Playing the Long Game
On being a generalist, making decade-long bets, and learning to commit to things that outlast the present.
I’ve spent most of my life avoiding the idea of doing one thing forever. Not because I have a problem with commitment, but because I’ve always found something unsettling about the possibility of spending decades pursuing something I might eventually lose interest in. Throughout my teenage years and 20s, I moved between professions, industries and interests, often convinced that whatever I was doing at the time would become my life’s work. Then I’d discover something that made me reconsider, and the cycle would begin again.
But I’ve recently started questioning whether I’ve misunderstood what it means to play the long game. Perhaps long-term thinking has less to do with staying in one profession, working for the same employer or even building the same company for decades. Perhaps it’s about making deliberate bets on things you believe will matter in the future and allowing those convictions to shape how you spend your time, develop your knowledge and make decisions today.
The interesting thing is that we’re already making long-term bets, often without recognising them as such. We make them through our religious beliefs, the philosophies we inherit, the people we marry and the families we choose to build. Some of these decisions shape the rest of our lives, even though we cannot possibly know how they’ll turn out when we make them. Yet when it comes to our professional lives, many of us struggle to think beyond the next opportunity, promotion or business idea.
As I’ve entered my 30s, I’ve become increasingly interested in what would happen if I approached my ambitions with the same willingness to think in decades rather than years. Not by abandoning the curiosity that has made me a generalist, but by giving that curiosity a longer time horizon.
The Generalist’s Dilemma
My first serious attempt at figuring out what I wanted to do with my life came after secondary school, when I spent about six months learning photography and videography through an apprenticeship. I enjoyed the work and initially thought I had found my future. But I was growing up in a part of Lagos that I desperately wanted to leave, and the opportunities available to me seemed limited to the immediate environment. I could imagine myself becoming a photographer, but I struggled to imagine the life I wanted emerging from the opportunities I could see around me. I was ambitious, although I didn’t necessarily understand what that ambition meant at the time. I simply knew that I wanted a different life, and I wasn’t convinced that the path I had chosen would take me there.
I subsequently tried to gain admission to university to study law but wasn’t selected. It was a painful disappointment, and I eventually went on to study journalism, completing a two-year diploma. Since I already had some experience with photography, I thought photojournalism would be a natural progression. I spent time photographing major events, covering interviews and observing journalists who had been working in the profession for years. The experience was exciting at first, but it also exposed me to things that changed my perspective. Many of the journalists I encountered were struggling financially. Some were owed salaries for months, and I saw how financial insecurity could make journalists vulnerable to the influence of money, including the familiar practice of accepting brown envelopes from people they were supposed to report on independently.
I remember observing these people and wondering whether I wanted to spend the next twenty years living under similar conditions. These were professionals who had dedicated substantial portions of their lives to journalism, yet many of them were struggling to earn a decent living. I didn’t necessarily think they had made the wrong career choices. Rather, I was beginning to understand that loving a profession and wanting the life that comes with practising it are two different things. I had entered journalism because I was interested in the craft, but the longer I spent around journalists, the more I began questioning the economics of the industry itself.
Print journalism was already under pressure, and the transition to digital publishing was creating a different set of problems. Many traditional publishers were struggling to adapt, while online publications increasingly depended on technology companies such as Google and Facebook for traffic, distribution and advertising revenue. It seemed peculiar to me that an industry responsible for producing information could become so dependent on other companies to reach the people consuming it. Years later, the Reuters Institute’s Digital News Report 2025 would document how digital platforms continued to reshape news consumption and undermine the economics of traditional publishing. These developments reinforced some of the concerns I had encountered much earlier in my career.
My exposure to online journalism eventually sparked an interest in technology. By the time I went on to study English literature at university, I was already exploring opportunities beyond traditional media. What attracted me was the possibility of understanding the systems and platforms that were changing the industries around me. I didn’t have a particularly sophisticated thesis about technology at the time. I was simply curious, and curiosity had become the recurring force behind many of my decisions.
