Why a Streak of Setbacks Is Often the Right Path

A company is not valued on the cash it generated in the past. It is valued on the cash it will generate in the future. The same logic applies to a career, yet most people reverse the equation. They spend 95 percent of their thinking time on past disappointments and 5 percent on what comes next, then wonder why nothing changes.

A member of the new Setbacks and Failure program wrote in with a question that looked simple at first glance. How do I rebuild forward momentum after an extended streak of setbacks, when conventional advice like starting small and focusing on prior wins is not working?

Michael unpacked the question. What is an extended streak of setbacks? What counts as forward momentum? Are you going backwards, are you standing still, or are you moving slowly? Each one is a different problem with a different answer. The quality of your question determines the value of the answer you get.

There is the path you take and there is the result you get on that path. If you chose the right path and did not get the result you wanted, that is not a setback. You are still learning. If you chose the wrong path and did fairly well anyway, that is the real danger, because a wrong path eventually corners your career no matter how good the numbers look.

Michael used a client he calls Mary. Mary sat on the management committee of a major investment bank. When she had her child, the firm offered her a new business to run on her own terms, three or four days a week, mostly from wherever she wanted. At the time, it was the right decision. She got a P&L. She got the life she wanted. She kept building her career, even though part-time. Three and a half years later, her career had not moved the way she hoped, so she looked back and called those years a streak of setbacks, the same wording as the Legacy client used. They were not setbacks. She chose the right path for her at the time. She just did not think through what she would lose; she focused on what she would gain. Relabeling the path as a failure is an emotional lens, and it is the thing keeping her stuck because she is not learning the right lesson.