Making hard decisions

We’ve all been there — facing a decision point that feels life-altering, agonizing over the pros and cons, paralyzing yourself in order to avoid making the wrong choice.

While there’s hardly a silver bullet for making “hard decisions”, I’ve found it useful to leverage prompts to force me to evaluate the situation from different angles. This is a short post with some that I’ve found helpful over the years; please share what has worked for you!

What are the consequences of each of my options – 10 minutes from now, 10 months from now, and 10 years from now?

– Annie Duke, professional poker player and author of Thinking in Bets

If I were to imagine myself as an 80-year-old looking back on my life, which of these options will I most regret not choosing?

— Jeff Bezos, former bookseller turned global tycoon

Humans overestimate how much they can get done in 1 year, but underestimate how much they can get done in 10 years. Which category am I dealing with now?

— Jim Collins, author of Good to Great and one of my favorite podcast guests

What is the one decision I can make in this situation that would remove 100 other decisions that are swirling in my head right now?

-- Greg McKeown – author of Essentialism

If I make this decision, what are the ways in which I could undo it? Is this a one-way door or a two-way door?

— Jeff Bezos, who boringly introduced this concept as "Type 1 vs. Type 2 decisions"

Am I thinking of doing this because it's what I want to do or because it’s expected of me?

— Lots of people

What is the story I'm telling myself? Could the opposite of my story be true? What actions am I taking that are contributing to the situation I’m in?

— Byron Katie, The Work

If I allow myself to imagine the worst case scenario here, how bad will it actually be?

— The Stoics via negative visualization

If you make this decision, what will my day-to-day look like? What about that sounds energizing? What about it sounds draining?

— Not sure

What are the “best”, “average”, and “worst” case scenarios for each option? For each one, imagine having started down that path only to realize that it's trending too much towards the worse case, (a) how long am I willing to give it a shot, (b) what would it look like to reverse that choice, and (c) what would have been irrevocably missed during the time by not choosing one of the other options?

— My nerdy framework built around some of the others above

Heads I choose X; Tails I choose Y. Flip a coin. How do I feel about the winner?

— The simplest of the bunch

And as someone who went to school for engineering and is married to a therapist, I particularly enjoyed the book “Emotional Equations” by Chip Conley, which breaks down feelings into simple equations that can help you introspect what may be going on as you grapple with hard decisions.

”Hard decisions” are hard because being a human being with a paleolithic brain in a modern world full of a bazillion inputs is tough. I hope this post helps just a little as you grapple with your challenges. Good luck!