Building habits (a case study with exercise)

After many failed attempts, I’ve built and maintained a workout routine for the first time in years.

Reflecting upon my past failures, I’ve asked myself countless times, why was it different this time? Why am I so confident that this habit will be sustainable, and is there anything I can learn from this experience to help me build other habits? I decided to use this experience as a case study to understand how habit-building works.

Identify a clear emotion-driven motivator.

It wasn’t enough to say I wanted to exercise to look or feel better. I realized there needs to be a strong emotional trigger that gives you enough activation energy, the energy required to get started. More often than not, the activation energy comes from discontentment (e.g., fear, anger, a longing for something). However, it can also be a positively rooted emotion (e.g., curiosity, excitement, love for something).

As much as I hate admitting it, the trigger for me was the feeling of disgust. I attended a family gathering when I saw a photo of myself that was not so flattering, and it created such an organic, repulsive, and disgusted feeling with myself. How did I get to this point? I’m supposed to be in the prime of my life, and instead, this is where I am? This created such a strong emotional response that it made me realize that I needed to change, and it gave me the activation energy that I needed to get started because I never wanted to feel how I felt at that moment again.

Make a plan (Research & Reflect).

A strong emotional response will give you the kick you need to get started, but if you jump right into it without doing the appropriate research and reflection, your “habit” will only last a few days. I had to be really clear about why I wanted to do this. Some questions that I asked myself were:

  • Why do you want to build this habit? (Covered above✅)
  • You’ve failed so many times in the past; what will you try differently this time? I’ve failed many times because I hate going to the gym. I hate the treadmill, and I feel like I always get hurt when I lift weights. The only vigorous exercise in my life that I’ve ever enjoyed is playing basketball. If this is to be sustainable, I need to do something I want, so I will try to play basketball.
  • What do you need to get started? Where will you go? How often? How will you fit this in with your work schedule? All I need is a basketball and a pump for the basketball. I used to go to a park years ago, so I can see if the hoops there are still in decent condition. I don’t want to go in the morning, but I can go in the evenings after work before dinner.
  • How will this impact other parts of your routine? We often fixate so much on the habit itself that we neglect how it will affect different parts of our lives. This is a question I did not ask myself, but I wish I did, as it would have made things easier. For example, I wish I accounted for the fact that I wouldn’t have the energy to make dinner after working out, I needed extra sleep to account for the physical exercise, I had to do an extra load of laundry a week, etc.

Make a commitment.

You’ve done everything you can to mentally prepare yourself for your habit. The only thing left is to commit to it. Set a time and date when you’re going to start. Contrary to what most people will tell you, it doesn’t have to be today or tomorrow. If the motivation wanes after just a few days of waiting, you will likely fail anyway, as your emotional trigger isn’t strong enough.

I started on a day where the rest of my schedule was flexible. I chose a day that wasn’t too hot, there was no chance of rain, and I could finish my work early. I could also account for any unexpected disruptions that may come up.

Be patient, be kind, and repeat, repeat, repeat.

One of the mistakes we make when we try to build a habit is that we idealize and set too high of a bar for what success looks like. In the first few weeks, the only two things that will determine whether you’re successful or not are attendance and participation. That’s it. If I told myself on day one that I was going to play basketball for an hour, do several drills, and do a bunch of suicides (a sprinting drill), then I was destined to fail. The reality of day one was that I realized how out of shape I was. I broke a sweat and was panting just from chasing the basketball after I missed a shot. I felt so self-conscious on the court; my body felt uneasy with the side-to-side and unusual movements, and I didn’t get past 30-35 minutes.

However, I wasn’t demoralized or defeated. I went in with a low bar for success. I knew this was a process, and I went there and did it, and that’s what mattered. During my next session, the only thing that would matter is if I showed up and tried again. After several weeks, you can begin to set metrics and goals but now is not the time. You need to positively reinforce the success. If you look at it in any other way, you’ll be disappointed and want to quit after a few days.

Use data and adjust your plan again.

Even after just a few days, you’ll have several new data points that you can use to correct course and refine your habit. It’s extremely important to reflect on what is working and what is not and think about optimizing your new routine or practice.


For example, I thought that working out would only be a 45-minute commitment, but adding in getting ready to go, commuting to the park and back, and showering turned it into a 90-minute commitment. On top of that, I was much more tired and sore, meaning it took me longer than usual to do just about anything else. I also took a look at the workout itself. I slowly started to incorporate drills and realized I needed to wear specific types of shoes to prevent my ankles from hurting. I also needed to watch videos on different stretches to prevent soreness. Through this, I learned that this would be an iterative process. Almost daily, I thought about how to optimize my routine or research different things about working out.

Think through all the different things that will break your habit and adapt.

When building a habit, you usually need a consistent and predictable routine to get through the first couple of weeks. This is why I would never recommend starting a habit when you know you’re about to go on vacation or have a hectic work schedule where you will be working more than usual. However, you can only stay in this bubble for so long. At some point, you must face reality, which is full of traps that will try to break your habit. Given that, you have to try to be one step ahead and anticipate what will fail. I had to think carefully about things like what I’d do if it rained on a day I was going to work out or if I got to the park and all the hoops were taken. I made shifts to my routine to prevent them from becoming significant obstacles. For example, I knew that as the summer progressed and kids were on summer break, the courts would get filled in the evening, and it would get too hot to work out. As a result, I slowly shifted my workouts to the mornings.

However, other challenges ahead of me were harder to control (i.e., being away from home for a week). In those circumstances, I had to constantly reinforce to myself that I cannot chase perfection. I was visiting family for a week and determined to keep my basketball routine, so I researched and found a park nearby with basketball courts. When I reached my family’s place the next day, I proudly drove to the park but found no basketball court there. At first, I was really disappointed and demoralized. What do I do now?

I did some basic bodyweight workouts to break a sweat (e.g., jogging in place, jumping jacks, etc.), but I felt out of place and disappointed. This wasn’t nearly as vigorous as my basketball routine is, and I was stuck there for a week. I thought about what I could do to adjust though, and the next day, I adapted. I reminded myself that success is a long-term game and is determined by attendance and participation. The next day I went back to the park, went for a warmup job around the park, and then I practiced some dribbling drills with my basketball. Was it as intense as my regular workout? No. However, I showed up and did what I could. What I learned is that when faced with adverse circumstances, you can only focus on what is in your control and try to stay where you are on your journey. If you fall back a bit, you just need to get back up when things calm down. For me, this meant there would be days when I couldn’t play basketball. However, I could have a lighter, maintenance-type backup workout (e.g., jumping jacks, going for a jog, resistance bands) that would help me maintain the endurance I had worked so hard to build.

What we expect growth to be like:

What growth is actually like:

Final words…

“Success is when hard work meets opportunity.”

A lot of building habits come down to good circumstances and luck. Sometimes, you need the stars to align. However, you must be ready to pounce on the opportunity when they do. After having successfully built a workout routine that has lasted several months, I’ve learned that there is a loose formula that can help with building habits:

  • Identify a clear motivator, usually a strong emotion that will give you enough activation energy to get started
  • Spend time in deep reflection and researching the ins and outs of how and why you are building this habit
  • Commit and be kind to yourself along the way. The most important criteria for success are attendance and participation
  • Collect data and keep iterating on your routine – do your best to optimize it
  • Think about why you’ve failed in the past or what will make you fail in the future, and try to be one step ahead of it. Adapt when you need to.

