5 Good Reasons To Choose Freelancing Over Traditional Work

This is my love letter to the freelance lifestyle.

I’ve been working freelance for a long time now — for about twenty years in the field of publishing, and in more recent years as a freelance writer. I’ve been fortunate to live off of freelancing exclusively, but it also helps I’ve got a supportive wife who puts up with an awful lot.

Should you join the freelance workforce?

It’s not for everyone, sure, but I think it’s a better choice for more people than one might expect — especially if you work in a creative field or in one that requires you to be self-driven.

Here are five reasons that speak most to me about why you should consider going freelance. If you’re looking for the downsides, you can find plenty of pieces online about that.

Except for a quick nod to the challenges, this piece is all about the plusses.

Here we go.

You’re Less Subject To Someone Else For Employment

We’ve learned a lot about ourselves and the nature of work over the past year or so.

One thing we learned was that there are no guarantees when it comes to staying employed. Businesses laid off workers left and right during the pandemic with little in the way of warning.

Things got dire for a lot of people. If it wasn’t for government support, things would have been worse.

Even before the pandemic, “at-will” employment meant people could lose their jobs for almost any reason — or no reason at all.

That’s no way to live.

At least when you’re freelancing, you can’t fire yourself.

I’ve lost jobs simply because the owners wanted someone cheaper. In both cases, I had no warning. I came to work on a Friday morning (it’s always a Friday) and found myself filing for unemployment that afternoon.

The second time an abrupt layoff occurred, I decided it wasn’t worth subjecting myself to that kind of thing. I found some freelance clients (one of whom was livid that I was laid off and hired me for a regular monthly gig) and went full-time.

The guy I checked in with during my period of unemployment payments was surprised I was canceling before my benefits ran out. I explained I found my own work and didn’t need the payments any longer.

He’d never had anyone say that to him before. (I feel I should point out that had I continued to accept benefits, I’d have been committing fraud.)

The point is, going freelance meant becoming my own boss.

And I’m a pretty awesome boss. I would never lay myself off without warning.

More Creativity, More Productivity

Let’s talk about how working a 9-to-5 job can stifle creativity and productivity.

Not everyone is built to work that kind of schedule. Some people simply don’t perform at their best. At my last “traditional” job, I was good for the mornings, but by the afternoon, I’d just be going through the motions. I like to think that my super-productive mornings made up for my non-productive afternoons, but it still seemed like a waste of potential.

When I switched to freelancing full-time, I started early in the morning and just blazed through work until early afternoon. That’s when I’d switch to more mundane tasks like chores or sleep — things that didn’t require me to be at my best creatively or mentally.

Being free to make my own schedule meant I could capitalize on my natural rhythms. I became more productive at my peak hours, produced better work, and had greater success as a freelancer.

All I needed to do was get away from the oppressive, regimented routine of traditional work.

You have a Wider Pool of Colleagues

In a traditional job, you’re pretty much only interacting with the people who work with you — in the same office or department. You might interact with your counterparts in other offices, but it’s not likely.

Your colleagues are usually the three other guys in the office — and one of them is denser than a bag of rocks. The other two won’t shut the hell up about Patriots football.

A lot of people think being a freelancer means working in isolation. While there is some truth to that, the vital thing to remember is that freelancers can network and consult with others.

And those “others” are people spread all over the world.

I live in Rhode Island. My mentor is a woman in Texas. I coordinate projects with folks in Maryland and California. My favorite production manager is in Japan. My favorite editor is in Colorado. My freelancer online kaffeeklatch comprises folks from the US, Canada, Germany, and the UK.

I know a lot more interesting people these days.

I mean… nothing against my fellow Rhode Islanders, but there’s a big world out there, and being a freelancer means I’m a part of that bigger world.

Beat that with a stick.

No One Cares About Your Educational Background

I’ve yet to fill out an application asking for my educational background when taking on a freelance client. Perhaps someone looked me up on LinkedIn, but more likely, they looked at my portfolio and used that to determine I was the right person for their task.

No one cares about my undergraduate thesis on Anglo-Saxon poetry. It’s been over 30 years since I last sat in a classroom, and no one is interested in my academic achievements.

What mattered was whether or not I could put together their book, manage their journal publication, or write the copy they needed.

My experience mattered more than my education.

Lucky me. Despite a pretty stellar academic career, I never actually graduated. I ended up dropping out of my final semester for very personal reasons. By the time I was in a position to consider finishing and obtaining a degree, it turned out to be unnecessary. I had all the right experience instead.

I’ve received a good education, which has made me a more rounded person, but the lack of a college diploma has never been an issue in the freelance world.

If you’ve got the skills, that’s what matters.

No Commute, Fewer Expenses, Less Politics

Whether driving or taking public transportation, the commute was a pain in the ass. Snow, rain, blistering heat all made commuting a hassle. Having to get up earlier just to get to my job seemed like an immense waste of time.

That was time better spent on myself or on doing something I enjoyed doing more.

Speaking of spending, just to go to a job I hated, I had to buy a car, pay for insurance, pay for gas, and pay for maintenance and repairs. That’s money I could have spent on books and gourmet coffee.

These days, my commute is as far as from my bedroom to my home office, with a detour through the kitchen. It costs me nothing. I even save money by not having to own racks of business-casual attire. I have a couple of sets for the occasional meeting or conference, but I mainly work in jeans and a t-shirt.

Best yet, I don’t have to deal with office politics. I never really cared about who liked who and who hated who and why. Inter-office rivalries annoyed the hell out of me. I just wanted to do my job and get out of there.

Some people live for their job and thrive on drama.

Pass.

I don’t miss dealing with other people’s drama.

If you go freelance, you’ll find yourself not having to either.

Sure, Freelance Is Great, But…

But it’s not all tea and roses.

It’d be dishonest of me not to acknowledge, even briefly, some of the downsides:

• Taxes
• Paying own bills
• Covering own insurance
• Paying for own office equipment, supplies, and utilities
• Keeping up on billing and paperwork
• Hustling for your clients

It is all worth it.

Some downsides may be a challenge to get the hang of when you’re just starting out, but you’d be surprised how quickly you figure things out.

Be patient, be willing to learn, take action, and you’ll do fine.

And you’ll be a lot happier.

Is this a guarantee?

I wish, but I suppose some results will vary. If you find you thrive better in a traditional work structure, then, by all means, go for it.

But if you’ve been hesitating before going freelance because you’re worried it won’t make you happier, let me suggest that it will.

It’s at least worth a try.

I’ve been doing this for 25 years, and I’ve no regrets.

Cheers!

Thank you for reading. I’d love to share more with you via my Bi-Weekly Word Roundup newsletter sent to subscribers every other Sunday. It will feature news, productivity tips, life hacks, and links to top stories making the rounds on the Internet. You can unsubscribe at any time.