Helping Boomers Find Purpose & Meaning in Life

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(My dad this summer in Woodstock, NY)

I recently read an excellent essay by Andrew Kortina titled, “They Say the #1 Killer of Old People is Retirement.” In this piece, he discusses the importance of finding purpose and meaning deep into life. Andrew outlines a confluence of factors that are causing mental and financial hardships for baby boomers. Many are struggling emotionally and financially for a variety of reasons including lack of savings, meaningful work and intellectual stimulation. He proposed several interesting solutions based on this simple idea: “I think we can help people continue to feel productive and valued by instilling them with some sense of greater purpose after retirement.” Kortina’s post conjured thoughts and feelings about my father who recently turned seventy-five.

Several years ago, dad was in a tough spot mentally. He had aged out of the workforce and just experienced his second divorce. Additionally, he was living alone for the first time in nearly thirty years. While he had some savings and a predictable income stream from Social Security and an annuity he purchased, this cushion likely wouldn’t be enough if god-forbid there was an emergency or if he is lucky to live beyond his mid-eighties. During this period, my dad would run errands, go to the gym, watch sports and hang around the house on most days. That was his routine. My siblings and I could tell he was depressed, lonely, hopeless and stuck in a vicious cycle.

My dad’s situation isn’t unique. There are more than 70.4 million baby boomers in America according to the U.S. Census Bureau. Workforce participation among boomers is on the decline. Nearly half of boomers haven’t saved for retirement and sixty percent are relying heavily upon Social Security to be their safety net (link). Furthermore, one in seven boomers is treated for depression, which is a higher rate among other generations of American adults (link). Finally, divorce among Boomers is increasing. The number of divorces among that age demo has doubled since the 1990s (link). When looking at the various data points, it turns out that my father isn’t an outlier.

One day last year, I was having a heart-to-heart with my father. We were trying to brainstorm hobbies, odd jobs, volunteer opportunities and local organizations where he could spend his time and perhaps earn a few bucks. I suggested joining the local senior center. That idea didn’t resonate because he still felt young and couldn’t identify with being a senior. We talked about him becoming an usher at Fenway Park since he loves the Red Sox. That likely couldn’t work given the night games and the forty-five minute commute to and from Boston. He suggested working at a friend’s restaurant as a host but they’re only open for dinner. My brothers and sisters also got involved and suggested a bunch of ideas but none seemed to stick.

I felt like we were at a dead end until one afternoon when I was talking with my father about his situation. For some reason in that moment, Viktor Frankl and his seminal book, ‘Man’s Search for Meaning,’ suddenly came to mind. The book chronicles Frankl’s experiences in the Auschwitz concentration camp during World War II, and describes his psychotherapeutic method, Logotherapy, which is founded on the belief that human nature is motivated by the search for a life purpose. Fulfillment achieved through pursuit of meaning in one’s life. Frankl famously wrote, “Everything can be taken from a man but one thing: the last of the human freedoms — to choose one’s attitude in any given set of circumstances, to choose one’s own way.” In that moment, I said to my dad, “You need to find something that will give you purpose and meaning in life.”

Several weeks later, I got a call from him and he sounded upbeat. He proudly announced that he was going to apply to be a substitute teacher in the local area. While my dad was a sales executive for most of his career, he has always had a passion for teaching, coaching and helping youth. I could tell he was excited about this potential opportunity and this could be the solution he and my family had been looking for. He approached the application and interview process as if he was going for a full-time job with a Fortune 500 company. He prepared for hours, gathered strong references and followed up after each of his interviews. He left no stone unturned. It wasn’t very long until he had a job as a substitute teacher in multiple school systems.

Today, my father is a full-time substitute teacher at Salem High School. He loves going to school every day and interacting with the students and the faculty. They challenge him (in a positive way) and help him remain young at heart. No job at the school is above him. He’d mop the floor if they asked him to. He’s contributing in his own way. He’s healthier physically and sharper mentally. He believes he’s making a difference. At age seventy-five, he has managed to find his calling in life. Isn’t that amazing? Most importantly, my dad has finally found meaning and purpose in life. I honestly haven’t seen him this happy and fulfilled in the last twenty years. Every few weeks, my dad will thank me for encouraging him to seek meaning and purpose. The nudge, while simple, was all he needed.

So why did I tell my dad’s story? I feel it’s our generation’s responsibility to help our parents and elders find meaning and purpose should they need a compass. They paved the way for us and now we’re standing on their shoulders. There’s so much we can learn from them. There’s a good chance that we’ll want the same support and guidance from future generations. Helping boomers find a new north star might be one of the biggest untapped opportunities that not enough smart people are focused on. Sure, there might be economic upside in cracking this nut, but I feel there are far larger benefits: less-depression, more quality time with loved ones, better relationships, more independence, healthier bodies and minds, and hopefully longer lives. That seems like a no-brainer to me.

