Is freelancing right for you?
I have actually worked at the beach before. Just sayin’.
If you’re considering freelancing, you know it’s a scary plunge. Going from a secure paycheck with insurance and 401k included, to “eating what you kill” from week to week is a big change.
I started freelancing in 2018 to build up a marketing portfolio, thinking it would help me make a career switch. I was, at the time, a Business Analyst (no, I don’t know what it means either. No one did).
Then, in 2020, I realized I hated working for other people, I hated having them set my schedule, and I HATED doing the same thing day-in, day-out, over and over. Working for someone else’s vision full-time just didn’t provide the level of newness, challenge, and flexibility I needed to be happy.
This picture looks eerily like one of the places I worked… and I often looked as upset as this guy.
So, despite warnings from literally every grown-up in my life, I became a full-time freelancer. And it’s… *drum roll please*... gone pretty well!
I’m not going to say it’s been easy, and I won’t pretend like every month has been a great one (financially or stress-wise). But I know that freelancing works for me. I’m happier than I’ve ever been.
However, freelancing is NOT FOR EVERYONE. If you’re interested in it, it’s probably calling to you for a reason, but before you take the plunge, you should make sure it actually fits you: your strengths, your lifestyle, and your flaws, too (perhaps most importantly, freelancing fits well with what many people would consider my “flaws”).
So, from four years of freelancing and counting, I’m going to share with you the traits you need to make this work. You can decide whether this sounds like a fit for you or not.
If you want more advice on becoming a freelancer, download our free guide: 9 Ways for Creatives to Make Money Online. It will walk you through the most profitable ways to begin your freelancing journey.
Now, let’s get into the real questions that will tell you: is freelancing right for you?
Are you self-disciplined and self-motivated?
I don’t mean that you have to get up at 5 AM every day, run three miles, and eat kale by shoving it directly into your veins (you get the most nutrients that way).
I mean, do you have an inner drive or ambition to keep you moving? Or do you need encouragement from other people to stay motivated?
Freelancers have to pat themselves on the back. What’s more, you have to keep yourself going even when things suck. You have to sit down to work knowing nobody is going to applaud you or care if you don’t do it.
When I had a boss, he was always there when I finished a project with a ton of feedback, and either praise or censure (I hated that). But that’s the motivation of the traditional business hierarchy: there is someone who cares, for better or worse, how you do.
This was how my boss and I looked.
Freelancing clients are not like this. Surprisingly enough, most clients don’t even get mad or anything if you’re late. When I’ve been late with projects, people are generally understanding.
This means that there is very little external pressure to get things done. To stay on task, finish things on time, and make enough money to live on, I have to get my motivation from inside myself. I have to be my own cheerleader, and my own critic.
It works for me (most of the time) because I am an ambitious person and I hate being bored. I like getting new clients, making more money from the ones I have, and finding new ways to stretch my skills. Nobody has to tell me to do this, and honestly, I get annoyed if someone takes a ton of time to praise me. It’s just not necessary for me to stay motivated.
There is nothing wrong with being externally motivated. That means you’re probably a great team player and you work well collaboratively. People probably like you more than they would like me. It also means you will have a rough time as a freelancer.
Do you like being alone?
Me and my three personalities going over my work for the day.
Freelancing is, with some exceptions, a rather solitary pursuit.*
You’re generally remote, and the things you’re doing are, by definition, something that can be done without being embedded in a team. Also, clients generally use you when they don’t have a ton of time, so they’re just as happy to avoid meetings as you are (most of the time. Some clients LOVE to get you on the phone. I avoid these clients).
I am very introverted and need very little social time with people. I get exhausted if I have social engagements more than once a week. My pitbull and my boyfriend are usually more than enough. Working in an office was way too much social interaction for me.
For me, freelancing means that after maybe one or two client meetings, I can zone in on my work by myself and have that lone focus time. That makes it AWESOME for me.
If you know you need people around or you get depressed, freelancing or any kind of “solopreneurship” may not be right for you.
*A few exceptions: some people freelance with a partner. I know several videographers/video editors who make this work well for them. If freelancing sounds great to you, but you don’t like working alone, finding a partner might make it the perfect fit!
Additionally, for certain in-person freelancing gigs, such as being a freelance DJ, clown, or audio equipment provider, this won’t matter as much.
Do you bounce back fast from loss or rejection?
Moving on quickly to a new thing is 100% necessary as a freelancer.
To give you an idea, I recently sent out 20 applications for gigs. Some of those jobs, I was even invited personally by the client to apply. Out of those applications, I was invited to 2 interviews (10% response rate), and I got 1 client (5% success rate).
