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How Your Soul-Sucking Job Can Make You a Better Freelancer

If you’ve had a bad job, a bad boss, or bad coworkers, now or in the past, raise your hand. (Hint: you’re not alone. I, Sara, am raising my hand high and proud.)

I’ve been there. I’ve had mundane jobs that made me wish I could go back to my 12-year old paper route. I’ve had passive aggressive bosses who lost the memo on what leadership was supposed to look like. I’ve had coworkers whose autoresponder to life was “that’s not my job.”

I spent years exploring the corporate, higher-ed, and non-profit worlds before striking it out on my own full-time and have no doubt that each and every one of those experiences and encounters set me up to run the freelance business that I’m running now.

So, fellow freelancer and big dreamer, if you’re currently stuck in a situation that’s less-than-stellar, here’s what I want you to do: take notes, learn, and apply. Because everything you’re going through now will help you rock your freelancing later.

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Bad job: learn what you like

Listing the various tasks I’ve been assigned throughout the many jobs I’ve had is nearly impossible. I have no doubt it’s the same for you. No matter the role we’re put in and how “specialized” it is, we end up taking on tasks we couldn’t have even imagined before.

The same will happen in your freelance life. When you’re running your own show, you are the negotiator, the accountant, the CEO, and the coffee runner. Now’s the time to learn what you like — and what you don’t.

Here’s what I mean: in my time as a “Marketing Specialist” for one company in particular, I was tasked with blogging, video editing, social media, graphic design, note-taking at board meetings, planning the annual conference, interfacing with partners, and more. Not a day went by where something new (and questionable, when it came to my original job description) didn’t drop onto my plate.

I tried it all out, and took notes. I like interfacing with designers; I don’t like futzing around with Photoshop. I like writing the video scripts; I don’t like piecing together b-roll.

Through the mundane and the challenging, keep track of the things you like, and the things you excel at — as well as what you don’t. Going into your freelance business with that knowledge can save you a lot of time and headaches when designing your services, building client relationships, and choosing where to outsource.

Bad boss: learn to be a leader

Even as solopreneurs, we’re still leaders. You’re leading your business. You’re leading your clients. You’re leading yourself.

So when you’re stuck in a situation where your boss is anything but great, observe. What are they doing right? What are they doing that irks you? What are they doing that irks others in the office?

Here’s what I mean: I learned how to give feedback from a CEO who decided that he would “grade” my team’s writing. When I got a case study back with a ‘C’ on it and zero explanation and others on my team got the same, I took my own notes on how to give constructive feedback that helps, not hinders. Next, I learned how to write effective emails from a boss that “skimmed” her emails and rarely ever responded appropriately, instigating a chain of five emails from what could’ve been two. Now, I know how to write a succinct email that makes it incredibly easy for people to answer my questions and respond effectively.

Take note of leadership styles and the situations they work in — you’ll soon see how you can apply those lessons as you deal with clients, contractors, and colleagues while freelancing.

Bad coworkers: learn to create atmosphere

Ever have that coworker who spends more time around the water cooler than at their desk? Or the one who manages to shirk all responsibility but then shows up to the team meeting to claim all the credit? I could go on, but I’ll stop there. My point is this: we’ve all been forced into environments with people we didn’t choose to be around.

It’s up to you to learn how to a) deal with those crappy coworkers and b) cultivate your own atmosphere that doesn’t invite them in.

Here’s what I mean: I once had a coworker that was incredibly knowledgeable when it came to his role, but whose work ethic was nonexistent, right along with his personality (you did not want him picking up the phone, which worked in his favor). While it was frustrating and draining to work alongside him every day, it gave me a starting point to base my future community off of: most notably, ambition + passion over extreme skill.

When you’re freelancing, you have control, for the most part, over who’s in your crowd. And while the online world might present new challenges in cultivating authentic relationships, it does give you the ability to seek out relationships that suit you and your business. Take notes on the types of personalities and people you work best with (or don’t) now to build the criteria upon which you invite other people into your circles later.

Experiment + appreciate

In Sophia Amoruso’s book, #GIRLBOSS, she refers to her job hopping as “job promiscuity” and mentions that she approached her various jobs with “a sense of tourism and experimentation.”

I want you to do the same for every day you spend in any sort of would-be soul-crushing environment. When you approach it as a learning experience, you’ll be amazed at how it can actually serve as a launch pad to an even better freelance business.


Sara Frandina & Cristina Roman One Woman Shop is a resource hub and community for women starting and growing their solo businesses. With the belief that business isn’t one-size-fits-all, OWS guides women through the ups-and-downs of solopreneurship with a membership community, e-courses, and free resources. Going it alone shouldn’t feel lonely. Find us on Twitter, Facebook , Pinterest , and Instagram.

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{ 7 comments… add one }
  • I love how you directed us to take all of the things we (mostly) cannot control about our current situation and use those to shape the environment we create for our future. It feels like those not-so-great aspects of our current phase have a meaningful purpose, not just to make us question our sanity!

    Very helpful. Thank you for sharing your perspective!

    • Yes — I’m so glad this helped you! The benefit of having a handful of soul-crushing jobs in the past is that I had to reframe them, but it doesn’t mean that they still didn’t suck some life out of me. Take away as much as you can now, though — and you’ll appreciate it later! Cheers to a bright freelancing future for you!

      Thanks for reading + commenting, Janelle 🙂

  • I LOVED this post!

    I am struggling at my current day job because of so many reasons! And now i’m going to write those all down, and come up with a plan of how to avoid those kinds of situations when I take my business full-time in January!

    I completely agree with Janelle “It feels like those not-so-great aspects of our current phase have a meaningful purpose, not just to make us question our sanity!”

    • Megan:

      So glad this post resonated with you and can help you in the final months of your day job! I’m so excited for you 🙂


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