At the beginning of the year people talk a lot about habits.
What if we talked about our fears?
What if we intentionally defined those Things That Must Not Be Named?
Tim Ferriss, a bestselling author and productivity thinker, talks about fear-setting. He outlines several questions to take yourself through.
Here is one that is particularly useful when thinking about finances:
What are you putting off out of fear? Usually, what we most fear doing is what we most need to do. That phone call, that conversation, whatever the action might be—it is fear of unknown outcomes that prevents us from doing what we need to do. Define the worst case, accept it, and do it. I’ll repeat something you might consider tattooing on your forehead: What we fear doing most is usually what we most need to do. As I have heard said, a person’s success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have. Resolve to do one thing every day that you fear.1
What fears are you avoiding? Here are three common ones in finance:
- You may fear investing in stocks because of the volatility and being afraid of losing money.
- You may fear talking about money with those you love because of shame or self-sufficiency.
- You may fear setting up a trust or naming beneficiaries, trustees, or executors because you don’t want to talk about death.
If you don’t do some of those things, some of your fears will come true anyway.
Money never just sits there. Inflation eats it. Don’t think not investing is neutral and safe.2
You may not want to talk about money, debt, investing, or inheritance. But conversations will happen—either when they’re impossible to avoid, or when you’re not here to have them.
One of the hardest things in life is realizing that indecision is a decision.
Ferriss nailed it: “What we fear doing most is usually what we most need to do.”
How do you start? Take one step. Start small. Start now.
It does not mean the fear will go away, but it does mean you will face it courageously.
Begin this year by kicking fear in the teeth.
You may not knock the monster’s head off, but you might knock out a tooth.
Who knows? Maybe setting that fear and facing it will ignite habits to swing again and hunt down other members of the horde.
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Sources:
- “Fear-Setting: The Most Valuable Exercise I Do Every Month”, May 15, 2017. Accessed online: https://tim.blog/2017/05/15/fear-setting/
- JP Morgan Asset Management, “Guide to the Markets” (October 31, 2025). Accessed online: https://am.jpmorgan.com/us/en/asset-management/adv/insights/market-insights/guide-to-the-markets/