Kyle Scheele is the opening keynote speaker at the 2025 NBOA Annual Meeting, which will be held February 23-26 in New York City. Scheele has been called "the patron saint of crazy ideas.” Whether he's holding a Viking funeral for the regrets of 21,000 people, hosting the world's first fake marathon, or gaining a million TikTok followers in just 25 hours, Scheele is always on the lookout for crazy ideas that produce wildly outsized outcomes. Over the last decade, his projects have been featured in outlets like Fast Company, WIRED, The Washington Post, BuzzFeed and more.
NBOA President and CEO Jeff Shields interviewed Scheele for an upcoming episode of the Net Assets podcast, which will be released in December. The following is a short excerpt from that audio interview.
Jeff Shields: My understanding is that you're an innovation expert who's known for cooking up outlandish ideas that people love. You were invited to be our opening keynote at the NBOA Annual Meeting because it's important to encourage our members and others who work in pre-K through 12 independent schools every day, who are responsible for the business finance operations, to think differently.
Kyle Scheele: That's always my goal, to get people to tap into their own creativity. I firmly believe that there's no such thing as a not creative person or an uncreative person. I think all human beings are creative, but a lot of us get into the habit of not exercising that muscle.
Shields: If you go into a room of CFOs, HR professionals and controllers, and you ask them to raise their hands if they think they're creative, how many hands do you think will go up?
Scheele: I think people are very reticent to say, “Yes, I'm a very creative person.” If you go into a room of kindergarteners and ask that question, every one of those hands goes up into the air. And then when you come back and ask those same kids in later grades, as the years go up, the hands come down.
It's cute when a kindergartner says they want to be an artist when they grow up. But when a senior in high school says that, our first response is, 'Have you looked at the job market for artists out there? How are you going to use that degree?'
I think the reason is because as we get older, there's this pressure, externally and also internally, to conform, to be reasonable, to give up on that dream and pursue something that's a little bit more achievable. You know, it's cute when a kindergartner says they want to be an artist when they grow up. But when a senior in high school says that, our first response is, “Have you looked at the job market for artists out there? How are you going to use that degree?” And we start applying these practical questions. Those can be good, but what they do for most of us is cause us to hide that part of ourselves, pretend that it doesn't exist.
I also think as a society, what we've done to justify that is, we've said only certain things count as being creative. So we think it's creative if you paint a picture, it's creative if you build a building or make a sculpture or choreograph a dance or something like that. But putting together a financial plan isn't creative or making sure that the org chart works isn't creative. We’ve decided these things don’t count, but they are creative, they do count. Anytime you make anything new, it's creative. Opening a new Word document is a creative act, but we've decided it's not.
And so I think that's part of why you end up with a situation where someone's been in a job, you know, for 10, 20, 30 years doing this thing, and they say, “I'm not creative because I don't think of this job as creative.” And society has said, “Yeah, we don't think that either.” But it’s not true.
Shields: Our audience, business leaders at independent schools, are known as people who hold the school together with strong financial stewardship and operational acumen. They are level-headed people, who are trustworthy. How are you going to challenge this audience to “get crazy” and think along the lines of some of the activities that you've undertaken, which are quite out of the box?
Scheele: First of all, I think crazy is in the eye of the beholder. Something that might seem crazy to me might not seem crazy to a person who's been in that role for a period of time.
What I want is not for people to try to be like me. What I want is for people to ask, how can I expand my window of possibility here? What are the solutions that are on the table that I'm not looking at because I have been myopically focused only on the thing that I've always done? What other opportunities are available? What other sources of funding are out there? What other business models exist — or could exist? Where can I look outside of just this industry for inspiration?
Steve Jobs once said that creative people often feel guilty because they feel like they didn't actually do anything, that they just noticed a connection between two things. Connecting the dots — that's all that creativity is.
Steve Jobs once said that creative people often feel guilty because they feel like they didn't actually do anything, that they just noticed a connection between two things. Connecting the dots — that's all that creativity is. It’s figuring out if you take this thing from this other industry and this thing that no one's ever thought to put together before, and ask what if you did this?
Shields: So how can we tap back into that inner creative child that a lot of us were taught to ignore? It’s interesting because we all know that innovation is so necessary in all industries. You can't think of just what's happening today; you have to think of what's next, about the future. Why are there so many stumbling blocks in organizations for innovative idea generation? Why do we struggle with that?
Scheele: There's a quote that says, "Nobody ever got fired for picking IBM." And I think that that's true in its own way. Meaning, nobody ever got fired for maintaining the status quo. The status quo exists for a reason. You don't have to defend that reason because it's just like, we're already doing this, so somebody must've had a good reason for doing this.
We forget that, no, actually, this was just a new idea at some point. We tried it, it worked. There are pros and cons to it. But because it's what we're doing now or what we have been doing, we're comfortable with it, and we think there's no reason to change anything. The way that we do fundraising, the way that we do our educational system, it all started somewhere. It started with an idea that probably seemed pretty crazy at the time and turned into something that we're now comfortable with.
There’s a time for not shaking up the boat too much, but I also think that there's a time to go, hey, we got here by shaking up things. How are we going to get to the next place? Probably by shaking some things up again.
Shields: I think when you speak in front of this audience, folks will be ready to embrace something different. They're ready to think differently. They're just not quite sure how to navigate it. Do you have any advice in that regard?
Scheele: Yes, and we'll get into some of that in the talk.
Learn more and register for the 2025 NBOA Annual Meeting, which will be held February 23-36 in New York City.
