Goals + Reflection

July 23, 2020
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I am curious by the complementing and competing forces of goal-setting and reflection. What is the relationship between the two? And why is self-reflection so difficult?

Setting goals makes me feel in control of a situation. It motivates change and concentrates my focus; it instils discipline and structure in my daily routine. Establishing and working toward a goal provides an immediate sense of direction and purpose. It is a measure of my progression.

As a child, one of my goals was to make a certain hockey team, then to be a top scorer, then become team captain. School was no different; be an honor roll student, then be admitted to a specific university program. Professionally, I regularly set new objectives. First it was to get a job in investment banking, then a job at a hedge fund, to ultimately be a successful investor. I met all of these goals and learned the benefits of hard work, discipline and reaching new heights. My goal-set-achieve model was reinforcing.

Setting and achieving goals has shortcomings. Goals are arbitrary. Achieving goals does not necessarily lead to being fulfilled. Goal-setting encourages a linear trajectory along a specific path; perhaps at the expense of alternative paths.

Losing fifteen pounds, running a marathon, getting a promotion are random. Why fifteen pounds and not twenty-five? Why a marathon and not a half-marathon? Why a promotion and not a different job? Once the arbitrary goal is attained, then what?

The feeling of success from crossing the proverbial finish line is fleeting. As soon as I finished a marathon, got a year-end bonus and summited a mountain, did I actually feel different? I was still the same person. For a moment I was joyful. But the moment passed, normal life resumed and I continued how I had before. The outcome itself did not make me feel fulfilled.

I had one professional ambition after another. Unknowingly, they kept me on, and were dictated by, the same narrow path many others had already followed. I could trace a straight line from where my career started, where it went and how it would continue. My myopic professional intentions deprived me from seeing an alternative path.

Goals enable me to control and focus in a particular situation, but self-reflection allows me to understand it. For me, self-reflection is honestly confronting myself. Why do I feel and act the way I do? It can be a raw, uncomfortable and embarrassing experience. Stopping, thinking, feeling is a necessary balance to doing. How does setting and achieving a goal make me feel? What have I learned from the experience? How should I change?

Although achieving a goal may not make me feel fulfilled, attempting it and reflecting on the experience can. In 2,325 kilometers, 1 goaI: failure or success? I discussed my attempt at running a marathon in under 3 hours. I posited that the feeling of success in achieving a goal is fleeting, but the sense of accomplishment in the journey to achieving it is long-lasting. Accomplishing the actual goal may not make me feel different than failing at it. If I am committed, disciplined and honest with myself, I will achieve the lasting feeling of accomplishment regardless of the end result. The purpose of setting the target is not to simply attain it. The real purpose is to experience the sense of accomplishment from attempting it; that is what makes me feel happy and fulfilled. The goal is simply the conduit.

Goals by themselves lead to a linear trajectory on a narrow path, but paired with self-reflection, together they can foster a step-function change on a new path. My life followed a linear trajectory during my decade on Wall Street. From early adulthood until my thirties, I did not reflect. I did not take the time to stop and think about what I really wanted. I did not pause to consider how what I was doing was actually making me feel. As a result, I only thought about the one path I was arbitrarily on. After a decade in that mindset, I finally started to reflect. It was brought upon by feeling like my life had plateaued. I thought “is this really it?” I became aware that I had been accomplishing my professional goals for the praise I would receive. It made me  feel smart and successful. After a while, that novelty wore off. I did not find meaning in achieving my professional goals yet they consumed my life. I was left feeling unfulfilled and discontented. It was a gradual shift in mindset, brought upon by honest self-examination, that made me realize something needed to change. My change has been an on-going progression. In Lessons for life - from a year of discovery I wrote about what I have learned. Self-reflection enabled me to discover a different path and fundamentally changed my life. Had I continued to set goals without reflecting, I would not have experienced the excitement, fulfillment and growth that I discovered as a result of a step-function change in my trajectory.  


Self-reflecting is difficult. It is heavy, uncomfortable and painful. It took courage for me to admit that I am fallible, that I made mistakes and have insecurities. Reflection requires investing time today to potentially reap the intangible benefits long into the future. Instead of reflecting, it was easier for me to occupy myself with a distraction that brought me instant gratification. But fulfillment is not a feeling that is immediately gratified. It accumulates over long periods of time. To achieve longer-term fulfillment, I need to reflect today.

I had preconditioned myself to goal set, achieve; repeat. I celebrated my achievements and then it was immediately on to the next one. “So what’s next?” I would hear. I am used to moving forward decisively. I was not taught to self-reflect. It is not an academic discipline. I am learning for myself how to do it.

Last year, I folded my startup. After several months of working on the idea, I lost my interest in it. My start-up was solving a problem that I did not care enough about. It was difficult to pull the plug for conflicting reasons: I realized that my startup would not make me happier in the long run, but continuing my startup gave me direction and purpose. Jettisoning it would be embarrassing. I had already broadcast it to everyone. If I was not pursuing my startup, what would I do? I feared having to start over and explain myself. Continuing to pursue my startup gave me immediate gratification. Ultimately I decided to pull the plug, but continuing would have been easier in the near term. Reflecting on my startup might have saved me months or years of pursuing something that I should not. It  also exposed my desire for direction and immediate gratification.  


Like goals, reflection also has its shortcomings. Too much reflection and nothing gets accomplished. Dissecting my thoughts and feelings can be paralyzing. I have succumbed to analysis paralysis. My overanalysis and overthinking of a situation has impeded progress and second guessed decisions. A course of action or decision is often better than none. Inaction breeds complacency and hampers growth.

What is the right balance of goal setting and reflection? I do not know. Too much goal setting and I succeed but do not feel fulfilled. Too much reflection and I feel complacent.

Goal setting and reflection are equally important and dependent on one another. I need a goal to then have an experience to reflect on. But I need to reflect to ensure I set the right goal. What comes first? Who knows. It does not matter. Just start.

I view goal setting and reflection as a circular feedback loop. I can start at any point. For example, I set a goal. I work towards it, measure my progress, sharpen my discipline and compare the outcome to the objective; that is the physical experience. I also live the reflective experience in tandem. I check in with myself every few days or weeks to assess how the physical experience makes me feel. I ponder “What have I learned? Why should I continue to work toward the goal?” on long runs. I discuss how I am feeling with those close to me. This writing is also a form of my self-reflection. I then course correct. I may drop the goal entirely, set a new one or stay the course. Reminders to reflect more regularly ensure that my goals are congruent with my feelings. As simple as it sounds, it makes a big difference in my daily happiness and fulfillment.

The physical and reflective experience combined create wisdom. With wisdom, I better understand what makes me happy and fulfilled. It is difficult, daunting, and possibly unrealistic, to set goals about what I want my life to look like in forty years. It is a bridge too far. It is possible, however, to continually set immediate goals, reflect and course correct today. Overtime, all those small goals, reflections and corrections will lead to a happy and fulfilling life.

How do you balance goal-setting and reflection? Has reflection been difficult for you? Let me know your thoughts.

Samuel Andrew

Sam is an adventurer, learner, lover and challenger. He questions why things are the way they are, especially in his own life. He uses his own experiences as a lens into personal growth. He shares these raw and honest experiences in order to be of service to others.

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