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Reflections: This is 32

I started a blog, in large part, because I was interested in tracking my evolution and understanding my own patterns. Birthdays seem like the perfect juncture to reflect on the past year. Since I don’t have an entry to reflect on from 2019, I’m going to answer some of the questions I’d like to ask my thirty one-year old self.

What’s Work Like?


I really wish I had documented my thoughts, fears, and projects about work last year. Though I remained optimistic, we've gone through some really tough financial times. September 2019 was the worst month in Green Hill’s history and there wasn't much runway for the operation to get off the ground. I bought my co-founder’s shares in April, on the heels of our first quarter in the black. Over the next few months, I made a number of changes that I considered necessary but in conflict with our short-term financial interests. My long-term orientation towards building a values-based, mission-driven company seemed idealistic and I had serious doubts about our financial viability. Since then, things have improved dramatically and below are some of the accomplishments from the past twelve months.

  • Purchase of Van Dyke Apartments: Last October we closed on a six-unit apartment building in Raleigh. This was my first professional real estate transaction and I certainly learned a lot (i.e., if it is a straightforward transaction, get a fixed rate when working with an attorney). I favor a business model in which we own the real estate used by the operating company, though it’s not always possible or practicable.

  • Joint Commission Accreditation: Green Hill received its accreditation by the Joint Commission last December. Our business model relies heavily on private pay services as opposed to insurance reimbursement and I have worried that a recession could have extremely negative ramifications on our financial situation. To de-risk our position, I believe that it’s prudent to diversify our revenue through contracting with insurance companies. Joint Commission accreditation was the first step in that multi-year process.

  • Insurance Contracting: We began the process of contracting with insurance companies earlier this year. Our goal is to be in-network with the major insurance providers by the end of the year and some contracts have already gone in effect. Half of our services are in-network with BCBS, our entire offering will be in-network with Aetna in less than a month, and we hope to finish contracting with BCBS, Beacon, Anthem, and Humana by the end of the year.

  • Launching Community Outpatient: We launched an outpatient program that serves the local community last November. I would argue that quality, affordable outpatient treatment is what’s needed most in our field. Adding an entirely separate line of service accomplished two main aims (1) serving the local community by providing quality, affordable treatment and (2) diversifying our revenue streams. This was another step in creating an anti-fragile company.

  • Purchase of Office Building (Closing October 2020): After nine months of searching, we’ve finally found a new office. Searching for an office tested my patience on a number of occasions and I'm grateful that we're in a position to purchase Green Hill's "forever home." Our new office will allow us to grow considerably while increasing the value proposition to our clients, as it will have a yoga and meditation studio, audio/visual studio, and academic space. If we had settled for a less-than-ideal solution due to haste, we would have really missed out.

  • Doubled Clinical Staffing: Over the past year we’ve more than doubled our clinical staffing. I’ve tended to over staff Green Hill but that’s a risk that’s been successfully navigated thus far.

  • Tripled Census: Since last September, we’ve more than tripled our total census, thanks in large part to the outpatient line of service. We’re continuing to improve our value proposition to clients and their families through updated curriculum, expanded family programming, and a host of other initiatives that are in the early stages of development.

  • Financial Stability: We’re in the best position we’ve ever been but I’m frequently fearful that we’re in for a significant downturn. As mentioned a few times above, I’ve taken a number of steps to make our organization anti-fragile but too often things feel tenuous. Over the next few months I hope to learn to trust my decision making and the team’s ability to perform -- finishing up a few more insurance contracts should also help.

My identity was way too enmeshed with the financial results of Green Hill, it’s hard not to be when the vast majority of your net worth is tied up in one investment. I’ve learned a few lessons from the experience of last year: (1) use inversion to avoid catastrophic mistakes, (2) don’t risk everything in one venture, and (3) build a network that refuses to let you fail.



How's Your Relationship?


The best decision I’ve made in the past few years has been to build a life with my fiance, Kelsey. We started dating just over three years ago and after a year of Boston-Raleigh distance, she moved to North Carolina. We lived in an apartment in downtown Raleigh for the first year and then we bought a house in Chapel Hill so she could be closer to school (that mattered in the pre-coronavirus days). In the last year we’ve each worked incredibly hard professionally and we’ve also done a lot of meaningful work as it relates to living together -- I’ve probably had to do most of the actual “work”.

  • Family: Maybe it’s because I’m an only child and thus my nuclear family largely focused on my activities growing up, but I haven’t cared much for family events and staying in touch. This year I have started to really appreciate my parents, extended family, and soon-to-be in-laws. I feel fortunate to have learned this lesson, though it probably should have been learned much earlier.

  • The Small Stuff: My life is really great but if Kelsey didn’t slow me down to smell the proverbial roses, I’d probably fail to notice how lucky I am. When I take the time to slow down, I recognize my life is almost perfect; however, if I’m caught up in my thoughts about the future, I’m not afforded the opportunity to enjoy the richness of my life. Kelsey has (extremely patiently) steered me towards savoring the little things in life.

  • Intellectual Challenge: There is no doubt that my fiance is the brains of the operation. I feel fortunate to be building a life with someone who is typically a few steps ahead. Though our professional goals and intellectual interests are quite different, Kelsey is always able to improve my thinking and understanding. It can be a little frustrating when my hard-won understanding and knowledge seems to come intuitively to her but at the end of the day, I’m happy to marry up.

  • Unwavering Support: More than anything, I am starting to understand what it means to feel unconditional love and support. Though my parents always did a great job in this arena, I don't think I knew how much it mattered. Regardless of the challenges I face, I'm thankful to have a fiance who supports me without pretext.

