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.


Melanie is a freelance writer currently living in Portland, Oregon. She is passionate about education, financial literacy, and empowering people to take control of their finances. She writes about breaking up with debt, freelancing, and side hustle adventures at DearDebt.com.

Currently she puts more than 50% of her income towards debt, while living a frugal, fun life. In addition to her love of personal finance, art and music, she is also a karaoke master. Follow the adventure @DearDebtBlog.

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21 responses to “The Challenges of Working for Yourself”

  1. Kara says:

    What do they say? ‘Nothing worth having comes easy’? I admire your journey so much, and your honesty here is a big part of that. Thanks for speaking with me, thanks for being transparent, and enjoy Italy!! You deserve it!
    Kara recently posted…An Action Plan, and a New GoalMy Profile

  2. Thanks for being honest with us Melanie! I think full time often gets a bad rap and working for yourself made out to be this magical world, but both have their pros and cons! Hope you have a great time in Italy!!
    Tonya@Budget and the Beach recently posted…Did We Forget About the Recession?My Profile

  3. I love the transparency of this article. I continue to struggle with wanting to work for myself or not. I published an article on my blog about why I wouldn’t freelance full time but then every morning my alarm goes off, I change my mind, and then again when I get a paycheck after missing three sick days. I’ve not completely talked myself into one decision or another but would definitely consider freelancing once I’m debt free!
    Shirria @GDTH recently posted…All sorts of Updates!My Profile

    • Melanie says:

      It can be great, but it’s tough. Each has its own pros and cons for sure! I don’t think I could go back to working FT, but there are definitely challenges that I didn’t expect with freelancing.

  4. Tyler says:

    Thanks for the honest post Melanie. I have just started working for myself on the side (still have the 9 to 5) and it’s hard some times. I have these moments of “I just want to relax” especially on the weekend after working all week but if I don’t work I don’t get that extra pay. Extra pay I’m hoping to turn in to my primary pay someday.
    Tyler recently posted…Pushing The Right Button For Financial IndependenceMy Profile

  5. Colin Ashby says:

    I really love how there are more posts about this coming out (I read Lauren from LBeeandthemoneytree’s post a few weeks back). I am looking to go into self-employment within the next year and the aspect of health insurance and not having any real allotted “vacation” time concern me.
    Posts like these are refreshing though! Good to learn the downs as well as the ups! Too bad we couldn’t meet up while you were still in Portland, I’ll let you know if I ever come to LA!
    Colin Ashby recently posted…Don’t Settle With Staying in DebtMy Profile

    • Melanie says:

      Yeah, there are parts of it that suck. I wasn’t able to do four weeks of work in two, so I find myself working a little on vacation now. Which wasn’t part of the plan. But I had to adjust. Self-employment is worth it to me, but it can be harder than people make it out to be and there are costs like with anything.

  6. Interesting perspective! I appreciate your transparency.

  7. This is such a great reminder that self employment isn’t all sunshine and rainbows. Still the ultimate work freedom – but still work!!
    Natalie @ Financegirl recently posted…10 Blogs That Teach You How to Make MoneyMy Profile

    • Melanie says:

      For sure! I love the freedom…but it can come at the cost of others. I just remember idealizing self-employment before I quit my job and I didn’t realize how hard it actually is.

  8. On my goodness, imposter syndrome is so real and kind of ridiculous – but so difficult to shake. I just started freelance writing for a new client who reached out to me and all I could think was “are you sure? I mean, like, really sure?” Ugh.
    Mel @ brokeGIRLrich recently posted…THINX: For Bleeding on a BudgetMy Profile

    • Melanie says:

      I know the feeling well! I just try to ignore that voice and do it anyway. The more I do, the less scared I get. In that way, getting out of your comfort zone can make you more confident.

  9. I really appreciate your honesty! It’s easy to get the impression that being self-employed is all flexibility and time to travel, when there is a real weight that comes with it. Thanks for sharing what’s great and what’s hard.

  10. Yes! I couldn’t have written this better myself. After my appointment with my accountant I went home and cried. #taxessuck
    Kayla @ Shoeaholicnomore recently posted…Why We DIYed Our Taxes Our First Year of MarriageMy Profile

  11. Lisa says:

    Melanie, I totally appreciate your complete honesty in this piece. As someone who eventually wants to work for myself, it’s refreshing to hear the obstacles instead of just the good stuff. Rootin’ for ya as always!
    Lisa recently posted…Q1 2016 Net Worth UpdateMy Profile

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