My First Think Week: Going Off The Grid for Exploration and Reflection

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My First Think Week: Going Off The Grid for Exploration and Reflection

Sundown on one of my many nature walks

Earlier this month, my good buddy, Mike Karnjanaprakorn, Founder / CEO of Skillshare, stopped by our place in the Catskills for a few hours. He was just coming off his seventh ‘Think Week.’ Over lunch, Mike explained the inspiration behind this annual ritual and outlined the basic structure he has used over the years. He even wrote a useful blog post about his experience a few days later.

Mike initially got this idea from Bill Gates, who takes these weeks several times a year to find inspiration and go deep into a few areas of interest. Bill would also read a variety of essays and briefs written and submitted by Microsoft employees and researchers. In fact, Bill dedicated one of his Think Weeks in the 90s to understand the coming wave known as the internet (see his memo, “The Internet Tidal Wave”). Several other friends have recently taken a Think Week. This includes Dan Teran from Managed by Q who swore by his experience diving deeply into the future of work.

After talking with Mike and Dan, I decided to plan my own Think Week since I’m in a career transition and likely won’t have much downtime once I decide to go full force into my next endeavor. My first order of business was to block out five days on the calendar. Rather than flying by the seat of my pants once the Think Week kicked off, I dedicated a half a day to develop a list of simple rules, set goals, clean out my Pocket, and select dozens of essays and articles. I reasoned that having structure in place would help me focus and get the most out of my experience.

Putting some simple rules in place was helpful to ensure I created a conducive environment for learning and reflection. Here are the rules that I observed throughout the week. Stick to your themes or areas of interest. Build a firehose of content that aligns with those themes and your overarching goals. Rise by 6:30am and lights out by 11pm. Meditate first thing in the morning. Exercise daily before lunch. Take a walk in the late afternoon. Remove all distracting apps from your devices. Limit Wifi and web browsing. Schedule no meetings. Check email once per day for no more than fifteen minutes. Limit phone calls to no more than two per day. These rules were essential boundaries for keeping my ADHD in check. I recommend you create you own simple rules if you embark on your own version of a Think Week.

Once I had these simple rules in place, I then developed a list of outcomes I was hoping to achieve during the Think Week. The first goal was to develop three personal and three professional goals for the next twelve to fifteen months. The second goal was to determine one focus area for the next twelve to fifteen months so I know exactly how to spend my time. The third goal was to satisfy my intellectual curiosity. The fourth goal was to journal and find inspiration for future blog posts. The fifth and final goal was to take notes on the readings so my learnings were captured.

Finally, I selected a range of subjects that have been top of mind for me lately. I purposefully didn’t choose just one topic because I badly wanted to satisfy my intellectual curiosity and there wasn’t one topic that I felt passionate about. I ultimately decided to spend my time diving into a dozen or so various topics. These included crypto, china, decentralization, philosophy, augmented reality, artificial intelligence, energy, venture capital, investing (broadly speaking), global health, equality and cities.

The week was more challenging than I anticipated. Being up in the woods without any human interaction was probably the hardest part. By the end of each day, I was exhausted mentally from hours of reading and writing. By the end of the week, my brain was fried, I found it difficult to concentrate and I was craving human interaction. On the last day, I slept until 7:30am, relaxed, went for a long bike ride, and reflected on the big questions that were still weighing on me. While I was able accomplish most of my objectives, I wasn’t able to cover as much ground as I thought I would. I still have dozens of unread essays and articles saved in my Pocket. Also, I was reminded that I’m badly addicted to my phone and it’s the biggest productivity killer in my life. While the full experience was enjoyable, it wasn’t as relaxing and easy as I thought it would be.

Despite the challenges, my first Think Week was definitely positive, rewarding and successful. I’m glad that embarked on this journey and invested the time. I now have clarity on how I should spend my time, what I need to say no to, which areas I’d like to further investigate, the changes I’d like to make, and, most importantly, where I’m heading in the next phase of my career. I’ve found that taking a pause and slowing down is necessary for personal and professional growth. The evidence is clear: I’m returning to the city rested and feeling positive about the road ahead. I still have some anxiety about the future but that’s natural. I’m prepared mentally and ready to embrace the uncertainty and risk that lies ahead.

In closing, I highly recommend setting aside some time for a Think Week if you’re looking to go deep in a particular area, facing a big decision and / or experiencing a life transition. Keep in mind it doesn’t need to be a week to reap the rewards. If you’re unable to take a break from work or get away for five to seven days, consider taking a ’Think Weekend’ or ‘Think Day.’ You can also do it anywhere — it doesn’t have to be in the woods — as long as you create an optimal environment for learning and reflection. With enough advance planning, you’ll be able to block out the time, create your own simple rules, build an agenda that fits your schedule, and zero in on the big questions that you’re facing. The idea is to get away, unplug, read, write and focus. You’ll be glad you invested the time and energy in yourself.

