The Kaizen Newsletter #65 (29/09/2020) - And my next challenge is...

Thoughts on challenges, getting out of your comfort zone and creation vs curation newsletters

Hey friend 👋,

Welcome to the 65th edition of the Kaizen Newsletter ⛩, a weekly newsletter where I share my thoughts, new ideas I learn and make weird connections between self-improvement, productivity, product, tech, sports, anime.

Two weeks ago, I shared that I was applying for a writing fellowship and the results are in…. ya boi made it! Super excited that I’ll be joining the first On Deck writer’s cohort starting October 10th and can’t wait to share my learnings and stories with you all. If you want to know why I’m so excited, I’d suggest reading this post from a past fellow describing the On Deck community.

(if you got referred to this page by a friend or are simply visiting you can subscribe here👇)


This past Saturday, I completed 75 hard, which is a 75-day mental toughness challenge.

In short, I had to follow a diet (that includes no alcohol), drink 4L of water, exercise twice per day for at least 45 min (and 1 needs to be outside) and read 10 pages every single day for 75 days straight.

I’m not going to go into details of my experience with 75 hard yet (I’m currently writing it up for a future newsletter), but I still wanted to explain why I love doing challenges, and why they are beneficial (especially the ones that are structured like 75 hard).

The main reason why I enjoy doing challenges is that I’m an ultra-competitive person. I’m pretty bad at staying motivated for a long time, so doing a challenge allows me to gamify my life where I can turn everything I do into an objective that I need to meet. And since I hate losing, embarking in a challenge provides me extra motivation to continue doing things even when I don’t feel like it.

The main benefit that challenges bring you is as I mentioned above, extra motivation to actually complete a certain activity over a period of time. I’ve done multiple challenges during my life, but I really feel that the format of 75 hard is ideal for challenges.

In my opinion, the best kind of challenge is when they are set up as daily challenges. Doing something daily forces you to be fully committed to the challenge. You have no breaks which means you always have to take your challenge into account every single day. Doing a daily challenge also makes it easier to turn that activity into a habit.

Then let’s talk about the length of the challenge. Normally, you would see weekly or monthly challenges, but I feel that both lengths are way too short. The reason why you shouldn't do challenges that are less than a month is that you are often still very hyped by the time you hit a month. I remember in my first month of doing 75 hard, I thought to myself that this challenge would be a piece of cake. It's only in the second month where I started struggling and motivation was low. Doing something for over a month introduces a mental toughness aspect to the equation, which is what I enjoy. It's usually during the second month where you start hitting walls and have to find ways to overcome them.

So this brings me to my next challenge. Although I just finished 75 hard a few days ago, I decided to start another on October 1st that will bring me all the way to the beginning of the year.

It’s called the 100 days - Kaizen challenge.

For the past year or so, I’ve thought about learning a new skill other than writing. I wanted to find an adjacent skill that would compliment both my writing and my product manager role at work.

To me, there are three skills that I really want to learn but was never able to decide which one to choose. It was either design, coding or copywriting.

Although all three are super valuable, I ended up choosing copywriting as the skill I wanted to focus on. I already bought a few copywriting courses and never gave it more than a few days to learn. I also think copywriting would set me apart as a product manager because very few have a copywriting background or choose to learn copywriting. I also believe that learning copywriting will directly help improve my writing skills as well. And what really put the nail in the coffin is because one of the people that I look up to the most on Twitter, Tej Dosa, is also a copywriter.

So I already knew that I wanted to dedicate time to building a particular skill in my new challenge, but I also didn’t want to lose the habits that I developed from 75 hard.

So I took the 75 hard skeletons and modified to include the skill I wanted to improve on and also added some meditation because I’ve been wanting to re-start for a while.

In the end, this is the challenge that I settled on:

Repeat for 100 days

  • 30 min of [skill you want to learn]

  • 30 min of exercise

  • 20 min of meditation

  • Drink 3L of water

  • Read 10 pages per day (fiction or non-fiction)

  • Say out loud "I love myself" 10x a day

I wanted to do this challenge until the end of the year but found that 91 days was an ugly number, so decided to bump it to 100.

I know it’s pretty last minute (you have 1 day), but if you’re up for the challenge I invite you all to do the challenge(or even just a portion of it), with me. If any of you are interested, reply to this email saying that you're in! And if we are enough, maybe I'll do a slack channel or telegram/WhatsApp group to have an accountability group setup.

Anyways, I’m super excited to start this off and we’ll see if I can accomplish this one as well!

Now, on to the newsletter.


🤔 Thoughts

🛋 Thoughts on getting out of your comfort zone

One of my friends has been reading my newsletter for a few months now and told me straight up that sometimes reading my newsletter caused him to be anxious because he feels that he's never doing enough and that he can always do more to be better and self-improve.

