What No One Tells You About Freelancing

I took a leap of faith to self-employment almost 18 months ago in March 2020. Yes, going into a seemingly unending global pandemic wasn’t the ideal time for a career transition, especially into a realm where I had no experience and no connections.

But timing aside, I’ve really built something over the past 18 months and am now a moderately successful freelance writer and personal trainer. I’m 100% self-employed with an extremely flexible schedule, and more days than not, I am in love with what I do.

So you might think I’m a little bit crazy when I tell you that I’m considering going back to full-time employment. But hear me out.

While there are so many incredible perks to working for myself, there are also quite a few downsides to the self-employment game, especially for someone in their early 30s that’s in the prime of earning potential and investing years.

In this article, I’ll cover:

• The pros and cons of self-employment
• The pros and cons of full-time employment
• Why I’m considering making the switch

The Joys of Self-employment

A few years ago, I had a conversation with a co-worker. She asked if I ever thought I’d start a business. Without missing a beat, I said, “Absolutely not. That’s so much stress and I don’t think I can handle it.”

Isn’t life funny? Not even a year later, I was entertaining the idea of trying to make my way as a freelance writer. And throughout the process, I’ve gained a new respect for people who start businesses, from the Silicon Valley start-up to the local mom-and-pop restaurant.

Self-employment has been a heck of a journey, with many ups and downs along the way.

Pros of Working for Yourself

• I make my own schedule. This is probably the number one thing people will call out as a perk when I tell them I’m self-employed. “Oh how nice that you can make your own schedule.” Yes, undoubtedly, this is a major perk. But just because I’m self-employed doesn’t mean I don’t have to work. I just get more flexibility to do it when and where I want, not in a specific office 9-5 Monday through Friday.
• I get to choose the jobs I do. It certainly didn’t feel this way in the beginning, and it won’t be the same for people in other lines of work. But I am now at a point where I can pick and choose which writing jobs I want. I get to gauge things like hourly rate, topics, and how much I connect with the client. I’ve established relationships and genuinely look forward to working with the client base I have.
• I get to learn all the things. Whether I want to or not, all of the learning and education that happens on the job is on me. If I need to learn a new software program or a new writing style, I don’t have co-workers to turn to that have vast experience. This means every day is exciting and has the potential to go in a whole different direction than I ever saw coming.
• I can write off work-related expenses. Some people mistakenly believe that being self-employed means I get to avoid taxes entirely. And while I can write off software platforms I use or the coffee I buy when I meet with a client, it doesn’t mean I’m not paying my fair share when tax time rolls around.

Cons of Being Your Own Boss

• If I’m not working, I’m not earning. If I’m not feeling well or want to take a couple of days off, my job and, therefore, my income shuts down. It turns out vacation is a lot more fun when you know you’re still earning income while you’re gone.
• I don’t have benefits or a retirement match. Benefits are such an overlooked aspect of full-time employment. In a job negotiation, many people look at a salary to indicate what the role is worth. But what I’ve learned is that benefits are worth so much more. And since I’m self employed, the only benefits I receive, like insurance or retirement options, are the ones I provide and give to myself.
• Income is inconsistent. I might pay myself this week and then not again for 3 weeks because I didn’t have enough work come in. My income still varies wildly, and I can’t depend on paying myself a steady paycheck every month.
• Everyone else seems to be working. I’ve heard this before from adults who retired a few years before their friends. They have all this free time during the week, but no one to spend it with. As I’ve grown comfortable in self-employment, I find that I’ve formed relationships with others that have flexible schedules, like some ladies from church and stay-at-home moms in my neighborhood. But just because I’m flexible, doesn’t mean the rest of the world is, so finding time to do things I love, or the people to do those things with, can be a challenge.
• No co-workers. Now there are definitely days when I’ve felt this is more of a pro than a con, especially when I think about some of the drama I had to deal with in previous jobs. But sometimes, my furry co-workers just can’t provide the same water cooler banter. I do genuinely miss having relationships with people and going out for a drink with co-workers from time to time. Did I mention we self-employed folks have to throw our own holiday parties? Lame.

How Full-time Employment Stacks Up

I was all too happy to leave the grip of my last employer and venture out into something new. But as I now turn my focus on potentially working for someone else again, I see both the things I ran away from initially but also the bright sides.