Finally, friends and family have asked me to publish a list of the content I consumed throughout the week. While this list isn’t comprehensive, it includes a majority of the articles, research reports, podcasts and videos I found most thought provoking or inspiring. Enjoy!


  • Elon Musk Debuts the Tesla Powerwall (YouTube)
  • The World’s Scariest Drug (Vice)
  • How the Economic Machine Works by Ray Dalio (YouTube)
  • Ray Dalio: How to Build a Company Where the Best Ideas Win (TED)
  • Chefs Table, Dan Barber and Francis Mallmann (Netflix)
  • Brene Brown: The Power of Vulnerability (TED)
  • Zeynap Tufekci: We’re Building a Dystopia Just to Make People Click on Ads (TED)



  • The New Jim Crow: Mass Incarceration in the Age of Colorblindness, Michelle Alexander (Amazon)
  • Freedom from the Known, J. Krishnamurthi (Amazon)
  • Margin of Safety: Risk-Averse Value Investing Strategies for the Thoughtful Investor, Seth Klarman (Amazon)

Annual Letters

  • Jeff Bezos Annual Letter — 1997 and 2017 (Link)
  • Warren Buffett’s Best Investment: The Gates Foundation 2017 Annual Letter (Gates Notes)
  • Berkshire Hathaway 2016 Annual Letter (Berkshire Hathaway)

Technology & Innovation


Artificial Intelligence

Venture Capital

Current Events

  • We Snuck into Seattle’s Super Secret White Nationalist Convention (The Stranger)
  • Where Internet Orders Mean Real Jobs, and New Life for Communities (The NY Times)
  • Undercover with the Alt-Right (The NY Times)


  • Happy Ambition: Striving for Success, Avoiding Status Cocaine, and Prioritizing Happiness (Ben Casnocha Blog)
  • Dalai Lama: Behind Our Anxiety, The Fear of Being Unneeded (The NY Times)
  • Making Major Life Changes (DharmmaWisdom)
  • Bruce Lee on Self-Actualization and the Crucial Difference Between Pride and Self-Esteem (Brainpickings)
  • David Foster Wallace on Writing, Self-Improvement, and How We Become Who We Are (Brainpickings)
  • A Stoic Response to Rejection (The Daily Stoic)
  • The Munger Operating System: How to Live a Life That Really Works (Farnam Street Blog)


  • This is Your Brain on Gluten (The Atlantic)
  • China Signed a $300M Lab-Grown Meat Deal with Israel (Futureism)

The Rise of Cities

Social Justice

  • The Third Rail: In Baltimore, Public Investment — And Disivnestment — in Transportation Have Figured Greatly in the Persistence of Racial and Economic Inequality (The Place)
  • SF Spends a Record $241M on Homeless, Can’t Track Results (SF Chronicle)
  • Fostering Profits: An Investigative Look into the For Profit Foster Home Industry (Buzzfeed)
  • Black Lives Matter is Democracy in Action (The NY Times)
  • The End of Apartheid in South Africa? Not in Economic Terms (The NY Times)
  • Why Every Indiana Inmate Could Soon Have a Tablet (USA Today)



On Privilege

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Last week, I published a blog post titled, ‘Decoding the Qualities of a Great VC.’ The spirit behind the piece was to spark a conversation about what makes a good venture investor and whether that can be predicted. It was generally well received until I saw this Tweet from Nathalie Molina Nino, CEO of BRAVA Investments, an investment platform that cares less about creating the next woman billionaire and instead backs businesses that create wealth for a billion women:

I immediately became defensive because I had good intentions in writing the post and felt I highlighted ‘universal’ attributes of great investors. Without giving it any thought, I quickly replied to Nathalie with the following tweet:

I then felt a backlash from a number of individuals including Katherine Gordon, Founder of The 3% Conference.

At that point, I became uncomfortable because my ignorance was obvious. Growing up in a predominately white upper middle class town in Massachusetts, I was indirectly taught that privilege was about wealth rather than race, gender, sexual preference, etc.. I incorrectly believed I wasn’t privileged because a) I was raised by an amazing single mother who worked two blue-collar jobs, b) I’ve earned an income since my early teens, c) I financed my college education, d) and I’ve worked hard to be self supporting for nearly two decades. It dawned on me through those various exchanges that I have been eating my own bullshit. What I began to quickly realize is that wealth is just one component of privilege and arguably the weakest one.

Later that night, I was talking with my wife, who happens to be Asian American (and more self-aware of her life’s privileges), about the exchange on Twitter. Eliza immediately called me out for lacking empathy and explained that I was wrong on many levels. She pointed out that I’m oblivious because I don’t even see how my own privilege as a white man in America has contributed to my success. Eliza asked me how many opportunities in life I’ve received because I look and talk like those who made the decisions. I didn’t respond to her because I knew the answer. This was difficult to hear and accept because she was right and there was no logical argument that I could make.

