A lot of people dream about quitting their job and becoming “the boss,” but they don’t think about how it will actually play out.
In case it’s not obvious, I enjoy talking about the downsides of freelancing – not because I hate it (I chose to do it!), but because it’s rarely talked about.
Because of that, many people go into it with the wrong idea.
So if you’re on the fence about becoming a freelancer, or really want to try it, but have no idea if you’re cut out for it, read on for the 10 signs you might not be meant to freelance.
1) You Can’t Stand the Idea of Irregular Income
First and foremost, you have to be good at managing your money if you’re going to be a freelancer. That’s because you’re dealing with an irregular income.
And when I say irregular, I mean it. You might have clients that pay you once a month, once a month on a specific date, every other week, or every week.
Or you might have clients that never pay you and stop answering your emails and calls.
You also have to be diligent enough to set aside a hefty chunk of your income for taxes.
In a nutshell, if you love the stability of getting a (mostly) guaranteed paycheck, and not getting paid would send you into panic mode, you might want to re-think being self-employed.
You’re responsible for invoicing and getting paid. You have to track down late-paying clients, or structure your business in such a way that you receive a percentage of payment upfront, and the rest when you deliver your work.
2) You’re Afraid of Rejection or Criticism
As a freelancer, most of the time, you need to be able to sell yourself. Whether you’re selling services or a product, a lot of your success rests on the art of selling.
This is something a lot of people don’t figure out, even when they’re going through the motions, because it’s not selling yourself in a scummy, car-salesman type of way. It’s much subtler.
You have to be okay with reaching out to people and “pitching” them on your services or your product. If you’re not, you’ll never get anywhere.
Unfortunately, rejection and criticism is something every freelancer faces. No one is immune to it. You’ll send email after email with no responses back. Or you might get turned down harshly by potential clients. Or your clients may not like the work you produce.
So if you’re deathly afraid of rejection and criticism, to the point where you can’t put yourself out there, freelancing might not be the path for you.
3) You Get Distracted Easily
Most people want to freelance because it means working from home (or wherever you want).
Well, working from home (or from an exotic location) comes with a lot of distractions.
You might have kids. You might have pets. You might have family or friends that drop by (because you’re clearly not working, you’re just at the computer).
You might have dirty laundry that needs cleaning. Or you might have an entire living space that needs cleaning. Or the sink might be full of dishes calling your name.
Oh, and then there’s the inevitable errands that need to be done. And let’s not even talk about social media or web browsing, since nothing is blocked on your home network.
You have to possess the willpower to drown out all of these distractions, or you have to relocate to an area where you can work distraction-free. That might not be easy if you’re traveling and want to take in the sights.
Just be aware that working from home has its pros and cons.
4) You Lack Motivation
If you get distracted easily and lack motivation…you might have a very difficult time finding success as a freelancer.
Every freelancer I know is extremely motivated. That motivation comes in many forms, but most of us hustle because we need the money.
If you’re not pitching people or doing the work you need to do, you’re not getting paid.
Those who choose self-employment are typically called “self-starters” because they take initiative and aren’t afraid to experiment.
If you hate working no matter what it is you’re working on, you might need to figure out a better career path…and one that isn’t freelancing. Getting up, going to your computer, and forcing yourself to work isn’t any better than being stuck at a 9 to 5.
I highly recommend side hustling first to make sure you actually enjoy freelancing and can be motivated enough on your own to do it full-time.
5) You’re Uncomfortable With Networking
Similar to being afraid of rejection and criticism, you can’t be afraid to reach out to others in your network, whether your goal is to get a gig or simply make connections for the future.
I’ve said this before, but I got all of my clients through referrals, and many other freelancers I know have had a similar experience. It’s who you know, 100%.
Why? Because most freelancers can’t be bothered to show up, and if they do, they don’t do the job correctly.
I hate to say that, but it’s been my experience and the experience of others who have dealt with contractors.
You need to be different, and that means putting yourself out there and proving that you’re valuable. I’m not saying you need to work for free, but if you have no desire to network and want gigs to fall into your lap, you’re not going to get very far.
