The Lonely Side of Freelancing

Freelancing can be downright lonely sometimes.

Wendy Parish
3 min readJun 7, 2018

I love freelancing. Most of the time it’s amazing. I have control of my career, my scheduling, and ultimately my life. But — as there is with everything — there are downsides to freelancing. If you’re thinking about taking the jump to freelancing or you are already there looking to identify with someone — I want to offer an honest portrait of freelancing.

Some of the things that make freelancing amazing can also be the culprit behind the negatives. Here are a few reasons the digital nomad, freelancing lifestyle can be lonely:

You are Physically Isolated

Freelancing means you can work from ANYWHERE. I love this! But it also means you are usually physically isolated from others for the majority of your time. I work from a home office and am completely alone for most of the day. Being alone is a great tool for productivity, while also being a recipe for loneliness if you are craving social interaction.

No One Shares Your Experience

When you work in a traditional office or any company with multiple employees, you are sharing a similar experience. You can meet up with those people at happy hour and bond over how shitty Cheryl in HR is.

When you’re a solo freelancer, your work experience is solely your own. No one else is ever really going to understand what it’s like to be in your job. You can vent to good friends, of course, but it’s not the same as the comradery of having people in the same crappy boat as you.

It’s Hard to Find Other People With Similar Freedom

Having a freelance business that I operate from my laptop means that I can pretty much do whatever I want and go wherever I want. So when an opportunity to do some cool shit presents itself — I can usually do it.

The negative part of this freedom is that most other people DON’T have it. For example, I recently went on a solo trip to Denver. This wasn’t initially supposed to be a solo trip. When my travel buddy backed out, I tried to find another person to tag along. No one I contacted could get out of their work responsibilities on short notice. I enjoyed my vacation, but there were lots of moments I wished I wasn’t alone.

If the tables had been turned and someone asked me to go to Colorado last minute — freelancing would allow me to do that.

Want to go to a concert in the middle of the week? Most people have to be at work early the next day. Want to take a Friday off to day-drink? Better plan in advance or you’ll be enjoying that patio margarita alone.

Ultimately, your freelancing freedom is a still limited to others’ traditional schedules. That means learning to enjoy doing things alone, coping with disappointment, or adjusting to others’ more traditional work schedules.

What are some lonely moments you’ve had in freelancing? Or just in general? Vent away. I’m listening.

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Wendy Parish
Wendy Parish

Written by Wendy Parish

Creator of words, music, and magic. Proponent of freelancing and freedom.

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