This is MUCH better than I did when I was starting out. Then, it was more like 80 applications would turn into 1-2 gigs.
If I let each of those rejections or no-answers get me down, I would have quit this a long time ago.
When I apply to a gig, I don’t wait for their response. I have applied to a gig and not heard back for 3 months, and then got the job out of the blue. I have had someone tell me, week after week, for three months straight, that they were ready to give me thousands of dollars to write a blog post… and then they ghosted me.
People use freelancers because they’re convenient. That means they will ignore your application (even more than regular job apps) unless they want to use you, and when they’re done with you, they will drop you without warning or explanation.
Me, happily moving on to my next client after dumping a bad one.
You have to move on quickly. If you dwell on that big client that’s stopped responding, you’ll waste time and emotional energy. If you wait for a response from that “dream gig” before applying to anything else, you won’t make rent.
If you know you are the type of person who needs a lot of time to process loss and move on to something new, or the idea of constant rejection or ghosting sounds hellish, freelancing is not for you.
If you can keep bouncing on to the next thing like some kind of a gig economy Tigger, you’ll have a much easier time.
Can you handle multiple projects at once?
Multi-tasking, especially when you first start out, is necessary. It is very rare that you will find one contract that can support you completely.
If you do find something like that, you still need other active clients, because even the best situation can suddenly disappear.
I’ll give you a real world example: I had a contract to write children’s stories for a virtual publisher. They paid great. Some of their freelancers were making $8k a month just writing stories for them.
Now, they weren’t paying so well that you could pump out $8k worth of stories AND do other work. So people were relying on this client for all of their income.
Then, one magical day, their bank told them, “No more payments to America.”
Suddenly, they can’t pay their freelancers. Some US writers were owed over $20k for their stories.
This problem arose three months ago. They still haven’t paid a bunch of people. The project is shut down until they can figure out the banking issue.
Now, this wasn’t a problem for me, because I had four other active clients in addition to this publisher. When they shut the project down, I simply focused on those clients, and I didn’t see a dip in total income.
The people who were only writing stories for this publisher were screwed. Now they had to scramble to find enough new clients to make up for this one. They went from consistent income to nothing at all overnight.
This can happen to any freelancer (I’ll talk about that in a second), but by having a number of active projects, you can mitigate the risk of suddenly having no income at all. If you find it challenging to keep up with several projects at once, and prefer to finish one thing completely before moving on to the next, you will have a hard time freelancing.
Can you underspend and save your money?
As a freelancer, you don’t get paid sick leave. If you don’t have money in the bank to cover your time off, your only option is to rack up debt.
I had several months this year where health problems meant I couldn’t work as much as I usually do. I was still working as much as I could, but I wasn’t making nearly enough to cover my medical expenses, because being sick was exhausting full-time by itself.
When I have a flush month and make good money, I live below my means and put as much of it away as possible. Luckily, I had been doing that previously, so I had savings to pay for my medical bills.
This is why I recommend, before moving to freelancing full-time, that you have at least three months’ worth of expenses saved. An accident or illness could drain your energy and your finances, and as a freelancer, you have no safety net.
Even without the risk of health problems or other big bad problems, there will be months where you make very little, even if you work very hard, simply because you don’t have the luck to connect with clients who need you that month.
During the good months, you need to save for the bad months. If you don’t trust yourself to save your money for a rainy day, freelancing is not a smart decision for you.
Are you confident in your skills (or can you fake it)?
Freelancing is incredibly competitive. There are people on Upwork (a popular site to find work as a freelancer) with 15 years experience offering their services for $15 an hour (which is INSANE).
I love Upwork, but there’s a lot of competition!
If you’re going to make a living wage, you need to sell yourself hard. You need to know your strengths, know how to market those strengths, and make it sound like your clients are losing out on the opportunity of a lifetime by not hiring you.
Not willing to brag about yourself? Feel insecure and can’t hide it? You will not get clients.
Pro Tip: Check out StoryBrand and Fascinate to find out how to market yourself. I return again and again to StoryBrand’s one-liner and Fascinate’s 49 Archetypes when applying to clients.
When I began freelancing, I had next to no experience. I had no samples. All I had was a very convincing sales pitch about myself, and confidence in my ability to write well and learn quickly. That was all I needed, but the sales pitch was absolutely necessary.
“Here, you’ll see Reason #373 that I’m so awesome.”
You don’t have to have a huge ego (in fact, it’s better if you don’t, because otherwise you’ll have a difficult time with the upcoming rejections). But you at least need to be able to fake it.
