How To Be Ambitious and Not Miserable

If you’ve ever had the thought, “I could do more. I should do more. Why am I not doing more?” And then the subsequent thought “wow, I’m making myself feel miserable right now,” this essay is for you. There are many ways as an ambitious person you can drive yourself mad.

It might be helpful to define ambition, which for the sake of this essay, I define as the lofty drive to improve yourself or the world around you. Improvement is hard and painful. So, if you’re wired with an ambition-oriented outlook, it’s not always the smoothest ride. 

I’ve collected a short list of ways I’ve found, in the mid- to long-term, to move myself out of that depressive feeling caused by a ceaseless want to do “better.” These aren’t quick wins. These won’t zap you out of a depressed state instantly. But, if you can hold any of the below as truths in your head, they can act as helpful touchstones to beat back the self-judgment that often comes with latent ambition and transmute your ambition from a greedy antagonist into an exciting partner in life. 

1/ Judge your work on your current ability, not your perceived capacity 

Dreaming is great. And thinking of yourself as capable of achieving your dreams is even better. But there’s a delta between your perceived capacity and actual ability right now. For instance, you might think you have the capacity to write the next great American novel. And maybe you do. If that’s your bar for success, amazing! You have big dreams and belief in yourself. However, if you struggle on certain days to make progress on that novel and judge yourself in those moments for not “reaching your full potential” because of it, you’re being too hard on yourself. Why? Because until you write the next great American novel, you don’t have the ability to do it. Capacity is not a fair measuring stick to judge your today self with. If you judge your work or hobbies or impact on what you might eventually be able to achieve, you will always feel like you’re underperforming, because if you’re a dreamer and a thinker, you will always feel like there is a next level you can unlock. And there probably is. But you’re not there yet! So, judge yourself on what you’re able to execute on right now. Maybe your ability today is writing a nice short story, or a pithy essay, which are great milestones as you work your way to writing a novel. Move your measuring stick to these closer time horizons and attainable milestones. You’ll be able to better achieve them, and it’ll create a reinforcing flywheel of success that will propel you to achieve your more ambitious dreams. 

2/ Think less; do more

Our minds are wonderful self-torture devices. Ambitious minds even more so. This torture typically manifests in what psychologists label “intrusive thoughts” (e.g., unwelcome thoughts that create more misery than joy). You might feel you can think your way to joy and happiness. And that is simply not true. No amount of thinking will make you happy. In fact, it’ll increase the chasm between you and the feeling of joy. What brings joy? Action. Doing something. Anything. You don’t even have to do it well. Just do it (thanks, Nike). It doesn’t need to be good. It doesn’t need to be big. It just needs to be something. If you’ve been meaning to exercise more, go and do a 15-minute walk around your block. If you’ve been meaning to plan a vacation, hop on Google and enter a few, random destinations. Getting started is the hardest part. Doing something will silence the ambitious critic in your head and it will provide some forward momentum to something even bigger and better. If you keep doing stuff and kicking up dust, you’re increasing the chances of doing or finding something that resonates with you, and at that point, you’re well on your way to doing something incredible. 

3/ Invest in relaxing activities that are not mentally or physically harmful 

For me, after a long day of stressful work, a beer or glass of wine or [insert favorite inebriate here] always sounds like a nice way to take the edge off. But I’ve found that more and more, this shortcut, with the equation: stress + inebriant = less stress, is actually: stress + inebriant = less short term stress + more long term stress. As an example, if I have a couple beers on a weekday after a particularly trying day at work, the next day, I wake up feeling a bit more groggy, a bit more irritated and a bit more pissed off at the world. So, to counteract those blues, I consume more than a healthy amount of caffeine, which in turn gives me anxiety, which then requires me to come back down at night with another inebriant. And the cycle continues. Nowhere in this flywheel have I addressed the root issue at hand. I’ve actually even further exacerbated the issue as well by creating a less restful version of myself day after day. I’m not trying to demonize booze or caffeine here. Maybe these things don’t hit you as hard as they hit me. But finding a relaxing activity that doesn’t negatively impact your mental or physical health is a much better alternative. For me, as of late, I’ve turned to having a cup of tea, a piece of chocolate and listening to a comedy podcast while I wind down for the night. I can’t make this happen every night, sometimes I really need an IPA, but the nights that I do, I know I’m moving a little closer towards my goals without actually working on them. 

