What Happened in 2017

My Annual Review: Wins, Failures, Lessons Learned

The purpose of this annual review is to reflect on the year which has passed so that I can celebrate my wins, diagnose my failures, and prepare for a successful year to come.

This annual review is for me but I would like to share it with you because:

1. If we hold each other accountable, our success becomes exponentially more likely.
2. Each action of transparency is a small step towards integrating the public and private versions of myself.
3. I want to frame our future conversations around how we can help each other shape the world and become the best possible version of ourselves.
4. It might inspire you to do the same.

In my annual review, I will answer three questions:

1. What went well in 2017?
2. What didn’t go so well in 2017?
3. What am I working toward in 2018?

What Went Well in 2017

The Forcing Function

I focused full time on productivity coaching in 2017, helping 20 clients realize their entrepreneurial visions and find purpose in their lives. I turned my productivity coaching from a PDF into a fully branded business and a supportive community.

For as much as I still doubt myself, my abilities as a coach have improved by leaps and bounds from where I started. Where I used to teach or give advice I now actively listen and ask questions. I realized that clients already hold the answers to their challenges and that my role is to help facilitate discovery. It has been incredibly rewarding to play a small part in their success.

I have been raising the bar of who I choose to work with and I would now place my current clients at the tops of their respective fields. Having seen consistent results, I want to start making larger ripples as the right hand man to those working to change the world.

Exercise

For most of my adult life, I shunned exercise, spending the majority of my day leaning forward in a computer chair. I finally realized that a few small lifestyle changes could reverse years of damage and add several decades of physical mobility and cognitive flourishing. I made improving health my top priority of 2017 and it is impossible to understate the difference in how I feel and carry myself day to day.

With the help of an incredible personal trainer and yoga instructor (shoutouts to Westley Chow and Vinny Bonnano!), I weight trained 2–3x/wk and practiced yoga 1–2x/wk. I started and ended my days with stretching and incorporated it into my breaks. When the weather was nice, I even biked to work at a cafe or walked instead of taxi or subway.

My original goal was to reduce body fat by 2% which I blew away, going from 15.3% to 11.6%. While my focus was more on functional mobility over strength, approaching 300 pounds (for 8 reps) on the back squat and deadlift was really validating. I finally dissolved my lifelong identity of someone who “isn’t very strong.” I’m easily in the best shape of my life and still improving.

Diet

For my first year in NYC, I ate out for every single meal. This year, I paid more attention on what I put into my body, using a food log with macronutrient tracking to overhaul my breakfast and lunch options to start the year. I now eat relatively “Paleo” for those two meals.

In December, I ate a simple fish and plant based diet as part of a retreat, cutting out all meat, dairy, sweets, and spices. As I lost ten pounds of muscle, I’m not sure this is a long-term solution. However, the difference in my energy levels from eating only quality ingredients was undeniable. I learned the importance of separating eating to sustain from eating as entertainment.

I still have work to do. I’m still way too reliant on delivery which is time-efficient but expensive and requires too much willpower to stay on plan. I tried meal delivery services specializing in healthy options but the portion sizes and quality didn’t match the price points.

As the year progressed, I cooked less and less and ordered in more and more. The positive results I have achieved on diet were mostly thanks to having a girlfriend who enjoys watching me eat her tasty food. Also, my discipline when it comes to sugar and grains tends to disappear on weekends or when I’m eating out.

Poker

I thought my poker days were behind me and that the game had passed me by after five years in retirement. In May, I was alerted to a new and promising online site that I decided was worth a trial. It quickly became apparent that I still both loved the game and was very much a top-tier player despite my outdated strategy.

From June until December, I played an average of 20 hours per week in the evenings, and did very well. I regained financial freedom and could be very discerning who I took on as a coaching client.

There are always trade-offs. I often struggled to balance poker with other priorities. It added extra stress and made sticking to a consistent sleep schedule very difficult. Poker’s zero-sum and cold-blooded nature runs counter to my long-term mission. For now, I think the tradeoffs are clearly worth it but it is always uncertain how long opportunities like this will last.

Podcasts

I guested on seven podcasts and enjoyed immensely attempting to compress the sum of my knowledge into a 30–60 minute conversation. My best thoughts seem to magically emerge when the red light is on. Like improv, simply showing up for a high-level conversation is the lowest friction way to share.

