The Reality of Seven Years: Growth, Grit, and Uncertainty in Business

Seven years ago, I set out on a journey that would change my professional life forever. I remember sitting in my office, trying to figure out my next move after a global restructuring at JLL. It was a moment of uncertainty, but also one filled with possibility. That was when I decided it was now or never—I was going to start my own business. That decision led to the creation of 26 Characters.

Starting 26 Characters was both thrilling and terrifying—full of moments of doubt, triumph, and everything in between. Running a business is a constant battle, and while things are more stable now and I have a better sense of how to manage it all, there's always the unpredictability. That's also the fun part—figuring out how to adapt and succeed even when you can't predict what's coming next.

Over these years, I've gathered insights, lessons, and stories that have shaped me as an entrepreneur. Here, I want to share the seven key lessons that have stood out the most, the ones that I think truly reflect what it means to build and run a business.

Lesson 1: Refining Intuition by Asking Better Questions

When I first started 26 Characters, my approach to finding new clients was pretty straightforward: did they need B2B marketing help, and could they afford us? Now, my thought process is much more complex. I evaluate potential clients by considering the size of their business, whether they are growing, if their industry is on the rise, who the leadership is, and if they are genuinely committed to marketing.

Early on, it was easy to chase any opportunity that came my way, but experience has taught me that not all clients are a good fit—even if they want to work with me. Sometimes, turning away revenue is the best decision for the long-term success of the business.

I've learned that asking the right questions helps me understand when to pursue various relationships and when to pass. It's amazing how much more nuanced my evaluation of potential clients has become compared to when I first started. Refining this intuition has been crucial to ensuring that 26 Characters works with clients who align with our values and vision, setting us up for successful partnerships.

Lesson 2: Do It Yourself—And Grow Because of It

When I started 26 Characters, I quickly realized there was no one else to lean on for certain tasks—I had to do it all. In previous roles, I could delegate things like presentations, writing, or creative projects to people better suited for them. But as a business owner, especially in the early days, I had to wear every hat. This forced me to grow in ways I hadn't anticipated.

One thing I've committed to is challenging myself to do one big thing every year. Writing has never been my strongest skill, so I decided that I would write a book. It took me a year to take it from the beginning all the way to being finished and printed. I don’t think I would have ever written a book unless I started my own company. Going through that entire process was incredibly rewarding, and now I have a wonderful artifact and memory of that journey.

Another example is how I didn't know anything about podcasting or how to produce a show, but I ended up creating just over 50 episodes in one year. Pushing myself to learn new skills, like writing a book or producing a podcast, has been a major part of my growth.

Lesson 3: Be MacGyver, But Learn to Scale

Starting a business is a lot like being MacGyver. You have to be resourceful, creative, and ready to fix just about anything with whatever tools you have on hand. In the early days of 26 Characters, I felt like I was constantly channeling MacGyver—making something out of nothing, solving problems with whatever was within reach, and using my wits to keep things moving forward.

I remember watching MacGyver escape a locked room with nothing but a paperclip or create a smoke screen from household items, and thinking that’s what it feels like to run a business. You make it work, even when the odds are against you. But what I've also learned is that while being MacGyver is great for survival, it's not enough for growth.

To truly grow the business, I realized that I couldn't be MacGyver all the time. I needed to hire other MacGyvers or find ways to scale that didn’t rely solely on my own ingenuity. It became about building a team that could tackle challenges with their own unique skills, so I wasn't the only one scrambling to fix things when they broke.

Even as the business grew, there were still moments when I had to step back into that MacGyver role. Sometimes, things break down unexpectedly, or someone doesn't have the right skills to fix a problem—and that’s when I’d find myself back in the thick of it, trying to make something work with what we had. It's the nature of running a business: you build systems, hire great people, and find ways to scale, but there will always be moments when you have to grab the paperclip and duct tape and figure it out yourself.

Balancing the need to be resourceful with the need to grow beyond being the solo problem-solver has been one of the biggest lessons I've learned. Scaling a business isn't about abandoning that scrappy, creative mindset—it's about knowing when to use it and when to empower others to do the same.

Lesson 4: Develop a Thick Skin—Without Losing Your Integrity

Running a business means facing challenges that can shake your confidence—you will doubt yourself, and encounter criticism from clients or partners. There will be moments when people are upset at you. If you shy away from these challenges, the business suffers. Developing a thick skin is crucial to staying resilient and keeping the business strong.

But resilience doesn’t mean abandoning your principles. One of the harder lessons I've learned is that while you need to be tough, you don't need to be ruthless. I value honesty and integrity, and I've seen other companies cross lines that I refuse to cross.

For me, staying true to my values is non-negotiable. My character and the way I conduct myself are everything. No matter how tough things get, I've never put myself in a position where I crossed a line or acted unethically, and that allows me to sleep well at night.?Being resilient while maintaining strong values ensures that 26 Characters not only survives but thrives in a way that aligns with who I am and what I believe in.

Lesson 5: Never Take Your Foot Off the New Business Gas Pedal

One of the most important lessons I've learned is that even when you have great clients who are sticking around, you cannot take your foot off the new business gas pedal. I've been fortunate to have client relationships that have lasted five years, four years, and three years. These clients have been incredible partners, and without them, 26 Characters wouldn't be where it is today.

However, relying solely on existing clients is risky. You need to be proactive about finding new business in case those accounts eventually go away. In my experience, for every three potential prospects that seem like a good fit and have interest in working together, you might get lucky and land one—or maybe even two if you're very fortunate. This means consistently pursuing new opportunities is crucial for keeping the business growing and stable.

Adopting the mindset of securing one or two new clients every year has helped ensure the long-term health of 26 Characters. It's about balancing gratitude for the clients who have been with you for years while staying focused on new business opportunities to keep momentum going.

Lesson 6: Total Responsibility—The Thrill and Weight of Ownership

This business is the only thing I've ever done where I am 100% responsible for all the successes and all the failures. In my previous roles, I was always part of a team—someone above us made the ultimate decisions or provided the budget. Now, that person is me. It’s actually a really nice feeling to be completely in charge, but it’s also taxing because I don’t always know if I'm making the right decision. Sometimes, I have to make choices without having all the information I need, and I just have to trust my instincts.

Even when someone on my team is doing a fantastic job, I feel a sense of ownership because I hired that person, and I made the decision to bring them into the business. Their success is part of my success. On the flip side, if someone isn't a good fit or their work doesn’t align with what’s needed, that’s on me as well. I take full responsibility for those choices, whether they work out or not.

This is where owning a business becomes truly exciting—everything that happens, whether good or bad, is my doing. It pushes me to constantly strive to make better decisions, build a better team, and ultimately shape the kind of company I want 26 Characters to be.

Lesson 7: It's 100% About Relationships

One of the biggest lessons I've learned is that business is all about relationships. People have helped me get to where I am today, and I couldn't have done it without those who supported me along the way. But I've also experienced relationships that I thought were strong, only to find out they weren't really there. There were people who simply didn't want to help or be clients—they wouldn't give me the time of day, or even respond to my emails or calls.

The one thing that truly blows me away is how unpredictable people can be. Some will go out of their way to help you, while others will go out of their way to avoid you. It's a very humbling aspect of running a business. You learn to appreciate the genuine relationships that bring value, while also accepting that not everyone will be in your corner. Understanding this dynamic has been crucial to building and sustaining 26 Characters and has shown me that relationships are the true foundation of everything we achieve.

Conclusion

Running a business for seven years has been like a movie—filled with drama, unexpected twists, victories, and challenges that push you to your limits. They say the 'seven-year itch' is a time when things either fall apart or grow stronger. This phrase has always resonated with me, especially when I think about the journey of 26 Characters. Each year has presented its own uncertainties, moments of doubt, and times where I wasn't sure if I was making the right decision. But just like the itch, it's about whether you let those doubts get the best of you or use them as motivation to grow stronger.

It has been a journey of building something out of nothing, fighting against doubt, and celebrating the small wins that add up over time. I've faced countless moments where I questioned my path, where every decision felt like it could make or break the business. But through every setback, there has been growth, and through every doubt, there has been resilience.

I’ve learned that success in business isn’t about having a perfect plan or always knowing what’s coming next. It’s about having the courage to take the next step, even when you don’t know where it will lead. It’s about leveraging the strength of your relationships, staying true to your values, and being willing to adapt, no matter how uncertain things get. There are no guarantees—every year brings new challenges—but that's also what keeps this journey exciting.

As I look ahead, I know there will be more challenges, more moments where I’ll wonder if I’m making the right choices. But I also know that I’ve built a foundation that is strong, that I’ve surrounded myself with incredible people, and that I’m ready to face whatever comes next. That’s what makes it all worth it—showing up, growing, and embracing the unknown, day after day.

Here’s to continuing the journey, to the next chapter, and to whatever lies ahead.