Sometimes an opportunity is obvious. A job is advertised, somebody offers you a promotion, a customer asks whether you can provide a new service, or an investment appears with the potential for a good return. You recognise the opportunity because somebody has effectively put a sign above it saying OPPORTUNITY.
The more interesting ones don’t always arrive like that.
Sometimes exactly the same situation is visible to everyone, yet one person sees a possibility that nobody else seems to have noticed. Nothing new has appeared and no special invitation has been issued. The difference is simply that one person has looked beyond what is supposed to happen next and asked whether something else might be possible.
One of the biggest changes in my own career began with exactly that kind of moment, although at the time it didn’t feel particularly profound.
It was a Friday evening in London, my three-month employment contract had officially finished, my colleagues had organised leaving drinks to say goodbye, and everybody assumed I would soon be travelling around Europe before eventually returning home to New Zealand.
There was just one problem. I had decided I was going back to work on Monday.
I had arrived in London during the 1990s and managed to land my first serious IT contract in the Canary Wharf banking district, helped enormously by my best friend Garry, who was already an exceptionally talented IT professional who had helped get me through the door.
For someone from New Zealand, the money was extraordinary, especially when I mentally converted everything back into New Zealand dollars. But the conditions of the contract couldn’t have been clearer. My contract was for three months. I had a defined job to perform, a defined period in which to perform it, and when those three months were finished I was expected to leave.
My manager was unusually relaxed about the working day. He told me that once I had completed everything assigned to me, I was free to leave. There was no expectation that I sit at my desk pretending to be busy simply because other people were still working.
It sounded like an excellent arrangement, and for someone spending their first months in London it would have been very easy to take full advantage of it. Finish the day’s work early, disappear into the city, enjoy the pubs and nightlife and, once the contract ended, use the money to travel around Europe.
There would have been absolutely nothing wrong with doing that.
But fairly quickly I realized I wanted something different from those three months. Garry had helped create an opportunity for me that I probably wouldn’t otherwise have had, and I didn’t want to leave London having simply earned some good travel money.
I wanted to leave knowing considerably more than when I arrived.
My final Friday arrived and my colleagues kindly organized leaving drinks at a nearby pub, where the conversation naturally turned to what I would do next. People wanted to know where I was travelling, which countries I intended to visit and when I expected to return to New Zealand, because as far as everyone was concerned the story was already complete. I had come to London for a three-month contract, those three months had passed, and now I would collect my final pay, say goodbye and move on.
There was nothing unreasonable about that assumption, because it was exactly what was supposed to happen. What caught my attention that evening, however, was that my manager wasn’t there to say goodbye. There had been no final conversation about leaving, no farewell and, more importantly, nothing that gave me the impression anyone was particularly concerned about making sure I disappeared once the contract date had passed.
Sitting in the pub, I began wondering what would happen if I simply came back on Monday.
When I mentioned the idea to my now ex- colleagues, the reaction was immediate: I couldn’t do that because my contract had finished. They weren’t being negative or trying to hold me back; They were simply stating what seemed completely obvious to everyone in the room. The contract was for three months, the three months were over, and therefore I had to leave.
But when I asked why I couldn’t come back, nobody could really take the explanation much further than that.
That distinction stayed with me over the weekend. There was no question that my original contract had reached its end date, but I began to wonder whether we were all attaching another conclusion to that fact without really knowing whether it was true. Perhaps the opportunity genuinely was over and I would arrive on Monday only to be told to go home, but after everything I had learned during those three months, I wasn’t particularly interested in walking away simply because everyone assumed that was the next logical step.
So on Monday morning I put my suit back on and returned to my Canary Wharf workplace. When I reached the security entrance, I presented my access card and waited to see what would happen. The card worked, which was the first moment of relief, and after making my way upstairs I tried logging into the computer, which worked as well. I sat down, started working and waited for somebody to notice that the contractor who had supposedly left on Friday was sitting at his desk again on Monday.
Nobody stopped me.
What happened next was almost strangely uneventful, but that was precisely what made the experience so memorable. Something that had seemed like an unquestionable ending only a few days earlier turned out not to be quite as definite as everyone had assumed, and my three-month stay eventually became closer to a year.
Everyone told me I couldn't do it. When I asked why, no one had an answer.
Looking back, I don’t think the lesson is that people should ignore contract dates, turn up uninvited at former workplaces or assume that formal boundaries don’t matter. There are plenty of contractual, legal and organisational restrictions that are completely real, and in different circumstances my Monday morning experiment could easily have ended with someone politely showing me the door.
