In my Year 2 reflection, I committed to writing monthly retrospectives.
I was inspired by Michael Lynch, a fellow blogger and solopreneur. He’s a few years ahead of me on the same path: he left Google in 2017 to work for himself. In fact, his article “Why I Quit Google” played a part in my own decision to leave and write a similar essay.
I found his monthly updates fascinating. They were a peek into the messy world of entrepreneurship, a valuable reminder that chasing your dreams is a game of resilience. In the first year, he only made $2k. Most people would have given up then, but he didn’t. Five years and many projects later, he just hit a run rate of $1M. The lesson: good things come to those who persevere.
Recently, we became friends. In one of our calls, he noted how helpful the monthly reviews continue to be. Not for others, but for himself. They forced a clear strategy. They revealed hidden opportunities. They exposed mistakes he otherwise wouldn’t notice. Even if no one else read them, they still served a purpose. There was no downside.
Initially, I hesitated to follow suit. My yearly retrospectives are already time-consuming enough. I didn’t need to add another obligation. But the more I thought about it, the more it made sense. It was an investment.
Writing public monthly retrospectives brings several benefits.
First, it leads to more insightful reflections. It would help me dig deeper into the issues I’m facing and why.
Second, it holds me accountable to my goals. I know I’ll have to answer to you in a month.
Third, it tightens the feedback loop. This addresses a problem I noticed in my last yearly reflection - many goals slipped through the cracks for months at a time. It ensures I’m checking on them at least monthly and catching mistakes early.
Finally, as an added bonus: it documents the journey. This is for my own future nostalgia and to pay it forward so others can learn from it. It was certainly reassuring to know that others ahead of me made it work - I hope to do the same.
So, here goes.
Note: This is a very personal and in the weeds retrospective. I’ll iterate it over time to find the right balance between what’s useful for both of us. I’m always open to hearing feedback about what you’d like to see more or less of!
Health + Happiness
Goal: Wake up by 7am.
I woke up between 8:00-8:30 on most days as a result of sleeping late. Screens before bed kept me up.
What I learned:
- Late-night screen time is a double whammy - you lose track of time on a device and it disrupts your ability to sleep even after you put it away.
- It’s better to sleep earlier and work the next day. Working late just means you’re eating into tomorrow, which has a cascading effect.
- Wind-down time is a necessity. You need some separation between screens and bedtime.
Going forward: I don’t know the exact amount of no-screen time I need, but I’ll begin by experimenting with 30 minutes before bed. I can use it to brush, read and plan my next day.
Goal: Eat a daily serving of fruits, vegetables and probiotics.
I successfully added this to my routine: an afternoon break for fruits with yogurt and a side salad with dinner. Both habits were well worth the 10 minutes they took.
The obstacle with the afternoon snack was inertia. When I’m in the zone, I didn’t want to lose my momentum by stepping away. But when I finally got up, I enjoyed the small break.
Fortunately, the side salad wasn’t as much effort as I expected and I felt instantly better for having fresh vegetables.
What I learned: Find the low-hanging fruit (apt analogy, eh?). Small habits can have a disproportionate effect on your immediate wellbeing.
Goal: 1 hour of daily meditation + track emotions.
I maintained my meditation practice and kept mental track of my emotions. Overall, I’m still at peace and am able to let things go quickly. However, I do sense my awareness waning.
What I learned: Results can lag the habit (or lack of). It’s important to be mindful of recent changes you’ve made.
Going forward: I’ll keep an eye on my awareness and actively meditate to grow it. (Vipassana has some techniques for this.)
Goal: Catch up on journaling.
I hoped to kickstart this habit by covering my backlog. It dates back to October 2021. However, I didn’t make the time. In fact, I didn’t write a single word in my journal this month.
I attribute my failure in part to feeling overwhelmed by the amount of catch-up necessary. As time passes and the uncaptured window expands, it gets even more daunting.
What I learned:
- You don’t find time, you make it. I need to schedule it into my week.
- Make your goals approachable. In hindsight, catching up on 15 months was too much. It prevented me from even starting. Instead, I could have just committed to writing for 1 hour every week.
Going forward: I’m traveling for all of February, so I aim to write for an hour on each flight.
Goal: Go to the gym 3x/week.
I injured my shoulder almost two years ago. Since then, I’ve been focusing on rehab. It finally recovered a few months ago, but I procrastinated on joining the gym.
This month, I pulled the trigger and set out to go 2x/week. I didn’t have to do a full work-out, I just had to go. This worked incredibly well - after just a few visits, I converged on an exercise regimen that I’m happy with.
