Coaching Toolkit: Sitting With the Unknown

Practices for navigating uncertainty even when it's uncomfortable

When I left Google 15 years ago, I was only a year and a half out from college graduation and had put in my two-weeks notice without a plan for what I was going to do next. I walked away from a great team, a stable salary and career path, unvested stock options… into the complete unknown.

Of course, I had my doubts. I told myself I could always go back to Google if there wasn’t something better out there. But what if they don’t want me back? What if I never find something else?

But there was also another part of me — the steadier, quieter one — that trusted I’d figure it out. I didn’t know what was next, but I was curious enough (and maybe just naive enough) to believe there was something else out there for me. That move led me into the world of early-stage startups — it’s hard to believe that back then, I knew nothing about startups, and now they’ve been my professional life for the last 15 years.

Years later, I left Medium without anything lined up, or as a coworker referred to as “pulling a Jean.” Last year, I did the same when I departed my latest startup.

These transitions, which seem relatively unusual in the corporate tech world, have led me to reflect on the mindsets and tools I rely on during such times, and how I can share them with others.

The part we tend to skip over

We’re taught to be good at execution: set a goal, make a plan, follow the steps. School conditions us this way, and early careers reinforce it.

So when we hit life’s big transitions, we often reach for that same playbook. We want the roadmap so we can strive for the next milestone.

But when we immediately reach for the next thing, we miss the messy, uncomfortable middle, that liminal phase between “the old thing is gone” and “the new thing has emerged.” The space of not knowing yet.

Most people try to leapfrog over that part, because it feels so unsettling.

It’s hard to make space. Not only is it personally uncomfortable, it’s also socially unacceptable outside of “sabbaticals.” People will ask you what’s next, and you’ll feel pressured to give an answer that’s more goal-oriented than “I don’t know.”

But it’s in this space that you get in touch with what you really want in the next phase, rather than what society, capitalism, or the people around you tell you to want.

Savoring the messy middle

Every so often I dream I’m back in college, right before graduation with no idea what’s next. I start to panic — job applications? grad school? a new city? a year off? — but under the anxiety there’s also this electric sense of possibility. I wake up unsettled, but buzzing with: I could do anything. What will I do?

That dream feels a lot like the transition I’m in now. One moment, I’m terrified and wondering what I’m doing, and the next, anything seems possible.

And both can be true, I can feel scared and excited. But as much as possible, I’m trying to stay in that space of exploration and possibility. Because you can know that you need space to figure out what’s next, and still find yourself completely filling that space with worry about finances or employability instead of exploring what you truly want.

What if, instead of meeting the unknown only with anxiety, we also met it with curiosity?

Could we learn to even savor the mess, to savor the unknown and that sense of anticipation?

One thing that’s helped me slow down and delve more into curiosity is always returning to a deep knowing that I’ll be okay. Each time I face uncertainty and come through it, I add another piece of evidence. So when I slip into thoughts of scarcity or desperation, I can look back and remind myself: if I stay patient and curious, clarity will emerge.

Foundational practices for uncertainty

As a somewhat impatient person, waiting for clarity to emerge can sometimes feel torturous. I can feel behind even when I’m just a few days into an exploratory phase. There are so many things outside of my control, but I’ve also learned that there are many things I can control.

When I sense a transition approaching, I have to remind myself to double-down on foundational practices that create a more conducive environment for me to figure out what’s next.

The first is sleep. A few years ago, after listening to a podcast episode with Matthew Walker (author of Why We Sleep), my husband Naveed and I started taking our sleep very seriously. Instead of thinking about what I wanted to do that year, I made the assumption that if I just focused on getting good sleep, good judgment and dynamic attunement to what I want would follow. Sleep became my first foundational practice.

The next foundational practice that has re-emerged this past year for me is journaling — it helps me notice what I’m drawn toward, what repels me, what sparks curiosity.

While I think sleep is probably important for everyone, your own foundational practices that create an environment that helps you navigate uncertainty may be different. It could be yoga, meditation, weightlifting, eating well, or hiking. Start to notice what it is in your life that helps you clear your mind and be more attuned to what you want.

Coaching Toolkit: Practices for Sitting With the Unknown

It’s easy to think of a situation as something happening to you (being laid off, death of a loved one) versus something you’ve decided for yourself (quitting a job, ending a relationship), but in any situation, there are things in your control and things outside of your control.

Navigating the uncertainty of these transitions is uncomfortable, but it’s also a skill you can build. These are the practices I return to when I feel adrift.