The search vs the grind

“If I had an hour to solve a problem and my life depended on it, I would use the first 55 minutes determining the proper questions to ask, and 5 minutes thinking about solutions.”

Albert Einstein

We love being productive because productivity is a drug. Our neurochemistry gets juiced with dopamine or seratonin every time we check that box.

We do the same thing at scale — at the end of the day we measure our contribution based on the volume of boxes we checked. Sometimes as leaders we measure this based on the boxes our team checked, but even though the scope is distinct the unit of measurement is the same. We naturally place premier value on output, because our brains are wired that way.

This isn’t wrong, it’s just incomplete.

Diligently executing our plans is an important part in running our businesses, or our careers, or our lives. That steady pace of production is the engine that steadily moves us forward. We need to grind to get anywhere, and so it’s useful that nature gives us happy drugs for doing this hard work.

But we tend to level up, as individuals and businesses, in an entirely different way. We make steady progress by checking boxes, but when people or businesses take huge leaps forward it’s more often due to a change in our internal operating system (a new skill, a new direction, a new connection) which only comes when something new is introduced.

Searching for these revolutionary new elements is therefore important work, but it runs counter to our nature. The problem, as anyone who has lost their car keys will attest, is that whatever you’re searching for is always in the last place you look. So until you find what you (often didn’t know you) were looking for, this type of searching work does not give us any of the happy neurochemical feedback that we get from staying the course and producing.

We’re chemically wired to stay busy, even if we’re solving the wrong problem.

Think about how abnormal it is to read a book about your field or discipline in the workplace. Books are someone’s considered attempt to provide the most valuable information possible in the best package possible, and so are one of the highest-probability searches one can undertake. But we too often see reading as much less valuable than executing the next task.

Success, whether personally or in business, is necessarily built on a combination of producing (steady box checking against the work that we know needs doing) and searching (constant exposure to potential improvements to our internal operating system, even if no such improvements are guaranteed). Both sides of the coin are necessary if we’re to reach our potential.

Given that, it’s worth remembering that production places our brains under the influence of drugs, begetting a need for more production, and if we don’t make it a point to invest in the search we risk drastically limiting our ability to revolutionize our companies or ourselves.

How to build a sandcastle (or anything)


I woke up slowly to the sun shining through the sheets, and pulled my blanket up over my face to bring back the darkness. I was settling back into my dream when I remembered. I jolted awake.

The sandcastle.

My dad and I spent all day building it, while my mom sat on the beach reading her book. My dad said the trick was to start by making the sand wet so it was strong. We filled my blue bucket with water and sloshed it over the sand, making a wet spot partway up the beach. Then we went back to the water and filled the bucket with wet sand. We packed it down tight and brought it back up to the wet spot, and when we flipped the bucket over on its head the sand that came out was shaped like a castle. But you had to lift it up so quietly. Otherwise the sand falls apart and you have to do it again.

We made four castles like this, and then my dad showed me how to make the walls connecting the castles. We smooshed sand into tall walls, and then we carved windows in them so the sand soldiers could shoot arrows at the bad guys. We had to make sure that the walls were flat on the top, too, so the people could walk across them without falling down. I did a wall all by myself, but it wasn’t as flat as the other ones.

Then we did a trick. We took wet sand in our hands from the water and ran so fast back to the castle and dribbled the sand in our fists and made spikes on the top of the castle. Every spike we did special like this. These were for protection. We made little windows in the spikes too with a stick, just like the castle in the beginning of movies. This way the townspeople could see out.

My dad never made a sandcastle with me before. It was perfect.

I threw on my clothes from the floor, dirty from last night but that’s ok, and ran downstairs. My dad was eating breakfast. He was usually gone when I woke up, but at our vacation house he didn’t have to go to work so he was there and he smiled when I came down. I told him I wanted to see the sandcastle we made, and he said he’d come with me down to the beach. We ran down the stairs and took off our shoes and ran onto the sand. My dad couldn’t keep up with me because I’m so fast.

But it was gone. Our sandcastle was gone, and the sand was wet everywhere around where it was, not just in the one spot. I cried and cried, and my dad hugged me. I hated the sandcastle. It was perfect, but it was gone.


I thought of that day so long ago with my dad, when I built a sandcastle with my son at the beach in Northport last summer. We wetted the sand and used a bucket that looked almost like the one I remember to create the turrets. We crafted the walls just so, and added the spikes that were my favorite part when I was young. My son lit up when he saw how the dripping sand stalagmited into spikes on the corners of the castle. That was the best part. Well, that and when I showed him how to draw the windows. I told him we had to make it just perfect, so the townspeople could live there. He found two pinecones and put them inside the castle, and said they were the mayors. He was so proud. It was perfect.

