Kill Your Darlings

Deliberate Discourse is coming to an end.

This is the last newsletter of Deliberate Discourse.

It was a fun, beautiful experiment that gained a wide readership but it’s time to close the door for other opportunities to open.

I’ve been blogging in some form or another since August 2017. In the beginning, I would publish four to five times a week. For the past year, I more or less posted once a week. I wanted to show up and prove that my writing was worth reading. Over the past two years, I made good money, met a bunch of new people, and became a better writer.

In the last few months, however, I’ve became less enthusiastic about writing. It’s started to feel more like a chore than a privilege.

Since 2017, more people are getting onboard this online writing thing (which is good), but everyone’s starting to regurgitate the same thing (which is bad). Charlatans have moved into the content creation business, and it’s hard to feel good contributing to the space.

The digital economy has removed the traditional barriers in the publishing industry but just because new platforms exist doesn’t mean we all need to use them and leverage ourselves to death.

I don’t want to be some self-help guru. I have no plans to make dispensing unsolicited life advice my full-time gig. I’m a lawyer who dabbles in writing. I’m not a writer who dabbles in law.

Leaving money on the table is okay. Keeping thoughts to yourself is okay. Refusing to participate in virtue signalling is okay. And, most important of all, ruthlessly eliminating things that no longer serve you is okay.

Greg McKeown said it best when he explained:

“Essentialists see trade-offs as an inherent part of life, not as an inherently negative part of life. Instead of asking, “What do I have to give up?” they ask, “What do I want to go big on?”

Right now that’s not Deliberate Discourse. It’s time to go big on family, career, community, and boredom. I’m finally taking my own medicine and disassembling my constant state of busyness. It’s time to make room for less.

This doesn’t mean I’ll never write again. I’m still on Medium, where I intend to post every so often — probably once or twice a month. And for daily musings, you can always follow me on Twitter.

Now with all that said, it’s time that the curtains close.

Thank you for your support. It’s been a privilege to share ideas with you.



Designing a Minimalist Economy With Alternative Ownership Structures

Over the long weekend, I read a fascinating book by Marjorie Kelly titled, “Owning Our Future: The Emerging Ownership Revolution.” 

The central thesis of the book is that more and more people are experimenting with alternative forms of ownership aimed at creating prosperity for generations to come. Kelly travels across the world to learn from those who have prioritized profit sharing, collective ownership, and sustainable environmental practices. 

The book is worth reading in its entirety but I thought I would share some of the case studies that were mentioned.

Resident-Owned Communities

In 1983, the term“resident-owned community” began to spark, with its origins in New Hampshire. It began when a group of residents of the Meredith Center Trailer Park faced eviction from an out-of-town developer who wanted to purchase the land.

Instead of admitting defeat, the residents of the park obtained a loan from the New Hampshire Community Loan Fund and bought the park outright.

Kelly remarks:

That stroke of ingenuity, or grace, or whatever it was, grew into the loan fund’s Manufactured Housing Park Program, which uses a cooperative ownership model to help people in mobile homes and other kinds of manufactured houses purchase the land on which their homes stand. The process works a legal transformation in the nature of their property. Manufactured homes previously viewed by banks as personal property(inthe same category as a car or a boat) become real estate. That means they get better loan terms. It also means, as studies show, that residents plant more flowers, attend more school conferences, enjoy higher property values, and move less often. By owning the land where they live, a community of low-income people becomes a communion of subjects, their homes no longer a collection of objects viewed by an absentee landlord as a way to extract maximum rent.


It’s intriguing to me that the resident-owned community model was devised by a financial institution. It wasn’t a big bank with executives striving to make multimillions for themselves. Yet this loan fund has nearly $70 million under management. And it pays investors up to 4 and 5 percent interest annually, at a time when bank certificates of deposit are paying a fraction of that.

Community Development Corporations

Later in the book, Kelly recounts her experience with Keith Bisson, owner of Coastal Expertises Inc., a community development corporation based in Maine.

Through Costal Expertises Inc., five lobster fishermen were able to obtain a loan of $380,000 in order to setup the North End Lobster Co-op. Since its inception, the co-op has expanded to 24 lobster fishermen as members and supports more than 40 families, and each member earns roughly $30,000 - $50,000 per year.

Prior to the co-op, individual lobster fishermen would often fish on the town wharf and buy their own bait and fuel, forcing them to pay premium costs from wholesalers. In Maine, only 25 miles of the 5,300 miles of shoreline are delegated to fishing and marine industries.

Now as a result of joining the co-op, the fishermen have guaranteed access to water (the co-op put a working waterfront easement on the property), a place to store their traps and boats, and buy bait collectively at better prices.

