We recently connected with Lindsey Blakely and have shared our conversation below.
Lindsey, thanks for taking the time to share your stories with us today Let’s kick things off with a hypothetical question – if it were up to you, what would you change about the school or education system to better prepare students for a more fulfilling life and career?
To better prepare students for a fulfilling life and career, I would change the focus of education to include practical skills that are directly applicable to the real world. For example, teaching students how to freelance and run their own businesses is increasingly important as freelancing becomes more common. According to recent stats, about 36% of the U.S. workforce is freelancing, and that number is projected to grow. Yet, many students graduate without knowing the basics of taxes, business structures, or how to find clients. These are key skills that would help them navigate a rapidly changing job market.
Education also needs to place a greater emphasis on helping students identify their interests and talents. Too often, students are guided toward traditional careers without being given the opportunity to explore what truly excites them. We’re trained to follow a prescribed path without being equipped with the tools to pursue what we love, or to balance our professional ambitions with a fulfilling personal life.
I think a big part of what’s missing is an emphasis on teaching students how to work in the modern, digital economy. Growing up in a rural town, my ideal clients were never going to be local, so I had to learn how to build an online presence and find clients outside my immediate area. Understanding how to work remotely and use the internet to build a career was crucial for me, and I believe it’s something all students should learn in school. The digital world is no longer an afterthought—it’s where opportunities lie, and our education system needs to reflect that reality.
Lastly, I believe it’s essential for students to learn how to manage their emotions, stay calm under pressure, and reduce stress—skills that are just as important as technical knowledge. We live in a world where burnout and mental health struggles are more prevalent than ever, especially in high-pressure industries. Learning how to balance personal well-being with professional success is critical to long-term happiness and fulfillment. Schools should teach these emotional and mental tools so students can lead healthier, more balanced lives and excel in whatever careers they choose.
Lindsey, 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 grew up in a rural town where the only artists I knew were my grandparents, who painted and crafted as a hobby. While they owned a jewelry store that required creative work—repairing and designing jewelry, curating high-end gifts, and arranging beautiful displays—I never thought of it as making a living off creativity. I believed you had to choose between doing what you love and earning a decent income; the idea of combining the two felt out of reach. Even so, being surrounded by their creativity planted the seed for my own creative path, even if I didn’t recognize it at the time.
My high school didn’t offer traditional art classes—just band and floral design—but I still found ways to bring creativity into everything I did. I’m convinced I became salutatorian because I went overboard on every school project, creating scrapbook-style reports, poster boards, and fun presentation visuals. As ASB president, I took pride in decorating the school’s bulletin boards and loved being trusted to skip class to work on them. Looking back, it’s clear that I was always creative, even if I didn’t know how that could translate into a career.
When I started college, I planned to be an accountant because it seemed like a stable career. Spoiler alert: it wasn’t for me. Everything changed when I took my first fine art and design classes—I was hooked. I switched majors and got a job at the campus publicity center, where I designed marketing materials for campus events. That experience gave me my first taste of working with clients, and I loved it. After graduating, I continued along that path at an advertising agency, creating logos, branding materials, advertisements, brochures, catalogs, banners, and more for a variety of clients.
After a few years, I realized that agency work wasn’t aligned with my values or interests. I wanted to focus on design that felt more meaningful, so I ventured into freelance work. I partnered with clients like my alma mater, a feminist book club, and a children’s reading foundation. These projects aligned with my values, but most didn’t involve the kind of layout design I loved. That led me to shift my focus to layout projects like workbooks and daily journals.
Eventually, I stumbled into presentation design while working with an eLearning company. I discovered how much I enjoyed transforming complex information into clear, visually engaging slides. Presentation design felt like the perfect combination of storytelling, layout, and impact, and it has been my primary focus ever since.
Today, I help startups in climate, education, and tech tell their stories in a visual way. My clients have a story they need to share—whether it’s how their company fills a gap in the market, how they solve their customers’ problems, or a concept they need their audience to understand in a workshop or course. What sets me apart is that I don’t just make their content look good—I help them tell their story in a way that their audience can understand and connect with. Before I start designing, I ensure I understand their message fully. Then, I help consolidate information, remove what’s unnecessary, and replace it with visuals that communicate more effectively.
My approach stems from the way I process information. I’ve always had a hard time understanding things just by reading or listening; I needed to organize information visually to make sense of it. In school, I took notes with drawings and diagrams to simplify complex ideas, and now I use that skill to create designs that make information more accessible for others. I pay close attention to detail, ensuring that every element contributes to the overall goal. My clients often comment on how much they appreciate this thoughtful approach.
