Smart Questions

One of the biggest mistakes you can make is thinking that asking a lot of questions will make you appear stupid or uninformed. Nothing could be further from the truth.

If you feel this way, I get where you’re coming from. You’re presented with some new information and there are parts of it you don’t understand, but you feel like you should understand it. You get this sense that everyone else must absorb this instantly on the first go around, so if you don’t get it then there’s something wrong with you. So you clam up.

But from the point of view of the other person, nothing makes you look more foolish than not engaging at all. The reality is that everyone learns differently and so no single approach can perfectly teach everyone – so everyone should have questions. The person that doesn’t have questions just looks like they’re not engaged; like they don’t care enough to ask for clarification or they’re not thinking critically about what’s in front of them.

You signal intelligence and ambition with lots of questions, not with few.

One of the reasons that questions signal intelligence is because you can’t even ask questions without at least elementary critical thinking and basic knowledge of the topic. If you dropped me into an archaeological dig in Egypt and started telling me high-level stuff about the rock samples, I’d probably just nod along – not because I understood everything so fully that I didn’t need to ask questions, but because I’d be so lost I wouldn’t know what to ask. I don’t know the first thing about archaeology or Egyptology or any of that stuff. I’m not even sure I used those terms correctly.

So ask away! I promise you, no one has ever said, “Gee, that person sure had a ton of intelligent, challenging questions and engaged with us on the answers. What an idiot.”

Product or Concept?

You have to know what you’re selling.

If you’re in automotive sales, you sell cars. You convert the physical features of your product into vibrant stories in the minds of your customers (if you’re good, that is), and you differentiate your product from the competitors’. Your primary obstacle is convincing your customer base that your car is better than the other guy’s.

If you’ve only ever sold cars, you might not realize that there’s an entire extra step that is absolutely crucial to the sales process, but that you are fortunate enough to get to skip. Because before you can get into why your car is better than anyone else’s, your customer has to believe they can benefit from a car, any car, in the first place.

You get to skip this step because, at least in the United States, the benefits of a car are well-established and most people would like to have one. There are exceptions, like NYC (where nobody drives because there’s too much traffic, haha), but for the most part you don’t have to start your sales process by convincing an automotive skeptic that there are benefits to car ownership.

That’s not the case with every product or service, though! In today’s modern world of fast and awesome innovation, lots of companies aren’t just improving on existing stuff, they’re creating whole new categories of stuff.

Sometimes, though, really brilliant innovators sell their product or service like they’re selling cars. They go right into comparison sales, trying to convince prospective customers that their widget is the best of all available widgets, and it’s so much more effective and a better value and so on. But the customer doesn’t care about widgets yet, so the sales falls flat.

It’s a tempting trap for the first-mover to think “I’m the pioneer in this field, so I have no competition! So sales will be easy!” But you do have competition: Your competition is inertia. The status quo. Ignorance.

Before you sell a product, you have to sell the concept.

That’s a totally different sales process. On the macro level, it involves a lot of “awareness marketing,” which most likely includes lots of free content, lots of helpful information, and lots of market engagement where you show off helping people. People will not beat a path to your door if you build a better mousetrap – the world has too much noise.

On a micro level, it involves really digging in to the problems your customer is facing. Finding out what issues they have, what difficulties they’re trying to overcome. If you can illuminate their problem and highlight that you have a solution, then selling the concept is selling your product, because the sale is going to be made at that point.

This can be very emotionally difficult for the innovator. That person has spent a large portion of their life immersed in this; he or she lives and breathes the value of their product and how it can help people solve an essential problem. To them, it’s crazy that the whole world doesn’t immediately see the benefits. But in general, the masses are slow to adopt and skeptical of these things at first, and that can feel very frustrating to the innovator. They want to help people, not convince people that they need help.

Almost every salesperson I’ve ever met has had that particular moment of frustration at some point in their career. “I don’t get it – the thing I’m selling would be great for them, it would literally save them money and make their life better, it’s perfect for them. I just don’t understand why they wouldn’t want it.” It’s a frustrating moment. But the reality is that it’s on the shoulders of the salesperson to show that there’s a problem worth solving.

