Why Dreaming Big Might Be Holding You Back: Jeff Hilimire (Transcript)

Read the full transcript of Serial company builder and nonprofit founder Jeff Hilimire’s talk titled “Why Dreaming Big Might Be Holding You Back” at TEDxAtlanta, June 25, 2025.

Listen to the audio version here:

The Problem with “Go Big or Go Home”

Jeff Hilimire: Have you ever been told, either by a coach, or a business leader, or a motivational book to go big or go home? Ever been challenged in your work to create one of those BHAGs, a big, hairy, audacious goal? I used to be one of those people, chasing my own big dreams, and, as a leader, telling my teams to climb the mountain, or reach for the stars, or grab the bull by the horns. It’s true, I was a hard-charging, beat-the-competition, and wow-everyone-with-your-impressive-results kind of person, until I realized that was all a load of crap.

My Entrepreneurial Journey

See, I started my first business before I even left college, launching me into a career of successful entrepreneurial ventures. After building my first company for ten years, moving from the dorm room to my mother’s basement, to the back of a fitness center, and eventually to a high-rise in downtown Atlanta, we were lucky enough to successfully sell the business. My partners and I then started our next company, and after five years, we sold that business.

During that 15-year run, we were on all the important lists in town, including the coveted fastest-growing companies and best places to work, and we had all the marquee customers. We outgrew the competition and dominated the award shows. So why wasn’t I happy?

The Search for Purpose

As I began to think about what I wanted to do next, I was struck by this nagging question. What was the point of it all? I felt unfulfilled and underwhelmed, even though I had followed society’s formula for success. For the first time in my life, I hit the brakes on my career and took stock on the impact I was making in the world.

I reflected on the people that I used to admire, what’s called them titans of industry, questioning why I had admired them in the first place. Because they scaled their business and crushed their enemies? But to what end? Was that all I was doing, competing with everyone in a race that I had conceived of only in my head, trying to be the biggest and best simply because I felt compelled to reach for the stars?

I felt empty inside, as if nothing I was doing was going to make a positive difference to anyone other than me and my family. I desperately needed my life to stand for something. I didn’t know it, but I was on the hunt to find purpose in my work.

A Small Beginning

After selling the second business, I started my third company, a digital marketing agency. Around that time, I’d also joined the board of a local small non-profit, and in a board meeting it was decided that the organization would need a new website and would need it quickly for an upcoming fundraising event.

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I took the idea to my team, and we had a healthy debate about whether or not to take on the project. I pointed out that we’d be helping a charity in need, and they pointed out that we were already extremely busy, that the timeline on the project was unreasonable, and we’d be doing it for free so it would strain our finances. So we compromised and did the project.

I learned later there’s a term for what I did that day. Apparently I voluntold them that we’d be doing the project. I can tell by your reactions, some of you have been voluntold by your boss before. Apologies on behalf of bosses everywhere.

However, it didn’t take long for my team to see the power of using their skills to help others. They loved the process and were eager to find other organizations to help. And as my team felt a spark of meaning in their ability to help the non-profit, I felt a spark of meaning in my ability to give them that chance. And having tasted a tiny bit of purpose in my work, I wanted more.

Dreaming Small

But I could only push my small team so far on this idea. Or rather, I could only voluntold them so many times. No, if I wanted more, I would have to recruit others to join the cause. The idea that began to form in my mind was to connect a small team of web designers with a small non-profit and have them build a website quickly as my team had done. Websites need help now, and I knew that when creatives were pushed to execute in a relatively short period of time, they often do their best work.

I thought, if five or six people could build a website, let’s say in a weekend, why not invite more teams? I also knew that large groups can accomplish a great deal more together than apart, so why not invite more people? I thought if five people could build a website in a weekend, well then, ten could build two websites and twenty could build four websites, and I kept doing that math until I got to forty-eight websites.

At that point, I took the idea to other agency leaders in town to see if they’d be interested in having their teams participate in an event to attempt to build forty-eight non-profit websites in a weekend. And one by one, they told me the same thing. It would be near impossible to build one website in a weekend, but to build forty-eight in a weekend? Well, that was just insanity.