4/ Draw motivation from your impact to others, not the impact to you

If you have a lofty, ambitious goal, thinking of what it will mean for you if you achieve it is not always a powerful incentive. You can look around at your current life, and think, “this isn’t too bad, why am I pushing myself so hard for more?” That is a very reasonable, rational and healthy way of thinking. In doing so, this point of view can temper unfettered ambition. In keeping you emotionally safe, it can also have the adverse effect of blocking you from realizing some of your ambition. To counteract this, I’ve found it useful to think about how my ambition, if realized, will impact a greater set of people, other than myself. For instance, the thought: “I’ll never become an entrepreneur if I don’t work on my project tonight,” is a lot less motivating than “I’m really excited about providing this service to those that need it.” This shift in mentality is akin to, “giving your gift to the world,” which I think is a beautiful and admirable quest. You can also hold this truth in tandem with your previous, rational thought of “my life isn’t too bad, I don’t need to push myself for more.” You don’t. Your ambition is only providing you the opportunity to push yourself to help more people, and if you want to do that, fantastic, and if you don’t, equally fantastic, taking care of yourself is a net positive for this world too. 

5/ Get excited about actions, not achievements

I’ve often found myself daydreaming about the outcomes of my work. One of my good friends calls this “future tripping.” Future tripping is fantasizing about what the future would feel like and what it would bring you when you realize your ideal outcome. This is unhelpful in a few ways: 1) you will never realize your ideal outcome, so you are destined to not meet this bar and disappoint yourself 2) dreaming about the future is a serotonin hit that gives you the release of achieving success without actually achieving it, demotivating you from doing the work and 3) it focuses on the outcomes, not the inputs, which is a recipe for not enjoying not enjoying the present, which is always about doing the work and never about receiving the accolades. 

6/ Join in communities that are in tune with your goals and personality

Working alone is hard. The more we advance in society, the seemingly more we isolate ourselves and detach from a center of community. It’s proven that decade after decade, we have less friends than the generation before us. This could be a negative consequence of economic prosperity (I don’t need to be supported by my family or community because I can take care of all my basic needs) or technological supremacy (I don’t need to rely on my neighbor for sugar, I can one-day Amazon order it to my front door). Or maybe it’s something else. This essay won’t try to answer this question. But, given this trend, finding a community that resonates with you and inspires you and pushes you is more important than ever. It can be the difference between realizing your life’s work and never making progress on your dreams. These communities can be in-person or online. I don’t think it matters. As long as you have a tribe that fuels your fire, offers encouragement and inspiration, among many other things. On the flip side, I’ve found it less helpful to try to join as many communities as possible (more of this below on focusing on less things). Not that you should double down on a single echochamber, diversity of thought is always great; however, a community acts as creative catalyst, and if you’re part of many divergent groups, it can send you down many divergent, creative paths, which can lead to less focus, which can lead to you not grinding long enough on that one, special gift you have to give to the world. 

7/ Focus on a small set of things

I have a long list of things I want to do and try to accomplish. My default mode is to jump from whim to whim, enjoying the excitement of trying something for the first time and dreaming up a big idea. My friends and family must surely roll their eyes when I share yet another thing that I’m going to get into and make my life’s work (these fleeting obsessions of mine typically last no more than three months). This approach is a great tactic for understanding what you like and don’t like, but at a certain point, I discovered it was in my best interest to pick one thing. I was scared to pick one thing. What if I was wrong? What about all the things I was leaving on the table? What about all the different ways my life could go that it now certainly would not? These are all very real questions that rattle through my head when I make the conscious decision, day after day, to focus on one thing (which is writing). But making tradeoffs is a blessing, it supports the conviction of your focus. Giving yourself constraints is helpful, it reduces the cognitive load of making decisions: you can easily review an opportunity and make a yes/no call based on whether it brings you closer to your focused goal or not. So, pick one thing. Give yourself six months to do that one thing. You’ll be surprised where you end up after that time.  

And that’s what I’ve got for now. This list is not exhaustive. I might come back to it and add more later. Focusing on one of these and holding it as a personal truth, where it becomes my default reflex, has been tremendously helpful, dare I say life changing, in taking the ambitious critic in my head and turning it into a true friend and partner, one that inspires me, motivates me, and very rarely tortures me for not always working steadily towards its ambitions. Your ambition is not you, it’s a part of you, and an ally is always better than an antagonist.