Several days later, Nathalie’s tweet and my conversation with Eliza were still weighing on me. I’ve since learned that the idea of privilege dates back to the early 1900s. Famed American civil rights activist W. E. B. Du Bois wrote that although African Americans were conscious of racial discrimination, white Americans did not think much about the effects of racial discrimination. The concept didn’t really enter the mainstream until 1988 when activist Peggy McIntosh published her seminal article, ‘White Privilege and Male Privilege: A Personal Account of Coming to See Correspondences Through Work in Women’s Studies.’ McIntosh describes her understanding of “white privilege” (unearned advantage based on race) which can be observed systemically and individually, like all unearned privileges in society (e.g. privilege related to class, religion, ethnicity, sexual orientation, age, ability).

One year later she published a shorter version titled, ‘White Privilege: Unpacking the Invisible Knapsack.’ These words in particular struck a chord: “After I realized the extent to which men work from a base of unacknowledged privilege, I understood that much of their oppressiveness was unconscious.” In this particular essay, McIntosh outlines twenty-six privileges which she, as a white person, experienced in the United States. Many of them are powerful examples but this one stood out: “If I want to, I can be pretty sure of finding a publisher for this piece on white privilege.” After reading her piece and starting to educate myself, it was impossible to refute that being born white and male and American (the birth luck trifecta!) provides me certain unearned privileges in life that people of other gender and skin colors simply are not afforded.

After I read these essays, I began to contemplate the privileges I experience on a regular basis. Like Peggy McIntosh, I composed a list of these to shed light on what I take for granted. The list included everything from ‘I don’t often think about the personal safety of myself or my loved ones.’ and ‘I don’t have to think twice when asked a question by the police.’ to ‘I don’t have to worry about finding work that is both fulfilling and financially rewarding.’ While I still have much more to contemplate, this exercise has also put things into perspective.

What I’ve also come to understand is these dynamics run DEEP. Really deep. So deep they’ve been systematically engrained into our way of living over hundreds of years. So deep they’re unconsciously programmed into our brains. So deep they perpetuate capitalism, globalization and power. So deep they transcend race, gender religion and national boundaries. In fact, so deep that I’ll likely never understand them regardless how much empathy I develop, how many conversations I have and books I read. These dynamics are extremely powerful, complex and twisted.

Warren Buffett famously said, “I won the ovarian lottery.” So did I. I don’t want this to make me a bad person and I don’t want to feel ashamed. I also don’t want to discount the thousands of hours of hard work I’ve put in over the years. Like others, I don’t know what to feel sometimes. This is very complicated. What I know is this: I have a good heart, an open mind and a desire to expand my worldview. Thankfully, this experience has been humbling and enlightening. I have no doubt it’ll have a lasting impact on me.

In all honesty, I’m still processing all of this and I don’t truly know what I’m talking about yet. I understand this is an awkward conversation and I’m willing to risk saying things incorrectly so I can learn to say them right. I’m certainly open to feedback and criticism. This certainly doesn’t make me special or a hero. I don’t expect a pat on the back. I’m writing this because I believe I need to speak up about this topic and express how I feel. Raising my daily consciousness about the realities of privilege and acknowledging that it’s not an even playing field is an important first step for me.

Finally, I’d like to apologize to Nathalie, Katherine and others for getting defensive about their tweets rather than initially taking a step back and considering their perspective. I’m grateful that these women and my wife forced me to look in the mirror and think about such an crucial topic that’s often swept aside out of habit, ignorance, fear and/or hatred. Thank you for speaking up and challenging me. We need more of this. Not less. I’ll end with this:

“Our lives begin to end the day we become silent about things that matter.” Dr. Martin Luther King Jr.

Decoding the Qualities of a Great VC

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Last Friday, I was talking with Parker Thompson of AngelList and creator of Startup L Jackson about a range of topics from investing in pre-seed companies to building a venture firm from scratch. Towards the end of the call, he asked what I thought are the attributes of a successful VC. Rather than answering on the spot because we were essentially out of time, I told him that I’d give the question more thought and I’d email him my thoughts over the weekend.

Later in the day when I had some downtime, I began to consider Parker’s question and asked myself the following related questions: What makes a good VC? What’s important to venture firms, limited partners and founders? Who are the best VCs and what makes them special? After considering those questions, I grabbed my notebook and wrote down the attributes that I felt were essential.

  • Curiosity — thirst for knowledge and learning.
  • Expertise — business, engineering and/or product chops developed through experience.
  • Passion — genuinely excited by new ideas, innovation and entrepreneurship.
  • Focus — ability to drown out noise and spend time on what matters.
  • Network — authentically develop and maintain relationships at scale.
  • Sales — ability to sell and build consensus internally and externally.
  • Emotional intelligence — empathize and assess motivations, desires, needs and intangibles.
  • Conviction — ability to maintain excitement in the face of opposition and skepticism.