The co-op has also arranged for a lobster buyer to regularly visit the co-op so that lobsters can be efficiently moved.

For lobster fishermen, this is a big deal.

This is all part in thanks to Costal Enterprises Inc., which has a unique mission: to create local ownership and local wealth by investing in rural, environmentally sustainable enterprises. Its primary industry, as the name implies, is fishing.

At the time Owning Our Future was written, Coastal Enterprises managed roughly $700 million dollars.

The Dairy Cooperative

The last example I’ll mention here is Organic Valley, an organic food brand and independent cooperative of organic farmers based in Wisconsin.

It is the nation’s largest farmer-owned organic co-op that generates more than $700 million in revenue per year. It is owned by approximately 1,700 organic family farms. For its organic milk, the company pays a price that is traditionally 60% higher than the commodity price farmers receive for non-organic milk.

When Kelly met with the CEO, George Siemon, she asked him about the economics of Organic Valley, who explained:

We’re not trying to maximize share price but maximize mission… Most CEOs wake up in the morning and look at their stock value and sweat bullets about how to raise it. When you take away that whole aspect, you now have a clearer focus… We don’t have any need for profits much over 2 percent. We’d just pay taxes on it. We’d rather give it to the farmers.

A Key Ingredient to a Minimalist Economy?

Kelly provides compelling alternatives to the traditional, profit-hungry companies, which I think can be useful when we contemplate what a minimalist economy might look like.

A minimalist economy is not, on its face, anti-growth but rather disputes that singularly focusing on growth is sustainable.

Ending growth does not mean shuttering all economic activity but rather producing and consuming less than our current rates.

From what I gather from Kelly, organizations that incorporate some form of collective ownership value sustainability (in terms of profits, stakeholder well-being, and environmental impact) over short-term gains.

Simple Recommendations

Forgive the law nerd in me but these recommendations are exclusively law-entered.

A powerful op-ed from a criminal defence lawyer who shamelessly explains that sometimes her clients need her more than her children. My interpretation of this piece is that work-life balance is irrelevant when it comes to certain high-stakes careers. I am inclined to agree.

A high-quality podcast from ACLU that interviews various ACLU lawyers and other progressive legal professionals on the biggest civil rights issues of the day.

A short documentary on Netflix that follows three women (a judge in Drug Court, a fire chief, and a street missionary) battling West Virginia’s opioid crisis. It specifically focuses on Huntington, West Virginia, where the overdose rate is 10x the national average. I was particularly taken with the judge’s story and how she approaches the cases that come before her.

Administrative Note: Due to an abundance of professional commitments this summer, Deliberate Discourse will temporarily move to a bi-monthly newsletter (twice a month).

See you on July 16th.

Your Inevitable Professional Decline

I bet you’ve thought about the progression of your career but have you ever thought about its decline?

In the July 2019 issue of The Atlantic, Arthur Brooks, President of the American Enterprise Institute, writes openly about his decision to retire. It becomes an acknowledgement of his inevitable professional decline.

Brooks writes:

In some professions, early decline is inescapable. No one expects an Olympic athlete to remain competitive until age 60. But in many physically non-demanding occupations, we implicitly reject the inevitability of decline before very old age. Sure, our quads and hamstrings may weaken a little as we age. But as long as we retain our marbles, our quality of work as a writer, lawyer, executive, or entrepreneur should remain high up to the very end, right? Many people think so. I recently met a man a bit older than I am who told me he planned to “push it until the wheels came off.” In effect, he planned to stay at the very top of his game by any means necessary, and then keel over.

But the research paints a different story.

Dean Simonton, a professor emeritus of psychology at UC Davis and lead expert on the trajectories of creative careers, argues that success and productivity increase within the first 20 years of a career, on average. In other words, if you start a career at age 30, “expect to do your best work around 50 and go into decline soon after that.”

The decline varies, obviously, by industry.

Brooks notes that entrepreneurs peak and decline earlier, on average. Many tech entrepreneurs are in creative decline by age 30. According to a 2014 report by the Harvard Business Review, founders of enterprises valued at $1 billion or more clustered in the 20 - 30 age range.

In the MLB, the best-performing home-plate umpires have 18 years less experience and, on average, are 23 years younger than the worst-performing umpires. As a result, the mandatory retirement age for umpires are 56!

Brooks writes:

In sum, if your profession requires mental processing speed or significant analytic capabilities—the kind of profession most college graduates occupy—noticeable decline is probably going to set in earlier than you imagine.


