Kat Boogaard on Working As a Freelance Writer

Working as a freelance writer can be challenging — especially when you’re just starting out. Should you work for free in the beginning? How do you even find clients?! Should you quit your full-time job? Thankfully, other freelancers have gone ahead of us.

Does it get easier to balance work and life? How do you price your services? And what do you do when you’re in the middle of a slow work season? Well, meet Kat Boogaard. I stumbled on Kat’s website a couple of weeks ago and just fell in love. It always feels like a warm hug to hear from freelancers who understand what you’re going through and how hard it is to get started.

Read Kat’s interview to see why she left her marketing 9-5 for freelancing, why she worked for free in the beginning, and how she’s found clients like Trello, Pocket, and Toggl! Enjoy!


Please tell us what you do for a living and how long you’ve been working freelance. 

Oh boy, sometimes it feels like I do a little bit of everything for a “living.” I typically describe myself as a freelance writer who’s focused mainly on online content. I’ve covered a variety of topics, but the majority of what I write falls under the career, productivity, and self-development umbrella. Whew! How was that for a mouthful?

I’ve been a full-time freelance writer for a little over five years. Some days it feels like minutes, and other days it feels like decades. 

I’ve been a full-time freelance writer for a little over five years. Some days it feels like minutes, and other days it feels like decades. – @kat_boogaard Click To Tweet

How did you end up working as a freelance writer? Was it always something you wanted to do? Did you ever work a 9-5? At what point did you realize that the 9-5 life was not for you; what convinced you?

I’d love to say that freelancing was my plan all along, but that really wasn’t the case. After college, I took on a 9-5 job in marketing. It was a good job, but the bulk of my responsibilities were administrative (trust me, I can mail merge like a boss over here). 

I’m somebody who’s a creature of habit—I love consistency, predictability, and routine (I know, the total antithesis of a freelancer). So, I likely could have stuck with that job forever. But, there was still this persistent itch to do something different. I don’t know that I can pinpoint exactly what it was, but I craved more creativity with my work and flexibility with my schedule.

Both of my parents are small business owners who have their own LLCs, so the idea of striking out on my own wasn’t quite as foreign to me as it is to a lot of other people. My parents and my husband were some of my biggest encouragers to take the leap, so after nearly two years in my full-time job (and endless venting sessions), I finally jumped ship from my role and got this freelance thing up and running. 

Kat Boogard working as a freelance writer

How long did it take you to find a rhythm with freelancing and what steps did you take to find clients and market yourself to potential clients? 

I think I’m still trying to find a rhythm with freelancing. It’s truly one of those careers where no two days look the same, and that makes it challenging to get into a really repetitive groove—which is both a blessing and a curse, I suppose!

In terms of getting started, I took a rather controversial step in the freelance world: I did quite a bit of work for free. I knew it was going to be challenging to get someone to take a chance on a writer with hardly any experience and offer a paycheck at the same time.

In terms of getting started, I took a rather controversial step in the freelance world: I did quite a bit of work for free. Click To Tweet

So, I published quite a few pieces of work without receiving a dime, just so I could have a portfolio of published clips that I could showcase.

I was also really proactive about networking. I met up with people in my own area for coffee dates and informational interviews, and relied on social media (Twitter, in particular) to start forming connections with other freelancers, editors, and brands I was interested in. 

What challenges did you face in the beginning and how did you cope? What challenges do you still face working as a freelance writer? 

There were so many challenges in the beginning. It felt impossible to find paying gigs. For one, I didn’t understand how taxes worked. I was totally unfamiliar with all of the industry jargon. I still remember the first time someone asked me to send an invoice, and my first thought was, “Oh shoot…how do I do that?”

Getting started as a freelancer was a lot of trial and error for me. But honestly, I feel like that’s one of the best ways to learn.

Getting started as a freelancer was a lot of trial and error for me. But honestly, I feel like that’s one of the best ways to learn. Click To Tweet

Through the years, I’ve managed to gain more confidence in a lot of these subjects (I can actually send an invoice now—yay!). 

One of the areas where I still really struggle is mastering my work/life balance. Breaking free from a traditional work schedule is a huge positive of freelancing, but it also makes things tricky. There are no set hours, which means that in the beginning, I ended up working almost all of the time. Late nights. Weekends. Over my vacations. Setting boundaries for myself and learning to respect my personal time has been a constant work in progress. 

White woman sits posing on steps

How do you deal with slower work seasons? Do you think work-life balance is possible for freelancers? If you’ve figured this out, I’d love to hear your tips!

I consider myself extremely fortunate that I really haven’t had any of those cliché “famine” seasons where I wonder how I’ll make ends meet. Once I got the snowball rolling, a lot of my workload has remained pretty steady and consistent. 

In those times when my calendar isn’t quite as full, I really like to take advantage of those extra hours by prioritizing some of the work that otherwise gets pushed to the backburner. Whether it’s adding new pieces to my portfolio, making some updates to my website, or reaching out to some contacts, I leverage that time to work on my business, rather than in it. 

When my calendar isn’t quite as full, I really like to take advantage of those extra hours by prioritizing some of the work that otherwise gets pushed to the backburner. #freelancingtips Click To Tweet

If my answer to the previous question wasn’t enough to clue you in, I definitely haven’t mastered work/life balance. I’m convinced it’s a possibility, it just takes a lot of conscious effort—and perhaps even a major mindset shift.

One of the things I’m realizing is that you need to get comfortable with things being unfinished. You need to give yourself permission to shut down and relax—even if there are still tasks lingering on your to-do list.

