The Dao of Doctor D

Timeline Thinking: 10 Questions to Support Ad-Hoc Decisions Timeline

Ted strolls across the grass, sweat glazing his forehead, the sound of staticky 1980s-channel radios echoing in the near distance. Beneath the flea market tarpaulin, he passes many items that are junk to him, until he spots one of interest. He recognizes the style of the old dresser. The finish shows bare wood in many spots and a crack runs along the grain of a side panel, but Ted’s familiar with how to fix those issues. He opens the drawer and sees the maker’s stamp he expected. A citrus-like wood smell reminds him of long days as a boy watching his father make grandfather clocks in his shop. If this dresser is what he believes it is, the price on the card is about 20% low for its condition. He asks the gray-haired, bespectacled woman at the stand for her best price. She comes down 20% from the card—”can’t go any lower”—but mentions that her and her husband are packing up soon to leave. They have dinner with friends that evening. Ted steps back to assess the dresser in full form and rubs his chin. “Should I buy it?”

Ted must travel in time, then he would see where the builder created this piece and who bought it first. He would see every stop of its 150 years that brought it to this point in time. Ted would read the woman’s mind to learn if she was leaving early or just pressuring him. He’d learn what she wasn’t saying about the dresser. Ted would see the problems he might have restoring it and the profit he would make selling it to the right person. 

Ted SHOULD travel in time. That time machine is within him. We all know he can’t travel in physical time. But he can take a mental journey and create a useful timeline. It’s something I call “Timeline Thinking.” If Ted applies it with all its imperfections, he’ll be able to make a stronger decision. As Ted stands there on the brink of his decision, he should ask past, present, and future questions and get the best answers he can get in the time he has to decide. 

As we talk about time, we think past then present then future. (It’s astronomer Arthur Stanley Eddington’s “arrow of time.”) When we apply timeline thinking, we start in the present with the decision to apply the approach and the actions of applying it. Since predicting the future is best when supported by our understanding of the past, the sequence is present, past, then future. Applying timeline thinking is not a single straight line, but circular, happening in iterations boxed by the time available and the tolerance for the risk of making the wrong choice. Ted can choose from many questions, exercises, and tools to support his decision, but here are ten he can apply. 


  • What decisions is he making?
  • How long remains to analyze this decision?
  • What information resources does he have at his immediate disposal?


  • What can he learn about similar objects or decisions?
  • What does he already know about similar objects or decisions?
  • What has he learned of the object and context of the decision since its discovery?


  • Given what he knows, what are probable outcomes?
  • Which outcomes present the most risk?
  • Are there outside forecasts that can add support to a prediction?

The Informed Present

  • Can he accept the risks of taking action with what he understands of past, present, and future?

This whole sequence of questions leads back to a new, informed present. It can happen in an instance—and often does with experts. It could also take years, with complex and high-risk problems. The process usually repeats. I will explore each of these ten questions coming posts. I expect that I will also refine these questions as we explore this topic in the coming years. 

Apply this idea of having a canned set of questions to explore decisions and actions on-the-spot based on the context of the present, the lessons of the past, and predictions of the future. Let me know if your set of questions works better for you. As with most inventions, we improve them through use and applying what we learn to improve them.


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