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Thinking about freelancing full-time? Here's what to consider first

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More Americans are freelancing than ever before. According to Upwork, a company whose technology connects freelancers with clients, the freelance workforce brought in $1.2 trillion in 2020, with 1 in 3 U.S. workers engaging in some type of freelancing.

Many freelancers started by dipping their toes in the water first. They may have had their hours at work cut because of COVID, they may have been relegated to working at home, or both. But, they saw an opportunity to take a particular skill to the marketplace and see if someone would pay them for their effort. And, they could try it part-time since they still had a paycheck coming in. Upwork’s numbers show it’s working.

Other people didn’t dip their toes in the water; they took the plunge into the deep end and became full-time freelancers from the get-go. Some of these folks were laid-off, had some stimulus money in their pocket, and were getting substantial unemployment checks. They didn’t want a traditional job; the open road was calling, and they went all-in as a full-time freelancer.

How about you? Are you hearing the siren song of full-time freelancing? It’s a bold move to leave a 9-to-5 job with a paycheck and go solo. In fact, it’s downright scary.

Before you make a move, let’s answer three questions:

  1. What’s so great about freelancing?
  2. What’s not so great about freelancing?
  3. Are you really cut out for this?

You should have some clarity — maybe even a little swagger — after reading this.

What’s so great about freelancing?

Ask a full-time freelancer what they love about their life, and they’ll give you a big grin while they brag about all of the great benefits of freelancing. They’ll tell you your life will never be better because you’ll have:

  • Freedom to work when you want to, where you want to.
  • The chance to call all of the shots — no manager looking over your shoulder.
  • Selectivity with clients — you work with who you want to work with, not who you’re told to work with.
  • No ceiling on your earnings.
  • No frazzled nerves from rush hour.
  • The chance to pursue your passion.
  • No office politics, annual performance reviews, etc.
  • The chance to wear sweatpants any day you feel like it.
  • Fun doing Zoom meetings in your underwear
  • A variety of clients and projects.

Sounds great, doesn’t it? Whoa — not so fast. First, the other side of the coin.

[ Related: 7 healthy work-life balance tips to follow throughout your career ]

What’s not so great about freelancing?

Don't hand in your letter of resignation just yet. First, let’s look at the downsides of freelancing:

  • Feeling isolated.
  • Always hustling for new gigs.
  • Irregular work and cash flow.
  • Juggling multiple clients and projects.
  • Instead of having just one boss, you now have several clients to answer to.
  • No paid time off, no maternity leave, or paternity leave.
  • No employee benefits (health insurance, disability insurance, 401(k), etc.)
  • Nobody to cover for you when you’re sick.
  • No unemployment insurance when you don’t have a single client.
  • Nobody to pass the buck to.

If you’re still thinking that being a full-time freelancer might be just what you’ve been looking for, it’s time to take a little self-inventory and make sure you’re made of the right stuff.

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Are you really cut out for freelancing?

We don’t want you to ever be in a position where someone can say, “I told you so.” To keep that from happening, take some time and answer these questions:

“Are you a hard worker?”

Not only will you be the graphic designer, website builder, writer, (name your trade), you’ll be doing the sales, marketing, administration, bookkeeping, and everything else that needs to be done. This is no 9 to 5 job.

“Are you a good communicator?”

As a freelancer, you have to be able to present yourself well in writing, over the phone, in person, and you’ll need to be able to do it over a whole host of communication tools: Skype, Trello, Basecamp, Slack, Teams, etc.

“Do you walk, talk, and act like a professional?”

When you’re flying solo, there’s only you to make that great first impression. No receptionist, no salesperson, no technician — all eyes are on you.

“Are you good at managing your time?”

Freelancers don’t have to punch a time clock or turn in their hours, so you’ve got to keep yourself on schedule before the day gets away from you, and suddenly you’re wondering where the week went, and you didn’t get anything done. Remember, time is more valuable than money — you can always get more money, but you can’t get more time.

“Are you persistent?”

You’re going to have challenges. Lots of them. Clients won’t pay you, they’ll ghost you. They’ll pull a project at the last minute. It will happen. Can you hang in there? Thomas Edison was talking about freelancers when he said, “Many of life’s failures are people who did not realize how close they were to success when they gave up.”

“Are you motivated?”

Without motivation, you don’t stand a chance. Some people say, “I need someone to come into my life and get me motivated.” What if they don’t show up?

“Are you goal-oriented?”

When a client gives you a project and a deadline, it’s your job to get it to the finish line — on time.

“Are you flexible?”

Some days you’re going to get up at 5 a.m. and work until midnight because you have a commitment to meet. You may have to work some Saturdays or half a day on a holiday. Clients don’t care about your childcare problems or your air conditioner dying on you. You have to get their work done, no matter how long it takes.

“Are you self-disciplined?”

Without self-discipline, all of the other characteristics we’ve looked at won’t matter much. You’re not going to have a boss to put their boot up your backside when you’re “not in the mood” to get your work done. As one wise sage put it, “Discipline weighs ounces, regret weighs tons.”

If you think you have what it takes, go for the gold. Being a successful full-time freelancer isn’t a zero-sum game — there are plenty of opportunities out there for everyone.


The information and content provided herein is for educational purposes only, and should not be considered legal, tax, investment, or financial advice, recommendation, or endorsement. Breeze does not guarantee the accuracy, completeness, reliability or usefulness of any testimonials, opinions, advice, product or service offers, or other information provided here by third parties. Individuals are encouraged to seek advice from their own tax or legal counsel.

Work-Life
Published January 13, 2022