My Breakthroughs and Lenses from 2022 and Themes for 2023
My Breakthroughs and Lenses from 2022 and Themes for 2023
On the lenses 🔎 + inner work 🧘🏻 + breakthroughs 🤯 that helped me arrive at the current, latest, best version of myself (so far)
This post will focus on the personal breakthroughs, and I'll separately post on on the professional insights as well (from a sabbatical, multiple professional narrative redefinitions and repositionings, and my attempts in the world of consulting / fractional work directly, as well as learning from others like Reforge experts, consultants in the education/impact space, many other growing consulting/fractional practitioners and experts and reading work by Venkatesh Rao and Paul Millerd).
2022 was a huge year of transition for me, including major changes to:
🏡 where I call home, from South Africa back to the US
and specifically for now Atlanta, which we chose because my wife and I enjoyed it most here (as compared to the Bay Area) and intentionally because of proximity to family
💵 how I make a living, and how I iteratively evolved the framing of my experience, narrative and what I’m looking to do next:
taking an exploratory ‘what do I do next’ sabbatical,
trying multiple startup ideas and collaborations,
trying different ways to generate income and monetize my expertise/skillset: consulting, teaching, launching and running a cohort based experience x 2, taking on a full-time job
🤰🏾 how my family evolves, with my wife and I finding out we’re expecting our first child (a boy)!
☯️ how I view myself: key realizations about underlying causes of self esteem and self worth due to my relationship with parents and a hidden assumption that I internalized from a very young age, that I thought I had to earn my parents’ respect and love
It was also a challenging one, where:
🔥 I got ‘fired’ from a consulting engagement, although I used the opportunity to seek feedback and improve external self awareness.
🪓 I got laid off from my FT job (a month and a half before my son’s due date!)
🏫 We shut down the flagship primary school of Streetlight Schools which we had grown grade-by-grade, brick-by-brick from 60 students Grades K-1 to over 300 students Grades K-7 from January 2016 when we opened the doors to the school to December 2022.
😷 I dealt with the vagaries of consulting life and layoffs, and the impacts on healthcare access — I dealt with two different COBRA administrators (yikes!).
☁️ I had a lot of ideas and conversations that didn’t get off the ground or ultimately lead to tangible output.
Through my annual reflection process, I had some powerful insights from 2022 that will carry me into 2023 and beyond:
tl;dr:
🤝 Play Long Term Games With Long Term People
🧘🏻 The Most Important Long Term Game Is The Inner One
❤️ Combating Intergenerational Pain Through Unconditional Love
🦋 Why My Life’s Work and An Important Long-Term Game Continues To Be:
Take On Challenges To Empower Myself and Others
Build and Scale Transformational Experiences, Products and Businesses
(although I really do love someone else’s turn of phrase, which is to ‘scale wonder’)
Building on these breakthroughs, I’ve set the following:
🎼 Themes for 2023
📜 Principles for 2023/
* (intentionally and explicitly, these are not goals)
1/ Play Long Term Games With Long Term People
The first most important lens of 2022 was playing long-term games with long-term people. Thanks to Theo Sutherland for sharing this phrase and lens, originally courtesy of Naval Ravikant.
Being a deeply giving person means it's hard to establish boundaries (with work, with colleagues, with others), but after hearing this concept from Theo, I worked very hard this year to prioritize finding like hearted, like minded, like valued individuals, and building relationships. When I found those people:
I found ways to collaborate and create together.
I kept in touch and added them to my personal community that I champion, and share articles, ideas and life updates with.
There was no system really (although I do keep a CRM spreadsheet of people I interacted with, especially those that feel values aligned): I used gut, network (asking others/references), and also saw if they genuinely helped or added value to me.
