A Practical Guide for Navigating Ambiguity

Five lessons from learning to thrive in uncertain times

I would not describe my career as ‘waterfall’. There’s no calendar or longterm map for where I go next beyond a set of guiding principles and a desire to build communities. I am constantly doing the next right thing based on the information I have at the time.

This is exhilarating to me, but it’s horrifying to many, many other people. It made me a natural fit for a career in program management. Program managers always talk about “thriving in ambiguity” as a critical behavior for success. What it means is an ability to bring order to chaos, keeping a level head amid a sea of uncertainty, and successfully motivating teams towards common goals even when the “fog of war” is thick.

Lately, there’s been more ambiguity than normal in my life — and, for others (especially in tech), even more. There hasn’t been a day since late 2022 that goes by without talking to at least one person about “what all this means,” especially for those recently needing to seek new positions. There seem to be more reorganizations than ever, busier stakeholders juggling more, and a palpable longing for knowing what’s next. All of this compounding on top of three years of a pandemic is leaving people exhausted, frustrated, and worried.

While it’s been especially difficult recently, I always try to remind myself that ambiguity is a constant. For example, in my ~7years at Google, I’ve gotten to work on Google+, launching new features like Communities and Topics before eventually turning down the consumer version for an enterprise rebrand… and then turning that down too. More recently, I originated the Internal Community Management Team to enforce Google’s Community Guidelines—an unprecedented effort at the time which has become industry standard. None of that was easy to do.

Ambiguity brings stress, sure, but it also brings opportunity.

Throughout the past several months and years, I’ve either coached people through ambiguity or received invaluable coaching myself on how to get through my own. Here…