That pattern continued throughout my 20s. I worked in large organisations and smaller companies, experienced roughly four layoffs, started companies that failed, and eventually found myself building technology products and selling solutions to enterprise customers. I’ve experienced the excitement of joining established companies and the uncertainty of trying to build something from scratch. I’ve also experienced how quickly a professional identity can disappear when an employer decides that your role is no longer necessary. After going through multiple layoffs, it becomes difficult to believe that a job title or employer should be the defining feature of who you are.
Looking back, I don’t think my problem was an inability to commit. Whenever I became interested in something, I generally threw myself into it. I spent time learning, experimenting and trying to become good at the work. What I struggled with was the idea of committing to a particular activity indefinitely, especially after discovering limitations I hadn’t anticipated. Sometimes those limitations were economic, sometimes they were personal, and sometimes I simply became interested in something else. But entering my 30s has made me question whether constantly reconsidering my direction might eventually prevent me from benefiting from the things that only become valuable after years of sustained attention.
There’s an interesting tension here. Being a generalist has allowed me to explore opportunities that might have remained invisible if I had committed to a single profession early in life. Yet the same willingness to explore can become a weakness if every new discovery leads to another change in direction. At some point, the question stops being whether there’s something more interesting to do and becomes whether the thing you’re already doing deserves more time.
We Are Already Playing Long-Term Games
I’ve always associated playing the long game with staying somewhere for a long time. You join a company, remain there for ten years, work your way through different responsibilities and eventually develop a career around that organisation. Or you enter a profession and commit to practising it for the rest of your working life. There is nothing inherently wrong with either approach, but I’ve never found them particularly appealing. They seem to require a kind of permanence that doesn’t sit naturally with my curiosity.
I’m beginning to think that understanding is incomplete. A long-term game doesn’t necessarily require staying in one place or performing the same activity for decades. It can involve choosing a belief, hypothesis or commitment that shapes a series of decisions over time. The activities may change, and the methods through which you pursue the commitment may evolve, but there is something underneath them that remains relatively consistent.
In fact, most people are already involved in several long-term games, even if they don’t consciously think about their lives in those terms. Consider the beliefs and philosophies we inherit from our families. Many people grow up with particular ideas about kindness, honesty, responsibility, religion, marriage and what constitutes a good life. Some of these ideas are passed down through generations, surviving substantial changes in technology, culture and economic circumstances. Others are modified as people encounter different experiences, question what they were taught or develop convictions of their own.
Someone might grow up believing that generosity towards strangers is a moral obligation. That belief could influence their behaviour for decades, affecting how they spend money, interact with people and respond to those in difficult circumstances. Another person might believe that personal independence is the most important condition for a fulfilling life. That conviction could influence where they choose to live, whether they marry, the work they pursue and how they organise their relationships. Neither person necessarily wakes up every morning thinking about the long-term implications of these beliefs, yet their choices gradually produce lives shaped by them.
Religious beliefs are another example. People commit themselves to Christianity, Islam, Hinduism and other religious traditions, sometimes for their entire lives. Their convictions influence everything from daily routines and personal relationships to their understanding of morality, death and the purpose of human existence. Many people inherit these beliefs from their parents, while others discover or adopt them later in life. In either case, religious commitment can provide a framework for decisions that extend well beyond the immediate circumstances in which they are made.
Marriage and parenthood make this even more interesting because they involve commitments whose consequences are both deeply personal and difficult to predict. When two people decide to marry, they are making a decision that could shape the next fifty years of their lives. They cannot possibly know everything about the people they will become, the challenges they will encounter or how their circumstances will change. They make the commitment despite that uncertainty, hoping that the relationship they build will remain worth sustaining through whatever happens.
