Perspectives, Probabilities & Polemics
Introspection on effective communication
To state the obvious, not everyone sees everything the same way.
If you’ve followed me on Twitter or read my writing before on Substack or LinkedIn, you probably know that I cared intensely about the recent mayoral election in Chicago. Well, voters decided to go in a different direction than that which I had hoped. Mayor-elect Brandon Johnson prevailed in a narrow victory, yet a victory nonetheless. I’m disappointed in the outcome, but that’s how elections work. So altough I still have serious concerns about what this election result means for Chicago, a respectful congrats to the Mayor-elect and his supporters. We all should strive to get along at the end of the day, even when we may disagree on various issues.
While I could rehash some of my financial analysis on why I’m skeptical of Mayor-elect Johnson’s economic plans or further discuss my perspective on public safety, I’m not sure what good that would do at this point. There will come a time to try finding common ground, particularly on the business and public finance fronts. And frankly, there are figures of more notable stature than myself who are better positioned to advocate for the pro-growth views I hold. As stimulating economic activity here is - in my opinion - the most realistic way to make progress on our fiscal nightmare and generate more revenue to improve city services without overburdening taxpayers.
For now, though, I wanted to reflect on why the message that I (and others) put forward didn’t sufficiently resonate and offer up an idea on how to more persuasively communicate in the future. To do this thoughtfully and sincerely, I’m going to start with a personal detour of sorts. Please bear with me…
First, some background: No question about it, I have a lot to be thankful for. I was born into a supportive and loving family. My grandparents lived just blocks away and functioned as essentially a second set of parents. I made great friends in my childhood - my best friends to this day. Attended good schools. I have a career and job I like. A superstar wife. Kids I adore. A sweet (and neurotic) dog. A nice house in a nice neighborhood. Stuff is mostly good and I’m grateful for that.
While I had the advantage of a solid support group and friends who reinforced productive habits, I also worked my ass off at everything I did. I still do! And for the first 30-ish years of my life, that really paid off. If you want to tell me that I was born on first, fine - but I damn sure wanted to prove that I could round the bases on my own.
So from as early as I can recall, I was motivated and competitive about all the activities I took up - from school to sports. Competitive more so with myself than against anyone else. Sometimes that served me well (academically and professionally), and sometimes there have been downsides (impact on relationships and doing dumb stuff like tearing muscles overdoing weight lifts).
After high school, I moved a short drive down the road to study history at Northwestern. Thoroughly enjoyed college, but spent much of my time in the library (which I also enjoyed). Went to Harvard Law. Met my wife. Worked at one of the big Boston law firms for a few years. Loved living in Boston, but corporate law wasn’t for me. Transitioned to investing. Soon after, I was earning accolades at investment conferences and raised capital from renowned allocators for my own strategy.
Again, I’m fully appreciative of the fact that I started with key advantages and benefitted from some luck. But that personal arc would look a lot different had I not worked hard and put myself in a position to succeed when opportunities arose.
Then the humbling began around 2017. I guess it was bound to.
Up until my early 30s, the only truly bad thing that ever happened to me was almost dying of a tropical disease in Costa Rica in 2003. But after a few rough months I recovered, and I have always found the whole episode sort of funny because I got sick from bat urine. I mean, you kind of have to admit that’s amusing. Bat urine!
Anyways, when my wife and I moved from Boston to Chicago for my investing work, I promised her we could get a dog. We (more like she) decided on a Samoyed. An energetic breed known for being great with kids. We bought Hallie from a highly regarded breeder out East. Honestly, I wasn’t enthusiastic about getting her. In fact, a dog was the last thing I wanted. I was so immersed in my work that I didn’t know how I’d make time for taking care of one. But as soon as Hallie came home, we bonded. The old pictures break my heart.
A few months after getting Hallie, we noticed her front legs were growing misshaped. Severely misshaped. Walking became increasingly challenging for her. Something was wrong.
We consulted with top veterinary specialists in the Midwest. Ended up getting her examined by experts at Purdue University’s Veterinary Hospital - a three-hour drive from our home in Chicago. She had a rare condition: osteochondrodysplasia. A genetic disorder that caused her legs to grow abnormally. The poor girl couldn’t walk without excruciating pain.
We elected to have a complex procedure done at Purdue in the hope of giving Hallie a better, more comfortable life. It was actually so complex that the surgeons first reconstructed her legs with a 3D-printer to practice on the model. One leg healed perfectly. The other didn’t. I made bi-weekly trips to West Lafayette for two months to get her assessed by the doctors. Even took her to specialized dog rehab in Chicago.
Ultimately, we realized we couldn’t provide her the type of care and lifestyle she needed, and we were not willing to put her through the trauma of another high risk surgery. We found a family in Connecticut that volunteered to take care of her - they loved Samoyeds and lived in a quiet, rural area. It was the best outcome for everyone. Drove Hallie out there. Stayed overnight in Scranton. Dropped her off. Drove back without stopping. Totally shattered.
Then a few months later, the big hedge fund I worked with made a strategic pivot and redeemed all that money I had raised. So much for all the fancy meetings with all the fancy people at all the fancy places.
