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Hujambo! Welcome to this week's digest. This week is a very special "Stepping Out(side Ourselves)" edition, as we explore the power of alter egos, trading malice for stupidity, dating app sobriety, risk mitigation in entrepreneurship, and life lessons. Enjoy!

 

Two semi-random questions for the esteemed gallery:

  1. MARKETING - Are there any places where you think TD Digest ought to be shared broadly? In my consulting practice, I tend to 'market' in-person and 1-1, so my 1-many digital marketing skills are completely non-existent ;D
     

  2. TRAVEL - I will be exploring Southeast Asia for the very first time in December! Specifically Thailand (Bangkok, Phuket, Chiang Mai), Singapore, and Vietnam (Ho Chi Minh City). Do you have any recommendations for a naive first-timer?

XOXOXO <3


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TDD TL;DR
  • MENTAL MODEL OF THE WEEK - HANLON'S RAZOR - Never attribute to malice that which can be adequately explained by stupidity.
     
  • EXPERIMENT - DATING APP SOBRIETY - Deleting dating apps for the month of November to remember what it is like to meet potential partners in real life.
     
  • BOOK - The Alter Ego Effect by Todd Herman (Thank you Cam for sharing!) (My Summary) (My full Kindle notes) - Adopting an alter ego can be a viable and fun path to accepting and living into parts of ourselves that we previously wouldn't or couldn't.
     
  • BLOG POST - Letter to a friend who may start a new investment platform by Graham Duncan - Graham's eloquent letter elaborates on a number of important and prominent hang-ups related to entrepreneurship, like feeling sales-y, the opportunity cost of not pursuing our dreams, leaning into our compulsions, the role of money in our lives, and the impact of professional volatility on our various relationships.
     
  • BLOG POST - Brain Pickings: 13 Life-Learnings from 13 Years of Brain Pickings by Maria Popova - Maria updated an incredibly thoughtful and insightful listicle with a few more important lessons learned.

"So many of us choose our path out of fear disguised as practicality." ~ Todd Herman
 
OTHER INTRIGUING CONTENT

RESEARCH

PODCASTS
ARTICLES
  • Aeon: We have the tools and technology to work less and live better - "...today’s discussions need to move beyond the old point about the marvels of technology, and truly ask: what is it all for? Without a conception of a good life, without a way to distinguish progress that’s important from that which keeps us on the hedonic treadmill, our collective inertia will mean that we never reach Keynes’s 15-hour working week."
     
  • The New York Times: Why Don’t Rich People Just Stop Working? - "Apex entrepreneurs and financiers, after all, are often “adrenaline-fueled, transgressive people,” Dr. Karasu said. “They tend to have laser-focused digital brains, are always in transactional mode, and the bigger they get, the lonelier they are, because they do not belong.”"

BLOG POSTS
SHAMELESS PLUGS
MENTAL MODEL OF THE WEEK - HANLON'S RAZOR

Per Wikipedia, the source of infinite wisdom, Hanlon's Razor is an aphorism commonly expressed as "Never attribute to malice that which can be adequately explained by stupidity." This fundamental explanation for human behavior is instrumental in debunking many conspiracy theories, particularly those related to prominent politicians and business leaders, as well as debunking pernicious internal narratives, e.g., [Joe] was [late] because he hates me. This mental salve helps me see the world through (I believe) a more accurate lens that even the worst outcomes are still a product of mostly good people, doing their best (which includes fucking up on occasion), and operating within their environment and incentives. As a result, when thoughtfully applied, Hanlon's Razor is a tremendous stress reducer in my life :D

Note: For two incredible lists of mental models, check out Farnam Street and Gabriel Weinberg.
EXPERIMENT - DATING APP SOBRIETY

TL;DR: For the month of November, I am deleting all dating apps, in order to remember what it feels like to meet potential partners in real life.

For those of you who don't know me personally, I am currently single, and have been actively dating and in exclusive relationships for the past ~15 years. For the past ~10 years I have used digital dating apps, starting with OkCupid way back in 2009 in Chicago. Dating apps primarily served three functions for me: (1) Source dates I would have never met in real life; (2) Allow me to source dates at my convenience; (3) An emotional crutch to avoid the sting of rejection in real-life situations. And dating apps have been at least partially successful for me, in terms of both date volume and dating outcomes. For example, in NYC this past year (a biased sample because of local market distortions, but bear with me), I went on dates with ~75 women, resulting in 1 five-month relationship, and 3 one-to-two month relationships.

However, there are a few semi-hidden downsides to dating apps that make me feel like I must hit 'delete': (Note: These are ridiculously analytical, but all ultimately serve the purpose of cultivating a meaningful emotional connection :D)

(1) The Cost (Non-Monetary) of Finding Quality Dates - Roughly 10% of first dates from dating apps were mutually 'high quality' (i.e., ~20% I end up feeling excited about, and ~50% of those end up feeling excited about me, too). Apply some marketing funnel math, though, and it takes roughly 6-8 matches (cold leads) on dating apps to actually go out on a date, due to non-responsiveness, not clicking via text, timing, etc. That means to go on a quality date, it takes ~60-80 matches! That is a lot of time, effort, and energy to find mutual chemistry. And all of that time might be 'convenient', but I can think of 10 things I'd rather do with that time than be on dating apps.

