9 min read

Where do you see yourself five years from now?

Although the title might suggest that there would be helpful advice for an interview, there won’t be any. Not specifically. Maybe as a side-effect. What follows is my exploration of what it means to ask that to yourself and what to make of it.

Where do you see yourself five years from now?

In the context of an interview, it has been used for so long and often that it passes as a cliche. It's seen as something that you bullshit your way around to get through the interview, rather than something that demands serious thought. Since interviews are designed to measure and reward good performance rather than sincerity and honesty, there's a natural inclination to say what the other person wants to hear. But when you ask yourself that, there are truly no wrong answers, and no time limits, which is important, because making a genuine attempt to answer that, it turns out, is much harder than it feels at first. Doing that means sliding deep into the seemingly bottomless pit of self-discovery.

What does it mean?

Understanding what it means is best done by picking apart distinct pieces of it and seeing what they mean, or don't mean. It is not as specific a question as it sounds, and the answer too, doesn’t have to be as specific as one might think.

"Five years"

There's nothing special about five years. It could very well have been six, or seven, years. That specificity is the least important part of it and isn't meant to be taken literally. Focusing on the wrong detail could derail your thinking. It's merely used as a proxy.

Proxy to what, exactly? To a time that's far enough in the future for a person to make a meaningful, deliberate change in their life, to achieve considerable growth, or expertise, in a field. It means having thought about goals that are bigger than the ones that can be accomplished in a matter of weeks or months. It indicates a period through which chasing a goal requires commitment, drive, discipline and grit.

"Where do you see yourself.."

We're visual beings. We see things in our minds as if they were real. While sitting in a classroom listening to a boring lecture, we see ourselves playing out in a field. While hunched on our office chair slogging our ass off in front of a computer on a sunny day, we picture ourselves sitting by the beach, reading a book and sipping cold coffee. We see things in our dreams and work hard to make them come true. Visualization has the potential to not only bring you immediate joy, but to move you in certain directions that yield benefits in the long-term. So that part of the question might prompt you into thinking about a certain place, a role or a position, that you’ll be in, in the future. But such clarity has often eluded me and I doubt if it’s even useful. Following my interests and curiosity have led me to paths that I never knew existed, and took me to places that have turned out to be better than my imagination.

I could not tell that I’d see myself as an ultra-runner one day, when I started to jog around the block of my house, trying to shed some pounds I had gained by being complacent and comfortable. I could not tell that I could run hours without fuel and stops, when I was running out of breath running between a few signals on the streets. I could only hope to see myself being healthier and fitter than I was at the time. Other good things just happened along the way.

I could not tell I would manage a team of people one day, when I started aggressively learning and doing the things that I found interesting at work. I could not tell that following my interests and playing to my natural strengths would help people and the business as much as it did. I could only tell that what I was doing at the time seemed boring and dull, and that there were other, non-technical, aspects of the job that were interesting and those that not many people were focusing on.

I could not imagine writing essays in my journal everyday, about things that are hovering in my mind, when I started writing as a way to vent and calm myself down.

So the pattern underlying some of the major transformations I’ve gone through is this – they’ve started in times of war, within myself, and have not only got me out of it, but all the learning and growth in the war time have translated well into habits and hobbies that still serve well during peace. Just like all the innovations during the World War were channeled into shaping a consumerist society, the tools of the trade I learned in times of discomfort have morphed into something that still makes them useful.

I could not tell where I saw myself years down the line. I have found it more useful to think about what I want to strive towards – the skills I want to learn, the growth I want to achieve, the impact I want to make,  the relationships I want to grow, the problems I want to solve, the obstacles I want to overcome, and the responsibilities I want to take on. As you can see, none of those happens in a short span of time. They take years of sustained effort.

Figuring out what you want seems like an easy thing to do, but upon reflection, you'll quickly realize the overwhelming nature of the possibilities. The challenge is not as much the dearth of choices as it's the abundance of it. There's often so much we want to do that narrowing down our options and making a decision feels paralyzing. Another thing that makes the exercise challenging is that we don't often realize how little we know ourselves. To know ourselves well is to know about our interests, preferences, beliefs, emotions, personality, values, constraints,  strengths and weaknesses, all of which we hardly pay attention to, in this age of constant and never-ending distractions.

The counterintuitive approach

While knowing what you want seems daunting, there's an easier place to start, a slightly different question that’s often relatively easier to answer – “What do you see yourself not doing five years from now?

The two ways of posing the question are similar to the idea of positive and negative freedom, or as they are often described, the “freedom to” and the “freedom from”, respectively. Rephrasing the question like that is helpful, because we are better at pointing to what we don't want. Recognizing problems comes more naturally to us. Solving them takes more effort, relatively speaking.

I knew that I had to shed pounds, that I had to get mentally and physically fitter, that I didn’t like the lethargy, the lack of confidence and the lack of direction I was feeling at the time, which led me to hiking and running, as a starting point.

I knew that I didn’t want to suffer in silence with no avenue to express my feelings when I was angry, disappointed, or dejected, which led me to start putting down my thoughts on paper, as a starting point.

