On “What Should I Do?”

“What should I do?”

Many people ask me this question: aspiring entrepreneurs looking for advice on how to start a business, friends who don’t know how to proceed with a love interest or a career choice, employees asking how to best make a decision at our company, and even my own mother (sorry, Mom!). One of the most central elements of the human condition is ambiguity on how to proceed given a circumstance.

“The world is your oyster,” you’re told as a child. “Follow your passion,” the sage wisdom advises. When you graduate college into proper adulthood it’s not as though something changes or clicks overnight. You lack added clarity or insight and are missing the constraints of your parents and professors. You can do anything you want. Want to learn Capoeira? You can. Skittles for dinner? Eat up! Watching Netflix every night? Learning to juggle? Pushing yourself to do better in your career? You name it and you can do it. You own your time, actions, and decisions, and you’re accountable to nobody but yourself. So what should you do?

There’s a key difference in approaching life by working forwards vs. working backwards. Most people work forwards. They look at where they are today, what resources and abilities they have, and figure out how to proceed. This is the sensible approach to life, but it’s a suboptimal one as it doesn’t allow you to see further than one step forward. It is better to work backwards. What does that mean? It starts by asking yourself where you’d like to have achieved in the future, at least 5 years for life decisions, and then reverse engineering the path to get there. Planning further out is a huge competitive advantage. The further out you think, the more possibilities you open up. It allows you to achieve purposeful goals as opposed to doing the next convenient thing. This approach can apply to any type of goal you’re pursuing, whether it be your company’s strategy or your life choices (note: this is how Amazon develops products). So why don’t more people work backwards? First, it’s counterintuitive. Second, it requires long term thinking, something humans struggle at. Third, it requires us to set a far off goal. The combination of these factors leads to compounding difficulty in working backwards. At any given moment, we have an urge to deviate from that long term goal and solve the immediate problem. It’s an adult version of the marshmallow test [1] (which I know had issues, but demonstrated something real). Determining a far off goal is hard because it requires us to ask what we want. It requires one to answer, “What should I do?”

The key issue is that we aren’t taught frameworks to help us navigate the possibilities in front of us. There isn’t a course on how to pick a significant other or how to choose a career path. Without a framework, self-perceived expectations, self-perceived capabilities, and comfort are our core decision makers. We choose what people around us expect of us. We choose to pursue things we think we can be successful at instead of taking on new fields after college. Above all, we choose to dispel discomfort immediately whenever it arises.

People make many life choices on autopilot and without intentionality. Ask yourself: are your career, your past significant other, or your friends intentionally cultivated or are they artifacts of happenstance? These are hard truths to acknowledge. For example, many people I met at Stanford went there because of the perception that it was the best university. They made friends with the people who happened to live in their freshman dorms. They met their significant other through a friend. They were never quite sure about that person, but the discomfort of being alone kept them together. Everyone around them was going into tech, so they studied computer science and went into tech in SF. A simple judgment by US News & World Report dictated their job, their spouse, their friends, and the city they live in. There’s nothing wrong with this, but to me, it’s a harrowing idea. We only get one life and it can pass without us ever asking, "Am I sure the defining parts of my life experience are what I want them to be?"

So why is this? Well, it’s pretty simple: knowing what you want amongst an infinite backdrop of choices is hard. All the truisms on possibility feel trite and inapplicable. Most of us don’t feel a calling. Infinite possibility paralyzes us. We never know where to begin. When was the last time you asked yourself which career out of a list of 1,000 plausible ones you wanted? No longer are we limited by the circumstances of our lives in the way many were throughout history. Moving cities, states, or even countries is now feasible where it previously wasn't. The internet enables learning new subjects and skills, removing more limitations. New locations and new capabilities bring exposure to new people and career opportunities. How can one explore the infinite? Picking from restricted options in front of you is much easier, but it is an unsatisfactory and unambitious way to live your life. So how do you address this? What are some frameworks for navigating infinite possibility in life?