Parenthood is an even more consequential example. Choosing to have children changes almost every aspect of someone’s life. It affects where people live, how they spend money, their careers, friendships, priorities and the amount of freedom they have to make spontaneous decisions. Parents sacrifice sleep, personal time and certain opportunities because another person’s wellbeing becomes part of their responsibility. The immediate experience can be exhausting, expensive and emotionally demanding, and there’s no guarantee that every sacrifice will produce the outcome a parent hopes for.
Yet I’ve heard parents, including my own, describe those sacrifices as worthwhile. They talk about watching their children grow, the relationships they develop and the fulfilment that comes from raising another human being. I find this fascinating because the rewards they describe often emerge over many years. The sacrifices happen in the present, while some of the most meaningful outcomes become apparent much later. A parent caring for a crying baby at three in the morning isn’t receiving an immediate return on that effort. They are participating in something whose significance extends far beyond the inconvenience of that particular night.
I’ve also seen the other side. I have friends who have difficult relationships with their parents, including some who believe their parents didn’t give them the attention, care or support they needed. I don’t know the full circumstances behind those relationships, and I wouldn’t pretend that every difficult relationship can be explained by poor parenting. Sometimes people make enormous sacrifices and still end up with strained relationships. Other times, choices made years earlier have consequences that become apparent only when children become adults. The important observation is that making a long-term commitment doesn’t guarantee a positive outcome. The quality of the decisions made throughout that commitment matters enormously.
This is one of the things I find most interesting about long-term games. We make consequential decisions without knowing how they will turn out. We commit because we believe something about the future, because we consider the commitment worthwhile, or because the values we hold make certain decisions meaningful regardless of their eventual outcome. Time becomes part of the process, but time alone doesn’t guarantee success.
My Faith Is Already a Long-Term Bet
My Christian faith is perhaps the clearest example of how a long-term belief influences my own life. I believe there is an afterlife, and I believe that the choices I make in this life have consequences beyond my time on earth. That belief is connected to how I understand justice, morality and the purpose of human existence. I find it difficult to believe that the world, with all its suffering, inequality and apparent randomness, can be understood entirely through the relatively brief lives we experience here.
This is a theological conviction, and I recognise that people from different religious and philosophical traditions will approach these questions differently. What interests me for the purpose of this essay is not necessarily proving the existence of an afterlife, but examining what happens when someone genuinely believes that their present decisions have consequences extending beyond their immediate circumstances. Such a belief changes how a person evaluates choices, because the relevant time horizon is no longer limited to the next few years or even their lifetime.
My faith influences where I spend my Sunday mornings, the people I choose to associate with, how I understand marriage, how I hope to raise my children and the way I try to treat people. It shapes my thinking about forgiveness, kindness, personal responsibility and what it means to live a good life. These are ordinary decisions, but they emerge from a belief about something much larger than the immediate circumstances in which those decisions are made.
Of course, describing faith as a bet has its limitations. Religious commitment isn’t simply a calculated wager in which someone weighs potential returns against possible losses. For me, Christianity involves conviction, worship, community and a relationship with God. But the language of long-term bets helps illustrate something important about how beliefs influence behaviour. A person who believes their choices have eternal significance may organise their life differently from someone who believes human existence ends entirely at death. Neither person needs to know precisely how their life will unfold for those beliefs to influence what they do today.
This raises an interesting question for me. If I can organise substantial parts of my life around a conviction whose ultimate fulfilment lies beyond my lifetime, why have I sometimes struggled to commit to other ideas for even five or ten years? Surely there are intellectual pursuits, professional ambitions and problems in the world that deserve sustained attention, even when their eventual outcomes remain uncertain.
I don’t think a professional hypothesis deserves the same kind of commitment as my religious faith. There are important differences between believing something about the nature of existence and predicting how a particular technology or industry will develop. But there is a useful principle connecting them. Our beliefs about the future, whether spiritual, philosophical or economic, influence the decisions we make in the present. If those beliefs are sufficiently important, they can provide continuity across years of changing circumstances.
What Would a Ten-Year Bet on AI Look Like?
