10 Things No One Wants to Admit about Being a Freelancer

Hira Saeed recently published an article about the risks and rewards of being a freelancer. I highly recommend reading that article before you read this one. Click here to open in a new tab.

Spoiler alert: she reached the conclusion that the freedom and flexibility that comes with the freelance lifestyle are worth the sacrifices and frustration that come along for the ride. For fun, I decided to write an article from the opposite perspective. Below are ten things no one wants to admit about being a freelancer (self included).

1. You’ll get lonely.

The co-workers you used to call “chatty” will seem more appealing after you spend enough time working alone in silence. If you choose to become a freelancer, you must compensate for it by fostering your personal relationships at a higher level. Otherwise, misery will quickly follow. Community and connection are essential ingredients of a happy life. Ignore this advice at your own peril.  

2. Most clients are awful.

Some clients are too controlling. Even though you’ve been a writer for five years and they’ve never written anything beyond a journal entry, they’ll act as if they actually have a clue. Fail to listen to every word they say — even the misguided ones that reduce the quality of your work — and they’ll complain. Other clients won’t provide any guidance and expect you to just know what they want (because you’re a psychic… apparently).

3. There will be slow months.

When you have a “real” job, there’s no worrying about money. You know the exact amount of cash you will receive and when to expect it. The bills get paid. Your lights stay on. You get fed. No problem! That changes when you’re a freelancer. You might be rolling in money one month and panicking about a lack of sales the next month. No matter how good you get at conversions, this will happen… so I suggest you have a big nest-egg!

4. You might even get “ghosted.”

The traditional rules of work don’t apply to freelancing. When you’re working with a company, they can’t fire you out of the blue. There must be a just cause. They have to provide you with a heads-up. Failing to follow these rules would get them in trouble with the government. Freelancers don’t have that luxury. Once, I had a column on a corporate wellness website, and the client just stopped answering my emails without warning. Talk about stressful!

5. Wannabe clients are the worst.

I can’t — and don’t want to — think about how much time I’ve wasted on wannabe clients. You sit and discuss the specifics of their project for HOURS. Together, you create a solid strategy that would rake in money for their business. This consultation process continues for days, weeks, or months. And despite the amount of time and attention you devote to them, they never hire you. They might even steal your ideas and attempt to implement themselves (often poorly).

6. People HATE spending money.

The majority of people are talkers, not doers. They’ll act like you’re God’s gift to business in the consultation stage. But as soon as you discuss exchanging funds, they’ll look at you like a leper. Good luck convincing a cheap wannabe client to invest in your freelancing service. You might as well try convincing a dog person to adopt a cat. To save trouble, only pitch your services to people who already have a successful business and solid sales funnel. Others can’t be trusted.

7. You’ll miss having benefits fast.

It’s easy to say, “I can live without paid time off, insurance, and a 401K,” in the early stages of your freelancing career. A few months (or years) later, that thought could turn into, “What the hell was I thinking?” Those benefits make even the most boring day job seem more appealing. I’m not going to lie to you. I really miss being able to take holidays off and knowing that I would be paid, even though I was off work and spending time with my loved ones. This is a large part of why I’m abandoning ship.

8. Your tax situation will be horrible.

Tax time is great when you have a traditional job. Yeah, government spooks steal a certain amount of money from your paychecks, but they give it back in a lump sum the following year. Suddenly, you have a few thousand dollars. You could start an emergency savings account, invest in a down payment for a new car, take your lover on an exotic vacation, or do whatever. Tax time sucks for freelancers. Now you are the one giving those spooks a few thousand bucks. Is it worth it? I used to think so, but now I don’t.

9. Motivating yourself to work is hard.

“I’m my own boss!” That’s a great philosophy when you’re self-aware enough to regulate your emotions and force yourself to be productive, regardless of your feelings. Sadly, most people lack these skills, and their crappy productivity proves it. Most people are ruled by their emotions. That’s not so bad when you have a manager who can motivate you to push through that stuff. It’s really bad when you’re your own manager (and have no clue how to regulate yourself).

10. Sales skills are more important than your craft.

It doesn’t matter how amazing you are at writing, photography, web design, or whatever your art or craft might be. You might believe, “My work speaks for itself!” False. You have to speak for it in a highly persuasive way in order to close sales. And if you can’t close sales, you shouldn’t be running a freelance business. You’d be better off working a traditional job in which you can apply your skills for an employer that provides benefits and a predictable income. It’s harsh, but true!

This is the last article you’ll see by me that discusses freelancing.

Due to the reasoning above, I’m choosing to refocus on finding a “real” marketing job. I am handing the reins of my freelancing 101 column to Hira Saeed, who will keep this train rolling in my absence. But don’t despair! You’ll still get to enjoy content about mindset, motivation, and other topics by yours truly.

Know a friend who needs a reality check? Go ahead and share this article on social media. :)

Read More Articles by Daniel Wallen:

Click to comment

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

To Top