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Oh, hey, what's up! Welcome to this week's digest. This is a very special 'Experiment' edition. I am sharing the results of two meaningful personal experiments, as well as a variety of content that encourages us to experiment with our ideas and ways of being to get feedback from the world.


Experiment #1 - Coaching: Over the last few months, I coached three pilot clients on health behavior change (weight loss), career path & professional growth, and prioritization & focus (while building a company and a family), respectively. The two questions I wanted to answer were: (1) Can my coaching create significant value for others? (2) Do I enjoy coaching? The answer to both questions was a resounding Yes! (NPS of 67!! Though it wasn't as much like Rocky IV as I expected... definitely less running in the Russian woods and rock lifting). The experience was scary and hard in some ways, and preposterously fun and meaningful and easy in other ways. Ultimately, I didn't know what it was really like until I put myself out there. Because of the positive outcomes, I am now sharing my coaching more broadly and professionalizing it! More on that on my website and below in Blatant Self-Promotion.

Experiment #2 - Stand-up Comedy: Last Saturday, I performed stand-up comedy for the first time!! It was an open mic in Santa Monica, ended up doing three minutes for ~50 people (mostly jaded open-mic'ers). This has been a dream of mine for a long time - I am a huge comedy nerd, and have deep respect and appreciation for the art created by other comedians. Despite weeks of preparation and general excitement, I was SO scared in the hours and moments leading up to it, reminiscent of standing on the ledge right before my first bungee jump. It was amazing how many bullshit stories my mind concocted to try to get me to not do this. But I decided to keep taking positive steps towards the experience. And then in the moment, it all kind of just happened. My practice kicked in, I was focused on delivering my material, and the time flew by. Before I knew it, I got 'the light' (the signal my time was up), and walked off-stage. I don't even know if there were any laughs, groans, or any reactions from the audience... I was so dialed-in and the adrenaline was pumping so hard (pretty sure I got one strong chuckle :D). My performance was nowhere near where I want it to be... and I am quite proud of myself for facing down the fear and just doing it, finally putting in the work that needs to be done to improve my game.

This week's topics include embracing presence, self-reflection, pain, conflict, and uncertainty for personal growth. Enjoy!

 
If you like this digest, please consider sharing with friends, making the winning header, and / or curling a penalty kick. xoxoxo <3
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TDD TL;DR
QUOTE OF THE WEEK
 
"The desire for safety stands against every great and noble enterprise" ~ Tacitus
LETTERS TO THE EDITOR (AKA I have a lot to learn from you)

AJ, replying to Fuck Yes or No
: This quote is very gratifying: “Remember, it’s your job to look for something cool in everyone you meet; it’s not their job to show you. This is life, not a fucking sales convention. Learning to appreciate people you meet is a skill you cultivate.” I’m glad he allows for the importance being a good human being as well! The concept at its face value seems highly selfish, but that’s my own poor reading of it the first time around, maybe. ... And also - WHY IS THIS DIGEST NOT CALLED TEDDYGRAMS???

This is probably my favorite quote from Mark's whole article, AJ! And yeah, at face value, mental models like this can seem quite selfish, but they ultimately lead to relationships that are deeper, more meaningful, and, most importantly, reciprocally life-giving. When we do something because we are Fuck Yes about it, as compared to doing it out of a sense of obligation, we often invest a much better version of ourselves into the experience.
BLATANT SELF-PROMOTION - LAUNCHING MY COACHING PROGRAMS

TL;DR: After a successful pilot, I am launching my coaching programs! The gist of my coaching programs is 'Solutions-oriented coaching to clarify your vision and design systems that empower you to realize it'. To start, there are four coaching slots available, for 8 or 16 week programs. Apply here for an intro call. More information is available on my website, and below. Or simply reply to this e-mail with any questions! Referrals are always greatly appreciated.

Pilot Learning: My #1 takeaway from the coaching pilot is that if a client simply feels comfortable enough to openly talk at me for an hour about their #1 challenge, they will make meaningful progress. When I add in a few thoughtful questions, or share a relevant resource on the subject, or push their thinking from an alternative perspective, my clients make even more progress. This is not rocket science, but it does take significant patience and curiosity to truly be there for someone, especially working through something deeply important and challenging to them. We often already have the answer inside, at least the kernel of it. But we need to actually spend the time focused on our challenge, and it helps tremendously to get out of our heads and see the challenge from an objective, external perspective.

