How to not know

My friend Simone Stolzoff has a new book out, titled How to Not Know. As you can imagine, I found this book fascinating, and I even learned some stuff about sitting with uncertainty—something I absolutely, obviously, hate to do (I feel myself breaking out in hives just thinking about it). I asked Simo to answer a few questions for us, below. Enjoy!

Nell: When it comes to making decisions at a time in our lives/history when things feel extremely unpredictable, how do you suggest we start?

Simo: There are two things happening at this moment. The first is that the world is becoming more uncertain. Between the pandemic, shifting tariff policies, and wars overseas, it's no secret that uncertainty surrounds us. The second is that our tolerance for uncertainty is in decline. Many experts attribute this to the rise of the internet, and more specifically, mobile phones, which have created the expectation that answers should be readily available.

When it comes to making decisions under uncertainty, I offer a few suggestions in the book. The first is to separate what you can and cannot control. A lot of the stress in modern-day life stems from worrying about things outside our realm of influence. The second is to find your anchors — that is, the things in your life that will remain constant amidst all that is changing. When we are certain about some facets of our lives, it becomes easier to hold uncertainty about others. Becoming aware of your anchors and what you can actually change is a great starting point for making any decision.

Nell: Hard agree on both of those tips! Do you have any practical, do-it-now suggestions for making decisions when we feel totally unsure?

Simo: There's an ethicist I spoke with for the book named Ira Bedzow, who works at a university and specifically with college students trying to figure out their futures. Whenever he meets with a student, he always asks the same three questions.

The first is: What do you want? I love this question because it's an attempt to get out of our heads and into our more embodied knowledge. The second is: Do you want to want this? This taps into what philosophers often call our second-order desires — a more reflective way of thinking about a problem. Do I want a cigarette? Sure. Do I want to want a cigarette? Maybe not.

The third question is the most important: What does that choice say about who you are? The question connects our decisions to our values and our identity. At the moment of making a decision, you can't know exactly how it's going to turn out. But if you make a choice from a place that is aligned with who you are and what you care about, you can stand by that decision — even if you don't get the outcome you desired.

Nell: I always encourage people to write out their list of values as a shortcut for making decisions…although everybody, me included, certainly sometimes makes choices that are not in line with those values 🤪. I’m thinking of when I procrastinate on going to the doctor even though I think of myself as someone who takes care of her health.

I REALLY loved this line in your book: "Rather than having to make the right choice, we can make any choice right." Can you say more about this?

Simo: I also love this idea. There's a philosopher I quote in the book named Ruth Chang, and one of her main arguments is that what makes a hard decision hard is not that there's a clear right answer and we're too stupid to figure it out. What makes a hard decision hard is that one option is better for some reasons, the other for others, and neither is better overall. If that weren't the case, it would be an easy decision.

And so in these moments — when there are trade-offs rather than a clearly better or worse path — we have to be willing to trust in our future selves' ability to make the decision right. Often, when we're standing at a career crossroads or deciding whether or not to leave a relationship, we can't know exactly what benefits any given choice will bring. Part of what makes the choice so hard is that committing to one option feels like foreclosing on all the others. That's why making decisions can sometimes feel more like a loss — because choosing one path means choosing not to take all the paths you might have taken.

And yet, Chang's wisdom is that after we make a choice, we can convince ourselves we made the right one. That is to say, we can spin a narrative about the reasons behind our choice — and in my mind, that is exactly what it means to make a choice right.

Nell: I have a similar belief, which is that you can make almost any decision the right one simply by working hard enough at it. In your book, you give the example of Meg, whose work demonstrated the usefulness of writing down your decisions so you can compare the results with your initial hypothesis and see if you guessed right or not. This had never occurred to me! Do you do this in your own life/can you give us an example?

Simo: It makes perfect sense, doesn't it? If we want to get better at making decisions, we have to be able to measure the quality of the decisions we've made. But we can’t do that unless we can compare our assumptions to reality. That said, it's easier said than done. Right now, there is very little accountability for people's predictions. Turn on the TV, and you'll see cable news pundits telling you exactly when the market is going to crash or who’s going to win the game, with zero accountability for whether or not their predictions are accurate.

In my own life, I most often practice this idea of writing things down in a work context. I'll try to write down a hypothesis I'm testing — for example, I used to lead research for the design firm IDEO, and at the top of our research briefs, we would always write down the hypothesis we hoped to test. But this can also be a useful exercise in our personal lives. Writing down my predictions, decisions, and desires has been a great way to remember that present me has a lot of what past me once wanted.

Nell: Any final words of wisdom about getting more comfortable with NOT knowing?

Simo: The book's thesis is that uncertainty is not necessarily a problem to be solved. After reporting and writing about it for the last few years, the one idea that has stuck with me the most comes from psychologist Rollo May, who said that “commitment is healthiest not in the absence of doubt but in spite of it.”

I love this idea. As human beings, we have to be able to make choices even when we're not sure. That, I imagine, is one of the most vital skills for surviving the current moment we are all living through.

Thanks, Simo! You can buy How to Not Know here, or check out his Substack.