Mythbusting the Freelancing Life

Mythbusting the Freelancing Life

It's not always a day at the beach... unless it is.

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For someone who works full time either in an office or remotely, freelancing can sound like a dream. Get up whenever you want? No boss handing you tasks or looking over your shoulder to make sure you're not just on twitter? Shop for shoes at 2:00 pm on a Wednesday? No pointless Zoom meetings? It sounds like paradise.

Yes, freelancing can be all those things. The reality is that while those things do happen, it's not all a tasty ice cream sundae. Like many things, the truth lies somewhere in the middle.

For years, people have peppered me with questions about freelancing. I've been doing it for 13 years now. In that time I've dispelled a lot of myths and dissuaded a lot of super smart, hard working people from going freelance. If you've ever dreamed about going solo, I want to bust some myths about the freelance life. Let's get into it!

Myth 1: Setting your own schedule

Okay, yes. For the most part, you're in charge of your time. The alarm clock no longer rules your life. That's probably the biggest perk to going freelance. You can hit the gym at any time of day or have coffee with a friend whenever you want. Even the experience of doing simple errands is completely different. Picking up groceries at 2:00 pm instead of battling traffic after the workday is a dream.

Here's the flip side.

If you land a great client and they happen to be in a different time zone, you may need to adjust your schedule to accommodate their needs. Or consider that in the 11th hour of a deadline, your client suddenly remembers a feature or some content they wanted to include. There go your Friday night plans and your weekend with the kids.

Freelancing is a business. It's your business. While no one is there to tell you when to be at the office, also there's no one to pick up the slack when you get sick or just want to chill.

Myth 2: No boss hassling you all day

This is true. No one is lurking over your shoulder with their stinky lunch breath making sure you're on task. There's no one popping up on Zoom to "check in." That's all over.

The thing is, the person you used to call Boss is now called Client. And while clients don't have actual authority over you, they can sometimes be as (if not more) annoying than a boss. Most of my clients have been wonderful, but there have been those needy ones who literally took over my life. From those people, get ready to handle constant emails and texts, needing updates on projects where the deadline is still weeks away.

It can be tempting to tell those clients to F**k off, but just as if you said that to your boss, your paycheck will disappear along with the client.

Myth 3: Pointless meetings are over

Oh, if this were true. I have a particular aversion to Zoom meetings. I think I have an actual video meeting allergy.

If you work in an office, you probably attend a lot meetings that could have been a Slack message. Those meetings are over. Yay!

What takes their place are new kinds of meetings. A prospective client will want to do a Zoom call or meet for coffee just to see what you're like. Or, in the middle of a project, they'll want to meet just to "get some new ideas across." Sometimes they just want to talk, and you're the closest person available. Welcome to being a therapist.

The other new kinds of meetings are networking. It's Meetups on Zoom to get established in your industry. It's being present on a particular Discord server or showing up in forums to help people out. I'll be honest, I'm not a fan of networking myself. But I know that those kinds of meetings help establish me as a pro and help build my business.

Myth 4: You can spend the day at the beach

Well, of course you can. No one is stopping you. Don't forget that now you're in charge. Except that now you need to consider that if no one is working in your freelance business, no one is making any money.

Just today (Wednesday), I took my family to the beach after breakfast (which is what prompted this post). We spent a couple hours there and headed home. While it was fun and I have no regrets, I also worked a full day after that. I'm also prepared to work on the weekend to make up for any lag in my productivity. That's just how it works. At the same time, I wouldn't dare go to the beach on a summer weekend, so it works out for me.

Myth 5: The money is better

It can be, if you do it well. But guess who's now in charge of paying the IRS (before you file your annual return) and handling your health care plan? That's right. It's you. Even if you manage to bring in what you were making full time, the cost of doing business adds up fast. So you need to be prepared to make a lot more than you were making before.

Also, you are now the entire Marketing and Sales team. If you don't hustle, you don't get clients and you don't get paid. You're going to have to get good at meeting new people. You're going to have to be okay with "interviewing" for new jobs frequently.

The money can be better. It also comes in waves. You could snag a high-paying gig that lasts three months, and then hear crickets chirping for the next two. To keep paying your bills on time, you'll need to get creative. It can be tempting to buy a new laptop when you get a windfall client, but when times are tough you can't eat the laptop for dinner. Good budgeting and delaying gratification are crucial to your success. You may also need to diversify your income by taking on other types of gigs that are easier to come by. They may pay less, but when things are slow, you'll at least be bring in some cash.

Alternatives that feel like freelancing

I hope I haven't put you completely off your freelancing dream (don't worry, that's coming up). It may not be the right thing for you, and that is completely okay. Knowing that about yourself is empowering.

There may be some alternatives you can consider to get some of those freelance perks.


First, take some time to think about your job and the company you work for. Is it as bad as all that? Maybe it is, I don't know. I've had some pretty bad jobs in my life. Consider that another department might be a better fit for you. Or if you hate your boss, maybe you can talk to their boss and see if you can transfer.

Remote work

A lot of people have been working remotely during the pandemic. If you want to keep that going, maybe you can negotiate for that, or at least a few days per week. A lot of companies are forcing people back to the office, so that may not work out. Maybe it's time to look for a different company?

Flex hours

If you have to be in the office, do you really need to be chained to your desk for eight hours? Maybe you can work out a schedule where you come in earlier or leave later. If you can be there during peak times when someone may need to see you in person, you may be able to work out a flex schedule.

None of this stuff is easy to ask for and it's not guaranteed to happen. But if you don't ask, you don't get.

Don't quit your job!

If you haven't quit your job yet, don't. Dip your toe in the freelancing waters by taking on side projects while still employed. Work your way up to the point where you're confident you're going to have steady work.

If you're thinking No way! There's no time in my day to do "side projects!" WTF? then I'm sorry to break the news, but freelancing is not going to work for you. You're not going to work less or even the same when you quit your full time job, you're going to work longer and harder than you ever have. So if you're not ready to take on extra, then you're not ready for freelancing.

If that didn't dissuade you, than I say go for it. Going solo has a lot of perks and it can be a great life. If you want to explore it, make sure you go in with your eyes wide open.

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