I've been told that (when writing) one should lead with the hook and not bury the lede. So, I'll start by telling you that I got terrible news on Friday that ~35% of my financial portfolio vanished.

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After wrapping up Cogsy last year through an acquihire and voluntary liquidation (I shared the whole journey in great detail here), I found myself asking a similar question that I'd been wondering about on and off over the years: Who is Adii if Adii is not an entrepreneur?

The biggest part of me just wants to Adii, and I've realised that I have a testy relationship with labels.

Do I have some or even most characteristics associated with a typical entrepreneur? Yes.

Am I a dad? Well, yes, I'm a biological father to three kids. But describing me as a dad feels very limiting.

I can continue in that vein for any other labels that might be useful in describing who I am. My point is that I've never found a single label or word that completely describes me, and I wholeheartedly expect the same to be true for you.

My attachment to "entrepreneur," though, is a little harder to shake completely. This is possible because my work has been a huge component of my life, and in many ways, it was probably the first step to discovering so many other parts of me. So I'm back asking the same question.

Who is Adii if Adii is not an entrepreneur?

When I joined Automattic at the start of the year, part of my motivation was to figure out whether I could do meaningful and impactful work within a much larger organisation that I don't own or where I'm not the boss. In that context, I can then probably reframe that question to something like, "How do Adii's entrepreneurial traits show up in this role?"

First, I've learned that this line of inquiry is limited because it extends only to this role and my work. So, it ignores the greater consideration of what this means in the context of my life. (If you've read Life Profitability, you'll know that I believe work is just part of life.)

That first learning then unlocks a completely different perspective. One where - upon reflection - I've boiled down what it means to me to "be an entrepreneur". I realised that the "entrepreneur" label resulted from me doing things. The motivation for doing those things was not "to be an entrepreneur", though.

As I'm re-thinking entrepreneurship, I'd like to share an updated definition of what it means to me today:

1. Entrepreneurship is about doing meaningful things. We attach meaning to many things, but I highly doubt that it is limited to making money or doing one thing (work) for 40 hours a week.
2. The "way I work" is way more important than I thought. There is freedom in being flexible according to your definition and choosing with whom you want to work.
3. Earning great money is inherently very rewarding, and at the very least, it is a pragmatic way to root our perspective in a broader reality (actual money is required to put food on the table). Earning too little money to live the life you desire is a problem. Earning more than you need to live your desired life doesn't automatically fix the first two things on this list (or many other challenges in life).

They say that the music you listen to as a teenager is the music that tends to stick with you later in life.

I grew up listening to a local Afrikaans punk band (provocatively) called Fokofpolisiekar. For the last few days, I've been mulling over the lyrics in their song, Swanesang ("Swan song"):

Die oop pad het sy tol ge-eis
Om vinniger daar te kom sal jy vinniger moet ry
Om vinniger te lewe maak jou vinniger dood

Here is my translation into English:

The open road has taken its toll
To arrive there sooner, you will have to drive faster
Living faster will kill you sooner

This strikes a chord. I have always believed that I have had a very full life, and at a relatively young age (39 😅), I've done and experienced quite a lot.

I mostly look upon my past with great fondness and gratitude, partly because I recognise the good fortune along the way. I also know that I had a near single-minded focus on progress and success for many parts of my journey. I was enamoured with the idea of arriving at the destination, and I got lucky in that I also mostly enjoyed the journey on the way there.

I learnt much later in life that I was also ignorant of the costs that this journey and pursuit created. (My book, Life Profitability, is my best attempt at capturing these lessons.)

The biggest challenge along the way was those moments of the journey that were uncertain, risky, or incredibly tough. In those moments, the experience of the journey was not what made me show up to do the work. Instead, I stuck to the vision of reaching the destination. I learnt grit and resilience and learned more about myself than I could have hoped.

In that, there is also a double-edged sword.

Fokofpolisiekar's song continues:

Slagoffer van jou eie verbeelding
Die droom het 'n nagmerrie geword
Skuldig bevind, morele verkragting

Again, with a translation in my words:

Victim of your own imagination
The dream has become a nightmare
Guilty as charged, moral abuse

So much of who I am lives in the future, and I've had to learn and improve how I live in the present moment. Today, there is a strong correlation between my ability to be consciously in this moment and my general sense of happiness, contentment, connection, and meaning.

I still imagine that future state, though. I have ideas, dreams and unknowns that I'm curious about.

As an entrepreneur, I have also learnt how to distil that dreamy future state into the next three steps I need to take to start progressing. Venturing into the unknown, I have successfully turned an idea into reality.

