We recently connected with Keisha Finai and have shared our conversation below.
Hi Keisha, great to have you with us today and excited to have you share your wisdom with our readers. Over the years, after speaking with countless do-ers, makers, builders, entrepreneurs, artists and more we’ve noticed that the ability to take risks is central to almost all stories of triumph and so we’re really interested in hearing about your journey with risk and how you developed your risk-taking ability.
I once read a story (probably on Facebook) that shared the regrets people expressed on their deathbeds. One that sticks with me daily was a man saying, “I wish I would have gone on the trip I’d always dreamed of.” He explained how he kept saving for the trip, but life always got in the way. His advice to younger generations was simple: “Ask yourself, ‘Will I regret not doing this on my deathbed?’”
It may sound morbid, but that question has guided all my major life decisions. When I graduated high school, I didn’t think college was in the cards for me. Coming from a background shaped by teenage pregnancy, an incarcerated parent, and low-income status, I went straight into the workforce. But I took my first big risk when I visited Moab and fell in love with the outdoors. Despite just getting a promotion at work, I decided to move there. My family thought I was joking, but I knew I had to do it, even if I failed miserably.
So, the next weekend, I found a new job in Moab and started planning. Instagram was full of “Van Life,” but all I had was my Subaru, so I made it work—living out of it for six months in the desert. That experience sparked a new dream: backpacking in Southeast Asia.
Moab was one thing—it was only a few hours from Salt Lake City. Southeast Asia was a whole new challenge. I’d never been out of the country, didn’t know the region, and didn’t even have a passport. But I saved for six months, got my passport, and flew to Bangkok—with no place to stay. I spent three months traveling with just my backpack and skateboard, navigating with a guidebook, Anthony Bourdain videos, and Wi-Fi when I could find it. Everyone was concerned for my safety, but I knew I would regret not going. The empathy, knowledge, and personal growth I gained were far greater than anything I’d have learned by staying home.
When I returned, I was inspired by the opportunities we have in the U.S. and decided to pursue a degree in Journalism. The fear of debt was real, but I applied for every scholarship I could find and earned my Associate’s Degree for $800. Afterward, I was offered the chance to teach skateboarding in Palestine through a nonprofit called SkatePal.
I didn’t know much about Palestine when I applied—just that I wanted to teach skateboarding and use my degree to document the experience. As I researched, I realized I was stepping into an area marked by conflict, and fear started to creep in. But again, I knew I’d regret not going. So, I went. Over the next three months, I met incredible people, experienced a rich culture, ate the most amazing food, and visited prolific holy sites like Bethlehem and Jerusalem. It wasn’t always easy—there were moments of uncertainty and safety concerns—but the risk was, again, absolutely worth it.
When I returned, I released a zine about my experience, full of photos, stories, and interviews. With that momentum, I decided to finish my Bachelor’s degree. Before I graduated, I landed a job as a Communications Specialist at GameStop. A year later I was laid off and, suddenly, back to square one. After a bit of panicking, I saw an opportunity. I had been helping small business owners with photography, web design, and branding as a side hustle for years, so I took a leap and launched my own business. I had little savings and plenty of doubt, but I knew I had to try.
Now, a year and a half later, I’m still learning the ropes of being a business owner, but I wouldn’t trade it for anything.
After living out of a Subaru in Moab, backpacking Southeast Asia without phone service, teaching skateboarding in Palestine, and starting my own business post-layoff, I’ve learned that risk is like a muscle—you have to work it. Planning and “sending it” are crucial parts of taking risks, but so is the confidence that things will work out. And if they don’t, at least you won’t face the regret of never trying.
Let’s take a small detour – maybe you can share a bit about yourself before we dive back into some of the other questions we had for you?
During my backpacking trip in Southeast Asia, I started a travel blog to keep my family updated. That simple project reignited my passion for design as I built the website using a web hosting platform and created a space to share my travels. When I returned home, small business owners began reaching out, asking for help with their websites, social media, videography, photography, and design work. What started as a way to document my travels soon became a side hustle, helping entrepreneurs refine their online presence and brand.
Fast forward to now—after years of freelancing and officially starting my own business last year—I’ve honed in on the services I enjoy the most and offer the most value to small business owners and entrepreneurs.
Today, my main focus is on Brand Strategy, Brand Design, and Web Design. I also offer monthly retainer packages for design work that falls outside those core areas, such as social media graphics, conference materials, print assets, or merchandise design.
When it comes to the branding journey, I always recommend starting with Brand Strategy. It’s the foundation of your business, helping you clarify your goals, positioning, and target audience–it helps you get to know and understand your business in a way that makes selling and growing your brand easy. From there, we’ll work together to craft your Brand Design that aligns with your strategy and then create a website that not only captures your brand’s essence but also drives conversions. All while making your business purpose and goals much easier to attain!
Looking back, what do you think were the three qualities, skills, or areas of knowledge that were most impactful in your journey? What advice do you have for folks who are early in their journey in terms of how they can best develop or improve on these?
I think the main three things that impacted my journey the most were being open, confident, and remembering to take a step back and breathe.
In my years of freelancing, I’ve pretty much done it all—marketing, social media management, videography, photography, web design, brand design, etc. And after trying it all, I’ve found that I’m the most valuable to my clients by offering strategy and design services. While I still enjoy some of the other skills I’ve gained, I wouldn’t have been able to find what I’m really good at without trying all those other avenues first. So I recommend being open, trying a bunch of things, and seeing what you’re the best at. You don’t have to be great at everything!
This next one is a bit harder for me but I think it’s extremely important—confidence. You have to have confidence in yourself, your offerings, and your work in order to be successful. I’m sure there’s psychology behind this somewhere but I’ve found that if you don’t position yourself confidently, people won’t see you as a resource or expert in your industry, which can mean not wanting to buy from or work with you. So even if it’s scary, feels cringey, or you feel like an imposter—you’ve got to fake it till you make it!
Lastly, take a step back and breathe. When you’re learning new skills and navigating your career, it can be discouraging and overwhelming. But I’ve found that in those moments, when you take a step back and breathe, you’re able to take a look at how far you’ve come, reevaluate what your goals are, and look at the steps you’re taking to reach those goals. That small moment of breathing and reevaluating can be game changing.
Awesome, really appreciate you opening up with us today and before we close maybe you can share a book recommendation with us. Has there been a book that’s been impactful in your growth and development?
I used to read a lot of self-improvement books and still enjoy one every now and then but I’ve made the switch to reading fiction books, specifically fantasy and historical nonfiction, and it’s made such an impact on my work.
When I was only focusing on self-improvement books, I found myself constantly trying to improve my everything and was burning myself out. When I picked up a nonfiction book for the first time in 10 years, I was not only inspired by the journeys and hardships the characters were making, but also by the elements of world building and storytelling–both very relevant things in my work of design and strategy. I’ve found reading these books at the end of a long day can be a fun way to relax without scrolling on your phone.
A few great series I’d recommend are Throne of Glass by Sarah J. Maas and Circe by Madeline Miller.
Contact Info:
- Website: https://fortunecreative.co/
- Instagram: https://www.instagram.com/fortunecreativeco
- Linkedin: https://www.linkedin.com/in/keishafinai/
Image Credits
For the headshot photo, Alix Condit
so if you or someone you know deserves recognition please let us know here.
