Inspired by the list-style articles of Cracked.com.

Having stumbled upon one or two uncharacteristically high-paying freelance jobs in 2010 (and none since), I have had a taste of how nice freelancing can be.

I’m not naive enough to think it would be like that most of the time. I’m not saying I think freelancing would be easy, or glamorous. I think freelancers who are able to make a career out of it work very hard, sometimes harder than those with traditional employers, and can often be underpaid, or underappreciated, not to mention that there is no guarantee of finding work.

But, for argument’s sake, let’s say I had gone through the uphill struggle of establishing my freelance writing business and had consistent work. (And, while I acknowledge that continuing to find freelance jobs would be a significant part of the job, I am not going to talk about that in this post.) So, as a full-time freelancer, without the added responsibility of kids/spouse, these are the most prominent reasons why I would enjoy my work. Aside from the writing.

1. Morning Commute = 30 Seconds. 

My current morning commute is about an hour. I arrive between 9 and 9:30. The absolute latest I can wake up and still have time to take a shower is 7:30. If I actually want to have time to relax and have a leisurely coffee+breakfast, I would have to wake up by 6:30.

To some people, this is not a big deal. I understand that. But let me tell you, I hate waking up early. I really do. But I really like having time in the morning. Rushing is not fun. Plus, if I don’t wake up early enough, then my hair will still be wet when I leave the house, which actually matters in the winter when it gets below freezing…

On the other hand, as a freelance writer, my office would be in my house. I could wake up at 8 o’clock and still have ample time to shuffle around in slippers with a mug of coffee, maybe watch the newest episode of Community that just came up on hulu. I could even make pancakes if I were in the mood. And had the right ingredients.

Working from home, it wouldn’t be that important to shower beforehand, either. So I could even happen to sleep in until 9 o’clock and get there on time.

Even if I were in a situation where I rented office space somewhere, it wouldn’t be that bad. 1) I could rent an office somewhere a little closer to where I live, so the commute wouldn’t have to be an hour long. 2) If I was late, it wouldn’t matter all that much. Making your own hours is a necessity in freelance work. If I don’t want to make those hours 9-5, I’m sure I could find a way to make it work. In addition, if I decide to work from home instead some days, or take home the stuff I don’t get done, there wouldn’t be anyone to tell me I couldn’t. As long as I meet my deadlines, and can show some progress along the way, they aren’t really concerned with the rest, right?

2. What to Wear

This is a huge problem some days. Especially icky rainy days, when I’d like to wear something pretty and springy, but I don’t want to ruin my pretty springy clothes in the rain. And some days I really don’t want to wear anything. I’d rather hang out in the chemise I wore to bed.

Working from home would completely solve this problem. Except for any video conferences in which you might have to partake, you can literally wear whatever you want. No one’s going to see you.

I’m not just talking about wearing your pajamas all day, either. That is, of course, a great argument for freelancing, but sometimes I want to dress up, too. I’m talking formal, full-length dresses, or lacy out-for-the-night dresses that are just too much for the office. Yes, sometimes you just want to wear a ball gown and sparkly jewelry, and maybe some 4-inch heels. And having to settle on a simple skirt and top combo, with much lower heels, is just unsatisfying at those times.

And I would be lying if I said that I would not sometimes “go” to work naked. No one’s around to see, I don’t want to wear clothes… only one logical option there.

3. Meal Planning

Planning meals is one of my top frustrations of working a 9-5. When you’re shopping for food, you have to take into consideration what would make a good to-go meal. And, unlike some offices, I can’t heat up food at work, so microwavable options are out. That limits me, most of the time, to sandwiches, yogurts, and snack foods. Leftover pizza works well, but I don’t always have leftover pizza. And – unfortunately – I can’t afford to buy lunch every day, even if I just go for a Dunkin Donuts bagel/coffee combo 4 days a week.

If I could get to my kitchen for my midday meals, I would have the typical options of sandwiches and yogurts, plus my stovetop, oven, and microwave. That would expand my choices so much. I wouldn’t have to say “well, I need to buy things that can travel so I can eat during the day” when I shop. Not to mention that it would save time in the morning if I did not have to prepare lunch before leaving for work. There are, I admit, quite a few days when I end up buying either breakfast or lunch because I run out of time in the morning.

I would be remiss not to mention the possibility of delivery in this mix. Want a pizza? Chinese food? Sandwich? Burrito? There’s probably some place that will deliver to you. No need to cook, and someone will bring your food right to you. Now, there is technically no rule against getting food delivered to the office, but I would feel very awkward about it. Plus, then you’d have to deal with your leftovers, which is much easier to do when your refrigerator is a few steps away.

4. Playing Music All Day!

Because of the way my office is set up, it’s not really an option to play music while I work. This is a problem for me.

Some people think you shouldn’t do this, that it’s too distracting, that it hinders productivity. I’m sure that is true for them. For me, there are times when not playing music is too distracting. Mostly, this occurs when a certain song is stuck in my head. Then, I’ll be thinking about it whether or not I can hear it. If it were actually playing, the part of my brain that can’t let it go for some reason would be happy, and let the other part actually focus on the work I have to do.

I have some song or other in my head the majority of the time. I have always played music in the background for just about every task I do, from housework to writing, even sometimes watching movies… I find that it sometimes help me focus. The times when it does distract me, I don’t believe that turning it off would help. Sometimes, the brain just does not want to do one thing, and trying to force it only has a small chance of working. For my part, I think that having music playing would be a lot less distracting for me than hearing all the sounds from my coworkers.

5. Making My Own Schedule

I touched on this a little in the first entry to the post. In freelancing, I would be working for myself. While I know that I would have to work with other people, so much correspondence is done by email these days that  it really seems unnecessary to have specifically set office hours. So maybe one day I work 12-8 instead of 9-5, or I spend the day reading and watching movies and then I write all night. Or maybe I only work 6 hours a day – if I can get the work done in that time, all the better for me. (Aside: I have the impression that many freelancers end up working more than 40 hours per week to finish projects. I’m just making a point about not having to work on a schedule set by someone else, not trying to say that I would do less work as a freelancer.)

That goes for time off, too. If I have the money, and I want to take a week off to go somewhere nice, that vacation is entirely on me. I would have to schedule my contracts to allow for that week of not working, but I have faith that I could do that just fine. There would be no one to ask for permission, no time-off-requests to make. Knowing me, I would still be reachable by email, so I could still try to address any problems that came up, but for the most part I would have the time to myself. And since freelancers are not generally paid by the hour, I would not have to deal with the worries of not getting paid for the time I take.

I want to stress that I am aware that freelancing full-time takes as much work as any other full-time job, and more than some. I’m going to be totally honest – the best option would be to win some mega-jackpot lottery, or discover that I own some artifact worth a huge buttload of money. That seems like the only way to guarantee the freedom to set your own schedule and not worry about having enough money to pay rent.

So, the question remains – lottery tickets, or freelance websites?