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What It Is Really Like to Be a Solopreneur

What It's Really Like to Be a Solopreneur with Kali Hawlk

It’s no secret that millennials have a different idea of what “work” should be and what our careers should look like. We crave freedom in our schedules, creativity in our craft, and we want to make a difference while doing it.

This is just one reason the entrepreneurial mindset is popular among twenty-somethings. Many of us have side hustles and multiple streams of income. And some of the bravest have struck out on their own, building their own businesses and reputations for themselves.

Kali Hawlk is one of those people. She knew her current day job wasn’t her dream job, so instead of waiting around for it to come to her, she created it. She started as a blogger, and has since transformed that blog into a thriving, successful business as a solopreneur in her chosen niche.

At the beginning of her writing career, Kali was a Contributing Writer at GenTwenty and we’re so thrilled to have her back today to chat about what it is really like to be a solopreneur.

GenTwenty: Let’s start with a definition, what does it mean to be a “solopreneur”?

Kali Hawlk: A solopreneur is anyone who is self-employed and runs a very small business — and by small I mean, a one-person shop. I prefer using this term to describe myself over something like “entrepreneur,” because I feel it aligns more with my own mindset.

When I think entrepreneur, I think someone who runs a more traditional business with big plans for scaling up, hiring employees, and so on. To me, solopreneurs are people who start very small, flexible businesses that they can run on their own without other employees… and who plan to keep their businesses small and flexible.

G20: How did you get your start with a side business? What type of work do you do?

KH: I always dreamed of being a professional writer — but I had absolutely no idea how to make that happen. I also graduated right in the middle of the Great Recession with a humanities degree (specifically, a BA in history with a minor in professional writing), which made job hunting a pain. Anything remotely close to my field often required a Master’s degree, was part-time work, or paid far too little for me to take care of my own expenses. Some positions checked off all three of those boxes!

I took the first job that came along that was full-time, offered benefits, and paid enough for me to pay my bills. I decided that if I could get on my feet financially, I could worry about starting a more fulfilling career later. It’s not what most people want to hear, or even do, but it worked well for me. I built a solid financial foundation that’s allowed me to do a LOT since taking that first crappy job.

The whole time I worked there, I kept applying for other jobs — I applied to be a writer, an editor, a marketer, a researcher, a guide at local museums — and never heard from anyone. Finally, I got fed up with sending my information into a black hole and it dawned on me that I didn’t have to wait for anyone to give me a chance. I could give myself a chance!

So I started a blog and started writing. I chose personal finance as my topic because money had always interested me. I wrote for me and I loved it. Eventually, I started applying for freelance writing jobs — and I used my blog as my portfolio. I started picking up more and more gigs until I had a solid side hustle as a freelance writer.

At the same time, I started looking into things like content management and digital marketing. That combined a lot of what I loved — writing, editing, research, and so on — and provided a good balance to just writing all the time. I found my niche with financial planners, who turned out to be numerous and in severe need of help building online presences.

Everything started with freelance writing, though. And when you work online, everything is based off your ability to communicate well in writing. Once I proved I could do that, I had more and more chances to expand my experience and work in areas that weren’t strictly “writing only.”

G20: How long has your journey taken you? What was your schedule like while you worked both your day job and your side hustle?

KH: I started trying to get freelance work in 2012, and managed to land a very small amount of work. I think I managed to pay for one nice vacation that summer with the money I earned and I had a little left over to put away, but it wasn’t much. I started blogging seriously in 2013, and in the winter of that year things took off. I started landing freelance writing gigs, I started building my side business in content management and marketing, and I started making real money.

My schedule at the end of 2013 and half of 2014 was insane. I quickly went from working a little under 40 hours a week with my day job to working 80 to 90 hours a week — I hung on to that day job, I ran my side business as a content manager and digital marketer, and I continued to do freelance writing on the side of all that. I would get up, work, go to sleep, and repeat.

It wasn’t fun, but it was fulfilling and satisfying — especially when I was able to make the leap to full-time self employment. I quit my job in June of 2014 and spent the rest of the year loving life as a solopreneur!

My job situation has changed since then, though. This journey has been wonderful but totally wild and unexpected! I actually picked up my dream job with one of my clients in January of 2015. I now work as the marketing manager for XY Planning Network and absolutely love it.

I’m back to working full-time and running a side business, but I’m much better at managing my time — and I do think there’s a difference between working and holding down a side hustle and working and running a side business. I work with 3 to 4 independent contractors so I can manage my business instead of being bogged down in it. I don’t get to keep as much income as I would if I ran my business by myself, but working with a virtual team means I get to work a job I’m crazy about and maintain my own brand and business on the side without running myself into the ground.

