small business before starting your own business. Or you could learn as you go along. However, the larger your organization grows, the more you need to get smart about the law, taxes, human resources, production, IT networks, and other facets of your business…that, or you need to learn to hire smart and trustworthy people who can handle those things for you.

Employee to Freelance

After 20+ years as someone else’s employee, I decided I was ready to take the leap into being self-employed. I enjoyed a little transition supporting a small business where I was the only communications person in a group of engineers and so had to learn more “entrepreneurial” skills to contribute to the operation. The best advantage to this path is that people I’d originally worked with or for as an employee knew my work and so were willing to hire me as a contractor. Corporate life can help you build your network, but as a solo entrepreneur you can put that network to work for you

Freelance to Employee

I know people who have taken the opposite path: after years of operating as an individual contributor, they shifted to being a full- or part-time employee. This can make sense if your freelance customer base has dried up, you’re looking for more regular hours and pay to spend time with your family, or you’re just tired of the pressure of looking for new customers. You might end up becoming an employee of one of your previous customers–again, your network and your previous work can open doors for you that might not have been available to you otherwise.

Making Your Own Path

There are other possibilities. You could end up shifting among all of the options above. As long as the path works for you, who’s to say whether it’s “right?”

About Bart Leahy

Freelance Technical Writer, Science Cheerleader Event & Membership Director, and an all-around nice guy. Here to help.
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