Improve your decision-making abilities
Reframe how you approach decisions and leverage new strategies to make decisions with more confidence, clarity and resolve.
Failing to make necessary decisions is often what keeps our lives stagnant, small and safe at the expense of our happiness and realizing our potential. When we overcome fear and self-doubt and decide to pursue what we deeply want, we may truly thrive. The reality is, there’s very few decisions that we can’t bounce back from even if they go awry.
After reading this, my hope is that you begin making decisions with more confidence, clarity and resolve!
To that end, this newsletter includes:
suggestions for a more empowering mindset toward decision-making
exercises to clarify and define your decision
prompts to challenge your biases and uncover blind spots
tools to engender decisions you will be proud of, regardless of the outcome
tips to sit more confidently and peacefully with your decision
Many of the exercises, techniques and prompts included here are cherry-picked from a few of my favorite books and related decision-making frameworks that you will find at the end of this newsletter. Spoiler alert: The Tim Ferriss "Fear-setting" exercise is an absolute game changer!
Note: Although the intention for this guide is to enable you to make better individual decisions, much of the content included here is valuable when making decisions for your team and organization as well.
1. Embrace an empowering mindset towards decision-making
Approach decisions with an “I’m not sure” mindset instead of “I hope I make the right decision.” Hoping to get it “right” produces excessive attachment to one specific outcome. In reality, once you’ve made a decision, various people and circumstances out of your control will influence how your decision actually plays out.
The “I’m not sure” perspective surrenders to how much is out of your control and opens you up to thinking about a spectrum of possible outcomes resulting from your decision. This cultivates a broader, more flexible outlook, acknowledging that a variety of outcomes would still be good or at the very least, tolerable.
Instead of viewing decisions as permanent and final, embrace them as dynamic, fluid experiments. Holding an experimental perspective encourages you to remain vigilant instead of going into autopilot after you’ve made a decision, allowing you to tweak or course correct early if you see that your decision is inching toward a less desirable outcome.
2. Clarify and define the decision to be made
If you are faced with a 'whether or not' decision, be suspicious. Challenge it. Decisions framed up in this manner reflect a false dichotomy and rarely take the larger context into consideration. For example, instead of wondering whether you should buy a minivan for your family or not, zoom out and ask, “What is the best way I could spend some money to make me and my family better off?”
To force you to think of other alternatives, determine what you would do if neither of the ‘whether or not’ options were possible. This allows your mind to shift focus to entirely new ideas and strategies.
Another way to dismantle 'whether or not' decisions is to consider the opportunity cost. For example, if you buy the minivan, what are you unable to spend money on as a result? Just thinking about opportunity cost reveals the many ways you may want to alternatively invest your precious time, money and mental calories.
Widening the aperture with which you view your decision ensures you are not making a decision out of context and expands the possible options to consider. The original 'whether or not' decision regarding the minivan evolves into something more expansive like “Should I buy a minivan, take my family on vacation and/or remodel our kitchen to make my family better off?”
3. Reduce biases and uncover your blind spots
When approaching a decision, you will naturally seek out and pay attention only to information that confirms what you already believe is your best path forward and discredit evidence to the contrary.
To avoid falling into the trap of confirmation bias, seek out the reasons why your favorite path might not be the best one by questioning what’s wrong with this path? Why won’t it work? Then look at the other available options and identify what would have to be true for each of those options to be the best choice for you. This challenges you to imagine conditions in which you would choose a different path than what you are currently considering.
Using prospective hindsight, or the act of generating an explanation or narrative for a future event as if it had already happened, allows you to illuminate your blind spots. According to Gary Klein’s research, prospective hindsight increases the ability to correctly identify reasons for future negative outcomes by 30 percent.
To elaborate, say you’re contemplating starting a family. Using prospective hindsight, imagine it is three years from now, you have a toddler and you are struggling. Ask yourself, “How did I get here?” Your response may include statements such as, “I neglected to show up for my spouse and our relationship. I tried to engage at work with the same level of intensity as I did before I had a kid and burned out quickly. I forgot to take care of myself. I never saw my friends or family members.”
By working backwards from your worst case scenario, you are far more aware of what roadblocks or challenges may lie ahead and you can plan today for how to reduce the likelihood of those challenges steering you off course in the future. For example, to avoid the pitfall of neglecting your marriage once you have a child, before the baby arrives, commit to a recurring weekly date night that will kick off once your baby is 2 months old.