As a positive example and a negative example:
I tested On Deck’s Cofounder Sprint/Matching (which I believe they were piloting last year), and surprisingly met three really unique founders at different stages whom I really hit it off with. I ran an experiment with one of them trying to build and validate an idea which we ultimately decided to shelve, BUT I do not consider it ‘wasted’ time because:
a) we got a chance to suss each other out in a small stakes project (and really suss out each others’ strengths and weaknesses; and given the chance, I’d do another project with him) and
b) we will likely remain in touch because of deep values and experience alignment.
I’m generally willing to take a first call, at least if I see enough overlap in our respective areas of interest and priority (and it’s not pure sales outreach where what they’re selling doesn’t make sense or I suspect its quality/fit). But, I tried to communicate and set clear boundaries or just stop engaging when I realize someone:
a) offers to help but doesn’t follow through and/or
b) continues to ask of my time without clear value add to me.
One of the easiest ways to do this is to ask if they’re willing to exchange value for your time (e.g., equity, cash, time/collaboration, intros/network), and try to define an explicit advisory / coaching / consulting / collaboration relationship. I don’t go into every conversation trying to do this, but if it’s clear I’m adding a value and spending time with this person, then I try to shift into a mode where I figure out mutual exchange of value.
Playing long-term games also means defining the game / lane / area you want to play in. I’ll speak to this more in my next post, but I evolved my narrative and what I thought I wanted professionally multiple times this year, over time going from:
wanting to be a PM in a hypergrowth tech company
to being a consultant
to founding another company
to joining an tech company in a product role (with a focus on edtech / workforce development) —> how I ended up at Reforge
to being a fractional executive
to focusing on growth roles
to framing myself as a generalist co-founder/early employee in edtech and workforce development (which is my latest in my current search, and I hope to also eventually expand beyond those industries).
to finally landing on the niche / intersection of (product-led) growth x edtech and workforce development (my LinkedIn post from the day that I had a eureka moment!)
(which is really data-led growth, hat tip to Hila Qu for that gem in a recent podcast)
2/ The Most Important Long Term Game Is The Inner One
a) The most important personal breakthrough moment of 2022 happened in November, after my layoff. There were two triggers:
I had been watching breakdowns of the world building and characters of Avatar (The Last Airbender, not of James Cameron or blue people fame), and particularly looking at the redemption arc of Zuko.
tl;dr he was the prince of a nation who when he spoke out of turn at a war council was challenged to a duel by his father; when Zuko refused to fight, it was was seen as a sign of weakness and as punishment, his father scarred and disfigured his face and banished him.
Zuko’s arc of redemption is one where he initially yearns and does everything he can to prove his worth to his father so he can return, before finally through the entire series realizing that it was his father who wronged him, not the other way around and that his father’s choice of waging war on the other nations has caused incredible suffering and pain)
I noticed myself gravitating (in both listening and playing) toward some particularly poignant and sad songs, especially this heart-wrenching and aching cover of I Can’t Make You Love Me by Bon Iver.
It was Friday, and I paused to take a beat to recognize these triggers, play some music as a way to channel and process my emotions, to allow them to surface. When I realized something serious was going on (I was in my feels man, tears flowing) — I paused playing piano, and cancelled the rest of the meetings I had that day.
An important part of 'creating space' for such breakthroughs that I learnt through this experience and have continued practicing is vigilance / observation / keeping in attuned to your different parts so when your emotions surface or well up unexpectedly (when a part of you shows up, and you may/may not immediately recognize which part), you are ready to grant them an audience
(or if it shows up at an inopportune time, making a note and coming back to revisit).
