The confidence that comes after dressing up in a giant hoop skirt

In 2021, I played Mother Ginger in a Marin County production of “The Nutcracker.” With a white beehive wig and gaudy French pancake makeup — a beauty mark to boot — it took 2-3 people to get me dressed backstage in a pink/red/cream dress with a giant hoop skirt.

I should say I'm not a trained dancer. Sure, I took the required theatre directing classes in university where I was part of the acting ensemble. Was I the most graceful? No. And, yes, I was the captain of the speech and debate team in high school so I'm capable of doing performative things under pressure. But I didn’t at all feel prepared.

When asked, my first instinct was no. Wave my hands, say, Thanks, I'm sure someone else could do it better than me. It’s fine. But then I thought: Why not? It could be fun. And I could do it with my kid.

Word got around quickly. Especially with my kid’s friends. One day during rehearsals dropping off at school, a cluster of them came up to me and asked, "Are you in Nutcracker?" Yeah, I said.

"Are you wearing a dress?" Totally, I nodded. "But I'm also wearing my own boots," I said. "And I'm going to be wearing makeup too. A lot of it. My face is going to be white white white."

The kids looked at me blankly and then ran off.

For a 4-5 minute scene in the whole production, it's a bit ridiculous. It's comic relief amidst the other dances in the land of sweets with a towering figure, often a man these days, with unruly children (called Polichinelles or Bon Bons) bursting out from under the enormous skirt.

Personally, I think it's also the Russians from 1890s poking fun at the French. The woman who did my makeup told me this.

But it was worth it. The months of rehearsals, the nerves beforehand, the awkwardness of being the least trained person on stage (most likely). All of it.

Bravery isn't about doing something without fear, it's about doing the scary thing while you're scared. Fear, anxiousness, and other imposter monster feelings will always creep in. I appreciate the way that Glennon Doyle puts it: "Brave is not something you should wait to feel. Brave is a decision."

The glittering vision of success doesn't often bring in the character of fear. It's like Voldemort, we don't speak the villainous name. We hope that the fear will vanish. But it won't. It usually doesn’t.

In Susan Jeffers' book, "Feel the Fear... and Do It Anyway," she talks about how confidence doesn't show up first. You don't feel ready and then act. Rather: you act, then confidence builds gradually. The only way fear shrinks is by doing the thing repeatedly, not by thinking about it more and sitting with inaction.

Doyle's not telling you to ignore fear in “Carry On, Warrior.” She's saying the fear won't disappear, so you do the thing anyway. And as Jeffers says, the confidence comes after.

So how does this example being Mother Ginger in the Stapleton Ballet production play out elsewhere? Great question.

I’ve been in situations where someone might suggest some manner of talking to customers in product work. Sometimes, it's me. Sometimes, it’s someone on my team, in product or design.

Let's give it a name. Let's say we're working on a new unified dashboard or revamping an onboarding flow. And the question gets asked, How do we know our customers want this?

This is usually followed by an awkward silence.

You see where I'm going with this. It doesn't have to be customer interviews, which IMO work super well. It can be a customer support log. It can be call notes from the sales team. Hell, I'll even take a Net Promoter Score (NPS) survey. Sometimes, a set of dusty personas get trotted out with Maria the manager, Stephen the single dad, etc.

In my example, let's rewrite it and say that the team is open and they say, Yes. Let's do that. Everyone nods. It makes perfect sense. This happens about 25% of the time.

Then, a few weeks later, they haven't done it. The team has spent their time rewriting and reworking the product roadmap. And they knocked out a few key features "that'll really make a difference." And all sorts of other activities — backlog grooming, standups, maybe even a pre-mortem.

They've done everything except talk to an actual person. They've kicked the feature factory into high gear, just hoping that people will buy. No evidence.

When asked some version of why they didn’t talk to customers, the answer is always some version of the same thing: they're not ready yet. The timing isn't right. They need to understand their market better first, do some competitive analysis. The questions aren't perfect. Any number of reasons.

What they're really saying is: I'm scared of what I'll find out, so I'm waiting for that to go away.

But it won't. And while they wait, they're building on assumptions. Getting more attached to the idea, the idea that hasn’t been validated. Buying their own press.

The fear isn't the real problem. The real problem is skipping the hard part because you already think you know the answer.

Staying curious is harder than being certain. Asking a question you don't know the answer to is scarier than pitching an idea you've been polishing for months. My friend Dave Gray talks about how no one likes a know-it-all, especially one that's right. And how they’re even worse when they are.

The only way through is to do it while you're still nervous. To talk to customers who might say something that breaks your plan.

That's when everything changes.

For my Mother Ginger bit, it took a couple months of rehearsals for 15 min of fame, about. People laughed, they clapped along, they cheered, the kids loved it. Now, imagine what you could do with talking to just 10 customers.

Not to validate your idea. Not to check a box. But to actually understand what they need, what they want, their pains, and their goals.

What are you waiting for that you could do scared instead? Not recklessly. Not without thinking. Just while you're still nervous. What would it look like to talk to 1-2 customers a week for just 30m?

How does that sound? Hit reply.

Until next time,

Skipper Chong Warson

_{Making product strategy and design work more human — and impactful}

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