A few weeks ago, I took my daughter to the Art Institute here in Chicago. She’s three.

So as you can imagine it wasn’t a tremendous success of actually seeing a ton of art. We had a lot of fun though doing crafts they had set up for kids and eating lunch.

My proudest moment was when she yelled out “I really like that picture!” It was Vincent van Gogh’s The Bedroom. It’s my favorite too.

There’s an interesting exercise you can do at the Art Institute or other major art museums. Go find some Picassos and note how old he was when he made them. Now find some Cézannes and do the same.

It’s possible you spot something like Economics Professor at the University of Chicago, David Galenson did.

Picasso’s most valuable work, based on prices paid at auction, peaked when he was 25.

Cézanne at 65.

Some artists peak young. Others get better over time.

Galenson saw this over and over with writers and artists in all sorts of different time periods and industries.

I think the world puts too much focus on the Picassos and the young phenoms. We overlook the Cézannes. The folks who took a while to experiment on getting better and better and who never stopped.

The thing I take from this is that if you find yourself still experimenting in life. If you don’t have it all figured out. If you’re 30, 40, 50, 60 and still don’t know what you want to be when you grow up…

There’s still plenty of room and time to get better. Your peak is still ahead.

P.S. You should follow me on YouTube: where I share more about how we run our business, do product design, market ourselves, and just get through life. And if you need a zero-learning-curve system to track leads and manage follow-ups, try Highrise.

Making It Personal

When I discovered a piece of wood in my food at the hospital. I guess it’s the safest place to be eating wood fragments.

A question I get asked a lot is: “Why do you put so much personal information into the things you write and vlog about?”

I’ll share moments with my crying toddler, or scenes from the hospital with my sick dad. Why don’t I just stick to business?

The reason is the reason I do all of the things I do, the reason I work on Highrise, the reason I started Draft.

I want to build things I want to see in the world.

I look at all these other “business” videos on YouTube, posts on Medium, podcasts, and I see a great deal of people sharing success stories and the tactics they cherry picked which got them there. What I don’t see is them opening up about some of the difficulties of actually running a business. The other difficulties from life and its challenges that stack even further up from there.

You go to conferences and someone up on stage professes, “Hey here’s how I became successful and you can too!”

I’m sick of it. I want to hear from someone who’s in the thick of it. Some days are good. Some are bad. Most have good and bad moments. I want to connect with others who are going through the same things and emotions. To know that what I’m going through isn’t unique.

Everyone tries to put on this fake face while things are chaotic around them. They’re hoping they come out of it with a huge success story they can then start talking about. I don’t want the rosy hindsight. I want all of it.

So I try to share everything. Including the stuff that might not be so positive.

It’s my attempt at creating something that’s just a little different. A little weird. Something that I want to see in the world and hopefully something that people can relate to.

I’m hoping my work can inspire you. I hope I can give you some advice on how to do something better. But even more so, I hope that while you’re doing life, and going through the inevitable problems at work and at home, you know at least here’s someone else going through a lot of the same stuff.

P.S. Thank you so much for the convos over email and the comments in all these channels. It means a lot to me. If I can be helpful with anything please don’t hesitate to reach out ( You should follow me on YouTube: where I share more about how we run our business, do product design, market ourselves, and just get through life. And if you need a zero-learning-curve system to track leads and manage follow-ups, try Highrise.


My 3 year old daughter is in school. Most of her classmates are older than her. She keeps up great. But she reported to us recently, that many kids have called her small. And it makes her feel bad.

It’s easy to just chalk this up to kids being naive. “Hey kid, comparing your age to someone whose older or taller and feeling bad you aren’t as big as them is dumb.”

But adults are just as guilty.

In a study at Harvard, researchers asked participants if they’d rather have $50,000 in a society where everyone else made $25,000. Or $100,000 where everyone else made $200,000. The prices of all material goods were the same in both scenarios. More than half chose the world where they were only making $50,000. Even if they could have more money and wealth in absolute terms, many would rather just make more than their neighbors.

I get it. I look at my career as an entrepreneur and I’d love to be achieving more. I have many colleagues and friends who’ve accomplished quite a bit more so far. And it’s easy to come away from that analysis with emotions probably not that much unlike my daughter.

The best thing for me is to make sure I spend more time comparing myself to myself. Have I grown? Am I better than I was a few year ago? Did I accomplish the things younger me set out to do for myself?

That’s who I need to be bigger than.

P.S. You should follow me on YouTube: where I share more about how we run our business, do product design, market ourselves, and just get through life. And if you need a zero-learning-curve system to track leads and manage follow-ups, try Highrise.