Through reflection, conversations with my wife, my sister and my friends, I got closer to the core truth, the root cause of my life-long self esteem, self worth and imposter syndrome issues:
I had from a young age internalized the mistaken belief that I had to earn my parent’s love and respect (rather than the belief that they would love me unconditionally, no matter what). From this stemmed my self-esteem issues, my lack of self-love/self-worth (my parents weren’t able to articulate this concept, and I didn’t discover it until in my late 20s reading Brene Brown), my people pleasing, my push to succeed academically unquestioned for so long.
b)
The foundation of unconditional self love is typically built through parents providing and expressing unconditional love for their children that they deeply understand as such (whether acknowledged explicitly or implicitly, somehow the child gets and internalizes this foundation). A big challenge for many parents is how to express this, especially common amongst Chinese and Asian American parents (as well as immigrant parents at large) -- there is no doubt many of them love their children, but the expression of such that their children understand this as unconditional. That's the hard part. (and some both either project their own deferred dreams/ambitions or actually do not express love unconditionally, which I think goes to the heart of the debate around tiger parenting —> you can be a tough parent and push your child to succeed and it may work also depending on their personality, but for every Shaq, for every Tiger, for every Serena, how many countless untold people don’t achieve at the highest level in their discipline or field and are left bearing the scars of such…)
A lot of my seeking validation in academics, in competition (piano, videogames, card games, sports), in performance, in career success, and in romantic relationships came from lack of self esteem and lack of self worth/love. I started unpacking and unworking this about 5 years ago thanks again to radical candor feedback from others during some challenging moments, and the recommendation to read Brene Brown's Gifts of Imperfection.
In parallel, there was a big emotional awareness and processing deficit because I had also (tried to neuter) my emotional valence and response. Only by attending a Vipassana retreat did I gain a deeper understanding of the conditioned trigger response cycles of pleasure --> craving and pain --> aversion. And did I understand that doing so allows you to be more present and amplifies the emotional valence.
c) The lead up to this huge breakthrough resulted from the following:
continuing to my practice of gratitudes and reflections (answering weekly, what was I grateful for, what did I learn, what was I down about, and what are my intentions for next week)
layering on trusted feedback from long term people (internal and external self awareness) —> I both set up a personal advisory board and also sought a coach (again) at the end of the year
making intentional space when emotional triggers and responses arise to explore and unpack them with curiosity
improving your inner game allows you to unlock the best and most authentic version of yourself (and no one but yourself) and this is why I’ve finally come to realize and belief that building your own sense of self identity, worth, agency over time is the most important long-term game you can play
To get a sense of my own framework and view of self through this lens over time, check this out (my own self actualization framework I built and leverage in a personal and career development fellowship I ran two cohorts for in 2022):
Framework (borrowing and stealing from others):
Framework applied to myself and major breakthroughs in the last 5 years, all of which happened after I made the high conviction move to South Africa to build Streetlight Schools:
3/ Combating Intergenerational Pain Through Unconditional Love
Taking both the key insights from 1 and 2 into account, the most long-term people of them all are:
my partner and wife
my family
my newborn son
my people: values aligned friends and colleagues who show up for me, and for whom I would show up in turn
Focusing on the internal game was absolutely vital to figuring out my own triggers, blind spots, and especially learning how I deal with stress, anxiety, anger, frustration, sadness (there are usually two modes, protective and aggressive —> I’m definitely someone who exhibits more of the latter, and tend to lash out when I’m not doing well).
Becoming better able to identify, process, articulate and express my emotions and inner game has helped me significantly be a be a stronger communicator and partner. In fact, pretty much all of my ability to do this has been in fact due to the love and patience of my partner. She literally has made and continues to make me a better person every single day.
It’s been a blessing to be back in Atlanta with my siblings (and in fact, being in the same neighborhood as my sister and her husband), as this also has enabled us to unpack these things together, helping each other unpack and come to terms with our upbringing, and in turn building stronger, deeper relationships with them as well. It’s incredible to know I have these two three amazing humans (my brother and sister, and by extension her husband) in my corner, and to also be 1000% in their corner as well.
And finally, the realization above about unconditional love absolutely could not have happened at a better time: on the eve of becoming a parent.
If we want to empower people, and break the cycles of inter-generational trauma and pain, I cannot think of more important work (if you choose to be a parent) than:
striving every day to express unconditional love to my son (in a way that he is able to understand and internalize),
as a starting point to help him build the deepest sense of self worth, belonging, meaning, the multitudes of his identities (amongst other things, he will be Han Chinese Xhosa South African American),
to enable him to grapple with all the forces that will try to shut him down or hold him back, and
help him unleash the best version of himself toward living his values, principles, hopes, and dreams.