I ended up exceeding the goal with 3 visits/week and complete workouts.
What I learned: Habits first, outcome later. Just start. You don’t need to know everything, you’ll figure it out as you go. But without the habit, you’ll never get the results.
Goal: Complete 30 work sessions per week.
For this challenge, I only counted the sessions where the timer went off. Any extra work didn’t go towards the tally. I did this intentionally to solve a long-standing problem: working past the bell.
Why is this a problem, you ask?
First, I couldn’t get an accurate estimate of how long I worked. I figured that tracking it precisely could help me get more done: what gets measured gets improved.
Second, I get in the zone and lose track of my priorities. I would end up focusing on the wrong things, e.g spending an hour wordsmithing an email. The timer helps me contain my effort.
It serves as a useful reminder to take a step back and assess whether the task at hand deserves the effort I’m devoting to it. It usually didn’t. This got me to move faster.
Overall, the goal was a success. It even exposed an issue: where is my time going?
At 50 minutes each, 30 work sessions per week adds up to 5 hours a day. Between the meditation and exercise, I work from 11am-7pm. Embarrassingly, I don’t know where the remaining time went.
Sure, part of it is untracked work. I still go past the bell when I’m on a particularly juicy problem. However, I’m sure there are other inefficiencies to be squeezed out. I’m going to track my time to find out. (I already do this, but inconsistently.)
What I learned: Focus is a double-edged sword. It has to be applied towards the right problems. Otherwise, it’s only the illusion of progress.
Going forward: I’ll track my time towards the goal of doing 40 work sessions/week.
Goal: Frontload the important tasks.
When planning my day, I now schedule the most important and brain-intensive tasks first. Even if I don’t get to all of them, it ensures that I’m moving the ball forward in a meaningful way and not getting trapped in minutiae.
I reserve errands and lighter tasks for the end of the day. This simultaneously manages my energy and timeboxes the effort.
This technique has worked wonders for my prioritization. I feel a renewed sense of momentum and hope now that I’m focusing on the bigger picture.
What I learned: Busy work is gratifying, but doesn’t move the needle in the long run. It’s important to do it, but don’t let it expand to fill up your whole day.
Goal: Reach out to 50 creators.
Despite my improved prioritization, I didn’t make time for this. As I mentioned, I couldn’t get to all the important workstreams. This is an example of one that got preempted by more urgent tasks.
In hindsight, this was a mistake. It should have been higher up on the list. Partering with established creators is one of the few outcomes that can result in a step-change improvement for Habit Gym. In comparison, the upgrades I’ve been making are incremental at best.
What I learned: Look at outcomes through the lens of exponential growth vs linear. It’s often worth sacrificing the latter for the former.
Goal: Publish every weekday on Twitter.
I successfully posted every day, including weekends. I started small, with light content. Just like the gym, I’m establishing consistency first - I’ll optimize later.
At face value, this goal may seem off-brand considering my aversion to social media and digital addiction. But, I have a more nuanced position now. Yes, social media is still dangerous. Frankly though, it’s necessary for spreading any message. The truth is that almost everyone uses it - you have to meet people where they are.
As I mentioned in my last yearly reflection, I’m going to write with more regularity. I chose to start with Twitter for two reasons.
First, it’s short-form. That helps me write more often and iterate faster. Remember: quantity is quality.
Second, it’s more discoverable. It’s much easier for a tweet to reach a large audience than a blog.
What I learned:
- Don’t be an absolutist. You have to navigate nuance to achieve your goals.
- Create more than you consume. This is what separates Twitter being a productive activity for me as opposed to a time sink. (Feed blockers are your friend!)
Goal: Add 1 social feature.
In my yearly retro, I hypothesized that community can aid in habit building. In the spirit of moving fast, I just launched an initial version: a new Habit Gym program for Twitter. It offers social accountability by posting your daily tracker for the goal that you set.
I’m mostly traveling this month. It will be busy and I’ll have limited time for work. I’ll have to adapt my goals accordingly.
Health and happiness
- Sleep for 8 hours. Don’t wake up past 8am.
- Eat a daily serving of vegetables.
- Journal for 1 hour on flights.
- 1 hour of daily meditation (best effort during the weddings)
- Exercise 1x/week. Stretch every day.
- Post daily on Twitter.
- Reach out to 50 creators.
In addition, I won’t be publishing any new posts until the next retrospective. See you soon!
This post took redacted minutes to write.
P.S: You can find more of my thoughts on Twitter @_suketk.