Podcasts are a crowded space right now. Right now, the biggest benefit might be using transcription to get my ideas on paper. I expect the audiences I reach to grow as I continue to improve and prove myself as a guest.

Comedy

I continued my pursuit of comedic catharsis this year through improv performances at the Magnet Theater. I even did standup twice on the Comedy Cellar main stage as part of a class for professional comedians.

Improv is always fun but performing standup was really stressful. You have teammates to lean on in improv and there is no preparation required. Creating an original standup routine that somehow appears spontaneous and natural was much harder than I expected.

The rare moments where the audience was in the palm of my hand were such an incredible rush. I can understand now how professionals are able to push through the torture. I overcame my fear of public speaking and improved my storytelling while increasing my enjoyment of the awkward dance that is spoken language.

Finances

My coaching income quadrupled from my first year, helping me reach my goal of cash flow positivity even before earnings from poker and investing. I had lived off savings since leaving the startup world in 2014. With anything finance-related, my tendency since then had been to just bury my head in the sand.

I created my first ever budget and began tracked my expenses to regain control of my spending. For the first half of the year, I stuck to my budget pretty closely, cutting down on my burn rate significantly. I even sought out additional income streams and investment opportunities, a couple of which became primary lines of business.

As my income increased, I switched to an investment mindset, aggressively exchanging money for time and energy. My spending ballooned as I spent almost half my time traveling in Q3/Q4 and my earlier budgeting was all but forgotten. #noregrets.

This current high-income period might not last forever so my hope is that my previous discipline will return when needed.

Relationships

I evaluate my progress on relationships based on the quality of the people who choose to spend their time with me: what are their levels of ambition, curiosity, and caring? I was blown away again this year. Several people who I recently thought “would be awesome to even talk with them” are now among my closest friends.

Being open and charismatic in groups has always been a challenge for me but I’ve made a lot of progress. I think I am particularly skilled in helping create memorable experiences for others. In 2017, I co-hosted 16 parties and dinners at Castle Keap and shared so many unique NYC cultural experiences including dozens of amazing concerts and performances.

I am pleased about reducing my alcohol consumption with no social repercussions by substituting with non-drinking activities or savoring a single high-end drink.

Admittedly, I didn’t take much initiative on making things happen, especially once poker started taking over my evenings. I would give most of the credit to roommates and friends for dragging me off the computer.

My relationship with Marianna continues to be a highlight. The three years since we met have been the happiest and most fulfilling of my life. Not much to say other than how well things have been going. I feel so lucky and grateful to be with her.

Travel

My travel schedule was subdued compared to years past but the trips I did take were incredibly rewarding.

My highlights were:

• Exploring Portugal with Marianna (July)
• Taking a road trip through northern California (Aug)
• Co-organizing Camp No Boundaries on my 5th straight year at Burning Man (Sept)
• Indulging the senses and studying the perfection of progress on our third food and whisky tour in Japan (Nov),
• Climbing mountains in Patagonia (Dec).

While these trips take tons of mental bandwidth to do right, they bring so much more growth, learning, and happiness. I find the natural opportunities to step back and take a 10,000 foot objective view on my life indispensable.

A global perspective is more important than ever and first-hand experience is the only way to truly understand the world. The trick with travel, as with everything, is striking the right balance… not oscillating too close to either indulgence or irrelevance.

5 Countries Visited (2 new): St Lucia, Portugal, Japan, Peru, Argentina

10 US States Visited (0 new): NY, MD, NJ, VA, VT, CA, NV, TN, AL, OH

Planning / Reviews

I tell every productivity client that if they retain only one habit from our work together it should be the weekly review. I ate my own dog food and made weekly reviews a priority, sitting down for 30–60 minutes weekly without fail. I also added in a new monthly review so I could regularly rebalance where my time and energy were going with respect to my annual and lifetime goals.

The best way to ensure a productive day is to plan your priorities and schedule in advance. Last year, without a planning habit, many days became a black hole. Installing a daily standup with Rob Filardo where I presented my plan and schedule for critique was a productivity superpower. Even if I failed to plan the night before, this ensured that no day went unexamined.

What Didn’t Go So Well in 2017?

Writing

In February, I spontaneously began writing a book, Inflection Point, to share my takeaways from working as a productivity coach. After two months, I had an 80 page rough draft completed, more than I had written in the last decade combined.

I naively assumed that with a rough draft in hand, I was 80% of the way done. My friends with books under their belts assured me that the true percentage was closer to 20%.

Progress stalled out. I lost interest in the subject matter and felt a general disdain towards everything I had written. As poker reentered the picture, writing fell down my list of priorities and I found myself constantly self-sabotaging.

I began publishing individual chapters as blog posts on Medium to streamline the editing process through public accountability and reinforcing feedback. This worked for awhile and I was able to put out 5/16 chapters but each post took longer than the last. While response among friends was overwhelmingly positive, I put no effort into distribution and became less motivated each time the posts failed to reach a wider audience.

So… writing a book is hard and I didn’t quite know what I was getting into. My disappointment comes from falling short of the ambitious goal I set for myself as well as all of the old insecurities and self-sabotage that those expectations resurfaced.

I did manage to get all my productivity techniques and mental models into a form that could be shared with others. I accomplished more writing than I had… basically ever.

Hiring

My ambitions with The Forcing Function are far beyond what I can accomplish on my own as a solopreneur splitting focus on a lifestyle business. I had a Program Manager working for me for two months before she accepted a full-time position elsewhere and that was likely my most productive period for coaching of 2016.

A major goal for 2017 was to find a suitable replacement. I posted a job descriptions all over, received dozens of application videos, and even conducted a few phone interviews.

Then I went dark. I couldn’t decide what type of candidate I wanted or what exactly I needed them to do. As I write this, I’m still not completely sure.

I became afraid of losing my freedom to work how and when I wanted. I knew that someone’s help would guarantee more visibility and progress and I instinctively flinched away from the responsibility.

I maintained my autonomy but at the high cost of not having the time, energy, or initiative to move my most ambitious ideas forward, being forced to postpone or abandon them altogether. Failure here was both a symptom and a contributor to playing smaller than I would have liked in 2017.

Speaking

I led two talks on habits and priority management and co-facilitated a workshop on goal setting. These went really well but I had my sights set higher and never seriously pursued other opportunities. I wanted to do a TEDx talk in Q4 but put up needing to finish Inflection Point first as an artificial barrier.

An original goal was to experiment with expanding scale by hosting a live and an online group productivity workshop. The effort to produce and sell out such an event seemed daunting and I never made a serious attempt to put either into motion.

Daily Routines

My habits were less consistent this year. My routines became a bit bloated, stale, and disconnected with original motivations. I pulled back on the tracking and rewarding completions which might have been the scaffolding all along.

My morning routine of stretching, journaling, and meditation was fairly solid but not automatic like before. If I was traveling, up late, or had plans in the morning, it rarely made the cut.

Without a consistent shutdown routine to end the work day, I frequently blurred the line between work and leisure making me more stressed and less organized. Not having a consistent bedtime made my evening routine sporadic, contributing to my sleep issues even more.

Sleep

Sleep is my biggest health challenge and productivity bottleneck. After having very consistent bed/wake times to start the year, my entire system got thrown off with the addition of poker as the best poker games are often late at night.

I would play until the wee hours while still forcing myself out of bed in the morning to maximize the daytime hours when my focus is highest. All time allocation decisions are tradeoffs and in this case, sleep was the costly sacrifice. I would often crash in the afternoons or lose whole days where I felt like a zombie.

I began tracking my sleep using an Oura ring and found out that the problem was even worse than I suspected. Even when I set aside enough time for sleep, my sleep quality was terrible. 20–40% of the time I thought I was “sleeping” was actually spent tossing and turning and I was receiving almost zero deep, restorative sleep.

I researched and replaced everything in my bedroom related to sleep and made numerous adjustments to supplements and environment with minimal improvements to show for my efforts.

The only solution I have found is to treat sleep like a priority. For me, this means 9 hours in bed (to ensure 7 hours of sleep), getting 30 minutes of sunshine and exercise during the day, and successfully unplugging and winding down to end the day. Still a work in progress.

Reading

This is a tough one. I read 40 books, a total that I’m very happy with as I didn’t have a reading goal in 2017. In fact, I had deprioritized reading, deciding that action, not knowledge, was the limiting factor to progress.

