As I continue to process Jack Dorsey’s announcement last week that his fintech company, Block, would immediately lay off 40% of its 10,000 employees because of the company’s aggressive adoption of AI, I’m reminded of an important lesson I’ve learned from working with dozens of executives over the years.
It’s easy – but risky – to confuse what we do with who we are.
When we confuse our doing with being, we often find ourselves compelled to meet others’ expectations of what work we should pursue rather than finding work that’s deeply meaningful to us. To borrow Mark Nepo’s metaphor, our professional lives come to resemble a speeding train that is running on tracks laid down by others. Our careers accelerate, our lives become a blur, and we miss the subtle hues and textures of life, the beauty and the mystery of the world around and inside us that is our inviolable birthright.
After one of my clients lost his job and became desolate because of the length of his job search, I suggested he take a pen and piece of paper and complete the sentence beginning with “I am…” as a homework assignment.
He later admitted to me that this was the most difficult sentence he had ever written. It had taken him two weeks to complete a first draft. Finally, when he read me the sentence he had written, he broke into tears. He feared, he confessed, the regret that might consume him at the end of his life from not pursuing work that reflected his most deeply-held values.
“What am I longing for?” is a question Susan Cain, in her most recent book “Bittersweet,” suggests we ask ourselves as a way to discover what’s most meaningful to us in life.
It’s a powerful question to ask when we find ourselves feeling adrift after a layoff, or when we voluntarily leave a job after realizing we can no longer work for an abusive boss or a company whose values we can no longer support.
Reorganizations and layoffs will accelerate in the weeks and months ahead as, in Dorsey’s words, AI tools enable “a new way of working which fundamentally changes what it means to build and run a company.”
Now is the time to pause and ask ourselves, “What am I longing for?” Now is the time to remind ourselves that the work we do should serve who we are, not who other people believe we should be.










