The communication habit you’re missing

Saying hard things to people that matter

Once upon a time Seneca said:

We suffer more in imagination than reality.’ — Seneca

He’s dead on. Especially when it comes to having hard conversations with people that matter in life.

Many people would rather consume themselves with fear than have a hard conversation. Super sensible right?

But why are we so fearful of bringing up tough topics?

It’s because Mr. Tribal Brain is kicking in. He does not want you to stand out as a disagreeable member of your community. That is tantamount to suicide if living with 20 other people in an isolated village 8,000 years ago.

But today that’s no longer a useful biological impulse. Overcoming this evolutionary handicap will make your life better. You’ll be able to say things like:

‘I didn’t like the way you just looked at me, it made me uncomfortable.’

‘I find it hard to justify continuing to invest in our friendship after what has happened.’

‘When you walk out the door without saying ‘bye’ it makes me feel unappreciated and small.’

Those things should be as easy to say as:

‘Bro, wanna go see Wonder Woman’?

‘Can you pass the Sriracha?’

‘Vampire Weekend made me a Horchata lover.’

This post is your first step in getting there. It is going to give you two useful strategies along with three action items to start initiating hard conversations.

Strategy 1: Filter irrational people from your life.

Hard conversations are useless if you’re having them with irrational people who don’t listen. If your conversational counterpoint possesses these traits they will not:

  • Hear or accept your feedback
  • Make any changes as a result of your feedback

Trying to use hard conversations to improve relationships with irrational people is not a good use of time. The better approach is to just filter those people out of your life altogether. They aren’t worth it.

This process of filtering will be easy if you perfect strategy 2.

Strategy 2: Mint a hard conversation habit

Everyone feels the same thing when they aren’t saying what they wish they could. I’d characterize it as the feeling of dissonance.

It’s what wells up in your nerves after you hold feelings inside and don’t let them out.

For me it feels like what my body does while sitting in a dentist chair. I try to stay relaxed while they are pricking away at my ill-flossed gums. But still, I’ll find my legs and toes tensing up constantly. I’ll try to focus on releasing that tension but once I go back to thinking about something else it returns.

The feeling that a hard conversation should happen can feel the same. In those moments we have a choice — to suppress (and thus keep suffering inside our imagination) or say what we need to say (improve our reality).

In order to say more than you suppress you need to learn how to use the dissonance feeling as a trigger for habitual action.

In the short term you’ll need to put on your willpower pants to get this done.

That’s because willpower is the activation energy needed to perform a non-habitual action. But while some amount of willpower is needed you can minimize the amount required by planting cues into your environment that remind your experiencing self what your narrator self wants to do.

An easy way to do that is to create a recurring reminder in an app you see daily that says:

‘Say what I’m feeling the moment I feel it today.’

You’ll whiff a lot at first, but once and a while you’ll be able to pass instructions to your experiencing self to actually say the hard thing in the moment it should be said.

If you’ve followed Strategy 1 and surrounded yourself with rational people you will gain great results.

These results will create a positive feedback loop encouraging you to saymore often. Continued positive experiences with this will change the say / suppress probability curve in a compounding fashion.

With each instance you’ll need less willpower to choose to say. Eventually willpower will be unnecessary and the habit will calcify.

Years later you will find yourself tranquilly sitting on your porch sipping horchata.

Suddenly you will be struck with the memory that you used to totally suck at hard conversations. You’ll be stunned that you blunderbussed your way through life for so long without this skill.

Do these things right now

Instead of clicking on the next tab in your Chrome Centipede, make the last few minutes of reading this stupid article worth it by doing three things:

  1. Make that recurring daily reminder in your app of choice encouraging you to say hard things.
  2. Save this article somewhere and reread it in a week to reinforce the concepts.
  3. Fill out this self-quiz I made based of the ideas in the book Crucial Conversations. It’s a great place to start if you don’t know how to find the right words to start a hard conversation.