As a freelancer and a business owner, there’s always going to be more that you could do. But that doesn’t mean you should do it right now. I know—it’s way easier said than done. 

How did you figure out how best to price your services? That’s something a lot of business owners & content creators struggle with.

Trial and error. So much trial and error. I’d set a price for something, and then realize that I could’ve charged way more for it—so, I’d do so the next time I was asked for a similar quote.

I wish I had some sort of insightful nugget or tangible piece of advice to offer here, but I really don’t think there’s a refined system that’s going to work for everyone. Sometimes you just need to suck it up, quote a rate, and learn from that process. 

What do you love most about what you do? How have things changed for you since you started? 

There’s so much to love about freelancing. Being able to be home with my two rescue mutts all day seems like the obvious answer, but instead I’ll say this: having so much control over what I work on.

Wisconsin Freelance writer Kat Boogard

I love that I’m the one who has the final say on what projects I will and won’t take on. I think that’s a level of authority you don’t get in your career when you work in a “traditional” job (at least, not until way later), so I feel super lucky to be able to have so much say in where my own career is headed. 

Since I’ve started, my career has grown in ways I couldn’t have even imagined. I’ve been published places that I always assumed were mere pipe dreams and worked with so many amazing people. I thought freelancing would be something that I’d pull off for a year or two while I figured out what was next. But, at least for now, I really can’t imagine doing anything else.

With all of that said, plenty has stayed the same too. I’m still in my sweatpants, tapping away on my keyboard in my home office in a small Wisconsin town. That mix of growth and challenges with consistency and comfort sits well with someone like me. 

What’s the biggest lesson freelancing has taught you? Which resources would you recommend for new freelance writers looking to improve their craft?

Patience. By nature, I’m not a patient person, but I learned early on that almost nobody shared my sense of urgency. Freelancing has given me so much perspective in that regard, and now I find it easier to remind myself that not everybody is on my timeline (as much as I wish they were!). 

Personally, I like to think that I offer plenty of helpful resources for freelancers through my blog, newsletter, and personal Facebook community. 

However, beyond just intensely reading, researching, and absorbing as much knowledge as you can, I think networking can be huge! I’ve made so many valuable connections with different people who helped me get started—and who still serve as a great resource for me today. 

How to improve your craft as a freelancer? @Kat_boogaard says Beyond just intensely reading, researching, and absorbing as much knowledge as you can, I think networking can be huge! Click To Tweet

What do you wish you knew about freelancing before you started; what would you do differently? 

I wish I knew just how much time it would take to get things up and running and get paychecks in the door. As a result, I think I would’ve started up more of a side hustle before taking the leap into freelancing full-time. 

I jumped ship from my full-time job with barely any client base built up and pretty much no back-up plan, and I wasn’t prepared for how long it’d take to actually start earning some money.

It was well over six months before I finally started to feel like I had my feet under me, and that made for a pretty stressful start. 

Breaking free from a traditional work schedule is a huge positive of freelancing, but it also makes things tricky. There are no set hours, which means that in the beginning, I ended up working almost all of the time. – @kat_boogaard Click To Tweet

Morning person or night owl? What three things are part of your morning ritual?

Neither? I’m a solid afternoon kind of gal. I’ve always hated mornings, but I’m usually pretty ready to power down in the evening too. Typically between 1PM and 4PM are some of my most productive hours of the workday. 

My morning routine involves whatever sort of caffeinated beverage I can get my hands on, some snuggles with my two doggos, and my inbox (sigh). 

Who are your favorite writers (online/print) to read? 

I love reading before bed to help myself wind down and relax, and typically love historical fiction or psychological thrillers. Gillian Flynn and Kristin Hannah are two of my favorites. 

I also ready “Shouts and Murmurs” from The New Yorker religiously, but don’t have one specific writer that I follow there. 

Interested in working as a freelance writer? Read @Kat_boogaard's interview to see why she left her marketing 9-5 for freelancing, why she worked for free in the beginning, and how she's found clients like Trello, Pocket, and Toggl! Click To Tweet

What do you like to do when you’re not working?

I love any excuse to get outside—hiking, kayaking, golfing, or just taking my dogs on a walk. My husband and I are also pretty competitive with each other, so you can usually catch us in a board game showdown on a Friday or Saturday night. Other than that, we purchased our first home over five years ago, and that’s brought us a string of never-ending home improvement projects. I think we’ll be done just in time to move out! 

What else do you wish I’d asked you about freelancing?

Personally, I’m always interested in the help freelancers have enlisted to run their businesses! For example, I have an accountant, a lawyer, a website designer, and a marketing expert I can call whenever I need them. I love hearing what people other freelancers have in their own corners. 🙂


kat boogard sits on a stool in coffee shop -- interview on working as a freelance writer in wisconsin

Kat is a Wisconsin-based freelance writer focused mainly on careers, productivity, and self-development. She crafts online content for a variety of software solutions, including Trello, Toggl, QuickBooks, and Wrike, and her byline has appeared in numerous outlets, including Forbes, Fast Company, Business Insider, Inc., and The Muse. When she manages to escape her computer, you can find her obnoxiously baby-talking her two rescue mutts or talking her husband into yet another home improvement project.


Find Kat Online

Website (it’s a GEM!)

Facebook group

Twitter

Instagram


Do you have any other helpful tips for working as a freelance writer? What have you learned working as a freelance writer or freelancing in general? I’d love to know!


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