Kaizen Newsletter #70 - How I stopped avoiding my day job by leaning into fear

Thoughts on overcoming fear, magic moments in communities and success

Hey friend 👋,

Welcome to the 70th 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.

Sadly, pausing the audio newsletter experiment for now! Doesn’t mean that I won’t do it again, but it wasn’t as enjoyable as I thought it would be and it wasn’t as popular as I thought it could be. I’m actually super excited for this edition, as it’s probably one of the best ones I’ve ever written (IMO). Curious to know what you think? As always, if you have any other feedback or if you were one of the few that enjoyed the audio format to come back, please let me know!

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


For the past three years, I've been hopping from job to job to job. Never lasting more than a year and a half at each one of them.

My main excuses?

"I don’t like working environments where I have to wait 2 weeks to get an approval because it’s escalated to my bosses bosses bosses boss."

"It sucks needing to prove yourself to the company by helping execs do their internal powerpoints."

"This is not what a product manager is supposed to be doing."

I finally found a job 5 months ago that seemed to check all of the boxes.

  • I was in a fast-paced startup environment which means decisions are made almost immediately.

  • I’m evaluated based on my performance and not how many powerpoints I’ve helped with.

  • I was doing proper product management.

  • I’m aligned with their mission to democratize treatments for sleep disorders.

And yet, here I am, once again, finding new excuses as to why I'm not being productive or why I don't like my job.

After trying to blame my job three years in a row, it was time to look at what remained constant throughout this period of time - my inability to be as productive as I wanted to.

Reflecting back on my working experience, there is one particular moment that I believe was the élément déclencheur of my fall off in productivity.

Back in 2016, I had just finished a 6-month stint in Phoenix working 60-80h a week and was living the dream consultant life. I was living in fancy hotels, eating at restaurants every day, drinking (almost) every night with my colleagues.

When I got back to reality, I realized that I was burnt out.

Although I loved the experience, I also told myself that I would never want to do it again. I realized how pointless it was to dedicate 90% of my waking hours to some big corporation with the only reward being able to update my LinkedIn profile every 2 years signalling that I got a promotion.

Since then, I started valuing my own freedom over everything else.

I was scared of going back to a reality that meant not being able to meditate in the morning, it meant having meetings all day, it meant not being able to work on my personal projects, it meant not having time to workout, it meant not being able to sleep 8h a day.

And that was a deep fear that was holding me back.

It's as if I had a really bad experience with an ex (my burnout) and every time I would try and date new girls (going to different companies), this bad experience would always be at the back of my mind. So every time this relationship would get more serious (whenever I would start a new job), I would sabotage the relationship (change jobs) because I was afraid that the same thing would happen again (I was afraid of burning out again).

But if ever you want to overcome that fear, the best way is to lean into it.

And trust me, it’s scary as fuck. But as the saying goes, behind every fear is the person that you want to be, and that alone is enough to motivate me to overcome it.

Tangibly, this meant trying an experiment. I wanted to prove to myself that if I was more devoted to my work, then I would still be able to work on my own projects, that I would still be able to meditate and not affect my life as much as I fear it would.

For one month, I am forcing myself to set aside a four-hour window (which I call my core working hours), where I cannot go on Twitter, or Youtube or work on my personal projects and can only do focused work. The only other things I’m allowed to do is reply to messages, check my personal email and can also choose to not do anything.

The worst that could happen? I could potentially go back to what I was before. A 9-to-5 zombie kid working 60h-80h a week.

But can this really happen? I don’t think so.

At this point in my life, freedom is so important that I will almost immediately stop this experiment if I see it negatively impacting me. After two weeks, I’ll compare the hours of sleep I got, the number of tweets I sent out, the number of times I wasn’t able to meditate in the morning, and the number of meetings I have per day and see if this increase of work productivity was worth it.

However, I’ve only started doing this for 2 days, but I’m already seeing a lot of improvements in my productivity (funnily not just at work, but on my personal projects as well)!

Now does this mean that I want to try and climb the corporate ladder again? Not at all. My end goal is and will always be to be as free as possible. I see this experiment more as a way for me to overcome one of my fears and to also feel good about myself at all times of the day (instead of dreading my 9-to-5).

If ever there is a better opportunity that presents itself, or if I see traction in my own work, then I hope I realize it and hop on that train.

But till then, why not make every waking moment of your life more enjoyable?


🤔 Thoughts

📈 Thoughts on Success

I love it whenever I see tweets like these. I love it because it's a simple reminder that there's no real secret to success.

My current thesis is that you're able to make a living out of (almost) any craft you want as long as you're able to do it consistently for three years straight while shipping something related every single week.

  • If you want to be a better writer, then publish something every week for three years straight.

  • If you want to become a YouTuber, then post a new video every week for three years straight.

  • If you want to become a dancer, then post a new dance video every week for three years straight.

If you want to become a product manager, then analyze a product or build a product every week for 3 years straight.

The publishing portion will inevitably rally an audience for you and the consistency will bring in the expertise in the craft that you choose.

Although I have no idea how I will be able to make a living out of my writing, I trust that it will manifest itself somehow :).

Question for you, what craft do you want to focus on for the next three years?

Leave a comment

🎩 Thoughts on Magic Moments in Communities

When building a product, you eventually want to find the "aha moment" for your users. Meaning, the moment when your user understands the value that your product provides to them.

For Facebook, this was "7 friends in 10 days." For Slack, this was "2,000 messages."

And the reason why this "aha moment" is so important is that when your users get to that point, it becomes very unlikely for them to churn.

Nick deWilde, a fellow Kaizen subscriber, posits that there's something similar when joining a community.

In his essay, The Social Architecture of Impactful Communities, he refers to this moment as the "magic moment." Similarly to a product, you also want members of your community to understand the value that your community provides as fast as possible. And when your members get this magic moment, this will push them to stay so that they can get more.

A community that I'm part of that does this very well is Compound Writing.

As Nick describes in his essay (we're both in the community):

During onboarding, the founders explain that the core activity of the group is editing. You post your work and get a bunch of insightful comments. The first time you post something to the group and end up with a Google doc full of insightful comments, you can feel the value that the community has to offer.

The reason why this is important to highlight is that there are very few communities that think of finding their magic moment. If members are not able to find it quickly, there’s a very good chance that they become inactive - and that’s not what you want.

That’s why community builders should really think of the value they can bring to their members outside of just having a really cool community.

How I see it, is that you want people to “come to the tool, stay for the community.”


🐦 Tweets

There's always someone that's not going to be happy, so I eventually learned to stop caring as much. Been much happier since!

Simple, yet not enough people do this.

Can we all collectively agree to stop doing daylight savings?


🙏 Shoutouts

Shoutout to both Stew Fortier and Tom White for offering help for a cold email I wanted to send out. Super helpful and made my cold email so much better.

Also huge shoutouts to Étienne Fortier-Dubois, Anant Kapoor, Kushaan Shah, Mikko Jarvenpaa, Rishi Pethe, Derek Browers, Devanshi Jain and Pranav Mutatkar from the On Deck Fellowship for helping out with my newsletter. They've made it SO much better.


👋 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.

Share The Kaizen Newsletter ⛩

See ya next Tuesday,

Alexander ✌️