The biggest mistake professionally successful people make is attempting to sustain peak accomplishment indefinitely, trying to make use of the kind of fluid intelligence that begins fading relatively early in life. This is impossible. The key is to enjoy accomplishments for what they are in the moment, and to walk away perhaps before I am completely ready—but on my own terms.

I am pleased to see that this confirms the theory of deliberate practice, which debunks conventional wisdom that experience and results are linear.

This is often what’s touted in the legal profession, which is why senior lawyers are more expensive than junior lawyers. But if more experience created greater results then how do we explain that information workers get worse with age, not better? [1]

There will come a time where, as a lawyer, my advocacy skills will peak and, subsequently, decline. I can only hope I’ll be as candid and self-aware as Brooks and gracefully get out of the way.

See you next Tuesday.


[1] Note: Peak by K. Anders Ericsson. [Ericsson notes that surgeons who are recent graduates consistently outperform experienced surgeons. Why? Because younger surgeons have not yet developed bad habits, are informed of the latest research, and are hungry to improve].

Embracing Volalitility

A few thoughts on emotional positioning.

It recently struck me that minimalism shields us from chaos.

What I mean by that is when you only possess a few possessions and maintain a lifestyle well below your means, you have a tremendous advantage to not only survive but thrive when unexpected events inevitably disrupt your life. Nassim Taleb identifies these events as “Black Swans,” and argues that antifragility is the antidote to such events. I believe that minimalist living is an antifragile lifestyle.

Living with less protects you from a variety of threats.

The most dangerous is lifestyle inflation. That you refuse to needlessly consume as a cure for boredom or status signalling, you (hopefully) leave more money in the bank for sudden emergencies.

Another threat is job loss. Given that you have separated personal satisfaction from your personal belongings, your standard of living will likely be less affected.  

As Taleb correctly identifies, this relates to the philosophy of Stoicism. Seneca the Younger, perhaps the most famous individual associated with the philosophy, made it his lifelong mission to domesticate his emotions. Taleb writes:

Seneca’s practical method to counter such fragility was to go through mental exercises to write off possessions, so when losses occurred he would not feel the sting – a way to wrest one’s freedom from circumstances. It is similar to buying an insurance contract against losses. For instance, Seneca often started his journeys with almost the same belongings he would have if he were shipwrecked, which included a blanket to sleep on the ground, as inns were sparse at the time.

And continues:

To show how eminently modern this is, I will next reveal how I’ve applied this brand of Stoicism to wrest back psychological control of the randomness of life. I have always hated employment and the associated dependence on someone else’s arbitrary opinion, particularly when much of what’s done inside large corporations violates my sense of ethics. So I have, accordingly, except for eight years, been self-employed. But, before that, for my last job, I wrote my resignation letter before starting the new position, locked it up in a drawer, and felt free while I was there. Likewise, when I was a trader, a profession rife with a high dose of randomness, with continuous psychological harm that drills deep into one’s soul, I would go through the mental exercise of assuming every morning that the worst possible thing had actually happened – the rest of the day would be a bonus.


An intelligent life is all about such emotional positioning to eliminate the sting of harm, which as we saw is done by mentally writing off belongings so one does not feel any pain from losses. The volatility of the world no longer affects you negatively.

Part of the upside of minimalist living is that you often gain more free time since you are not online shopping, dispensing cognitive energy figuring out what to wear, and cleaning around all the clutter in your home.

I have used this extra time to diversify my income, making sure I’m not contingent on one sole employer. Instead of a single person or business who pays me, there are several hundred readers who pay me a little each month for my writing, as well as a few high-paying freelance clients every so often who pay a lot.

But the extra time should not simply be used to make more money. It is also to reconnect with the relationships in your life, including the one you have with yourself, which serve as a useful reminder to be grateful with what you have.

When volatility strikes, and it will, it is important to approach it with, at least, indifference and, at most, with enthusiasm.

You will notice that proactively living with less stuff will help you achieve that.


Over the last two weeks, I intentionally stopped drinking from the information firehose and allowed myself to stop listening to podcasts, reading the usual op-eds, and so forth. As such, I do not have recommendations for you other than to enjoy the good weather and take time to unwind with family and friends.

See you next Tuesday.

A Short Vacation

Hi everyone,

Deliberate Discourse will be on a brief vacation until June 18, 2019, where we’ll return to our regularly scheduled programming.

Reasons include:

  • A complex hearing scheduled tomorrow;

  • My birthday this week;

  • The Toronto Raptors are in the NBA finals.

I hope you enjoy the first half of June and we’ll speak in a few weeks.


Loading more posts…