Is a Freelancing Career Right For You?

Five ways to determine if freelancing is the best path.

A couple of years ago, Forbes projected that by the year 2027, just over half of all U.S. workers will be freelance. That report did not consider the current pandemic that has forced so many people to realign their work and career paths. I wouldn’t be surprised if that figure comes much sooner than 2027.

The freelance lifestyle has a lot of appeal for people, although many aren’t prepared for the realities of working for oneself.

To determine if freelancing is the best path for you now or in the future, consider these five questions.

Is the flexibility of freelancing a big draw for you?

Some people are drawn to freelancing by the relative freedoms offered. You get to pick your own hours, how long you’ll work at a stretch, where you’ll work, and what you’ll be working on.

Mind you, it’s best to make all of these choices based on what’s going to be profitable for you, but you’re also not bound by the seeming arbitrariness of traditional work hours and settings.

It’s more than just being a night person and choosing to work at night or someone who prefers to sleep late and start their workday at noon. More, it’s quickly adjusting your desired work hours to fit what’s going on in your life.

For years, I worked from the afternoon to the early evening. After we had our son, I shifted my hours to more late-night to the early morning because that’s what best fit our new family’s schedule.

As our boy got older, I could then readjust as needed. That kind of flexibility is gold and not something you’re going to find at most 9-to-5 jobs.

Do you do your best work when working alone?

One of the biggest adjustments new freelancers have to come to terms with is getting used to working mostly by oneself. This may vary depending on the sort of work you do, but most freelancers are coming from an environment with multiple employees to one in which it’s just them alone.

For most freelancers, this is a welcome relief. We get to control the noise levels. We get to control the distractions. Uninterrupted alone time is a great way to maintain focus and be more productive.

Seriously, I got work done two-to-three times as fast working home alone than I did in an office with the seemingly endless barrage of chattering coworkers, phone calls, and other interruptions.

For some, solitude may be a distraction.

That’s fine.

Play some radio in the background. Or some music. Maybe turn on a TV in another room just for a little bit of background noise. Do whatever you feel you must to get used to working in a more quiet environment.

But if you already start out being more productive working alone, you’re probably on the right track.

Can you maintain self-motivation and self-discipline?

With a traditional job, you drag yourself out of bed, shower, eat breakfast, and trudge to work.

Can you get up each day, shower, eat, and shuffle to your home office with the same regularity?

It’s an important question.

Some of the work you’ll be doing will be wonderfully creative and engaging. Some work will be dull and tedious. You need to get the dull and monotonous work done with the same discipline you’d apply to more “fun” work.

I’ve worked in printing and publishing for over 25 years. Most of the time, the work is engaging and allows me to flex my creative muscles. Other times, though, it’s painfully tedious. Imagine placing over 500 photos and captions into a book layout that has to meet a specific deadline.

It’s tough.

Even writing can get tedious at times. I get to write about some interesting topics as a freelance writer. I also find myself sometimes writing about boring topics.

But bills have to be paid, you know?

So to be a successful freelancer, you absolutely must have a strong send of discipline and motivation — even when the work at the moment is less than inspiring.

It’s not a skill you’re expected to have acquired overnight, but it’s one you need to develop if you want to have a working freelance career.

Can you manage your own schedule?

Managing your time is more than just practicing self-discipline and being motivated to work. You also need to manage your work schedule.

It’s surprisingly easy to overpromise on jobs and get overbooked. That puts you behind schedule, and that means deadlines get missed.

Deadlines can’t be missed.

Figure out reasonable estimates for how long specific tasks will take you and what amount of time you reliably have available. Include time for managing your freelance business, self-care, and… y’know… sleep.

You’re the boss now. You’ve no supervisor besides yourself.

You make the schedule, but you also have to keep to the schedule.

If you can manage that, you have a great shot at a successful freelance career.

Can you be a good and consistent communicator?

Any kind of business relies on good communication. That could be between you and your clients, or you and any vendors you use.

It’s no different in the freelance world.

When a client or potential client emails you with a question or request for a quote, don’t let it sit unanswered for too long. In fact, the sooner you get back, the better. It projects not only professionalism but also a commitment to your work for them. This applies to phone calls and text messages as well.

Good communications make clients feel more confident in you and that their projects are in good hands.

If you’re someone like me who hates talking on the phone or gets a bit of anxiety when dealing with backed-up email, take my word for it when I say that getting past those hang-ups are the only way you’re going to get your freelance career to survive.

In addition, learn how to communicate clearly and professionally. Keep emails formal (or, at least, not excessively informal), free of basic spelling and punctuation errors, and addressed to the correct person. Even if your client doesn’t share your same level of formality in emails, it’s important to be clear when replying by email or text.

You never know when you’ll have to call up an old email or text to confirm an agreement detail.

Bonus tip: Are you ready for the legendary clients from hell?

Still not sure?

Cards on the table. There are going to be some clients who can only be described as “clients from hell.” There’s an aptly-named website called ClientsFromHell.net, where freelancers share their stories of the clients who almost made them give up freelancing altogether.

Any freelancer who’s been doing this for a while has a few war stories. Browse some stories at that site and see if you’re ready to take on some of the more daunting challenges.

Freelancing is a great path, but it’s not for everyone — and that’s fine.

Speaking personally, going freelance some 20 years ago was the best decision I ever made… for me. I was willing to trade stability for freedom. I was ready to trade days off for an almost constant hustle. I was fine with trading a long, tedious, and wasteful commute for being able to work in slippers.

There were some stumbles along the way, and I’ll admit, a bit of luck. The first few years were tough, but they got better.

I’ve had friends and colleagues for whom it just wasn’t the right choice for them. It didn’t reflect any kind of character defect. It merely demonstrated that they were happier and more productive in a more traditional setup.

They send me postcards when they’re on vacation. I text them pictures of myself working from my backyard.

We have fun.

The point is, freelance life can be sweet, but it can be hard at times, too. It may seem like the solution to whatever dissatisfaction or issues you’re experiencing at your traditional job, but you might be trading old problems for new problems.

I encourage giving freelancing a try. I encourage giving freelancing a fair shake.

But if it’s not working out for you, that’s okay, too.

Now you know.

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