The concept comes first.

Something Else

When my first child was born, I made some ambitious resolutions in terms of how I would behave as a parent. One of the promises I made to myself was that I would never be the kind of parent that just said “Because I said so!” when my kid asked difficult questions.

Allow me a moment to say: Bwahahahahaahaha!

I feel like a lot of new parents make that promise, but the problem isn’t what you think it is. You think the problem is going to be that your child’s endless intellectual curiosity will overwhelm your patience and in frustration you’ll be a tyrant. So you decide in advance that you’ll always discuss things rationally with your child, welcome open inquiry, and encourage their love of learning.

But that’s not the problem at all! The problem is that these little weirdos are absolutely insane and the things they ask make no freakin’ sense.

Things my kid has asked me:

  1. “Where is the place that doesn’t have chicken nuggets?” Uhhh… what?
  2. “Can I have some?” Pointing at absolutely nothing, nor was I holding/eating anything. When I asked “Some… what?” she had no answer.
  3. My favorite: “What does something else look like?”

What does something else look like?

I was not prepared to answer questions of this level of existential severity.

But it’s all part of the process. Kids get language in such weird and interesting ways. They’re just collecting little bits and pieces and assembling them in different ways until it works. They don’t know the rules, so they’re just trying to get across their point. Interestingly, I discovered what each of the above nonsense questions actually meant with a little detective work:

  1. When asking about the place that doesn’t have chicken nuggets: I realized that whenever we went out to eat as a family, we only went to one of two kid-friendly restaurants. One was Chik-fil-A, and the other was a local pizza place. She couldn’t remember the words for “pizza” or anything like that, so the best way she could describe what she wanted was “the place that doesn’t have chicken nuggets.”
  2. Because we were always introducing her to new foods, whenever we ate anything, we’d always offer her a bite and say “Do you want some?” We said the word “some” approximately a billion times more often than we said the word “food,” so she thought the word for “things you eat” was Some. She was just hungry.
  3. She had overheard me describing a family friend, a bit of a zany character, and I’d described him thus: “He’s something else, all right.” I hadn’t even realized my daughter heard me, or that she would so heavily imprint the term.

So while they’re absolute maniacs, there is a method to their madness. They’re collecting bits of pieces of the world around them, mashing them together until they fit. They get better at it.

What I love about this is it’s almost totally free-form. Kids pick up their native language with no formal instruction. They make a TON of mistakes, but so what? They make it work. They learn everything that way – one of my favorite parenting moments was watching this time my daughter was playing with a cup under the bathtub faucet. She was filling the cup, turning it upside-down, and filling it again. The look on her face would make you think she was watching the moon landing. She was learning all these facts about physics and gravity and how her environment worked for the first time and I could just see the gears turning in her head, and it was wonderful.

Don’t lose that now that you’re an adult. That is still absolutely, 100% the best way to learn things. Just jump in and pick up pieces and gradually mash them together with other pieces you pick up. View each individual piece as a happy success. Don’t worry about the end goal as much – kids don’t know what full command of the language looks like as they’re learning it.

We’ve been conditioned to feel this formalized, credential-based way of learning is the only way to get good at something, to pick up anything new, and it ends up being a huge barrier to us. We think we can’t learn anything new because we don’t have time to take a course or money to pursue a degree. But that’s such a terrible way of looking at the wonderful chaos of facts and knowledge. The better way is immersion, jumping in and using the mistakes to make better ones until you’re making what you want instead.

That’s what something else looks like.


My oldest daughter is at that perfect age where curiosity about what her dad does has transformed into an active desire to participate. I love it.

When I work out, she can’t wait to spot me or help or work out alongside me. When I’m blogging, she wants to talk about what I’m writing or even type a few words. She wants to type work emails and read them back to me. We read together, side-by-side, drinking the smoothies we made together.

I am so, so grateful for this. I tend to be a bit of a workaholic, so if my daughter wants to participate when I’m working, then we get great daddy-daughter time as well. We get to engage intellectually in a meaningful way.

