What People Regret Most: The New York Chalkboard Experiment

A New York Chalkboard Invited Strangers to Share Their Regrets

When strangers on a New York street were handed chalk and asked to write their biggest regret, almost every answer had the same small word in it: not. Not going to medical school. Not telling someone they loved them. Not spending enough time with family. Not taking the chance. The experiment, filmed for a video campaign by Strayer University, became a viral reminder that the things people regret most are usually the things they never tried.

It is a simple idea, and it matches what psychologists have found in decades of research on regret. Here is what happened on that sidewalk, what the science adds, where the video oversimplifies, and how to turn a regret into something useful.

What strangers wrote on the chalkboard

For one day a large chalkboard stood on a sidewalk near Lieutenant Petrosino Square in Manhattan, with a single prompt across the top: write your biggest regret. Passers-by stopped, thought for a moment and wrote.

Nobody wrote about a car they failed to buy or an apartment in the wrong neighbourhood. The answers were about people and paths: damaged relationships, staying silent when they should have spoken, not telling loved ones how much they cared, not pursuing a medical career, not being a better friend or husband, not making the most of each day, staying inside a comfort zone. As the board filled up, the word “not” ran through it like a thread.

(The video originally embedded here is no longer available on YouTube.)

The clean-slate twist

The second part of the film is what made it memorable. Participants were handed an eraser, and the board was given a new heading: “Clean Slate”. One by one, people wiped away what they had written. One young woman became emotional as she erased hers and said she felt hopeful, because it meant there were still possibilities.

The message was deliberate. Most of the regrets on the board were about things not yet done, and many of those can still be done, at least in some form. A person who never applied to medical school may not become a surgeon at 50, but they may still study, volunteer in health care or find another way into the work they care about.

What research says about regret

The pattern on the chalkboard is not a coincidence. Psychologists Thomas Gilovich and Victoria Medvec, in an influential 1995 paper, found that people’s regrets change over time. In the short term, regrets about things we did, a harsh word or a bad decision, sting more. Over the long term, regrets about things we did not do grow larger and last longer. Looking back over years, inaction tends to dominate.

Researchers have also asked which areas of life people regret most. A 2005 analysis by Neal Roese and Amy Summerville, drawing on nine studies mostly from the United States, found that education topped the list, followed by career, romance and parenting. Their explanation was that people regret most where they still see opportunity, the areas of life where change feels possible. That neatly explains the medical school answer on the board.

A 2018 study by Shai Davidai and Thomas Gilovich added another layer. People more often regret failing to live up to their “ideal self”, the person they hoped to become, than failing to meet their duties and obligations. In other words, the deepest regrets are often about dreams set aside rather than rules broken.

The regrets of the dying, and their limits

The same theme appears in Bronnie Ware’s widely shared book The Top Five Regrets of the Dying. Ware, a palliative care worker in Australia, wrote down what her patients said near the end of life. The most common wish she reported was to have had the courage to live a life true to themselves rather than the life others expected of them. Others included wishing they had not worked so hard, had expressed their feelings, had kept in touch with friends and had let themselves be happier.

Ware’s list is a set of personal observations rather than a scientific study, so it should not be read as a measurement of what everyone regrets. But it lines up well with the research above and with the chalkboard: what people mourn most is a life left partly unlived.

Reading the video with a clear eye

The chalkboard film was a promotional campaign for a university, and it was edited to tell a story. Only people willing to stop and write took part, and viewers saw a selection of their answers. So it is a moving illustration, not a survey. The original headline claim that “they all used the same three-letter word” is close to true for the answers shown, but it is not a statistic.

It also helps to remember that regret is not purely negative. Psychologists see it as a signal: it points to what matters to us and can motivate change. Regret becomes harmful mainly when it turns into endless rumination with no action. If regret or low mood starts to weigh on daily life, talking to a doctor or a qualified counsellor is a sensible step.

Turning a regret into a next step

Write it down specifically. “I never followed my passion” is vague. “I stopped painting when I started working” gives you something to act on.
Separate the closed from the open. Some doors really have closed. Many have only narrowed. Ask what a smaller, realistic version of the missed path looks like today.
Say the unsaid thing. A large share of the chalkboard regrets were about words not spoken. A message, a call or a letter can still be sent to many of the people involved.
Take one small step this week. Sign up for a class, call an old friend, ask about a course. Action is the most reliable cure for regret about inaction.
Be kind to your past self. Decisions made with less information or under pressure were often reasonable at the time.

The chalkboard’s lesson is a gentle one. Most regrets are about chances not taken, and while you are still here to read about them, some of those chances remain open.

Sources: Preaching Today: description of the Strayer University regret chalkboard video; Upworthy / A Plus: New Yorkers share their biggest regrets on a blackboard; Wikipedia: Regret (research summary, incl. Gilovich and Medvec 1995; Roese and Summerville 2005; Davidai and Gilovich 2018; Ware 2013).

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