#unfiltered #76 The Forcing Functions of Change

autumn, leaves changing, fall

One of my favorite frameworks of thinking about building and breaking habits comes in the words of Elliot Berkman, whom I’ve cited before. He notes that there are three factors to breaking a habit.

  1. The availability of an alternative habit
  2. Strength of motivation to change
  3. Mental and physical ability to break the habit

Of particular note is the second one. The strength of motivation to change. Change is inevitable. But real change is always compelling. There must be a strong enough desire to relieve yourself of the status quo. John C. Maxwell once said, “People change in four different seasons… People change when they hurt enough they have to, when they see enough they’re inspired to, when they learn enough that they want to, and when they receive enough that they’re able to.”

In each of those seasons, the person is compelled to do something outside of their ordinary flow of time. But there’s another interesting way to think about change. One where you have no choice but to.

CIA veteran Richards Heuer once wrote, “When faced with a major paradigm shift, analysts who know the most about a subject have the most to unlearn.” If there’s anything we can gather from historical records, major paradigm shifts are happening every decade (and less) whether we want to or not. On a macro scale, new technologies, like generative AI, the smartphone, and the internet, as well as political and financial eras, like the GFC, the dot com burst, and wars that affect the increasingly interconnected world. On a micro scale, when we go to college, get our first job, start our first company, raise a family, or buy your first house.

At each stage, the more entrenched you are in the behavioral patterns of the status quo, the harder it is to adjust with the next shift. For instance, as a founder, anchoring yourself on 2020-2021 multiples and valuations won’t help you in the world forward. As an investor, anchoring on the past 3-4 years of markups without fully accounting for the current climate won’t help you with your next raise. Anecdotally, I’ve heard great multi-fund managers mark their portfolio down by 25% already before the market verdict comes in. Moreover, jobs are going to look very different in an age of AGI (artificial general intelligence). Just like with the industrial revolution, new jobs will be created. And I can go on on and on. But I digress.

There’s a hero’s arc in each inflection point. Every time the second derivative goes from negative to positive. The way Viola Davis puts it that that at the end of every hero’s journey, you come face-to-face with not a god, but yourself. And that is when the magic happens.

“Somewhere along the line is a voice deep within you that tells you exactly who you are; you just have to have the courage to do that. That’s what the journey of the hero is all about. You’re born into a world where you don’t fit in. You answer the call to adventure. And you deny the call. Then at some point you then set out on your path. You slay dragons, and you do all of that. At some point, you come face-to-face with not a god, but yourself. Somewhere along the line, you get it — your A-ha moment. Your elixir. And you go back to your ordinary world and share it with others. I think that’s the journey. I think that’s the privilege of being absolutely who you are — belonging to yourself and being brave.”

— Viola Davis

Photo by Chris Lawton on Unsplash


#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.


Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!


The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

#unfiltered #74 What If Events Were Story Arcs?

castle, story, boat

“Somewhere along the line is a voice deep within you that tells you exactly who you are; you just have to have the courage to do that. That’s what the journey of the hero is all about. You’re born into a world where you don’t fit in. You answer the call to adventure. And you deny the call. Then at some point you then set out on your path. You slay dragons, and you do all of that. At some point, you come face-to-face with not a god, but yourself. Somewhere along the line, you get it — your A-ha moment. Your elixir. And you go back to your ordinary world and share it with others. I think that’s the journey. I think that’s the privilege of being absolutely who you are — belonging to yourself and being brave.”

That’s the arc of every great story in the words of Viola Davis on one of my new favorite interviews with Sean Evans, where she shares the secret to the hero’s journey.

In the world post-pandemic, people crave connection. A desire to go from URL to IRL. Everyone lost those years. Something everyone from a first grader to a college student to a young professional entering the workforce to a retiree could relate to. And in 2021, there was a re-emergence of events. Well-intentioned and well-founded. We had conferences, coffee chats, happy hours, fireside chats, oh, so many happy hours, panels, tech weeks, and… did I mention happy hours?

Most events out there are a time and a place for a collection of people. They’re static points in time. Not even counting the full spectrum of event planners, many of the best event planners spend tons of times on what makes events special, but change more about the small bells and whistles of an event than the overall flow. There are very few who take leaps of faith. Even less true for the vast majority of events, where events feel more of an afterthought than something that is designed to start or end a chapter in your life.

As such, everyone found themselves left with a goodie bag including a surplus of events, a lack of focus and attention, and a lollipop of exhaustion.

