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The Freelance Lifestyle: What It Is, What It Is Not, and How to Enjoy it Fully


The Freelance Lifestyle

The freelance lifestyle. It’s a dream, right? Mostly gym time, cocktails at lunch, and a call here and there with clients, right?

Think again.

While we truly believe in the ability for anyone to live the freelance lifestyle they deserve, we also know that it’s not all rainbows and unicorns like it’s often made out to be.

Legiit is the freelance marketplace built by freelancers, for freelancers—after all. We know a thing or two about putting in the hard work to earn the life you want.

So in this post, we’ll look at what life is like for a freelancer, what it isn’t like, and some of the things you can do to make the most of it. Day in and day out.

What Is the Freelance Lifestyle?

Living the life of a freelancer means making a decision to be your own boss. But rather than shirking responsibility or avoid difficult work, you are actually seeking those things out.

You are saying to yourself “I don’t need a manager to tell me how to do my job. I’ve got the skills, the experience, and the integrity to do it on my own.”

In other words, living the freelance lifestyle means sacrificing the “easy route” of having someone else make all the tough decisions for you. Of course, this sacrifice comes with plenty of benefits too.

You can set your own hours.

You can overcome old income limits.

You can decide who you want to work for and what you want to do.

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All in all, freelancing provides you with the flexibility to have more control over the decisions that help you live the life you want to live. For example, maybe you aren’t limited to two weeks of paid vacation a year any more. Instead, you just know that if you want to take a month off, you just have to make the decisions that will lead you to the earnings that let you afford it.

What It Isn’t: Common Freelance Myths

So that’s a quick take on what living the life of a freelancer looks like. In a word: flexibility.

Next, let’s take a minute to dispel two of the most common myths about freelancing. Understanding what the freelance life is NOT will give us a better idea of what it IS.

Myth #1: Freelancing is easy.

If it was easy, everyone would do it.

While freelancing is probably the more flexible, more freeing route—very few people who actually do it would say that it is the easier route. There are a lot of reasons for this.

One of the most obvious is that freelancing is much less secure when you are just getting started. If you get hired for a salary position for a typical office job, you know exactly how much you’ll be making every paycheck. 

As a freelancer, though, you have to build up that revenue stream. A steady paycheck is not a guarantee from day one.

Myth #2: Freelancing is passive income.

For some reason, a lot of people have this image of the freelance life involving bare feet, sandy beaches, and drinks served with little umbrellas.

It’s true. Freelancing may afford you the opportunity to travel more than a standard job. But you still have to work for your money. In fact, you don’t get paid for the time you spend chit-chatting at the water cooler. 

You only get paid for results.

So if anything, freelancing is the exact opposite of passive income. Now, if you scale your business properly, you may eventually not be as involved in the day-to-day grunt work. But you are still going to be doing plenty of work to earn your living.

Tips for Enjoying the Freelance Lifestyle

Now that you know what freelancing is and is NOT, let’s look at some things you can do to make the most of it.

Don’t compare yourself (too much) to other people.

If you are going to be bold and different by adopting the life of a freelancer, just do it. Accept that you are on your own unique journey, and don’t worry about how it compares to others.

Don’t think you are inadequate because other freelancers are more successful than you. Don’t doubt your decision when your 9-to-5er friends aren’t struggling through the same challenges as you.

The only caveat to this tip is that you are allowed to compare yourself to your peers and competition if it is to determine how to improve your business. This sort of educational comparison is worlds apart from the down-on-yourself, disparaging type.

Surround yourself with freelancer friends.

Freelancing can be a lonely journey if you let it.

The best way to avoid this is to make friends with as many other freelancers as you can. This network will not only give you moral support, but it will also provide you with a springboard for ideas on how to grow yourself as an entrepreneur.

Local freelance meetups are a great place to start, but there are also plenty of online options for the digital nomad in you as well. The Legiit Facebook Group is full of like-minded freelancers who can understand the journey that you are embarking upon.

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Be prepared for normies to not understand what you do.

People have a natural tendency to fear the unknown. Unfortunately for freelancers, this means that a lot of your friends and family won’t be able to comprehend why you decided to strike out on your own.

Be prepared to respond to comments like these:

When are you going to get a real job?

Aren’t you worried about retirement?

You know, taxes are a lot tougher for the self-employed.

Just remember that you made your decision for a reason. Doubters and naysayers can come up with an endless list of risks and worries to nag you with. But none of them negate the reason that you decided to take up the freelance lifestyle.

Those are yours. So get out there and own them.

About the Author


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My name's Ish--college English professor by day, interstellar copywriter by night.

The written word is my one true love (don't tell my wife!). I've been a writer at heart since as early as I can remember, I've been teaching writing for nearly a decade, and I've been content manager of a blog for the college that I teach at for about five years. What's more, I was the lead writer and editor for a table top roleplaying game that raised more than $100,000 on Kickstarter (just Google "Open Legend RPG" and you'll see what I'm talking about).

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