I’ve made a commitment to say “yes” to as many of these requests as I possibly can. It’s so easy to reflexively say “no.” To try to keep your kids out from underfoot while you’re busy, and then to try to dedicate some specific corner of your schedule to “spending time with the kids” specifically. But that little corner shrinks and shrinks, and soon you’re listening to Cat’s In The Cradle and sobbing. I don’t want that.

I’d rather have a sidekick. An awesome little mini-adult that exists in my world, instead of a child that I force to stay in her own. A smart, rad human that learns to be a good person by helping me be a better one.

Plus, you’ve never had an accountability buddy like a seven-year-old that’s decided that your workout is daddy-daughter time! No skipping for me!

What To Do While You’re Deciding What To Do

I’ve noticed a particular pattern of behavior that seems to trap a lot of people.

Many people seem to treat deliberating as a distinct action. You meet someone who’s a recent graduate and ask what they’re doing now that they have their degree, and they say “I haven’t decided yet.”

Okay… but what are you doing? Right now?

Deliberating isn’t discrete. It’s fine to take a reasonable amount of time to gather information and make a subsequently informed choice, but while that’s happening, you should absolutely be doing literally anything that develops yourself.

Consider two recent graduates, Goofus and Gallant. Both graduated the same year from the same school, and both are unsure of what they want to pursue with their degree. Both initially feel pretty lost.

So Goofus does very little. He lives with his parents or with friends so his costs are low, but he subsequently makes as little money as possible. He considers lots of jobs “beneath him” and therefore doesn’t work much. The problem gets worse over time, because every year he compares himself to peers that have been advancing in their careers, and thus puts even more jobs in the “beneath him” category. Five years after graduation, he has virtually nothing to show for it, no return on the investment he made in his degree.

Gallant also feels lost and unsure, but he took some good advice from someone and figures that while he’s figuring out his ultimate goal, he can commit his life to being in service of the day he figures it out. He doesn’t consider any work beneath him; money is money, and he wants to have a lot of it saved. He also keeps his costs low by living with parents or friends, but he makes as much money as he can and squirrels it away. He waits tables, drives for a rideshare service, picks up entry-level work in other fields if they’ll have him. In his spare time, he teaches himself new skills (he doesn’t worry about what, just learns!) and makes sure to meet new people. Chances are very good that Gallant doesn’t go anywhere near five years without deciding what to do, but let’s say it does.

So now we have Goofus and Gallant, both five years out, and on the same day they both suddenly come to the decision about what it is they ultimately want to do. Look how far ahead Gallant is! He has money saved, so he can be mobile – he can move to a new city that’s a hub for his chosen field, or he can buy a certification course, or even just live off his savings while he interns or apprentices. He’s valuable to employers because he’s kept his skills up to date and kept himself in the active workforce. He knows a lot of people so he can network his way towards his goal. In short, even though he didn’t know what he’d end up wanting to do, he was preparing anyway.

Goofus, on the other hand, is in bad shape. He found out what he wants to do, but he’s wasted years of his life. Whatever he wants to be, he’s now at square one – and actually, he’s worst than that because he has five years of bad habits weighing him down.

That’s the obvious benefit of this style of thinking. But there are at least two major other benefits:

  1. The more proactive you are, the less time it will actually take you to decide what to do. Goofus and Gallant wouldn’t have taken an equal time to make their decision in reality. On average, the more stuff you do, the more likely you are to get the insight, information and inspiration you need to find your calling. It’s not inside your head – it’s out there, in the world.
  2. There is at least some chance that you never decide what your “purpose in life” is. Instead of five years, it could be eighty. If that were the case, would you rather spend those eighty years like Goofus or like Gallant?

While you’re “deciding what to do with your life,” focus on other goals. Make money. Stay healthy. Keep your costs low. Stay mobile. Learn like a sponge. Be devoted to self-improvement and open to the world. Don’t sweat the details; don’t worry if you’re learning the “right” thing or improving in the “right” way. You can change course a thousand times if you want. In fact, that might not be so bad.

And if you’re saying to yourself, “this is great advice… five years ago. I wish I’d done it, but now I haven’t. I’m a total Goofus, so what do I do?”

It’s never too late.