Lastly, you need to get some reward from what you do, and the reward has to come from the habit itself, not something else. I’ve seen a lot of books that say to reinforce a habit, you need to give yourself a treat after you successfully complete a habit (e.g., get yourself some ice cream), but that simply is not going to work. It’s too easy to game the system and give yourself the treat without engaging in the habit. The reward has to come or be tied to the habit itself. For myself, I feel so empowered and confident that I am succeeding in something I failed at for so long that it makes me feel that I can succeed in doing anything else, too. On top of that, now that I’ve adjusted to a basketball routine, it often is the highlight of my day. It’s the one activity I’m doing for myself; no one can complain or have a problem with the fact that I’m doing it, and it’s much easier to be in the moment (in large part because I’m too physically tired to think about anything else 😅)

Optimism wins

Way too many people out there have this belief that optimism is synonymous with delusion and/or being unrealistic. I hear it all the time that optimists are just sunshine, rainbows, and flowers. They don’t see or acknowledge the hurt and pain that’s out there in the world. They are optimistic because their life is good. Their reality is distorted. One individual on Fox News went so far to say that optimism was at fault for why a US soldier killed 16 Afghan civilians because “soldiers are actually taught to deny stress and trauma, and false bravado is actually encouraged.”

But did you ever stop to think that maybe optimists are the realists? Maybe their life is good BECAUSE they are optimistic? The truth is that optimism and positivity wins. A mild dose of pessimism has its utility, and extremism of anything is unhealthy, but by and large, optimism wins. According to the research shared in Martin Seligman’s book on optimism, on average, optimists have better physical and mental health, and they are better achievers than pessimists. It’s just a fact.

That being said, optimism is not necessarily what you’ve been fed by other people. It’s not just turning everything negative into something positive, and nor is it something you can experience by just having a positive pep talk with yourself while standing in front of a mirror. Ultimately, the way you distinguish an optimist from a pessimist is based on how an individual explains to themselves the bad things that happen to them in their life.

Optimists vs. Pessimists:

When something bad happens, an optimist WILL feel bad. Of course they will. They’re human. It’s not just that their glass is half full. They’re not delusional. However, the difference between them and the pessimist is that the optimists’ feelings of helplessness are temporary and they are more likely to contextualize the bad event. The pessimist, on the other hand, views bad events as more permanent and a general occurrence in their life that is inevitable and unavoidable.

The pessimist is very passive and helpless. The pessimist accepts the inevitable doom of his or her life, and a bad event is just a reflection of that. The pessimist feels they cannot really do anything about the situation. The optimist is also passive and helpless, but that’s very short lived. Soon the optimist realizes that:

  • The bad event is not a reflection of my life; it happened because of X, Y, and Z. Maybe I can’t do anything about this situation, but I can do A, B, and C to move forward.
  • Bad things happen, and they suck, but that will not stop me from growing, getting better, and achieving my goals. Just because I feel bad about this doesn’t mean I need to feel terrible about my entire life.
  • I have the power to move on and not feel terrible anymore.

On average, both the optimist and the pessimist experience the same bad events. Furthermore, they feel equally as bad when bad things happen to them. However, the difference is that soon after, the pessimist enables the helplessness whereas the optimist suppresses it. The pessimist feels a lack of control while the optimist takes control. The pessimist becomes passive while the optimist becomes active. Optimists forgive themselves and the negative events in their lives whereas pessimists hold a grudge.

When it comes to how we perceive the good things that happen to ourselves in life, we see almost the exact opposite thing happen. Optimists view the good events as more permanent and a general occurrence of their life whereas pessimists view good events as more temporary and are more likely to contextualize or think it is a fluke. An optimist takes a good event, savors it, and then is motivated to replicate the good event (they feel a sense of control). A pessimist, on the other hand, sours some of the good feelings by thinking this occurrence is not sustainable and is a result of luck or chance.

Final words…

Both optimism and pessimism are habits. The good news is that optimism can be learned and pessimism can be unlearned. Again, it’s not to say that all optimism is good and all pessimism is bad (that’s a conversations for another day). Also, it  doesn’t mean that optimists can’t have pessimistic moments or vice versa. A bad event is a bad event and everyone is going to feel bad about it. The difference, however, as Seligman states in his book, is that “in optimists, a failure produces only brief demoralization” (p.76). It’s short-lived. Optimists rebound faster and take control of their situation. This is why they are generally healthier, happier, and higher-achievers.

Optimism wins.