A decade or so ago, a young musician couldn’t get anyone to play his music. He had raw talent, and just recorded his first album, but all the gatekeepers thought he sounded too young. Without Disney or Nickelodeon marketing his stuff, he was a dud.

What does he do?

I bet you know the names of a few famous impressionist painters. Monet. Manet. Degas. What makes them famous though? Are they really the best? Do you know a bad impressionist painter?

What about Gustave Caillebotte?

Caillebotte was an interesting impressionist. I don’t think anyone would say he’s bad, but he sure isn’t as popular as Monet.

Caillebotte also has a quirky story. Upon his death he requested his art collection be hung in the Musée du Luxembourg in Paris. His art collection was about 70 paintings he had collected from his friends, also impressionists.

They weren’t popular. They were actually the worst paintings of his friends. “Worst” being the ones his friends couldn’t get anyone else to buy. And at the time, people didn’t even like impressionism. Many hated it.

So Caillebotte’s request in his will for the government to take his friends paintings and hang them in a museum was insane. How can someone force a museum to hang a bunch of paintings that no one liked or is even familiar with just because it’s a dead person’s request? It resulted in fierce criticism from the art world and public scrutiny.

But Renoir finally convinced the museum to hang half of the collection 3 years after Caillebotte’s death. When the collection opened to the public, the museum was packed. Everyone wanted to see these paintings because they had generated so much scandal.

Today, impressionism is mostly known for the work of the 7 greatest impressionist painters: Manet, Monet, Cézanne, Degas, Renoir, Pissarro, and Sisley.

The 7 friends in Caillebotte’s collection.

Sure Caillebotte had an eye for talent, and a belief impressionism would be admired at some point in the future.

But what really happened is that the inadvertent exposure that Caillebotte brought to his friends also made people like them more.

At least that’s the argument Derek Thompson makes in his book Hit Makers. Derek mentions James Cutting, a professor of psychology at Cornell University, and Cutting’s work to show how exposure begets likability.

In Cutting’s experiments he had people compare famous paintings to more obscure works. Cutting proved the obvious — people prefered paintings from painters who are famous 6 out of 10 times.

But when Cutting came up with an experiment to expose people to those obscure paintings 4 times more frequently than the famous paintings, people’s preferences switched. Now people preferred the more obscure paintings 8 out of 10 times.

We don’t judge things just based on quality. Exposure changes our mind. The more we see, hear, or read something, the more we like it.

That young musician had promise. But he needed to break through somehow. His manager came up with a plan. They were going to get in a van and travel around the country visiting every radio station he could. The kid is charming and has some talent, so it wasn’t as hard to schedule single visits to play an acoustic track from his record live on air.

And this kid performed that track a lot. Eventually the exposure of playing the same song over and over again propelled “One Time” to the top of the charts and this musician is now a household name. This musician’s manager said:

There’s not a DJ that can say they haven’t met Justin Bieber.

There’s a lot to unpack from Justin’s rise to the sensation he is today. Not the least of which was the grit of a 14 year old kid who wouldn’t take no for an answer. Or the unwavering optimism he had of putting himself out there on YouTube uploading crappy videos of himself performing.

But one of the most interesting aspects of Justin’s story is that to get through his obstacle, he went out and generated exposure to his work even if it wasn’t the exposure that he originally intended. He thought he could cut a record and get a ton of people listening to it. Instead he had to take the little wins and build from there.

Most of us aren’t going to be the next Justin Beiber, but it’s still a lesson for us to go figure out how to get more exposure even if it isn’t the big splash we imagine we’re capable of.

Want to be a headline speaker, go do talks at all the tiny chambers of commerce in front of 8 people for awhile. Want to get a byline in a famous publication, do hundreds of guest blog posts for whoever will pick you up.

It’s a big reason I’ve generated the audience I have. I’m out there doing podcasts, daily vlog episodes, interviews, and writing articles in a ton of different places.

Sometimes the opportunity is small. I’ll be the person’s first interview they’ve ever done. Doesn’t matter. Sometimes the message feels repetitive. I’ll be asked about the same question I’ve answered a million times. Doesn’t matter.

I remind myself how often someone like a Justin Bieber played to just a handful of people at first or played the same single song over and over again without losing faith or enthusiasm. Or how Monet, no matter how talented he was, still needed the exposure, even if accidentally, a friend generated.

Because in this day and age, even people with good products, talented musicians or painters, we all need to be out there generating as much exposure as possible to break through the noise.

P.S. You should follow me on YouTube: where I share more about how we run our business, do product design, market ourselves, and just get through life.

