I first saw a snippet of this on Instagram before finding the full version:

The 2-minute snippet on Instagram wasn't the same quality, and it still made me cry. I often turn to Dave's music to pursue emotion, and just feel.

My emotion in this is a sense of being torn. I've never seen Dave perform live, and I have tickets to see him perform on this Haunted Churces tour in Barcelona or Vienna in the next two weeks. The plan was for Jeanne and I to do a little romantic getaway, but life is too full to contemplate that at the moment.

So, from afar, I'm basking in this emotion and gobbling up all of the fragments of the tour I can.

I borrowed the headline from Viktor Frankl, who wrote one of my favourite books. Reading Man's Search for Meaning fueled my curiosity and created many questions about humanity, specifically how it related to the Holocaust. I have since read a few books about it in an emotive and intense attempt to understand and learn something.

In the stories of suffering and sadness, one of the themes to emerge relates to connection and our shared humanity. It is captured well in one of my favourite paragraphs from the book:

We who lived in concentration camps can remember the men who walked through the huts comforting others, giving away their last piece of bread. They may have been few in number, but they offer sufficient proof that 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.

I started with that because connection has been at the top of my mind lately. I have been feeling a great desire for connection lately, but I don't want it to be frivolous or fleeting; I want it to mean something.

More importantly, I've learned that when connection is present, I'm not in my head so much. I'm part of something bigger. The (my!?) spotlight is not on me.

This takes various shapes depending on the nature of the season (of life) I am in. I wanted to share a few of those with you.

This past Saturday, my little sister (expecting her first kiddo any day now) and her husband had dinner at our place. During the evening, they asked Jeanne & I whether we'd be guardians for their son should anything happen to them. They said they admire our parenting and the kids we are raising. Not even religious beliefs (I'm not and consider myself a humanist) derailed the conversation or sentiment. Incredibly warm fuzzies were had all around. Maybe "connection" is easier with family, but it's also sometimes hard due to historical issues (irrespective of whether they are relevant). This was such a meaningful conversation, though, and I went to bed with a happy heart.

On Sunday morning, I woke up at 5 am to watch the UFC fight between Sean Strickland and Dricus du Plessis. A key point to note here is that I have never watched a UFC fight, but Dricus du Plessis is South African, and the hype around the fight had even reached me. Dricus won, and this scene from his post-fight celebration is electric.

I'll quickly translate what Dricus said into my own interpretation, too. He said, "Now they know what we know." He alludes to a perception that South Africa - and thus South Africans - are underdogs. But we're built differently (in our opinion), and we can achieve great things. There is a general sense that we - as a "small" country, need to prove ourselves to gain respect. Dricus did that by being the first African to be a UFC champion.

In this context, I am another South African watching a fight on my TV. But seeing how much this means to Dricus and how he connects with a whole nation (or an idea thereof) makes it impossible not to be swept up in this patriotic elation. You can draw the lines as you please, but it is hard not to connect with this shared emotion. I am part of that merely because I was born in South Africa.

I subsequently channelled all of that energy into a 12km run, during which I was absolutely bouncing. This is significant because I had knee surgery in November and only started running again a few weeks ago.

I want to try connecting that sentiment and experience with where I am professionally today, too. I suspect that many of my readers at least first followed me because of my perceived professional success.

This desire for connection has also greatly influenced how I think about work in this season of life.

After Cogsy didn't achieve the outcome we had aspired to achieve last year (more on this soon), some soul-searching helped me realise that I didn't want to build something from scratch in this season of life. Instead, what was clear to me is that I wanted to do meaningful and impactful work.

At the start of the year, I joined Automattic as "Head of WooNew." My primary focus is leading initiatives for first-time entrepreneurs, including projects related to Woo, which I co-founded back in 2007 (and left 10 years ago).

I'm typing this newsletter from New York, where I am attending a leadership offsite. One of the things that I love most about New York is all of the walking and thinking that I do here. As I walked around town today, it dawned on me that during my years building Woo, I truly felt connected to something much greater than myself or what we were building. We were one cog in a much bigger push to democratise publishing and commerce.

I've done many interesting and meaningful things in my life since, but there was a sense of connection and shared interest in that season of life that I have not yet replicated until now.

It's also interesting because so much of the world of open source shaped how I think as an entrepreneur and human. It was also something that I was initially quite reluctant to explore or accept. I remember Matt Mullenweg (my new boss) arriving on a boat (one of those startup'y, hackathon-something cruise ships) in Cape Town in 2010/11 and pinging me for a beer. The venue was subpar (way too loud, in my opinion), but our conversation influenced so much of what was to follow for me.

An African proverb says: "If you want to go fast, go alone. But if you want to go far, go together."

I'm in the latter stage of this season of life. I have done the rebellion and independence. I've done the "buck the trend".

I suspect connection and our shared humanity matter more than we think or want to admit.

So much of capitalist society wants to rank us and differentiate us accordingly. But I suspect we all want to belong.

We might be living in the Matrix, but even when Neo was plugged out, he belonged to a crew.