Client Testimonials

Nick, coached on health behavior change (weight loss): "Teddy is a great coach, mentor, and friend. He helped me move forward on my self-improvement goals in a way that I had long been struggling to do on my own. In particular, he helped me evaluate and shift how I make daily decisions about nutrition and exercise, and ultimately has put me on a better path toward achieving my health and wellness goals. Perhaps even more importantly, Teddy empowered me with knowledge and tools that will enable to be more effective at changing my habits and behavior in all areas of my life. "

Chris, coached on career path & professional growth: "Teddy was someone I could open up to about my challenges. He actually cared about my progress and was invested in the outcome. He was always available and willing to answer any questions I had, which I found helpful as I worked through the "homework". Finally, I ended up getting exactly what I wanted out of the coaching experience - a framework I will use to improve professionally."

Sean, coached on prioritization & focus while building a company and a family: "Teddy was a great source of insight and help on a range of issues, from the humdrum daily to-do-list to the audacious life goals.  He provides energy, encouragement, accountability, and wisdom, along with a great framework and some really helpful tools.  I have adopted a number of Teddy's recommendations and have much greater confidence that I am making progress.  For the first time in a long while, I feel as though I am moving in a productive direction."

Example Client Situations
  • You are making a major crossroads decision like career path, graduate school, or relationship.
  • You want to create more time and attention for the activities and people that matter most to you.
  • You aspire to cultivate new health & wellness habits.
  • You desire a more concrete purpose or vision for how you want your life to be.
  • You feel a mounting discontentment despite all of the hard work and effort you pour into your life.

Programs are 8 or 16 weeks, with bi-weekly coaching sessions and assignments in between sessions. Programs cost $1400 (8 weeks) or $2000 (16 weeks).

If you want one of the four coaching slots, apply here for an intro call! For more information, please see my website, or simply reply to this e-mail with any questions!
BEST OF WHAT I CONSUMED THIS WEEK

BOOK
- A New Earth by Eckhart Tolle (My full Kindle highlights) - This book was sitting on my reading list for eons. I was initially hesitant because Eckhart's other book, The Power of Now, seemed ~20% incredible, but ~80% magical rambling. Also, Eckhart's work basically takes standard Buddhist principles and adds his spin. The trend continued with this follow-up. For all that there is to dismiss in this book, there is ~10-20% that is really worth considering and embracing, if only as a fun twist and re-examination of Buddhism's core 'noble truths'.

My highlights:
  • As we no longer identify with our mental positions, we are able to be tolerant of other people’s beliefs and perspectives. We can temporarily shift our own perspective and see things through their eyes.
     
  • The quicker you are in attaching verbal or mental labels to things, people, or situations, the more shallow and lifeless your reality becomes, and the more deadened you become to reality, the miracle of life that continuously unfolds within and around you. In this way, cleverness may be gained, but wisdom is lost, and so are joy, love, creativity, and aliveness.
     
  • Most egos have conflicting wants. They want different things at different times or may not even know what they want except that they don’t want what is: the present moment. Unease, restlessness, boredom, anxiety, dissatisfaction, are the result of unfulfilled wanting.
     
  • The underlying emotion that governs all the activity of the ego is fear. The fear of being nobody, the fear of nonexistence, the fear of death. All its activities are ultimately designed to eliminate this fear, but the most the ego can ever do is to cover it up temporarily... Once you realize and accept that all structures (forms) are unstable, even the seemingly solid material ones, peace arises within you.
     
  • Resistance makes the world and the things of the world appear more real, more solid, and more lasting than they are, including your own form identity, the ego. It endows the world and the ego with a heaviness and an absolute importance that makes you take yourself and the world very seriously... The affluent world is even more deeply identified with form, more lost in content, more trapped in ego.
     
  • Nonresistance, nonjudgment, and nonattachment are the three aspects of true freedom and enlightened living.
     
  • The Roman philosopher Tacitus rightly observed that “the desire for safety stands against every great and noble enterprise.” If uncertainty is unacceptable to you, it turns into fear. If it is perfectly acceptable, it turns into increased aliveness, alertness, and creativity.


BLOG POST - Farnam Street: Pain Plus Reflection Equals Progress by Shane Parrish - Shane's thoughtful summary of Ray Dalio's key principles for learning and growth. We have to be willing to not only expose ourselves to pain and failure, but also really reflect on it, to fully learn from our mistakes and realize our growth potential. If we maintain a fixed mindset about ourselves, 'I am this way', then it is more tempting to opt for beautiful delusion about how the world really works. If we adopt a more fluid mindset about ourselves, then we can have the confidence to be able to adapt to whatever we learn through our experimentation, success, and failure.