I was successful in reducing the time I spent on online blogs and news articles as well as mostly removing social media as an information source. I made online reading harder to access compared to my Kindle by setting up blockers, tightening filters, deleting apps, and reducing the escapism appeal by requiring myself to make highlights while reading.

However, I had little or no intentionality behind what I read. I overweighted the last interesting book mentioned to me rather than starting from what I wanted to understand. I hopped around topics a ton, often juggling up to a dozen books, so much of the intended context was lost. I often read while distracted or right before sleep which hurt my retention. I abandoned more books than I finished because they were too dense or challenging to read.

Depth

I felt like my focus was too scattered this year. My drive for novelty has served me well but I have clearly hit diminishing returns.

Trying to do too many new projects and hobbies without enough conviction behind them led to unrealized efforts. I got pulled in too many directions with my learning so that I could be competent or simply hold a conversation rather than pursue mastery of the critical few.

I already have all the books I need to read, I don’t need to browse lists looking for more. Meeting new people is great but I want to deepen the relationships I already have by increasing the presence I bring to our interactions. At each decision point, I am biased towards explore the boundaries of my passions and missions rather than take on new ones.

What I am Working Towards in 2018?

These are just the broad themes, specific goals are in my 2018 Goals post.

The Forcing Function

I realized that one of my greatest gifts is my ability to empower others. My long-term mission for my coaching practice is to be the right-hand man to those who are creating a better world. Many of these individuals are hesitant or unable to make the investment in personalized coaching but accelerating their vision is why I started coaching in the first place.

Thus, I will be introducing sliding scale scholarships for clients based on need. I will also be seeking out and offering my services free of charge to selected individuals who I think are doing particularly interesting and valuable work as my schedule allows.

Inflection Point / Blogging

Despite my challenges from writing, it is still the most effective way to disseminate my ideas to a wider audience. I am restoring Inflection Point to my top priority after client work to ensure that it gets published this year.

I will also be sharing more ephemeral thoughts and updates on my latest learnings and experiments. My hope is that I will overcome perfectionism, tighten feedback cycles, and make sure my work stays relevant. Disengaging on social media in favor of real connection was a huge boost to productivity and happiness so this might be a tenuous balance.

Journaling

My journaling frequency is proportional to my level of engagement with the world. My ability to retain impressions, ideas, and next actions is limited without a place to capture them and too much of my mental bandwidth has been dedicated to being a poor storage device. The more I write, the better my writing will become and the more I say, the more I will have to share.

My journaling consists of morning pages (clearing mental clutter) and a Captain’s Log (preparation and processing for unexpected experiences). I would like to build upon the depth and consistency of these practices.

Yoga

Yoga was a huge win for me this year. I began to reverse years of damage my sitting at a computer caused, making huge gains in posture, mobility, flexibility, and overall energy retention. When I practice, I feel much more embodied and I think I am just scratching the surface of what strengthening the mind/body connection has to offer. I am going to continue to receive private instruction as well as attend more regular classes.

Meditation

While my meditation habit was inconsistent this year, the days where I did meditate had a more effortless feel to them. I am convinced that focus, presence, and awareness will be the distinguishing abilities of our generation and that the war for our attention has only begun.

With this in mind, I am building back up to sitting for 30 minutes daily. I will also attend a 10 day silent vipassana retreat as well as a weekend stay at a monastery to deepen my practice.

Diet

I would like to “solve” my diet. I spend so much mental energy trying to decide what and when I am going to eat every day.

Additionally, the nourishment I need to operate at peak will not be found at a restaurant. The incentives simply are not aligned. I want to be taking back more control of what I put into my body.

I will be taking classes to try and spark a passion for cooking and expand my repertoire beyond steak and chicken. However, experience tells me that suddenly cooking all my meals is unlikely to happen so I will be looking to partner with a personal chef who can help ease the burden of meal planning and preparation.

Overall, an excellent year! Many major successes and only a few minor setbacks that I expect to overcome. I feel healthier, happier, and more accomplished than ever before.

Writing this review was so difficult but so very powerful. To ensure an excellent 2018, I highly encourage you to ask yourself these three questions and share your answers with at least one other person. Godspeed.

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