3 Months, 1 Habit, Stronger Self-Esteem
How Tracking Wins Is Transforming My Confidence
I spent much of the past nine years sabotaging my goals and disliking myself. I didn’t consistently exercise or eat healthily, I often spent hours scrolling TikTok instead of going to bed on time, and I took few steps to start my dream business. I subconsciously believed I would fail at these goals before I even started—and these are just a few examples.
I called myself nasty things: “useless,” “worthless,” “stupid,” and “failure,” among others. I berated myself over the smallest mistakes. I felt tremendous anxiety with respect to taking on new challenges. And I spent much of my life people-pleasing instead of being myself.
Shockingly (at least to me), over the past three months, I have improved or resolved most of these problems. I did so by discovering their root—low self-esteem—along with a helpful way to meaningfully improve it: writing down things I’m proud of. Because “self-esteem” and “pride” are both used vaguely today, I’d like to briefly explain what I mean by them.
By self-esteem, I mean the evidence-based belief that you are or are becoming a competent person (you can use your mind effectively to solve problems and achieve your goals) and are morally worthy of happiness (that happiness feels right and is yours to achieve).
By “pride” or “being proud of myself,” I mean taking joy in my accomplishments and the person I’m becoming as a result. I don’t mean “arrogance,” “narcissism,” or “self-obsession.”
I know three months isn’t long, so it’s hard to say whether these changes will last; subconscious behaviors and beliefs are tricky to fix. But I have used this habit of writing down my accomplishments inconsistently before; I noticed that my self-esteem increased, and I experienced some of the same improvements, such as improved self-talk.
The strategy works like this: I do something worthy of being proud of, which raises my self-esteem and makes me feel good. Then, I write it down. Writing it down puts the accomplishment in real, permanent, physical form. This solidifies my knowledge of what I’m proud of (as opposed to a vibe or inkling), reinforcing my self-esteem while also making me feel good in the moment. This positive feeling emotionally incentivizes me to seek out and do more things that make me proud of myself. This creates a virtuous cycle: I want to do things I’m proud of in order to feel good, and I pay more attention to opportunities to improve myself.
Here’s one problem this habit has helped me solve: I have struggled throughout my life to be assertive in healthy and respectful ways, so I’ve recently started intentionally pushing myself to do so. The other day, I was speaking with a friend about foreign policy. I generally don’t discuss politics because I hate how aggressive such conversations can get. However, I wanted to talk to this friend because I thought that there was a good chance that we could have a thoughtful and enjoyable conversation on the subject. I was explicit and assertive about my views in a respectful, truth-oriented, non-aggressive way. The conversation was great—we disagreed on some points, but we both enjoyed talking. This was uncomfortable, but because I pushed myself to grow, my self-esteem increased, and I felt good. I wrote down what I did—I made a permanent record of it—and I felt even better.
Afterward, I started looking for further opportunities to be assertive, and I found another one a few days later. I was having a conversation with another friend during my lunch break about an article she read. It was a fascinating discussion, but we were going long, and I needed to get back to work. I told her that I had to pause the conversation but would love to continue it later. Stating this boundary was uncomfortable, but I am proud of doing it despite my discomfort. I wrote down what I did, and the cycle continued.
I’m including more examples of how I use this habit at the end of this article in order to demonstrate how you might use and benefit from this practice. If you’d like to see those, scroll to the bottom of this essay.
My record of all the things I’ve written serves as a bank of evidence that proves that I am becoming a better, more capable person. Seeing and reflecting upon the entire list feels satisfying, bolsters my self-esteem, and is an excellent reminder of how much I’ve grown. (I reflect on my past week’s journal entries every Sunday. I recommend it—it’s a great way to start your week.)
One question I often ask myself is: How can I make it as easy as possible to write down the things I’m proud of? I have a widget on my phone that takes me to a document wherein I list all the things I’m proud of, and I almost always have it open on my phone in the background.
As with any new habit, it’s absolutely OK (usually ideal) to start small. We have to begin where we are, not where we wish to be. Full, complete, consistent self-esteem takes years to build. But small, incremental improvements are still meaningful, and you can feel them. They make a difference. Even simple acts such as mustering the courage to tell someone that you found a joke distasteful, spending a little extra effort on a side hustle, or taking a small step toward having an uncomfortable conversation are worthy of pride and of writing in your journal. Small wins are still wins. Small improvements to self-esteem are still improvements. And, I think you’ll find that such “small” wins quickly snowball into bigger wins, improved self-esteem, and greater happiness.
Usually, what I’m proud of falls into one or more of the following categories. Your categories may be different from mine; I’m sharing these and providing a few examples to show how you might benefit from this habit:
Self-regulation and fortitude: Did I overcome an irrational impulse or an unhelpful feeling of resistance or reluctance? For example, I had an impulse the other day to check my notifications in the middle of a work session. I paused, thought about whether that was the best decision, let the impulse pass, and continued my work. I am proud of this.
Courage and assertiveness: Did I overcome an irrational fear? Did I speak my mind when it was appropriate and necessary to do so, even though I was afraid? For example, the other day, a friend responded to me in an unduly harsh tone. I told her that I didn’t appreciate it and that I would like her to respond in a kinder way moving forward; she agreed and apologized. I was assertive—I stated a healthy and reasonable boundary. I am proud of this.
Integrity and moral repair: Was I honest? Did what I said match what I did? If I hurt someone or failed morally, did I attempt to correct the failure and prevent it from happening again? For example, I recently had an argument with a friend during which I realized I was primarily in the wrong. I apologized, introspected about what went wrong, and made a few changes to prevent this problem from happening again. I am proud of this.
Systems and leverage: Did I improve a system, process, or checklist in order to save time and effort in the future? For example, I recently added a checklist item to review my work priorities each weekday. This helps ensure that I’m working on the most important project and using my time in the most effective way possible. I am proud of this.
Self-understanding: Did I discover previously unknown reasons behind an emotion? Did I learn more about my own psychology? Did I discover a limiting or irrational belief? For example, I recently discovered that one of the roots of my anger is that I don’t consistently communicate my needs and boundaries. I have started taking steps to communicate more clearly and often, and I am proud of this.
Connection and contribution: Did I express gratitude when it was appropriate? Did I help those I care about? Did I express to those I love that I love them? For example, I recently had a conversation with my best friend, and I asked better questions and was more engaged than I had been in months. I am proud of this.