Your network is one of your strongest assets as a freelancer; if you want to work alone in a vacuum, you might need to be extra choosy about what type of freelancing you do.
6) You Need Someone to Tell You What to do
This ties in with motivation. Yes, you’re “the boss” when you freelance, but that comes with a lot more responsibility than you might realize.
Besides being responsible for getting paid, you’re responsible for taxes, getting your own health insurance, setting your rates, figuring out what services you want to offer, figuring out how to market those services, developing sales funnels, funding your retirement, structuring your business, managing your workflow, delegating and outsourcing (if and when necessary), and meeting deadlines.
That’s not an exhaustive list, either.
Is your head spinning yet?
Being your own boss is very rewarding, but it’s also very challenging. If you’re the type of employee who needs a push in the right direction every so often, there’s nothing wrong with that, but you might have a difficult time as a freelancer.
It’s up to you to get all your work done on time without clients breathing down your neck, and that’s only half the equation. You also need to be okay with administrative tasks (until you can outsource them) and be willing to learn how to run your business.
7) You’re Not Great at Communicating
This is a huge one. Communication is crucial as a freelancer.
Miscommunication happens all the time – even to the best of us who try and over-communicate. Why? Because most of us are functioning online, and words can get mixed up very easily.
Do you hate reading email? Do you hate responding? Does the idea of having your inbox flooded make you anxious? Then you might want to re-think freelancing.
Sure, some clients enjoy phone calls, but most of the freelancers I know hate them (myself included), so email is pretty much your only other option.
That means it’s imperative to ask questions and get the answers you need before moving on. You should also become skilled at drilling down to the point so you’re not sending unnecessarily long emails.
I shouldn’t have to mention this, but proofreading your emails goes a long way toward ensuring better communication, too.
Being able to communicate effectively is a skill that you’ll develop over time, especially as you work with more clients, as each is different.
But the idea of communicating with people is one you should be comfortable with before thinking about self-employment, especially if you have thoughts of building a team in the future!
8) You Love Your Benefits
Benefits as a freelancer are tricky. It’s a sore spot for many of us.
First, you don’t get sick or vacation time. You also don’t typically get overtime. That’s up to you to figure out.
Most freelancers I know make a lot of sacrifices where their time is concerned – myself included. I work weekends and at all hours of the day to make sure my clients are happy.
But that can mean your health takes a backseat…and when you don’t have sick time, you need to work through it, or ask your clients to be understanding.
If you want to go on vacation, you should probably give your clients more than enough notice, and work ahead so that all of your projects are finished up beforehand.
So you may not have to get time off “approved” by a boss, but you have to figure out how to work around these limitations and set boundaries.
Of course, you’re also responsible for getting health insurance, and the process isn’t fun. At all. It’s also quite expensive, depending on where you live and how much money you make.
Like I mentioned before, you also need to fund your own retirement. There’s no 401(k) matching here. Self-employment gives you a few more options as far as accounts go, but you need the discipline to save.
All this to say: if you enjoy your job and have amazing benefits, definitely take that into consideration when thinking about freelancing, because you might end up in a losing situation.
9) You Can’t Leave Work at Work
Are you horrible about leaving work at work? Do you get home only to rant to someone about the bad day you had, or how much your boss sucks?
Most of us have done this at some point or another, but it’s not healthy. It’s even worse as a freelancer, because home typically is work.
Many of us are bad about disconnecting since our email and social media are on our phones, and if your work computer follows you around, it can be easy to work all the time.
If you have a not-so-pleasant client or project that’s calling for your attention, you might not be able to get it out of your head when you’re in the same environment you work in.
Having an office or a space (like a library or cafe) that you work out of is beneficial for this reason.
This isn’t a deal breaker, but you should consider how your mental health might be impacted by the move to self-employment.
10) You Have the Wrong Idea About it
Finally, freelancing is not for you if you can’t accept the realities of it – both good and bad.
We covered a lot of ground here, so I think you get the gist of the cons of freelancing. But I want to reiterate that it’s not unicorns and puppies all the time like it’s portrayed on social media.
