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I thought freelancing was too scary until I changed my perspective


In 2015 I wanted to be a writer, but professionally, I was not there yet. The problem was not that I didn’t have any editor contacts, or that I had never taken an internship at a magazine, or that I hadn’t accumulated enough bylines. The problem was this: I still thought of myself as an employee.

Dreaming of the day I could freelance full-time, I started teaching elementary school so I could have my summers off to build my side hustle. On the surface, this made pretty good financial sense. We all need to pay our bills, and teaching seemed like a good way to work a job that was fulfilling while working towards my creative dreams on the side.

However, after three years in the classroom, I began to wonder why I wasn’t building the kind of freelance income I desired. It wasn’t until I negotiated my highest salary at my last teaching job when I had my lightbulb moment.

I’d been afraid of freelancing, when I already had the skills I needed

Three years of teaching at independent schools taught me that many “salaried” private school teachers operate on 10-month contracts.

But at my last teaching job, there was an added layer: The school where I’d accepted an offer to work did not offer benefits, at least any that made sense for me.

The health insurance co-op they belonged to folded two months into the school year, and I was on my own to enroll in insurance through the Maryland marketplace. I shopped around and found a plan for $340 a month, which was less than what my employer’s co-op rate had been, anyway! I took advantage of the school’s group rates for life insurance (which was very affordable because of my young age), but it was up to me to pay for it entirely out-of-pocket.

Last, the retirement matching program did not begin until six months into my tenure — or over halfway through my contract for the year.

I accepted the offer anyway, proud of myself for at least negotiating my highest salary to date. But soon, I was paying for all my expenses on my own. Worse, when I calculated what my salary would be in a few years with a 1% to 3% annual raise, it just did not seem feasible for the lifestyle I wanted to live. There was little earning potential and nothing but increased expenses on the horizon.

Towards the end of the school year, I was driving to work and agonizing about what to do. Suddenly, it hit me: When I had negotiated my “salary” at the time I had accepted their offer, it was no different than if I had been an independent contractor. I had agreed to give my time, talents, and skills to my employer for a period of ten months. And since my school wasn’t offering a single benefit in return other than a paycheck, I realized: I had been secretly self-employed the whole year.

I realized that being stuck in the employee mindset had caused me to associate freelancing with fear. I was afraid to negotiate my rates, afraid to pitch for ambitious work, and afraid of being rejected.

But when I realized that by negotiating my “salary” at a job with no benefits, then finding a way to cover all of my own expenses, I had been basically freelancing the whole time. I had learned the hard way, but once I did I realized I had what it takes to become truly self-employed. Logistically, I was already there. The only thing that needed to shift was my mindset.

I was working harder instead of smarter

The employee mindset gives the illusion that the stability we gain from a regular paycheck compensates us appropriately for our commitment. But in reality, employees tend to work longer hours, spend more time at work functions whether they want to be there or not, and are generally less in control of their own earning potential.

This is fine if you are at a company you love and you are making a good salary with benefits that work for your lifestyle. But in my case, I was still of the belief that working harder was more important than working smarter, and I was building a career around a financial situation that was just not giving me the true emotional security I needed — only a modest, consistent paycheck.

Employees often try to prove our worth by demonstrating how hard we work. But when I switched over to the freelancer mindset, I already knew my worth. Even while I continued to take salaried positions, the way I approached them changed entirely. And since that insight, my side hustle income has steadily increased.

I haven’t completely left salaried work behind — yet. I work remotely with a flexible schedule for a literary writers’ association that nourishes my love and knowledge of the creative writing field and allows me the flexibility I need to continue building my freelance work.

One day I will transition to freelance full time, but in the meantime I enjoy planning the largest creative writing conference in the US, learning about the field from best selling authors, and serving an organization with important cultural significance. I choose to have a day job that appeals to my creative interests, provides me the flexibility to manage my own schedule, and provides me opportunities to meet other inspiring writers as I learn. Much better than being in a classroom with few benefits and even fewer options!

Now, I look at my income as a simple comparison: resources invested versus resources earned. If the income from a project does not satisfy my needs and leaves me feeling emotionally drained, I hold out for higher-paying work. But if I feel jazzed about a project and want to do it regardless of income, I do. I know exactly how to cover my expenses on my terms, and before I agree to anything, I weigh in on whether the project makes financial sense.

The best part? The choice is always up to me.



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