For one reason or another, this question has been coming up in conversation a lot over the last few months. Whether it’s the pace of life under lockdown or the general uncertainty of the times, people are trying to figure out their futures, searching for answers to long, lost questions about what they really want and how they want to do it. And for a lot of us — read: most of us — that process is really, impossibly, terrifyingly hard.
So while it’s been tough to see friends going through the emotional process of finding clarity in their lives, having these conversations has also provided the opportunity to distill my thoughts on the subject and develop a bit of a theory around it.
This essay is not about how to pick a career, or what’s worth your time (though you should check out this essay if that’s what you’re looking to solve) nor does it cover the concept of IKIGAI (though it’s a useful concept that you should understand if you’re exploring this topic). It’s mostly about how the process of thinking through these types of big questions can generate cognitive fallacies, and what we can do to limit this from happening. More like: how to think about thinking about the problem.
I hope it’s helpful.
Finding #1: Beware of problem jumbling.
When people try to think about their future, a lot of different things come up. There’s your idea of who you are and what you were meant to do, your expectations about how much money you need to make, your sense of what’s important in the world, your ego’s model of what you need to be happy…just to name a few.
While these things are important to understand and are worth grappling with on their own, the brain has a nasty habit of combining them. It creates, for lack of a better word, mega-problems: giant blends of inter-related problems that work together to create one big cluster-fuck of confusion. In systems theory, these are called “wicked problems.” It can look (and feel) a bit like this:
When framed as blended clusters, mega-problems are nearly impossible to solve. Each issue swirls around with all the other ones, making it difficult to notice what is specifically bothering you, how it relates to the other issues, and what’s at stake. Plus, because they are inter-related, the feeling of confusion is compounded when a new piece of information comes up to spoil the equation you’ve developed in your head. One minute you’re set on starting a business selling Chinese socks to millennials; the next you’re planning a music career.
This way of thinking can be described as a category error. The question “what am I going to do next?” seems to demand an answer that can be filled in with this type of answer: [INSERT PROFESSION]. Your brain thinks: to solve the master problem (what am I going to do next?), I need to find the ONE answer that magically solves all of the relevant sub-problems.
But it can’t.
And the reason is simple: underneath the very tactical question of what to do is a giant iceberg of emotion and pathological reasoning that connects everything from your 4th-grade math class to the meaning of the cosmos. You think that you’re answering a question about your career over the next few months, but really you’re confronting the way your mother’s early-childhood praise biased you toward a profession that you’re not sure if you even like anymore.
It can be very daunting.
Plus, every time you come up with a potential solution to the master problem, you are quickly confronted with another set of reasons why it doesn’t provide a complete answer. “Investment banker” because ‘money’ and ‘global worldview’ quickly descends into, “but I hate suits, and I’m not very good at math.” “Chef” because ‘creativity’ and ‘hospitality’ turns into “but more school and low pay.” The search continues.
The result is a form of reasoning that can best be described like this:
The spin of death. The different compartments of the problem refuse to work together, and they send your brain into a tailspin that makes problem-solving even harder. If you’re anything like me, your instinct when this happens is to work even harder.
More research. More reflection. More compulsive discussions and self-talk. An acceleration that makes the whole process harder to control and more volatile. You’re up at 3 AM thinking about your future, then you’re taking mushrooms and meditating on your heart chakra. You’re hyped up and telling everyone you’re going to be a film producer, then you’re watching Netflix and wondering if you should apply to CSIS and become a spy.
Seldom do you ask: is it possible that the problem stems from the way I’m asking the question in the first place?
Finding #2: Match the solution to the problem.
The issue with the approach described above is that it blends distinct problems into one mega-problem. It weaves together ‘why do I care so much about being rich?’ with ‘how do I meet the right people to get a specific job?’. It commits a category error.
The way out of this problem, in my experience, is to get clear on what are the individual sub-problems, and begin the work of solving for each of them separately. And when you do, you will notice that each of the sub-problems require different types of solutions. You must design the solution from the perspective of the problem.
Typically, the sub-problems fall into these categories:
(1) Desire/Values Problems: ie. what do you actually want? what is worth pursuing? what do you care about? to what extent does your behaviour correspond to your stated values?