One of the ways I do that is by really investing myself into the thing I'm working on or doing. I do the same in my relationships. I wear my heart on my sleeve. WYSIWYG. Vulnerability is a natural and comfortable state for me.

And, when the world (where I don't exert control) throws a few curveballs, it's hard not to feel like the dream has become a nightmare. It's hard not to feel captured by my imagination.

I'm still figuring this out. And maybe I'll imagine a version of the truth that calms this enquiry for a new season of life.

In the meantime, I'll meditate on this:

“But who is the thinker—this thinker who has all these thoughts?” Is there a thinker at all, or only thought which puts together the thinker?"

- Jiddu Krishnamurti, The Only Revolution

I touched on a bit of this here. The last few weeks since joining Automattic to work on “commerce things” (I’ll keep teasing), I have reconnected with so many friends in the greater WordPress space.

It has been both fun to see a little bit of banter come to life on Twitter (I am holding off on calling it X, because it feels odd):

The interesting part of this is that the ~17K followers I have on Twitter is very similar to the amount of followers I had 10 years ago. My audience was entirely WordPress- and Woo-focused in the early days of my Twitter account, and even though I did so many other things beyond that community in the past 10 years, the size of my audience has not changed.

What’s been interesting is not the size of my audience, but instead seeing familiar names and faces pop into my stream. The same was true of the email newsletter for my previous newsletter: it was the most-read email I had sent in the last couple of years.

There is something to be said about coming home.

Ten years later, home is different to the one I mostly left. But some things and people have stayed the same.

I’m fully immersing myself in updating my understanding of home, and reconnecting with those that have kept the torch burning.

I’m excited to contribute, and maybe bring a few fresh ideas we should explore.

(I’m sure if Small Potato was still around, we’d argue about these ideas and 20-something Adii would be in the comments section of every blog to pour fuel on the flames.)

There are some changes I'm implementing here, and to signify it, I'm borrowing the title of Steve Biko's book "I Write What I Like" because it left such an immense impression on me.

This is one of my favourite quotes from the book:

"...the most potent weapon in the hands of the oppressor is the mind of the oppressed."

I made a mistake years ago (circa 2009). I updated my WordPress blog (I needed a change), and it was hard to migrate all the content. So, I optimised for "new" and not history. I truly regret that. (Most ironically, I had pushed my open source content to Facebook, which remains the only artefact of my writing before this switch.)

I return to that, because part of me feels like I'm in a "full circle"-type moment.

I have recently joined Automattic (1 January 2024) to work on commerce stuff (I'll keep y'all guessing because: hype). Even though I had left Woo before their acquisition by Automattic, this is still a homecoming of sorts. I'm reconnecting with so many ideas and individuals that have been influential on my journey.

Matt is a prominent protagonist in my journey. I'm late to his call to blog to celebrate his recent 40th birthday, and here is an overdue post. After that, I was fortunate to spend time with him in person for the first time since 2012. His passion for publishing and sharing has only grown since he first convinced me (and us) to change our stance about open source at Woo way back in the day.

With all this, I've been reminded that I used to publish/share whatever mattered to me. And I've been filtering and editing myself extensively since.

I was recently asked about "how I escaped" (sic, the corporate game) by someone following me for years. My reply surprised me. I replied that I felt way freer when I started this journey than now. I have imprisoned and limited myself in what I should do and publish. (Beyond publishing, we should discuss my decision to pursue a role at Automattic versus doing what I've always done: just start a new business.)

There is more to this conversation; in the meantime, I will try writing about what I like. Things like this. Or finally publishing the 70K words I wrote to tell you about the messy middle. I hope that by consistently sharing the things that matter to me, I can give you something from which you can extract value.

At some stage, I'll also probably have to switch my site (which is limited because I'm back to using a $100 template) to WordPress** to align with where I spend my time. For now, the platform matters less than the intent and the words.

The emails might be coming thick and fast (assuming I share well) in the next few weeks. I'd love some feedback, though. What resonates? What works? What else would you like from me?

And if you haven't made the connection yet: I have oppressed myself in this regard. The italics are important because this is not real oppression relative to what happens in the world, and the challenge has been one I've struggled with for years.

If I relented to that oppression, then I'm also giving power to the oppressor of any idea or technology or politic or world view. Instead, I'm aligning with and ambitiously pursuing the mission of Automattic, which is to democratise publishing and commerce (and now messaging).

It has to be a "hell yeah" or no.

And in this season of my life, I will write what I like.