Career & Finance

The Pros and Cons of Working for Yourself


When I first heard the new pop song “Work from Home,” I was like “oh cool, someone’s finally singing about solo-preneurs who make their own hours and often wear pajamas pants on the bottom and a nice shirt on top for video conference calls.”

I was wrong.

Let’s just say it’s a bit sexier than my average day of working from home. In fact I don’t think they’re talking about work at all (note: they’re definitely not). But that’s what I wanna talk about and that’s what matters.

I’ve worked for myself, from home, for five years this spring. And hands down it’s the best thing I’ve ever done. But on a lot of days it definitely still feels like a job. Despite what many people imagine it to be, working for yourself comes with a lot of pros and cons, so I thought I’d catalog a few of mine I’ve noticed over the years.

Pro: You’re the boss.

Nothing makes me happier than not answering anyone every day. I may or may not have gifted myself a “World’s Best Boss” mug on the anniversary of my first year working for myself. I am wild about the flexibility and freedom that making my own hours and schedule affords me, and I think this is one of the top perks of working for yourself.

Con: You’re the boss.

But yes, this is also a con. Along with the luxury of calling the shots comes the stress of…wait for it…calling all the shots. It also requires a pretty intense level of self-discipline. When I first started out, I’d joke, “I’m calling in sick tomorrow” but the truth is, there’s no one to cover your shift but you. So that deadline, that project, that creation is still waiting and it is you alone that will take the heat if a client is unhappy. It’s a lot of pressure, but if you can handle it, the payoff is fantastic.

Pro: Work attire = nightgown

Oh the glorious dress code of working from home. I love being able to get up and get right to work before having to really “get ready.” I will, say, though, that as the years went by, I started getting dressed and putting on a bit of makeup just so I felt a little more productive…even if I was still working from my kitchen table and not going to see anyone all day.

Con: Not seeing anyone all day.

As much as I didn’t love most of my previous office jobs, there’s something to be said for the camaraderie of co-workers. In the winter I’ve truly had days where I didn’t see a soul from sun up to sun down and that can be really isolating…and part of the reason I got a dog.

Pro: Not seeing anyone all day.

And yes, to me this is also a pro. I’m an introvert, so it is wonderful for my creativity and productivity to not have people buzzing around my desk or interrupting me. And when I need to collaborate, I do so intentionally.

Pro: Making flexible income.

I can only speak for myself, but something I love about running my own service-based business is being able to crank up the clients if I want to save up for something, or say no to a few projects if I need a break. I took a 17-day trip to Europe recently and was able to double up on my clients leading up to the trip—it was a work-free trip and I didn’t take a hit financially.

Con: People think you play all day.

I’m certain they don’t mean to be, but I often feel as though people imagine that working for yourself and working from home means I’m just like eating popcorn and answering emails from the couch. And sure, some moments look like that, but I have to remind people that this is my full-time job. I work hard and long hours and usually if I’ve played hooky during the day, I’m making up for it late into the night or on weekends.

Pro: Being able to work from anywhere.

While I often complain that I’m never really “off work,” I love that I can take trips and really work from anywhere. I have several solo-preneur pals who really live this up—working poolside from exotic locations—and I really admire it.

Lastly, I can’t tell if this is a pro or a con so I’ll just close with this: When you work for yourself, growth can be harder to come by and/or needs to be self-induced.

It’s very easy to just get into a flow, which can quickly turn into a rut. It’s scary to try new things when it’s your career on the line, and it’s always painful to fail, but to me this is much better than coasting aimlessly. In the first two years of working for myself I was still so thrilled with the freedom of running my own business that I took most of the projects that came across my desk.

But then I started to feel stagnant and unhappy and I realized I should start to say no to certain projects—so I could take on more of the type of work I wanted to do. It was super scary to turn down well-paying, but off-brand (or boring) projects, but once I did, I was able to get a more clear vision of the services I truly loved doing.

Thus my brand became more refined and the right clients started pouring in. When you don’t have a boss keeping track of your progress or doing yearly reviews, it’s up to you to step in and be that for yourself, to push your business out of a rut and onto bigger and brighter things.

I know I’m just one example of someone who works for herself and that it looks very different for everyone—some of you have teams/staff, some of you work from co-working spaces, some of you work for a company or at home on your own hours….so dish it! What are some of the pros and cons about your non-9-5?