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  • Jason R. Waller

How to Make Impossible Decisions

The five tactics that have helped me most.





One month ago, I was wrestling with what felt like an impossible decision. I was trying to decide whether to fly back to the US, to spend time with my oldest children, or stay in Australia, with my youngest child. The complicating factor is that, for all of 2021, Australia has kept its borders closed. I likely could have gotten permission from the government to leave, but it’s not clear that I could have gotten permission to come back.

Now, I’ve made difficult decisions before. I’ve made some pretty life-or-death calls during my time in the military, and there are a hundred other decisions that seem more dire on paper. But for me — nearly a year after last seeing my oldest daughter and son — this was the most emotionally difficult decision of my life. I really didn’t know what the best choice was.

For clarity, I turned to five tried-and-true tactics that have served me well in the past. Now, I’d like to share them with you. Maybe they’ll help you like they helped me.

1. Years, not days

This nugget is number one for a reason. Think in the long term. Try this: when you’re confronted by a really difficult decision, think about things in terms of years, not days. We can often get caught up ruminating about the immediate consequences. How we’ll feel, what will happen, what will happen next, etc. But to really focus on what matters, think about what changes a year or even a decade later.

For me, this brought clearly into focus that the bulk of my anxiety was focused on short-term problems. There was one clear long-term concern, however, and that was my relationship with my kids. I could miss a chance to build a deeper relationship with them, a chance that might not be there in the same way when they’re older.

2. Want vs. avoid

What we “want” is sometimes just a shadow of something that we’re trying to avoid. This sounds innocuous, but when we account for our human nature (negativity bias, loss aversion), the risk is that we can sometimes make much poorer decisions if we’re avoiding something than if we’re pursuing something. When you have to make a call, think not only about what you want, but also what you’re afraid of. Take stock of which one’s really at the wheel.

For me, I was definitely trying to avoid any loss of relationship or connection with my children. It was a lot less about building and developing as it was about preserving and maintaining. And this isn’t wrong, by the way. There’s nothing misguided about wanting to preserve a relationship. But the weight and significance was much louder, simply because it was something I was terrified of. And I had to spend some time reconciling that.

3. Lean on your values

I talk to my clients sometimes in terms of “big ‘W’ wants” (values) and “little ‘w’ wants” (emotions). Example: I may Want to be healthy and take care of my body, but today I want a cheeseburger and to stay on the couch. Your emotions always have some information in them, but they’re not always to be trusted. A great investment is to practice becoming more attuned to your values and less dependent on your emotions. In a difficult decision, it can be helpful to remind yourself of your core values, what really matters. It can also be helpful to be a bit skeptical of how you feel.

For me, the drive to go back to the US was led by my emotions, but there was also a big showing from my values of family, community, and responsibility. I reflected on what truly mattered to me and really embraced that there was a “big ‘W’ want” at play here.

4. Flip a coin

I want to make the disclaimer early that I’m not actually advocating for leaving a big decision to chance. But, I am making the observation that I often realize what I really want when that choice is taken away from me. The next time you have a truly difficult choice to make, try this: have a friend (better if you get a third party) flip a coin or make a decision for you. Chances are (pun intended) that you’ll get a greater sense of what you really want in the process.

For me, I didn’t have a friend to help me flip a coin, so I just imagined. I said, “yep, we’re going to stay here in Australia, that’s it.” And in that moment I felt a real sorrow for what I was giving up. I also got to feel the excitement for the opportunity to see my kids. I was given a chance to live in the certainty of a choice and get clearer on what the outcome actually meant to me.

5. Explore counterfactuals

Finally, if you’re really stuck, try playing the opposite game. For instance, if you’re struggling to decide between two impossible choices, pretend that both are possible. If you’re feeling forced to make a choice, pretend that you have complete independence. In my experience, this unlocks a different part of our creativity. We can be so consumed with fighting against the constraints (real or imagined) that we lose energy for the actual problem at hand.

For me, I felt like seeing my kids or not was a life-or-death situation. I tried to imagine it instead as an opportunity, as something that was a rich possibility. I also felt like the assumption was that I would stay in Australia. I tried to imagine the situation as if it was assumed I would be leaving. Both of these helped me to re-frame how I thought about my decision.

Bonus: move faster on decisions that matter

It can sometimes also help to reframe your decisions as reversible and irreversible. Jeff Bezos called these two-way doors and one-way doors. This matters because we can sometimes exert an unnecessary amount of energy on decisions that we can reverse someday in the future (or, to a lesser extent, not enough energy on the decisions we can’t). Ask yourself: is this decision temporary or permanent? If the former, allow yourself to move faster, make a call, and start experimenting!


In the end, I decided to stay in Australia. Actually, I decided to stay with the caveat that I would buy plane tickets to return home in December. I bought the tickets and still feel a bit squeamish about whether I can leave and come back with no repercussions. But I know I made the right choice. I’m willing to live with the risk of this one. I’m willing to accept that there’s a small chance things could go very bad. But, if I decided to leave, there’s a big chance that things will go a little bad.

The math worked out this a little easier than expected, but I also leveraged all of the five perspectives above:

  • Years, not days, think long-term

  • Want vs. avoid, think about what you’re afraid of

  • Lean on your values, focus on “big ‘W’ wants”

  • Flip a coin, you’ll often know the answer in the air

  • Explore counterfactuals, play the opposite game

These might not make your decision any easier, but my hope is that they can help make it clearer.

Good luck on your journey.

Originally published in MindCafe