(2) Emotional Pathology Problems: ie. what does your ego want? what stories are you telling that limit or shape your self-vision? where do these come from? how are the expectations of others shaping your model of what’s worthwhile and attainable?
(3) Habitual Behaviour Problems: ie. how are you treating your body? do you give yourself space for relaxation? are you kind to yourself?
(4) Opportunity Generation Problems: ie. what do I need to get what I want? who in my network can open up opportunities for me?
(5) Expectation Framework Problems: ie. is my model of how the world works accurate? do my assumptions about the paths I’m interested in correspond to reality? how seriously should I take the advice of others?
Broken out this way, there are a few things to notice. The first is that none of these categories are particularly unique. Your life might be exceptional, and the matrix of variables distinct to your situation, but the types tend to be the same. In other words, get over yourself, bro.
The second thing to notice is that when framed in this way, the fallacies become super clear. An opportunity generation problem does not involve the same solution as an emotional pathology problem. A habitual behaviour problem does not involve the same solution as an expectations problem. Yet we often fail to notice the difference.
Let’s go one step further.
When people are stressed out, they tend to ignore their bodies, and they attempt to solve their problems with their mind alone. They become consumed in the work of figuring it out, and abandon the pursuit of feeling good in favour of being serious. The pain somehow makes it feel more real. But in the process, they distort their thinking and make things harder for themselves in the process.
Plus, if they’re asking this question, they also might not be working with other people. What working provides — beyond (hopefully) money and friendship and purpose — is a feedback loop that validates your sense of skillfulness through experience. You act, and the world responds. Your ability to create is reinforced on a daily basis. So when it’s taken away, it hurts.
It’s no wonder that people that are unemployed are far more likely to experience mental health problems. One study found that involuntary unemployment is worse for individual happiness than divorce or separation. It’s serious stuff. And it’s not a good combination with the seemingly black box of digital job applications.
Then, there’s all of the personal stuff. Humans are experts at deluding themselves, from what they want to why they want it. Even at the best of times, separating between what’s a genuine aspiration and what’s coming from a place of fear is tough. Compounded with the emotional tailwinds of burnout, anxiety, uncertainty, and poor health, the drama of understanding can quickly become a tragedy.
Identifying which action is causing which reaction is hard. So what to do?
Problem-matching continued
The point of separating things this way is to notice how different problems call for different solutions. Most of which should be managed one at a time.
Opportunity generation problems are mostly tactical, requiring a networking strategy and maybe some serendipity. Spruce up your LinkedIn, take an e-course, learn a new skill. Once you know what you’re aiming for, these things become relatively obvious.
Habitual behaviour problems are about checking in with your body. Exercise goes a long way to keeping your mind on track. Noticing how you feel and how it’s influencing your behaviour can make all the difference. Sometimes the solution is not to drudge through the weeds of your discomfort, but to stop altogether. Meditate. Read. Run. Laugh. Just because the problem is serious doesn’t mean you have to be upset while you’re dealing with it.
Expectation framework problems are mostly about research. It’s about humility in your understanding and flexibility in your mindset. What do you really know about the industry of interest? How many info-interviews have you set up?
Emotional pathology problems and Desire/Value problems are by far the most difficult. Our values work like a set of filters colouring the world we see around us. From what we want to what we ignore, they enable us to navigate through complexity and make choices. Whole volumes have been written on the subject, so I won’t go too deep into it here, but the role of values can’t be stressed enough. They are the conceptual map-making layer of our brains that allow us to model what exists and how.
Values problems require values solutions. Checking in with yourself about how the things you care about support or contradict each other can be rewarding. Examining them carefully can reveal areas of internal conflict and nubs of clarity. Writing them out all the way can be helpful.
Pathological problems are about modes of thinking and doing. If we think of the brain as a pattern-recognition machine, with fleeting thoughts on the outer edges and values closer to the core, our pathologies are like the dense, inner layer where mental habits have congealed into scar tissue. They’re what happens when ways of thinking and acting are integrated into the operating machine without us noticing, shaping our actions and thoughts in subtle but persuasive ways.
I won’t pretend to be an expert on the subject, but simply being aware of how these repeated patterns affect our actions is difficult but rewarding work. Sorting through them requires a lifetime worth of reflection. Observing what comes up when you’re planning the direction of your career can serve as a useful lens for examining these patterns.