Good luck — this stuff is not hard. You just have to actually apply the idea in your life to experience any benefits.


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Dear Noise

Leave me the hell alone please.

You’re the buzz in my pocket. You’re the errant LinkedIn request. You’re the little red push notification. You’re the embodied entirety of Twitter. You’re the thing that breaks my flowstate. The blimp on the map that throws me off the journey.

I hate what you are. Worse, I hate what you’ve made me become. I can’t resist you. I’ve allowed you into my life for so long that my brain is wired to crave you. You’ve physically altered me, one *BZZZZZ* at a time. You are a cute little attention tapeworm that is killing me slowly. You divert my attention away from what I want to be doing and shove my face into an ever-updated shiny object of perpetual distraction.

Noise — I recognize deep down that it is not your fault. You are just following orders. You do indeed have a designer, a God of Noise that has brought you into this world. That God is an SF-based product manager with a flannel mustache and one sole mission: to pluck out my eyeballs and trap them in a fancy mason jar on his Herman Miller desk. Your designer does not want my life to be good. He wants to sharecrop my attention, and he is going to use every magic trick he has to ensure he gets it.

For years I didn’t realize you were such a problem. I thought you were helping me connect and engage in the world in an all new way. But now I know that you are a big black spot that’s holding me back from really living.

Right now, the average time to distraction across our population is seven minutes. And we as humans have you, The Noise, to blame. You bring out the worst in us, you make us weak, unfocused, and trivial. Did you know that it takes us about 15 minutes of deep thought before we can really immerse ourselves into a problem? How do you expect us to create anything great if you break our concentration every seven minutes?

Dear Noise — you’re existence essentially ensures that most humans will never produce a real breakthrough or insight of any substance. You are relegating the burden of human progress to the outskirts of society. To the weirdos who don’t carry smartphones, who reject social networks, and who escape you at every possible turn.

For the last six months I’ve done my best to join the ranks of these ostracized psychopaths. I’ve deleted Facebook & Instagram, blocked out ads and feeds, and turned off push notifications. I’ve done my best to bury you. But still I cannot consistently outrun you. Noise, you continue to insidiously penetrate my existence. The Signal of what I want to do in life is often invisible against the background radiation of your insipid social graph.

But Noise — let me be loud and clear. I will break out of your cage. I’m at war with you, and plan to either win or die. My attention and my time are all that I have, you are not permitted to leech my most precious resources from me forever.

Noise, consider yourself on notice. And if your designer happens to find this letter, I have a final word of advice for him as well:

Dear designer of attention based systems, you have a choice. On one hand, you can keep vampirically draining humanity’s willpower under the guise of capitalism. Or, you could use your unique talents to vaporize this vast fog of Noise that clogs the arteries of the human superorganism. You could design systems that maximize focus, prolong linear thought, and make us more capable of dedicating attention to hard problems. Heck, maybe you could even….

….sorry, just read the most hilarious Buzzfeed article. What was I saying?


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Jump off the problem solving treadmill

The life of a startup founder is unglamorous.

My day is mostly filled with the fixing of issues. Cool stuff like discussing strategy, closing major deals, & designing products are a pretty low percentage of actual time expended.

Issues that fill days include:

  • Tracking down pieces of paper the government requires of me
  • Getting customers to actually pay invoices
  • Taking out trash cans and cleaning dishes at office
  • Editing documents and emails for typos
  • Negotiating with vendors
  • Polishing minor product minutia
  • ‘Setting up a time to connect on a call next week…’

You get the idea.

It’s not always fun, but these are the basics needed to create anything real in the physical universe.

Sure when your company grows up you’ll have other people to do a lot of the little stuff. But when you’re small everyone chips in on whatever is needed.

This issue solving treadmill is especially pervasive for people managers. As a manager one of your most important functions is to solve issues standing in the way of others. I envision this process a bit like being one of those sweepers in curling.

You’re out in front making it easier for your people to do great work

You want to evaporate the nonsense in the way of your colleagues so they can be maximally effective. This often means you’re running on many problem solving treadmills in parallel as a founder.