Artificial intelligence provides a practical example of the kind of long-term bet I’m considering. We are living through a period in which AI capabilities are developing rapidly, new companies are emerging and organisations are experimenting with how the technology might change the way they operate. At the same time, there is enormous disagreement about what the future will look like. Some people believe AI will fundamentally transform the global economy, while others think current expectations are exaggerated and that much of the investment flowing into the industry will eventually prove unsustainable.
I’ve been thinking about this partly because of my own experience building AI products and working with enterprise customers. In the past few years, we’ve seen the public conversation evolve from large language models and chatbots towards reasoning systems, AI agents, multimodal models and increasingly sophisticated voice interfaces. Each development has created new opportunities and competing claims about what the next important application will be. Sometimes the industry moves so quickly that something presented as revolutionary six months earlier begins to look ordinary.
I experienced some of the excitement surrounding blockchain and cryptocurrencies, which has influenced how I think about technological hype. There was an enormous amount of enthusiasm, speculative investment and ambitious claims about how blockchain would transform entire industries. Some of the underlying technologies have found meaningful applications, but many of the expectations attached to the original wave of excitement didn’t materialise. The experience taught me that an interesting technology and a compelling narrative aren’t sufficient evidence that a particular business model or industry will succeed.
AI might also be experiencing speculative excess, and I don’t think that possibility should be dismissed. But I see a difference in the kinds of applications emerging, particularly in enterprise environments. Businesses are experimenting with systems that can handle customer interactions, process information, assist employees, execute workflows and support operational decisions. These applications still have significant limitations, especially around reliability, security, cost and integration with existing systems. Nevertheless, they address activities that organisations already perform and allocate substantial resources towards. That gives me reasons to believe the technology will remain economically relevant, even if many of today’s companies and products eventually disappear.
Suppose I decide to make a ten-year bet that AI will become an increasingly important part of how people and organisations work. What would it mean to take that bet seriously? It wouldn’t simply mean starting an AI company and hoping it becomes successful. It would mean organising several aspects of my professional and intellectual life around the hypothesis, while accepting that I cannot predict exactly how the technology will develop.
If I were looking for a job, I might prioritise opportunities that deepen my understanding of AI and its adoption. If I were building a company, I would look for problems where the technology could produce meaningful value. If I were developing an investment thesis, I might study the companies, infrastructure and industries likely to benefit from its development. I might build a publication where I write about what I’m learning, spend time conducting research and develop relationships with people working on important problems in the field.
Over a decade, these activities could reinforce one another. The knowledge gained from building products might improve my ability to evaluate companies. Working with enterprise customers might reveal problems that become subjects for research or writing. Publishing my ideas might introduce me to people whose work expands my understanding. An unsuccessful business could still produce valuable experience, provided I learn something that improves my subsequent decisions. I could change employers, start another company or move into a different role without necessarily abandoning the original bet. The continuity would exist in the knowledge, relationships and capabilities I was accumulating rather than in the name of the organisation employing me.
There is also an important distinction between betting on a technology and betting on a particular outcome. Someone might believe AI will become powerful enough to create substantial social risks and consequently dedicate the next decade to AI safety, governance or evaluation. Their work could involve questioning the claims made by AI companies or investigating the limitations of increasingly capable systems. They might be critical of the industry’s commercial incentives while still believing the technology deserves serious attention. Another person might be convinced that current expectations are unsustainable and spend years studying the financial or economic consequences of an eventual correction.
These people would be taking different positions, but each could be engaged in a long-term intellectual commitment. The important consideration is whether their beliefs are sufficiently coherent to guide sustained work and sufficiently open to evidence that the work remains useful when circumstances change.
I think there’s a danger in turning long-term bets into rigid identities. If I commit myself to AI for ten years, I shouldn’t have to spend the entire decade defending every assumption I held at the beginning. Technologies change, evidence accumulates and previously convincing ideas can become difficult to justify. A commitment to understanding AI’s impact is not the same as a commitment to believing that every AI company will succeed or that every application will deliver value.
