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Making good decisions in wicked environments

We recently decided to move.  The short story is that we found and bought the perfect house at a reasonable price and we sold our current house in just four days for over our asking price.  Sounds good, right?  Upon hearing the news, someone close to me commented, “Wow, you guys really got lucky!”.

Did we?  As always, there was some chance involved, but we also made a thousand decisions along the way in an attempt to optimize our chances of a good outcome.

    • We researched the housing market for months, waiting for the right house within our budget
    • When we found the house, we acted quickly by registering an offer early to intimidate other buyers who didn’t want a bidding war
    • Knowing the house was slightly under-priced, we made a generous offer and wrote a letter to go with it because we know that for many sellers it’s not just about the money.  Our offer was accepted
    • We worked our asses off for several weeks to make our current house looked as appealing as possible
    • We got our own inspection showing the house is sound and made the report available to potential buyers so they’d be more confident making an unconditional offer
    • We staged the outside of the house
    • We staged the inside of the house
    • We priced the house aggressively to generate interest
    • We held off on offers for four days hoping for more than one offer
    • When two competing offers came in we didn’t just accept one, rather we gave them each a chance to improve their offers.  They both did.

In hindsight, each of these actions appears to have contributed to our positive end result, but I’m not really taking credit here.  Let me tell you, each one was rife with uncertainty.  We passed over so many opportunities to buy other “good” houses that we thought we’d never find a “great” one.  When we put in our offer, we didn’t know if it would be too high or too low.  We didn’t know if working on our current house for several weeks would delay the listing into the bear market that seems to be coming.   We didn’t know if holding off on offers would turn buyers off.   

We didn’t know what the outcomes would be at all.

What we did know was that, given the situation, there were certain actions that seemed to give us the greatest chance of the outcome that we wanted.  We knew things might go awry, but we worked our butts off nevertheless.  If we didn’t get the outcome that we wanted, at the very least we’d know we did everything we could.

A mantra for hard times

I had a coach once who taught me a great lesson.  He said that most of the time we are seeking ideal outcomes while performing under less-than-ideal circumstances.  So, in your quest for greatness, you can either spend your time thinking about all the things you wish were different or ask yourself a simple question: What is the best thing I can do right now given the circumstances?  It’s the kind of advice that can be applied across the spectrum of life.

Most of the time, we don’t control outcomes; we control our actions.

The same is true in investing.

The hardest part about being an investor is uncertainty.  You don’t know if your decisions are the right ones until the outcomes are known.

To make matters worse, sometimes good decisions are followed by bad outcomes and bad decisions are followed by great outcomes.  Actions and outcomes are not perfectly correlated.  The relationship is probabilistic and can only be understood with many data points over long periods of time.

Kind vs. wicked learning environments

Behavioural scientists distinguish between kind and wicked learning environments.  A kind learning environment is one in which the results of our decisions are immediate, accurate, and abundant.  Think chess: as difficult as it is to master, the rules are clear and unchanging, and the players receive immediate rapid feedback from their decisions.

Wicked learning environments, on the other hand, are ones in which our experiences are subject to filters, delays, and distortions.  Real estate is a good example.  Houses are unique, sellers have their quirks, buyers have their own agendas; the markets shift and lurch with interest rates, seasons, trends, and economic policy.  You make decisions and wait months for the results.  There is no “right way” to buy or sell and home and the optimal answer is often only clear in hindsight, if ever.

You might recognize medicine as another particularly wicked learning environment.

“The world does not play fair.”

In How We Know What Isn’t So, psychologist Thomas Gilovich writes, “The world does not play fair. Instead of providing us with clear information that would enable us to ‘know’ better, it presents us with messy data that are random, incomplete, unrepresentative, ambiguous, inconsistent, unpalatable, or secondhand.”

The stock market is another wicked learning environment full of data that is “random, incomplete, unrepresentative, ambiguous, inconsistent, unpalatable, or secondhand.”  Look at the wealth that you have achieved.  It did not grow easily or steadily, rather in fits and starts and contractions.  Building wealth is a journey through a wicked learning environment and it’s not a comfortable one.

“In investing, what is comfortable is rarely profitable”

Robert Arnott

Rather than spending, you exercised self-discipline and saved.  Rather than giving in to the safety of cash or bonds, you invested in the stock market.  Rather than following the trends of cannabis, tech stocks and cryptocurrency, you maintained the slow and steady course with blue-chip dividend-paying stocks (and maybe a few ETFs).

Wicked environments demand better decision making

Your wealth, whatever it is, is not the result of luck.  It is the result of enduring the discomfort of uncertainty and making good decisions anyway.

Every decision carries risk.  If there were no uncertainty, there would be no need to make a decision – your course of action would be obvious.  In this time of market turmoil, the right decision is often to sit and do nothing as your portfolio balance decreases.  Such is the nature of wicked learning environments.

“There are no solutions, only trade-offs.”

Thomas Sowell

How to make better decisions

Dr. Robin Hogarth who co-wrote the book “The Myth of Experience: Why We Learn the Wrong Lessons, and Ways to Correct Them” has advice on how to make better decisions.  The first step is to determine how wicked the learning environment that you’re in is.  Then ask yourself two questions.  First, what is missing from the data that I am using to make decisions?  And second, what irrelevant details are in front of me that I should ignore?

As the markets gyrate, you have decisions to make.  Do you sell to avoid further losses, change your holdings, or stay the course . . . ?  But before any decisions are made, recognize the limitations of the wicked environment you’re in: what you don’t know, and – just as importantly – what you know that is best ignored.


If you are interested in learning more about personal finance, investing, and how to make sense of how money works in your life, consider signing up for a moneySmartMD course.  These are live virtual courses that you can enjoy from the comfort of your own home or office.  The June course is full, but there is space remaining for the fall dates and early-bird pricing is still available.

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