But issue fixing is not even just for managers. Everyone and everything in a company is built around solving issues.

You’re fixing issues for your team. Your team is solving issues with your product. Your product is solving issues for customers. If you’re B2B your customers are solving issues for their customers…

But here’s the thing:

Life is just not an endless problem solving treadmill.

News flash: there are worthwhile things in life outside of work (even passionate work). Spending time with good people, experiencing culture, and expressing new forms of creativity all come to mind.

In fact the whole point of most products is to make those other things easier to do or at least to free up time in other areas so those things can be done more often.

So the time you invest in work carries very high opportunity costs.

Thus, you better be solving issues for a meaningful purpose. I’m fortunate to have found what that means for me.

The subtle practicality of purpose

Beyond the squishy philosophy of purpose there is a simple practical reason to have one for your team.

It is really damn hard to get people excited about boring things.

Anything important is going to be rife with issues that need solving. Especially if that thing is new. To solve issues you need problem solvers. Just like you, the time they spend with you comes at high opportunity cost.

If the vision you have for them is not exciting, it is not particularly logical for them to cancel weekend plans and work longer hours to stay on the issue solving treadmill.

I turned 25 today.

Birthdays are reminders of how precious time is. This one in particular is a bit frightening because I find it absurd 2007 was actually ten years ago.

Obviously we all just slipped into a wormhole right after Graduationdropped. Or ok fine, maybe I’m just getting a bit older like everyone else.

Either way, I’m not spending the next 25 years solving issues for the sake of solving issues.

I’m learning that harmony between passionate work, enriching experiences, and time with good people is a beautiful life. A much better reality than living exclusively on the issue solving treadmill.

The ask here for you is a simple one: look up from time to time my fellow problem solver. Ask yourself why you are on that treadmill today.

It could be time to hop off for a while and find tranquility and meaning elsewhere.


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You ≠ Your Startup

This is the type of post I wish someone shared with me two years ago.


In corporate America I was a number. Make no mistake — you are too.

The truth of corporate life is that your worth to the company is 100% tied to your usefulness. Somewhere a manager has you as an expense in an excel spreadsheet. If you can’t be justified you can’t be kept, no matter how clever your water-cooler humor may be.

Corporations are the destinations degrees are designed for. In academia though your still a number — you’re tuition with legs while walking to the dining hall or lounging on the quad.

This is not a moral claim against these organizations. Still though, it makes sense that young people view startups as alluring escapes from feeling like a mere bead in an abacus.

We assume that the grass (and money) is plenty greener on the startup side of the fence.

As a founder of a startup you’re clearly no longer a number — you’ll be a person with a company! Your email signature will likely command respect. People will naturally invite you to speak at gatherings. You will be fawned over in the media. Investors will shower you with money because you ‘understand millennials’.

Everyone will reinforce the notion that you’re on an incredibly majestic Hero’s Journey into Unicorndom.

This will certainly feel better than being a number in an org chart, right?

Welcome to the Echochamber

For most first-time founders the transition transpires differently. Instead of working for themselves and building something meaningful, they end up working for the Echochamer.

The Echochamber is the collection of investors and accelerators who demand that you eat, sleep, and breathe your company at the expense of life.

It’s the startup press who will fudge realism for page views.

It’s the service provider emailing you after reading an article about your last fundraise.

It’s the ‘mentor’ who siphons equity and ego fixes for warm intros to nowhere.

The Echochamer takes down the clocks and strings up flashing lights on the walls of the startup casino. It will keep you attending events, reading its articles, taking coffee meetings, and shelling out cash4coworking.

You’ll keep doing it though because your life does not matter until you’re finally running an (unprofitable) unicorn.

The lesson for you is to not give in to the frothy hype of the Echochamber. Open your eyes to the implicitly self-interested relationships you will engage in while making a startup. Take advantage of opportunities that will benefit you but don’t let them take advantage of you.

