The Freelancer “Freedom” Fallacy

The life of a freelancer can sound very romantic: you have the flexibility to make your own schedule, be your own boss, and work on many exciting and varied projects. Want to take a yoga class at 10am on a Thursday? Great! Need four days in the middle of the week to go speak at a conference in Montenegro? Sure, sign me up! I can definitely write that off on my taxes.

But when people tell me how nice it must be to have so much “freedom,” I wince. There are many reasons why I have felt less than free in the last eight years as a full-time freelancer, and I wanted to share some of those with you in case you’re considering freelance as a professional lifestyle.

The Hustle

If you’re in the lucky position of having so much work thrown at you that you’re turning down jobs, then congrats! But guess what, dollface? You’re in Feast Mode. There will come a time when the emails stop trickling in, and you start looking at your calendar with a questioning eye. Someone close to you (probably another freelancer) will knowingly shrug and say “Feast or famine, amirite?” So you gotta hustle!

This can mean a lot of different things depending on what industry you’re in, but it almost always involves cold-calling a lot of people and explaining to them why they want (no, need) your services. It’s humbling, and it’s exhausting, and you’ll be rejected more times than you can count. See below.

The Rejection

Oh, the rejection! Having your pitches and proposals gently declined (or worse, ghosted) is painful, even if you’ve learned to develop a thick skin and to learn from the experience.

I became increasingly frustrated with this in my particular line of work as a video host. I’d shoot a TV pilot, wait for weeks or months, and then be told that someone “at the network” had decided that they didn’t want to go in that direction, or that there was another show that was too similar for that slate. In that case, it’s not just the loss of months of work and your hopes — it’s knowing that some nameless, faceless entity sitting in a room somewhere is making choices that hugely affect your life, and you have no recourse whatsoever.

There’s No Such Thing As Paid Time Off (See also: The Hustle)

Remember that 10am yoga class? That just means the freelancer will be working until 10pm answering emails, working on their projects, and generally hustling. All of that flexibility just means there are fewer boundaries.

Look at this hustle, he’s dealmaking right now.

I’m really glad that many startups and corporations are committed to providing a good work / life balance, but it’s hard for that to exist for a freelancer when not hustling means not knowing where your next paycheck is going to come from. Oh, speaking of which…

Fuck You, Pay Me

This is my house motto! The reason being that many freelancers (myself included) sometimes find themselves being asked to provide free services in return for intangibles like “exposure,” or “networking potential.” Those are both good things, trust me. But they will not pay my mortgage.

You must learn to be very forthright when it comes to talking about money and how much you’re worth. If clients lowball you too frequently, suddenly that becomes your rate. Set your bar high, learn to negotiate, and don’t undersell yourself.

Once you have committed the project to paper and signed a contract, that almost never guarantees that the client will pay in reasonable amount of time. You can write “Net 30” on your invoice until the cows come home, but there will always be an issue with the accounts payable folks that your point of contact swears they’re on top of, and the check is in the mail, and so on. This makes things like budgeting and quarterly tax payments really fun to deal with.

Can’t Forget About Taxes

Your taxes are going to be a nightmare. Hope you love Quicken! Your binder of 1099-MISCs and expenses and deductions will be a hellscape that only the most insane and diabolical accountants will look upon with glee. As a self-employed person, you are being taxed not only as the employer, but also as the employee. If you are very lucky, you will somehow have way over paid and get a decent return. If you are unlucky, well… don’t be unlucky. Pay attention to that stuff. Please.

HAH I WISH

The freelancing lifestyle certainly has its appeal, especially when things are looking good. But after almost a decade of it, I’m tired, and I’ve lost the excitement for the work I’ve been doing. You can’t hustle for something you don’t love anymore.

People always seem to tell co-workers leaving corporate life how “brave” they are, for working on their passions and making a go of it, on their own. But working on your passions is the easy part!

I want to be brave in a different way, now. I want to be brave enough to say that maybe this lifestyle isn’t a good fit for me anymore, and that I’m ready to have a life where the majority of the work stops at 5pm on Friday, at least for two days. And then I can go to happy hour with my coworkers, and we can talk about all the cool projects we’re building, together.

That’s a different kind of freedom, and it sounds pretty good to me.


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