As a new mom, I’m more motivated than ever to do work that feels meaningful. I want my daughter to see that it’s possible to build a career that aligns with your passions and values and also provides financial stability. That’s what drives me every day: creating thoughtful, impactful designs that help my clients succeed—and maybe inspiring the next generation along the way.
Can you tell us about a time you’ve had to pivot?
One of the biggest pivots in my career happened when I left the ad agency. At the time, our main client was a car dealership, and much of the work felt soul-sucking. It wasn’t aligned with my values or interests, and I realized I wanted to do work that felt more meaningful to me. So, I made the decision to leave the agency and pursue freelancing. My goal was simple: to focus on projects and clients that aligned with my values.
After making the jump to freelancing, I worked with clients like my alma mater, a feminist book club, and a children’s reading foundation—projects that felt purposeful. But over time, I began to realize something important: while I was doing work that aligned with my values, I wasn’t focusing on the type of design I truly loved. I was passionate about layout design, but many of these clients didn’t need much of that type of work. So, I pivoted again, rebuilding my client base around layout design, focusing on workbooks and daily planners.
This shift eventually led me to work with an eLearning agency where I did my first presentation design projects. It was there that I realized this was where I truly wanted to focus: presentation design combined my love for layout with my drive to make complex information easy to understand. But as I dove deeper into this area, I realized I had swung too far in the other direction. While I was now working on the type of design I loved, I was no longer working with clients who aligned with my values. Once again, I made the decision to pivot—letting go of clients who weren’t the right fit and rebuilding my client base.
Then, I found out I was pregnant. This news was a game-changer. I needed to rebuild quickly to support my growing family and fill my savings so I could take time off with my baby, as a freelancer doesn’t get maternity leave. This final pivot allowed me to find the right balance between doing work I love and working with clients who align with my values.
Looking back, I can see that every single pivot—no matter how difficult—was necessary. And while I felt defeated each time I had to start over, thinking “Great, I have to rebuild again,” I can now see that each pivot brought me closer to where I am today. It wasn’t easy, but each shift helped me find clients who are aligned with both my values and my passion for design. It led me to a place where I’m genuinely excited about the work I’m doing. These pivots weren’t just career shifts—they were about finding a path where I can contribute my best work, feel energized, and know that what I’m doing matters.
Can you tell us about what’s worked well for you in terms of growing your clientele?
When I first started freelancing, I didn’t have any formal marketing training or a strategy to find clients. Instead, I leaned heavily on my personal network and word of mouth, which was a natural starting point. I also turned to Upwork, where I could find clients outside of my immediate network. In the beginning, it was all about providing high-quality work. I was lucky that when I delivered great results, clients would come back to me for more and also refer others my way. Building credibility on platforms like Upwork helped me get more jobs over time.
I’ll be honest, though — there were times when I would get frustrated with certain clients, and I’d let my short temper get the best of me. Sometimes I would drop clients simply because they were too demanding or difficult to work with. Looking back, I realize that if I had better tools for managing stress, emotions, and difficult client interactions — skills that I think should be taught in school — I would have been able to maintain stronger relationships and build a bigger network. Instead, I often burned bridges in the process of learning how to navigate those challenges.
One of the other things I struggled with was choosing a niche. If I had more guidance on how to identify and focus on my ideal clients early on, I wouldn’t have had to rebuild my client list so many times during my various pivots. For example, after working with clients that didn’t align with my values, I focused on layout design projects, but that didn’t work because my clients didn’t need the specific type of work I loved. And at times when I became overwhelmed with too many projects, I would just drop clients instead of finding ways to scale and grow, like bringing in a team.
In retrospect, I can see how a lack of education on running a business — particularly how to choose a niche, manage clients effectively, and scale — led to some of those mistakes. But I’ve learned a lot along the way, and the key has been to keep providing great work, nurture relationships, and proactively seek out projects that keep me excited. While it was slow at first, that steady growth has led to a solid network that I can rely on.
What I’m focusing on now is using LinkedIn Premium and Sales Navigator to build a strong pipeline of my ideal clients, and I’m really excited about where this will take me. In the past, I relied heavily on Upwork because it felt straightforward—clients posted what they needed, and I could simply apply. It was almost like using training wheels for freelancing. With LinkedIn, the process is more complex: I have to identify the right companies, find the right people within those companies, engage with them meaningfully, and then craft outreach that feels authentic and personal, not like spam. On top of that, I’m tracking my outreach efforts and creating content that resonates with the people I want to work with. It’s a lot more effort than Upwork, but I’m confident this approach will connect me with clients who are an even better fit for my skills and values.
Contact Info:
- Website: https://blakelymedia.com/
- Linkedin: https://www.linkedin.com/in/lindseyblakely/
Image Credits
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