How to make big decisions
Why the hardest decisions are the ones where every path leads to a great outcome
In any situation, the best thing you can do is the right thing; the next best thing is the wrong thing; and the worst thing you can do is nothing.
Theodore Roosevelt
Most decisions aren’t that hard. We choose the best option and move on.
But big decisions, like where to live and which job to take, are paralyzing in a way that daily decisions aren’t. These decisions touch every area of our lives, and once we make them, they’re extremely difficult to reverse.
Big decisions become even harder when we have all the options lead to great outcomes.
When one path is clearly better, the choice is still consequential, but it’s easier when we know what the “right” path is. When all of our options are promising, the choice is not only consequential, but we agonize over which path is the “right” path. There’s always something to wonder about, always a reason to second-guess whichever we choose.
Making big decisions is about making the “right” choice, but how we think about that choice afterwards is just as important.
Go Deep
The most costly error when making a life-altering decision is not going deep enough.
If we don’t carefully consider our options and what’s important to us, we risk going down the wrong path and living with the regret of making a big decision carelessly.
Deeply considering our options comes down to two things: defining the life we want to live and evaluating how each path will move us closer to or farther from our ideal lifestyle.
These questions are nearly impossible to answer in our heads.
Different options will impact different areas of our lives and create countless dependencies and scenarios that we can’t process and compare at once. To go deep and properly consider the consequences of each option, we have to get our thoughts on paper.
Writing down our thoughts (aka journaling) allows us to capture the complicated and incomplete ideas in our heads and transform them into concrete and meaningful words on the page. Writing forces clarity.
Once the pen starts moving, ambivalent feelings and inexplicable anxiety become clear and organized statements that we can review, compare, and understand.
Journaling lets us consider our options at a deeper level and gives us the information and understanding we need to choose the “right”path.
Commit and Accept
But, our job isn’t over when we decide. It’s just beginning.
The decision may work out, or it may not. It may unfold as expected, or look entirely different. Regardless of the outcome, we have to commit fully and accept what we chose.
This is especially hard when all our options were promising. Even small disappointments feel like evidence we that picked wrong path. When every option seemed like a great choice it’s easy to imagine parallel lives where the grass was greener on the other side.
As soon as we make the decision, we have to close the door on alternatives. Not because we definitely chose right, but because second-guessing is its own kind of losing. If we spend our energy on “what if,” we never fully commit to the life we chose, even if it was the right one.
Every big decision is made with incomplete information. We owe it to ourselves to go as deep as we can before choosing, but equally as important is accepting our decision with grace, committing to our new direction, and embracing whatever comes next.
Prompts
Think of a big decision you’re facing or have faced recently. Did you go as deep as you could before deciding? If not, what held you back?
Is there a past decision you’re still second-guessing? What would it feel like to fully close the door on the alternative?
When you’ve made a decision and things didn’t go perfectly, how did you respond? What does it look like for you to accept a choice with grace?
Deep Dive
Thinking in Bets by Annie Duke
A guide to making decisions under uncertainty from a professional poker player.
Thanks for reading! I’ll see you next Sunday.
Kevin