Man's Search for Meaning

First up... I'm writing this newsletter exclusively and not publishing it anywhere else (not my blog or any social channel). If this is interesting/valuable/helpful to you, please share this with a friend (or friends). I would truly appreciate that. 🙏

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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:

I started with that, because connection has been very top of 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 own 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 the historical stuff (irrespective of whether it is 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 in my life, 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 with 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 seeing how he connects with a whole nation (or an idea thereof) makes it impossible to not 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 where I was absolutely bouncing. The significance is that I had knee surgery in November and only started running again a few weeks ago.

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I want to try connect that sentiment and experience with where I am professionally today too. Because I suspect that many of my readers at least first followed me for 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 to lead initiatives for first-time entrepreneurs, which includes projects that relate 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 to have a beer. The venue was sub-par (way too loud IMO), but our conversation influenced so much of what was to follow for me.

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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 state for this season of life. I have done the rebellion and independence. I've done the "buck the trend".

I suspect that 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.

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I'd be less likely to be writing and sharing this if Marcella hadn't been such an incredible friend. And now she's a coach too, which means she can be your professional friend too. Have a look at her writing and work: