When I started 5280 Accelerator in 2002, I didn’t even know I wanted to run a business. I had accepted a fractional sales and marketing role which left me with 20 free hours of a 40-hour work week. To fill that time, I started working with other clients, and voila, a business was born!
Twenty-five years in business teaches you things you can’t fully appreciate when you’re just getting started. Some lessons come from experience, others from mistakes, and many become clearer only when you look back and see how much has changed.
If I could go back and share a few pieces of advice with the young entrepreneur (who never imagined she’d be running her own agency 25 years later!), these three lessons would be at the top of my list.
1. Not Every Opportunity Is a Good Opportunity
When you’re building a business, it’s tempting to say yes to every opportunity that comes your way. A new client, an interesting project, or the chance to expand into something unfamiliar can all seem like steps in the right direction. Sometimes they are, and most times even the bad opportunities end up turning into valuable lessons.
What it comes down to is making the right choices about where to invest your time, energy, and resources.
Along the way, I’ve learned that not every client is the right fit, not every project aligns with our agency’s strengths, and not every opportunity moved our business closer to where we wanted it to go.
Just a few years ago we dabbled in the world of B2C marketing. Aiming to help our referral partner’s clients, we took on two new B2C clients at almost the exact same time. As I leapt in, I said to myself, “with my talented team of expert B2B marketers, how hard could it be?” 😊
We went in with our eyes wide open, learned a lot, and in the end, I discovered that saying yes to the wrong things inevitably takes time and attention away from the work that we did best. My team quickly became burned out, and I had to make the decision to let these clients go, while simultaneously making sure they weren’t left without next steps. It all ended up working out fine, and my entire team breathed a collective sigh of relief when those two clients were gone. As for me, I vowed to stay true to our strengths moving forward.
The lesson: Before saying yes, ask yourself whether the opportunity aligns with your goals, plays to your strengths, and allows you to deliver real value. Sometimes, the smartest business decision is to know when to say no.
2. The People You Choose to Work with Matters Most
I’ve always been about relationships. Over the last 25 years, I’ve found that it’s the people around me who have had the most impact on shaping my experience of running a business. The clients we’ve worked with, the team members we’ve brought on, and the network of colleagues I personally collaborate with—all influence not only the quality of the work, but also the kind of business I’ve created.
Good working relationships come through solid communication, shared expectations, and a genuine commitment to delivering quality work together. When those things are present, trust is built. In turn, challenges are easier to navigate, collaboration is enjoyable, and the work itself is more rewarding.
The opposite is true, too. When there’s a fundamental mismatch in values, expectations, or working styles, even a promising opportunity can become unnecessarily difficult.
This is especially important in an agency, where success depends on understanding a variety of business models and industries, collectively bringing creative ideas to fruition, and weaving consistency through successive tiers of campaigns. The best results come when everyone is invested in both the outcome and enjoying the process.
You can’t always know from the beginning how a relationship will develop. But you can pay attention to how people communicate, how they handle challenges, and whether their actions match their words.
The lesson: Choose your clients, partners, and teammates thoughtfully. Invest in relationships built on mutual respect, and don’t underestimate the value of working with people who share your commitment to doing things well. A successful business is more than what you accomplish; it’s also about who you accomplish it with.
3. You Don’t Have to Have It All Figured Out to Get Started
Looking back over 25 years, one thing is clear: no amount of planning could have prepared me for every change the marketing industry would bring.
The tools have evolved, the ways businesses reach buyers have changed, and technology has introduced new possibilities, while also creating new challenges. What works today will look very different a few years from now.
That’s a reality of running a business in any industry. You can plan carefully, set goals, and make informed decisions, but you can’t predict everything that’s coming.
Early on, it’s natural to want certainty before making a move. You want the right plan, the right timing, and confidence that your decisions will pay off. This was the hardest lesson for me to learn, but waiting until we have every answer will keep us from making any progress at all.
I’ve made a shift in that regard. I start now with what I know, make the best decision I can, and learn as I go. After twenty-five years of doing this, I still remind myself that being nimble and flexible is the key. It allows us to adjust our approach, build on what works, and get more comfortable navigating the things we couldn’t have anticipated.
That doesn’t mean abandoning strategy or making decisions without thinking them through. It means recognizing that progress and learning often happen together. You’ll never have a perfect roadmap, so lean into that first, best step forward.
The lesson: Be thoughtful about your decisions, but don’t let the pursuit of certainty freeze you in place. Stay curious, remain open to change, and give yourself room to learn along the way.
Looking Ahead
Twenty-five years in business has reinforced that success rarely comes from a single decision, breakthrough, or big idea. More often, it’s the result of many smaller choices made over time: pivoting with opportunities, building strong relationships, and continuing to move forward even when the outcome isn’t known.
These lessons apply whether you’re launching your first business or leading a company that’s been around for decades. You won’t get every decision right, and the business landscape will continue to change. What matters is learning from experience and being willing to adapt.
If there’s one thing I’d tell anyone starting out today, it’s this: focus on building a business you’re proud of, surround yourself with people who make the work better, and don’t wait for everything to be perfect before you begin. The lessons you learn along the way and the people you share those experiences with turn out to be the most valuable part of the journey. Thank you to everyone who has been a part of mine!