Pros of Working for Someone

• Consistency and reliability. I kind of forget what it’s like to get a paycheck on a regular cadence. But when I dream about it now, it feels very reassuring.
• Clear expectations. If your company is well-established, you know roughly what each day will bring. And you can fall into a comfortable cadence, working each day within the bounds of your nicely defined role.
• There’s a well-defined path to promotion. Many companies have a pretty clearly defined path for your next step. For example, I once started at a company taking phone calls in member services. And I knew that the next role was to move to the analysis team, then to become a team lead. It was set in stone, and it left me with a clear goal to work toward.
• Professional development opportunities. Previously, every company I’ve worked for has been willing to pay for job-related coursework, certifications, or conferences. It’s not until you look at paying for those on your own that you realize just how much it costs. Sure, I could go to a writing conference, but it may end up costing thousands out of my own pocket to do so.

Cons of Full Time Employment

• You’re at the mercy of your employer. It goes without saying that I can pretty much do what I want when I’m running the show. If I want to wake up at 5 and work until 8 and go back to bed, I can do that. If I want to take a Thursday off to get out and paddleboard and work Saturday morning instead, I don’t think twice about it. But when you work for a company, there’s an expectation that you’ll be available during certain working hours. That allows for a lot less flexibility to do whatever you want. It also may mean a company decides they don’t need your services anymore, leaving you with years of working experience, and very little to show for it.
• Your earning potential depends on those above you. As a freelancer, I set my own rates. So if I realize one day that the work I’m doing is not on par with the pay I’m getting in return, I can ask my client for more money or find others who are willing to pay more. When you work full-time, you may only have the option of a raise once per year or when someone in a position above you leaves. And whether you get a raise and how much will depend on how your manager or supervisor thinks of your performance.

Building a Case for Switching From Self-employment to Full-time

1. It makes financial sense.

I’ll be the first to admit that my decision to start looking for full-time employment is primarily financial. And yes, you may say “money isn’t everything” or “do what makes you happy.” But I once heard that it’s more comfortable to cry in a BMW than on a bicycle.

And while I think I’m the kind of person who can be happy doing just about anything, I believe there are financial goals that will be easier to achieve with the cushion of a stable salary. I’d love nothing more than to be able to max out my HSA, 401(k), Roth, and have money left over to live my life. But with 2 out of 3 of those accounts completely off the table with self-employment, I’m having to get more creative with how I save.

2. I miss guidance, mentors, and others pushing me to be better.

I’m definitely the kind of person who is intrinsically (read: internally) motivated. Otherwise, I wouldn’t get up every day and do the work I do. But I’ve worked under some amazing managers and mentors in the past who encouraged me to pursue new paths I hadn’t considered. And I miss being accountable to a team who holds me to a higher standard than I might hold myself.

3. Remote-only companies mean I don’t need to sacrifice the home office.

My last job required me to be in the office most days of the week, and I dreaded my daily commute. Now that many companies are remote-only and with so many options to work at remote-first companies, I don’t need to sacrifice my sweet home office set up to go to a dingy, poorly lit office building anymore.

The Bottom Line

If you’re self-employed and looking to transition to full-time employment, like me, the decision depends on a lot of factors. So before you decide to make a life-changing move like this, consider:

• The financial implications. Think about things like your current income, benefits, savings vehicles, and potential future income.
• Whether you’re ready to put control of your work back into another’s hands. This is one I’m particularly concerned about, will I be ready to relinquish control to a stranger?
• If you see more growth working for yourself or alongside a team. Is there potential for you to expand your business and your personal development working alone? Or do you thrive more in a team environment?

I don’t know quite yet what the next few months will bring. And I can’t firmly say whether I’ll be back to full-time work this year. But what I do know is I’ve put a lot of thought into it, and whatever I decide, I’m not making this decision lightly. And as you too think about your future earnings and growth, it’s a decision that you shouldn’t take lightly, either.

Keep Reading:

• How To Get A $5,000 Raise At Work In 15 Minutes
• 6 Steps to Start Making Money as a Freelance Writer
• What You Need to Do If Your Employer Does Not Offer You A 401k Plan