The worst things about freelancing
I’m not trying to be depress-y here, but I want to be real with you.
Not everyone should become a freelancer. It’s a difficult path like any other business.
But if you’ve chosen this path, I want you to succeed. And that means being honest with you even when it sucks—not to scare you, but to prepare you.
With that in mind, here are some of the worst things about freelancing from my years in the business.
(PS – these may not fit your definition of “worst.” If that’s the case, heck yeah! I want that for you)
1. Sales is #life
For the love of god, I do NOT mean you pitch everyone constantly (don’t do that).
Let’s be honest with each other. All entrepreneurs are always selling, all the time. It works in gradations:
On an actual sales call: You are selling.
Talking to possible clients IRL or online: You are figuring out if they might need your services so you can later sell.
Talking to general professionals who are not your ideal clients: Generally making sure they know what you do so they can refer you to possible clients.
Talking to someone at your great aunt’s birthday party who loves you but doesn’t know what “being a freelancer” means: Trying to give them the most basic explanation possible so when they talk about you, at least they aren’t making things actively worse.
The list goes on, but the point is simple: You need to always sell. It can be tiring after a little while (I heavily advocate building boundaries like knowing who you will never try to sell to–a.k.a. your friends–so you can live your life).
2. Bad clients are the same as bad bosses
Ohhh, you got into freelancing to work for yourself? And be your own boss? The joke’s on you! Now instead of one boss at a job, you have multiple bosses–you just call them clients.
A bad client can make you just as miserable as a bad boss.
Admittedly, it’s different because of quantity:
You have one boss, but they can make your whole day awful (and control 100% of your revenue)
You have multiple clients, but each one only occupies a small portion of your day (and revenue)
Generally, I prefer multiple clients to one boss, for a variety of reasons. But it sure as heck sucks when every client you have seems to be having an equally bad day and you have to duck, dodge, dip, dive, and dodge just to make it through till lunch.
3. You have to do all your professional development
Like everyone else, I lamented those HR emails about required training and professional development. Now I kind of miss them.
As a freelancer, we’re doing it all and we’re doing it live. That means if you want to learn something, you have to identify how it connects to your work and then you have to balance it on top of your other business (client and admin) requirements.
It’s… tiring. There are many days I wish someone would tell me I’m off the hook for work one day cause I have to attend a mandatory course. But alas, no, I chose “freedom” (ugh).
4. No PTO
You want to take time off? Figure it out.
It’s that irritating and that simple. Sure, technically you have unlimited vacation now! But we already know that unlimited vacation is a trap.
And then there’s all the guilt! Oh, that two week vacation you took? Hmm, shouldn’t it have only been a week so you could focus on your clients more? Do you even care about them? Do you even want to be successful?
(Anyone else’s internal dialogue go to that place sometimes, or just mine?)
The way I personally get around this, if you’re curious, is switching my “identity hat.” I often say freelancers have to manage three identities: a CEO who wants growth, an individual contributor who wants to get shit done, and a person who has to handle the other two identities.
Source: Me! Credit me if you share it, please.
By switching from my IC hat to my CEO hat, I can see more clearly that rest is a good thing. Plus I get to feel good because my “boss self” isn’t being such an a**hole to my “employee self.”
5. Managing your own business admin
Lordy lordy, you really don’t know how much admin goes into running a business until you have to do all of it yourself, eh?
Thankfully, you can delegate. Unfortunately, that doesn’t mean you don’t have to manage the process but at least you can section off the work.
Here’s what I do: My VA handles financial admin (creating invoices and basic bookkeeping) and my accountant handles taxes. Right now, I manage all client admin, but that might change in the future.
There is no easy path
I really like the phrase “choose your difficult” in times like this.
Yes, I kind of complained a bit in this post about what I consider to be the worst things about freelancing. But… they are the worst on a comparative basis, not because they are actually all the bad. They require some getting used to, but as they say, it’s the worst thing in the world, except the alternative.
And hey–if you can handle the worst days of something and honestly think “that wasn’t so bad,” then you’re better off than most. You might have even just found your life’s work.