However, as the agency leaders turned me down, when I would have a chance to speak with people on their teams, they were all for giving it a chance. Well, that was all the encouragement that I needed.

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The Birth of 48in48

I grabbed one of my best friends, and in October of 2015, we’d be inviting people to an event to attempt to build as many non-profit websites in a weekend as possible.

And amazingly, several hundred people showed up. We split them into small teams and sent them to work on that Friday afternoon, many of them spending the entire weekend at the venue. And by some miracle, by Sunday at 6 p.m., we had built forty-eight non-profit websites.

There’s more. Think about the scope of that, though. Literally hundreds of people came together, worked for forty-eight straight hours, building forty-eight non-profit websites. If my initial idea had been that grand, I likely never would have attempted it. It would have seemed too unwieldy, too large of a concept to try to tackle. Instead, I was lucky enough to start by dreaming small. The initial idea for my team to build a small website, quickly, was something I could wrap my head around. It was only after successfully executing on that idea that I allowed the concept to grow into something larger. And I never could have imagined just how large of an idea it would become.

The Moment Everything Changed

On the Sunday afternoon of that event in 2015, I was sitting at the registration desk, and I was about to go check on the teams to see how they were doing with their websites. I had been at the venue since early Friday morning, having slept a few hours each night in a sleeping bag on the floor, and was running on fumes and way too much coffee.

Just then, a young volunteer stumbled up to me, looking exhausted, as tired as I felt, and said the most incredible thing. He said, “Can I put my name on the list for next year’s event? I don’t want to miss out.”

After I got over my initial shock, because I had never dreamed, definitely never said that we’d be doing this again, I thought, the kid’s delirious, he’s exhausted, he doesn’t know what he’s saying, I should humor him. So I grabbed a piece of paper, I wrote 2016 event at the top, and told him he could put his name and email address on the list, and should we have an event next year, I’d make sure he made the cut. I then left to go begin checking on the teams.

I came back 45 minutes later, the piece of paper I’d given the young man was completely filled out, and someone had grabbed a second piece of paper and it was completely filled out. Apparently, word had spread that there was a sign up for next year’s event, an event I had never said was happening, and over 50 people had signed up. These were exhausted volunteers that had spent the entire weekend away from family and friends, working as hard as possible to help others, and they wanted more.

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At that moment, I realized something that would change my life from then on, what we had created was not a way to help non-profits, though it surely did, what we had actually created was a way for people to use their skills, or their superpowers to do good, bringing more meaning into their lives, and allowing them to feel pride in their work, many of them for the very first time, and so, 48in48 was born.

The Growth and Impact

The next year, we actually had two events, the year after that four, then six, and the volunteers kept coming, and we kept growing. The camaraderie and enthusiasm at a 48in48 event is something you have to witness to believe with one volunteer even creating branded 48in48 shoes.

I still can’t believe that this past October, we celebrated our 10-year anniversary. During that time, we have held 35 events. Our volunteers have consumed 340 pounds of coffee, building 1,300 non-profit websites, with 7,500 volunteers contributing 300,000 volunteer hours, all of that equating to a global estimated impact of over $300 million.

The Power of Dreaming Small

We want to feel a sense of purpose and impact, and know that we’re making a positive difference. We all have different dreams on how to accomplish that. In most cases, our dreams begin as those classic, big, hairy, audacious goals. I’m here to tell you, that’s a mistake.

Everyone will say, dream big and swing for the fences, but I’ve come to learn that dreaming big just might be what’s holding us back from pursuing our dreams. My time building 48in48 taught me that we can use our skills, or as I call them, our superpowers, to do good, and we can change our lives, and in some cases, change the world. Only we have to have manageable dreams and goals.

We must stop believing that our contribution is too small to be meaningful, and instead think even smaller. So the next time you feel like your work doesn’t matter, or you’re unfulfilled and underwhelmed with your place in the world, do me a favor. Think about your dream, make it a little smaller, and then get to work, because the world is counting on you.

Thank you. Thank you.