Perhaps the better approach is to distinguish between the hypothesis and the activities that support it. I can remain interested in the future of AI while changing my opinion about which technologies, businesses or applications will matter.
Can a Generalist Play the Long Game?
One of the questions I’ve been asking myself is whether being a generalist makes long-term thinking more difficult. Specialists tend to have a clearer way of measuring their progress. Someone who spends twenty years practising medicine, studying a particular field of mathematics or working as an engineer can often point to a body of expertise accumulated through sustained practice. For generalists, the progression is less obvious because their experience may be distributed across several disciplines.
But perhaps this is precisely why long-term bets are useful for people like me. Without an underlying direction, curiosity can become a series of disconnected adventures. You learn enough about something to become interested, encounter its limitations and move on to the next opportunity. Over time, you accumulate experiences without necessarily developing anything that compounds.
The problem is not that the experiences are worthless. Photography taught me how to observe. Journalism taught me how to ask questions and investigate claims. Studying literature shaped how I think about language and ideas. Building companies has taught me about customers, technology, money, failure and the difficulty of turning an interesting possibility into something useful. These experiences continue to influence one another, even when the connection wasn’t obvious at the time.
A long-term bet can give those experiences a common direction. It allows a generalist to move between activities without treating every change as a complete restart. The question becomes less about maintaining a single professional identity and more about whether each activity is deepening the knowledge, relationships and capabilities connected to the commitment.
This doesn’t mean every interest needs to serve one grand ambition. Some things are worth doing because they are enjoyable, beautiful or meaningful in themselves. Not every book needs to support a thesis, and not every relationship should be evaluated according to whether it advances a professional objective. A life organised entirely around productive accumulation would become narrow in a different way.
But some ambitions require enough continuity for learning to compound. If I want to understand how AI changes organisations, build useful technology or develop an informed view about the industries emerging around it, I need to remain with the questions long enough to move beyond the excitement of discovery. That may involve several jobs, companies and forms of work. It still requires commitment.
Looking Back from Ten Years Away
I don’t know which of the bets I make today will still make sense ten years from now. Some will probably turn out to be wrong. Circumstances will change, evidence will emerge and I will change as well. Playing the long game cannot mean refusing to revise a belief simply because I have already spent years acting on it.
What I want is a way of committing without pretending to know the future. I want to choose a small number of ideas, problems and relationships that deserve sustained attention, then allow the work I do today to become part of something larger than the immediate opportunity in front of me.
My faith already works this way. It shapes ordinary choices through a belief about a future I cannot see. Family works this way too. People make sacrifices in the present because they believe the relationships they are building will matter across a lifetime. A professional or intellectual bet is different, but it can still provide a horizon long enough for knowledge, judgement and relationships to deepen.
I can remain a generalist and still play the long game. The commitment does not have to be to one employer, one company or one activity. It can be to a question worth following, a problem worth understanding or a belief about the future that is strong enough to guide action and humble enough to be revised.
Perhaps a decade from now, I will return to this essay and ask what these bets changed: where they took me, what they taught me and whether they were worth continuing. I may discover that I misunderstood some of them entirely. But I would rather make a considered commitment and learn from it than spend the next ten years repeatedly starting again.
A note on the writing process
This essay was developed through a collaboration between Samuel Adekunle and OpenAI’s ChatGPT.
My writing process begins with long, often unstructured spoken monologues in which I describe my observations, experiences, questions and developing arguments. I use ChatGPT to interrogate those ideas, challenge assumptions, explore research and help organise the material into a coherent essay.
The central perspective, personal experiences and conclusions are mine. Research, structure and editorial development are collaborative, and I take responsibility for the final published work.
The precise ChatGPT model designation can be added once verified for publication.
Sources
- Reuters Institute for the Study of Journalism. Digital News Report 2025: Executive summary.