The Challenges of Working for Yourself

I just got off a great call with Kara of From Frugal to Free who is preparing for her journey into self-employment.

I excitedly told her that quitting my job and working for myself is one of the best things I’ve done. It’s true. What I also told her was that you will never work as hard as you do when you work for yourself and there will be moments when you want to pull out your hair and throw a tantrum because nothing is working.

There are many joys to self-employment, including a flexible schedule and having a theoretically limitless income.

Over the past couple of years, I’ve enjoyed not waking up to an alarm (unless I have a meeting — as a policy, I think alarms are evil), working whenever I want and I’ve also grown my income more than I ever thought possible.

But being your own boss is also freaking hard.

Over the past few weeks with the move and my upcoming vacation, I’ve been working like a fiend so I can take two weeks off and go to Italy with my mom.

I’m currently in one of those “what the eff am I doing with my life” moments and feel like the amount of stress I’m under makes the vacation not even worth it. I know I’ll sing a different tune next week when I’m drinking espresso in Rome, but now it just feels hard and unnecessary. But if I don’t work, I don’t get paid.

And let’s be honest. If you have a full-time job, you are NOT productive for eight hours straight. The same goes for being self-employed, but the difference is I don’t get paid for checking emails and doing something loosely related to work. There’s also a lot of unpaid admin and promotion time. There’s always something to do.

Also, things that use to be “first world problems” like being frustrated when the internet goes out are now big deals. I make my living on the internet and over the past few weeks have been searching for a good connection like a fiend is looking for their next fix.

WHERE IS THE WIFI?!?!?! So I end up at Starbucks. Starbucks is not my first choice, but they have reliable internet so what can I say.

It’s kind of funny because lately, I’ve been that person who brings their whole office to Starbucks. I have my mouse and mousepad, my laptop and just stay there for hours.

Today I’ve already been to two Starbucks in-between a meeting (plus side: last week I worked at a brewery).

There’s also the issue of taxes and healthcare. During a particularly vulnerable moment this week, my accountant called me to discuss the damage for my quarterly taxes.

I almost cried on the phone, but if I’m honest I was crying before he called. My tax bill is not cute. Not one bit. And now I feel broke, right before my trip. Also, I pay a pretty penny for health coverage that in a word, blows.

Back to the crying…when I had a “real job” I was good at “putting on a face” if I was going through some emotional crap. Now that I work for myself I feel all the feelings all the time because I can be myself, by myself.  

While it’s great to not have to put on a social face for others, it really sucks to try to work when you are having a OCD panic attack or after fighting with your boyfriend, or feeling overwhelmed and stressed.

I want to tell my brain “STOP. Now. No, really.” It’s a struggle, especially if you suffer from any sort of depression and anxiety to continue to work when everything is up to you and you have to rely on your own internal motivation.

And let’s not forget about the never-ending impostor syndrome. I still get a rush when I submit articles and feel like, “Will they find me out this time? Will they realize I’m not really a writer and I’m just a good faker who likes to play with words?”

Or the panic/fear that I’ve messed something up. Or missed a mistake. Or that all my clients will leave.

But even after all of this, I wouldn’t change anything. I’m more resilient than ever and through the struggles and fear, I’ve realized that most of my issues stem from me. Nobody else.

As a perfectionist, I put a very high standard on myself, but I realize that I’ve dealt with a number of situations being self-employed and you know what? The world doesn’t end. You move on. And keep going.

Just wanted to share a glimpse into the other side as I think it’s easy for people to think you have it all figured out when you don’t. You’re just doing the best you can. Just like everyone else.

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Melanie

Melanie Lockert is the founder of the blog and author of the book, Dear Debt. Through her blog, she chronicled her journey out of $81,000 in student loan debt. She is also the co-founder of the Lola Retreat, which helps bold women face their fears, own their dreams and figure out a plan to be in control of their finances. She is passionate about empowering women, helping others get out of debt, and focuses on the intersection of debt and mental health. Every September she organizes a Suicide Prevention Awareness Blog Tour, to help share resources for those struggling with debt and suicide. In addition to her love of personal finance, art and music, she is also a karaoke master and a cat mom to Miles and Thelonious.

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