And if you need a zero-learning-curve system to track leads and manage follow-ups you should try Highrise.

Worry is the most useless emotion

Five ways I cope with worrying as a leader.

The other week, I interviewed Jason Fried, CEO and co-founder of Basecamp. I asked him what he wish he would’ve learned earlier as a leader.

His response? Worry less.

I smiled when he said this. Oh, how I could relate!

Over the past few years, I’ve noticed how many CEOs (myself included) are stressed out and worried about something. They’re worried about employees leaving, internal team conflict, growing fast enough, their product failing, the market changing, the competition beating them, running out of money, hiring great people…

The list of worries seemingly has no end.

But how do we put an end to it? Personally, I know I’d like to worry less. I think more clearly, act more intentionally, and enjoy life a hell of a lot more when I’m less worried.

In an effort to worry less as a leader, I decided to write out what works for me. Here are five things I try to keep in mind to worry less:

Ask yourself: “What’s the most I can do with what I have right now?”

Most of my worry stems from feeling a lack of control over a situation. I want something to turn out a certain way. So I start to feel overwhelmed and worried when I don’t believe I have the agency to influence that outcome. Here’s the funny thing, though: We have more control than we think. We can control ourselves — our actions, reactions, decisions, and beliefs. What we can’t control are other people and external events. And if that’s the case, well, why bother worrying about them?

Let’s choose to focus on the former: The things we can control.

To do this, a helpful question I like to ask myself is, What’s the most I can do with what I have right now?This question re-focuses my energy on what I am in control of right now. Instead of idling in indecision and mulling over every possible path and course of action, the question “What’s the most I can do with what I have right now?” forces your hand. You must deal with the cards in front of you. And once you do, you’ll clear a path to move forward within the constraints you have. Now you can focus on what you can control.

Remind yourself that the present is real — the future isn’t.

My worry also comes from my mind operating too much in the future. I think, “What if…” or “That could happen…” and brace myself for a future scenario, trying to strategize two steps ahead of it. While in some ways that can be beneficial for thinking through certain complex decisions, it is enormously distracting, for the most-part. The only thing that’s real is what is happening now. The present is real. The future isn’t real yet. It hasn’t happened. Remembering that always lightens the load of my worries.

Realize how good you have it.

When I stop for a minute and look at my life, I realize how goddamn lucky I am. Lucky that I was born in this country, to have the parents that I have, to go to the schools that I did, to meet the people I have across my career… I hope I’m not the only person who feels this way. So many of us, even in our worst, most pained, stressed, and worried work moments, live lives that 99% of the world would trade places with in an instant.

Of course, it’s tough to remember when we fall victim to our own worry-ridden train of thought. To combat this, at the end of every day, I try to think of three specific moments earlier that day when I felt joy or gratitude. (Studies have shown that in fact writing down daily what you’re grateful for significantly reduces stress in people.) I realize that I’ve got it good — and so many of us do.

Share your worries.

Tell other people what your worries are. It does no good to suffer in silence. Often times, when I say my worries aloud to another person, it becomes immediately apparent how stupid that worry is, how pointless it is… and the worry evaporates. If it doesn’t, at the very least, you now have a confidant, a pal, who you can think things through with and discuss a plan of action around. Don’t keep worries to yourself. Share ‘em.

Step away, move your body, get some sleep.

My worries become exacerbated when I don’t take care of my mind and my body. When I’m in a particularly stressful or worrisome situation, usually the best thing is to take a step back, get my body moving, and go do something different. Go for a walk. Get on a bike. Breathe some fresh air. Go surround yourself with greenery, or good music. Talk to a sibling, parent, friend, boyfriend, or spouse about something completely non-work related. And get some sleep. Rest the mind, rest the body. The break is needed. I always return feeling clearer and fresher on what matters.

I hope these tactics may be as helpful to you as they’ve been for me.

If anything, as I shared with Jason during our interview, do keep in mind what a friend once told me:

“Worry is the most useless emotion.”

Enjoy this piece? Read more of Claire‘s writing on leadership on the Know Your Team blog. And, check out Know Your Team – software that helps you become a better manager.

The Boss You Don’t Want to Be

Here’s the one thing that separates good managers from the bad.

Most of us have had two different types of bosses during our careers: The Boss Everyone Wish They Had and The Boss You Don’t Want to Be.

Recently, I was reminded of the latter — The Boss You Don’t Want to Be — when talking to two friends the other week.

Both of my friends are employees. One works at a large, growing healthcare tech company, and the other at a notable, high-profile nonprofit.

Both have managers who they cannot stand. Both of their managers have absolutely no idea.

