The Looking Glass: Love the problem

3 mantras, your early-stage start-up is not a good fit, and my asian heart

Hello readers!

This week’s tidbits:

1. Love the problem
2. Your early-stage start-up is probably not a good fit for someone who…
3. A design + data person
4. From the archives: On taste (part 1)

For paid subscribers:

1. Subscriber mailbag: What mantra(s) do you live by?
2. Loving someone
3. My asian heart

It’s June! It’s my birthday! It’s back to sunshine and summer strawberries and speaking at events again!

I’m going to try something new — variations on a theme in each newsletter installment.

The theme of this one? Love of course.

Become a paid subscriber to support my bad poetry and oh-so-sappy heart!

Love the problem

In the youth of my product life, what I loved best were the solutions.

See, solutions gleam with the luster of the new. They smell like promise. They glow with innovation.

And I, as their creator — a modern day Leonardo I like to think! — am a painter of vision.

Got a minute? Don’t mind if I suggest you 3 app ideas.

Got a complaint? Here’s 5 feature ideas to address that.

You might be like me. You might be thinking, Well isn’t that how it’s supposed to be?

(You can sense the but coming, can’t you?)

Here is the problem with loving solutions: they are like putty, like paper in the wind. They do not last.

Solutions do not last because they all suck in some way. Trust me on this.

If you are not prepared for the fact of their suckage, then when someone else points out the solution’s flaws, you will get defensive and irrational.

What’s more, a single solution is a complex, multi-faceted beast. It may address multiple problems at once, but in varying degrees of success. For example, Google Search helps you do your homework, find a restaurant, catch up on the latest news, shop for a new summer jumper. It does not achieve these things equally well.

Or, a single solution may work well for some specific people, but not for others. For example, Gmail may be lovely for you, but not for folks who send hundreds of emails a day.

When you love a solution, you will inevitably try to get people on the train of that dazzling solution, which means you will sweep the nuances mentioned above under the rug.

This will ultimately be destructive to the real goal of solving the problem.

You see, love of a solution is different than love of solving a problem.

When you love to solve a problem, what you are really dedicating yourself to is… *dumdumdum* the problem.

A problem that is big enough and rich enough to capture your imagination and stoke the fires of your creativity.

A problem of near-infinite variation and complexity that even after millennia of walking this earth, we humans are still befuddled by it.

A problem like that is no match for any one solution.

No, to love a problem like that is to meet it with dozens, hundreds or even thousands of solutions. To recognize that perfection is impossible. To love a problem like that is to face frustration and closing walls, to meet rejection and rough compromises.

But perhaps — just perhaps! — through the humble process of asking and attempting and asking and attempting and asking and attempting — we take the tiniest of steps forward. We make progress. We make something of ourselves.

Love the problem, and in its swirling abyss, find the reward.

Your early-stage start-up is probably not a good fit for someone who…

1. Has only worked at big companies with no relevant side projects
2. Has just come out of a bad experience at a competitor’s start-up
3. Is focused on work-life balance in their next chapter
4. Is planning some big life expenses, like buying a house
5. Operates best in an environment of structure and clarity
6. Dislikes failing more than they like discovering
7. Feels apathetic about the idea of personal growth

A design + data person

I now introduce myself as a design + data person.

What a joy it’s been to build Sundial these past years! Yes, I fell into all the first-time-founder traps — being far too naive (ha!) Not prioritizing ruthlessly enough. Bringing big-company habits that don’t serve a scrappy start-up.

But I also really really really learned to love the art of data. Because data is in service to making good decisions, and good decisions = better products.

Making good products is hard and ambiguous and human. How do we know our decisions lead us closer to our mission? How do we prioritize better and faster? How do we marry the heart of a creative mission with the rigor of operational excellence?

There is such a thing as losing yourself in trees of metrics and forgetting to see the forest.

There is such a thing as making subpar decisions based on ego when the facts suggest a better path.

I believe there is a golden, goldilocks place and what it looks like is opinionated intelligence.

This is my greatest learning from working with my data superstar co-founder Chandra Narayanan, our amazing team, and our early partners. And we’re determined to help every company in the world get there.

