Bike Trails and Boardrooms: Navigating the Learning Curve in Fundraising

I have another confession: I find endless inspiration—and metaphors for life and work—while riding my bike. And now, a fair warning: if you read my first blog post and are reading this now, you already know this isn’t the first (and definitely won’t be the last) bike-themed missive. So join me, and buckle up for another little story about two-wheeled transport, fundraising, and human nature.

This story begins in Girona, Spain, where I spent the past two glorious months. Most mornings, before the heat of the day set in, I was lucky enough to ride my gravel bike on the endless champagne (or should I say cava)-colored dirt trails. While I’ve always identified most strongly as a mountain biker at heart, I’ve made a (not-so-surprising) shift to gravel biking in this third quarter of life—for reasons that are probably obvious.

Still, upon returning home to Durango, Colorado, I was eager to get back on my mountain bike and enjoy the undeniable benefits of full suspension and the adrenaline of navigating our world-class technical trails. But within moments of hitting the singletrack, I was frustrated and disappointed—not in my bike, but in myself. After riding hundreds of miles on gravel, I found it difficult to steer, to engage my fast-twitch muscles, and to feel fluid on the trail.

It took a fair amount of self-talk to give myself some grace and remind myself that I don’t have to be “good” at everything. I needed to practice my way back into comfort on singletrack. It’s a vulnerable place to feel like you've taken a step backward.

That experience got me thinking about how much we, as adults, dislike discomfort. Over time, we come to rely on our strengths—whether it's cooking, organizing, public speaking, finance, research, or sales—and we tend to make small pivots that build on those existing skills. But acquiring an entirely new skill? That’s far harder. It requires us to start over, to feel exposed, to admit we don’t know.

And here’s where the analogy to fundraising comes in.

Very few of us instinctively know how to apply our skills in a nonprofit setting—especially in fundraising. No one is born knowing how to fundraise. Time and again, I’ve seen successful business executives try to transfer the same skill set that made them thrive in the for-profit world (gravel biking, in this analogy) into the nonprofit space (mountain biking, if you’re still with me). They’re often surprised—and frustrated—when those methods don’t work as expected. Their intentions are good, but they’re understandably uncomfortable asking for help with the shift.

Board members often bring a mindset of “I’m successful, and now I want to give back.” That can make it even harder to ask for support or admit a learning curve. Sometimes there’s a mentor available to guide them—but not often enough.

This is exactly where outside fundraising counsel comes in. Fundraising is the lifeblood of most nonprofit organizations—and one of the most difficult things to get right. External consultants provide something invaluable: a safe space for learning.

Time and again, I’ve had one-on-one conversations with board members who admit to the same frustrations—disappointment in results, reluctance to blame staff, and a sense of pressure to improve outcomes. They often feel stuck and occasionally, they admit their own uncertainty about how to fundraise effectively.

A good consultant provides more than technical expertise. They create a supportive, nonjudgmental environment where successful people can assess the situation and start building new skills. This kind of learning only happens when there’s mutual trust and the right chemistry between consultant and volunteer and staff leadership. Yes, it’s vulnerable to admit outside help is needed—but the right consultant can unlock not just stronger fundraising results, but personal and professional growth for everyone involved.

It’s an investment, no doubt—but one that delivers far more than just monetary returns.