In interviews, when a client asks me a question, I always have something to say. I never leave it at “I don’t know.” I don’t lie to clients, but I make sure I use what I do have to look knowledgeable about whatever they need.
If you know you cannot talk yourself up, you will have a very challenging time getting clients, especially if you are young or new to your field.
Can you say no?
Clients will ask you for everything and anything, and they will ask you for it for free if they can get it. If you say yes to everything, you will be exhausted, broke, and sad, very quickly.
For a particularly awful example of when I had to say No, watch this vid: My Worst Client Ever.
I’m not particularly good at boundary setting in my personal life, but after becoming disenchanted with capitalism, I became very good at it at work.
Here’s the secret: you don’t owe your bosses/clients a damn thing. Hell, you don’t even owe them a completed project (unless they already paid you, and then you literally owe them, but you can refund the money, and then you owe them nothing again!).
Wow, thanks for the thumbs up. That’ll pay my rent.
Capitalists will try to emotionally manipulate you into “being a team player,” but at the end of the day, they’re exploiting your labor to make profit, and you’re allowing that so you can get some money for your labor. Companies try to keep you under their authority by praising “loyalty” or “work ethic,” instead of paying you well or giving you other real perks.
That’s the beauty of freelancing. It’s kind of anarchy. You and the client are actually on an equal playing field: they need a thing (often desperately) and you need money. You make a deal based on that, but either of you can back out of the deal or try to change the terms at any time.
This is why you need to be very, very, very good at setting boundaries with clients. Because they will try to change the terms on you, and you have to stand firm.
Here’s some examples of things you may have to say no to:
“Can you finish this rush project in the next hour?”
“Can you work overnight/over the weekend/over your vacation to get this done?”
“Can you give me your personal cell number so I can reach you outside of your work hours?”
“Can you do one more thing for me [without increasing the price]?”
“Can you completely revise this [without increasing the price]?”
“Can you give me a discount/do this for free as a ‘trial’?”
And this final thing is never explicitly asked, but you will have to set a boundary on it: “Can I treat you badly and insult you and your work?”
I’m addicted to finishing a project as the sun rises.
Now, there have been projects where I worked overnight, but that’s because I like to work at night. I often start working at 1 PM and work until I’m too tired to keep going. That’s the beauty of freelancing, who needs a 9-5?
I have also done rush projects and worked over the weekend, or given my cell number for interviews. Sometimes I like the adrenaline of finishing a project with a tight deadline. The point is that sometimes you will be totally fine with doing these things. Again, that’s the beauty of freelancing.
But it has to be my choice. When I don’t want to, I tell clients no. I hold my personal time sacred. I set my own hours. And I never, NEVER do additional work without charging more money. I don’t even meet with my clients without charging them for my time spent in the meeting.
If you can’t say no, you’re not getting any freedom by becoming a freelancer. You’re just setting yourself up to be taken advantage of by a whole group of people, instead of one company, who at least pays for your insurance.
Learn to say no, or freelancing will drain your bank account and your spirit. If you aren’t good at saying no, work on that before doing freelancing full-time.
Can you set a schedule for yourself that doesn’t make you want to die?
I had to learn this skill. When I first started freelancing, I was working a full-time job, as well as freelancing 20-40 hours a week. I wasn’t doing anything but working.
I made a lot of money in that period (yay!), but the stress and constant effort literally broke my body (boo!). I’m actually in physical therapy right now to recover from the damage that did to me, as well as the damage done by ignoring other stressors so I could work work work.
I didn’t exercise. I didn’t clean the house. I didn’t relax. I barely slept. I barely ate. I just worked.
It turns out that’s not very healthy! Or sustainable! I basically pushed my body into a state of near-constant exhaustion.
Now, I’ve learned to set time to take care of my body, do things for the sake of fun, and see sunlight on occasion. This makes life much better!
Additionally, feeling better has helped me feel more confident and value myself more highly, so I charge higher rates for my work. I work less, and make more money.
If you want to be a freelancer long-term, you need to learn how to set a schedule that makes you like living and like working. Otherwise, you will burn out and drop out of the gig economy (like I said, I had to take a step back a few months this year because of health problems, and it was partially because I lacked this skill).
Take care of yourself first, and you’ll love the life you build as a freelancer.
So… is freelancing right for you?
Remember, the beauty of freelancing is flexibility. If you want flexibility, it could very well be perfect for you. Just, you know… take time to think about it. Consider the traits and behaviors I’ve listed above. And if you still want to do it, and you feel like it’s right for you, I believe you can do it!
Do these traits sound like you? Or maybe they don’t, but you think you can make it work? Let us know what you’re thinking in the comments!
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