One friend told me: “Three out of six people on the team have already quit, and two others are on the verge of quitting… And he has no idea.”

The other friend told me: “We keep losing talented people all the time because of him… And he has no idea.”

Both of their managers are good, well-intentioned people. In fact, they’re popular with their respective CEO and Executive Director. They were placed in their management positions because they were strong individual contributors and high performers.

But as managers? They are literally driving their own employees away. They’ve become The Boss You Don’t Want to Be.

What’s going on?

In listening to my friends, I realized their managers have one thing in common:

These Bosses You Don’t Want to Be habitually put their own self-interest ahead of their team’s best interest.

They cover their ass to look good to upper management, even if it comes at the expense of supporting their team.

They don’t want to know the truth of how their employees feel because they’re scared of what they might hear, and how it would personally feel to hear those things.

They feel entitled to more privileges, leeway, and benefits because they feel they’ve worked harder than anyone else on their team.

Sound familiar? Perhaps you yourself have worked with The Boss You Don’t Want to Be, who exhibited some of these beliefs. But don’t be so quick to judge: These people are not evil nor maniacal.

Truth be told, the mindset of The Boss You Don’t Want to Be is easy to succumb to yourself if you’re not paying close attention.

Consider these situations:

Someone on your team isn’t pulling their weight and you have to pick up the slack… You’re frustrated.

Someone on your team didn’t execute up to right quality standards… You feel like you can’t trust anyone to get the job done well.

Someone on your team isn’t producing the right outcomes… You’re worried how that’s going to make you look.

Someone on your team is pressing your buttons (and honestly being a pain-in-the-ass)… You feel low on patience when talking to them.

Whether you become The Boss You Don’t Want to Be or The Boss Everyone Wish They Had comes down to how you react to these situations.

You have two options:

You can decide the situation is hopeless — you’ve done all you can. Everyone has pretty much proven they’re incompetent. You choose to focus on yourself and move your own career forward. You put your own self-interest before the team’s.

Or, faced with the same situation — you can decide to look inward. You see your team’s shortcomings as a reflection of your own leadership shortcomings. You ask yourself, “What can I be doing to create a better environment for our team to be successful?”

Surely, taking responsibility for your team’s hardships and treating them as your own means more time, effort, and energy on your part. But that’s what the best leaders do: They do the hard thing because it’s the right thing. They put their team’s best interest before their own, instead of the other way around.

This is what separates The Boss You Don’t Want to Be from The Boss Everyone Wish They Had.

Which are you?

Enjoy this piece? Read more of Claire‘s writing on leadership on the Know Your Team blog. And, check out Know Your Team – software that helps you become a better manager.

The importance of sucking

Lessons from a bruised leg…

My leg looked liked this a few months ago:


No, I didn’t get surgery. No, I was not mauled by a bear.

I went snowboarding for the very first time over New Year’s.

The experience was brutal, needless to say. I fell probably a hundred times. Over and over and over. For those of you who’ve learned to snowboard before, you know what I’m talking about 🙂

Surprisingly, the most painful part of the experience was not the physical aching of my knees or my wrists or my butt.

Rather, the greatest pain I felt was a sinking sensation I had in the pit of my stomach: I was really bad at snowboarding. I wasn’t picking it up “as fast as I thought I was supposed to.” I was frustrated and embarrassed.

I recall thinking to myself, “Maybe snowboarding just isn’t meant for me…

Then, I tried to remember the last time I felt this way. When was the last time I was this bad at something?

I couldn’t remember. I couldn’t remember the last time I was this outside my comfort zone. I hadn’t dared to suck at something — to allow myself to be vulnerable, to look a little “dumb” to my friends — in a very, very long time.

As adults, we gravitate toward the things that we initially have the least resistance to. The new hobbies I’ve tried to pick up as an adult — whether it’s screen printing or yin yoga — are all things I’ve already had a predisposition for. I’ve already been painting and doing yoga for quite a while. It wasn’t a stretch to try those new mediums and related activities.

But with snowboarding, I was in foreign territory. I wasn’t predisposed to snowboarding. And I’d forgotten the importance of doing the things you’re not predisposed to.

When you let yourself be bad at something, you regain your humility. Sucking at something humbles you. As adults, we protect our egos by not allowing ourselves to be bad at things.

You also remember what the point of learning is: to learn. When you learn, you mess around and you mess up. You’re not supposed to be proficient from the get-go.

And, you rediscover that persistence leads to progress. Day 3 of snowboarding was 10X better than Day 1. I got better. In fact, I got back from my second snowboarding trip just yesterday… and I did a few runs without falling once!

