We can finally define what it means for someone to be differently free from you. They are people who are playing just a slightly different game than you are. That difference makes them a reliable sources of non sequiturs in your life. Waiting for nature to present you with a parrot or a piece of corn to awaken you out of a finite game is a tricky, chancy business.

Differently free people change the equation in an interesting way. When you include a person in your life, it is because they have a definite worth (possibly negative) in whatever finite game you’re asleep in at the time. This means there is at least some overlap between their game and yours; some similarity between how you keep score and how they do. Some meaningful relationship (possibly adversarial)  between how you define winning and how they do.

This means you have a model of the person in your head. One that predicts how they will value things.

it is the parts that don’t overlap that matter. There are things that have a defined worth in their lives that are non sequiturs in yours, and vice versa. When you see through the eyes of a differently free person, you expect to see a landscape of presumptively valued things. A landscape based on your predictions of how they value things. When the other person appears to value something that doesn’t even register with you, for a moment, that thing turns into a non sequitur, a candidate parrot. It lingers just a little bit longer in your own mind than it would if you yourself saw it. Long enough that you do a double take and notice it consciously.

My alternative to the heuristic, which many of you have heard in off-blog conversations, is that I am only interested in people as long as they are unpredictable to me. If I can predict what you’ll do or say, I’ll lose interest in you rapidly. If you can keep regularly surprising me in some way, forcing me to actually think in unscripted ways in order to respond, I’ll stay interested. It’s reciprocal. I suspect the people with whom I develop long-term relationships are the ones I surprise regularly. The ones who find me predictable don’t stick around. We’re not talking any old kind of surprise, but non sequiturs. Surprises that you can’t really relate to anything else, and don’t know what to do with. Mind-expanding surprises rather than gap-closing surprises.

The useful thing about defining good design as a form-context fit is that it tells you where you will find the form. The form is in the context. To find a good relationship, you do not start by saying, “I want a relationship that looks like this”—that would be starting in the wrong end, by defining form. Instead you say, “I’m just going to pay attention to what happens when I hang out with various people and iterate toward something that feels alive”—you start from the context.

The context is smarter than you. It holds more nuance and information than you can fit in your head. Collaborate with it.

If you want to find a good design—be that the design of a house or an essay, a career or a marriage—what you want is some process that allows you to extract information from the context, and bake it into the form. That is what unfolding is.

The opposite of an unfolding is a vision. A vision springs, not from a careful understanding of a context, but from a fantasy

Anything that increases the rate and resolution of information you get from the context will help. And anything that makes it easier for you to act on the context.

A common reason we filter information and become blind to the context is that we bundle things when we think. Thinking about our career, we might think in abstractions like “a job.” But really a career is made up of a bunch of different things like a salary, an identity, relationships, status, a sense of meaning, and so on. It is often easier to find a fit if you unbundle these things, and think about the parts that matter to you individually. Do you actually need more status? Or can you find a better fit if you go low status?

Another common reason the feedback loop of unfolding often works poorly is that people have decided on a solution already. They have turned on their confirmation bias. They have decided that a certain solution is off-limits. Let’s say you are 34 and haven’t found a partner but want kids. If we unbundle this, it is clear that the problem of having a kid and the problem of love are not the same thing, so you could solve your problem by having a kid with your best friend instead. But this feels weird. It is not the vision you have for your life. And it seems dysfunctional. Observe that feeling—it is, perhaps, a part of the context. There is some information there. But to unfold, do not write off any solutions. Leave them all on the table; let them combine and recombine. Many good ideas look bad at first. To increase the rate at which you understand the context, you want to develop a certain detachment. When the context thrashes one of your ideas, you want to say, “Oh, that’s interesting.” It takes practice. But it is worth getting better at. Reality is shy—it only reveals itself to those who, like honest scientists, do not wish it to be something else.

The faster you can collide your ideas against reality, the faster you get feedback.

