We caught up with the brilliant and insightful Linda Waterborg a few weeks ago and have shared our conversation below.

Linda, appreciate you joining us today. It’s always helpful to hear about times when someone’s had to take a risk – how did they think through the decision, why did they take the risk, and what ended up happening. We’d love to hear about a risk you’ve taken.

I’ve had to take risks at a few key points in my career – moving across the country for a job, transitioning to marketing at a small agency in Kansas City, and most recently, starting my freelance marketing business.

Each of those decisions had risks and rewards, but none of them stand out as vividly in my mind as the choice to stick with my freelance career last summer when it felt like my livelihood and family were on the line.

Let me back up: Nearly 15 years into my career I’d done the big business thing at The New York Times, and I’d done the small business thing at a local marketing agency.

I saw the pros and cons in each but never much considered a third way. I was even asked if I’d want to own my own business one day, and I said no without giving it much thought. I enjoyed doing the work, and I didn’t want to manage other people doing what I loved instead of me.

Time passed, and the pandemic hit, and against all odds, our little agency survived. The owner was a fighter with loyal clients and kept all of us employed through the whole thing. As things settled down, however, she decided it was time for a change and sold the company to a tech-forward startup in California.

I was 7 months pregnant when she told us the news.

When I left to give birth and spend those precious first months with my son, I was relieved to learn that the new owner would hold my job for me. While I didn’t have an income, I at least had the security that most employees of small businesses do not have: the promise that I could come back.

During my maternity leave, it became very clear the new direction of the company wasn’t going to be a successful one. I spent hours in my son’s nursery holding him while he slept and trying to figure out my next steps. I didn’t want to leave him, but I also knew that I was not the kind of woman who would be happy at home every day.

Late one night – or early one morning? – I decided to start with the basics. How did I want to spend my days? At the time, my favorite work was building catalogs, which can be seasonal work for some clients. So I thought to myself: What if I work seasonally and stay with my son the rest of the time? My husband worked and had benefits, so I felt I had maximum flexibility.

Over the following months, I turned a sleep-deprived dream into reality.

I initially returned to the agency to honor my commitment and help bring new employees up to speed in the absence of others who had already run for the exits. Then, as things deteriorated, I transitioned to freelance support and left completely soon after.

At first, everything was perfect. I had secured a seasonal catalog client who paid bills on time and was kind and easy to work with. I had also connected with a local nonprofit through a friend and begun handling their social media as a small but consistent year-round income.

Then, my husband was laid off, and suddenly, my little “side gig” had to support our growing family.

Once again, however, it felt like luck was on my side. The nonprofit I’d begun working with needed more and more help with their communications, and I had the time and the writing and design skills to help. For months, I worked as their defacto Communications Manager and my husband was able to bond with our son while looking for the right position, rather than taking any work that came his way.

It all came to a head last summer when the nonprofit’s Executive Director came up to me and said something along the lines of “We need to hire a full-time Communications Manager. We’d like you to apply for it.”

The “smart” decision would’ve been to take it and the benefits that came along with it – or so that’s what everyone in my life said. My incredibly supportive parents, my fiercely loyal best friend, and my former colleagues all wondered why I wouldn’t take the well-paying job with the fantastic nonprofit team that appreciated my work, provided great feedback, and saw me as a team member already.

But my gut told me not to do it, and as much as my brain wanted me to take the job, I couldn’t do it. I wanted to bet on myself. Otherwise, I would lose everything I had envisioned for myself: working from home, being with my kid every day, choosing which clients I work with, and being my own boss.

So I turned it down, and I spent the next couple of months helping the nonprofit hire my replacement – all the while wondering if I was making a huge mistake.

Spoiler alert: I didn’t.

I am incredibly happy with my decision. I have spent the months since that moment growing my client base through friends and referrals to include other nonprofits, small family businesses, and large corporations. I continue to work with only clients I enjoy and endeavors I truly support, and I spend every moment in between with my exuberant toddler, whose dad now also works full-time from home.

Things could’ve gone differently at many points during the last few years, but I chose to keep believing in myself and my work – and thankfully the people in my life believed in me too.

Linda, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

I studied Print & Digital News at the University of Missouri, where they encouraged journalism students to explore all career paths in the industry. I began as a student reporter and writer before transitioning to editing and finally reaching my end goal of news design. Along the way, I learned that I enjoyed all aspects of the job aside from reporting (which I truly hated, lol).

My first position out of college was on the International Weeklies put out by The New York Times, where I did news design day in and day out. While I enjoyed the challenge of working with clients around the world and building new processes, the largely templated design work felt limiting and boring after 4 years.

So after taking time off to travel and a seasonal stint at McClatchy, I accepted a position at Breakthrough Marketing Design & Technology, a small agency where I was able to stretch myself. During my nearly 8 years there, I developed my copywriting and client-facing skills and applied my design eye to new mediums, including catalogs, websites, and ad campaigns.

When I started freelancing, I kept hearing the advice that I needed to find my specialty and build out my services around it. That never felt quite right to me, however, so I’ve continued to take on any client or project that interests me. I’ve developed a broad slate of services – copywriting/editing, design, social media, and website development – that are particularly useful to nonprofits, startups, and small family businesses that cannot afford a full marketing team but need support in all areas.

I’m proud of my ability to take a client’s concern or request and design, build, and implement a solution that not only addresses their wants but also their unidentified needs. Often, those extra steps are what they end up remembering about working with me.

Is there mission driving your creative journey?

At my last full-time position, the owner used to say something that stuck with me: “We do good work for great people.” Her goal was never to make as much money as possible or try to outperform the big agencies with their big budgets. She wanted a small, effective team that got results for clients and went home at a reasonable time.

Without consciously acknowledging it, that mentality has been the throughline for my work as a freelancer. My clients are from different industries, different tax brackets, and different locations and each has vastly different needs.

At first, it may have looked like a necessity on my part. When you’re starting your business, you take the work offered to you. In time, however, you get the opportunity to be picky about who you work for, and I choose to do good work for great people.

Any resources you can share with us that might be helpful to other creatives?

There were times in my career when I would’ve liked to begin freelancing. I dipped my toe in several times over the years, but one of the reasons I think it stuck this time is the Freelance Exchange of Kansas City (www.kcfreelanceexchange.com).

I learned about the group from its founder when she freelanced at my old marketing agency, and I tucked away the information until I was ready to act on it.

Becoming a member offered some immediate benefits: I attended a Boot Camp where I learned crucial information about starting my own business, finding clients, and paying taxes. I also went to various networking events where I met fellow freelancers and learned from their mistakes and triumphs.

The real benefits kicked in when I joined the board, first as Web Chair and later as Web Director. In this volunteer position, I helped other newbies, but I also met fabulous freelancers who sent work my work when I needed it or subcontracted for me.

Being on the board has been a big time commitment, but educational as well. I expanded my knowledge of WordPress-based website development and project management – all without having to pay for online courses. We’re getting ready to unveil a new website, and I like to think the improved features are helping me pay it forward to the next set of new freelancers.

Contact Info:

• Website: https://lindawaterborg.com/
• Linkedin: https://www.linkedin.com/in/lindawaterborg/

Image Credits
AgencyVideoStill.png – Courtesy of BTMDT