I found that comment funny because that's usually how I feel as well even though I almost always write about self-improvement and productivity, I never feel that I'm doing enough either.

The discussion became interesting when he told me didn't feel that he was starting to dread Mondays whereas he used to enjoy waking up every morning and going to work.

Curious, I asked him if he ever thought of leaving his job and finding a new one?

And his answer was that it's hard for him to get out of his comfort zone, especially because changing jobs is such a big move.

And I agree. Changing jobs can be a huge amount of stress and most often than not, the grass is not always greener.

But one thing I did want to share with him was my heuristics on when I want to make decisions. The thing is, it's really hard to get out of your comfort zone and sometimes this hinders you because you then settle in an unwanted or undesirable situation.

So to counter this, I try to ask myself two questions.

The first one is "In my current situation, am I happy and/or fulfilled?" This will force you into introspection and will create awareness of the situation. You won't necessarily get an answer right away, but at the very least, it will make you think about the situation. If eventually, you get to yes, then that's perfect! If not, then that means that you should probably do something about it.

Which leads to the next question. "What small experiment can I test out that will potentially make me happier/more fulfilled?" In the case of my friend, is quitting your job necessarily the right answer? Probably not. But if it's a big decision such as quitting your job, I would rather test out the waters and see if there small tweaks that I can do in my daily life that could help me gain back the happiness and fulfillment. Maybe it's finding a hobby. Maybe it's starting to date again (maybe after COVID settles down). Try a lot of little things to see if that could help and if not, then maybe it is time to think of new jobs. But what's important is to not continue being miserable. Help yourself out.

The trick to combat staying in your comfort zone is prioritizing your happiness and fulfillment. If you prioritize your happiness and fulfillment above all, then that will eventually push you to take action.

🖋 Thoughts on curation vs creation

While I was writing this newsletter, on Tuesday, my friend Akiff tagged me into one of his threads on Twitter. The premise is that Akiff has been pretty busy lately and has had less time to write longer-form original content and thus pivoted into a curated newsletter, instead. But realized that both he and his audience prefer creation newsletters vs curation newsletters (which is normal). He was then asking a few Twitter friends about their opinions and I got tagged into the thread.

This is a topic that I've been thinking about a lot since the release of my newsletter, but have never written about it. So I wanted to do an experiment and decided to share my thoughts on this newsletter instead of simply replying to the tweet (which I did end up doing, but very briefly).

Before I dive into my thoughts, I do want to mention that the main reason I write is to understand my own thoughts first and foremost and optimize for engagement second. So keep that in mind when I explain myself.

So now that the small disclaimer is out of the way, here are my unfiltered thoughts on curation vs creation.

Since I come from a product background, it's pretty much instilled into me that you want to be shipping iterations to your product as frequently as possible. If you can ship daily or even hourly, then DO IT!

By shipping frequently, you are able to build the shipping muscle which allows you to bypass "perfectionism" and also produces good feedback for your product (in this case, your product is you and your brand).

So the first thing I would suggest is to maintain at the very least a weekly schedule for sending out your newsletter, if possible. Although it's not my preference, I would rather ship a curated newsletter than nothing at all. Eventually, shipping becomes so ingrained that it just becomes a part of your week.

For example, with my newsletter, rain or shine, energized or tired, a good week or a bad week, I know that every Tuesday I will be sending out a newsletter no matter what and haven't missed one since the end of March.

But what if you really don't want to ship out a curated newsletter? I'll be the first to admit, I also got tired of curating for my newsletter, which is why I changed the format earlier this summer (hopefully you also like it better). Creation is a lot more rewarding for both the reader and the writer, but it obviously takes a bit more time to write-up. But if you're not able to create lengthy pieces every week, I would suggest shipping a shorter newsletter that contains original content.

A great example of a newsletter that does this is Screenshot Essays. The author, Eric Stromberg sends out a smaller essay that fits on your phone screen (hence screenshot).

The last thing I would suggest is not to stop creating lengthy original content completely. It's much better to release one piece of content than none at all. So if you can't send it out every week, then maybe try and send it out once every month or two months. And the rest of the time, stick to either curation or shorter-form creation.

I'll end this by asking you a question. What are your thoughts on creation vs curation? Which form of newsletter do you prefer?

Leave a comment

🐦 Tweets

Cool story-telling structure.

One of the greatest "skills" I've learned as an adult.

This is honestly so cool. Love the Dad's reaction!

🙏 Shoutout

Shoutout to Kit, Jackie, Fred, Kenny and Linda for the cool Toronto trip. Glad to spend a chill weekend with good friends and was able to eat good food 🍲 and shop at Uniqlo 🤑.


👋 End Note

If you want to know what I'm up to now, you can check it on my website here.

If you enjoyed the Kaizen Newsletter, then it'd be cool if you can share it with your friends.

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Thanks for reading and see you next week!

Peace ✌️,
Alexander