Remind Me Again Why I’m Self-Employed


This post is completely and utterly about first-world problems. I admit it. But it’s some thoughts that have been tumbling around my head this week, so here goes.

A while back, I was talking to someone about self-employment. “I wouldn’t recommend it,” I said. “I would’ve fifteen years ago, but not anymore.”

Why? Well, a lot of reasons.

I became self-employed about fourteen years ago. I had worked for a publisher, which I loved—but they closed our division and I was laid off. Then I worked for a solid-waste company, which I hated. I moonlighted as a freelance editor and learned that I was making as much money in my off hours as I was doing my hated 9-to-5 job at the solid-waste company.

It was an easy decision: I went full-time freelance. And I went back to school for my master’s, mostly just to give me some reason to actually leave the house on a regular basis.

At the time, they were both good decisions. Editing is never going to be a high-paying job, but I made enough as a freelancer that I could live and travel, and that was all I needed and wanted. I enjoyed doing my master’s, made new friends, and met my husband there. Good decision!

The downside to being a full-time freelancer was the self-employment tax. It’s a killer—an additional 15 percent on top of state and federal taxes. Ouch. I understand the purpose—to cover Social Security and other contributions that normally an employer would cover—but that doesn’t make it less painful to pay. Still, I just factored it in as a cost of doing business and went about my way.

Then another downside popped up. Once COBRA ran out and I was no longer eligible for student health insurance, I was screwed. Because I have a very minor heart issue (mitral valve prolapse) and because I’ve been treated for depression (who hasn’t?!), no one wanted to give me health insurance. An agent finally helped me find one company who would insure me, but it was phenomenally expensive. I sucked it up and paid the premiums—just another cost of doing business. It was frustrating, though, because at that point in my life I was extremely healthy and rarely needed medical care—it felt incredibly annoying to be discriminated against because I have a completely benign heart condition and haven’t always been 100 percent happy.

Once Chris and I were a solid couple, living together and intending to be married, we got declared domestic partners, so I could be on his insurance. I remember my sister asking, “Doesn’t that mean you’re gay?” No, it means the insurance system in our country was obnoxious, and I was trying to find a way to get coverage without going broke.

Being self-employed and working at home was great when we had our first child—in a way. It was great, but it definitely wasn’t easy. Theo didn’t nap much, so it wasn’t as if I could schedule my work time during his naps. Chris and I ended up with an elaborate system in which we would get up at 7, and I would work from 7 to 9 while he watched Theo. Then he would leave for work, and I would keep Theo from 9 to 5. Then the minute he walked in the door at 5, I’d hand Theo off to him, and I’d work from 5 to 9, at which point I would have to call it a night because I was too darn tired to work anymore.

We did this for about six years—even after welcoming a second child. It was exhausting. Neither of us really wants to do it again. We never ate dinner as a family because I was working nights (though really, eating dinner as a family is one of those things I think is kind of overrated—but that’s another topic for another post). I barely saw Chris. Our kids didn’t see us together much, except on weekends. (I’ve always been fiercely protective of our weekends and vacations together, because it’s the time that we actually get to be a foursome.) But it worked. We were able to make ends meet and raise our kids.

By this point, I’d been self-employed for about ten years and never had a raise. Because that’s the other thing about being self-employed—you don’t get raises. (Unless you give them to yourself, but that’s kind of challenging, depending on your industry.) The cost of living keeps going up, but your wages don’t.

When Sam entered school, we had a shift in schedule, and finally I was able to work during regular working hours, for the most part. I could also pick up my kids at school and participate to some extent in their school activities, which was awesome.

Still no raise. Still dependent on Chris for health insurance (thank god he has a job with good benefits!). But at least able to have some sort of family life. And I was able to diversify my client base and take on some more lucrative assignments, which kinda sorta takes the place of an actual raise.

So we’ve been in this sweet spot for a couple of years. As I said earlier, editing is never going to make anyone wealthy. Neither is writing, which I’ve branched out into. We’re both editors, so suffice it to say, we live paycheck to paycheck. When we take a vacation, it generally requires some elaborate financial planning to make it happen. Still, it’s been a sweet spot because we haven’t been falling behind as much as usual.

But now Sam is starting kindergarten in the fall, and we’ve hit a brick wall—and it is once again because I’m self-employed and work at home. You see, Sam was in full-day preschool. He likes it and enjoys the routine very much, and it allows me to work during the day. But kindergarten is only three hours a day, so unless we can figure out what to do for childcare, I’m going to have to drastically slash my work.

