“What do you do when you’re not sure? That’s the topic of my sermon today.”

Jessica Zwaan
5 min readMay 3, 2024

In 2020 when we were sent home from the office for what we all were sure was “two weeks of working from home”, who among us began to feel something lurking under the surface that was hard to describe? Life wasn’t exactly moored before that moment, but it was at least somewhat calculable.

In an instant, everything we took as indubitable started to change. And now, as we grapple with what has continued to unfold before us (to us?), we seemed to agree that the “new normal” is kind of, er, chaotic at its best and demoralising at its worst. Tedious and stressful. The very worst of both worlds.

And work, oohhhh boy, don’t get me started on work (ok, fine, because that’s what the blog is about). Everyone seems to agree that we, all of us, are tired. Tired, doubtful, and almost existentially uncomfortable. HR is grappling with office/remote/hybrid/oh-wait-no-ok-office/hybrid-but-coworking/remote-but-not-global, Sales are sadly limboing under Sales Quotas, Annual Recurring Revenue is slowly becoming Annual Recurring Renegotiation, Finance have reforecast that damned budget at least once a month for the last — what? — 36? Woof. What’s going on? I sure don’t know.

My favourite play, Doubt, recently had a revival on Broadway. (Impeccably timed, I think.) In Doubt, we are left in the well of our own uncertainty, wondering, “who was wrong?” but knowing we never need to answer to anyone in particular. Being filled with unanswerable questions you cannot answer is fine after a play (good even) but is exhausting after 8 hours of spreadsheets, emails, and board packs. And, unlike after Doubt, we are expected to know. Our jobs seem to depend on it. Our teams want something — anything — they can cling to with surety.

“It is a crisis that strikes at the very heart and soul of our national will.”

How do we lead when we’re uncomfortably unsure?

Where do we turn as leaders and company builders when we, and our team, are tussling with feelings we cannot resolve?

At work, we are expected to know things. That’s fair enough. We should absolutely know at least some things. We should know how to use Xero, and connect a Zapier connection, and read API documentation. But was it ever really reasonable to expect ourselves to know some of these other things that have come into question: like what the economy will do, how to convince people AI won’t replace them, and if our graduates will make friends over Zoom?

Look, it’s incredibly (incredibly) important that we have some theories about how we may approach these big questions, but let’s explore the idea that pressure to Get It Right first time might be a part of the problem. (Tedious and stressful.)

“What is Doubt? Each of us is like a planet. There’s the crust, which seems eternal. We are confident about who we are. If you ask, we can readily describe our current state. I know my answers to so many questions, as do you. What was your father like? Do you believe in God? Who’s your best friend? What do you want? Your answers are your current topography, seemingly permanent, but deceptively so. Because under that face of easy response, there is another You. […]
It is Doubt (so often experienced initially as weakness) that changes things. When a man feels unsteady, when he falters, when hard-won knowledge evaporates before his eyes, he’s on the verge of growth.” — John Patrick Shanley, Preface of Doubt.

When life and work, increasingly indistinguishable from each other, are accompanied by feelings of uncertainty and malaise, it’s a moment to revisit long-held truths and begin to challenge them from first principles. And maybe, being wrong about some things, is the door to being even more right than we were the first time ‘round, before the whole stability-thing went kablooey.

Start with a hypothesis

When facing a situation we’ve never faced before, it feels natural and learned, to immediately seek the correct answer. We were professionally brought up in a world where it existed out there in the zeitgeist. Someone, somewhere, had seen it aaaalll before. We just had to find the right answer and make it happen, and all would be resolved. But now, it’s not so easy. And that sucks, it does. It sucks. But it maybe doesn’t have to, you know?

A hypothesis at work outlines your expectations regarding the outcomes of your project. It serves as a preliminary response to a problem or question that has yet to be resolved. A well-crafted hypothesis, however, isn’t merely speculative; it’s grounded in your existing theoretical frameworks and knowledge. Crucially, it’s formed in a way that helps you try to work it out, to be creative, to explore.

This means we have a new type of challenge to rise to, and one which may give us a new kind of satisfaction and joy, one of learning together how to navigate this whole thing, and maybe shake off some of the feelings we’ve harboured for probably (almost absolutely) far too long.

“But wait —” you cry, “We can’t tell our 400 employees that we only have a hypothesis on these things; they’ll leave, they’ll lose faith, they’ll never trust our decisions.” Sure, before — before, people looked to leaders for answers to questions we should know, but most people seem to agree that the world is just like, wildly different now. The old world was Christian Bale in American Psycho, the new world is Christian Bale in the Big Short. We should release ourselves from anachronistic expectations. It is okay to break the mould and look at things differently, to save ourselves from something perhaps much worse. It is okay to tell your colleagues you need to work it out, ‘look for markers’, to discover the answer together.

Your team is likely more interested in transparency and involvement in company operations than ever before, research is pretty clear that younger generations want to change how companies are run. Now’s probably the best time to ask them to help you prove your hypothesis.

When the Gutenburg Press was invented, it did make book production faster, but it would still take three years to complete one copy of a Bible. It took almost 1000 years before we had the modern Publishing Industry. We’ve been in this new era of life and work for less than that time. We’ve collectively, the whole world, printed exactly one Bible since that freaking weeeeirddddd day in 2020. Whenever you’re worrying about: whether or not you’ve got it right on AI, or Remote Work, or freaking — Slack, I dunno?? — just think about this. We’ve printed exactly one Bible, we still have so much to learn.

Ok that’s all from me, folks. 👋

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I talk plenty more about this way of working, and how to use product management methodologies day-to-day, I’ve been told it’s a good read, but I’m never quite sure.

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Jessica Zwaan

G’day. 🐨 I am a person and I like to think I am good enough to do it professionally. So that’s what I do.