What mattered was that I had begun to recognise a difference between the things I actually knew and the conclusions I had simply assumed followed from them. I knew my three-month contract had reached its end date, but whether there was still a place for me inside that organisation was a separate question, and instead of automatically treating the expected answer as the actual answer, I decided to find out.
Returning on Monday created an opportunity, but it also created a problem I couldn’t afford to ignore. I was still relatively junior, I was being paid extremely well and, as my unexpected stay continued, I became increasingly aware that people with considerably more experience than me could reasonably question why somebody at my level was still occupying such a valuable position. Simply continuing to turn up wasn’t going to justify my presence indefinitely, so if I wanted the opportunity to last, I needed to find ways of becoming more useful.
Around the same time, management had a recurring problem of its own. Every Friday they needed two people to volunteer for mundane physical work on the trading floor the following day, and understandably there was rarely much enthusiasm from people who had already worked a full week and had better things to do with their Saturday.
On the surface, there was nothing attractive about this work, and I didn’t suddenly discover some hidden passion for giving up my weekends. What I recognised was that management had a problem nobody particularly wanted to solve at exactly the same time that I had a problem of my own: I needed to demonstrate that keeping me around provided value beyond the relatively junior work I had originally been hired to perform.
So I began volunteering, and before long I was doing it almost every week, eventually working six days a week for much of the year I remained there. The Saturday work itself wasn’t glamorous and it contributed relatively little to my technical education, but that wasn’t why it mattered. Its value came from the fact that something everybody else understandably regarded as an inconvenience happened to solve a problem that was important to me.
The situation taught me something I didn’t fully appreciate until much later. Opportunities don’t always become visible because the circumstances themselves change; sometimes they become visible because you recognize a connection between two things that other people are viewing separately. My colleagues saw an unwanted Saturday shift, management saw a recurring staffing problem, and I saw a way to make myself more valuable. We were all looking at exactly the same situation, but we weren’t necessarily seeing the same thing.
By the time I eventually left London, roughly a year after arriving for what was supposed to be a three-month contract, the experience had changed the direction of my life. I had learned far more than my original role required, accumulated experience I would never have gained if I had treated my job description as the boundary of what I was there to learn, and developed skills that eventually helped take me to Tokyo, Hong Kong and Sydney, where I continued working in major investment banks.
Author working in Tokyo, Japan
It would be easy, with the benefit of hindsight, to turn all of that into a neat story about recognising opportunities and deliberately engineering the outcome, but that wouldn’t be true. Luck played a part from the beginning. Garry helped me get through the door, I happened to find myself inside an environment where there was an enormous amount to learn, my manager gave me unusual freedom once my assigned work was finished and, when I returned after the contract ended, my security card happened to still work. Any one of those things could have been different.
What I did have some control over was how I responded to the circumstances once they existed, and that is where I think the more useful lesson lies. The free afternoons could have been interpreted as leisure time or as access to people who knew far more than I did. The end of the contract could have been interpreted as an instruction to leave or as a reason to find out whether another possibility existed. The Saturday work could have remained an inconvenience or become a way of solving my own problem of demonstrating value.
In each case, the opportunity wasn’t hidden because nobody else could physically see what was happening. Everyone could see the same free afternoons, the same contract end date and the same unpopular Saturday work. What differed was the interpretation attached to those circumstances and, particularly, whether the first interpretation was accepted as the only one available.
That is why finding hidden opportunities is less about constantly searching for some extraordinary opening nobody else has discovered and more about becoming alert to situations that may contain possibilities beyond their obvious purpose. We become very good at attaching automatic conclusions to circumstances: a project has finished, so we move on; something falls outside our job description, so we ignore it; nobody has asked us to learn something, so we assume it isn’t relevant; an unpleasant task appears, so naturally we avoid it.
Often those conclusions are perfectly sensible, but they are still conclusions, and occasionally there is considerable value in separating what the situation actually requires from what habit tells us should happen next.
There is an important limit to this way of thinking, because questioning assumptions is very different from assuming that every boundary exists merely to be challenged. Contracts matter, laws matter, safety requirements matter and other people’s rights matter, while organisations have legitimate rules that cannot simply be ignored because we would prefer a different outcome.
Independent thinking therefore isn’t about developing a reflexive distrust of rules. It is about becoming better at distinguishing genuine constraints from the assumptions that often accumulate around them.
My contract had ended, and nothing I thought about could change that fact. What turned out to be less certain was the assumption that the end of the original contract automatically meant there could be no further opportunity for me inside the organization. By separating those two things, I was able to test the assumption without pretending the underlying reality didn’t exist.
