5 Awesome Things (And 5 That Suck) About Working For Yourself

Lately I’ve been spending a lot of time thinking about my career.

If you’re new around here, I own my own marketing consulting company, which I started in February of 2015. I can’t believe it’s been that long already. What’s crazy is that this is the longest job I’ve ever held; before starting my own thing, I never made it past two years at any one place (sometimes by choice, sometimes otherwise).

What’s been on my mind lately is what comes next. The weird thing about starting your own business is that there’s no corporate ladder to climb, no promotion to work toward. You’re kind of already at the ceiling, until you make new steps for yourself to climb.

My question for myself is, what are those steps?

As I think about the different options, one of the things that always crosses my mind is going back to work at a traditional 9-to-5. Part of me thinks it would be really rewarding to spend time working for an organization I’ve always admired, like CNN or in the marketing department of a brand I love. Especially being in New York City, the opportunities are endless.

But I always jump back from that ledge moments after peering over. I think deep down I know there’s no going back, at least not in the traditional sense and at least not in the near future.

Working for yourself is one of the hardest things ever, but it’s also one of the best. I’m still figuring out what I want to do for the rest of my life, but as I work on that, here are a few of the best and worst parts of my current situation.

5 Awesome Things About Working For Yourself

1. You Get To Control Your Own Schedule

This was hands down my number one motivation for leaving the traditional workforce and the biggest factor that will probably keep me from going back to it: having control of my time.

I’ve always hated being told what to do, and I could never stand the concept of having to be at work for nine hours a day if the job could be completed in five. It was maddening!

Sometimes I work 12 hours a day. Sometimes I work three. But I get to decide when that is based on what my job calls for, and it’s very empowering. I know more companies are moving away from a hard-and-fast 40-hours-a-week schedule, and I think it’s great for both productivity and morale.

2. You Can (For The Most Part) Choose Who You Work With

When I was first starting my company, I took whatever projects came my way. I think that’s the case for most people who start with a freelance gig and take it full time. I’m so grateful, though, that I now have the luxury of choosing fun, kind and interesting clients from the pack to work with.

I worked with a lot of wonderful people in my previous jobs, but also a lot of jackholes. It’s nice being able to tell those people to kick rocks.

3. You Can Prioritize What’s Most Important To You

This goes for both work and life.

Sometimes, I don’t mind taking on a project that pays less if it’s something super interesting, like writing about a topic I love. That kind of work doesn’t feel like work (and even better if it pays well, too).

On the personal side, it’s really, really nice to be able to sometimes put things ahead of work and not feel like you’re going to get crucified for it. Case in point: taking two weeks off for my wedding and honeymoon. I would probably never have been able to do that at a traditional job, or if I did it’d mean using up all my vacation days for an entire year.

4. It’s So Much Easier To Travel

My family and friends are the most important things in my life, and I love being able to work from anywhere so I can spend more time with them. Just taking a Friday or Monday off to make a long weekend getaway can be so refreshing and good for your mental health.

I’ve noticed a lot of companies becoming more accepting of floating holidays and work-from-home days, too, which is awesome.

5. You Can Wear Whatever You Want

I will never not love working in yoga pants.

5 Things That Suck About Working For Yourself

1. There’s No One To Tell You How To Do It “Right”

This is something you don’t fully appreciate until it’s gone, like having access to your neighbor’s unprotected WiFi network.

Even though I enjoy doing things my way, I also enjoy getting positive feedback on my work. This happens far less often when you no longer have a boss above you.

Ditto for making decisions. At least when you’re in a corporate environment and you screw something up, there’s someone to make it abundantly clear what you should have done differently. It’s not the case when you work for yourself. Sometimes I think I’ve done everything I possibly could to make a situation work, and I still fail. The worst part is, sometimes there just isn’t a “right” answer.

2. Your Career Path Isn’t Clearly Defined

This is the biggest challenge I’m currently dealing with.

I’ve been able to build a business that lets me pay the bills and have more freedom… now what? When you’re in a non-traditional job, the path to “what’s next” isn’t so clear.  There are so many possible answers that it feels almost paralyzing, and each one has the potential for failure.

I’ve been trying to read more books and articles on successful people to learn about the different paths they’ve taken, which has been helpful. But it doesn’t necessarily leave me feeling any more confident about where I’ll go from here when it comes to my career.

3. Whatever Happens, It’s Your Fault

Not to sound like I love throwing other people under the bus, but if you have to be under the bus, it’s nice when there’s someone down there with you. When you’re in charge, though, that bus will roll right over you all by yourself.

I’ve had contractors that I hired and trained royally fuck things up for a client, even when I thought I’d made the expectations crystal clear. Who had to make the phone call and take the fall? You guessed it. It was someone else’s mistake, but ultimately on me as the leader. Needless to say, I do not love those moments.

4. You’re Never Truly “Off”

If having control of your time is the best thing about working for yourself, then its unfortunate inverse is that you’re never truly off. I’ve gotten a lot better about delegating and setting boundaries around my personal time, but work is still always at the back of my mind.

5. Taxes Blow

Do you realize how much your employer pays to the government on your behalf? Well, it’s a lot. And when you’re self-employed, you have to pay all of that yourself on top of your regular taxes, which rounds out to about 30% of your total income.

This is one of many fun financial surprises that come with working for yourself, but I’ll save those for another sure-to-be-riveting post.

There are a lot of tough things about working for yourself, but also a lot of amazing things that you just can’t replicate with a traditional 9-to-5. Tell me: do you enjoy the stability of working in a traditional job, or are you navigating the world of self-employment like me?

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