Today, we’ve got a new website up and are opening up our waitlist publicly.

If you’re a fast-growing subscription company getting close to 100K+ users eager to build a great data foundation and find actionable insights to power your decision-making, come talk to us at sundial.so!

From the Archives: On Taste (part 1)

In the fourth grade, your entire class put on a winter musical spectacular. It was everything your little nine-year-old heart could hope for: Singing! Dancing! Glittery snow and beaming parents! This being an inclusive school event, everyone was to participate in belting out politically-correct Christmas classics like Jingle Bell Rock and I’m Getting Nuttin’ for Christmas. But the biggest, awesomest, wickedest act was the solo. The grand finale. The coup de grace. And yes, Ladies and Gentlemen, it included a CONFETTI SNOWSTORM.

Hellz yeah, you were trying out for that solo.

Now, recall that you are nine. This was the period of your life in which you fancied yourself an Ariel, whose dazzling voice could produce miracles like transforming fins into legs. Every night in the shower, you belted out Part of Your World like you could never get enough gadgets and gizmos and thingamabobs. (Twenty years later: not true.) There was something magical about the way your notes reverberated all bright and frosty off the glass. You liked to sing — nay, you loved it. And you thought you were pretty damn good at it, too.

Even after all these years, you can still remember the audition for the solo. The song in question was some sad, soulful Eponine-esque lament about how a certain snowman’s cold, cold heart proved to be an insurmountable obstacle to a budding relationship. You practiced it a dozen times each day, in front of your parents, your grandparents, your next-door neighbor, your imaginary dog. When the moment of the audition arrived, you stuck a big grin on your face, walked out in front of all those teachers and students, and belted out your love for that frozen ball of snow. Afterwards, there was scattered applause. You bowed and went back to your seat.

Alas, you didn’t get the part. The honor went to a girl named Lisa, and when she delivered the final Mariah-inspired ooooOOOO-EEEE, the crowd leapt to their feet, cheering wildly. Of course you were disappointed that it was her and not you standing out there in the spotlight, in the downpour of all those fluttering, glittering pieces of confetti snow. But you shrugged it off. There would be other performances. Life goes on. Meanwhile, you happily continued singing your Little Mermaid songs in the shower.

It wasn’t until a few years later that the truth finally hit you, over a Christmas morning spent playing with a new family camcorder. You thought it would be fun to record yourself singing. (You thought like an idiot.) You hit replay. And then, this simple fact split the ceiling and slapped you hard across the face:

You were god-awful at singing.

There is no polite way to say it. You sucked big-time. You’re practically tone deaf. Those notes that always sounded so bright and clear in the shower were actually muddled and warbly. You sounded like some sort of tipsy animal, and the louder and more passionately you sang, the more it it called into question whether you weren’t trying to sing some entirely different song altogether.

To say that you were devastated would be putting it lightly. Here was a thing that you did and loved, only to discover that you did it poorly. Broadway was not in the stars. Even singing Happy Birthday was suspect. More than that, the realization shook your faith in yourself. Since as long as you could remember, you fancied yourself competent at this one thing. Turns out you were terribly, horribly wrong. So what else are you wrong about?

What else are you miserable at, and maybe everybody else knows it, but you’re too blind or proud or delusional to see?

Ira Glass of This American Life, in one of his most quotable quotes, says this of beginners:

All of us who do creative work, we get into it because we have good taste. But there is this gap. For the first couple years you make stuff, it’s just not that good. It’s trying to be good, it has potential, but it’s not. But your taste, the thing that got you into the game, is still killer. And your taste is why your work disappoints you.

Ira’s words were meant to be inspirational. He goes on to encourage beginners to never give up, because only with persistence will the work get better — slowly but surely, inch by painstaking inch — until it finally lives up to that ideal of taste.

That quote is etched across your heart. You couldn’t agree with Ira more. You turn to those words time and time again when your work feels like crap, when you wish you could bury it in a ten-feet hole and pretend like you never came up with such shit in the first place.

But his advice doesn’t address your greatest fear, born through the shame and folly of thinking that you were ever good at singing:

What if your taste is the thing that sucks?

Continue on to Part 2.

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