The school system is centered around visions, not unfolding. You are asked to make decisions about realities that are five, ten years down the line, and you get no feedback on your decisions.

you’re less torn by anxious attachments when you recognize how something must naturally and necessarily unfold.

Knowledge is freedom from getting mad at facts.

Detachment does not mean you don’t care what happens. It just means you don’t care whether a specific thing happens or not. You want to know the outcome of the coin-toss (you care), but you don’t care whether it is heads or tails even if you’ve bet on heads (you’re not attached to a specific outcome). The important thing is that something happens, which means you’ve successfully kept play going, but without keeping score.

Emotional Self-Management: I like to think of this as accepting the emotions you have instead of having emotions about having emotions in an endless stack.

Fear. Not fear, plus anxiety about fear, plus guilt about anxiety about fear, plus shame about displaying guilt about experiencing anxiety about having fear. This is emotional focus. Instead of retreating from an emotion through layers of additional emotions until you find one you can deal with, you experience the actual emotion for what it is.

VCs need to believe that your company could be a billion-dollar business and generally lack imagination — you need to paint a vivid picture of this path for them, starting with the striking protagonist character you play in your company’s story.Your alter ego should never lie, but it should be completely comfortable showing the fullest expression of your ambition to people who probably intimidate you. Fundraising is a snap judgment game — most VCs are trying to pattern-match you to a founder archetype who already won. They index primarily on IQ, self-belief, experience, and personability (in that order). A general rule of thumb is that to be taken seriously in SV, male founders would benefit from acting warmer, while female founders are taken more seriously when they act colder. Both benefit from acting a little entitled.

a VC’s job is to make a diversified portfolio of bets — you are only one. Most founders find being around VCs distracting and draining because they feel pressure to perform the role of ‘impressive person.’ If you can’t immediately capture value from your performance… why waste your energy?

don’t expect the average investor to provide much value beyond money and connections. This makes the 10% of investors who can be legitimately useful to your business worth their weight in gold. Develop litmus tests to identify the valuable ones quickly and avoid wasting your time trying to convince nonbelievers.

our goal here is to spend as little time fundraising as possible — which requires being strategic about the order in which you talk to investors and how you talk about where things stand as you progress through the raise. The combined force of controlling those two variables are what “generates momentum” during your fundraise process.

Make a list of all the investors you know and can get introduced to, ordering them by the ones you most want on board to the ones you couldn’t care less aboutTalk first to a few low-stakes investors at the bottom of your list to practice your pitch and identify common investor questions and critiques you’re going to getIf available to you, next get a few investors who already wanted to give you money on board so you have a dollar amount you can say you’ve raisedWork your way up your investor list, talking to the investors you most-want-on-board-but-still-need-to-convince last (this optimizes your odds they say yes)

This all goes by much faster if you court investors similarly to how hot girls treat their many potential suitors. If your raise is already a little taken and you exude an air that you don’t need them, mimetically-minded investors become much more interested.

If you’re anything like me, you will worry intensely about not making a fool of yourself. It will probably go ok, but not as amazing or illuminating as you’d hoped. You might leave and feel a deep sense of lostness set in. This is all very normal. In time you will see them in increasing clarity, often noticing the differences between your and their values and why you would not enjoy living their life at all.

the people on pedestals probably hate being there. It’s lonely, hard to trust that the intentions of the new people around you are pure, and you often feel like you’re constantly letting people down. In the end, idolization hurts everyone involved.

Beware of intellectual dementors and clout demonsIntellectual dementors will try to eat your ideas and interestingness — not necessarily to copy you, but to wring your brain dry to amass knowledge themselves. They often play mini IQ games/tests of will in conversation and masquerade as investors while never actually investing. Clout demons are similar, but view people less as brains and more as stepping stones towards supreme social status. The power move to protect yourself from both is to simply abstain from playing their games — give as little info on yourself and your ideas as possible and reflect their questions directly back at them.

