My Love/Hate Relationship with Self-Employment

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I always thought self-employment was good but she brings up some pretty good counterpoints.

In the past, I’ve worked as a contract employee, but typically it’s always been with the understanding that the work will be full-time and that the contract would be renewed at the end of the year.

This venture into online writing and blogging, though, has been a completely different experience. I find short-term work. I look for more short-term work. I balance multiple clients while still working remotely.

I’m nearly two years into running this business as my sole source of income (though the old day job has turned into an occasional side hustle,) and I’ve got a lot of mixed feelings about it.

A lot of times, when we read about how bloggers go full-time, it feels like they’ve won at something. They can show you how to start your own blog, too! And experience the freedom of not having to go into a stuffy 9-5!

While there are definitely some merits to all that, today I want to get real with you. I want to tell you my personal experiences with both the good and bad sides of self-employment. Will you want to leave your 9-5 at the end?


Maybe not.

What I Love About Self-Employment

I don’t want to be overly morose. There are a lot of good things about this gig, and I’m lucky I had it to fall back on. Here are some of the definite pros.

I write my own hours.

If my kid has therapy or I have to battle an insurance company over their healthcare coverage, getting “off” normal business hours to take care of it is no big deal. At all. I just have to make up the hours during nontraditional hours.

I enjoy the freedom of being able to work when I want and where I want. I can travel without worrying about getting approval for time off, and take a mental health day if I absolutely need it.

As a matter of fact, last week I had a week-long migraine. Sometimes medication was helping. Sometimes it wasn’t. I was a mess, and would have had to use seven sick days if I were working a traditional job.

I don’t know if anyone even offers that many sick days outside of unpaid FMLA leave.

Because I was able to work in the windows of relief, I was still able to meet deadlines and get my stuff done.

I work with who I want.

I have to make money, so I am accountable to clients for freelancing, and to my readers when I choose to take on advertisers.

But if someone’s a jerk, I can shut that relationship down. I can look for other people to pay me money if I don’t want to take theirs.

It’s super liberating to only work with people you think are awesome.

I mostly work in my PJs.

Which is fantastic. When I have to get dressed up in business casual, it’s kind of a big deal. Technology has saved my wardrobe so many dollars by allowing me to work in solace.

I get invited to do cool stuff.

As a blogger, I’ve had a lot of opportunities to do a lot of cool things. Just this year, I’ve taken my child to an awesome LEGO event, tried my hand at skiing in Banff, viewed the Stanley Cup IRL, visited NYC for a dynamic conference on innovation, and have had some cool experiences with the FinCon Pittsburgh group I coordinate.

None of that would have happened if I hadn’t started Femme Frugality all those years ago.

I get to interview cool people.

For this blog and for other publications I write for, I get to interview people who are really, really good at what they do. They’re smart, interesting and actually want to spend time to sit down and talk with me about all those things that make them smart and interesting. I don’t normally like talking on the phone, but doing these interviews is something I truly love about my job.

The Cons of Self-Employment

There are definitely some things I’m not into, though. Or at least, things that I thought would be great, but have downsides, too.

I work by myself in my PJs.

The things that make this job amazing also have their negatives. Sometimes I get lonely, if I’m being completely honest. It’s way harder to maintain a social life as a mom of young kids when I’m not forced to see coworkers or fellow students everyday as a part of my routine.

I know. Co-working spaces. I even know which one I’d go to. But I don’t have to budget it in, so my frugal self has a really hard time legitimizing the expense.

It’s a constant hustle.

I don’t have to work with people I don’t like, but it is a constant hustle to find the people that I do enjoy working with. Before I started this gig, I would have thought this part of the job would be zero problem for me. I’ve always been hypervigilant about my money, and hustling went right along with that.

But at a certain point, you just get burnt out. Not necessarily with the work. But with the constant pitching that’s involved in obtaining  that work.

That’s not just true for the freelance writing side of my business. It’s also true for the blog. While it’s great to have advertisers come to you, sometimes you have to go after that partnership idea that’s been living in your head.

In fact, some of my longest and most profitable relationships have happened this way, and they’ve happened that way because I know what’s good for my readers–what they like and what will actually help them. But in order to give that to you, I have to make others see that they need you, my readers, too.

The work? I love. The constant pitching so you have enough to pay the bills next month? I don’t mind it, but could do with a whole lot less of it.

You never know when you’re going to get paid.

You can set up a contract with penalties for late payment, but that doesn’t mean you’ll get your money in time. It just means you can legally enforce late payments for when the client does finally pay.

In the meantime, get ready to run around like a crazy person figuring out how to get your health insurance premiums paid this month.

No benefits.

Any benefit you used to get from an employer is at least two times as expensive–and you have to pay for it all yourself.

The same can be applied to taxes.

Without set hours, you’re always on.

I used to work after my kids went to bed. When I first started this blog, that’s the only time I had. When I made this my full-time gig, the hours started driving me mad.

I wasn’t enjoying time with my kids during the day the way I thought I would because I was so stressed out about everything that I still had to do after I tucked them in at night.

Owning your own business is a never-ending to-do list. You’ll literally never have everything checked off. For a Type A person like me, that was a huge adjustment that I really struggled with at first. It’s all about prioritizing and accepting the things that you cannot do, because believe it or not, we don’t all have the same 24 hours in a day.

I’ve mostly figured things out now. I work during the day like a normal person. Nights are reserved for mental relaxation. Sometimes I’ll work weekends if I’ve had a particularly upset schedule Monday through Friday.

But it’s still not the same as going in at 8 and being done at 4. It’s not the same as being able to leave all the mental work baggage at your workplace. Because your business affects financial decisions in every other area of your life.

And you’ve got some pesky ambition to go along with it that will always be pushing you to do more, even when you know you can’t or shouldn’t.

Would I do it again?

Don’t get me wrong. I’m happy with my business, and I want to keep doing bigger and better things with it. I want to keep helping people in a meaningful way and support my family while I’m at it.

Two years ago, the floor dropped out from under my day job thanks to a regional work shortage in a career I had just finished re-training for. I’m extremely lucky I had this going on.

But I would caution people to look both ways before they dropped everything and quit their stable 9-5 in pursuit of some illusion of perfect freedom to be found in self-employment. The grass is always greener, and we’ve definitely got some brown patches over on this side.

2 thoughts on “My Love/Hate Relationship with Self-Employment

  1. Fruclassity (Ruth)

    I appreciate this post, and I can relate to it. My husband is self-employed, and so many of your points apply to him. “A lot of times, when we read about how bloggers go full-time, it feels like they’ve won at something.” It’s so good to show both sides of the story. Tonya had many of the experiences you write of, and she returned to regular work. Self-employment is not necessarily the answer for everyone.


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