I couldn’t be more grateful that I was so bad at snowboarding. It was the reminder I needed to push myself outside my comfort zone more often. To fight the instinct to expect excellence when I learn something new.

Now, I want to seek out more things I’ll suck at.

How about you?

Enjoy this piece? Read more of Claire‘s writing on leadership on the Know Your Team blog. And, check out Know Your Team – software that helps you become a better manager.

Let me remind me

Truly learning a lesson is deeper than simply knowing the lesson. It’s possible to know a whole lot more than you’re capable of acting on with regularity. And it’s the act, not the mere knowing, that makes the difference.

When it comes to physical lessons, we instinctually know this. I know the steps it takes to do a kickflip ollie on a skateboard, but I still haven’t practiced nearly enough to pull it off. I wouldn’t expect to be able to do this without spending hours and hours of repetition.

But when it comes to mental lessons, it seems like most of us don’t respect the need to practice. I wrote about how this applies to learning something like programming to the level of mastery a few days ago. But it applies to life and business lessons as well.

Take the simple example of “I shouldn’t infer intention from action”. I know and believe this, but I still fail to practice it frequently.

Let’s say someone criticizes my work. I might infer that they’re just doing this to needle me needlessly because I criticized their work a few weeks back. That this really isn’t about the work, but it’s about retribution for an earlier skirmish.

That might be true. It is one of the possibilities. But it’s probably not that likely. It’s probably more likely that there’s simply a mistake in my work and the person spotted it. Unrelated to whatever discussion we had about their work weeks back.

But we humans love to jump to conclusions and validate our insecurities. That’s why we need lessons and coping mechanisms to do better. And that’s why it’s not just enough to know them, but to practice and be reminded all the time.

A strategy I’ve successfully used to remind myself in moments of need is to look for emotional smoke. If I’m getting upset about someone pointing out an error in my work, and it’s not because they’re being a dick about it, then that’s smoke. If you tune your emotional smoke detector to go off when your mood changes or your temperament flares, you give yourself a pause to contemplate which lesson you should be practicing.

The instinctual autopilot is great when the sky is blue and there’s no turbulence, but as soon as the clouds gather and the ride gets rocky, it’s time to grab the wheel with intent. So that’s what I try to do. Be mindful of emotional disturbances, hit pause when I spot them, and go through my current curriculum to find the lesson that clearly still needs attention.

The most important lessons are so because they’re hard. They’re the ones that take the most work to internalize, lest we forget in the moment and take action without their input. They are the ones we need to hear over and over again.

Pause yourself. Remind yourself. Repeat yourself.

Watch out for “everyone” or “no one”

Years ago I was in a meeting when this one person broke into the conversation and declared “Don’t say everyone or no one. It doesn’t mean anything.” It’s obviously a great point — one that’s easy to forget.

We all do this. We try to justify our position by saying “No one knows…” or “Everyone knows…” or some derivative thereof. When you throw around these extremes you weaken your point. There is no such thing as everyone or no one. Don’t justify your position by putting an unjustifiable abstraction at the core.

Even “Most people” is a bad one. “Many people” isn’t as bad, but it’s still loaded. I find myself saying it all the time. “Some people” is better. A clear “these people” is best.

So when you’re making a point or taking a position, watch out everyone or no one — they aren’t really there.

Getting less done

So you got a lot done this week? Good for you. But what exactly did you get done? Was it work you’ll remember next month? Was it work that’ll matter next year? Did you learn anything that’ll help you tomorrow?

High productivity doesn’t mean squat if the things you’re getting done aren’t truly important. It’s far better to get a few top things done, and done well, than to crush a mile-deep todo list of trivial bullshit.

But it can be hard to tell the difference when we constantly celebrate things like inbox zero. What about all the things that didn’t have an email or explicit todo attached? It’s easy to fool yourself into thinking you’re on top of it all when all the app counts say zero.

Occasionally you need to waste time for a while to be able to spend it better later. If you’re constantly busy, busy, busy, you don’t have any headspace to reflect on where every daily step is ultimately leading you. Running real fast is no good if it’s into a brick wall.

You need to carve out more unproductive time. Get less done for a while. You’ll probably realize that a bunch of the shit that zaps your attention and time needn’t be done at all. Just let it slide and see that it probably just didn’t matter. Very few things ultimately do.

Productivity is all about focus, which in turn is all about a narrowing field of view. Shutting out the rest of the world. But many novel solutions require just the opposite: An expansive field of view, letting in the rest of the world.

Look, you obviously can’t have your head in the clouds all year long. But for highly motivated people that doesn’t seem to be a danger as much as having your head in the grind 24/7.