You can’t lay around in your PJs all day watching Netflix. You can’t travel non-stop and blow off deadlines because you’d rather be sight-seeing. You can’t spend money before it’s in your account because it’s never guaranteed.
Freelancing is great, but it takes a certain person to succeed with it. I have many friends who have no interest in it whatsoever because they enjoy their freedom outside of work.
You have to be good at managing boundaries and asking for what you’re worth, otherwise you’re going to end up like a doormat.
You Can Always Pick a Different Side Hustle
So maybe you’re not meant to be a freelancer. That doesn’t mean you can’t work your 9 to 5 and side hustle – you just have to structure your side hustle a little differently.
Freelancing is just one type of hustle. You can also be a consultant/coach, or you can build your own products.
For example, perhaps you’re great with people, but you hate deadlines and want to be picky about when you work. As a consultant, you’re the “expert,” and you get to choose which products/companies/brands you work with, and how you work with them. Your job is to offer advice, and you can package this as a one-time meeting, or a series of meetings, on your schedule.
Instead of ongoing work, you can take on projects or clients when it’s convenient for you and structure your schedule accordingly.
Or maybe you’re not a people-person, and would rather build a product you can sell to companies. This might give you a passive income stream, and the only deadlines you have to deal with are the ones you set for yourself. (However, you may have to offer support for your product.)
If you want to learn more about side hustles consider checking out DC’s book Hustle Away Debt, which helps you pick the best side hustle for you and optimize your side hustle.
There’s Nothing Wrong With “Traditional” Work
I’m going to end with this: if you enjoy your 9 to 5, then there’s nothing wrong with wanting to stay.
I often see people commenting that freelancing isn’t their cup of tea because they’re fine with their job, and that’s great. They shouldn’t have to defend the fact they want to work a traditional job!
Not everyone wants to quit their job, and if that’s you, you don’t need these 10 signs to tell you otherwise.
Maybe you want to keep your hobbies as hobbies and not get paid for them. Maybe you want a clear divide between work and home-life. Or maybe you just want to dabble in freelancing whenever you need the extra cash.
Whatever the case may be, choose whatever path is most fulfilling to you.
______________
Freelancing isn’t for everyone, and it’s important to have a good idea of what “being the boss” entails before you make the leap. Carefully take these 10 signs you’re not meant to be a freelancer into consideration when thinking about working for yourself.
Check out the following posts for some additional resources:
- 6 Steps to Take to Become a Full-Time Freelancer
- 50+ Legitimate Ways to Make Extra Money At Home
- 5 Side Hustles that Make at Least $500 a Month
- 6 Skills That Can Be Turned Into a Side Hustle
- The Ultimate Guide to Side Hustling
- How to Start a Blog (That Makes Money)
Are you a freelancer? Did you think it would be easier than it actually is? What were some unexpected things you’ve had to deal with? If you’re not a freelancer, do you think it’s for you?
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I’m not sure if I want to keep freelancing after I get my degree just because IT’S LONELY. What I miss about working at a 9-5 is the feedback you get from work friends and other co-workers.
Sometimes I miss the camaraderie. It’s probably because I’m an extrovert. Thanks for not upholding freelancing as the only way to work. I’ve noticed there are a lot of people in the blogosphere judging the 9-5’ers.
Your other point on freelancers that don’t do the job correctly. I wonder if that’s because they have a whimsical idea of what it means. “Oh it’s freelancing, it’s not a serious 9-5 job, whatever…” I think there are a lot of people that go into freelancing and don’t take it professionally as they would a 9-5.
Yes, Lila, you’re totally right! I’m an introvert, but I miss that interaction. I don’t miss the office drama, but the loneliness can definitely get to you. I’ve thought about joining a co-working space for that reason.
You might be right. I can’t speak to that because I want my work to speak for itself. As writers, our name is usually attached to everything, so I’m very aware of how my work reflects back on me. But if you don’t have a good work ethic in general, I suppose it’s easier to brush it off, especially when most interactions happen online, and it’s easier to “hide.”