The same distinction appears in many areas of life because we constantly encounter situations in which everyone seems to know what happens next, largely because that is what has always happened next. Once an interpretation becomes familiar enough, it can begin to acquire the authority of a rule even when nobody can clearly explain where that rule came from or whether it actually applies.
That doesn’t mean the assumption will always prove wrong. Quite often, once you question something properly, you discover there is a very good reason for doing things the established way. The value is not in proving the conventional answer wrong; it is in recognising when you have mistaken an assumption for a constraint without ever examining the difference.
The same kind of thinking appears repeatedly in business, where some of the most valuable opportunities have emerged not because somebody began with a brilliant plan, but because they paid attention when reality started pointing somewhere different.
William Wrigley Jr., for example, wasn’t originally building a chewing-gum business. He began selling soap and later baking powder, offering chewing gum as a promotional premium, only to discover that customers were becoming more interested in the gum than the product it was supposed to help sell. The obvious response would have been to keep improving the original business while treating the giveaway as exactly that—a giveaway. Wrigley instead paid attention to what customers were actually telling him and eventually made chewing gum the business.
Play-Doh followed an even stranger path. The material that generations of children would eventually squeeze into brightly coloured shapes began life as a product designed to remove soot from wallpaper. As cleaner heating reduced the need for it, the original market began disappearing, but the product itself hadn’t suddenly become useless. Its value was simply somewhere else. After it began being used by children for modelling and classroom activities, what looked like a declining cleaning product was eventually repositioned as a toy.
Instagram offers a more recent version of the same pattern. Its founders originally developed a much broader app called Burbn with several different features, but noticed that users were particularly interested in sharing photographs. Rather than remaining committed to everything they had originally intended the product to become, they stripped much of it away and concentrated on what people were actually using.
These businesses were very different, and none followed exactly the same path, but there is a useful connection between them. The opportunity became visible when somebody paid more attention to what was actually happening than to what was originally supposed to happen.
That is remarkably close to what happened during my year in London. The chewing gum was supposed to support the main product, the wallpaper cleaner was supposed to clean wallpaper, Burbn was supposed to be a broader application, and my three-month contract was supposed to finish after three months. In each case, the original purpose was real, but treating that original purpose as the only possible future would have hidden what was beginning to emerge.
When we talk about opportunity, we often imagine something arriving from outside: somebody offers us a better job, introduces us to the right person, presents us with an investment, brings us a customer or gives us the break we have been waiting for. Those opportunities are easy to recognise because somebody else has already defined them for us.
The opportunities that are easier to miss are often sitting inside circumstances we think we have already understood.
That was ultimately what happened to me in London. I didn’t discover a secret position nobody else knew existed, and I certainly didn’t arrive with a carefully constructed plan that would eventually take me through investment banks in several of the world’s major financial centres. I had simply found myself in a valuable environment and, at several important moments, resisted accepting the obvious next step without first asking whether another possibility existed.
Sometimes that question leads nowhere. A contract really is finished, a door really is closed, a restriction exists for a very good reason or the extra effort simply isn’t worth what might come from it. Independent thinking doesn’t guarantee that another opportunity is hiding behind every assumption.
But sometimes there is enough uncertainty to make the question worth asking, particularly when everyone seems completely certain about what must happen next but nobody can explain much beyond “that’s just how it works.”
That is where some hidden opportunities begin—not with a brilliant idea or a carefully prepared invitation, but with somebody noticing that the situation in front of them may contain more possibilities than its conventional interpretation suggests. I certainly didn’t know any of that as I stood at the security entrance in Canary Wharf on that Monday morning. I only knew that everybody had told me the opportunity was over, while nobody had been able to give me a particularly convincing answer when I asked why I couldn’t return.
So I tried the access card … the security door opened for me, and what had looked like the end of a three-month contract became the beginning of an entirely different career.
Many of the opportunities we miss are not hidden because they are impossible to see, but because we have already accepted an interpretation of the situation that tells us there is nothing more to look for. Learning to notice those assumptions doesn’t mean ignoring genuine boundaries or breaking rules for the sake of it; it means becoming more deliberate about separating what is actually fixed from what everyone merely expects to happen next.
That distinction sits at the heart of NoRuleBook. The objective is not to reject every established path, but to become more conscious of the assumptions shaping your decisions and more willing to question them when the circumstances justify it.
If you want to explore how those unwritten rules and assumptions influence your own choices, click the NoRuleBook image below to get your copy.
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