We caught up with the brilliant and insightful Elliot Strunk a few weeks ago and have shared our conversation below.
Alright, Elliot thanks for taking the time to share your stories and insights with us today. We’d love to hear about how you got your first non-friend, non-family client. Paint the picture for us so we can feel the same excitement you felt on that day.
Whenever I had a full-time job, I was always freelancing. The extra money was nice but I wanted to have the control of choosing my own clients and learn about managing a design business outside of the safe confines of work.
When I began to get the “itch” to leave the studio I was working for and make the leap into freelancing, I grabbed a steno notebook (the ones with coil binding at the top and a vertical line down the middle of the page) and began keeping a journal. Whenever I had a problem of some sort (whether at work or freelancing) I would write it down on either the left (for work stuff) or right (for freelancing) and ask myself how the problem would be solved in the opposite setting. At the end of the year, I went back through the notebook to see which side of the page contained more joy and possibilities. It was freelancing.
I gave my employer three months of notice for a smooth transition and headed out on my own with one client, a start-up company developing a board game. So that was a fun project to start with!

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.
I help smart, curious leaders clarify their strategy and story so they can align their people and drive meaningful change.
One of the most interesting – and daunting – things about design is that it’s an applied art that exists at the intersection of creativity, business and technology. Each day those three things intersect in a different place, so there’s a lot of dynamism. New business verticals. Different tools and devices. But there are a lot of foundational principles as well: know your audience, begin with the story you’re trying to tell.
One thing I realized pretty early is that you’re running a marathon, not a sprint. That means success comes from being disciplined and focused but also open minded and curious. There’s always more to learn, especially as tools and platforms enabled by AI continue to be built, updated and integrated.
For example, two products I’ve been working on are using AI in different useful ways.
Our new knowledge platform, Echo, has been built for that one lonely soul in charge of marketing inside an organization that has very little support, if any at all. I have dropped my three decades of design thinking and strategic work into this tool. People are finding it to be valuable.
Our second project is a knowledge collection and connection platform called Continuum. It allows users to store their links to articles and websites, load up PDFs, images and videos. But the collecting is only the beginning. It then crawls those assets and uses AI to find unseen conceptual links to connect dots for the user to uncover unseen associations and comparisons they can use to shape their creative thinking for client projects or their own.
There’s a page highlighting these and other projects on my studio’s website: https://fifth-letter.com/spinoffs

We’d love to hear a story of resilience from your journey.
I moved from Ohio to North Carolina without knowing anyone and with no job.
It’s hard to imagine for people who grew up in the era of fast internet speeds, social media and smart phones, but once upon a time long distance phone calls, dial-up email connections and showing up for in-person meetings was how you built a network and hunted for career opportunities. I was a member of a professional design organization and they had a printed national directory. I used that book and some printed design annuals to find people whose work I liked and I set out to meet them. That was 30 years ago.
That experience taught me the value of networking and collecting people. Learning to accept help and also being a resource for others. I became successful because of the kindness, patience and opportunities provided by others, so I try to create those opportunities for friends old and new when I can and when I’m called upon to build a team of diverse collaborators for client projects.
Another way to create opportunities and stay humble is to get out of your bubble. Hang out with people who don’t care about design and creativity the same way you do. Discover what they care about and what you both have in common. Use them to test your ideas. Have them be your reality check. It can be humbling and frustrating at times, but over the long run it will make what you build better and create with more empathy.

Are there any resources you wish you knew about earlier in your creative journey?
Looking back, I will say there was one thing I was aware of intuitively and another that I realized with time. I knew enough to know you regret the things you don’t do more than the ones you do. I wanted to give being on my own a real shot at a time in my life when I didn’t have a kid and my wife had an income we could fall back on. This revealed the second thing it took time for me to figure out. As your life progresses, you’re not going to have fewer financial or life responsibilities. Learn fast and fail fast. You can always go back to a job, so save up and invest in yourself and your future. After all, luck is when preparation meets opportunity.
My wife and I took a holiday trip to Hawaii for two weeks and talked over launching the business and what it would take. She was incredibly supportive. (You have to have family and friends in your corner to make a true go of it. Remember, it’s not only a sacrifice for you.)
Giving myself a three month transition allowed me to incorporate my business with a lawyer, begin drawing up contract templates, open bank accounts and get all of the housekeeping items taken care of. This was over 20 years ago. Doing this work online now makes things so much easier and faster. However, don’t discount personal relationships. You should have a face and a name in your mind as you read the words lawyer, banker and accountant. You will need them at some point and they can also be great sources of referrals.
Contact Info:
- Website: https://fifth-letter.com/
- Instagram: https://www.instagram.com/madebyfifthletter/
- Facebook: https://www.facebook.com/madebyfifthletter/
- Linkedin: https://www.linkedin.com/in/elliotstrunk/
- Twitter: https://www.instagram.com/madebyfifthletter/
- Other: https://www.twodesignerswalkintoabar.com/ (Podcast)
https://www.mixed-results.com/ (Collage artwork)



Image Credits
Portrait by Urban Bloom Photography.