Rather than sending Parker an email with my thoughts, I decided to share the list on Twitter, cc him on the post and participate in the conversation that unfolded. Several founders and investors chimed in publicly and privately to share their views and expand the list I started. While I don’t necessarily agree with all of the suggestions, the other attributes that were mentioned included:

  • Quick learner — ability to quickly consume, learn and absorb information about a wide variety of topics.
  • Friendly — generally pleasant to be around and likable (while I try to respect everyone, I’m not sure this is a prerequisite for being a great investor).
  • 1st principle thinker — someone who can boil complex ideas and phenomena down to their fundamental truths.
  • Stoic — remain calm under pressure and turbulence.
  • Humble — modest in behavior, attitude or spirit.
  • Vision — can see where the world is heading.

This combined list of fourteen attributes is far from comprehensive but I believe it captures many of the important ones. I wonder how the world’s best VCs — investors like Michael Moritz, John Doerr, Marc Andreesen, Shana Fisher, Fred Wilson, Bill Gurley and Chris Sacca — would describe themselves and their most successful peers. I also wonder if their institutions have developed a system to identify the next great generation of investors based on a set of attributes and experiences. Their firms have managed to stay on top for multiple cycles and I don’t think it’s by accident. Given people and networks are at the center of the VC business, perhaps they’ve discovered the hidden answer to the talent equation through identifying, hiring, training and retaining remarkable people.

Several years ago, Jerry Neumann, a respected angel investor in NYC, catalogued the background of every great VC firm’s founders, trying to answer this question. Here is the output from that effort which he titled, VC Genealogy. According to Jerry, the most interesting thing he found is that aside from the expected bankers and lawyers and tech-company execs, there were some journalists in there (Moritz being the most prominent). The qualities of journalists stood out to him because they’re able to track down the right people to interview, ask the right questions, validate the answers they receive and communicate their findings succinctly. Clearly being an effective communicator is critical.

That brings me to the million dollar question: Is it possible to create a platform or system to identify and train the next crop of top venture investors in the world? What would it look like? Perhaps the system is driven by software. Or perhaps it’s a new type of organization in the vein of YC that identifies, trains and networks investors. Maybe it’s a hybrid. I could imagine such a system would score, weigh and rank the candidates based on criteria, attributes and experiences. How would such a program or system grade intangibles or soft skills? Could it identify the power of someone’s network? What are the potential inputs of such a system and what could the output look like? The questions are seemingly endless but it’s a fun thought exercise worth considering.

Maybe this is a pipe dream given there are so few truly great investors and VC is considered to be an apprenticeship business where the learnings take place over many years and throughout cycles. VCs face so many different problems over their careers or even over the course of a portfolio company’s path — that even the best suited have to do a few years of on-the-job learning to be great. Would Fred Wilson be the same investor if he hadn’t experienced the dot com boom and crash at Flatiron Partners? Did Bill Gurley receive years of unique mentorship from the founding partners of Benchmark? What were the key insights Shana Fisher developed while at IAC? Did Michael Moritz discover the ideal founder archetype by writing about Steve Jobs and Lee Iacocca or did he learn from Don Valentine and his predecessors at Sequoia Capital? How did those experiences and interactions shape their investment tastes and philosophies? Given experiences play such an important role in shaping an investor, I’m honestly not sure if it’s even possible to develop a system that delivers alpha by finding and training future investors unless it’s a longer term endeavor.

All that said, experimentation and time will tell us if this is possible. I have a hunch we’ll witness the emergence of a ‘YC for investors’ in the next few years. While venture investors don’t match the speed of innovation as our founder peers, VCs have attempted to create new models and programs over the last few decades. For example, DFJ franchised (brand), 500 franchised (brand), 500 has a VC class (edu), Kauffman Fellows (edu), AngelList syndicates (tech, network), and scouts (network). We’ve seen tech, network, education, and brand as things that people have tried in various combinations to make new VCs. The obvious other options being “hire and train” and “learn on my own dime.” I suspect there’s more to come which is always a good thing.

In closing, I hope any new innovations will be intelligent enough to find the next great VCs based solely on proven attributes and experiences. I also hope these efforts will expand the pool of candidates (think: gender, race, geography). Given the ceiling to break into VC is extraordinarily high — capital, networks, experience, geography — I believe expanding the talent pool would be a good thing for funds and limited partners. That could very well be one of the lasting benefits and contributions these innovations bring to the industry. It’s my hope that in twenty years the list of the great venture capitalists is a diverse set of humans with strong attributes and abilities that have been validated by the giants who helped build the industry.

If you have some thoughts on what makes a great VC and would like to contribute to the discussion, please hop into our thread on Twitter. I’d love to hear from you.

(thanks to Parker Thompson, Jerry Neumann and Leo Polovets for reading an early version of this post) 

10 Days of Silence for a Lifetime of Wisdom

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10 Days of Silence for a Lifetime of Wisdom

Dhamma Dhara, Shelburne Falls, Massachusetts

Three weeks ago, I returned from a 10-day Goenka Vipassana meditation retreat at Dhamma Dara in Shelburne Falls, Massachusetts. Goenka (1924–2013) was a Burmese-Indian teacher of Vipassanā meditation. His teaching was notable for emphasizing that the Buddha’s path to liberation was non-sectarian, universal, and scientific in character. He became an influential teacher and established meditation centers, like the one I attended in the Berkshires, all over the world.