People will help you if you ask for what you want clearly and concisely

Knowing what you want requires a lot of upfront soul-searching, followed by strategic and long-term thinking once you’ve committed to a thing (I can’t really demystify this more). Once you’re all in, I highly recommend diligently keeping a list somewhere of the top three things you currently need help with so when people ask, you’re ready.

You don’t want to make people feel like you’re using them but you do want to use your social capital for things you care about. General rule of thumb: ask for things either 1) after a positive interaction or 2) completely out of the blue with a concisely written and compelling email/text. Tone matters because you don’t want to sound desperate and you do want to show you know how to play the game (write like the founder you most admire talks).

once we’ve taken action on behalf of something, our brain assigns more value to said thing. Tim Keller: “The feeling of love follows the action of love.” Love is a strong word here, but the point stands — help people help you. Startups are long-term games, so it only makes sense to do them with people you truly want to be around for a very long time.

resist the urge to add immediate value. Instead we have to hold space for a more vulnerable, honest and open relationship with our client - to allow them to open up more fully and to work on things that are useful, even if not in scope.

While giving advice can help you be seen as knowledgeable, it doesn’t necessarily build trust.

“You should…” It’s a simple sounding phrase but it gets you in trouble more often than not. It’s problematic for two reasons: it assumes a control of client resources and it’s too prescriptive in form

We typically don’t have a complete view of everything that the company is working on, we don’t have a detailed understanding of how long things actually take or the full range of dependencies required for them.

Example: working with a client where I wanted to re-design a landing page on their site to improve it. Unfortunately I was under-estimating the number of people who need to be involved since the landing pages were still owned by the product team and are technically part of the same codebase as the full tech product. So a “small” change required detailed security scrutiny and QA before going live. Making “simple” changes was not in fact simple at all here.

Example: working with the NYTimes cooking team I suggested that they should re-tag their content. This kind of “you should…” recommendation seemed straightforward but neglected the political considerations - the team had just spent 6-figures on re-tagging all their recipes - so to ask for further budget to re-do a task they had just done would lose them face internally. A “straightforward” change that actually carried a bunch of political baggage.

Some other types of complexity that you might be under-estimating with regards resource allocation: Regulation/compliance complexity - which either prevents you even doing your recommendation or makes it slower. Technical complexity - while something might be technically easy, doing it with the client’s existing technology might be hard. Data complexity - a simple seeming request on the surface (make a landing page for every neighborhood) might actually depend on a robust, maintained data set that doesn’t yet exist. Maintenance complexity - even if the initial request to create something or do something is not resource intensive, it might come with an implicit agreement to continue to maintain it - expanding the resources allocated. Production complexity - where what you’re proposing isn’t that expensive or resource intensive to do, but the client (for whatever reason) has a higher quality threshold, making the recommendation more expensive/slower/harder than you anticipated. Narrative complexity - where what you’re recommending seems reasonable but either the company has tried it before, or a competitor has tried it before or there’s a general sense that “this doesn’t work”. Which can make your recommendation extremely hard to actually get done.

When we say “You should…” we’re essentially offering a problem diagnosis AND a solution at the same time. The consequence of this is that we’re essentially asking the client to accept or reject both together.

most of your work would be more effective at actually changing clients if you stopped to clearly separate the diagnosis from the solution.

if you’re asking “You should…” to the client, stop and examine if you’ve properly defined the situation and provided evidence for the problem, to help the client deeply internalize the problem and win over the necessary stakeholders before you propose any kind of solution.

A good mental exercise to ensure you’re doing the work here is to ask yourself: what happens if the client takes no action? What is the consequence of the current trajectory, or the null case of no investment?

By showing what’s possible, clients are able to feel more invested in designing the solution with you, rather than just being told what to do.

clients deeply appreciate you clearly separating out expert opinion and judgment from evidence-based analysis.

