Super Practical Pros & Cons of Starting Your Own Business


If you're thinking about starting your own business (or becoming a freelancer), you've probably thought either "This is going to be so awesome!" or "This is absolutely terrifying! How am I ever going to do this?!" or if you're like me you've thought both almost simultaneously. Often times there is a level of "glamour" associated with starting your own business (I lump starting to freelance in with this, freelancing is your business). In the spirit of the recent Super Bowl I will liken this mindset to thinking about becoming a pro football player. It sounds and looks so cool and exciting - you get to play football for your job and make lots of money and go to cool parties! But then you realize you have to do two-a-days for most of the year and get your head beat in for a living. Yikes. I'm not saying that having your own business is like getting your head beat in for a living (although some people may tell you that, I will not!), but what I am saying is that there can be a grass-is-always-greener mentality when thinking about leaving your regular nine-to-five-Monday-through-Friday day job to go solo.

There's a lot to consider when deciding whether or not you should start your own business (or start freelancing); lots of logistical and financial things along with making it work with your own unique personal situation. But before you dive into all that, here are two sets of super practical pros and cons to consider:

(I will preface these by saying this: these pros and cons are mirrors of each other. They're two sides of the same coin. A pro for you may be a con for me, and vice versa.)

PRO: You're your own boss! You work when, where and how you want to and you never have to ask for a raise or time off!

CON: You're your own boss! You have to impose your own structure, schedule, and just about everything else and it's on YOU to make your business successful.

This is probably the most common pro that people who work nine-to-fives talk to me about. They say things like "you're so lucky that you get to make your own schedule!" and "that's so great that you have so much autonomy in how much you make and when you work!" And that is true. Sort of. One of the things I love about having my own business is that I have the flexibility to go snowboarding in Vermont tomorrow on a whim without having to pretend I'm sick or take a "vacation day." 

Actually, that's only half true. Because every day that I decide to take off on a whim is a day that I'm not working, which is a day that I'm not bringing in money for my business (more than likely) and eight (or more) hours that I've lost in trying to make deadlines for clients. So you can see how there's two sides to every coin right? On one side, the flexibility of when, where and how I work is awesome. On the other side of the coin, I am responsible for keeping all of my deadlines, tasks and meetings organized and it is completely on me whether or not I make a good decision for my business. There is a lot more that goes into being your own boss - you are the CEO, CFO, CMO, COO and all of the other C_O's you can think of. And while you can always hire people to do certain things for you that maybe you're not good at or don't want to do, you are ultimately responsible for the success of your business. If that excites you then you're probably headed in the right direction. If that terrifies you then you may want to think a little bit more about why you want to go solo.

PRO: Working from home!

CON: Working from home!

I hate to burst anybody's bubble here, but when I started freelancing, working from home ended up being one of, if not, the greatest challenges of going solo for me (even though it seemed great when I first started). This coin in particular needs to be viewed in the context of your own unique situation and your own unique personality, but I will share my experience and maybe that will give you some insight into how to look at this. 

To a lot of people, working from home sounds amazing. You can stay in your jammies all day! You don't have to pack a lunch! You can work from the couch! (And one of my personal favorites - when the Olympics or March Madness is happening you can watch every single event live! To me, that actually the best. But I digress.) For me, after about a month of freelancing at home, the excitement of all of these had worn completely off. 

Staying in jammies all day - when I would see my husband pull into our complex most days I would run upstairs and change into regular clothes so I would look like a normal person. While this sounds funny and cute, after a while I just started feeling terrible about myself. Partly because:

You don't have to pack a lunch - so I ended up eating all day. I do not like to admit this but over the first 6ish months I was freelancing I gained about 10 pounds. This wasn't ONLY because I was working from home but my weird eating-all-day habits DEFINITELY contributed to a large portion of that. 

You can work from the couch - this probably also contributed to the above issue, and I was just incredibly unproductive most days when I ended up on the couch. Somewhat related to this - I also got so tired of being at home all the time that all I ever wanted to do was have an excuse to get out. That makes home not feel like home anymore and that was not a good feeling.

That may have been really depressing for you to read. Don't worry, it was kind of depressing for me to write, too. But there's hope! So much hope! If my situation was different, working from home could have been a much more viable, even ideal, option - for example having little kids at home to take care of, or having a separate office in the house to do my work in separate from our living area. {I am also very extroverted, and not seeing anyone but my husband (who is the bomb - love you Matt!) for a whole day (sometimes multiple days) was really hard on me mentally and emotionally.}

An aside - hear about how I solved my working from home dilemma by joining a coworking space!

So as you consider starting your own business or starting to freelance, consider also some of these practical things. They could affect you more than you might think, but if you know they're coming you can be much more ready to deal with them and find creative solutions to make it work for YOU!