Top Ten Insights on Working From Home (and Being Your Own Boss)

My debut into the workforce involved peddling oversized cinnamon buns at the mall. Have you ever tried scraping hardened pecan roll syrup off of deep dish metal pans? It’s on there like cement, I tell ya! The pay was minimum wage, which at the time was three dollars and some odd cents an hour; but, hey, I could take home any uneaten goodies at the end of the night so to my teenage brain that was a pretty sweet deal. A slew of entry-level jobs followed: a restaurant here, a bar there, a number of various call centers (I’m sorry if I cold-called you in 1997 about siding and windows.) Finally, I got serious, gaining my degree and becoming a court reporter, later transitioning that skill into CART captioning for a “major” university. In each instance of my employment journey, I was working onsite for this boss or that boss, which was just fine by me.

Today, I’m still a CART captioner, but working remotely from home, as my own boss. This was out of necessity more than ambition. Turns out no one was hiring captioners in my new hometown. I didn’t want to give up my career that I enjoy and have worked many years to build, so here I am, being the boss of me! Admittedly, the prospect was daunting. I didn’t know about tax rules, or finding clients, or creating invoices, or any of that jazz. I can’t even negotiate a price at a yard sale; how was I going to pull this off?

But you know what? I love it! And it’s really not so difficult. A lot of people seem curious about all this, and seeing as I am an expert work-from-homer of just over one year now, I thought I’d dedicate this post to sharing my experience via a Late Night with David Letterman style “Top Ten List” (cue the Paul Shaffer keyboard intro and punchline rimshots.)

So without further ado, allow me to present:

Top Ten Insights on Working From Home (and Being Your Own Boss)

10. You’re better than you think. By the time I embarked on this adventure, I had already been CART captioning for six years, plus court reporting for ten years before that, always as an employee. Still, I wasn’t sure I had the skills necessary to be successful on my own. Those who were already out there doing it seemed like rock stars and enigmas. So imagine my surprise when it only took reaching out to a handful of industry contacts to get my foot in the door, and the skills and work ethic I already had were more than sufficient to keep clients satisfied. There’s really no magic to it. Just say “yes” to opportunity, and see where it leads!

9. Isolation is necessary. You’ll want an office with its own walls and a door. Taking up residence at the kitchen table or similar area for convenience sake or to be nearer the family “action” may sound nice, but when you’re trying to work and people are talking, or the TV is blaring, or the dog starts barking, it’s not cute. You won’t want to hear all that, and nobody likes to be shushed. I literally put myself in the closet. It was the only space left in my small home that was unoccupied! Luckily, it’s a walk-in closet, so there’s just enough room for a wraparound desk (thanks to my hubby for installing that) and a chair. It’s cozy, I can decorate it however I want, and the only person I have to worry about coming by and accidentally spilling their drink on my papers or laptop is me!

8. Dress-down Friday is every day. By dress-down, I mean way down. Pants may be optional. Not only pants, but shoes, makeup, really the whole shebang. This is assuming you’re home alone all day and not video conferencing. (Tip: cover up your computer’s webcam when not in use, just in case.) Even so, there’s always the possibility of a pop-in visitor, so I do recommend staying fully clothed.

7. The refrigerator is a frenemy. Food is very important to me. I can be planning my next meal while eating my current meal. So to be within 25 feet of my kitchen at all times is a blessing and a curse. On one hand, your only options will be whatever you bought from the grocery and prepare yourself. No unhealthy fast food here! On the other hand, there is no reason to skip a meal, ever. You could easily throw some snacks into the mix, as well. Suffice it to say, this relationship will need some ironing out.

6. You get used to the silence. For the first few months of work-from-homedom, be prepared to talk to yourself…a lot. It may even progress to places outside the home, like the department store or city park. This can be a bit frightening, to yourself and bystanders! But have no fear. It is simply your vocal cords’ muscle memory dying. Where there was once much conversation among and around you at the office, there is now a party of one. At around the nine-month mark, I began to keep my thoughts thunk and not said, for the most part anyway. If the silence ever does get weird, just throw on some Pandora. If Lisa in the third cubicle down doesn’t appreciate the Milli Vanilli station, well who cares? Because she does not exist.

5. Pets help. If you have pets, you will love them even more after working from home. They are the best coworkers, even though they get hair in your keyboard. A stress break is no further away than a stroke of a cat’s fur. A doggie walk is perfect for some exercise and fresh air, and most importantly a reason to get out of the house. They’ll provide you humor and love and help keep things in perspective on a tough day. They keep you from feeling lonely.

4. The dishes won’t get done. Or perhaps the laundry, or the floors. Whatever it is around the house you might think, “Oh, I’ll have more time for that,” you won’t. Because you will be busy doing work for which you get paid. Allow yourself to accept this, and make sure your family does, too. True, your schedule will likely be more flexible, so some things you may previously have done in the evening after work you might now get done in the afternoon, but that normally just means you’ll be spending time in your home office in the evening when you would previously have been off the clock. It all evens out in the wash.

3. FedEx is magic. And not in a good way. Really you could insert any delivery service here. How in the world can I be home 90% of every day, yet still miss my packages being delivered? It’s just one of those quirky mysteries of life that nobody knows. Or magic.

2. Your family will still miss you. When the time comes when you do have to work when your family is around (as will surely happen), you will still see that disappointed look on your children’s faces. Your significant other will still kiss you goodbye. All will still ask with anticipation when you’ll be done. Even your furbabies will attempt to sneak in your office for reassurance and pets (remember the necessity for a door.) That moment of pain that tugged on your heartstrings when you left for your commute to work? It still happens! The fact is you will still be physically and mentally separated during the time you’re “on the job” even though you’re in the same building. Even so, I much prefer having ditched the commute, and knowing I’m only a few steps away in case of emergency.

1. There’s no place like home…to poop! In the words of Kanye, “Sorry for the realness.” It’s just plain truth. The only 100% indisputable reason to work from home is the unfettered access to your own private toilet. And that in and of itself is reason enough. My digestive cycle used to be a major point of consternation. If I couldn’t avail myself of the opportunity before leaving for work in the morning, by midday I was in a heap of trouble, and suffered all the way through until returning home in the evening. Either that or take my chances in the public restroom; that is, public enough that there was usually more than one person in there at a time, but private enough that mostly everyone going in or out knew one another so it was extra awkward. Much misery occurred in favor of decorum! That is so not an issue anymore, and I couldn’t be happier.

I could go on and on about this topic. Not only the pooping, but from office equipment, to time management, to tips of the trade, etc., etc. Frankly, I’m learning as I go. Becoming self-employed was not an easy leap for me because it meant giving up a certain sense of security. There is really no more apt phrase than “security blanket” because I prefer to be all wrapped up in it! But looking back I realize that’s really all it was: a sense. There’s no telling whether my employer would have laid me off at any time, just as I can’t know whether the good fortune I’ve enjoyed to this point will continue. But I can choose to enjoy the journey, in prayerful thanksgiving, planning for tomorrow and living for today. At which time I may or may not be sitting in a closet, wearing sweatpants and last night’s pajama top, listening to the Top Hits of the ‘80s while editing transcripts and responding to emails. Who’s to say really?