Fear, negative visualization and expected outcomes

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Fear, negative visualization and expected outcomes

Platitudes and one-dimensional tips are super lame.


  • Fortune favors the bold.
  • Carpe diem.
  • Just do it.

I was recently co-presenting a workshop on the subject of risk-taking: daring to be brave and embracing the right opportunities in one’s career.

The first thing my co-host and I did was introduce our respective backgrounds. She was a corporate worker turned life coach and fitness guru. I am a corporate worker turned entrepreneur. We shared not-entirely-dissimilar backgrounds in terms of venturing into autonomous/independent roles.

A question came up for us—and I don’t recall the exact wording—but it amounted to: how do you tell yourself to take risks in your life/career, when there is a decent amount of reservation and/or fear holding you back?

In the context of a workshop in which we are expected to puff out our chests and say “just do it, fortune favors the brave!”, et cetera, I stopped myself. I fought the temptation and ease to resort to the same old platitudes.

Instead, I offered my answer in parts:

  1. Everyone has a different threshold of risk. Don’t compare yourself to others. It might personally take me more effort to be “as brave” as someone who can day-trade stocks in their sleep. It’s all about internal benchmarking and improvement.
  2. Risk-taking is a muscle that should be developed and improved over time. Today you take 2% more risk than before, so that next week you can take on 5% more risk. (Timeline is arbitrary.) It’s an incremental process. Again, compare yourself to yourself and not to others.
  3. Taking risk is an internal calculus, no matter how big or small the “thing”: if we feel that the potential expected outcome is worth the trepidation, then we’ll do it. Example 1: I might be scared to network or talk to someone. But if I feel that there is something potentially rewarding from the conversation, then I’ll do it. Example 2: if I feel scared to change jobs, then I won’t do it unless the new job is significantly better in some respects. Simply put: if I don’t see the potential reward, then I won’t do it.
  4. Saying to myself, “be brave, James—do it!” will get me to do something in the short-term; I can fool my brain into making the jump. But it either won’t be sustainable, or I’ll quit easily, unless I can find the true “why.” Be honest with the internal calculus, or it will just be a trick and not a strategy.
  5. Negative visualization—the art of imagining “what’s the worst that could happen?”—is essential. I’ve done many things in my life and career after imagining the “worst case scenario” and realizing it’s not that bad. Example: quitting a corporate job to found a startup. Once we realize that startup failure simply means going back to the corporate job, and that the only true “loss” is opportunity cost, then the risk-taking calculus is better rounded out.

The overarching point here is to develop a system for decision-making that is personally tailored to work for YOU, and to make the decision-making process repeatable. Write down your process to test whether it’s coherent and robust enough. (If you can’t do it, that’s likely a warning sign.)

Let me know how you make risky decisions. Do you have a similar model, or do you have something way cooler? Would love to hear from you.

Take care of yourself, and be well.


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Add yours →

  1. Hey James! Great read! I would say that it is very hard to create one method and repeat it in all the decisions we have to make but simple pros and cons charts is always a good start for me. “Risk-taking is a muscle” So do you think we should challenge ourselves to take more risks in life as we may lose this ability over time?


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