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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
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.
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.
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.