So, I had a thought last year, greatly inspired by my team at On Deck Angels. Instead of trying to host an event a month, what would need to change if we could only do one event a year? What would we have to do? Hell, extrapolating further, what if we only did one event every two years? Three years? Every Olympic arc? Which led to the thinking around, what do we need to do to make this the most memorable event that anyone has ever been to.

You see, I’ve hosted and co-hosted small and large-scale social experiments, but it was always for an audience who proactively and voluntarily signed up for. They were willing to do things outside the ordinary. But could I apply the same learnings to events for really, busy people who crave intellectual challenges, and who have been to so many events, they might be jaded?

So, below was and continues to be my collection of governing thoughts around answering that question, which will only grow and refine this year. In the theme of my blogpost last week, the below may be messy. Disorganized. Chaotic, even. Hope not, but possible. You’ve been warned. But I do hope that you might find at least one of the below frameworks useful.

Metrics for success

Every event needs a North Star. When planning the Angel Forum, as well as future events, below are mine.

  1. Attendees go on a hero’s journey, revisiting Viola Davis’ words above. In other words, character development. The event should create opportunities for growth within the event itself.
  2. Every attendee continues to and is motivated to build friendships (as opposed to networking and purely transactional connection) after the event. If the event itself is the only reason for people to connect, but it does not give people incentive to after, it’s a failure (in my books).

For now, that means, not only the speakers and the presenters need to be curated, but also each and every person on the guest list. I have yet to figure out how to customize such experiences at scale, where each person has wildly different goals.

Narrative frameworks I use for events

To dig a level deeper, here are my frameworks for execution:

  1. Surprise and suspense — Surprise is when you relay information that the audience does not expect. Suspense is when you relay information that the audience is expecting, but does not know when it’ll drop. Suspense is how you keep attention. It raises expectation, but knowing when to deliver the news helps with creating a reality that meets or beats expectation. Surprise is, on the other hand, purely for creating alphas in this expectation-versus-reality model. It’s the main driver for overdelivering on a seemingly smaller, but still powerful promise. To do so, I find George Loewenstein’s 1994 paper on the psychology of curiosity super helpful. More on how the five triggers to curiosity influenced my thinking here.
  2. Candy versus the meal — A Malcolm Gladwell framework. Effectively, how people think and what people actually talk about are quite different. Candy is what people talk about. For example, if I were to talk about the recent Avatar movie, I’d talk about how amazing the motion capture and the CGI was. And in doing so, I’ve spoiled nothing. It tells you nothing about the plot, but it’s exciting to talk about. On the other hand, the meal is how people think. It’s the whole package, the whole story. The meal has to be well-worth the visit, but the candy is what gets people excited. More on that in a previous essay I wrote here.
  3. The audience must understand the rules of magic — This is a combination of the thoughts of Malcolm Gladwell‘s framework around tools and Brandon Sanderson’s three laws of magical systems. Give the audience tools to use at the very beginning of the event. It could be a framework for how to think about the event and every activity in between. It could be physical tools that they will employ throughout the event. And once you do, make sure your audience knows how to use those tools. Test them. Give them small, but easy case studies and questions. Make it easy. Don’t put them on the spot. And by completing that test, that satisfaction and joy will help motivate them to use it more later. As Sanderson’s first law of magic goes, “your ability to solve problems with magic in a satisfying way is directly proportional to how well the reader understands said magic.” More on my thoughts on Sanderson’s laws here.
  4. Plots — Like any good story, the narrative is governed by plots. The plot must thicken and build towards a climax. And it must be resolved by the end of the event. Leave little in the main plot to chance, but leave room for each guest to discover something extraordinary. Maintaining a minor amount of stress and uncertainty, while sharing examples and reminders of being open-minded to new experiences, goes a long way. Only after stepping outside one’s comfort zone can one grow.
  5. Always use the audience’s time in a way that does not feel wasted — Inspired by one of the greatest writers of all time, Kurt Vonnegut. I forget which lecture he did that I learned this from. But it’s always been a governing theme for what I do.
  6. End on an ending where the reader can imagine no other — No loose ends. Everything that is teased (whether the audience realizes it or not) needs to be resolved by the end. This might be a semi-controversial opinion among storytellers and creative professionals. But I’m biased. I like my stories to end with a bowtie.

In closing

As you might imagine, much of this is still incomplete. And I hope to share more as I continue down this path of exploration and discovery.

Photo by Artem Sapegin on Unsplash


#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.


Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!


Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.