A Twist On An Age Old Tale...Disguised Quest for Authenticity: A Wealthy Man Tests Charities

Apr 14 / Tamera Stewart
Each executive looked similar to the last; an expensive suit and well shined shoes, perfectly combed over hair, and, like the last one, this one had no idea what was at stake. If they only knew that greeting the man holding the door could bring in a donation worth millions of dollars, it seems they would have reacted a little differently. But that was the point.

Jerry held the door open for the next executive. This one was juggling two cups of coffee and a briefcase on one arm, while fervently typing on his phone with the other. Jerry, the old man in a disguise, quickly opened the office building door to lend the young executive a hand and with a smile he said ‘hope you find the peace you need at the end of the day’. The young executive looked annoyed and jerked the door away from the old man so as to not give him the satisfaction of holding the door open for him.

Jerry was not even surprised by this reaction for two reasons. First, he knew this was how he often reacted when someone he didn’t have time for tried to be polite. Second, as this was the third day he had been in this office complex trying to find an organization to leave his fortunes to, he was beginning to get used to it. He was surprised, though, when the executive returned with a building security guard to have him forced off the property for the crime of holding the door open and wishing the executive well. Jerry left without causing a scene, just silently shaking his head as only he knew what that action cost the young executives organization.

It turns out Jerry’s story is pretty typical. A man grows wealthy and old, alone. He prioritized gathering wealth and material items over anything else in his life. Retired now and getting up there in age, everyday things become more meaningful. For 20 years, he frequented a small coffee shop, his retirement routine unchanging until the shop's beloved barista—a woman who served him daily—passed away. Her death unnerved him in a way he never expected when a startling truth was revealed: she had been homeless.
Her death caused him to question more about his own life than any other event in all his seventy six years. So many questions and regrets flooded in. This brings us back to what led to his disguising himself and holding the door for young nonprofit executives. He decided to donate his fortune to help the homeless, hoping to make up for the way he had treated those less fortunate than him for so many years. Jerry meticulously researched and compiled a list of 16 organizations. Each appearing perfect online—successful, empathetic, and caring. Yet, he was unable to choose the right organization with online information only knowing it was potentially all a smokescreen. To uncover the truth behind these facades he embarked on a unique experiment.

His Plan Unfolds...

He dressed himself to fit the part of the very person these organizations purported to help and positioned himself on a park bench in an office complex brimming with nonprofits. The first day, Jerry observed quietly from the wooden park bench under the oak tree in the middle of the complex. He could see four different buildings, all modern architecture with a big glass front, yet it was mirror glass making it impossible to see in. Using his skills and considerable resources, he spent the day learning what he could about the organizations he considered donating his fortune to and their employees. He decided on the second day to interact with as many people as he could in front of one of the largest buildings in the complex. Jerry stationed himself by the building's entrance and greeted everyone—with only two of the 30+ reciprocating the greeting. Neither of those two were from the organizations he considered donating his fortune to.

Disheartened but determined, Jerry moved to another building the following day. This time, his presence wasn't just ignored; it was met with hostility. By noon, he was chased away by the executive he tried to help. And not one of the others in the building had been willing to look beyond his disguise to even return his greeting, the same as the day before at the other office building.

Refusing to give up, the fourth day he ventured a couple of miles down the road to a less affluent area, where smaller nonprofits resided. Here, his journey took a surprising turn. He hadn’t even checked into the online presence of any of these companies, it hadn’t dawned on him to look for the small ones as he assumed the largest were the only ones making real progress.


This is where I am going to cut off this week's story and leave Jerry’s world and return to our own. .
You and I know, of course, that he was wrong about only the large organizations making progress. In fact, I often see it being the small ones without a corporate agenda doing the most good. Think you know where this story is going? You'll likely be wrong…

But you have to wait and read next week's blog to find out.

While the obvious lesson of today's blog is about being a good person, the deeper insight relevant to your digital advocacy is about authenticity.

For those who followed my recent thread on X (formerly Twitter) on the benefits of maintaining separate social media accounts for personal and advocacy purposes, remember: authenticity is crucial in all spheres of online presence. If you missed this valuable thread, you can catch up here. This weekend's email focused on the pivotal role of first impressions in digital advocacy. Don't miss out on any more of these transformative insights—subscribe to our email list now to ensure you receive every tip-filled update directly to your inbox.

Today’s social media makes it easy for anyone to share whatever they want. It could be that they only share the best sides of their lives or that they lie completely. The problem is, digital advocacy is most effective when combined with boots-on-the-ground advocacy. So if your ultimate goal is policy change, success means you will eventually be standing in front of many of the same people you engage with online. If they happen to get a glimpse of you before you know they are looking, what will they see?

Will you be the executive who has the old man in disguise removed forcibly for opening the door and wishing you peace?

Or will you reciprocate and at minimum treat him as an equal?