Soon after, we got a new Samoyed - and got to relive the fun of training a puppy again… At last, some genuinely good news. My wife became pregnant with our son. The good vibes lasted about a week.
My mother-in-law, who was struggling financially and barely getting by in a run-down condo in Evansville, Indiana, told us she was feeling ill. The diagnosis came back: cancer. Went down there to assist her. Discovered her finances were a mess, she owed lots of money to multiple creditors and the IRS had a lien on her home. Helped her take care of that. Got her financial life in some semblance of order and prepared her mentally for her course of treatment.
In the summer of 2019, our son was born. And then the cancer came back. Another surgery. More financial stress with medical bills. More time in Indiana and the University of Michigan’s hospital instead of enjoying time at home with our son. The tiredness and adjustment of being new parents while taking care of my mother-in-law. The emotional and physical drain for my wife. At last, some hope. A Christmas trip to see family in California.
A final last Christmas trip. The surgery didn’t work as intended. Seeing her helplessly suffer. My wife - as her primary caretaker - having to experience it up close. The cruel agony of my wife losing her only parent just as she became a new mother herself.
Her constant feeling of emptiness. Inconsolable nights. The impossibility of coping with the prospect of a life without your mother at such a young age. The loss of a loving grandparent.
Clearing out the delipidated condo in Evansville. Regretting her reluctance to live with us. The messy estate matters that took years for us to resolve despite the small size. The family fallout upon realizing the source of financial problems.
Then the world shuts down for Covid. Still work, but no childcare for months. The stress of that summer and fall’s crime spike, with our son coming much too close to gun violence on several instances in our quiet neighborhood. A health scare of my own with a liver issue (which I since resolved).
Jump ahead to the next summer. Just as everything was normalizing, one of my best friends died, alone, of an accidental overdose. I remember another friend calling me with the news. I was at the grocery store with a cart full of food. “What do you mean he’s dead?” Took me a few times to process. Broke down in the dairy section, abruptly left the cart in the aisle and sat motionless in my car until I gained enough composure to drive home. From texting him about mattress recommendations to literally shoveling dirt onto his coffin a week later. As his dad said to me at the funeral, with a solemn look of disbelief, “tough break.”
Ok, so where am I going with all this?…
Far worse things have happened to far less fortunate people. While that stretch from 2017-21 had some fantastic moments with our newborn son, it generally was not the most enjoyable. However, it toughened me up. Re-set my ability to deal with stress and uncertainty at a substantially higher level. Forced me to develop a deeper level of empathy. Made me realize that hard work isn’t everything. Life happens and the outcomes don’t always reflect your input. You can shape your trajectory - and I think you should try to - but you can’t always control it. And you certainly can’t control what happens around you, or to the people around you.
Look, I’m not trying to earn any sympathy points. I’m the last one who needs them. I’m sharing this because the experience of those several years gave me a more nuanced perspective on life from which I think I can better draw on when advocating policy ideas (or any ideas) to anyone who may not be predisposed to think alike. Which I have learned, at least when it comes to state and local matters, is a lot of people!
The internet - especially Twitter - is not the best place to persuade people to think differently. Still, in this last election cycle, I could have probably done better to the extent I tried. Even though I strongly stand behind everything I have written when it comes to Illinois and Chicago issues, there may have been a more effective and relatable way to get my message across.
Below is a graphic from the writer Tim Urban (known for the blog Wait But Why). It shows branches depicting the life paths open and closed to us. I think it’s a powerful and provocative visual - it suggests the future is full of possibility. As Urban wrote last year in a New York Times guest essay: “We think a lot about those black lines: the roads not taken, the opportunities missed, the ones that got away. But most of us greatly underestimate the size of the lush green tree of possibilities that lie ahead of us.”
To make a point, I’m going to modify this chart a bit with two red circles (see below). For the sake of argument, let’s stipulate that your goal, to date, has been reaching the upper right area of the chart (along the “Today” axis). Assume doing so improves the “lush green tree of possibilities” open to you in the future. Now, suppose you are born in the top red circle, with some degree of an advantage. Your path is a bit easier. Nothing is ensured, but you have a head start. Let’s now suppose you are born in the lower red circle with some opportunities foreclosed at the outset. Well, the upwards path is a lot harder.
I think that, as a society, we should aspire to give everyone a chance to reach adulthood in the median (green line) position - so that the future is open to whatever one can make of it. But we all know that’s not how it works. The average kid born into poverty or a broken home is less likely to have the same opportunities as the average kid born into comfort and stability. It’s a sad matter of probabilities.
My probabilities to start were good, and I actively made them better. For many, though - through no fault of their own - their probabilities are not as good and they may lack the experience, education, guidance, social networks, etc. to improve them. These disparities are not a healthy feature of America today. They certainly are not a healthy feature of life in Chicago.
I had a string of tough years. But there are many people out there who have had far tougher ones. Moreover, there are many who have had tougher ones during their formative years, which is a major impediment to their future growth and success. If you’re in an environment filled with stress and hardship, it’s inevitably going to impact your wellbeing and trajectory.
