Two days before the first Finding Meaning in Work workshop in April, I had sold one ticket.
Andy’s ticket. I sent him a sheepish email explaining the situation. I could run the workshop as a one-on-one session, or give him a full refund. I did not want him to arrive on Saturday expecting a group and find just me. Before he could respond, two others booked. There would be three people in the room. The workshop could go ahead.
But the question stayed with me: why had Andy booked? The workshop cost $275 and took up four hours of a Saturday. There were no testimonials, photographs or stories from previous participants. This was the first time I was running it. Finding Meaning in Work was a name, a description and a promise from someone who had never run it before.
Andy and I knew each other, though not especially well. We trained at the same gym and occasionally did a slightly absurd group fitness class that involved carrying kettlebells to a café, having coffee and carrying them back. During those walks, our conversations sometimes moved beyond the usual subjects. He also read this newsletter and had written to me about a few essays that connected with him. So, he knew something about the person behind the workshop. He could not know whether the workshop itself would be any good.
Crossing the Gap
Charles Feltman defines trust as “choosing to risk making something you value vulnerable to another person’s actions.”
Andy was making several things vulnerable. The obvious ones were his money and time. Less obvious was the hope contained in the purchase. A workshop about meaning asks people to bring questions they may not have been able to answer on their own. If the experience was shallow or poorly held, the disappointment would reach beyond the price of admission.
Douglas Hubbard makes a useful distinction between uncertainty and risk. Uncertainty means that more than one outcome is possible. Risk appears when some of those outcomes involve loss.
Andy was uncertain because he did not know what would happen in the room. That uncertainty became risk because the afternoon could waste his money and time, or leave him feeling that questions he cared about had been reduced to another superficial workshop. Trust did not remove any of this. It allowed him to act while some uncertainty remained.
Rachel Botsman describes three barriers that make this kind of trust leap difficult. The first is social proof. We are more willing to try something when we can see that others have already gone first. The second is loss aversion. We tend to feel the pain of losing something more strongly than the pleasure of an equivalent gain. The third is what she calls the law of familiarity. People may be attracted to novelty, but when trust is required, they are more comfortable with the familiar done differently than with something entirely unknown.
The workshop had no social proof. Andy had several reasons to avoid the possible loss. What it did have was familiarity. He had read my work. We had spoken. He had some basis (however small) for believing that I would take the subject, and him, seriously.
Before a new piece of work has evidence of its own, it often has to borrow trust from its maker. But someone still has to go first.
The Responsibility of Trust
Andy’s booking created an obligation before the workshop had even begun. It can be tempting to believe that being trusted makes us responsible for delivering the outcome another person wants. But most outcomes are never entirely within our control.
A doctor cannot promise that a treatment will work. A leader cannot guarantee that a difficult decision will succeed. A friend cannot take away another person’s grief. What they can control is whether they act with honesty, competence and care.
To be trusted is not to become responsible for an outcome you cannot control. It is to become responsible for how carefully you handle what another person has placed in your hands.
Andy had placed his time, money and hope in mine. I could not guarantee that the workshop would transform his relationship with work. I could prepare properly, take the material seriously and create an environment in which he felt able to examine questions that mattered to him.
One exercise asked participants to return to an early spark: a childhood experience that, with hindsight, offered a clue about what had always mattered to them. Andy connected with a memory that helped him see something in his present work more clearly.
I had designed the exercise, but I could not manufacture that recognition. The other participants also had to decide whether to speak honestly, listen carefully and treat what was shared with respect. I could prepare the room for that, but I could not control everything that happened inside it.
This is the responsibility that comes with being trusted. We owe people honesty about what we can offer and what we cannot. We owe them care with whatever they make vulnerable. And when the outcome falls short, we owe them the willingness to listen, learn and do better.
The thing AI cannot build
I spend much of my working life with early stage founders. Unlike a few short years ago, producing the first version of something is not their hardest problem. With a few well-worded prompts, someone can produce a convincing website, a working prototype or the beginnings of an app. That's now the easy part. What is a lot harder is being worthy of holding what is valuable. That question becomes even more serious when the product touches our health, money, personal information or livelihood. The ability to build an app does not establish that the founder understands the person who will use it. It does not prove competence, judgment or care.
This is why I often wonder whether founders could help people directly before building the technology. Could they get into a room with them? Could they solve part of the problem manually? Could they listen long enough to understand what people fear losing? Can they give people a chance to experience the founder as a person before being asked to trust a product with no history.
Becoming trustworthy is slower work. It goes against our natural tendencies to find the most convenient route. But as social entrepreneur Zita Cobb says “If there’s a hell, the road to it is paved with frictionless convenience”
Trust, however, has limits. It may persuade someone to take the first step, but it cannot make the work relevant, useful or worthy of continued belief. Andy’s purchase did not prove that the workshop worked. It gave the workshop a chance to earn the trust he had already extended
What I know is that every new venture begins before the proof is complete. Someone makes the first purchase, accepts the first invitation or places the first untested product into their life.
Receiving that trust is only the beginning. The real work is becoming worthy of it.