I knew that the majority of the engineers around me were missing some of the crucial parts of the job, the non-technical aspects of it, which led me to start filling the gap, as a starting point.

Once you recognize, and acknowledge a problem, finding solutions starts with an idea of the desired outcome. The obvious desired outcome, in the face of a problem, is to make it go away. That’s good, that's progress. It's just like it is with physical exercise. Losing weight or finishing a race is seldom the challenge, making up your mind to sign up for a race and showing up at the starting line are. Once a problem and the desired outcome has been laid out, you’ll start to see paths that take you from one to the other. Solving problems one at a time opens up new possibilities. It helps you find out what you’d do when you have none of the problems that you have today. Only when you have the "freedom from" external obstacles can you hope to have the "freedom to" pursue your interests and passion.

Classes of problems

Since growth happens in the face of a challenge, it'd be naive to want to lead a life with none. That'd be dull. You'll always have some. But that doesn't mean all obstacles are good. I like to think of an idea that I call "class of problems". There are those that you'd love to solve and those that you'd rather not have; some that make you feel challenged and give you the opportunity to realize your potential and others that hold you back.

Think of problems as geographical locations in the real world. There are some that you'd love to visit, and some that you'd rather not, for whatever reason. You also don't want to be visiting the same place on every vacation. Since the fun is in the novelty and not inherently in the act of living in any place, it's not fun to be stuck in the same holiday destination.

Identifying the classes of problems

To identify the classes of problems in your life, think about the problems you deal with on an everyday basis – could be in your relationships, at work or outside of it, could be technical in nature, or something related to your personal growth. Think of the areas you'd like to improve in.

Group them into classes, like "problems with setting boundaries", "communication problems", "health or fitness issues", and so on. Try to identify which ones hurt you the most, or which ones could bring the most value to your life.

One example that I can think of from my journey of personal growth is from five years ago. In my first job after graduate school, I felt a sense of void. After all the hard work to get to where I was at the time, life felt too easy. The work was not as challenging, yet the money was good. I spent most of my days eating delicious food, traveling, hanging out with friends, sleeping, and watching movies. I had no idea that material comfort could bring so much psychological discomfort. In search of answers, I started reading books.. self-help books, and I also decided to get some physical exercise. While books helped nourish the brain, physical exercise, hiking and running, helped shed some pounds. At the time, had I asked myself where I saw myself five years in the future, I would not have come remotely close to where I'm today. I had no idea what was in store, but I had a feeling that things had to improve, which led to a transformational and  a fulfilling journey. All I could say back then was that I wanted more challenges to tackle, both physically and mentally, that I wanted to get out of the mindset of complacency.

Another example from my career is from three years ago. After having built user interfaces on the web for a long time in my career, I realized that I needed a change. That simple desire for change made me think about what it was about that that I wanted to get away from. After pondering about it for a few weeks, I realized that it was the nature of the work. In the rapidly evolving landscape of frontend engineering, I found that most of my time was spent debating about the shiny new tools, frameworks and libraries that we should be using, rather than talking about ways of solving the real-world problems. Having started building user interfaces in the days of Internet Explorer 6, and vanilla JavaScript, I was amazed by the power of the trio of web platforms – HTML, CSS and JavaScript. I wasn't happy with the kind of overengineering that started to happen with the rise of frameworks like React, Redux and GraphQL. The tools themselves were good for certain kinds of problems, especially complex ones, but I thought that they started to be used and justified for every problem, even the ones that could have been solved by common sense and better design. I had always enjoyed using technology as a means to solve problems, rather than as an end in itself. So building fat web applications, when simple web pages would have sufficed, seemed like something that I didn't want to be a part of. That was a class of problems I did not want to deal with. I needed some stability in the ecosystem so I could focus on problem-solving. Backend engineering seemed like a good fit. The lack of infinite choices made it simpler to stick to a set of commonly used tools and frameworks and move on to solving other problems. In a lot of ways, the world of frontend engineering felt like a teenage kid, who cherished autonomy, flexibility and change, whereas the landscape of backend engineering seemed like a middle-aged adult, who preferred a sense of calm, stability and predictability.

The first time I had to explain my desire to change teams to my boss was when I first thought about the idea of a "class of problems". It's not that I thought building backend systems was harder or inherently better than developing user interfaces. It's just that I wanted to be solving a different class of problems.

Back to the original question, of knowing where you see yourself in the future. Five years is a long time, long enough to create a drastic change in the trajectory of life. And as much as not knowing is looked down upon, that's part of the fun. Just like a painting starts with broad strokes on the canvas, the point of the answer is not in the specifics, but in having a general idea about the direction, an awareness of the values and principles that guide you, of the things that interest you and those that hurt you, and of the things that you find are worth your time.

Where do I see myself five years from now?

I think I'm getting close to an answer, getting close to painting the broad strokes. I don't feel ready to share it publicly just yet, but if reading this has piqued your interest and you want to talk about either your "classes of problems'' with me, or want to know more about mine, I'd love to hear from you!