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By ☆ Published: October 9, 2017, 3:00 am

The Dark Side of Entrepreneurship

Entrepreneurs play by their own rules and are living the dream – and then reality sets in.

I love my job. As a freelance writer, I have the time and freedom to travel, exercise and pursue hobbies whenever and wherever I want. If I have to finish an assignment, I can do it just as easily from a hotel lobby in Bermuda as I can from my home office. It’s a gig that I wake up every morning grateful for.

But sometimes, it can be a real bitch.

Freelancing, for all its allure, is a risky and stress-inducing career path. It forces you to manage every aspect of your business – and face all the consequences for your mistakes. Working for yourself will make you appreciate aspects of an office job you never even thought of.

Basically, I’m trying to tell you that freelancing has a dark side.

It’s isolating.

As an extrovert, it’s not surprising that one of my favorite parts of my old job was chatting with coworkers. I loved gossiping about other people in the office, discussing the latest “Game of Thrones” episode, and fighting over the leftover bagels.

Now I work at home. The only other living creatures are my husband and two dogs – who are great company – but don’t offer the same opportunities for varied opinions and perspectives. I miss the camaraderie of the office and being part of a team. When I have a problem with an editor or want to complain about something I saw on Twitter, I don’t have other people to do it with.

My situation is even more frustrating because I moved to a new city at the same time I quit my job. I have friends here, but it’s not the same as seeing a consistent group every day. Making new friends is always hard, and even more challenging when you work at home all day.

In some ways, freelancing is the job that’s least compatible with my personality. I love being around people and still dream about the good ol’ days when I could vent to a coworker in person. Even though I love making my own decisions, I miss holiday office parties and big staff meetings.

It’s all on you.

When I had just graduated from college and was looking for a job, a friend asked me if I had considered becoming a freelance writer. I was trying to find a job in the magazine industry, which is as competitive and difficult as “The Devil Wears Prada” makes it out to be. Months after graduation, I was still unemployed.

I told her I didn’t want to freelance full-time. It’s too unstable, I said. I knew a few freelancers, and most of them were seasoned journalists who had written for Esquire or The New Yorker. I couldn’t even land a gig at my hometown newspaper.

It’s ironic that I became a freelancer when I spent so many years vehemently opposed to the idea. While I’ve gotten used to paying quarterly taxes, buying my own health insurance and working on vacation, I still don’t enjoy the instability.

Unless you have regular retainer clients, you have to drum up business every month. Most of the time, I land more than enough work to cover my bills, entertainment budget, and savings goals. I’ve also had several slow months, where I’ve had to dip into our emergency fund to cover the bills. Some days I feel rich – other days I feel jealous of my friends who still have regular 9-5 jobs.

It’s all-encompassing.

At my last “regular” job, I never had any problems leaving work at the office. I didn’t check my email on the weekends or during vacations, and I didn’t feel guilty for it. My job was not my life.

Now, my job makes up a bigger part of who I am and how I define myself. Since my personal email and my work email is the same, I often check it when I go to bed and when I wake up.

I’ve heard the same from others who have started their own business. I once read that being an entrepreneur means working 80 hours a week for yourself instead of working 40 hours for someone else. I’ve gotten used to this new mindset, but it’s not for everyone.

It’s unpredictable.

Even when I was working in the unstable field of journalism, I never worried about losing my job. If I got laid off, I could collect unemployment and move back home until I found something else.

Now I’m always in fear that my freelancing clients will dry up, that my luck will run out or that robots will learn to write articles better than me.

To combat my fear and anxiety, I save a lot for retirement, have a substantial emergency fund and remind myself to enjoy being self-employed. I can travel when I want to, take on work that I enjoy and get to see my friends and family more than I ever did before.

Are you an entrepreneur who has experienced the dark side? What are some other tough things that people overlook? We’d love to hear about it in the #Adulting Facebook community

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The Dark Side of Entrepreneurship was last modified: October 8th, 2017 by Zina Kumok

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