"Invert, always invert: Turn a situation or problem upside down. Look at it backward. What happens if all our plans go wrong? Where don’t we want to go, and how do you get there? Instead of looking for success, make a list of how to fail instead–through sloth, envy, resentment, self-pity, entitlement, all the mental habits of self-defeat. Avoid these qualities and you will succeed. Tell me where I’m going to die so I don’t go there."
- Charlie Munger
Establish a tripwire or some early triggers that will remind you to revisit your initial decision and determine if you should stay the course, make some minor tweaks, or pursue an alternative path altogether.
Good tripwires include a metric and a deadline. Say you’ve decided to join a start-up, inspired by its mission and product vision. However, you are skeptical about its ability to get a product to market in a reasonable timeframe and consequently, its economic viability. You may want to set a tripwire that, if in 6 months the product hasn’t been released, you revisit your decision to join the start-up and take corrective action if necessary.
4. Make decisions that you will be proud of regardless of the outcome
Making a decision that will make you proud independently of the outcome requires one critical ingredient - it must reflect at least one of your core values. Going back to our earlier example, let's say you've decided that remodeling your kitchen is the best way to make your family better off. A more functional, inviting kitchen will reflect your values of eating nutritious foods, connecting with your family during meal time, and entertaining close friends. Not only will you feel proud of your decision, but it will increase your resolve and resilience even when that kitchen remodel is 10 weeks too long and tens of thousands of dollars over budget.
For many, the calendar is the ultimate scoreboard for standing behind and living your priorities. A helpful lens with which to view your upcoming decision is to evaluate whether the hours blocked off on your calendar will accurately reflect the type of person you want to be and your most precious priorities.
Suzy Welch’s 10-10-10 exercise will also increase the probability that your future self will be proud of your decision. At decision time, pause for a moment and ask yourself how you will feel about it in 10 minutes, 10 months and 10 years.
This one is particularly helpful as you contemplate skipping your workout again, losing your patience with your threenager or slinging some not-so-kind words at your partner.
Imagining being accountable for your decision in the distant future reduces the emotional charge in the moment and allows you to evaluate the decision in the broader context of your life.
5. Find peace and confidence once your decision has been made
Once a decision has been made, do what you can to generate your best possible outcome.
Regularly check in on the progress of your decision. Remain vigilant for your tripwire or early signs that your decision may be playing out in a less favorable way and take corrective action when necessary. Remember, you are not stuck with any decision!
When reflecting on decisions further back in your rear view mirror, do not fall into hindsight bias where you give yourself a high five simply because you got a good outcome. For those of you who have driven home slightly buzzed and arrived there without incident, does that mean you are excellent at making decisions or just super lucky? Conversely, it’s easy to lament your decision to accept a new job at a travel company in April of 2020 when the company failed months later. Does that mean that you should punish yourself and live with regret because you couldn’t predict a global pandemic and that the travel industry would screech to a halt?
So that you may grow from previous decisions and then move the hell on, think about what information you had at the time you made your decision. Going back to the travel company example, outside of predicting the pandemic, is there any information you should’ve sought out, such as the quality of the leadership team or its cash runway? Is there anything you didn’t consider that should be considered moving forward.
Once you’ve learned what needed to be learned from your past decision LET. IT. GO. The longer you regret a decision and spin your wheels on what could’ve been, the longer you don’t tend to what you can do in this very moment and in the future to bounce back from it.
6. For your decision-making pleasure, I have shared some of my favorite frameworks below:
From "How to Decide," Annie Duke’s How to make good decisions in 6 steps” is excellent if you’re a probability nerd like me and you are weighing several possible outcomes.
Tim Ferriss’ “Fear Setting” Exercise is a game changer if fear is what is holding you back from deciding to do something you truly want. For all of you toying with the idea of starting your own business or doing something else equally courageous, this might be especially poignant for you.
From Dan and Chip Heath’s "Decisive", the WRAP framework helps you widen your frame about the decision to be made and test assumptions. This is quite effective for decision-making in a team/organizational context as well.
Personal Reflection Prompt:
What is an important decision I’ve been avoiding that I will confront using some of these new strategies?
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