The Looking Glass: Changes and Confidence

Hello everyone!

A few letters ago, I mused on changing the format of this newsletter since I wasn’t getting as many questions, even though new subscribers were still poking in (if you’re new… Hi! 👋 Welcome!)

Since other parts of my life have been changing drastically, why not change this too? 😊Like moving to a new city, getting a new roommate, and chopping off your hair all at once!

First, on the look itself: It’s sparse, I know.

I switched over to Substack from Mailchimp and didn’t have many paint options to work with. That said, I’m relishing saving $150 a month and hope you can still pull up a (utilitarian) chair, have a cool glass of water, and settle in comfortably.

Second, on the content: I’m going with a three-part structure (which I loved from diving into other people’s newsletters. Hi James Clear!) One part will be product & design, one part leadership & team, and one part about personal growth, all exploring a particular theme.

Or, as I think about it: your product, your peeps, and you.

Who am I writing for? Those of you who know me well know that secretly, all my writings are essentially letters to myself. It’s the stuff that I need to hear. But, if you are like me—someone who loves building products; someone who is a designer/engineer/pm/researcher/analyst; someone who obsesses about working with others; someone who’d like to better understand herself—then maybe you will enjoy reading this too. It’s my sincere wish that these letters give you some things to pause and think about in your own journey.

I love hearing from you, so feel free to send me your thoughts and questions. Even though this is no longer in the q&a format, what you tell me always inspires the tap-taps of my keyboard.

Onward through the looking glass!

The Confidence Network Effect

One of my dear friends Annette has a signature in her emails with a particular saying: Confidence is a prerequisite for success.

Since we correspond a lot, I find myself staring at this quote all the time. I wonder why she chose it. And put it in big blue letters. And used the word prerequisite, which I hadn’t heard of since poring over course catalogs figuring out what it took to graduate.

Over the years, it’s struck me more and more deeply.

Here’s how I read it now: If you don’t believe there’s a chance you could do it, you will probably not try.

If you don’t think you deserve to win, or doubt you have what it takes to make it happen, success will slip through your fingers like water.

Annette made it her job to help those around her feel that confidence. She saw you for what you were—superpowers, angsts, warts and all—and she believed in you. I was on the receiving end of her powerful belief time and again, and I am so grateful to her for that. When someone believes in you that fiercely, you can’t help but believe a little more in yourself.

What else helps with confidence?

I think being in the company of those you admire.

Now certainly, this can be a double-edged sword. I don’t know about you, but I’ve had many an indigo evening flicking through social media awash with the amazing accomplishments of my friends—winning awards, announcing big-number milestones, stepping onto bright stages with aplomb—and I think to myself, “Why am I at home in my pajamas scrolling through all these stories when everyone else is out there working hard to achieve their dreams?”

But here’s the thing: when it’s someone you know making it happen, some little voice says Maybe I can make it happen too. When it’s someone in your circle who does that bold, daring thing, suddenly it doesn’t look so impossible. After all, you know them to be human. Just like you.

I’m pretty certain I wouldn’t have written a book if one of my best friends wasn’t already an accomplished author. It’s questionable if I would have been a designer had I not been seated with other designers on my first day at the office. I don’t think I’d believe it was possible to start my own business if I hadn’t seen friends and colleagues take those first steps. When they did, they de-mystified it for me. They showed me the inside story, not just the glamorous facade. I could ask questions and get answers. It became possible.

So. This week:

Whose confidence are you helping to build?

Whose company are you keeping to bolster your own?

The Confidence of Time

What are you able to do now that you couldn’t have imagined 10 years ago?

I bet there’s quite a few things on that list.

Now project that same gap into the future—what will you be able to do in 10 years that is hard to imagine now? Tell yourself that that list will be just as long, if not longer, than the first.

So much of what holds us back is our belief that we can do it.

In my twenties, I couldn’t dream of starting my own business. Nobody I knew well had ever done it before. My parents had always worked for large corporations. They extolled the virtues of stability, structure, support. They were immigrants who had already stretched into the far reaches of their capacity for risk by moving to a new country with empty wallets and incorrect tongues; they didn’t need another dimension to bet the farm.

I grew up in the fog of those values, though not those exact circumstances. So I tested the limits in my own little way—sure, I’ll work for a company, but it’ll be a startup, not a large corporation. Sure, I’ll study a hard skill so I can be a doctor, lawyer or engineer, but all my side time will go into drawing and writing.

It took me decades to break out of some of those beliefs, to finally call myself a designer or a writer. I don’t yet feel like an entrepreneur, but I hope in ten years, it’ll sit comfortably on me like a well-worn sweater.

What will you do in 10 years that is hard to imagine now?

The Confident Builder

In recent years, I started paying more and more attention to confidence as a litmus test in product reviews for “new behavior”-type initiatives.

What’s a “new behavior” initiative? It’s when you’re introducing a new solution to a people problem and looking for customers to change their behavior because of what you’re building. This is in contrast to “optimization” initiatives that seek to extend or deepen already existing behavior.

When you change the order of a series or steps to make it easier to complete—that’s optimization.

When you introduce a new product or feature that enables people to do things they previously couldn’t do before—you’re hoping for new behavior.

With optimization, it’s usually a good idea to try many little ideas and see what works and what doesn’t. You can often settle bets between people swifter and with greater clarity using A/B tests than using arguments. (Is top left or top right placement of the prompt clearer? Is “Confirm” or “Okay” more understandable?) Here, confidence matters less; curiosity and speed matter more.

But for new behavior initiatives, you can’t really experiment your way into a compelling vision by throwing stuff at the wall and seeing what sticks. You need to have belief in a set of core insights that provide the foundation for a solution. If you do not, the slightest ruffle—the first subpar result, the doubts or shades of others, the onslaught of a competitor’s march—will send you reeling.

Confidence is not the solution in of itself; rather it points to a team having done its homework in coming up with believable assumptions and insights, just like how fever is not the illness, but points to an invasion of foreign agents in the body. Of course, there is such a thing as arrogance, or blind faith, so a confident team doesn’t mean everything is hunky dory. But when there is a lack of confidence, I always try to understand why.

What builds confidence for those working on “new behavior” initiatives? The answer is simple: a deep understanding of your target customers.

When a team knows their market, knows their target customer, knows the problem that person faces deeply, knows her day-to-day and when she encounters that problem, knows her next-best alternatives—that confidence comes through in the product proposal. Those teams have a glint in their eyes and power in their voices. They have thoughtful answers when you probe them on why their solution looks the way it does. They don’t get harried when someone disagrees or disbelieves. They don’t crumple when their first solution doesn’t work. They have confidence that their problem matters, that some of their key assumptions are correct, and that they’re on the right track.

Those teams are unstoppable, and they will find success.

Wishing you a wonderful week,