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Thinking It Through

Adam M. Grossman  |  May 10, 2020

ON JAN. 10, 2000, America Online co-founder Steve Case stood on stage in New York to announce the largest corporate takeover in American history, buying venerable Time Warner for $165 billion. At the time, commentators called it the merger of the century. But just five years later, Case acknowledged that it was actually “the worst merger in history” and argued that it was time “to take it apart.”

Making financial decisions is difficult even in good times. But when we have a year like 2020, it’s that much harder. And yet it’s precisely at times like this that our financial choices may have the most impact. Here are just some of the questions I’ve been hearing in recent weeks:

  • Should I take advantage of the CARES Act provision that suspends student loan payments or should I continue paying since every dollar will now go toward principal?
  • Should I take advantage of today’s low interest rates to refinance to a 15-year mortgage—which will lower my rate but increase my payment—or should I prioritize holding onto cash?
  • Should I borrow to invest in my business, or should I just hunker down and try to make it through?
  • Should I buy more stocks while the market is down—or should I wait to see if it goes even lower?

What’s the best way to tackle questions like these? For some, the answer is to “run the numbers.” For others, the solution is to “trust your gut.” But both suggestions seem more like vague platitudes than true action plans. Fortunately, research has identified a number of tools and techniques to help us make better choices in the face of uncertainty. Here are 10 ideas that I find most useful:

  1. As a former professional poker champion, Annie Duke knows a thing or two about making high-stakes decisions under pressure. In her book, Thinking in Bets, Duke recommends “mental time travel.” The idea is to put yourself in the shoes of your future self and to try to envision the impact of the decision you’re considering. Imagine what the impact would be if it went well—and imagine if it went poorly. Then evaluate the effect on your financial well-being. While this sounds like commonsense, it’s important because everyone is different: Some of us are natural optimists, while others are pessimists. To counter both tendencies, we should force ourselves to consider the full range of outcomes.
  2. Understand what kind of decision you’re dealing with. Specifically, you want to understand the payoff structure. With stocks, the downside risk is 100%, but the upside is unlimited. With bonds, both the upside and the downside are far more limited (most of the time). Meanwhile, stock options and startup investments are closer to lottery tickets: a very high likelihood of loss offset by a gigantic payoff if things work out. Investments in your home—in the form of renovations—or investments in a business partnership carry their own risk-reward structures.
  3. Even when a decision doesn’t seem quantifiable, try to quantify it anyway. That’s the advice of J. Edward Russo and Paul Schoemaker in their book Winning DecisionsFor example, if you’re choosing between two houses, develop a simple scoring system, assigning points for location, price, school district and so on. Similarly, you could use this technique to choose among colleges, job offers or vacation destinations.
  4. Duke recommends conducting a “pre-mortem” analysis. The idea here is to imagine that you’ve made a decision, it’s a year later and things have gone poorly. Now ask yourself why things went wrong. In other words, think rigorously about all the ways something could go wrong, no matter how unlikely. If you’ve ever bought a house and done a home inspection, that’s exactly the idea. Do a head-to-toe examination. Look under every rock for potential problems. Then ask yourself if there are ways to mitigate those risks in advance.
  5. To the extent that a decision is emotional, Duke advocates journalist Suzy Welch’s 10-10-10 rule. This simple technique forces you to evaluate a decision by asking how you would feel about it in 10 minutes, 10 months and 10 years. This may help put things in perspective and can be especially helpful with investment decisions, where the time horizon is usually multiple decades.
  6. A variation on the 10-10-10 idea is to conduct this thought experiment: Imagine the worst-case outcome for a decision. Now imagine that it had occurred a year ago and ask yourself whether you would still be feeling the impact. This is another way to put things in perspective.
  7. Try taking your own temperature. If you feel yourself getting stressed as you consider a decision—Duke uses the term “on tilt”—take time to get on an even keel. Go for a walk or sleep on it. In fact, Benjamin Franklin, who invented the pro-con framework for decision-making, recommended taking several days to make any big decision.
  8. If something is particularly difficult, enlist help. Bring in an accountant, a lawyer or some other trusted advisor to help shoulder the load. If something is too hard from an emotional perspective, you might even delegate it entirely. If you’re dealing with a business dispute or the IRS, or with something equally distasteful, hire someone to help with the negotiations. Not only will you sleep better, but also you might get a better outcome.
  9. One underestimated way to get better results when making decisions: Get the timing right. While this may sound hokey, there’s a lot of research to show that you get better results when you align certain types of work with certain times of day—and this varies from person to person. This is known as our chronotype. If you understand yourself better in this way, you can use it to great advantage as you make decisions. In his book When, Daniel Pink describes this in detail.
  10. Finally, Duke cautions against putting too much weight on our own experiences. Yes, it’s important to learn from our own successes and failures. But Duke rightly points out that we’re all working with a “sample size of one.” Because of luck, sometimes good decisions have a bad outcome, and vice versa. As she notes, “Decisions are bets on the future, and they aren’t ‘right’ or ‘wrong’ based on whether they turn out well on any particular iteration.” This advice is particularly applicable to financial decisions, where we’re often bedeviled by the twin biases of overconfidence and lack-of-confidence.

Adam M. Grossman’s previous articles include Regrettable BehaviorDefending Yourself and As If. Adam is the founder of Mayport Wealth Management, a fixed-fee financial planning firm in Boston. He’s an advocate of evidence-based investing and is on a mission to lower the cost of investment advice for consumers. Follow Adam on Twitter @AdamMGrossman.

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