Realities of Freelancing: What You Need to Know

Freelancing is big business. Today, there are 53 million people doing freelance work in the US alone. Freelancers make up 34% of the national workforce! But there are a lot of realities of freelancing that aren’t always talked about.

These are the cold, hard realities of freelance work. And they’re not always pretty.

I hate to break it to you, but freelancing isn’t a big pajama party and paid work vacation.

Anyone who talks about the “4-hour workweek” or the “digital nomad lifestyle” is trying to sell you something. These are myths by people who either:

Have a trust fund
Worked a $100k+ job to save money for years
Are supported by a spouse/partner/family member
Live in a low cost-of-living country

With so many people choosing to ditch their 9-5 gigs to tread out on the entrepreneur path, it’s important to recognize the realities of freelancing and how it isn’t always sunshine and rainbows. It’s definitely not for everyone.

Don’t get me wrong, I love working as a full-time freelancer. I get to do what I love every day, and I get the freedom to work from home online. These are great things that really suit me! However, I’d be lying if I said I wasn’t frustrated by the freelance lifestyle and all it brings.

I recorded a podcast on this exact topic that explains all of these things below in my own words, so listen below or anywhere you find podcasts.

What is Freelancing Really Like?

I can only talk about my own experience, what I’ve read online, and my friends’ experience working online. I started working online in college, and I’ve been freelancing for several years.

Freelancing is really hard. That mostly sums it up.

There are a lot of added stressors you don’t always think about like isolation, the feast vs. famine of working with clients, and the added paperwork. It’s stressful! Plus, working where you live is really hard. There’s a huge learning curve, and I can see why it would tire people out very quickly. Heck, I’m tired too!

Now, let’s breakdown the realities of freelancing. Prepare yourself for the cold, hard truth!

1. It’s All On You

When you’re a freelancer, you’re on your own both physically and mentally. There’s nobody to talk to during the day, nobody to ask for help, and clients are often unavailable.

While many clients will help walk you through things or answer questions, getting ahold of them can be a challenge. This depends on the client, of course, but I’ve had clients go silent for weeks on end when all I needed was a simple question answered.

You’ll be on the hook for a lot of decisions, and you’ll also need to learn how to be resourceful on your own.

2. You’re Always Chasing Clients

Clients are easily the worst part of working as a freelancer. This doesn’t mean that I don’t love the work I do or most of the clients I work with. It does mean that figuring out complex projects, coordinating deadlines, and communicating online isn’t easy. It’s the nature of the freelancing landscape!

You’ll chase clients for new work, project questions, and getting paid. You’ll need to have a freelancing contract in place for each client, and it’s on you to enforce it.

At the end of the day, it’s on you to protect yourself, your business, and your work. Nobody will do the fighting for you. That’s a big burden to carry!

(Pro tip: snag my freelancer contract template below to simplify your client relationships and protect yourself!)

3. It’s Easy to Undersell Yourself

I’m the worst at underselling myself. It definitely comes down to my crippling case of imposter syndrome.

Knowing your worth doesn’t always come naturally. You don’t’ have a set-in-stone job description to fall back on, and a lot of your experience will be smaller or one-off projects. How do you sell yourself and know your worth?

You have to set your own rates as a freelancer. You have to negotiate a higher freelancer pay, and you need to stand your ground. This also means making hard decisions about when to negotiate and when to stay firm. Much of this you’ll simply need to learn as you go!

4. You Can’t Be a People Pleaser

I’m a self-proclaimed people pleaser. I like people to like me. It’s a curse!

If you want to be a successful freelancer, you simply can’t be a people pleaser. There’s another word for this type of person in the freelancer community: pushover.

You can’t always say yes. You need to set boundaries and know when to distance yourself from problem clients.

This is something I am largely still learning. Since I’ve started, I’ve learned to set office hours, not to respond to messages/emails at night and on weekends, and to say no when something is outside of my comfort zone. It took me years to get to this point.

5. You’re Isolated

One of the most common reasons I hear for freelancers returning to a traditional job either full-time or part-time is the isolation.

Working from home as a freelancer is isolating. You’re alone most of the time, if not all of the time. Getting work done at home when there are always distractions isn’t easy, and thriving without anyone around you isn’t easy.

I’m naturally an introvert. I work best when I work alone. This helps me, but even I struggle with isolation.

Since I started freelancing after moving to a new city, it’s been very hard to make new friends. Where do you meet people if you’re not in an office or at school? It’s definitely a new challenge. Avoiding those isolated feelings when working from home is a must!

6. Burnout Is Real

About 3 months ago I experienced a major bout of burnout. I fired my most profitable client because they were demanding all of my time, expecting ridiculous delivery times, and didn’t respect my vacations. (See: don’t be a people pleaser!)

All of these things could have been avoided, but I simply didn’t know any better.

As a freelancer, you’re entirely responsible for your own income. If you’re not able to work, you’re not getting paid. This creates pressure to work ALL THE TIME. Taking time off leads to guilt, and it’s very hard to not feel “on” when you work online.

You have irregular hours, no real days “off,” you live where you work, and planning a vacation is difficult. All of these things are manageable if you set boundaries, but that still doesn’t make them easy.

7. Freelancers Do More

Welcome to freelancing where you feel like both an employee and a business owner all at once. As a freelancer, you’re now in charge of your business. This brings so many more responsibilities you might have never experienced in a usual working role. Here’s what I mean:

Taxes – You now have to pay your own taxes, including self-employment tax. You’re responsible for filing taxes on time (quarterly or yearly), and you’ll need to keep your tax earnings separate.
Sales – Unless you’re from a sales background, selling yourself and your skills probably isn’t something you’re familiar with. As a freelancer, you’re constantly pitching yourself and taking on a sales mentality.
Calls and meetings – As a freelancer, client calls and meetings are the new normal. You’ll need to be comfortable talking to strangers on the phone, knowing your stuff, and being available for these meetings.
Negotiating – You’ll also need to negotiate. You’ll be negotiating your pay, your time, your skills, etc.

Most of these things aren’t that common in a regular role unless you were an upper-level supervisor or business owner. There’s definitely a learning curve that comes along with figuring everything out for yourself.

The Cold, Hard Truth About Freelancing

Don’t get anything above misconstrued. I love freelancing. It’s my dream job.

But it’s also a job. And like any job, some parts of it suck.

I hope this post on the realities of freelancing helped put some things in perspective. Whether you’re looking to commiserate with a fellow freelancer or prepare yourself for a new role working online, this list was for you.

What realities of freelancing do you dread? What are your favorite? Let me know!