(2) The Limited Nature of Digital Interaction - Dating apps have helped me become incredibly humble in terms of how much I can learn about a person via text and photos vs. real-life interaction. Digital interaction is simply too constrained of a communication medium - we miss out on so much of the richness of human communication, like tone, body language, and pacing. Based on my experience, I can learn more in 30 seconds of in-person interaction than years of texting and sharing photos.

(3) Biased Marketing Paradigms - Similar to a company using Facebook ads to sell products, when I choose to use dating apps, I am a slave to both their algorithms (i.e., when I get shown to someone) and their native marketing norms (i.e., how people typically compete in the marketplace to get dates). In the quest to monetize (understandably), dating apps are starting to charge for algorithm favoritism / enhanced visibility (e.g., anything related to 'boosting' profiles). And the native marketing norms for dating apps are not aligned with how I find quality dates, or want to be found (e.g., photos and a brief description). There are layers of complexity in people that I delight in discovering, and which are not revealed well within dating apps as currently constructed.

(4) Addiction - Dating apps are literally the only phone use case where I struggle to control myself and feel compulsive. After all, pure, unconditional, and infinite love is only one notification or swipe away ;D

When I adjust the purported benefits for living in NYC, it has become clear that the only reason why I still use dating apps is their third benefit, to avoid the initial vulnerability of talking to an attractive stranger and the potential sting of rejection. When I lay out the opaque costs clearly, this is a deal that I no longer find acceptable. So for the month of November, I am going sober and living life dating app free :D I feel very excited, kind of nervous, and curious about what impacts this will have on my life.

 
BEST OF WHAT I CONSUMED THIS WEEK

BOOK - The Alter Ego Effect by Todd Herman (Thank you Cam for sharing!) (My Summary) (My full Kindle notes) - At its core, Todd's book is incredibly inspiring, concrete in its recommendations, action-oriented to get you moving, and also playful. Adopting an alter ego can be a viable and fun path to accepting and living into parts of ourselves that we previously wouldn't or couldn't. The stereotypical downsides of the self-help category, i.e, pseudo-science and tons of filler anecdotes, are definitely prominent here, too. That said, per the ACT framework, rather than judging as good or bad, judge as helpful for achieving your goals or not; and the alter ego concept detailed in the book feels incredibly high potential at face value.

What do I do now?: Identify one 'Field of Play' where you would be excited to adopt the alter ego approach, then begin sketching out what that alter ego would achieve, do, look like, and act like.

Complement with How Champions Think (TD Digest summary).

My highlights:
  • Our personalities are malleable. We can reshape ourselves. We can change our beliefs and create new habits. We can change our identities. That’s what the Alter Ego does for us. It helps us to tap into dormant capabilities and traits that we just haven’t used, or haven’t used in a setting that we want and need them in.
     
  • Channeling a “different” identity helped [Bo Jackson] focus every ounce of his talent and skill, and enabled him to show up on the field, without any emotional issues interfering with his performance.
     
  • “In my mind, I wasn’t losing a tennis match. I was failing as a human being because being a tennis player was my identity.” Okay, let’s pause and replay that statement: I was failing as a human being because being a tennis player was my identity. Does that resonate with you? If you’re ambitious, it most likely does.
     
  • It may be difficult to look at your life and call yourself a “performer.” You may not be “performing” in the context of a Beyoncé, Ellen DeGeneres, or David Bowie, with thousands of people expecting a “show,” but if you think about “show” as simply a fulfillment of expectations, you’ll see the parallels very quickly.
     
  • Most people are unfortunately using their imaginations to play out scenarios that look like horror stories. It causes them to retract and move away from their goals. But if I asked them to imagine themselves showing up in that same scenario as Wonder Woman, Mother Teresa, or Princess Leia, they could imagine a very different result.
     
  • We are judged in our lives by what we do, not by what we think or intend to do… We must all suffer one of two things: the pain of discipline or the pain of regret… At the end of your life, you won’t remember the thoughts or intentions you had. You’ll remember the actions you took.
     
  • These narratives or stories we’re telling ourselves are important because unconscious ideas and emotion drive action. Each of us is driven more by our gut feelings than our thoughts.
     
  • So many of us choose our path out of fear disguised as practicality.
     
  • All I concern myself with is whether my clients’ actions, thoughts, and emotions are aligned with what they really want. When we’re aligned, that’s when the magic happens. Most of us aren’t aligned.
     
  • Self-expression is a core driver of people motivated by merely wanting to answer the question, “I wonder what I can do/create/find?” Some people are just deeply motivated to uncover “what they’re made of” and love the creative, athletic, or scientific process.

     
BLOG POST - Letter to a friend who may start a new investment platform by Graham Duncan - Graham's eloquent letter elaborates on a number of important and prominent hang-ups related to entrepreneurship, like feeling sales-y, the opportunity cost of not pursuing our dreams, leaning into our compulsions, the role of money in our lives, and the impact of professional volatility on our various relationships.

