5 Strategies for Dealing With Uncertainty

(from Simone Stolzoff, who literally wrote the book on it)

I met Simone Stolzoff earlier this year through a Bay Area group for non-fiction authors. When I learned his new book How to Not Know was about the art of not knowing — making peace with ambiguity, building tolerance for the unknown — I begged for an advanced copy and tore through it in a single day.

I’ve built my life and career around controlling the controllable: homes, schedules, business ventures. But sitting with uncertainty, navigating loss, working through transitions? Still very much a work in progress (help me, Simone!).

His book (out today) is full of real-life examples and practical tools for anyone trying to get more comfortable with not knowing, and I’m so glad I can share our conversation with you here.

Q/A with Simone Stolzoff

Are you naturally good at sitting with uncertainty?

No! I’m a naturally indecisive ruminator. When I don’t know something, I love to poll everyone I’ve ever met (and my yoga teacher and my Uber driver). But one inspiration for writing the book was a study I read that uncertainty tolerance is a skill that you can develop. I’m biased, but I think the ability to sit with what we don’t know is one of the most important capacities we can develop—in our careers, in the world, and in our lives.

What’s a belief you held with total certainty that turned out to be wrong?

That leaving journalism would be the end of my writing career. When I was 28, I decided to leave my cushy magazine-writing job to join a design firm called IDEO. I thought I was hammering the nail in the coffin of my writing career when, in fact, leaving newsrooms was actually what allowed me to write my first book.

What’s one thing you’re genuinely uncertain about right now?

The world that my son will inherit! I’m a new dad and find myself waffling between excitement and fear about the world that my son Luca will grow up in. As the cliché goes, you write the book you need to read!

Your top tips for navigating anxiety about the future?

Find your anchors. When we are certain about some aspects of our lives, it makes it easier to hold uncertainty in others. For example, getting clear on your values or a commitment to live in a certain place, might make it easier to hold uncertainty in your career or relationships.

Ask yourself: What are aspects of my life that are likely to remain steady even if the future looks very different from today?

Separate what you can/can’t control. In the words of the Serenity Prayer, “Grant me the serenity to accept the things I cannot change, the courage to change the things I can, and the wisdom to know the difference.” For example, by shifting your attention from the existential threat of AI to what you can do to build your own AI fluency, your agency can absorb some of your anxiety.

Ask yourself: What am I wasting energy worrying about that I have no power to control?

Build your conviction with evidence. One of the best ways to become more comfortable with uncertainty is to remind yourself of times you’ve navigated uncertainty in the past. For example, perhaps there was a time when you thought “your life was ending,” that actually turned out to be the beginning of a new chapter.

Ask yourself: What is a time when I was able to navigate uncertainty in the past?

Plan for multiple possible outcomes. Anchoring your identity to a single vision of the future is incredibly brittle. Strong leaders mitigate risk by planning for multiple potential scenarios, not just one. Just as investors benefit from diversifying the stocks in their portfolio, we too benefit from diversifying our identities and sources of meaning.

Ask yourself: How might I respond if I got a best-case, worst-case, and neutral outcome?

Choose curiosity over fear. Part of the reason uncertainty is so uncomfortable is that our brains have a natural tendency to catastrophize. But uncertainty can also be the birthplace of possibility. Research shows that when we’re able to approach uncertainty with curiosity instead of fear, we are literally able to see more potential paths.

Ask yourself: What is my anxiety about the future telling me about what I care about?

Was there a person or story from your research that completely changed how you think about uncertainty?

I open the book with the story of a couple who is having a drink at a bar in Manhattan. They’d been together for 17 years, married for 10, and were trying to figure out the future of their relationship. They decided to go their separate ways for a year, then come back to the bar exactly 12 months later, to the day, to determine their fate. “The year of living dangerously,” they called it. And you’ll have to read the book to find out what happens next ;).

What does your writing routine actually look like?

I write in spurts! I’m not a butt-in-the-chair-every-day-from-9-12 type, but I have a personal mantra: “write most days.” This takes off some of the pressure to adhere to a strict routine, and (hopefully) keeps me accountable for still getting words on the page.

How do you fuel your creativity?

I once heard that inspiration and creation are like inhaling and exhaling. This image has always stuck with me. I fuel my creativity by reading beautiful writing.

Morning routine?

Change my son’s diaper, wiggle clothes onto his body, cook some eggs, make the bed if I’m lucky--no time for cold plunges and 30-minute meditation here!

Book on your nightstand?

I just finished the new Lily King book, Heart the Lover, which I loved. It felt like eating a big bowl of orecchiette bolognese (my comfort food).

Most valuable career advice you’ve ever been given?

“Forgive yourself for not knowing what you didn’t know before you learned it.” It’s a quote that’s often attributed to Maya Angelou. I remember hearing it for the first time and feeling a weight being lifted from my shoulders. We put so much pressure on ourselves to know exactly what we want, to have a calling, but as a multifaceted person with varied interests, I needed permission not to know. I still don’t know what I want to be when I grow up — that’s part of the fun.

Thank you, Simone, and congratulations on a brilliant book that we all need! You can order How to Not Know from your favorite bookshop, and check out Simone’s work and other projects right here.

Reader Prompt: We're all navigating uncertainty and change — what helps you stay grounded when you don't know what's next? Please share in the comments!

Bookmarked: Boredom is the Price we Pay for Meaning

Making: It’s asparagus season and I’m making this tart!

Hat for a Cause: Love this chic baseball hat via Natalie Borton - 100% of profits benefit Chamber of Mothers

Fewer Better Fitness Faves: Truly the best yoga mat (and cute mat towel), leakproof water bottle w/ handle, very good workout leggings, free week of my favorite yoga class!

1:1 Business Mentoring: No-fluff strategy and support to help you tackle your large and small goals. Get support here

My Signature Online Course: Learn how to edit, organize, and elevate your home like a pro. To the course

Curated Product Recs: My fewer better faves for your home, life, and wardrobe. To the recs

I Wrote Some Books: Actionable strategies to clear clutter, get organized, & elevate your home and life. To the books