I told him it wouldn’t last, that it would be gone by tomorrow, but even though he acted like he understood then, it still hit him hard when the tide came in and washed everything away. He said he hated it, and he wished we had never made it. He cried so hard, I almost wished we didn’t make the sandcastle. Well, maybe not, but at least I understood.

I’m so glad we made the sandcastle, but I’ve stopped caring about sandcastles long ago. I’m so glad because I got to spend time with my son, and see the gleam in his eye when we dribbled those spikes for the first time. I can still see it now.

It’s gone, but it was perfect.

The (not so) new leadership: Context > Control

Many leaders still see their job as directing the activity of the people working for them, setting up detailed systems designed to remove the variability from human behavior and achieve predictable outcomes.

This approach to management stems all the way back to 1911, when Frederick Winslow Taylor released his opus, Principles of Scientific Management. His techniques were responsible for dramatically increasing the output of industrial era factories by limiting the freedom of employees to make decisions, instead creating detailed scripts to drive very specific, management-prescribed, behaviors. By creating a system that forced every employee to conform to standards in every situation, Taylor ensured maximum compliance, which at that time equaled productivity.

But that was a different time, and those employees were doing repetitive tasks in a factory. Today’s workers are asked to navigate rapidly changing markets and produce results in all kinds of situations, so compliance, at best, comes with many caveats. But many managers still use those techniques today. You see the issue.

Today, the most successful companies adopt a context > control philosophy to management. At VNN, it looks something like this:

  • Leadership’s job is to create context
    • Establish long-term vision, short term milestones needed to move toward that vision, and set any hard guidelines outside of which employees may not go (the goal is to make these as broad as possible)
    • From there, avoid making decisions wherever possible
    • Instead, ensure that everyone within the organization has the appropriate context to make their own decisions. Ensure everyone is aligned to where the organization is going, and understands their role in achieving the vision.
    • Then align some more (HT Patrick Lencioni).
  • Individual employees’ job is to use good judgement
    • Each employee is empowered to make the best decision for every situation in which they find themselves, based on the context provided by leadership

This way, the people closest to the situation, the ones best equipped with the most information about the situation–namely the employees–are the ones making most of the decisions. Meanwhile, leadership spends most of their time answering questions, providing feedback, coaching, training and generally ensuring that the decision makers (employees) have the context needed to make decisions in the moment that are aligned with overall company priorities.

Doing this admittedly requires humility on behalf of the leadership, as they need to embrace the fact that they cannot keep up with the pace of business on their own, and empower their team to help them make critical decisions (and then support them when they decide things different than you would). But I’ve found that if you empower your team, and expect them to step up, they do.

When they do, the rewards are many. In addition to better serving customers (by ensuring the person they’re talking to is empowered to help them without checking with their boss), this approach has proven to lead to a more engaged and productive employee base, and a greater level of innovation throughout the organization.

I remember the moment when I realized we had implemented this effectively at VNN: I had given feedback to an employee that I didn’t think a project he was passionate about would work, but I also let him know that, as always, my opinion was context and it was his decision, within the parameters we had constructed. He decided to go forward with it, busted his ass on the project around his core responsibilities, and it’s now one of our most successful business lines. I had to eat some humble pie on that one, but there’s no question that VNN would be less successful if I had dictated that particular decision.

What was a radical philosophy as recently as a few years ago, what I’ll call “context > control,” is quickly becoming mainstream. It’s not there yet, but organizations like The Ready, Whole Foods and Google are all leading the way, and VNN is working every day to do the same.

Many leaders still want to control every aspect of their organization. But the companies that let go of that control, democratizing decision making and embracing the full capabilities of their employees, will outpace those who centralize decision making and look to control results.

They already are.

In a future post I’ll detail exactly how we went about implementing this approach at VNN, and the structures we use today to ensure everyone has the appropriate context to UGJ (Use Good Judgement, which we stole from Netflix like any good artist).

It’s also worth noting that the above is nowhere near the leading edge of management. Recognizing the futility of pretending to control the future, some companies have gone so far as to eliminate the annual budget entirely. We still have a budget, but I must say this is very intriguing.

Do Less, Better

Inspiration sparks the best ideas, creative process crystalizes them, and perspiration makes them come to life. Three parts of the value creation chain.

We startup founders are excellent at the perspiration part. We push and push, optimizing for a constant state of busyness, checking off more boxes than we did yesterday. Eliminating more gaps in our schedules in favor of “GSD” (getting shit done).

In doing so, we feel productive. We’ve been conditioned to “do more, faster“. And that’s not wrong, but the question is at what cost?