I think people can see some of our obvious societal disparities and want change - as well they should. And I think Brandon Johnson was successful in this election, in part, because he spoke poignantly to these disparities. While the language he used around these issues was unnecessarily inflammatory, he’s wasn’t wrong to point out some of the basic problems. And he found a receptive voting public. Particularly amongst younger voters who are generally sensitive to these issues and also have had a relatively tough go at it financially since the 2007-08 Financial Crisis.
I wrote about this general feeling of frustration (albeit from an investing angle) in a piece called Manifest Despondency last year. Basically, if you feel stuck in your position in life and can’t move up or away, you end up moving psychologically - and often to extreme places. The lack of both upwards and physical mobility in the US - once a defining feature of life in America - is a major problem with unhealthy social and political implications.
I’ve also commented on Twitter how I think younger working people are getting a raw deal - courtesy of the political class - for diverting so much of their income to support people in retirement while the public services they rely on deteriorate and their costs of living rise. Today’s average younger voter might be unaware of the origins of these problems (and how politicians ideologically aligned with Mr. Johnson have contributed to them), but they nevertheless feel them. So, I think we had a frustrated voting public here that was - at least on the margin - receptive to the radical change message Johnson was selling (even if they didn’t appreciate the risks and impracticality inherent in many of his policy initiatives).
My disagreements with the incoming mayor aren’t so much on his broader goals - of a better, more prosperous Chicago for everyone (particularly for those in communities that have historically struggled) - but on how you accomplish that. There, my disagreements are extreme, as I think many of his proposals just threaten to make all the problems he has diagnosed worse.
In laymen’s terms, it would be far better to grow the proverbial pie so that we all have more to eat, than to just propose new ways to slice it. If you want more details, you can go back and review some of my Twitter threads on topics ranging from his budget and economic plans, to tax plans, to our underlying pension problems and (more recently) to his views on public safety.
Now, let me be clear: I’m not a politician - nor am I interested in really becoming one any time soon. But I do care about the direction of our politics and many policy issues. So, to the extent I comment on things, I’d rather it be effective.
Where I failed (and other likeminded folks failed) was in thinking you could persuade others by analyzing how their ideas were flawed (even if conducting the analysis with reason and rigor). Probably Psychology 101 level stuff, but I’m guessing no one likes hearing that what they think is wrong. They are just going to tune out your polemics against their positions.
It seems obvious in retrospect, but if you’re looking to expand a voting coalition, you have to convince others that your ideas can help better achieve their goals. And that’s where I could have thoughtfully drawn on the several challenging years I had.
Having gone through a rough patch myself, I truly get that people are struggling out there. Speaking to that a bit more empathetically would perhaps have gone a longer way in making the case for the types of rational policies that I think would yield positive results.
My concern is that we are about to go through an experiment in extreme progressivism in Chicago, which I don’t think will yield the most positive results. As I’ve explained, my criticism of the modern progressive movement - of which Mayor-elect Johnson represents - isn’t so much its purported aims (especially not the historical ones seeking to expand civil liberties), but far more so the means by which it seeks to achieve them. Lacking pragmatism in the economics and public safety spheres, for instance, just risks harming the people that progressives seek to help through the implementation of ineffectual and often counterproductive policies. Hopefully I’m wrong.
Now, to be clear, if I think the approach we’re taking is flawed, I will definitely make my voice heard. But I’ll try to remember that the whole purpose of commenting on policy isn’t to score points in some echo chamber. It’s to actually shift the conversation and ultimately achieve constructive outcomes.
Everyone has what in his or her mind is a legitimate perspective. I happen to think my views lie a bit farther along the reality and data-based spectrum when it comes to a few issues, but that doesn’t mean others will see it that way. A lot of people out there probably think I’m a moron. And based on some of the Twitter comments, a lot worse!
Knowing that, there’s little downside in sometimes taking a more sensitive approach that recognizes people come to every issue with unique experiences and to try speaking better to the concerns and emotions of those on the other side. Please don’t get me wrong - I’m not changing my core views on anything right now. But I think the tactics have some room for improvement. Whether the goal is to get sound policy implemented or convince someone of an investing thesis, it can’t hurt to pair the heart a bit more with the head. We shall see…
Two last things:
If you want to know my general political philosophy, I put it all together in a piece at the beginning of 2022 called: American Tune.
To the extent I write more in the future here, it is likely to be a bit more financial markets oriented (plus some hiking and parenting stuff). I’m sure I’ll still comment on policy from time-to-time, but that’s not always going to be the main focus of the work I share.
Thanks for reading. This was long. Hopefully it was worth your time.
Stuart
I came to this through today's Wirepoints morning email link. Very good. Thanks for taking the time to write this. (As an aside, one of my concerns with Wirepoints is that they do not always practice what you are preaching here. I have relayed my concerns to Ted Dabrowski, although I don't think I was as articulate as you are in this piece. All that said, I think some of their tone is changing, and, as you write here, that will likely be for the good.)