Dare to Be Great
The lessons I’ve learned as a downtown manager over the past 15 years could easily fill a book, or probably several. But if I had to distill everything down to a simple message, it would be this:
Take risks, and make mistakes. Be open to unexpected surprises along the way. Dare to be great every day.
My career often seems to revolve around a pursuit of truth: what is it that this organization or this community needs more than anything else? My job is to identify those needs, then go about responding to them. But truth for one person can be nonsense to another. That’s where we need to have a discussion about interests. Our first job is to figure out in partnership with our community which interests are most important. And understanding those deep needs can lead us to the best opportunities to be great – the best moon shots we can take.
Sometimes those moon shots – the seemingly impossible challenges — yield the greatest breakthroughs. And often, the most fun, because we cannot do them alone.

During my first week on Long Island, where I had moved from Michigan to restore Teddy Roosevelt’s home town, the local paper announced that a historic building would be demolished. I grabbed my camera, went to the site, and took a bunch of pictures. Back in the office, I jumped on the Internet and learned that this was the Octagon Hotel, built in the 1850s. During Roosevelt’s time as Governor and President, numerous luminaries stayed there. This building was too important to be lost.
Over the next year and a half I worked with a diverse group of organizations and partners to persuade the owner that restoration was the best option. Ultimately we prevailed, and the building still stands today. The process, of course, was not without its bumps, but the results speak for themselves. Six new apartments were created, and three new retail storefronts. More importantly, this project sparked millions of dollars of additional public and private investment downtown .
Benjamin Franklin is reputed to have said, “Vision without implementation is hallucination.” On a weekly, if not daily basis, I have to remind our volunteers of that fact. The Main Street Four-Point Approach,® which the communities I work with use, relies on the work of volunteers on four grassroots committees.
In the communities I have worked with, I end up being as much ringleader as director . Early in my career, I took great pride in presenting my communities with great ideas and visions, but over time, I’ve come to realize that where communities need help the most is figuring out how to get their own visions into reality.
Recently, as Executive Director of a downtown program in eastern Kentucky, I had an opportunity to organize a Better Block event, where volunteers carried out inexpensive short-term interventions over a weekend to demonstrate the potential for long-term change. Over 100 volunteers from 18 states participated.

We reopened a theater that had been closed for 30 years and screened It’s a Wonderful Life. Pop-up shops filled vacant storefronts. And we built parklets that converted unneeded street parking spots into attractive outdoor public places for people to gather. We had such fun that we’re planning another Better Block as soon as we can.And this is just the beginning. In the years ahead we hope to incrementally improve and strengthen the local economy, create over 1,000 jobs, build a trail system for our community that connects us with communities as far away as Chattanooga and beyond, and bring about the much needed restoration of this community’s natural resources, cultural resources, and infrastructure. The challenges facing a rural Kentucky city are huge, but we have a strong sense of direction, our path has been clearly laid out, and the chances of success are good.
Lewis Mumford once wrote that “culture is cumulative.” The work that every one of us does every day determines how the environment around us is going to be — locally, regionally, nationally, and globally. Want places that are great, vital, full of activity and full of life? Then be prepared to give the full measure of your knowledge, resources, and abilities to make that happen. And strive to enlist a small army of people in support of the effort.
While the challenges we face today can seem impossible, there is a certain beauty and opportunity that comes with the time we are in. There is a necessity to ruins.
Even when we as individuals, communities, or our whole country are at a low point – this is when renewal and restoration begins. Those who want to make communities that are stronger and more resilient must be committed to that task every minute of every day . Unceasing labor, sacrifice, and service is the surest way out of the national funk we are in.
President John F. Kennedy probably said it best:
“I am certain that after the dust of centuries has passed over our cities, we, too, will be remembered not for victories or defeats in battle or in politics, but for our contribution to the human spirit.”
U.S. President John F. Kennedy
So go out your door every day with your head help up high, and take those moon shots. When you encounter setbacks along the way, take them in stride and keep pushing forward. This is the American tradition, after all.
And, this above all else – never, ever, ever give up. Our families, communities, and, indeed, the whole future of our country depend on you daring to be great.
Published in Why This Work Matters: Wisdom from the People Who Are Making Communities Better, Wise Fool Press, edited by Della Rucker (March 31, 2014)
Why This Work Matters introduces you to the voices of 11 people who are doing the hard work of making communities better. They work in local and state and federal organizations, in governments and nonprofits, in planning, economic development, city management, downtown revitalization and more. In their own words, as clearly and honestly as they can put in writing, you’ll hear how they manage the frustrations of this work — how they deal with political realities, with shortcomings, with bureaucracy and discouragement. And, maybe more importantly, you’ll hear what they draw on to summon the courage and the bravery to keep at it.
