“From Avocation To Vocation: How I Turned My Hobby Into A Career” With Katie Jenison

Chaya Weiner
Jan 8 · 11 min read

Not every client is the right client for you. — When you’re first starting out as a freelancer, you may be tempted to say yes to every client or project that comes your way. After all, you need the work (and the money) but not every client is the right client for you. Whether you have different ideas of what your services entail or vastly different work styles, taking on the wrong clients can be such a headache. Trust your gut; if something about a potential client or project doesn’t sit well with you, it’s okay to pass politely.


a part of our series about entrepreneurs who transformed something they did for fun into a full-time career, I had the pleasure of interviewing Katie Jenison. Katie is a freelance copy and content writer with a Bachelor of Science degree in English Studies from North Dakota State University. She specializes in writing content for the home building and remodeling industry, though she has clients in a diverse range of industries including, manufacturing, finance, and marketing. When she’s not working, you can often find her relaxing with a book and a cup of coffee (or wine) in hand.


Thank you so much for doing this with us! Can you tell us a bit about your “childhood backstory”?

grew up in a small town, about 30 minutes south of Fargo, North Dakota. My family moved there when I was six years old because my parents bought the local bar and grille. At the time, my dad was also working as a supervisor at UPS, which looking back was kind of crazy. He would have a full day of work at UPS, come home and sleep for a few hours, and get back up to work nights at the bar. After a couple of years, he was able to retire early from UPS and focus on the business. While I definitely get my drive from both of my parents, I think watching my dad really drove home the idea that you have to work hard to get where you want to go in life. It’s not always easy, or pretty, but it’s worth it when you finally achieve what you want.

What was the catalyst from transforming your hobby or something you love into a business? Can you share the story of your “ah ha” moment with us?

I was just about to graduate from college, and I was sort of panicking thinking about all of the student loan debt I’d accumulated. I had a great job and was also working part-time as a resident manager for the property management company I was renting from, but I kept thinking I needed to do more, so I started thinking of side hustles I could start. Nothing stood out or stuck with me until a few weeks before graduation when it dawned on me that I was about to graduate with a degree in English Studies. I’ve always loved to write, and I’d had some nonfiction essays published in NDSU’s literary journal, and I just thought, “maybe this could be something.” So, I started doing some research on freelance writing and it took off from there. Starting out was a little rocky, but after about six months, I really hit my stride and began making a fair amount of money. That’s when I started thinking about freelance writing as a long-term career option.

There are no shortage of good ideas out there, but people seem to struggle in taking a good idea and translating it into an actual business. How did you overcome this challenge?

I will admit that I had a lot of help from some really awesome people. When I first started, everything I knew I learned about online. That’s fine to an extent, but I think it can be hard to distinguish what’s real and what’s not about “online success stories.” It’s similar to how people show the best parts of their lives on Instagram; it’s easy to focus on the good parts and not so much on the mistakes. Plus, what works for one person may not work for another. Luckily, I have a lot of smart and successful business-types in my life that I could rely on to give me insight on how to run and grow my business. They helped guide me in the right direction, and I’m so grateful for all their help.

What advice would you give someone who has a hobby or pastime that they absolutely love but is reluctant to do it for a living?

Just give it a shot. The worst that can happen is that it doesn’t take off, or you decide you were happier just doing it for fun. That being said, it could also be one of the best decisions you make and open up so many new doors and opportunities for you.

It’s said that the quickest way to take the fun out of doing something is to do it for a living. How do you keep from changing something you love into something you dread? How do you keep it fresh and enjoyable?

I try to take on projects that I’m genuinely excited about. There’s nothing worse than having to fight through a project that you’re just not interested in! I also try to structure my weeks so that I can work on a passion project or two, whether that’s creating content for my own blog or writing a guest post for someone else. Finding the balance between client work and my own projects has really helped me avoid that feeling of burn out that’s common among entrepreneurs.

What is it that you enjoy most about running your own business? What are the downsides of running your own business? Can you share what you did to overcome these drawbacks?

I love the freedom that comes with freelancing. Being able to work from pretty much anywhere has been such a blessing for me, especially since I moved to Minnesota last year. My entire family is back in North Dakota, so being able to make the three-hour drive to visit them as much as possible is fantastic.

One of the most daunting parts about running my own business is that I’m 100% responsible for its success. It’s on me to manage my time and business effectively so that it can succeed. Even though that can be super scary, it pushes me to work smarter and to think outside the box when it comes to how I manage everything. In addition to keeping steady “office hours” during the week, I’ve learned how important it is to outsource some of the behind-the-scenes or time-consuming tasks so I can focus on other aspects of my business.

Can you share what was the most striking difference between your actual job and how you thought the job would be?

I had this vision of having so much extra free time each day, but it’s not like that at all. I never realized how many moving parts there are to running a business. It’s not just heading to my favorite coffee shop to write all day; it’s writing, answering emails, client calls, invoicing, marketing, admin work — the list goes on and on! The truth is, freelancing and working from home is a lot less glamorous than I ever thought. There are days where I’ll work until 11:00 pm and haven’t even changed out of my pajamas. Although it’s different than I imagined, I wouldn’t trade it for something else. I’ve learned so much about myself and running a business, especially in the year that I’ve been doing it full-time.

Has there ever been a moment when you thought to yourself “I can’t take it anymore, I’m going to get a “real” job? If so how did you overcome it?

