Ambition vs. Enjoyment: A False Dichotomy?
Success in any pursuit seems to be about finding the right balance between competing dichotomies. Chaos and order; leading and following; planning and improvising; intensity and recovery, just to name a few.
The dichotomy that I find the most challenging in my own life is the balance between ambition and enjoyment — the urge to learn, improve, and strive to be my best and create a better future, with the desire to enjoy the present moment, and be satisfied with what I have already achieved.
The funny thing is that even though it feels like these two ideals are at odds with one another, I know it is a false dichotomy. It is eminently possible to enjoy the process of working towards a big and meaningful goal that will positively affect the future. In fact, I believe that alone is the real key to happiness.
But that doesn’t mean it feels like they are aligned. In my experience, the default is for ambition and enjoyment to feel like opposing forces because the only times I stop and reflect are when things are difficult or not working at all.
In the words of Victor Frankl from Man’s Search for Meaning, “Those who have a why to live, can bear with almost any how.” To me, this means the problems we choose to solve are the most important decisions we can make. Every path is guaranteed to involve adversity, but if it leads towards a better future and helps me grow along the way, then it can be extremely rewarding and enjoyable. I just need to be able to find a way to appreciate the process, and give meaning to my struggle when things inevitably get tough.
But knowing this intellectually doesn’t make it any easier for me to remember and embody day to day, and moment to moment. It is something I must consciously remind myself of, not something that I feel intuitively.
What follows are some of the ways I think about how to align my ambition and enjoyment, with one major caveat — it is a constant struggle. There are countless days where I wonder what I’m doing and where I’m going, but taking time to define, reflect, and realign my path is the only way out.
1. Define success for myself, and constantly revisit it.
How I define success is something I’ve thought a lot about, and has informed most of my major life decisions over the past decade. It’s what led me to get married, leave my job in investment banking, take a 1-year sabbatical, start my own company, and eventually leave that company in order to seek out my next chapter of growth.
First, it involves defining a vision of what my ideal life might look and feel like. Where do I want to be, how do I want to spend my time, and with whom? Most importantly, what types of problems do I want to spend my time solving? I think happiness and success are about solving better and better problems over time, so imagining a future where I have no problems is unrealistic, and frankly, undesirable.
I often fall into the trap of imagining a future where I have no stress — or more specifically, the stresses I’m currently experiencing are non-existent. It’s far more productive to imagine which stresses I do want in my life (i.e. which problems I want to solve), because it is primarily through problem solving that I derive meaning. Pick ambitious and important problems, and I will have a meaningful life. Pick trivial problems, or no problems at all, and I will spend most of my time wading through the problems others thrust upon me instead.
For me, this process is mostly about consistently revisiting my goals and dreams, and recalibrating them over time. I like the analogy of sailing to an island — you can aim yourself towards a faraway paradise, but you have to constantly tack back and forth as the winds and seas push you off course, and you discover new obstacles and treasures on the horizon.
2. Think long term, and get to know yourself better along the way.
When I think of “the future”, I tend to think of a time horizon that I can actively imagine — perhaps 12 to 36 months from now — and it tends to resemble the present in many fundamental ways. I can try to imagine what the physical world will look like (who, what, where), but it seems impossible to imagine how my own mindset will change over that time. Since perception is reality, this seems like a major flaw in my forecasting abilities.
One of the keys to thinking on a longer time scale lies simply in getting to know yourself better, because the better you know yourself, the more accurately you’ll be able to forecast your future behavior. For me, the only useful strategy has been to keep a regular (morning) journal. It is only through free hand writing that I’m able to express what I’m thinking in real time, and learn from it. Over time, patterns emerge and I’m able to recognize the important signals amidst all the noise bouncing around inside my head.
In the world of investing, the ideal time horizon is generally believed to be around 7–10 years, so it seems logical to think of our own life goals on a similar scale. Although this can be extremely difficult, it provides an incredible opportunity for differentiation. If you’re able to think this way when others aren’t, it will give you a major advantage in realizing your goals and dreams.
3. Design a process that I enjoy, primarily though my daily habits.
If I’m able to define success on a long enough time scale and frequently recalibrate my trajectory, then the bulk of my happiness would seem to lie in the day-to-day routines that comprise my life. Just as my long-term health is based on a series of day-to-day decisions (nutrition, activity, sleep), so too is my progress towards any goal. Or in the words of F.M. Alexander, “people do not decide their futures, they decide their habits and their habits decide their futures.”
Over the past year and a half I’ve put a lot more focus on my daily habits and routines, and I can tell you that the things that once sparked annoyance at best (e.g. flossing my teeth before bed, stretching and journaling in the morning) are now things I have come to crave. In fact, the negative feeling associated with missing them is now far greater than the minor annoyance I used to associate with initiating them.
With all that said, there are some situations where even the best habits or practices will never yield joy — being in a toxic relationship or working somewhere that is not aligned with your values, for example. Chances are that if you can’t find any reliable ways to enjoy the process, you’re probably working towards the wrong goal. Every new habit takes time to get over the hump, but if it’s been years without joy or positive results, then it’s probably a good idea to re-evaluate your goals and go back to #1.
4. Be patient with results, and make time to reflect and celebrate progress.
Results take time, because all the benefits of compounding come at the end. But when you’ve put in the work, recognizing how far you’ve come can be richly rewarding, regardless of the final outcome. It is amazing to take notice when your new baseline is comprised of things that were once goals and dreams. But being present to this requires conscious reflection.
For me, this was most evident with my startup. Challenges that felt existential when we were starting the company (e.g. product-market fit) were not even on my mind a few years later. That is why it is so important to consistently reflect on my progress no matter how small the achievements, because even though there is always so much further to go, there is also much to appreciate about how far have I’ve already come.
One thing I’ve found helpful in this regard is to plan celebratory events in advance, such as a special dinner or weekend away with my wife, or a party or fun excursion with friends. Planning it in advance it gives me something to look forward to, and consciously selecting what to celebrate helps me actually stop and think about how far I’ve come. Planning in advance also means you’re more likely to get that rare and special reservation, and have more people to share it with.
I can’t emphasize enough how balancing these important forces is a constant struggle, because there are countless days when my drive to achieve feels utterly at odds with my desire to enjoy my life. But the more I think about it, the more I know that the only way to truly be my best is to be fully absorbed in what I’m doing, and have fun while doing it. And the only way to do that is to stretch myself in the pursuit of a big challenge that I deeply care about.
As they say in surfing, the best surfer in the water is the one having the most fun. Although it sounds trite, it’s almost always true. The key just seems to be picking the right break to surf.
This post was originally shared in Issue #26 of my biweekly newsletter, In The Know. Please check it out and subscribe if you’d like to have these posts delivered directly to your inbox, as well as other thoughts on how to live a healthier and more examined life.