S. N. Goenka

My time at Dhamma Dara was easily one of the most brutal and intense yet profound and rewarding experiences in my life. When I signed up, I didn’t expect the retreat would help me solve my problems or discover my purpose in life. My goal going into the course was simply to gain a greater appreciation and understanding of my mind. However, I walked away experiencing and learning so much more. I didn’t fully appreciate how intertwined our minds, emotions and bodies truly are.

So what exactly is Vipassana? The Vipassana philosophy is built around a technique of meditation focusing on the breath and self observation of the sensations on the body. It’s a method of ‘mental purification’ which allows one to face life’s tensions and problems in a calm, balanced way. Vipassana aims to eliminate the three causes of all unhappiness: craving, aversion and ignorance. With continued practice, the meditation releases the tensions developed in everyday life, dissolving the knots formed by our habit of reacting in an unbalanced way to pleasant and unpleasant situations. Although Vipassana was developed as a technique by the Buddha, its practice is not limited to Buddhists. In order to penetrate the deepest levels of the unconscious mind and heal our complexes, students are expected to work diligently and observe the code of discipline prescribed by Goenka.

During the ten days, we were stripped of all conveniences and comforts. We also had to abstain from any unwholesome behaviors. Before the course, all students agreed to abstain from killing, stealing, engaging in sexual activity, telling lies, consuming intoxicants, eating after noon, engaging in sensual entertainment, wearing revealing or fancy clothing, and sleeping on luxurious beds. Additionally, we agreed to practice the technique taught by Goenka, observe noble silence (read: no verbal or non-verbal communication), adhere to separation of genders, and limit physical exercise to walking. Finally, we had to turn in our devices, books and journals before the course kicked off. Simply put: all distractions were removed. The purpose of the code of discipline isn’t to punish but rather to create the optimal environment and frame of mind for meditation. I was excited to unplug but also a bit anxious.

For ten days, we followed a super rigid and strict schedule.

Source: Sophia Ciocca

That was our routine each day with few variations. We practiced nearly a hundred hours of meditation while on retreat. During our limited breaks, we were able to eat (breakfast and lunch), walk the grounds, wash up, think or rest. That’s really all we could do when we had downtime. The only other ‘escape’ was an evening video discourse from Goenka. During these hour-long lectures, Goenka shared the philosophy behind Vipassana, previewed what’s to come the next day and provided actionable insight about the practice. As you can probably tell from the schedule and the code of discipline, there wasn’t much about this ‘retreat’ that was relaxing or fun.

For the first three and a half days, we engaged in ‘Anapana’ meditation. Anapana means ‘mindfulness of breathing.’ The technique is simple but challenging: concentrate on nothing but inhales and exhales. When the mind wanders simply return to the breath. This form of meditation sharpens the mind and develops the concentration required for Vipassana. The first three days were physically brutal. My knees, hips, back and neck were sore from sitting on a cushion with no back support. But by the end of the third day, my mind was beginning to quiet and I was experiencing extremely subtle and gross sensations inside and around my nose and upper lip. Sensations such as heat, cold, itching, tingling, pain, blockage, throbbing, hardness and softness. Once I could feel that my mind was sharpening and sense subtle sensations, I knew we were ready to begin practicing Vipassana.

Vipassana means ‘insight’ or ‘clear seeing.’ On the forth day, we were instructed to expand our awareness from the nose to the entire body by using a body scanning technique that stresses developing a heightened sensitivity to a variety of gross and subtle sensations such as the ones I mentioned above. The technique prescribes starting at the top of the head and scanning every body part down to the toes. Once we reached the tips of the toes, we calmly scanned the entire body back to the top of the head. Over and over and over for six days.

As sensations surfaced, pleasant or unpleasant, we were instructed to note them and remain equanimous (not good, not bad, it is what it is). Throughout the retreat, Goenka reminded us not to judge, oppose or cling to any of the sensations. By removing emotions and feelings from bodily sensations, the ego begins to dissolve and we begin to remove the underlying causes of craving and aversion.

By day six, I had reached an altered state of consciousness unlike anything I’ve ever experienced outside of limited experimentation with hallucinogens in college. I became so in tune with my body and mind that I could feel both pleasant and unpleasant sensations from my head to toes and even deep inside my body. Some pains and cramps were so intense that I had to learn how to develop equanimity which wasn’t in my vocabulary before the retreat. I completely underestimated the power and physical intensity of the Vipassana technique.