Imposter syndrome is so real! I’ve definitely had a few of those moments in the last year. Starting a business isn’t easy, and there are some weeks or months where things are going well and others where it’s not. The highs and lows can be stressful, but I’ve found the lows are usually temporary. When they happen, I try to take a step back and give myself a short break. Then I sit down and evaluate what’s working and what’s not and try to find ways to make improvements. Do I need to adjust my rates? Should I change up my pitch strategies? Does my work style fit this client? Sometimes it just takes a little self-reflection to figure out the next step and start the upward climb again.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I once had a call with a potential client that I wasn’t fully prepared for. Usually, I’ll do a little research on their business beforehand but for whatever reason, I ran out of time. During the call, I asked about the clients they currently work with and have worked with in the past. While that’s not an unreasonable question, that was something I would have known if I had done my research because all of that was in the portfolio section of their website. As she explained where I could find that information, I could tell she wasn’t impressed with my lack of preparation, and we didn’t end up working together. It was really embarrassing at the time, but now I can laugh about it and view it as the learning experience it was. Needless to say, I make sure to leave extra time to gather some background information before a call with a potential client!

Who has inspired or continues to inspire you to be a great leader? Why?

Oh man, that’s tough! To be honest, I don’t think there is any one person that inspires me to be a great leader. It’s a culmination of the amazing people in my life who have supported me and shown me what it means to work hard, inspire others, and to make an impact.

How have you used your success to make the world a better place?

Not long after I started freelancing, I knew I wanted to share what I was learning with other people who wanted to do something similar. I started my blog, The Quiet Type, to do just that. It’s where I share my experience, tips, and advice on all things freelance writing, creative entrepreneurship, and running an online business. My hope is that I can be a resource for both new and experienced freelancers so that they can avoid some of the mistakes I made and maybe even grow their business faster than I did.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

1. Not every client is the right client for you. — When you’re first starting out as a freelancer, you may be tempted to say yes to every client or project that comes your way. After all, you need the work (and the money) but not every client is the right client for you. Whether you have different ideas of what your services entail or vastly different work styles, taking on the wrong clients can be such a headache. Trust your gut; if something about a potential client or project doesn’t sit well with you, it’s okay to pass politely.

2. Don’t undervalue your work. — On that same note, don’t feel like you need to discount your services because you don’t have as much experience as other freelancers, or a potential client asks you to do it for less. In my experience, those clients are almost always the ones that expect you do more work than first agreed and for far less than you deserve. As long as your rates are in line with the market and you believe they represent the value of your work, don’t feel like you have to charge less.

3. No one is as invested in your success as you are. — At the end of the day, no one cares about your business as much as you do. In fact, many people may question your decision to start a business in the first place, especially if it means leaving a “safe” job. As difficult as it may be, you’ll need to learn to tune out the naysayers. Focusing on growing your business and obtaining your definition of success is the best way to prove them wrong.

4. Stay in your lane. — Paying attention to and trying to emulate what everyone else is doing almost always leads to imposter syndrome. Don’t be afraid to be different because that helps you stand out in the crowd.

5. Don’t get too comfortable. — When I first started freelance writing, I had a client I was creating social media captions for. We had a three-month contract and everything was going well, so I was surprised when she told me she wasn’t going to extend the contract. Losing that contract and the income it provided threw me for a loop, but I learned not to get too comfortable. Contracts end, so you always have to be on the hunt for new clients and work, and make sure you have a safety net if something falls through unexpectedly.

What person wouldn’t want to work doing something they absolutely love. You are an incredible inspiration to a great many people. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

It may sound kind of “woo-woo,” but one thing I’ve focused on in the last year or so is mindset. The way you view your life and the world around you has such an impact on everything you do. With that in mind, I’d really like to encourage people to take the time to reflect on the things, big or small, that they’re grateful for in their lives. I take the time each day to write down 3–5 things that I am thankful for, and it’s done a lot to improve my overall mindset. It also reminds me that even if things aren’t perfect, they’re still good — it’s all about perspective.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Don’t wait for the right opportunity; create it.”

People always say timing is everything, but I’ve found that in most situations, there’s never a perfect time to do something. Sometimes you just have to take the leap and make things happen. For me, that was freelance writing full-time. I had a pretty detailed plan on when I would quit my job to freelance full-time, but that all went awry when I moved to a new city. At the time, I wasn’t far enough into my plan to feel comfortable freelancing full-time, so I got a “real” job. That lasted about five months before I realized that I wasn’t happy and I needed to make a change, so I took the leap and haven’t looked back since. The path may not always be clear, but that doesn’t mean it’s impossible.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

I’d have to say it’s a tie between Joanna Gaines and Jenna Kutcher. They’re both such savvy businesswomen and I have no doubt they’d each have a lot of insight to share. Joanna has such a creative soul and everything she does, she does well. She’s turned her love for design into this ever-evolving business that I find fascinating as well as inspiring.

Jenna, like me, is from the Midwest. While she grew up in Minnesota and I grew up in North Dakota, I’ve felt a connection to her from the very first time I stumbled upon The Goal Digger Podcast. I find it so impressive that she turned a newfound passion into a thriving business and successfully pivoted as her passion changed and evolved. To be able to connect with, inspire, and teach so many new entrepreneurs is amazing, and I think it really speaks to her kindhearted and generous nature.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

Chaya Weiner

Written by

Director of branding & photography at Authority Magazine’s Thought Leader Incubator, helping leaders establish a brand as a trusted authority in their field

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

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