Notes, September 2019 Edition

Here’s some music that I love. Some old, some new, some popular, some weird. Just good stuff to fill out your playlists.

Bastille – All This Bad Blood. This was a suggestion made to me, and I was excited because it wasn’t the style of music I gravitated to naturally. It turned out to be incredibly powerful music. “Daniel in the Den” is probably my favorite song on the album, but the whole thing was very emotional and rewarding to listen to. Give this one a listen on a long drive or some other time when you can really absorb it.

The Mountain Goats – The Sunset Tree. I’ve been crazy into The Mountain Goats lately. Something that happens to a lot of people, I think, is that they naturally rate music from their own adolescence really highly; the power of nostalgia is really strong. Even though I only discovered these guys in the past year, their music is exactly the theme of my own adolescence and so they manage to evoke as much emotion from me as any of the fight songs of my youth. I’m not sure if that’s a good endorsement or not, but they’re incredible.

Talking Heads – Stop Making Sense. This. Holds. Up. Whether you’re an old fan of this absolutely brilliant band or you’ve barely heard of them, you should listen to this. This is the live album from what is quite possibly the greatest musical performance that ever happened.

Keb’ Mo’ – Oklahoma. Keb’ Mo’ has been around for a long time, though he hasn’t been on my personal radar for almost as long. I discovered this new album recently and was absolutely demolished by how good it is. I suggested it to my dad, and he told me that when I was a kid I apparently accompanied my dad to a local blues festival where Keb’ Mo’ was playing and was enraptured by him. So despite the gap, I guess you could say I’m a life-long fan! (It’s funny how that can happen; children don’t always have the same capacity to “save” things they like in the way adults do. Make a note, parents – if your kid likes something, save it for them!)

Live – Throwing Copper. This album is pretty dark and heavy – “brooding” is probably the term I would use, despite the fact that there’s also a lot of intensity in many of the tracks. While they were never one of the primary flag-bearers of the alternative rock scene of the 90’s, I think they had a really solid entry here and this album is still great 25 years later.

Enjoy, everyone. And as always – tell me what you’re listening to!


What do you do when you can’t stop deliberating?

Most people have been in this situation. You’ve got too many choices. Any of them could be good, but you don’t know which one. You’re going around in circles because you don’t have any new information – nor do you need any. You have every fact you need, you just can’t decide.

How do you get around it?

How do you decide between two job offers? Between three different restaurants for dinner? Between four vacation destinations?

I have a process for you. If you stick to it, these decisions will get a lot easier, regardless of what they are.

Step 1: Eliminate any that are absolute “no” answers. You probably already did this, but I don’t want to assume. Make sure all your choices are things you theoretically would be okay with if they were the only option.

Step 2: Pick one of the options at random to be your “doomsday option.” It’s important you pick at random – names in a hat, or roll dice, or something.

Step 3: Pick a reasonable amount of time to think about the decision. For restaurants, that might be 15 minutes. For job offers, three days. For vacation destinations, 2 weeks. You get it.

Step 4: Say, out loud, “If at the end of [reasonable time frame] I haven’t decided otherwise, we’re going with the doomsday option.” Even if no one is in the room, but especially if someone is.

There. Now you’ve taken the pressure off. The decision is made. You can change it, but if you choose to just not expend the mental energy on the decision-making process, a choice is presented. This will feel fundamentally different than committing to just taking the random option, because the ability to choose isn’t removed from you. You still could exercise your free will and avert the doomsday option, but if you choose to just shrug and say “screw it,” then at least there’s a plan in place.

Most of the time, that’s probably what you’ll do anyway. If you couldn’t decide between options because any of them were fine, then you were wasting juice deliberating anyway. And once you have the option to free yourself, you’ll probably do so unless you have a strong preference – and if you have a strong (but previously hidden) preference, this is a great way to reveal it.

By the way, if the choice you’re having difficulty making is the choice between one “active” option and one “inactive” one – say, the choice between whether you should quit your job or not – make the “doomsday option” the active choice; the one that disrupts the status quo. Say, “If I don’t think of a good reason to stay within 30 days, I’m quitting.” Trust me, your life will be better in the long run.