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10 Reasons Why Being Self-Employed Stinks

work from home
work from home

Working in your pajamas — or “work pajamas,” as I call them — is great. So is seeing a matinee on a random Tuesday, grocery shopping when the store’s practically empty and never having to ask permission to take an extra-long lunch break. Being self-employed is certainly the lifestyle for me, but sometimes this type of career is frustrating, exhausting and heartbreaking. Here are 10 reasons why self-employment and having a work from home job kinda sucks sometimes.

1. There’s really no such thing as a sick, vacation or personal day.

Except for two days when I was so sick I couldn’t lift my head, 10 days in Costa Rica eight years ago and another 10 days in Scotland last summer, I haven’t had a full day off in a decade. On vacation, I work sporadically, and at least I get to plug away by the pool instead of in my office. It’s possible that I took an entire Christmas Day off once, but I’m not 100% sure. Weekends? They’re the best days to work because everyone else is enjoying their life, which means fewer incoming DMs and emails. When you canalways be working, you feel like you shouldalways be working.

2. You’re the escalation department. And billing. And IT.

I miss the days when a really nasty customer was immediately transferred to my manager so that she could deal with them. Now, the Escalation Department is just a more-stern-yet-still-sorta-sweet version of myself. “Don’t let other people get you down!” is easy to say until you have vicious “professionals” harassing you with character attacks because you dared to send out a bulk email. There’s also no billing department to chase down unpaid invoices, IT manager to un-crash your laptop or housekeeping team to vacuum while you’re at home with a glass of wine.

3. Home is the office and the office is home.

I love my office — it’s comfy and pink, and I kick my feet up on my desk when I’m on a phone call because I’m the boss and I can do that. Once my workday is over, I shut the lights, power down my Mac and spend the rest of the evening in the rest of my apartment. But when you work from home, the office is still always right there, beckoning. If a client calls at 9 p.m. and wants me to “just take a quick look at this link I’m sending over,” I technically can because I work from home. Sometimes I kind of miss leaving my desk behind at 5 p.m. and not having the option to work even if I wanted to.

work from home

4. Commutes are underrated.

Every now and then, I’ll get up in the morning, pull myself together and drive somewhere 45 minutes away to get a cup of coffee. The downtime you get when you commute to your office is seriously underrated. I’m amazed that I remember to pay my cable bill, book that spinning class that’s about to expire or pick up laundry detergent when I don’t have those vital few minutes in the morning to clear my head and think about my day.

5. Going online just for fun is a thing of the past.

Almost every time I talk to my mother, she says, “Did you see that hilarious/heartwarming/obnoxious post on Facebook from your brother/kindergarten teacher/cousin?” No. No I did not. By the time I’m finished with work, I’ve already visited a hundred different websites that day. The last thing I want to do is watch that oh-so-funny viral video on YouTube, search Paleo websites for a new recipe or, you got it, scroll through Facebook. I immediately revert to the good ol’ days when the Internet wasn’t at my fingertips. I even say things like, “Please don’t make me look up the name of that song you have stuck in your head. I’m sure it’ll just come to you if you give it time.”

6. Everybody thinks you’re never working even though you’re always working.

When you make your own schedule and work from home, there’s a strange assumption that you’re both never working and always working. Which one you’re doing at that moment coincides with what people need. When someone wants to discuss a work project, they don’t hesitate to call at 9:30 on a Friday night because they figure I’m never off the clock. When that same person needs a midday, wine-fueled lunch because they called in sick to work and want to vent, they assume I’m definitely not working on anything important and I can totally take the afternoon off.

7. People assume you’re dead if you don’t respond ASAP.

I can’t tell you how many times my aunts, cousins, friends and clients have said to me, “I called/texted/emailed you!” Yes, I know. It was 20 minutes ago and I’ve just been living my life since then, doing 20 minutes worth of things that have prevented me from getting back to you immediately. Just because I check my email more often than a normal person, that doesn’t mean I’m at everyone’s beck and call. In order to stay sane during my seven-days-a-week work schedule, I try to compartmentalize my time. Otherwise, I’d be answering emails and phone calls for an entire day without accomplishing anything else.

8. Apparently, anyone can do your job.

One of the most obnoxious moments of my freelance career happened a few years ago when I ran into an annoying guy I know from college. Keep in mind that when he knew me, I had two majors and a 3.85 GPA; I was an English tutor, the Associate Editor of the school paper and a member of student government; and I worked three jobs. That didn’t stop him from saying, “Oh, I saw that you write the nightlife column for the Poughkeepsie Journal now. I thought to myself, ‘I’m glad Lindsay’s finally doing something with herself.’” Then he followed up with, “I was thinking about becoming a freelance writer too. Maybe I’ll do it.”

Yeah. Just do it. There’s nothing to it.

Look, I know I’m not curing cancer. I’m not on my feet for 12-hour shifts in the ER. I don’t have heartbreaking war stories to tell. I get that there are more difficult, exhausting, mentally taxing jobs than mine. But being your own boss and/or a writer is still exceptionally hard, and it’s not something I would suggest to anyone, especially someone who chooses this lifestyle on a whim.

9. A high hourly rate does not equal a bazillion dollars a year.

During a night out researching for my nightlife column years go, an especially pushy restaurant owner asked me several times how much money I made an hour. Finally, I fired back at him: “Fifty!” He quickly shut up. Truthfully, I only made $45 an hour at the time, but that was a major raise from the $15 per hour I made at the beginning of my career and the $30 per hour I made a year or so after. Today, my rates are more than double that, and if you multiplied it by the traditional 40 hours per week, I’d be buying a yacht instead of writing about them (yes, I write about yachts). A freelancer’s hourly rate is how much they make when they’re working billable hours, but the list of things you have to do without pay are endless.

10. When you go somewhere on the weekend, the crowd is completely overwhelming.

Sometimes I reminisce about the days when I didn’t have a near panic attack if Target was overcrowded on the weekend. I’m completely spoiled by being able to work from home on my own schedule and going to the grocery store, gym, movie theater and coffee shop when everyone else is plugging away in their office. One of the best parts of my job is getting everything done when everywhere is empty, and those peaceful afternoons are fantastic…until you can’t handle Thanksgiving dinner with your family because you’re not used to being surrounded by more than three people at a time.

Want to rock this self-employment, work from home thing? I can help with that.

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