freelance strategies

Sitting around home the week before Christmas, I started thinking about some of the downsides of working from home as a solo entrepreneur. I felt like I was missing out on holiday parties and the festive spirit around the offices I’ve worked at in the past, coupled with relief that I don’t have to go into the office ghost town on the eve of a holiday weekend.

Celebrating my second New Years as a self-employed, full-time freelancer, here are some of the biggest benefits I enjoy about working for myself from home, and three big downsides to consider before cutting yourself off from a corporate job.


Easiest commute ever

The first, most noticeable benefit I noticed when I quit my old day job was the commute. I often went a week or more without moving my car when I lived walking distance from a convenience store and a few restaurants, and still find my car stays still more days than it moves. My commute now requires rolling out of bed and walking about 52 feet from my bedside to my office chair. I measured!

I hardly ever fill up my car and only need an annual oil change now due to low mileage. I changed to a per-mile auto insurance company that cut my car insurance costs in half. And I never have to deal with traffic, road rage, railroad crossings, highways, or any of the other hassles of getting myself to and from work.

No office illnesses

It took me getting sick twice in two months to realize how little I get sick since I quit my job. I used to get at least a cold every two or three months. Thanks to the cool, dry air of cubicleland, I picked up plenty of nasty germs from my colleagues coughs and sneezes. I’ve had a fairly weak immune system since I had viral meningitis in college (caused by West Nile Virus from a mosquito bite in Colorado!), and my body has far fewer germs to fight off when I don’t go into an office.

My 2-year-old recently started pre-school, and I’m expecting her to bring home new nasties to replace the germs I escaped in the office. But for now, I’m enjoying getting sick far less often than I used to.

Productivity matters more than butt in chair time

In my old day job days, some days I would leave the office and feel like I really earned my day’s salary. Other days I was all caught up on work, but thanks to the culture of Corporate America, I couldn’t just skip out and leave the office. Butt in chair time leads to the impression of how much work you get done in an office. Even though that is a horrible metric to measure employee productivity, that’s what most bosses and co-workers do when they walk by your desk. If you’re there and they see spreadsheets (or whatever you work on), you’re working. If they see a web browser up or an empty chair, you’re not working.

Now that I don’t have a boss that cares about butt in chair time, I spend a lot less time with my butt in an office chair. Instead, I work when I’m feeling most productive or have projects to finish. When I’m caught up or need a break, I play with my kids in the backyard, go out for lunch, or find another way to enjoy my improved work-life balance.

Kitchen access

At my last job, the first Friday of every month was birthday day, where we had cake or ice cream to celebrate the month’s birthdays in the office. Month end close often included pizza. I am not knocking snacks and food as employee motivation tools, but they were not good tools for my waistline. And, when I wasn’t eating unhealthy candy and food provided by my employer, I brought generally unhealthy lunches or went out for expensive, unhealthy meals at nearby restaurants. I liked my lunches out of the office, but I didn’t like my limited nearby options I could enjoy in an hour or less and the $7 to $12 cost for a lunch out.

Now my kitchen is about 54 feet from my desk. That’s half the distance of my old break room. And now, I don’t arrive to vending machines and a Keurig as my dining options, I have a fully stocked kitchen. And a Keurig too because coffee. Having access to a kitchen means I eat healthier, don’t skip meals as frequently, and save a bundle on restaurants.

Work in pajamas

I do most of my work in the same uniform as Mark Zuckerberg, jeans, a t-shirt, and a hoodie sweatshirt. But some days, I’m just not up for getting dressed in my going outside clothes. On the days I do want to enjoy a lazy, loungy day around the house, I can work in my pajamas. Some days I upgrade to workout clothes, which are just as comfortable. This benefit is not underrated.



The biggest downside of my newfound freedom is my newfound isolation. While I don’t have to commute or head to the office, I also don’t see as many people as I used to. I don’t have walk-by conversations with coworkers. I rarely go to lunch with anyone. Most of the time, I’m sitting in my office by myself typing. My family is around, so I see my wife and kids a heck of a lot more, which I love, but my human interactions are very limited compared to my full-time job days.

I work to offset this isolation by going to events at my synagogue, the local startup community, and I’m looking at joining the Ventura Chamber of Commerce to build more relationships with fellow business owners. However, there are certainly days where my job feels lonely.


So far today, I’ve had to stop work at least a half dozen times because of some distraction around the house. Between the dogs, kids, wife, deliveries, and knowing that Netflix is just a few clicks away on my second monitor, I have plenty to do that is not working. With a highly distractible personality, this can make getting everything I need finished a lot harder.

Given there are plenty of distractions at the office as well, it isn’t like changing from zero distractions to lots of distractions. But with a different type of distraction and no boss watching your butt in chair time, it is a lot easier for those distractions to become a major time suck.


The last downside of working at home as a full-time freelancer that gets to me regularly is motivation. Last year when I left my job, I had nearly unlimited energy to pour into my business. It led to record setting income, happy clients, and a full bank account. But over time, that motivation and energy has tapered off a bit. I find myself regularly looking for motivational articles about avoiding burnout and keeping my energy up as a freelance writer.

The biggest way I overcome a lack of motivation is taking a little time off, followed by a swift kick in the butt. I have to remind myself that I have one of the best jobs in the world, and one that I picked myself. Any time I think about going into the office, I get enough motivation to finish out the day and then some. After all, if I went back to a day job, I would lose a lot of freedom. That thought is more motivating than nearly anything else.

Eric Rosenberg

Eric Rosenberg is a finance, travel, and technology writer originally from Denver, Colorado living in Ventura, California. When away from the keyboard, Eric he enjoys exploring the world, flying small airplanes, discovering new craft beers, and spending time with his wife and baby girl. You can connect with him at his own finance blog Personal Profitability.

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