A good process for the advisor to follow is: Give them their options Give them an education about their options (including enough discussion for them to consider each option in depth) Give them a recommendation Let them choose

Taking a collaborative stance with your client is powerful. There are many aspects of consulting that are almost combative by nature - like pointing out problems the client has (that the client was complicit in creating!).

I find in my own work that senior executives are often blocked by some inability to see what’s actually going on - and that telling them is useless! Instead you need to help them see it for themselves.

Because of their distance from the day to day work, senior executives are especially prone to replacing some version of reality with a compressed narrative. And when this compressed narrative is wrong in some key way you need to return to first principles to show them (not tell them!).

Your sense of “what’s going on” with a client is intermediated by your point of contact and it turns out that your client is an unreliable narrator.

When a client comes to you asking for a “content strategy” or support “hiring a VP marketing” it all seems so straightforward, rational and well defined. But as you unpack the layers of the onion you begin to realize why it’s been so hard for the client to help themselves. And that’s when the emotional and political complexity of the problem starts to come into view.

if the work is done effectively, it requires that the consultant be both involved enough in the dynamics so as to experience their impact and detached enough so as to analyze what is transpiring. These demands make imperative the use of oneself as tool.

always work on the next most useful thing. This mantra helps remind me that consulting isn’t about being right, it’s about being useful.

I delivered what I think is good quality work with a deeply researched and evidence-based 66-page strategy for producing content and…. Nothing happened? They were happy enough with the work product but it didn’t lead to any material change in their strategy or an ongoing consulting relationship. In hindsight the key mistake here was not asking myself enough what the next most useful thing was. I think if I’d been more honest about what would add value and show momentum for the client it would have been either a) condensed one or two slide summary of the content opportunity for their fundraising deck and/or b) supporting their VP marketing recruitment effort.

Either you’re telling the client “draw some circles” and the client is frustrated the advice is too basic and high level. Or you’re telling the client to “draw the rest of the fucking owl” and are ignoring the detailed reality of the situation and the limitations of teams, resources and capabilities.

Or worse, the client asked you for help drawing owls but what they’re really doing is painting a woodland scene…

Think about this image next time a client comes to you for help drawing owls - your first response shouldn’t be “Oh, that’s easy, first you draw some circles”, it should be “Show me how your owls look today. What do you think is holding you back from drawing better owls? And why is drawing owls important to you right now?”

Remember - it’s about adopting a collaborative, trusted stance with clients. And that might require resisting your initial urge to give advice. Instead you need to listen to the full emotional and political situation and then work with the client to re-examine reality in new and surprising ways. Always work on the next most useful thing. And that doesn’t always involve doing what the client asked for.

If you were magically given 10,000 hours to be amazing at something, what would it be? The more clarity you have on this response, the better off you’ll be.

Scott Adams popularized the idea of finding the intersection of 2-3 things you’re best at even if you’re not best at any of them individually. He wasn’t neither the best cartoonist nor the best writer nor the best entrepreneur, but he was the best combination. It could be a combination of expertise, relationships, sensibilities, and skills that you’ve accumulated over the years. If you’re just starting out, ideally it picks up where your childhood left off. Now, I spent my childhood trying to make the NBA. So if like me, you misallocated your childhood in the skills department, you have to be more creative. Later on, I realized I could apply the self-discipline and systems thinking I deployed when trying to be good at basketball into other fields, and found some that better fit my natural abilities.

If you’re a generalist, you want to be the best at the intersection of a few different skills, even if it’s a few disparate things. The challenge is it's easy to lie to yourself & say that you're a generalist when in reality you've tried a bunch of things and you've flaked out when things got hard and then tried something else.

Some people who you think are generalists have also specialized. Malcolm Gladwell for example writes about lots of topics, but he's mastered the art of translating academic work for a mass audience. Tyler Cowen self-defines himself as specializing as a generalist, but he spent a couple decades going deep on economics.

A personal moat is a set of unique and accumulating competitive advantages in the context of your career. Like company moats, your personal moat should be a competitive advantage specific to you that's not only durable, but compounds over time.