Developing Good Habits – 5 Challenges You Will Encounter

Let’s talk about developing good habits in your life. I am at a stage in my life where I am trying to improve in multiple areas. This includes learning how to grow my online business and also overcoming my shyness which has held me back in life, especially around the opposite sex. Each of these areas involves a lot of change – deviating from my current lifestyle and the way I’ve always done things. The transition feels unnatural, and oftentimes scary, as I try things that are new. I spend time overthinking, questioning whether these things are a good fit for me and worth committing too. Since I have OCD (Obsessive Compulsive Disorder), I probably overthink more often than most, obsessing about thoughts that are trying to distract me from my mission in life.




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I admit that changing your life can be hard, and that is why I wanted to share 5 challenges that you will encounter when you are trying to implement good habits into your life. They can really mess with your mindset and interfere with your success.

To give you an example of these 5 challenges in MY OWN life, I will relate each challenge to my shyness and social anxiety goals. Specifically, my experience going to the mall and talking to people I’ve never met, and improving my interactions with the opposite sex. I was actually inspired to make this blog post after going out last night and being frustrated with my experience. My attitude and mindset caused me to have doubts about whether this process is right for me and forced me to take a second and view the situation logically.






The first challenge you will face is focusing on your shortcomings instead of your progress. This past week, I went out on Thursday night and on Friday night to talk to some strangers. If you follow me on Instagram, you saw that I came home Thursday excited about the progress I was making, and very excited to go out and do it again. My interactions were great, I enjoyed working with my wingman, and everything was awesome. However, when I went out Friday, I felt very different. I wasn’t in as good of a physical state, I had limiting beliefs that started to creep into my head, and it just wasn’t that fun overall.

The key here though, is that despite having these shortcomings during my night out on Friday, there was still a lot of progress that happened. I just wasn’t focused on it, and I wasn’t rewarding myself for it. A common saying is, “What gets rewarded gets repeated”. So while you work on implementing good habits, it is always good to reward yourself, even for the smallest wins. This encourages you to continue moving forward and stay focused.

So after re-evaluating my night out, I started to see the progress I made. I did well at going up to girls that I was found attractive and giving them a compliment. For example, “I just wanted to come over because I thought you were really cute, and I wanted to say hi”. This is something I was able to do a lot more easily than before, and my approach anxiety was lower.




The second challenge you will face when developing good habits is the tendency to want to go back to your original habits, by thinking that your new ones aren’t “right for you”. When I came home on Friday night, this was a feeling that took over me. I started to think: “Well…this wasn’t fun and it was uncomfortable…maybe it just isn’t right for me, maybe this isn’t who I am”

Traditionally, I never thought of myself as someone who would go out and cold approach people or get into picking up girls. I still don’t believe in doing pickup, specifically using artificial lines to get a girl or being disingenuine. It is better to be natural, and express who you really are on the inside. I think that embodies true inner confidence. Nonetheless, I still had to practice cold approaching so I can get over my shyness and fear of rejection.

I felt very “out of my element” walking up to people I’ve never met, but I have to remember that developing good habits is a long process. It requires mastery – the ability to stick with the process, give it a chance, and see it through. I have to remember that just ONE DAY AGO, I had an excellent time doing this stuff.

I also felt like I wanted things to be too perfect. For example, there were periods where I and my wingman weren’t talking much throughout the night. I felt like it was bringing down my vibe which caused me to be annoyed. This lead me to question whether I should be doing this stuff with him or with someone else. But look…..when you are trying to develop good habits, things aren’t always perfect. You should take advantage of situations where you have the opportunity to grow.




Another challenge is being impatient and wanting instant gratification or success. In terms of talking to the opposite sex, you get impatient and want your interactions to be good right away. Maybe your goal is to get a phone number or kiss the girl. This stuff is instant gratification, and lead you to become attached to the outcome of the situation instead of focusing on your larger goal.

You have to understand that this is a long-term process, and you may not see results right away. You need to make incremental progress and focus on what you are improving on each day. It is important to realize that you will get better every time you go out. If you had a bad time today, then so what? You will do better next time.




Another challenge is focusing on what others want instead of what YOU want. For example, sometimes I and my parents don’t agree on everything. I have more of a growth mindset than they do and am actively focusing on ways to improve myself. I believe that there is a true potential within me that I haven’t cultivated yet. My parents don’t always encourage those views. Sometimes, they encourage me to take a break or watch some TV and do things that don’t align with my goals. That can be challenging for me because I have to respect what they say, but take it with a grain of salt and think about whether it will actually benefit me.

When I told my parents I was going out and talking to strangers, they thought it was pretty ludicrous and pretty strange that I would take that approach. But the fact of the matter is that SO MANY people who have been shy have taken this approach and had success with it. I also think a huge benefit is that most of these people you approach in a mall, etc. are people you will never see again. So even if you mess up, there are no repercussions.


power of habit


So take what you hear from others with a grain of salt. Make sure to surround yourself with positive and encouraging people so you get to hear more statements that serve you well instead of degrading ones.




The 5th challenge you face while trying to develop good habits is trying to support your progress without taking care of your physical body and health. I found that there were a couple things that were responsible for me not feeling at my best when I went out Friday:

  • Dehydration
  • Sleep deprivation

Firstly, I was dehydrated. I ate a healthy meal for dinner but I didn’t have much to drink with it. I was also very nervous, so I have a tendency to have to use the washroom a lot if I put fluids in me. As a result, I was dehydrated which likely affected my performance mentally and physically. 

Secondly, I was sleep-deprived. It was the end of a long work week and I had stayed up later to work on my online business on some of the days. I also woke up early to do my morning ritual. I need to focus on getting better and more steady sleep. 

It’s very important to focus on your health, as it can support you with all your OTHER goals. Working on a business takes a lot of hard work, so you need the proper energy to support you. Going out and being social also requires that you have enough energy to talk and enjoy yourself. 




Overall, I think that these 5 challenges can help you when you are trying to form good habits. They will keep you focused on the long-term process and keep your mindset in check.

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