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What I’ve Learned about Freelancing and Fear (And Why I Have the Movie Sideways to Thank)

Last summer, I came back from a trip abroad and knew I wanted to make some changes in my life. There were so many big and small things that had gotten me here, but perhaps my favorite and the stupidest is that I had recently watched the movie Sideways and, rather than finding this story about adults confronting disappointment as they approach middle age hilarious, as I did when I first saw it at age 21, I found it too real. Of course, disappointment in growing up is inevitable to some extent, but the palpable sense that I could be sowing the seeds of my own disappointment, as the characters of Miles and Jack so poignantly have, weighed on me.

One of the first changes I knew I needed to make was professional. For years I had had this image of my head as life as a freelance writer, but I had always felt limited from making that leap by a few things: fear of getting business, fear of losing benefits (especially health insurance and paid vacation), and fear of being alone all day. These are three very legitimate fears, maybe the biggest for anyone thinking of going freelance. Although they are important factors in considering whether you want to freelance, they shouldn’t be limiting factors. Here are a few insights from my short time as a freelancer that have helped moderate these fears:

Fear: I won’t get enough business.

Insight: Planning, using your experience, and building up good relationships is a way to get initial business.

What always scared me about freelancing was the idea of having to start from square one. But if you have worked for enough years in a field or industry and have a good reputation, it’s likely you already have options. In my case, I was able to start by working on a big freelance web project for my former employer. If you can take the route of making an employer a future client, I’d recommend it. For all of the transitions you’ll be making as a freelancer—in how you manage your time and finances—it’s nice to be able to work on something you already understand. (Except if you hate where you work, in which case, get out of there if you can!).

Also, one thing to think seriously about if you’re unhappy in your job but feel you need the salary is whether you can change your spending habits. There are so many people who have left a demanding full-time job  and found it worthwhile despite the finances (see for instance the Minimalists, this man, this woman, this guy and the commenters on his article, a former Microsoft employee, you get the idea.). Admittedly, the economic realities of living in many big cities and suburban areas and raising a family don't always make this an option.

Fear: Losing benefits

Insight: It is a tradeoff. The health insurance situation is bleak, but so are many full-time jobs.

The lack of affordability, inefficiency, and inequality of the American healthcare system makes me sad and angry whenever I think about it. I’m paying about 10 times more to be a part of this system about which I'm deeply ambivalent than I was as an employee. (I’m purchasing COBRA, which ultimately was about as cost-effective as buying on New York State’s exchange). Basically it is a tradeoff: despite how bad my health insurance options are (and they are bad), at least so far it is worth it because my quality of life has improved. In the long term I plan to make some more changes to deal with this issue which I'll get into in future writing. As this guy says, flexibility is intoxicating. True that!

Fear: Being alone

Insight: Being alone and being isolated are not necessarily the same thing—especially at work.

I used to think if I was alone all day, I’d feel isolated, forgotten, lack social connections, etc. But I realized at my most recent job, which had many benefits, I often felt isolated. I was the only communications person at my level in the department, and this started to wear on me. I genuinely liked most of the people there, but I wanted more professional camaraderie. How does this desire translate to freelancing, of all things? Well, since I became a freelancer, I have made more time to talk to other writers; work directly with other writers, editors, and communications professionals; spend more time reading professional development resources; and even plan to attend a travel writing conference in May. So even though most of my days are spent on my own (which I don’t mind as much as I thought, as long as I get out of my apartment), I am making more of an effort to connect professionally. I am also more motivated to hang out with friends who I wasn’t seeing as much in my full-time job. And I'm not going to lie: I love wearing sweatpants.

I don’t want to whitewash this.

I don’t want to whitewash this experience. There are plenty of tradeoffs—the lack of benefits and work uncertainty being the greatest. I am definitely making less thus far, which is not easy in a city as expensive as Brooklyn. I am a skeptic by nature, which is why, despite all of the blogs I was reading with titles like “I quit my corporate job and live on an island, and life is beautiful,” I was doubtful.

But there is a reason that many people choose to go become freelancers, and it's not just because life is amazing on this side. I think it says something larger about the experience of being an employee in America today. (This Gallup article does a good job explaining it). To make matters worse, pay has stagnated or barely inched up for most people, and if anything, all of this will get worse under Trump. There are genuine positives. For me, I feel a sense of purpose I didn't have as an employee. I am now making more effort to learn about my industry, and I have a ton to learn.

A lot of it is unpredictable, but then again, so is everything right now. Hey, the bright side of a world in which our president may get us into a nuclear war with North Korea is that it’s a good time to take risks.

I’d love to hear from you.

Fellow freelancers and other independent workers, people who are thinking of freelancing, or people who have full-time jobs, I'd love to hear your thoughts about freelancing, how to make changes like this, and what it’s like to work in America today (it’s awesome, right?). Comment here--or on Facebook if you must.