“What will you do when you get there?”

On one of those mornings with cloudy skies, as they always do in London, “Lady K” asked me a question that stumped me. I spoke about what I had learned about investing, how much work it is, and how complicated things can get, and she flatly asked me, “What will you do when you get there?”.

I had mentioned that I’d like to have a great time when I retire and that, ideally, I’d retire at 50. Aren’t we all having the same dream? Retiring that early may be a pipe dream, but the question compelled me to rethink my current position and what will happen if or when I do get to retire.

Questions are hard. It’s hard to come up with questions to ask, and it’s hard to find the proper answer to any given question. Questions force me to think; they stick in my mind for a long while.

On the other hand, answers are like biscuits served on a platter: I can gobble them up like crazy and never get enough of them, but that doesn’t mean I will retain anything other than fat in my body and noise in my brain.

In time, I learned to ask and love questions. In my software engineering work, I consider myself The Questionator, the Master Questioner. For every task we have to work on, I like to unpick all the aspects of the requirements until we arrive at a good enough understanding. Are we making the best decision for the customer here? Are we considering the bigger picture? Do we have enough resources to handle the workload?

After I started investing, I wondered how to get the same principles and ideas into my investing world and gain some traction in my portfolio.

One of the ways I use to bridge the gap between domains is to make use of questions. In investing, you need a curious mind, and thankfully, I have sacks of curiosity lying around to use. Questions help me get from “nothing” to “something”.

My curious mind will not let me accept the rules and ideas behind domains I’m interested in without understanding their “why” and “how.” I will ask and challenge any assumption about investing, no matter how small, until I understand it. I was intensely against share buybacks until I understood that the fewer shares remain, the more dividends get to the remaining shares.

In the last several years, I have learned to be more patient and to allow the process to run its course, not to set unrealistic expectations, to allow any questions to arise, and to allow time for me to find the proper answers.

Since discovering investing a couple of years ago, I read more than 100 books about investing and anything remotely related to investing. I was doing this hoping to find the answers to endless riches, good investing frameworks, and fabulous returns. During this time, questions would pop up in my mind, and I ignored them because I didn’t want questions; I wanted answers.

Rory Sutherland proposes in his book “Alchemy” to look at things from different perspectives, to ask the questions nobody thinks to ask because they are too pedestrian, like “Why do people like to stand in a train?”. Another conjecture he presents in his public talks all over the internet is that people have difficulty taking knowledge from one domain and applying it to another. Questions and getting knowledge from one domain to another: that is what I started doing a while ago when asking questions and copying approaches from software engineering to investing.

When researching a company, I check the website, official reports, and data from different aggregators. In the past, all this reading targeted uncovering answers about the company’s health, economic moat and management. Now, I am reading, hoping that questions will start popping up in my head. The more, the merrier: why are directors related to each other, why are there so many contingencies in the yearly report, and how will they pay the increased dividends when I notice that the profit and cash flows are down?

Questions have a liberating factor: They remove you from a state of gobbling up answers like a mindless machine and push you into a state of thinking, reflecting on the nature of the domain itself.

What will I do when I get there? I plan to continue doing what I started: waking up in the morning, drinking my coffee, reading some interesting books, and dutifully investing in high-quality companies until the end of time.

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This article has been first published in SIGnet Newsletter – February 2025 | Issue 62.