By the seventh day, I was telling myself that I wish I had ‘read the label’ and done more homework about the technique and its effects. I was obviously past the point of no return but was overwhelmed by the intensity of the sensations. I even went to the teacher at one point and asked him how I could ‘turn down the heat.’ Throughout the last few days, I experienced chest and abdomen pain that I used to suffer from many years ago. I was clearly deep into my subconscious and the meditation caused it to resurface. The practiced forced me to deal with the root causes of the issue — mainly stress and anxiety related to childhood and adolescence.

By the end of the retreat, I was able to sit with these painful sensations, observe them and literally feel them dissolve inside of me. I was also able to sit for hours without moving or feeling much structural pain. The mind body connection is incredible. I was healing myself by focusing on and accepting these physical pains that I’ve been afraid of for more than a decade. Instead of running, I had no choice but to surrender and in many ways kill my ego. In retrospect, that was the obvious solution but it took me ten days to figure it out for myself. In some ways, I felt like performed surgery on my mind and body. It was a surreal and deeply moving experience. Thankfully, I was able to face some deeply rooted and underlying issues that had been bothering me for nearly two decades.

About midway through the tenth day, noble silence was lifted and we were able to communicate with the other students. This helped ease us back into reality. I found it really valuable because I was able to hear about other’s experiences and begin to process my own. One conversation in particular was very helpful. I had told one of the participants that I was ‘penetrating and attacking my pain’ over the last few days in an attempt to fix myself. She got emotional and tears welled in her eyes. She responded, “Don’t say that. You should never attack yourself. You’re healing yourself through self care.’ That one comment was incredibly helpful and really helped put the entire experience in perspective. I dedicated the remainder of the last day and my final meditations to self love and self care. That’s the piece of the puzzle that I was missing. At that point, I knew that I received what I came for. I was ready to go home.

Despite being home for three weeks, I’m still processing my time at Dharma Dhara. I expect that it will take a few months to fully appreciate and internalize what I learned about my mind, body, spirit and ego. Maintaining an hour of meditation each day is certainly helping me go deeper and unlock a sense of awareness I never thought was possible. As I anticipated when I signed up for the course, my problems haven’t disappeared and I didn’t find my purpose in life. But I’ve emerged stronger, calmer, more patient and more resilient. I also feel way more present so I can be in service of and available for others. Best of all, I now believe I can tackle any challenge and find equanimity in good situations and bad. While I’m just starting on the path, I’m enjoying the moment and the process.

In Closing: Lessons & Learnings

When I returned home, I wrote for a few hours to capture the essence of my experience at Dhamma Dhara. I noted everything from the food to all the business ideas I dreamed up. One of the sections was ‘Lessons and Learnings.’ I’ll leave you with what I jotted down that afternoon. If any of these ideas or my experience resonates with you, I’d be honored to hear from you. Without further ado:

The 10 days were the equivalent of 10 years of life lessons and therapy.

Everything rises and passes. It’s a law of nature. Change is constant around us and within us.

Craving, aversion and ignorance are the roots of all issues and lead to suffering.

The world doesn’t stop for you when you’re away or offline. It just keeps moving.

The mind, emotion body connection is more accessible and far deeper than you believe.

Changes often provide temporary relief but pain and suffering always returns.

The mind wants to take us into the past or the future with pleasant or unpleasant thoughts. Remaining in the present is reality so embrace it.

Don’t trust all of your feelings and snap judgements towards people. We’re very good at crafting stories and beliefs in our minds with very little context.

Nothing is more sacred and precious than family and friends.

Developing a sincere desire for all beings to be happy is incredibly powerful and liberating.

We can survive on far less comfort and food than we’re used to.

Consume enough to sustain but not more.

Limit waste and embrace conservation.

Don’t force things. Apply the right amount of effort but not too much.

Take and consume only what you truly need. Not more.

Humans are far more resilient and adaptive than we believe.

We can heal ourselves mentally and physically using mindfulness and meditation. It just takes commitment and an investment of time and energy.

You can learn the basics of anything if you dedicate 100 hours over a few weeks. Immersion and focus generate results.

Find appreciation in the mundane.

These four words repeated over and over can get you through anything: patience, persistence, awareness, equanimity.

Most pain is a function of the mind and created by feelings such as anxiety and fear.

Sitting with both physical and mental pain for long periods of time is strangely liberating and builds resiliency.

Our bodies adapt to changing stimulus far more quickly than most believe.

Our capacity to deal with emotional and physical pain is far greater than we believe.

The only person you can change is yourself. When others notice your changes, it might give them the courage or the reason to change themselves.

Perception is powerful .You often see only what you want to believe.

Pause before speaking or acting. Sometimes you’ll change your approach with just a bit of time and reflection.

The more emotional and physical pain that is suppressed, the deeper it’s driven into our subconscious and bodies.

Be mindful anytime you use the words me, mine, my, I. They signal attachment.

We are a collection of dualities (love vs hate, joy vs pain, happy vs sad, comfortable and uncomfortable, etc.)

Love yourself. Focus on self care.

The subconscious is very accessible.

