What I Miss (and Don't Miss) About Working a 9-to-5 Office Job

It’s a little hard to believe that I have been self-employed for almost a decade. Working full-time as a freelance writer from the comfort of my home office is a privilege that I value dearly. I’ve learned a lot along the way–many of those lessons can be found in my book–and it feels strange to look back at my life prior to this entrepreneurial journey. There are a lot of things that I miss about working a regular office job… and there are a lot of things I’m glad I no longer have to deal with.

Random Office Shenanigans

Sitting by myself at my desk as I type this, all I hear is the clickety-clack of my keyboard and some of the street noise from the open window. On many days, the silence can indeed be deafening. While I was never one to get caught up in office gossip or office politics, I do miss some of the random conversations and events that take place in a more conventional workplace environment.

Even when you don’t always get along, there is a natural camaraderie among coworkers. You partake in water cooler banter and you might play a few pranks on one another. That constant human contact with like-minded adults is tremendously valuable. Try as you might, it cannot be replaced by instant messengers and social media.

The Boss Dynamic

I am not averse to guidance and feedback. That’s how we learn, grow and evolve. However, one of the reasons why I chose to leave my regular office job and strike it out on my own was that I didn’t like being told what to do. Some bosses are great and others are more like Bill Lumbergh. No, I don’t want to move my desk as far against the wall as possible. No, I don’t think that’d be great.

To be fair, many people will say that working as a freelancer is akin to having multiple bosses. There is some truth to that, but I view my clients as clients and not as supervisors or managers. This is no different from the relationship that realtors, lawyers and accountants have with their clients.

Getting Dressed in the Morning

Most jobs have some sort of dress code. When I worked at a movie theater, we had a specific uniform. When I worked at a car rental office, I was expected to put on my shirt and tie. When I had another regular office job, the dress code was business casual. You’re always expected to maintain a certain level of professional appearance.

And while I wouldn’t say that I’ve completely descended into a state of absolute slobbery, working from home affords me a lot more flexibility. If I feel more comfortable in shorts and a t-shirt, I can do that. This being said, the dress code at a lot of Internet startups is probably not that far removed from the dress code of my home office, but I’ve never experienced that myself.

Hardware, Supplies and Support

As you can see from our friend Samir Nagheenanajar there, getting frustrated at office equipment is hardly a rare occurrence. What does “PC Load Letter” mean anyway? Then again, Samir didn’t have to pay for that copier himself. When he needs a new stapler or some ballpoint pens, he doesn’t have to buy those either. If he’s really having trouble with his computer, he can ask for help from the IT guy. None of these are the case when you’re a company of one, working for yourself. Dealing with these kinds of expenses is part and parcel with running your own small business.

Working from Nine to Five

Having a set work schedule is very much a double-edged sword. For the most part, my old office job had me start and end at the same time each day. This meant that when I clocked out for the day, I was done with work and could take that load off my shoulders. It also meant that if I was having a particularly bad morning, I still had to get up and make my way to the office by the prescribed time.

With this freelance writing business, I can generally work when I want. It’s not the end of the world if I want to sleep in a little longer or if I need to step away to do some errands in the middle of the day. It also means that I may feel obligated to work well into the wee hours of the night and throughout the weekend. With great flexibility comes great responsibility.

Predictable Paycheck

Aside from any performance bonuses that never entered the conversation, my regular job resulted in regular paychecks. It didn’t really matter how hard I worked, because I’d be paid just the same. This offered stability, but it really lacked in a sense of accomplishment or ownership of my work.

By contrast, my entrepreneurial life leads to many good months and bad months. It’s awfully rewarding when I have a particularly good month, but it can be equally devastating when I see the numbers swing in the other direction. The pressure to perform, as it were, is omnipresent.

Beyond the Office Job

When you compare working for yourself with having more of a traditional office job with a regular employer, one situation isn’t necessarily any better or worse than the other. And as much as I miss the predictability of a stable paycheck and the social aspect of working in an office, I also value my independence and flexibility. The freelance life is still for me.