I thought I had the solution: childcare provided by the Regional Center! Because Sam has a disability and is a lifelong client of the Regional Center, he’s entitled to that. Only I found out this week that he’s not—because I work at home. If I went to an office every day, they would give him as much childcare as we needed. His caseworker said, “So if kindergarten ended at noon, we’d cover childcare until 6:00 or whenever you or your husband gets off. But that’s only if you work outside the home. If you work at home, I’m afraid we don’t offer anything.”

That was disheartening, to say the least. There’s already a bit of a stigma about working from home—people think you don’t really work. If you’re self-employed, let me tell you that’s not true. Because if you don’t work, you don’t get paid! So when I say I’m working at home, I’m really working. Sure, my schedule is flexible. I might take an hour off to go to the gym. But I don’t take a lunch break, either—I work straight through.

So anyway, it was frustrating to hear that because I work at home, I’m not really considered to be working, and thus Sam doesn’t get this benefit.

But aside from that ego bruise is the more pressing issue: We are now sort of screwed. Three hours a day is not enough time for me to get my work done. Especially not because I have to take two hours a week off for therapy (much needed right now) and two hours a week off for acupuncture (which helps tremendously with fibromyalgia pain for me and keeps me off meds). Neither of those things can be done with Sam in tow, so I’ll need to do them during that fifteen hours a week he’s in kindergarten. Now we’re down to eleven hours of work time, when I used to work at least thirty hours a week. Factor in any other things that pop up, and I guarantee it’ll be less than eleven hours a week.

I looked into having him go to after-school care at his current preschool (which also does after-care for older kids). That’s a great solution because it’s close, they know him well, and he actually eats for them (with me, I guarantee he won’t eat a decent lunch after kindergarten). But it’s an unusable solution because they charge $800/month for after-care. There’s absolutely no way we can come up with that. Even though it would allow me more work time, remember that I don’t make much and I have to pay regular taxes plus self-employment taxes: my take-home probably wouldn’t even equal $800/month, so there’s just no point.

I thought about hiring a babysitter to hang out with him here while I work a few afternoons a week, but that’s even more expensive than the $800/month at his current school.

Chris brought up the idea of after-care at his school. Theo goes to it sometimes, and it’s reasonably priced. But the supervision isn’t good enough for Sam, in my opinion. As much as we like him to have all the experiences of typical kids and be held to the same expectations, there are instances in which we have to remember that he’s not typical. He requires more supervision than a typical five-year-old. He has absolutely no sense of danger, and his self-care skills are currently limited to getting his own snacks. The after-care at school is great for relatively independent kids like Theo who can take care of themselves and just need an adult around to keep an eye on them, but I don’t believe it’s enough for Sam.

That’s the same issue that comes in when we consider me working with him at home. With a typical five-year-old, in general you can set them up with some activity to do while you get bits and pieces done. That isn’t so much the case with Sam. It is if you hand him an iPad—he’d be happy to sit on that thing for hours! But that wouldn’t be good for him, so it’s not a good solution. He’s not yet at a developmental age where I can hand him some crayons and tell him to color for twenty minutes, or sit him down with a puzzle to do for twenty minutes. He can focus, but he still needs someone there to guide him in activities like that.

So…we’re stuck. I’m honestly not sure what we’re going to do, especially since we were considering having Sam do two years of kindergarten so he’d be better prepared for first grade (and its academic challenges) when it comes. Our two options are: (1) I mainly take the next two years off work, or (2) I go back to working nights and we become a somewhat splintered family for two years.

I think Option #2 is going to be it, unfortunately, because Option #1 won’t work. We literally cannot exist on only one salary—even if every single penny of Chris’s paychecks went to bills, it doesn’t cover them all. (I find myself insanely envious of many of the families around here—I wonder how the stay-at-home moms are able to do it! It’s clearly not a matter of them being more frugal—we live in a smaller, cheaper house and drive older cars than most of the people around here.)

Like I said, first-world problem. I have a job (five, in fact). I like my jobs. A lot of people can’t say they like their jobs, and I can. I have flexibility in my schedule to spend time with my kids, which is priceless.

But darn it, I have to admit that I would never advise anyone to go the self-employed route. Self-employment taxes are a killer. Getting insurance can be a nightmare (and might get worse if ACA is repealed and no plan covering preexisting conditions is put into place). And if you’re in our position, being self-employed apparently doesn’t really count as being employed.

We shall march forward, looking forward to the light at the end of the tunnel in two years, when we can go back to being a semi-normal family. In the meantime…I don’t know.

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