What do I do now?: Set a price for the next five years of your life. What are you willing to sell that for? Do you feel that you are getting that deal from your current professional path?

Complement with Tim Ferriss Show #148: Josh Waitzkin, The Prodigy Returns (TD Digest summary).

My highlights:
  • Start-ups of any kind are awash in ambiguity. It’s the founder’s responsibility to hold that ambiguity for everyone, which is often a lonely job. As you move from “refining reality” in your old job to “asserting reality” as you create something from nothing, you will inevitably encounter the cognitive dissonance borne of having to act as though everything is going to come together when there’s obviously a real chance, for reasons outside your control, it may not... This initial process can be easier for sales people, who are used to asserting reality through storytelling, than for those who, like you, have spent their careers investing. Investors often rely on innate skepticism to see the reality of an investment opportunity clearly.
     
  • One hang-up many analytical analysts launching a fund have is that they feel sales-y and do not like promoting themselves. Try thinking about marketing as telling people an interesting story about the way you see reality, which could be helpful to your audience whether or not they invest.
     
  • Your primary objective should thus be to maintain the right filters for people and ideas so that the delicate ecosystem in your head is as resilient and flexible as possible. That makes good hiring crucial: the people around you will either protect or infringe on the climate within your skull... Beyond deliberately architecting the people who surround you, the best way to control your mindset is to “own” the way you speak to yourself, what sports psychologists call your “self-talk”.
     
  • Another thing that’s hard to own somatically (as opposed to cognitively) in advance is what it feels like to lose money for other people.
     
  • What are you compulsive about? Is it possible to put that at the center of the platform’s activity? I like Josh Waitzkin’s framing of both work and life more generally as an opportunity for self-expression. Ideally this new venture presents an opportunity for you to dial up that self-expression while dialing down activities outside your zone of genius... Embrace your funk... If you can find the thing you do for its own sake, the compulsive piece of your process, and dial that up and up, beyond the imaginary ceiling for that activity you may be creating, my experience is the world comes to you for that thing and you massively outperform the others who don’t actually like hitting that particular ball. I think the rest of career advice is commentary on this essential truth.
     
  • You can denominate energy in any number of forms, money and remaining healthy conscious time on the planet are just two of many currencies. A billion seconds is roughly 31 years. I think Rupert Murdoch or some other aging billionaire might enviously see you as a time billionaire — I imagine he’d pay multiple dollar billions for the next five years of your life if he could magically add your sand to his own hourglass. What price would you sell the next five years to Murdoch for? Stop and actually come up with a true number.
     
  • Tim O’Reilly has a wonderful metaphor for money: he says money is like gasoline while driving across country on a road trip. You never want to run out, but the point of life is not to go on a tour of gas stations.


BLOG POST - Brain Pickings: 13 Life-Learnings from 13 Years of Brain Pickings by Maria Popova - Maria updated an incredibly thoughtful and insightful listicle with a few more important lessons learned.

What do I do now?: Identify a person who magnifies your spirit, but who you need to forgive to let back into your life. Can you forgive them? What do you want to express to them? When is the right time? What emotional price are you excited to pay to have them back in your life?

Complement with 52 key learnings in 52 weeks of 2016 (TD Digest summary).

My highlights:
  • Allow yourself the uncomfortable luxury of changing your mind... it’s infinitely more rewarding to understand than to be right — even if that means changing your mind about a topic, an ideology, or, above all, yourself.
     
  • Do nothing for prestige or status or money or approval alone... Those extrinsic motivators are fine and can feel life-affirming in the moment, but they ultimately don’t make it thrilling to get up in the morning and gratifying to go to sleep at night...
     
  • Build pockets of stillness into your life... The best ideas come to us when we stop actively trying to coax the muse into manifesting and let the fragments of experience float around our unconscious mind in order to click into new combinations.
     
  • ...when people try to tell you who you are, don’t believe them. You are the only custodian of your own integrity, and the assumptions made by those that misunderstand who you are and what you stand for reveal a great deal about them and absolutely nothing about you.
     
  • Seek out what magnifies your spirit... Who are the people, ideas, and books that magnify your spirit? Find them, hold on to them, and visit them often.
     
  • Don’t just resist cynicism — fight it actively. Fight it in yourself, for this ungainly beast lays dormant in each of us, and counter it in those you love and engage with, by modeling its opposite. Cynicism often masquerades as nobler faculties and dispositions, but is categorically inferior.
     
  • Question your maps and models of the universe, both inner and outer, and continually test them against the raw input of reality.
     
  • In any bond of depth and significance, forgive, forgive, forgive. And then forgive again. The richest relationships are lifeboats, but they are also submarines that descend to the darkest and most disquieting places, to the unfathomed trenches of the soul where our deepest shames and foibles and vulnerabilities live, where we are less than we would like to be. Forgiveness is the alchemy by which the shame transforms into the honor and privilege of being invited into another’s darkness and having them witness your own with the undimmed light of love, of sympathy, of nonjudgmental understanding.
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