When the student is ready

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 because the equity I received when I sold Conversio is worth materially less than the nominal value at which it was issued in August 2019.

On the surface, that sounds like an absolute trainwreck of all outcomes. That is how I initially felt when I got the news on Friday. I woke up quite a few times during my sleep Friday night, and I would immediately think about this and what to do next.

Part of this impact was probably softened because I had reluctantly accepted over the years that this money was not yet mine. I had tried multiple times to get better information about the value of my equity and explore creative ways to obtain liquidity. However, as a super minority shareholder on the cap table, I had no rights to information or liquidity.

Subsequently, I never did any financial planning with that money in mind, but I never wrote it off. Based on the dribs and drabs of information I received over the years, I would tell myself that the equity might not be growing but would at least hold its value. I even contemplated situations where it dropped by 20% or 30% and felt okay about that.

Looking at a fixed valuation on my portfolio spreadsheet and doing these mental acrobatics was a kind of financial memento mori. It was a half-baked attempt to acknowledge that any paper value can die.

But when Friday's news came, which was much worse than I ever expected, my suspicions and preparation were little solace.

Surprisingly, though, I'm feeling calm and emboldened. This feels less of a setback and more of an accelerant for a path I've already been on lately.

A Better Path

One of the most challenging seasons I experienced as an entrepreneur was building Conversio in late 2017 and early 2018 (you can get more of the colour and context here). I had made a mistake that meant we were not doing as well as we thought. I had to lay off two members and didn't pay myself for a few months. I felt incredibly stuck.

I felt responsible for the mistake, and I knew I was also responsible for choosing the path of entrepreneurship and building this business and this product. Everything was on me.

I fell into writing a lot of poetry at the time as a way to make sense of what I was experiencing. This is an excerpt from my book Motion:

Passing the mirror
Eyes lock with the villain
I know who chases me
It's hard when body and mind contradict
Heart arbitration
That often just feels passive
It sometimes reduces this chase to a simmer
Knowing it will boil over again

Later, when I wrote Life Profitability, I refined this perspective and made it even more real by naming the "who" that chases me:

My mental and emotional well-being was likewise not fantastic. I was under immense and constant stress. The ego beast was chasing me, telling me I couldn’t fail publicly. I struggled with that idea. But I couldn’t convince myself that all of those nice goals I’d set myself and the hopes I had for the business were worth pursuing if I had to endure continuing stress. And, because of business pressures, I felt isolated.

A big premise of my book was to acknowledge that having a beast (myself) chase me was a great motivator to keep pushing forward to be successful in business. I was also finally recognising the costs associated with doing just that, and I was exploring a different way of building a business—one where I wouldn't burn out because I was being chased by a firebreathing dragon.

I took that sentiment and goal with me as I started working on Cogsy. I was going to do this in a new way that optimised for all of the upsides of building a business while avoiding the many personal stressors and costs that come with it.

My desire had already shifted, but the practice and reality did not move as quickly. From early in the journey, my friend Marcella pointed out that I often described Cogsy as a slog. This from an email to her in July 2021 (a couple of months into working on Cogsy only) before she eventually joined Cogsy as Head of Marketing:

Cogsy has been interesting for so many reasons... It's also been slower and much harder than I thought to start up again. Big part of that is that I've learnt that I love the work less than I did in the past. ☺️ Launching publicly first week of August though, so time will be tell to what extent we've made progress.

I can admit now (probably because my clarity about this only came much later) that I was battling myself on a contradictory point: On the one hand, I yearned for those Conversio years when the beast was chasing me. The beast is tiring but an excellent forcing function for progress. But I had decided not to repeat sub-optimal patterns from my past, regardless of whether "it would work". The end would not justify the means.

And so the teacher appears

“When the student is ready the teacher will appear. When the student is truly ready... The teacher will Disappear.” - Lao Tzu (from Tao Te Ching)

When I heard on Friday that I had lost millions, my instinctive reaction was to use the loss as motivation to make more money (to fill the gap left). The significance of the loss would make for quite the beast that could chase me into this next season of life.

But as the dust settled, I didn't feel the same push or sensation of being chased. The beast is still there when I peer over my shoulder, but it is caged.

What I've felt instead is more of a pull into the future. A calling to something better and greater. An open invitation that is already in alignment with who I am.

It was tough for me to decide not to continue with Cogsy last year, and it was similarly challenging to admit that I was not ready to start a new business. These two decisions have already pivoted onto a different path from the one I had taken in the past, which was hopping from one venture to the next. I started building what would become Conversio only 3 months after writing this.

This path has sought clarity on who I am and what I value in this season of life. I started talking about connection and meaning much more. I scratched at my understanding of (my) identity and especially started thinking about who Adii was if he was not an entrepreneur.

Many hours of conversations with my therapist and executive coach have helped me reconnect to all of the parts of me. Today, I have an even greater awareness and understanding of what is most natural for me, and I'm confident that I'm the best version of Adii when I'm sticking closely to that nature.

I'll share a few one-liners to give you a directional sense of what that clarity looks like, but these are all probably interesting enough as individual blog posts:

I'm a better me when I'm building.

Money matters less to me than I thought. Flying First Class is incredible and didn't scratch any material itch.

I want to be involved in something bigger than myself, ideally in my community/society/country. Something where I have physical proximity and connection.

Recently, I've prioritised meeting people in person to seek connection (and meaning). Although I've had less time (due to the commute involved), this has been much more energising than Zoom calls.

I've reached out to strangers for help and have had fascinating conversations. It feels like I'm genuinely being curious and learning again.

Being a family man and showing up for my family is probably much more fulfilling than I considered in the past.

This means that I know that what comes next is to allow myself to be pulled into this future.

Fighting a financial loss and being reactive would invite an uncaged beast back into my life. And it would inevitably chase me down a path not aligned with this pull and calling I'm feeling.

I've been at similar forks in the road before. In the past, though, I lacked the calm, intentionality, or self-awareness to make a new choice (or, in homage to the old title of my blog, make a new mistake).

In recent months, self-work has empowered me to say no to the chase and instead lean into this new path I've already identified.

The financial loss is like shedding even more baggage and moving freely into the next season of life.

I don't know the exact next steps, and I'm still figuring that out. I know I have many options.

For now, I feel calm and clear because I am in alignment with myself and very present with all that is true in this moment.