All the Reasons I Love the Freelance Lifestyle — And Some Hard Truths

It's no secret that I love my freelance lifestyle. But it's not always easy, and sometimes I get annoyed with the whole thing. Let's take a look at all the pros … and the cons.

When potential freelancers approach me, asking for advice on getting started with freelancing, they often do so because they've seen my posts on social media. My Instagram is full of images of my travels and other activities. They want to know how they can have that life, too.

The freelance lifestyle is one that I've enjoyed for almost two decades. What it looks like has changed over the years, but one thing remains the same: I love the freedom and flexibility.

So, as I reflect on another year of freelancing — and consider what I'm grateful for — I've been thinking about what the freelance lifestyle means to me. But reflection also comes with a hefty dose of caution. Before you decide to go all in, make sure you understand that freelancing has some definite drawbacks.

Why I love the freelance lifestyle

Let's start with the good stuff. Even on days when I just don't want to, I usually conclude that the freelance lifestyle is totally worth it. Here's why.

I set my own schedule.

This is one of the biggest advantages of freelancing. For the most part, you set your own schedule. My schedule has evolved over time, but it always reflects my personal priorities and values.

When my son was younger, the freelance lifestyle was about being there for him. I could get him off to school and be available if he was sick. Today, my freelance lifestyle focuses more on being able to get up when I want. Without an alarm. It's about exercising in the middle of the day and being able to meet friends for lunch.

The flexibility in my schedule is a big deal. I can go to the spa during the week when it's less busy. Travel during “off-peak” times when it's less expensive. And all of this happens because my freelance lifestyle is so flexible.

Clients can't tell me when to work or be available. I just have to meet a deadline — a deadline I agree to.

I can work from anywhere.

No going into an office for me. Often, my client work is completed while I sit on my bed. (After I've had a cup of Crio Bru and practiced yoga.)

If I feel like a change of scene, I can take my laptop out to the swingy chair in my front room. Or I can go downtown and complete projects from my favorite wine bar. A nice bottle of red and a charcuterie tray can usually get me through a project. Or help me tackle my emails.

Often, I work while I travel. The freelance lifestyle allows me to travel slowly. I can spend enough time in a place to work in the morning and have the rest of the day free. I love solo travel, and freelancing provides me with the freedom to go where I want. As long as I can access the internet, I can accomplish tasks.

Plus, freelancing allows me to live in a low-cost-of-living area and be comfortable. None of my clients are in my local area. And it doesn't matter because I can do this from anywhere.

I choose my clients.

In the beginning, I had to take what I could get. Today, though, I'm much pickier. While I still have some boring clients, they at least pay well. I can turn it down if a project is too much of a hassle. If I don't like the business practices, I don't have to take the work. After building up a reputation and a client base, you can begin to fire the clients that aren't serving you.

Additionally, as you become a better freelancer, you can cycle out your lower-paying clients in favor of those that pay better.

With the freelance lifestyle, I can prioritize clients that aren't difficult to deal with and that offer interesting work. At the very least, I can choose clients that pay well or give me some leeway in my schedule.

Few jobs pay as well for the time spent as freelancing.

It's not always easy. And getting started takes effort. Sometimes I'm bored. But the other day, I spoke with a good friend, a fellow freelancer.

“Sometimes what I do is unfulfilling, and I'd like to do something else,” he said. “But I look around. What other job could I do that offers this much freedom and flexibility and pays this well?”

Many writers, when they start, don't get paid well. I remember writing 300-word catalog descriptions for $5 and $10 a pop. But today my rates are much higher. It's not uncommon for me to receive $400 for a 1,000-word article that requires little research. Interviewed articles and longer articles pay higher rates — sometimes as much as $1 per word. I can be paid up to $2 per word when I provide press releases or email marketing copy.

In some cases, I've been paid even more.

While the effort is there, the amount of time I spend for the amount of money I am paid is very good. How many “real” jobs allow you to work part-time hours while making six figures a year?

Freelancing subsidizes my nonprofit efforts.

One of the best things about the freelance lifestyle is how it subsidizes my more purposeful pursuits.

Unfortunately, our system isn't set up for mass participation and engagement. Many people who want to be more involved in local causes and politics are stuck. They have to work (sometimes multiple jobs) to survive. The kids need help with homework and getting to their activities. There's little time for other pursuits.

Because freelancing pays well and offers flexibility, I can focus on doing good in my corner of the world. There's time to volunteer on local nonprofit boards that address affordable housing, early childhood education, and food insecurity. I'm involved in civic organizations. I participate in local politics.

Unfortunately, my level of engagement is a privilege in our current society and system. It would be great if our systems were set up to support people and encourage them to participate. The freelance lifestyle allows me the ability to begin advocating for change on my home turf.

(I recently updated my book on becoming an online freelance writer. If you decide you want to give it a try, you can get the 2nd edition, which is almost double the size of the 1st edition.)

Downsides to freelancing

While I love the freelance lifestyle and wouldn't give it up, it's not all unicorns and rainbows. If you want to join the ranks of freelancers, it's important to understand what you're getting into — especially at the beginning. Here's what you need to consider before you go all-in on freelancing.

It takes time to build your ideal freelance lifestyle.

Building your freelance lifestyle isn't an overnight endeavor. I've been doing this for almost 20 years. I'm in a place that allows a lot of flexibility and freedom, but it took time.

It took years to reach the point where I made six figures a year. Additionally, over time, what your ideal schedule looks like is likely to change. I've had to reinvent my life and my approach several times.

I can charge as much as I do because I spent years building a reputation. Today, I spend less than 20 hours per week on client work, but sometimes I worked 50 or 60 hours a week in the early days. And I had to do it early in the morning or late at night, depending on my son's schedule and what was happening with my then-husband.

While I've seen some people take the leap and see success in a few months after they start freelancing, for the most part, you need to be ready to put in time and effort — sometimes a lot of time and effort — at the beginning.

You don't have the same safety nets.

There are risks to having a traditional full-time job. If you're laid off, you instantly lose that income. With freelancing, you have more diversity of income. When one client falls through, you still have other income while you look for a replacement.

However, freelancing doesn't come with some of the perks of regular white-collar employment:

  • Regular, predictable income in the form of a paycheck.
  • Employer-subsidized health insurance.
  • Paid vacation time.
  • Paid sick leave.
  • An employer-provided retirement plan (and potential match).
  • Other perks might come, depending on your job, such as help with transportation and childcare costs.

Instead, you need to devise a way to create your benefits package. I buy my insurance on the exchange and set up a SEP IRA. I make automatic investments. When I want to take time off, I have to plan for that in my schedule. I've set up an S Corp. and payroll, but in the beginning, you might not have that income stability as a freelancer.

You need to weigh the risks to see what matters to you and which you tolerate better.

If you don't work, you don't get paid.

While I often work while I travel, there I times I really want true time off. When that happens, I have to make arrangements:

  • I might need to work ahead, cramming in as much as possible before leaving.
  • All my editors need to know my plans and when I'll be in contact again.
  • I need to make sure I have systems in place to manage my bills and ensure that I have available money.
  • When I'm sick, I either need to power through or talk to my editors about an extension.

I usually go camping a couple of times a year, and I spend days without the internet. When that happens, I have to plan ahead. How will I keep my income? Or will I need to dip into my reserves? This can lead to doubling up for weeks ahead of time or accepting that I will have to play catch-up when I get back.

It can be stressful to know you won't get paid time off for vacation or health reasons. I've decided that it's worth it to me. Even though it means I must work when I travel sometimes or work extra when I've been sick, the freelance lifestyle is still worth it. But it's not worth it for everyone, and you need to be honest about it with yourself.

One of the things I'm working on, though, is creating recurring revenue streams. I want to be able to continue making money, even if I'm not actively involved in writing. Developing these revenue streams is tricky, though. As a freelancer, I'm paid for my work almost immediately. I invoice for my work, I get paid. Building up recurring revenue is harder. I don't get paid immediately. I have to market. But I recognize the importance of attempting these other income streams.

Some of the work is boring AF.

A lot of online content creation is boring. You have to write to search engines. You're given an outline. Sometimes you write similar things over and over. It gets tedious.

I refer to myself as a “jobbing writer.” I do stuff because it's my job as a freelancer. Writing high-minded treatises isn't something I get paid for. Sometimes the things I'm interested in aren't assigned to me. Instead, my clients make assignments based on what they see in SEM Rush and what brings in the money.

While I have some control — I don't often accept review assignments — the reality is that most of what I get paid for is just … uninspiring. My inspiration and purpose come from passion projects that might not yield instant pay. Some of my passion projects are barely profitable.

I do the boring, uninspiring work — sometimes writing drivel — so that I have the freedom and flexibility to find meaning in other areas of my life. Accepting this is part of the deal if you want to make money as a writer. I might be a sellout, but I'm a sellout who uses that money to fund all the other parts of my life that I enjoy.

There's no guarantee freelancing will work out.

Sure, there's no guarantee with “real” jobs and traditional career paths. But there are also some bigger risks with freelancing. You could quit your job and discover that you don't like freelancing. There's a lot of pitching, rejection, and scrambling for work — especially in the beginning.

There's no guarantee that all of that work will ultimately pay off. You could spend months trying to build a client base and get nowhere. Or, you might discover that it's too stressful to deal with the uncertainty.

The conditions that led to my freelance success include:

  • My then-husband was working on his Ph.D., and we took student loans to help us live while I built a freelance client base and stayed home with our son.
  • It was early in our marriage, and we only had one young child. The expenses and pressures that come with older children and an entrenched lifestyle weren't an issue. We were already “poor” college students, so we didn't need to make significant changes.
  • Online content marketing was in its infancy. It was relatively easy to break in as a trained writer with a master's degree in journalism.
  • I had access to a low cost of living and inexpensive childcare to allow me the ability to cover costs with minimal earnings.
  • We had access to resources, such as taking no-interest loans from our parents to help smooth our budget and help with financial emergencies.

While I certainly worked hard, some circumstances made the shift to freelancing easier. One of the biggest ones was that I went straight from grad school to freelancing. My meager earnings were an upgrade from the fact that we had no income for two years before I started freelancing.

Not everyone has these circumstances. There's no guarantee that leaving your job, making sacrifices, and changing your lifestyle for months while you build your freelancing career will pan out.

The freelance lifestyle: bottom line

My freelance lifestyle is worth it to me. A combination of writing skills, hard work, and luck has allowed me to build a life that I love. It's full of freedom and flexibility. It's not always perfect. Some aspects get annoying. But, overall, it's been worth it to me.

Whenever I get annoyed about yet another insurance keyword article, I remind myself that it will be over in an hour — and I'll have made $400 or $500. Recently, when visiting L.A., I got up, wrote an article I hated writing, and then met my friend for a bike ride along The Strand. After an hour of annoyance, I was rewarded with the rest of the day to enjoy myself.

I can get up and write an uninspiring credit card review and then attend a nonprofit board meeting that offers me the chance to directly impact others' lives for good by making the Soup Kitchen more accessible and stable for its clients.

I have yet to find another occupation that provides this level of freedom and flexibility. So I cherish the freelance lifestyle and do what I can to remain relevant in my field. Ultimately, it's my best option for designing a life that I enjoy and that offers me the ability to pursue my passions and purpose.

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