If you give into the flashing lights you’ll find yourself gambling away your twenties building a startup that should have been a tweet.

And sure this is easy enough advice to give, but you won’t implement it unless you solidify one critical mindset change.

You are not your startup

The Echochamer is designed to reinforce the notion that your self-worth is tightly coupled with how well your startup is doing on that particular day.

This is how it keeps existing. The first step in avoiding the Siren calls of the Echochamer is to sever any relationship between your self-worth and the financial outcomes of your startup.

That’s the lynchpin upon which mentally healthy founders can build lasting and powerful companies without suffering through self-imposed sabotages.

A failure to decouple the two will shred your P&L as swiftly as it lays waste to your mental health. You’ll be too defensive and retaliatory to agnostically look at what is working and what is not in your business in order to make it better. You won’t put your work in positions where it will be judged by critics. You’ll exist in an endless stealth mode. You’ll always be ‘crushing it’ until the day you’re not.

Soon after everyone stops inviting you to events and tweetstorming about your now broken company you’ll be left with nothing but a ragged mental landscape and some worthless common stock to show for it all.

My wish for the young & naive founder is simple: decouple your self-worth from the success (or failure) of your startup. Both your work and health will be better off as a result of the schism.

Most startups should be tweets

As a creator, you should always aim to nudge the ideas you feel are valuable to others out into the world. This is the art of idea deployment. To do this well, you as the creator have to think carefully about which reality deployment channel your idea best fits into.

Would it be best presented as a scientific paper? A painting? A blog? A conversation? Perhaps the idea should manifest as a physical object. Maybe a diagram, or just a post on social media.

On very rare occasions, it may become apparent that the idea you’ve discovered can only be brought to life if a lot of smart people work really really hard on it for several years. This idea can’t be made truly real in a blog post alone.

That’s when you have to create an organization of people that also want this particular idea to exist in reality. That is when you create a startup. That’s the ONLY time you create a startup.

But right now, deep in the echo-chamber of startup-y madness land, a frightening thing is happening that’s worth calling attention to. Simply put, people are wasting their lives working on ‘startups’ that are better off as mere tweetsThey are all choosing the wrong channel to deploy their ideas.

Each top ten startup city is filling up with founder-clones building the next B2B VR drone AI bitcoin disruptor. They’re doing it because having a startup is great for their personal brand. Or because they see it as a way to earn fame. Even more likely, they don’t know why they’re doing it. They’re ‘why-less.’

Beyond the redundancy of ideas in the echo-chamber, most new ideas are incredibly thin. While it’s extremely helpful to be able to communicate a complex roadmap in a blog post, don’t mistake a trite blogpost for the roadmap itself. Startup ideas must go deep, down to core human drivers and raw economic arguments. They must stand up to ruthlessly candid feedback. They must include a non-BS reason that you’re one of the few people in the world that should be working on that problem.

A competitive advantage is not a clever sentence you toss in a slide deck the night before a pitch. A competitive advantage is a unique worldview only attainable through the past experiences you’ve had. A startup worthy of all your time and attention should be the crescendo of long bubbling social observation and excruciating self-awareness. The nature of a startup is hardcoded into it by the natural inclinations of the founder.

The requisite nuance and insight that produces great startups can’t fit in a tweet. You can certainly tell us what you’re working on in 140 characters, but that should be merely the first layer of a deep dive down into the deltas you see between actual reality and the way you want it to work.

So the next time you read a TechCrunch article and are met with a burst of inspiration to move to SF and reinvent the way the on-demand Pastrami economy operates, ask yourself if it’s really worth nuking 10 years of life in service of the idea. It may be wiser to pop off a quick tweet about the idea to let it get out of your system. The opportunity cost of spending time on things you don’t care about is far too high.


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Why Puzzles Are Awesome

I’m home for Thanksgiving for a few days, and I’ve rekindled a love for a hobby long forgotten: puzzles.