I can't overstate the importance of building a life with someone who challenges you. It's hard to imagine life doesn't turn out well if you surround yourself with top-notch people.

What's Your Spiritual Life Like?


For me, this is perhaps the most interesting section. I’ve always felt like I was searching for an answer that was just out of reach -- if only I meditated enough, practiced yoga enough, or read enough, the answer would appear and there would be no more searching. Now, though meditation, yoga, and self-study are significant parts of my life, I'm not looking "out there" for some special state or knowledge to attain.

  • Understanding of Self: Instead of looking for some mystical state of being or an intellectual answer, I’m trying to loosen the stranglehold I've got on my identity, my sense of self. Much of my life has been about ego-strengthening activities -- trying to improve myself as a business person, fiance, leader, spiritual seeker, etc. At this point, I believe that the real work is to release the various, often competing, identities and focus on being rather than becoming a more integrated whole.

  • Meditation: My practice is not as dogmatic as it was earlier in the year and while I do like to spend about an hour in meditation, I’ve lost the notion that I need to dedicate a certain amount of time for activities that are somehow “spiritual” in nature. Much of my work is about eliminating concepts which means the false distinction between “spiritual” and “worldly” pursuits must be discarded.

  • Yoga: After about two years of inconsistent practice, I recommitted myself to daily ashtanga vinyasa. Seated meditation was the bulk of my spiritual practice the past couple of years and yoga was more of an adjunct. If I had to give up asana practice or seated meditation, I’d give up asana practice; however, I’ve discovered that asana practice is good for me and it can be a part of my life without being all encompassing. A daily yoga practice provides two distinct benefits: (1) more time in silence and (2) regular exercise.

A lot of my spiritual practice is centered on not identifying with some sort of self-concept, even a spiritual one. As Michael Singer put in his book, The Surrender Experiment, “Life was making me let go of my spiritual self-concept, and i was staying very conscious about not replacing it with yet another.” Here’s to being more and thinking less.



What are Your Intellectual Interests?


Human Flourishing: I’ve come to view the personal pursuit of human flourishing as a two-pronged track. On one track you’ve got self-improvement projects -- the things you do to become more effective in one of your roles/identities (entrepreneur, leader, teacher, partner, etc.). On the other track you’ve got the self-realization project -- the things you do to grapple with existential questions. For me, these dual tracks have typically seemed in conflict with one another; however, that’s starting to shift. Just as I want to eliminate the distinction between worldly and spiritual pursuits, I am working to eliminate the perceived dichotomy between self-improvement and self-realization. I’m guessing that all future professional pursuits will fall under the umbrella of “ventures that promote human flourishing.”


Mental Models: Ever since I stumbled upon the Farnam Street Blog about a year ago, I’ve been obsessed with learning and deliberately employing mental models. “A mental model is simply a representation of how something works. We cannot keep all of the details of the world in our brains, so we use models to simplify the complex into understandable and organizable chunks,” says the Farnam Street Blog. Whether we’re aware of it or not, our brains are constantly sorting information based on the inputs they receive and we make decisions based on our experiences. Learning mental models is a short-cut to hard won experiential knowledge, and i’ll always take the easy path when given the opportunity. Below I’ve highlighted the two models I’ve most employed over the past year.

  • Inversion: One of my favorite ways to improve my decision making is employing a mental model known as inversion to reverse engineer a problem. Instead of thinking about the steps you need to take from start to finish, you begin with the end in mind. There are two approaches to inversion: (1) start by assuming that what you’re trying to prove is either true or false, then show what else would have to be true; and (2) instead of aiming directly at your goal, think about what must be avoided and see what options are left. In my Q1 Reflections, I discussed how employing inversion prevented us from making a mistake regarding expanding our office.

  • Puppet Master: As an entrepreneur and the leader of a company, I don’t have a boss to give me clear expectations, guidance, and mentorship. Because of that, I frequently ask myself the question, “If you had a boss, what would he/she tell you to focus on?” Depending on what I’m solving for, that boss could be an opportunistic private equity overlord or he/she could be a saintly do-gooder that stumbled into business (often I'll challenge myself to think from those two perspectives). Thinking about what a hypothetical puppet master would to me to focus on has challenged me to think at a higher level.

Effective Altruism: I'm don't give much time or energy to charity, which troubles me. Before jumping into commitments, I want to make sure it's a proper allocation of my time and resources. "Effective altruism is about answering one simple question: how can we use our resources to help others the most?" I'm just at the beginning of my journey into effective altruism and I'm hopeful that this will provide me with a framework to do the most good possible.


Asking the right questions is the most important step in solving a problem, but before you can even ask the right questions, you must identify a problem worth solving. My intellectual interests are largely centered around being an effective person. Business wise, I’m only interested in starting organizations that I believe are answering the call of a worthy problem, not because I believe something can be financially successful. Similarly, I’m not interested in virtue signaling but in truly making the biggest impact I can during my short time on earth. Whether it’s learning about mental models or viewing impact through the lens of effective altruism, I’m interested not only in understanding how the world works (i.e., the search for truth) but also in how to be the most effective, integrated person I can be.



Looking Ahead


All in all, it seems like I'm on a great trajectory and there aren't any major changes I think I need to make. That said, I would like to accomplish a few things in the coming year.

  • Spend more time on significant relationships.

  • Grow Green Hill by 50%.

  • Launch a new venture.

  • Thirty days off the grid -- vacation, meditation retreats, etc.

  • Dedicate an hour each day to reading.

Here's to another trip around the sun!

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