Expectations set us up for clinging and disappointment.

Equanimity isn’t suppression of thoughts or feelings but being ok with how a situation unfolds or how we feel in a given moment.

Spending time alone is very underrated.

Creating time and space to process is essential for the spirit.

Be kind to others. Goodness is contagious. Life is too short to be mean.


Hug O’ War

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Last weekend, I was hanging out at my twin brother’s house. It was early in the morning and wanted to kill some time so I decided to browse his vast book collection. I came across one of our most cherished books from childhood, Where The Sidewalk Ends by the legendary artist and writer Shel Silverstein. As I was flipping through the book, I arrived at one of my favorite poems, Hug O’ War: 


I immediately Google’d Hug O’ War to learn more about what inspired Shel to write the poem. I discovered that he wrote it to widely express nonviolence and goodness to the world.  That expression really resonated with me. As I reflected on the poem, the words non-violence, cooperation, winning, surrender, love, happiness and goodness kept coming up for me. I felt those words accurately represent what I value as a human being.

Yesterday, I walked into a tattoo parlor near Chinatown in San Francisco and had Shel’s Hug O’ War illustration etched on the back my arm. My hope is that it’ll serve as a reminder to always love, support, serve and cooperate rather than to fight, harm or hurt.

Here’s to filling the world with more kindness. I can’t think of a better purpose than that.


Introducing Huddle: Peer-to-Peer Support Groups for the Masses

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Everyone struggles with something. For me, it was anxiety, addiction and imposter syndrome. For a long time, I was afraid to seek help because I was worried about what others would think of me and how they’d react since I was extremely functional in all facets of my life. I ultimately healed myself and transformed my life over several years through mediation, nurtrition, radical candor, sleep, exercise and positivity. I also turned to a variety of support communities which were a huge source of strength, meaningful relationships and perspective. I credit much of my transformation to these groups. There’s no way I could have improved my mental health all by myself.

That’s why I was excited to meet Tyler Faux and Dan Blackman of Huddle. They shared their plans to build a video-based peer-to-peer support network and change how the world communicates about mental health issues. They explained their product would have public and private channels for people to engage about the things in life they are dealing with. They also explained, that Huddle will allow people to be anonymous or themselves so they can engage however they’re most comfortable. In that moment, I wished I had access to this product many years ago when I struggling but wanted help. I was also captivated by their mission of breaking down conventional perspectives of how people are supposed to get help by creating a community of real people, talking about real things, supporting one another.

As they were describing their product and vision, I believed millions of people would potentially see the value in a digital peer-to-peer support network. Support groups are incredibly effective but haven’t evolved in decades. There are more than 500,000 offline support groups in the U.S. alone. At any given time, more than 6.5 million Americans engage in these groups. They have numerous benefits including accountability, perspective, community, emotional support, service, mentorship and empowerment. Despite these benefits, support groups today tend to be antiquated, fragmented, geographically limited, infrequent, offline, stigmatized and difficult to discover. That’s why I felt there was a real need to modernize these therapeutic communities.

Support groups exist for good reason. 44 million Americans struggled with mental illness in 2016 but more than 60% didn’t seek treatment. That doesn’t even include those who are impacted such as family, friends and co-workers. People seek help for many life situations such as addiction, depression, death, illness, PTSD, body image, eating disorders, obesity, divorce and many more. The more I thought about the problem and the need, Huddle seemed to be a potentially appealing solution that could transcend race, religion, ethnicity, socioeconomic status and boarders.

And let’s be honest: traditional social media isn’t helping this problem. In fact, one could make the argument that networks like Facebook are only making the problem worse despite their best efforts. Additionally, most people aren’t comfortable broadcasting their problems to family, friends and co-workers due to stigma, fear of being judged and potential negative consequences both personally and professionally. One could also make the argument, that people aren’t comfortable seeing other’s struggles in their social feeds. A void seems to exist in the world.

That’s why I’m thrilled to share that Huddle is now a reality. I’m also thrilled to share that I’ll be playing a small role in the company as an advisor. As you can probably tell, mental health is an incredibly important cause for me and I believe that digital tools like Huddle can be a significant part of the solution. The app launches today so anyone with an iPhone can join the community, get strength from others or lend your support to those in need. You can download it here. While the community is just getting started, I believe digital peer-to-peer support groups will be the norm in the next decade.

Life is hard, messy and unpredictable. Every single one of us or people that we love are struggling with something whether it’s depression, divorce, anxiety, addiction, fear, anger, resentment and / or imposter syndrome. Instead of grandstanding on social media (of which I’m guilty of myself), why not embrace our imperfections? Why not start an internal or external dialogue about what’s really going on in our lives. The impact would be massive. Here’s a big secret: when you speak openly about your challenges it gives others the strength to do the same. I realize it’s frightening but the rewards are boundless. We can start to relate to one another. We can support each other. We can heal each other. That to me is way more powerful and beautiful than pretending everything is perfect.