Puzzles are totally awesome, plain and simple. Aside from being a fun activity to do with friends, puzzles possess other benefits which I shall relay to you now.

Why puzzles are totally awesome:

You’re investing in an experience

First off, when you choose to purchase a puzzle, you’re not paying for a product. You’re paying for the experience of assembling the puzzle. Once you open that box and spew those jagged cardboard squares onto a table in your house, the experience has begun. And while the rest of your life is run by your calendar, puzzle time does not need to be scheduled. It’s a low pressure, but mentally engaging experience.

When you’re sitting at the puzzle table immersed in puzzle land, you’re simultaneously writing a little story. Once the puzzle is done, you’ll look at it and remember that quiet satisfaction of placing the final piece. Or that pesky edge hunk that was stuck in the couch for three days. And how could you forget the time when Grandma slammed down three pieces right in a row like some sort of magical-elderly-puzzle-robot-master. BAM BAM BAM. Nanny owned those wispy clouds. In her post-puzzle interview she noted that the touch of mountain on the edge of the pieces were the key to her speed.

It really does not even matter what the puzzle depicts. A completed puzzle is a reminder that you are the type of person that do what is necessary to solve the problems you face.

Why puzzles are totally awesome:

They remind you to have faith in humanity

The Achilles heel of any puzzle is lack of sufficient resource substitutes. Unlike quilt making, you can’t mix and match puzzle pieces from multiple sets. If you’re missing a piece, you’re puzzle is forever incomplete. An eternally hollow flatlander with a hole in it’s heart.

So inevitably, there will come a time during the solving of a puzzle when frustration turns into outright blame.

‘Well, this damn piece must be missing!’

We don’t want to admit that we’re not skilled enough to find a particular piece, so we slam the competence of the puzzle manufacturer’s Q / A department in a flurry of frustration.

But as I told my family (my fellow puzzle collaborators) over this holiday: “the first rule of puzzles is to have faith in the puzzle makers.” The moment you begin to doubt that the pile of pieces before you in fact does contain the resources you need to accomplish your goal, a host of psychological handicaps start slowing you down. You start to ignore certain areas of the puzzle. You do silly things like waste an hour counting all the pieces. Worst of all, you start complaining and the experience is no longer fun. You have to push away the urge to blame, and instead must have faith that all the pieces are there. I think this reminds us to have faith in the workmanship of others. People can deliver, so have faith that the puzzle makers have.

Why puzzles are totally awesome:

They build self-efficacy!

Self-efficacy is in my opinion the most important cognitive trait to cultivate. It’s your belief in your own ability execute the behaviors needed to attain a particular outcome. High self-efficacy is a building block of a fulfilling life. It affects how much energy you expend pursuing goals, how many times you try and fail, and how likely you are to become a master of any particular skill. According to the guy that researched and coined the term, self-efficacy is built through:

  • Mastery of experiences: performing a task successfully and solving problems in the process.
  • Social modeling: seeing peers overcome similar obstacles to the ones you face.
  • Social persuasion: positive feedback and encouragement from others.
  • Reframing stress: solving problems trains our brains to use stress as a source of motivation instead of paralysis.

Sounds like puzzle building to me. Sure, in the grand scheme of things a puzzle is a pretty trivial challenge. Notwithstanding, solving a puzzle requires a certain level of focus, diligence, and skill. Solving one is a small reminder that you are the type of person that can go into challenging situations and consistently do what is necessary to solve the problems you face.

Why puzzles are totally awesome:

They bring people together to solve problems

You can solve puzzles with as many or as few people as you like. When you involve others in the process of making a puzzle, you are creating a shared memory of addressing a challenge together. Put another way, you get to share the IKEA effect with other people.

That is the type of memory that strengthens a relationship, and potentially could even repair a broken one.


So as we move our way though another holiday season, go ahead and work a puzzle into the activity rotation. Set up a dedicated table in an open space and encourage guests to sit down and help those little craggy picture shards find where they belong.

(thanks Mom!)