Absolutely true, fo rhte moment I prefer a regular income and use side hustle and extra and irregular income for savings, but yes for the moment I’m not ready to beboss of myself, I need other time to be weel prepared -also financially
That’s great that you recognize that, Giulia! And you’re gaining valuable experience in the meantime.
I think I agree with all of these Erin. Thankfully my wife had started freelancing several years before I quit my job so I got to see, through her, what it was like so it helped me appreciate things a little bit more once I quit my job. That being said, it’s not for the unprepared/those uncomfortable with change. The unexpected thing I had to deal with, and still do, is distraction. As you know, it’s just so easy to allow something to take you completely off task. I’ve found some things to help me with that, but is a battle at times – especially when you have family that thinks you’re just “playing” on the computer.
Yes, if someone you know (or live with) is already freelancing, shadowing them or asking them questions is a great idea, too. So many people have the wrong idea about what it means to work from home or work for yourself, and experiencing it second-hand can help.
I think distraction is one of the worst things we all deal with, especially when it’s distraction in disguise. You might have a big goal you want to accomplish, and lots of little goals, and those little goals can even be a distraction.
All great points! While I don’t freelance (yet), I’ve learned many of these lessons through running my blog. Distractions are huge! I’m currently experimenting with working in different areas of my house to keep “work” and “family” more separated.
Oh yes, running a blog will definitely give you a preview into what it’s like! I love working from different locations – even small changes in scenery can help.
I tried freelancing but I quickly realized it wasn’t for me. I understand you have to first volunteer articles in order to build a reputation and I believe I was simply more motivated to write for myself at the time in my life than for others because the payback seemed more immediate. However, I know people make good money this way and it is certainly a viable career option for those who have the right qualities. This list is a pretty good guide to go by!
I like that point – that you were more motivated to write for yourself. That’s how I started out, and I think it’s a good idea for everyone to explore what they want to freelance in before going full force with it. If you can’t enjoy doing it for the sake of doing it (for yourself), then you probably shouldn’t be trying to make a career of it!
I recently quit my day job to be a full-time blogger and freelancer. It’s scary but I think it will be worth it. I may reach out to you for some pointers. :-)
oh man! This is an awesome post! Possibly the best that I have seen about the topic. I’ll tell you why…. We see on so many blogs the glamour of working from home. Sure, you may not have to put pants on until noon and you can go to the gym whenever you want. However, it truly takes hard work and dedication.
Although I would love to work on my blog full time, I am so used to consistent income. I would have to make quite a few lifestyle changes to get used to inconsistent income.
Great article there Erin! In my humble opinion, to be a good freelancer often comes down to leadership, but not int terms of leading a team (although that IS an common situation), but being a your own leader. I myself used to have sever issues with motivation, focus and confidence, but at a certain point I realized that I simply had to stand up to myself. As a wise man once said, that the mind is a instrument and You/I/We should be it’s master, not it’s slave. That’s where I realized I had to buckle up and overcome my own insecurities, which eventually led to being, acting and as a better and more confident professional, which was crucial to my overall performance and most importantly – the way I feel! Cheers
Great points Erin. I like getting regular income and I don’t think I would want to sacrifice time with family and other activities to go full time freelancing. I’m happy keeping it as a side hustle for now while working on excelling at my full time job.
Wow! I think that freelancing in retirement will be about right for me. I would find it stressful to have to rely upon the uncertain income. And that’s way too much to juggle all at the same time. I love writing and I love writing about about the power we have via our money management – but part time, and with no necessity of making an income from it. Thanks for an honest peek into full-time freelancing, Erin.
I really like two of the points you gave: being afraid of rejection and lack of motivation. Those are super important. You HAVE to have a strong desire to do what you do in freelancing. It gets you through those days when you would rather just want to lay in bed, watch Netflix, or get distracted with other things.
Lauren Berger, CEO of Intern Queen, said you’re going to get rejected for the rest of your life, so get used to it and embrace it. I like that perspective towards it.
This is a great list and really made me think. There are some things on the list that I know I need to work on if I want to pursue freelance work. As an introvert I don’t feel like I am naturally go leveraging the contacts in my network. Thanks again for the awesome article.