Working as a Freelancer: The Pros and Cons of Going Solo

Working as a Freelancer

In my early 30s, I quit a safe, well-paid, fulfilling job at a well-known magazine to become a freelance writer.  

To this day it remains one of the stupidest things I ever did. 

But not because it was a bad idea. There are a lot of good reasons to choose freelance or full-time work, if you’re lucky enough to have a choice. But before anybody goes the freelance route, they need to know what they’re getting into. 

The rise of the so-called gig economy — which some shrewd business leaders invented and which turned out to be much better for them than for the workers — and the pandemic-driven proliferation of remote work have put freelance work in play for more workers than ever before. You may be thinking of working as a freelancer yourself. 

If so, I’d love to help you avoid some of the mistakes I made, and go in with your eyes open, in hopes you can make a go of it. Because for certain people in certain circumstances, freelancing can be a perfect fit. Freelancing offers levels of freedom and variety that full-time work can’t. But it also comes with burdens and risks you don’t face as an employee. 

First, to be clear, by freelancing, we mean  performing a service for a company or client for a fee. Freelancers  aren’t on the payroll; they aren’t employees. Their work is often project-based, or performed during an agreed-upon timeframe. They’re  sometimes paid by the hour, sometimes by a flat fee based on both parties’ estimate of what it will take to do the work.

A freelancer is also a small business, even though it's just you (and believe me, it’s just you). That might be the most important thing to get your head around. Keep it in mind as you read through all the pros and cons below.


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Pros and cons of life as a freelancer

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So what does becoming a freelancer look like? We’ll start with the good stuff.

The pros:

  • Assuming you’re planning to freelance in an industry where you already have the skills, tools, and network you’ll need to find and do the work, you can jump in without a big upfront investment.
  • Because you’ll probably work for multiple clients, and start new projects frequently, your work will rarely feel repetitive. If you’re the kind of person who loves starting something new but gets bored with doing the same things over and over, you’ll like the variety of freelancing. 
  • If on the other hand you’re just starting out in your field, freelancing is a good way to rack up experience. This is especially true in creative fields like writing or design, where employers business leaders care look more closely at your work than your resume.
  • You can theoretically work from anywhere, though post-COVID this is obviously true of more and more full-time gigs as well.
  • You can often — but not always — set your hours. Beyond meeting deadlines and showing up for certain meetings, how you structure your day is up to you. This is where freelance work can be super attractive for parents of young kids.
  • You can choose your projects — at least in theory. While a company may have a set of deliverables they want you to meet, you have the power to say no to working with that company from the onset. Of course, the more you need work (i.e., money), the less selective you’ll be. 
  • Because you decide how many projects you take on, you control whether freelance work is a side job where you earn extra cash or a full-time gig. 

The cons:

  • Pay is often very low, especially for new freelancers.
  • If you want to freelance full-time, be prepared to spend years building up a client base that will be large enough to provide steady, reliable income.
  • Your workload and the number of clients you have can be incredibly inconsistent. Sometimes you may have too many new clients, and other times, too few. You’ll need to be, or learn to be, adept at managing your money, so the income from the busy times keeps you afloat when work dries up.
  •  It’s easy to unintentionally work long hours when the one setting those hours is you. You’ll want and need to do good work. But you can’t burn yourself out. Striking the right balance can be hard.
  • Excellent organizational skills are critical. Freelancing often requires you to juggle multiple competing priorities at once — and you can’t tell any one of your clients they’re a lower priority than another
  • Taxes. It’s a real headache. And if you screw it up you’ll get absolutely clobbered. I strongly reccommend finding and hiring an accountant before you start. They’ll help you figure out how much to set aside for taxes and when to make quarterly payments. 
  • Employee benefits. There are none. No health insurance. No paid vacations. No snack rooms crammed with Clif Bars. You’re on your own for all of that stuff. Health insurance alone can be a real killer — research it before you take the leap so you know what to expect.  

The most common freelance career fields 

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If I haven’t scared you away from freelancing yet, you have a few more things to consider. Chiefly, figuring out how much freelance work exists in your field. 

Just because freelance gigs are on the rise does not mean the work is equally distributed across industries. Some have more opportunity than others. The industries that typically offer the most freelancing jobs:

  • Writing: Most magazines, online and off, and websites run primarily on freelance and contract writers. Same goes for marketing copywriting. Look for roles with titles like author, content writer, copywriter, technical writer, and reporter.
  • Bookkeeping: A lot of accountants are self-employed, since the skills required for accounting have immense value in freelancing. And lots of small and mid-sized companies don’t need full-time accountants.
  • Marketing: Marketers can build up rosters of individual clients or serve as consultants for larger companies. Identifying a speciality — such as social media management or PR — will help develop a reputation and differentiate you in a crowded field.
  • Graphic Design: Lots of businesses can’t afford or don’t need full-time designers. But almost every business needs graphic design at some point. 
  • Virtual Assistants: If you're a skilled administrative assistant, finding small business leaders who need help with with their administrative tasks but don’t want to hire full-time assistants can provide a good, steady income.

One last thing to note: There are a lot of variations on freelancing arrangements. Freelance contracts can take the form of flat fees per project, temporary contracts, long-term contracts, consultant work, or contract-to-hire scenarios, where you have the potential to become an employee after a set amount of time. It varies by industry and by client. You’ll want to figure out what’s most prevalent in your field, and what you’d prefer.

The soft skills you need as a freelancer

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Before you take that final plunge into freelancing, you're going to want to take a good, hard look at yourself. You presumably have the job skills and technical know-how you need to make it, but what about the softer stuff? 

It comes down to: are you made for this? I wasn’t — I hated the administrative parts of the job, the constant hustle for new work, and the tax crap. I just wish I’d known that going in. Now you will. 

The soft skills you’ll need:

  • Organization: You'll be handling multiple, complex tasks simultaneously.
  • Persistence: You need to be relentlessly proactive about finding new work and prospective clients. Including when you’re super busy — you don’t want to have nothing lined up when that work wraps up. 
  • Discipline: Freelancers are their own bosses, with their own schedules. This means that to stay on top of things, you need the internal drive to remain on task when nobody’s watching.
  • Resilience: You’re going to hear “no” a lot. You’re going to hit dry spells. You'll need to be strong enough to weather all of that.
  • Communication: You need to be great at conveying ideas to others in various mediums, since most of your communication will likely be remote. 

How to find freelance work

If you’ve made it this far and I still haven’t talked you out of it, great! I’m jealous. Freelancing works well for a lot of people; maybe you’re one of them. 

The next step is to start preparing yourself to make the jump. Here are a few things to be sure you have, or at least think through, in advance.  

  • A business plan
  • A marketing strategy and marketing plan
  • A website that advertises your services, along with an online portfolio of your work
  • A reliable way for clients to contact you, whether that’s a business email or a phone number
  • A LinkedIn profile helps to establish a track record for your work, and you can hunt for freelance gigs through LinkedIn, too

Some of the places where you can find freelance jobs:

If you’re going to need audio or visual tools in your freelance gig, check out Descript’s blog.

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