I have excitedly been working on a mammoth new content project in the last couple of weeks. As I write this, the project already has nearly 100,000 words written, which is rather significant given that Life Profitability just breached 60,000 words. (There is something to be said about quality over quantity. It's my belief, though, that the nature of this project lends itself to have great value in the colour and context of the quantity.)

Also, the new project is not a book. Here's a little sneak peek of what it looks like instead:

The original impetus for the project was to find a way to share some recent thoughts, experiences, and lessons learnt in an unfiltered and authentic way. I believe that I'd gotten myself into a mindset where I was at least partly withholding some of this publicly and instead shapeshifting to an extent to optimise for conversations and opportunities. The project thus started with this forward-looking perspective and goal: share more and without a filter.

As I started, though, it morphed into a very reflective and ultimately cathartic exercise where I started digging into artefacts of my past in my attempt to make sense of my present. This included re-reading past investor updates, journal entries in handwritten and digital notebooks, shorthand notes I left myself on my phone, or late-night emails to my wife to share where my head and heart are.

On that rabbit hole-like journey, I've found gems like this in a notebook from 2012, where I had similar ideas to what eventually led to the creation of Cogsy in 2020. (I had another notebook entry from early 2018 - included in the upcoming content project - where these ideas evolved much closer to what we originally launched as Cogsy V1.)

In overlaying so many different sources of content in my reflection, it's been fascinating to - for example - match how I was feeling, what I was journaling about, and what was happening in my business or professional life at any moment.

The other unexpected observation when zooming out and extending the time horizon of inquiry is how often the same questions or challenges have popped up for me. Things that seemed highly trivial when I first penned it again popped up months and years later. And some of those things are still relevant today.

In "How Proust Can Change Your Life" Alain de Botton writes:

If we read the new masterpiece of a man of genius, we are delighted to find in it those reflections of ours that we despised, joys and sorrows which we had repressed, a whole world of feeling we had scorned, and whose value the book in which we discover them suddenly teaches us.

This is an accurate summary of how I feel after a few weeks of reflecting on my past writings: When I wrote it originally, I wrote it for a different reason compared to why I reflect on the same writing now.

When I journaled, I processed my thoughts and feelings to regain clarity or focus on what I needed to do next.

My practice of writing monthly investor updates was cultivating a discipline of reflection and accountability. It was also to keep myself and others aligned with sufficient information and clarity to progress in our stated goals.

And the shorthand notes or late-night emails were meant to be breadcrumbs I could return to should I forget. I thought these were a huge epiphany and of significant value then. (I rarely found them super-valuable or at least actionable the next morning.)

In re-reading these now, I'm not finding genius, as de Botton suggests. I am, however, finding new or different value. I'm finding recurring patterns and parts of me that I have compartmentalised or downplayed (probably subconsciously for reasons unknown).

I also regret the seasons in which I didn't write as much and when my journaling habit fell by the wayside. This is especially true for the most recent season of life where I was building Cogsy: today, I don't have a lot of additional content after late 2021 when Cogsy raised its seed round. And yet, I know there is so much of that story to be told. (The upcoming content project attempts that, though.)

The regret of not writing more is the only new action that the last couple of weeks have informed: writing regularly in whatever format, irrespective of the reason, is probably helpful.

Beyond that, though, I've not been in a season of action-taking. Instead, I've purposefully avoided taking action in favour of rest, reflection and rejuvenation.

Returning to de Botton and the genius that possibly lies within the reflections. As I've reflected and been reminded of these patterns and parts of Adii, I've felt calmer and more integrated than I have in a while. This has been especially helpful in solidifying and powering up my core again as I plot my next steps.

As a final (and ambiguous) teaser for what the content project will include, I'll share one of those shorthand notes that have helped me integrate various experiences, emotions and thoughts to create a new sense of calm (and self/Self)...

FOMO happens when you're not in the moment when you don't do what you feel compelled to do (but for whatever reason, you rationalise not doing the thing).

I tend to land somewhere between Socrates and Epicurus.

I understand that not all my decisions would pass the high water mark that Socrates' critical thinking require. And at the same time, most of my decisions are not Epicurean at all. I work more than play, even though I would tell you that my work is often play (at least to some extent).

All of this is future states to some extent, though. We take a view of self and the future that is more about tomorrow than what it is about today. Ego/Self propels us forward to a better state. Nothing wrong with that. And when we do that blindly, we've skipped over what is (and - in hindsight - was) important today at this moment.

I suspect there is no way to know with absolute conviction today that you have lived a good life. I know that a good life is likely a combination of good moments.

Neil Young said, "it's better to burn out than to fade away". Kurt Cobain quoted this in his suicide note.

I bet both would concur that they only had a single life to live. (And that they both lived through incredible moments.)

As binary as the outcomes seem, we only need to know that the spectrum is so vast when we place ourselves on that spectrum.

You live life (only) once.  

All of us face a similar bottleneck in scaling our ideas and efforts: our time - and energy - is ultimately finite.

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