In addition to my wife, siblings and the arrival of my son, a huge thanks to conversations with and resources from Marshall Buxton, Lawrence Li, Michelle Huang, and Steve Schlafman that also allowed me to reflect and process my realizations.
4/ My Life’s Work and An Important Long-Term Game Continues To Be:
Take On Challenges To Empower Myself and Others
Build and Scale Transformational Experiences, Products and Businesses
(although I really do love someone else’s turn of phrase which I recently discovered, which is to ‘scale wonder, H/T to @michellehuang42’ —> transformation, empowerment, agency, hope, optimism, wonder, curiosity, imagination are all interconnected elements that I believe are woven together in a beautiful tapestry of the beautiful and positive ways you can help someone transform)
When I began my journey into education and impact back in 2013, I had a much more narrow lens and understanding of education, as a means to help people unlock their potential. I had only a vague sense of what that really meant, and was driven by a sense of responsibility (and perhaps survivor’s guilt) at all the opportunity I had been afforded through sheer luck (my parents having emigrated to the USA when I was but a newborn).
I have continuously updated and refined my Northstar, my life’s work, what I consider to be the cathedral that I am building toward — and all of the above are very important context for the depth and nuance of what I mean when I say transformational experiences. They also have given an even more deeply personal motivation, and this actually I think also represents an important evolution in my thinking since my education ‘manifesto’ I published in 2020 (as I was exiting day-to-day leadership as CEO of Streetlight Schools).
5/ Themes for 2023
After finishing looking backward to 2022 and these important insights, I began looking forward to 2023.
Hat tip to Seth Trudeau for his approach to goal setting by themes, and his reflections from 2022 as well as conversations with Karn, Lawrence and Zac which triggered a shift away from strict goal setting toward thematic focus areas.
After thinking about what will likely be the most important themes of 2023, I settled on the following four:
🧘🏻 Continue to make space, show up, seek feedback, be aware of and grant audience to the different parts of myself as I continue to grapple with prior, deep-rooted assumptions and unwork 30+ years of self-limiting beliefs, being as authentically and unabashedly me on the continued path to self actualization
🐣 Find joy and balance and learn the ropes of parenting
Thank you to everyone who shared advice, who helped support us via our registry and/or virtual baby shower, and who shared additional documents or resources that helped y’all make it through.
A month in, and we’re figuring this thing out! And we are full of joy and love learning and living with our little one.
⚖️ Make a living filled with balance, joy and agency
Related goal (ok yes, still have one goal):
💼 by end of March, land the next (major) paying client/gig/jobRelated theme:
🚀 Work on the foundations for escape velocity beyond a life where I’m effectively just trading time for money without much flexibility
🌱 Extend and build support and generosity across my community: family and friends (and not be shy about asking for help too)
There’s an element of growing and deepening our community roots in Atlanta, continuing to rebuild relationships with family members here.
And there’s an element of making time and space for close friends no matter where they are.
6/ Principles for 2023
After reflecting on how I spent my time in 2022 (which was a year of transition and explorations), 2023 will hopefully be a year of focus and consolidation.
CONTINUE: playing long-term relationships, with long-term people
Do less, better (don’t half ass two things, whole ass one ~ Ron Swanson)
Avoid shiny object syndrome (SOS)
Be more patient
Be more present
Find space for meditation and reflection (and therapy)
Focus and prioritize
Set clear boundaries with people who are not values-aligned
Business wise:
🥱 boring is better
💰 validation over vision
🥾 bootstrap until real PMF
💰 (then, if desired) raise money to grow/scale —> will do so from a position of strength, and avoid premature pressure to grow/scale for growth’s sake
Thank you for sharing your heartfelt, deep and creative reflections David ❤️ Wishing you all the best in your adventures