Inspiration and creativity require one thing: Space. The very thing that our quest for productivity would have us eliminate. We’ve been sold a line that we must hustle ad infinitum, and bought it wholesale with little awareness of the implications.

Nothing happens without perspiration. It is the core characteristic of successful founders, and foundational. But successful founders get that part, and then go too far.

With the way we glorify the hustle as founders and leaders, is it really a surprise that true inspiration and creativity have become so rare? Why everyone is just the “AirBnb for pet crates” or the “Uber for luggage”?

Scaling value while also scaling variability

Scaling a business, we’re told, is about establishing processes, procedures and workflows, to ensure that the value that you created when you were small persists as you grow. The goal being to ensure that every experience your new customers have is of the same value as the experiences your early customers had. To do so, it seems, you have to eliminate variability to prevent substandard customer experiences.

But variability drives innovation. Without random variation, single celled organisms never evolve into human beings, and nobody even has the luxury of thinking about scale. Variability is the singular engine driving adaptation, growth, and increasingly, in the rapidly changing world we live in, survival.

So can we scale both value and variability? Should we?

You simply can’t replicate the chaos that permeates an early stage startup as a company grows, and you shouldn’t want to. We all have enough grey hairs from that time. But if we convince ourselves that there is a “right way”, then our teams will hew ever closer to that. Then, innovation stops, people get caught up in dogma, and the company struggles to meet evolving expectations in a dynamic market.

Even though everyone in the company is doing everything “right.”

What if we aimed instead to scale not only the value creation that we cultivated at a small size, but also the variability that helped us find that value creation in the first place?

As an example, what if instead of a “right way”, we instead scaled a “default way” for our teams (HT: Aaron Dignan), while also giving them autonomy to deviate if it made sense? If we did this, our teams could do what had been proven effective in the past, but they could also change things if they thought it was for the better. They might be wrong, or they might be right, but either way the organization would be smarter having conducted the experiment.

Might we be able, this way, to scale customer experiences better than the ones we first had success with?

The case for the startup psychologist

Cofounders are effectively married, so why do we not invest in couples therapy for startups? It works.

There is no more fundamentally important relationship inside a company than between its cofounders, and no area in which things can get more royally screwed. By extension, that applies with only a very slight reduction to the founding team and/or leadership team, the group of people with varying functional areas who through their relationships guide the direction and success of the company.

Market, strategy, culture, all of these things are important. But none of them can overcome bad relationships within the leadership of a company.

So why do we, as founders and investors, not invest in nurturing and securing those relationships? And in the rare cases where we do consciously, why do we expect success from people without any professional expertise?

We rely on board members, usually business leaders all, and the founding team itself to fix these matters. This is like handing a drill to Mike from Accounting and asking him to fix your cavity. He’s not trained in dentistry, so you don’t hand him a drill.

A board and founding team are not doctors in psychology (much less do they possess the required dispassion to do the job with objectivity), so why in the world do we so unquestioningly trust them with managing the psychological dynamics of the leadership team, the single largest lever in our organizations?

I’m piling on here, as it is definitely encouraging to see groups like Freestyle Capital investing in the mental health of their founders. This is critically important and they are pushing the envelope, far, to do even that, but it’s about more than the mental well-being of the individual. We need to go farther, and invest in the mental well-being of the leadership team (if not the organization).

Innovation in the fight game

Ducking a superman punch to open the fight, Donald Cerrone grabbed at Conor McGregor, wrapping up the shorter striker’s arms in a clinch.

The fight prior, Holly Holm leveraged the clinch dozens of times in a 15-minute contest on her way to a win against Raquel Pennington, illustrative of just how frequent this technique is. By tieing up all four arms the fight grinds to a halt. The fighters push and grind against one another, trying to establish an angle to strike while avoiding being taken to the ground.

But McGregor changed the sport of MMA last night in Las Vegas when, his arms tied up in a clinch, he crouched and launched himself shoulder-first into Cerrone’s cheekbone. McGregor shouldered his opponent’s face thrice more before Cerrone finally backed away. By then his nose was broken, and the fight was over 20 seconds later. Cerrone never landed one strike.

“I’d never seen anything like that before,” Cerrone, a veteran of over 50 professional fights, said afterward. Joe Rogan, who sits cageside for nearly every UFC event, agreed.

Nobody had. Shoulders were irrelevant in the thousands of fights and perhaps millions of clinches prior. But this morning, fighters around the world began drilling shoulder strikes in the clinch, and we’ll see more shoulder knockouts to come.

Innovation is obvious in hindsight. But every “industry standard” practice has a beginning, before which that practice seemed as weird as jump-punching someone with your shoulder. Or jumping up and throwing the ball down, rather than shooting it up into the hoop.

Someone always has to go first.