I. Explore before you exploit

One framework Computer Science gives us is the so-called Multi-armed Bandit problem. We continuously decide between exploring new options and exploiting knowledge we have about existing ones (i.e. which restaurant to go to, which career path to try, what movie to watch). Do we pick the known option or do we explore a new one? Most people err towards the certainty of exploiting things they know. They stick with the familiar instead of taking directed risks. My advice: If you don’t know what to do, explore new things. It suggests your current set of options aren’t appealing enough to you. The key to designing these explorations is following the scientific method: formulate a clear, falsifiable hypothesis, take one step in that direction (“run an experiment”), and examine the results. Try something new if you’re not happy with what you've learned. Meg Jay describes this in her book, The Defining Decade, where she suggests people in their 20’s should explore possible career options in a directed way. I believe people should continue this exploration far beyond their 20’s. A good example of this is in career choices, where people often stick with an unsatisfactory career because they are a few years along the path. This is the sunk cost fallacy and overexploitation at play. If you’re going to spend 8+ hours a day working on something, you’d better hope you like it. If the options in front of you aren’t appealing, explore new ones.

One quantitative strategy that is a strong heuristic for the exploration/exploitation tradeoff is optimism in the face of uncertainty [2] - pick the options with the best possible upside. Computer scientists have shown this optimism pays off mathematically. So when considering the 100 new career paths, ask yourself which would be the best if everything goes right. Try that one.

II. Listen to Fear

Another thing I’ve noticed is fear and discomfort are primary motivators for most people. The answer to what we want often lies in this fear. By nature, humans have emotional responses to almost everything. The science of human decision making suggests we formulate opinions and then rationalize them, not the other way around [3]. When we are afraid or uncomfortable, those feelings drive our decision making and we limit ourselves. Cultivating a practice of mindfulness is the best way I’ve found to lean into this fear. Ask questions and force yourself to pay attention to your fear. When you feel fear, force yourself through it. It’s a sign you’re avoiding something because you’re scared of it.

I’ll give an example from my own life here. We debated at Curai whether we should go all in and become a vertically integrated service. The alternative was to focus on selling pure software. Both options had large challenges. I was thrashing between the two options and unhappy with both of them. I procrastinated on complete commitment to a decision for months. This could have been fatal. It wasn’t a conscious thing, but rather a subtle subconscious one. Examining the cause made me realize this was a disguised fear of being wrong. Hard problems never have a perfect solution. The only option was to fight past that discomfort and sit with it. At a certain point, you’re able to work past the fear and make a decision without the paralysis of your discomfort.

III. Maximize for optionality

If you still can’t answer the question of what your long term goals are, the thing to maximize for is optionality. Optionality is the great equalizer. It allows you to capitalize on upside as uncertainty resolves itself. As Nassim Taleb writes, “If you ‘have optionality,’ you don’t have much need for what is commonly called intelligence, knowledge, insight, skills, and these complicated things that take place in our brain cells. For you don’t have to be right that often. All you need is the wisdom to not do unintelligent things to hurt yourself (some acts of omission) and recognize favorable outcomes when they occur. (The key is that your assessment doesn’t need to be made beforehand, only after the outcome.) [4]” When it comes to figuring out what you want in life, this is a particularly powerful paradigm in light of my belief that passions are developed, not discovered. As you experiment and explore, you find that certain things inspire you. Optionality means being well positioned to capitalize as these realizations arise.

So how do you maximize for optionality? Some common strategies include building concrete, employable skills that make you a fit for new opportunities (e.g. programming, writing, learning to learn), learning fundamental subjects that transfer into new domains (e.g., mathematics, physics, probability), building strong relationships with people to open new doors, and avoiding being locked into long commitments to subpar options.

A great example in my life is healthcare. I wasn’t born with a passion for healthcare. As little as four years ago, I had no interest in healthcare and knew nothing about the space. I had never even had health insurance, let alone understood the business of healthcare. I read one book on the subject and I found it interesting (this one, if you’re curious). I read and learned a little more. Healthcare started to fascinate me: the problems were obvious, the solutions were obvious, and yet they didn’t work. I had to capitalize on the opportunity. What did I lean on to get started? My skills in Machine Learning, my obsessive reading habits and ability to learn, and my willingness to look dumb (or if you prefer, a beginner’s mindset). That plus the fact that I had no job and no interest in getting one. I could dive right in. Four years later, people seem to think I know what I’m talking about when it comes to healthcare.

Conclusion

Navigating the possibilities in life is a challenge. Attacking this problem starts with knowing how to think about searching. The best way to build the future you want for yourself is by making clear distinctions about what you want to accomplish and working backwards from there. I hope this piece was a start for you and if you’re interested in digging in more, please subscribe to my newsletter or reach out.