My highlights:
  • Our painful moments are important moments. When we confront something painful, we are left with a choice between an ugly and painful truth or a beautiful delusion. Many of us opt for the latter and it slows our progress.
     
  • Being open about weaknesses means being open about who we are in the moment. It doesn’t mean that’s who we are forever. But we can’t improve what we can’t see.
     
  • The easy path means being the same person you were yesterday... The harder path is to embrace the pain and ask yourself what you could have done differently or better or what your blind spot was.


BLOG POST - Medium: How is your conflict affinity? by Amar Singh - Amar's work helps us see and embrace the myriad benefits of conflict. So many important points baked into one simple blog post. Most important for me were: 1) Charity / steel-manning your 'opposition'; 2) The importance of being open and honest at work (I term it 'uninhibited'), where we spend a lot of our lives.

My highlights:
  • Conflict is often helpful; we should aspire to become better at it. We should be able to disagree and argue in search of truth, while avoiding the negative side-effects that are often associated with conflict.
     
  • Be vigilant about creating an environment where everyone’s opinions are valued and no one is denigrated or punished for dissent.
     
  • The best way to argue kindly is take on your opponent's strongest arguments, not their weakest ones. This is referred to as steel-manning an argument.
     
  • ...one of the kindest things you can do for another human is giving respectful, honest feedback... This is likely the hardest hurdle in the path to having better conflict — but definitely achievable with kindness, empathy and respect.
     
  • Regardless of what we discover, we understand and truly believe that everyone did the best job they could, given what they knew at the time, their skills and abilities, the resources available, and the situation at hand.
     
  • "...my work is my life. I spend the majority of my time working. Most of my friends I know through work. If I can’t be open and honest at work, then I’m not really living, am I?’’
MOST FAVORITE FROM THE PAST

BOOK
- Living Beautifully with Uncertainty and Change by Pema Chodron (My full highlights) - I first read Pema's work at a time of great uncertainty in my life, when I was job hunting after graduating from Wharton in summer 2016. Her work resonates strongly with me because of my old mindset, that I wouldn't be happy until I checked certain boxes and felt stable. By embracing the inherent uncertainty in our lives, it becomes easier to be present and happy in the moment, regardless of how that moment is or the meanings we have layered onto it.

My highlights:
  • The very nature of our existence is forever in flux…Our attempts to find lasting pleasure, lasting security, are at odds with the fact that we’re part of a dynamic system in which everything and everyone is in process.
     
  • When we resist change, it’s called suffering. But when we completely let go and not struggle against it, when we can embrace the groundlessness of our situation and relax into its dynamic quality, that’s called enlightenment… Another word for this is freedom – freedom from struggling against the fundamental ambiguity of being human.
     
  • We have an urge to find relief from anxious feelings by clinging to something that gives us pleasure… We turn to anything to relieve the discomfort – food, alcohol, sex…
     
  • We have a choice. We can spend our whole life suffering because we can’t relax with how things really are, or we can relax and embrace the open-endedness of the human situation, which is fresh, unfixed, unbiased.
     
  • I can’t overestimate the importance of accepting ourselves exactly as we are right now, not as we wish we were or think we ought to be.
     
  • What most of us have been doing is gearing our lives toward avoiding unpleasant feelings while clinging to whatever we think will make us feel good and feel secure. From a conventional point of view, this makes perfect sense. But from the vantage point of remaining with our direct experience, the vantage point of opening to the tentativeness of life, this strategy is self-defeating, the very thing that keeps us stuck.
     
  • We can follow Chögyam Trungpa’s suggestion: Live your life as an experiment. Adopt an attitude of “I’m not sure what will help in this situation, but I’m going to experiment and try this.”
     
  • We live in a world that is intrinsically good, intrinsically awake, and our path is to realize this. Simply put, the practice at this stage is to turn toward your experience, all of it, and never turn away.
     
  • As Leonard Cohen once said about the benefits of meditation, “The less there was of me, the happier I got.”
     
  • Knowing that it’s all passing so quickly makes everything I encounter exceedingly precious… We’re no longer looking for something other than right now, no longer looking for an ideal world.
     
  • We need to help each other let go of the shore and stay in the middle of the river with no life jackets, no inner tubes, and no intention of ever clinging to anything again.
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