Choosing optionality over arbitrary goals
Why I'm choosing to stop writing this newsletter on such a frequent basis
Once you make up your mind, things move quickly.
This is my 46th consecutive week writing and publishing a newsletter (which has essentially been one 1,500+ word essay each week for 45 weeks.
A few weeks ago, I noticed I was coming up on one full year of writing this newsletter. At the same time, I started to feel like writing a post every week was beginning to cost me more than it was giving me in return. In short, the ROI of this newsletter had declined.
I decided that after I hit the one year mark, I would put my pen down for a bit and re-evaluate. I would potentially stop writing the weekly newsletter and instead figure out how to turn the concepts I’ve articulated in this newsletter into a book or another medium that was longer-form and higher fidelity.
All I needed to do was get from 45 straight posts to 52 – just 7 more posts.
But once you make your mind up like that, it’s hard to keep going. The decision disrupts the fragile creative cycle of coming up something to write about, getting excited enough about the topic to crank out a few hours of writing, and hitting publish. As I started going through my familiar weekly cycle of starting to think about ideas to write about, I felt much less inspired than I had been for 45 straight weeks.
So rather than trying to push a boulder up a hill for another 7 weeks just so that I can hit the arbitrary milestone of writing weekly newsletter for a year straight, I’m going to just make the decision now. I’m going to stop publishing these newsletters on a weekly basis, and I will instead write in a less frequent monthly-ish cadence – publishing higher-fidelity posts when I feel inclined to do so.
I’m choosing to reclaim some freedom and optionality in lieu of hitting the arbitrary goal of 52 straight weeks of essays.
It’s fitting that this decision comes as a result of my own decision-making framework I wrote about last week.
When managing a portfolio of projects (including your day job), there are five decisions you can make decisions on how to invest your time, which can optimize for your overall momentum.
Invest more time: do this when a project is currently ROI-positive and an increase in effort will lead to growing ROI.
Invest time in experimentation: do this when a project is ROI-positive but an increase in effort will only result in predictable-yet-not-growing returns, you have hypotheses about changes that could increase the ROI, and you have the bandwidth to experiment.
Put on autopilot: do this when a project ROI-positive but an increase in effort will result in predictable-yet-not-growing returns and you either don’t have hypotheses yet about changes which will increase the ROI or you do not have the bandwidth to experiment with hypothesized changes.
Pivot: do this when a project isn’t ROI positive, but you have hypotheses around changes which may make it ROI-positive and the bandwidth to experiment with a pivot.
Kill: do this when a venture isn’t ROI positive, and you either do not have hypotheses around changes which might or you do not have the bandwidth to experiment with a pivot.
With the amount of investment currently required, my writing is no longer ROI-positive for me, and I don’t have positive momentum. With my current investment level, that leaves me with two options: pivot the newsletter or kill it. I didn’t like either of those options (I don’t have strong hypotheses of changes to make nor do I want to kill it), so my decision is to reduce the investment required by changing frequency of my writing commitment. This makes my writing ROI-positive again, while giving me more bandwidth and optionality to experiment with my writing formats – which may include converting my posts to date into a book at some point, or maybe something else that I’m not yet expecting.
You’ll hear from me again before too long (just not next Sunday). In the meantime, I’ll leave you with what I think are my best posts from the past 45 weeks:
Creating personal flywheels to grow entrepreneurial assets: Finding harmony between passions, side hustles, and day jobs to accelerate your career as an entrepreneur
Using Intellectual honesty to maximize the value you get from your asks: How being truth-seeking about the value you will provide to others will help you calibrate your asks
Everyone is an investor: Everyone with an entrepreneurial career – from investors, to founders, to startup employees – are investors. We can learn a lot from investors on building entrepreneurial careers.
Making progress on ventures before even starting: How entrepreneurs can de-risk ventures years before starting them
Maximizing entrepreneurial progress by systematically de-risking: Why focusing on traditional KPIs can be misleading and why it's better to focus on constantly de-risking
Three Rules of Entrepreneurial Diversification: When and when not to diversify time into side projects
Side projects as a lever for professional growth: and why employers should embrace side projects
Don’t look for co-founders; make friends: How to go about finding co-founders months or years before starting a company
7 aspiring founder personas: A framework for getting ready to start a company
Cultivating superpowers to maximize career trajectory: What watching Andrew Yang's ascent has taught me about cultivating superpowers
You're moving on from your startup. Now what?: A framework for navigating to the next chapter of your career after moving on from your startup, with reflections from my own experience
Nobody cares about what you're building: A dumb-simple mental model for being more efficient in building things
Building a portable audience: Why and how we can build portable audiences through our current gigs which we can take with us for future endeavors
Creating artifacts that accelerate your career: How entrepreneurs crystallize their experiences and insights into domain expertise
Assessing and acquiring the credentials to accelerate careers: Being intentional about acquiring credentials that will help with future endeavors
Persuasiveness as a skill: Being persuasive is a skill that enables entrepreneurs to be good at the many hats they wear; here's how persuasiveness breaks down and how it can be fortified
Why resourcefulness is the most important skill for entrepreneurs: And how like any skill, it can be learned
Resilience as an entrepreneurial skill: How resilience – which is better than persistence – can be worked on.