Another crucial thing about these problems is that they cannot be solved with any version of this equation:
First I’ll become an [INSERT PROFESSION] and then I’ll be [INSERT LASTING POSITIVE EMOTION].
The tendency to look for external solutions to internal conflicts is one of the most common fallacies that humans commit. We do it in relationships. We do it with objects. We do it in our careers.
The temptation to think that a form of external validation — be it money, or status, or fame — will solve our internal problems is constant. Every fairytale warns against it. It’s the moral of every great story. And yet, we continue to forget it.
The point of the observation is not that it’s all in your mind or that we’re all vapid hedonists. It’s not that some great transformation is needed, or that you have to meditate yourself to Enlightenment. The point is that because our consciousness is formed in symbolic conversation with the (m)other, we often look outside of us for mostly personal answers. We solve a ‘me’ problem with an ‘it’ solution.
This does not mean that every issue can be solved by turning inward. Many cannot. But it does mean that when it comes to our professional lives, the ability to distinguish between what is a tactical problem and what’s an emotional one can be useful.
Clear thinking requires bravery and patience and honesty. It requires discipline, and awareness, and intellectual humility. It requires looking at the things that arise in our minds with both an acceptance and a critical lens. And it means taking our time.
But it also means allowing ourselves to act without the complete, perfect solution.
Finding #3: Use ‘good enough’ solutions.
The risk of descending into the steep basement of self-knowledge is that the depth is nearly endless. The more you learn about yourself, the more you realize how little you know. So if you’re not careful, self-reflection can be paralyzing. That’s why it’s important to remember that the solutions are never — and will never be — complete.
There is no final answer.
As it relates to a practical question like ‘what am I going to do?’, it’s easy to get caught up in the minutia of salary concerns or the endless pit of early childhood experiences. The point is not that these considerations aren’t important, or shouldn’t be worked on. Much to the contrary, these questions are an essential pre-requisite to acting with any degree of certainty.
The point is that the ability to distinguish between what needs work and what is good enough is key. You don’t need to figure out why your mom thought you should be a lawyer so long as you can recognize that her perspective is not the final say. You don’t need to solve your imposter syndrome as long as you can put yourself out there when you step into your next job interview.
Finding #4: Do the work.
When it comes to our personal lives, most of us are pretty bad at taking our own advice (myself included). We may be introspective and analytical. We may be critical and self-aware. But when it comes to applying rigorous thinking to our own lives, we almost always fall short.
The reason is simple: it feels weird.
When it comes to our professional lives, we know that spreadsheets and frameworks and research are essential. We’ll whiteboard and brainstorm all day when it has to do with a client, but when it comes to our personal lives, the same approach feels weird and awkward. Building an OKR framework for your life takes away from the spontaneity and intuition of just living. It makes the most romantic discussions about the meaning of life into formulaic models. It feels icky.
Some of the best advice I ever received was to treat myself, and my ambitions like I would treat a client. As a consultant, most of your job is about clarifying the thoughts of other people and framing it back to them in a way that allows for new learning and growth. Most people are great at giving advice but bad at taking it.
Doing work on ourselves is more than just having honest conversations (though that can help). It’s not about seeing a therapist (though you probably should). Doing work on ourselves is about doing the work. It’s extracting the things we need to work on from our brains, and laying out a plan for how we’re going to do it. It’s not sexy. Most of the time, it’s highly mundane. But part of radical self-responsibility is about doing the boring stuff so that when we come back to the big questions, we have the muscle memory to think them through. Part of this is about being honest and holding ourselves accountable. But most of it is about clarifying what’s actually going on.
It’s about separating between what is real and what is a fabrication.
And in my experience, the only way to do this successfully is by hunkering down and doing the work. Literally, writing everything out and solving for it piece by piece. Finally understanding yourself and seeing it all on paper can be very relieving.
Conclusion
Articles like this one tend to make the process seem simple and direct. The idea that you can ‘follow these steps’ and find the answer is tempting to believe, but it’s untrue. When it comes to complex problems, there is no silver bullet.
Nothing that I’ve written here is particularly novel, and I know it’s a lot harder in practice. But what makes this approach different from others is that it focuses on eliminating self-delusion more than doing some set of tasks.
And in my experience, working smarter is almost always better than working harder.