G20: What’s a day in the life of a solopreneur?

KH: Would you believe I’m STILL struggling to develop and maintain a routine?! I’ve actually been very bad about setting up boundaries with my work and I’ve totally failed to find a work-life balance, so that’s one of my biggest goals I’m working on right now. Up until this point I’ve sort of put my head down and just worked — I haven’t taken advantage of all the amazing freedoms and flexibility available to me as a solopreneur (and as an employee with a startup that allows me to work virtually and has an open vacation policy).

I’m working to change that and I’m starting with acting on my priorities. I’ll actually be traveling around all this month and working from the homes of friends who are gracious and generous enough to let me crash on their couches, and in June I’m taking a trip to Ireland with my mom, just because!

G20: How did you discover your niche?

KH: I sort of fell into it. I blogged about personal finance and money, and within that community I started connecting with professional financial planners and advisors. I realized that many of them wanted to maintain blogs and get on social media, but they either didn’t know how or didn’t have the time to manage those accounts and write on a regular basis. So I worked to fill that need.

G20: What was your motivation behind striking out on your own?
KH: I wanted to earn more money. I felt very financially stuck in my old day job. My starting salary was so low that despite big promotions every year I was really far behind. When you work for yourself, your earning potential is theoretically unlimited, and usually, the harder you work the more you can earn.

I wanted to be in control of the money I made. I wanted to save and invest more so I could accelerate my progress to financial freedom. That was the biggest motivating factor in making my own work and career.

But of course, I also wanted the ability to work how and when I wanted. I love working from home and as I mentioned, I’m starting to take advantage of the fact that I’m location independent and don’t need to report to an office on someone else’s schedule.

G20: When did you know it was time to quit your day job and make your side hustle your full-time business?

KH: I knew my schedule of 80 hour work weeks was not sustainable. When I hit that point, I knew it was only going to work for a few months. The bigger sign was when I consistently made more money on the side than I did via my day job. When that happened, month after month, I knew I could handle the financial realities of being self-employed and that it wasn’t just a fluke — it was recurring so I knew I could rely on that income.

G20: How could someone who is unhappy with their day job start a side biz and eventually turn that into full-time work?
KH: The possibilities are really endless here. You could do just about anything! The biggest action to take is to realize that you’re not happy and to change your mindset from a negative one to one that says, I can take control of my situation and I can improve my life. When you realize that you DO have a choice, that you DO have the power to take action and make something for yourself without waiting on anyone to give you permission, you’re ready to achieve your goals and do big things!

I think anyone could benefit by first building their own platform. Get a website. Buy and keep it updated. You don’t necessarily have to blog, but you can use your site as a portfolio to share your work, or as a way for people to find you and learn about what you do. Of course, I’d strongly suggest starting a blog because that allows you to expand your reach with greater ease and it helps you establish your authority.

I’d also say you need to find a very specific niche that has a need your services or products — or knowledge or ideas — can fill. It can be scary to get specific, because you may think you’re limiting yourself. But by identifying a very precise segment of the market you can serve, you become THE go-to expert and source for every single person in your niche.

G20: What is one thing about starting your own business that you wish you had known before you started?

KH: I wish I knew how valuable I was to the people I serve — I would have charged much more, much sooner! I undercharged for a very long time because I undervalued what my time and skill was worth.

G20: Lastly, are there any resources or tools you can share for future solopreneurs?
KH: The best resources are your peers. Form a mastermind group with 3-4 people who share similar goals but are at various points in their journeys. You can also find one person to meet up with on a regular basis if you’re not sure about a big group. This is really helpful, especially when, by definition, you work alone. Mastermind groups and having a business buddy to talk with allow you to hash out ideas, brainstorm, work through problems, consider new solutions from unique perspectives, and more. These people can support you and help you progress.

To connect with Kali, visit or follow her on Twitter. Don’t miss Kali’s latest post, Want to Change Your Circumstances? Change Your Mindset, for more on how you, too, can become a solopreneur.

About the Author

Nicole Booz

Nicole Booz is the founder and Editor-in-Chief of GenTwenty, GenThirty, and The Capsule Collab. She has a Bachelor of Science in Psychology and is the author of The Kidult Handbook (Simon & Schuster May 2018). She currently lives in Pennsylvania with her husband and two sons. When she’s not reading or writing, she’s probably hiking, eating brunch, or planning her next great adventure.


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