3 Ways to Stack the Odds in Your Favour

The art of doing fewer dumb things.

Learning From Mistakes

If you think back to your worst business decisions, did you ignore the early warning signs of trouble? I’m talking about the unforced errors – the decisions that made sense at the time, but ultimately cost you in stress, time, relationships, or money.

In most cases, with hindsight, you can identify those early hints that something was about to go off course. Like hiring someone you weren’t excited to have on the team, or working with a customer who turned out to be way more trouble than they were worth.

Making that decision, choosing your path, is like gambling. You’re placing a bet that the investment of your time, money, energy, and resources will pay off. Unlike a trip to the casino, however, in business you get to stack the odds in your favour. Here are three tips to increase your odds of making a winning decision.

Stacking the Odds in Your Favor

  1. Before going with your gut instinct, give yourself time to think.

    Step away from the desk and take a shower or go for a walk. Even better, grab a notebook and capture your assumptions, expectations, and unanswered questions on paper. Talk through the pros and cons with a trusted mentor or coach. It sounds straightforward to carve out the time to think over your decisions before acting – but if you think back to your most costly mistakes, did you take the time to think them through?

  2. Consider the alternatives.

    It can be hard to judge whether an idea is good or bad when it’s the only one in front of you. What other paths could you take, what other bets could you place? What would you do if the most obvious course wasn’t an option? By choosing this, what are you saying no to in the future?

  3. Ask the big-picture questions.

    Is this decision congruent with your values as a person? With your company’s values? Will it get you closer to achieving your vision? These big picture questions are great for putting today’s decision in perspective. If there’s an option that has short-term benefits but is ultimately incongruent with your values, what are the odds you’ll come to regret placing that bet?


This Week’s Takeaway

There’s a lot to be learned from your worst business decisions. Looking back – what caused them? Were you operating out of emotion or logic? Did you wait too long, or decide too quickly? What warning signs did you ignore?

We can often grow more from our mistakes than our successes – if we’re willing to learn.


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The Psychology of Money: by Morgan Housel

When it comes to money, it’s not just about what you know—it’s also how you act. Even the brightest folks can struggle with finances because, unlike with math, behavior isn’t as easy to change. “The Psychology of Money,” delves into the complex relationship with money, giving invaluable insights to help navigate this crucial aspect of life with greater clarity and confidence. Check it out!


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