Lessons from Hiking – 2019 Q3

Tom’s Quarterly Reads – Portolan Financial

Tom’s Quarterly Reads

Here are the best articles I read over the past three months, mostly all finance-related. I’ve moved to grouping the links by topic, but the topics will shift each quarter based on the set of articles. 

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Just Read This

The Financial Turing Test (Of Dollars and Data): This pieces attempts to propose a question that identifies financial charlatans, ultimately arriving at: “How do you get rich without getting lucky?” This Twitter thread attempts to answer.

Family and Personal Finance

How Dual-Career Couples Make It Work (HBR): Deep look at dual-career couples, where work is a primary source of identity for both partners. The author identifies three major transition points in couples’ work and personal lives where the psychological and social forces on them are strongest, and provides great insights on why some couples succeed and others fail at these junctures.

Don’t Get Hosed When Buying Financial Products and Services (Morningstar): Understand the difference between financial products and financial services. They’re regulated and marketed differently, and you should go about vetting them differently.

What Induces Children to Save (More)? (Alpha Architect): One of their numerous summaries of academic papers in the financial realm, this provides insights into what impacts kids’ decisions on saving vs consumption.

The Thing That’s Probably Blowing a Hole in Your Budget (A Wealth of Common Sense): Make sure your car purchase/lease decisions aren’t having an overly negative impact on your ability to save for retirement, education or any of your other goals.

Economics and Investing

Negative Bond Yields – A Twitter Thread (Twitter): Great thread that looks at negative interest rates, and provides much more nuance than one usually finds on Twitter.

Neither, and New: Lessons from Uber and Vision Fund (Stratechery): Uber and WeWork have characteristics of technology companies but also interface with large amounts of real-world assets and friction. As a result, we should be careful not to quickly bucket them as either tech companies, nor as analog incumbents.

REITs Aren’t a True Alternative (Morningstar): An interesting perspective that I don’t entirely agree with, but worth considering. Real Estate Investment Trusts (REITs) are often seen as an different asset class from other stocks, but the author defends his claim that REITs are “just stocks that look a little different.”

Boxed In at the Docks: How a Lifeline From China Changed Greece (Fortune): The port of Piraeus is a case study that illuminates the opportunities and challenges presented by China’s Belt and Road Initiative.


Face recognition and the ethics of AI (Benedict Evans): Today we have many of the same concerns with machine learning as we did when huge databases were first being built: “we worry what happens if it doesn’t work and we worry what happens if it does work.”

Universal Laws of the World (Collaborative Fund): If Morgan Housel writes it, it’s worth reading. Here’s the best of him this quarter: “a few laws – some scientific, some not – from specific fields that hold universal truths”.


Why we lie about being retired (BBC): “People think of planning for retirement as a financial exercise, and that’s all. It also needs to be a psychological and relationship exercise as well.”

As the Years Go By (Humble Dollar): Retirement broken down into 4 phases, with rough age brackets. Hand-in-hand with the roadmap, here is food for thought on estate planning as well as charitable giving.

Tom’s Thoughts

No deep financial insights this month, just some more general lessons I learned from hiking. So to start, just a reminder that there are only 3 months to the end of the year – starting thinking about tax implications of decisions you’ve made this year, and take some steps to make sure your tax return doesn’t have any surprises waiting come spring!

In early September, I had the chance to do some hiking along the Pacific Crest Trail (PCT) with a friend of mine. He is through-hiking the entire 2,650 miles from Canada to Mexico, and was kind enough to slow down and let me tag along for a section of Oregon. We met up just north of Crater Lake and hiked up to the rim of the lake for some amazing views and then continued on south, completing about 75 miles. I don’t have any deep investing thoughts from our 4 days of hiking, but I did have two things I wanted to share.

First, having everything that was on your list doesn’t mean you’re properly prepared. In preparation for my hike, I made a list of the gear, food and clothing I needed, and I ensured everything was in my pack when I got on the plane. The problem is that I focused too much on getting the stuff that was on my list, and not on making sure the list was complete. Not on the list: gloves, which would have been nice when it was 45 degrees, raining and windy. Also not on the list: a second warming layer, which I would have been in dire need of if the temperature had dropped another 10 degrees. While I did a lot of research and testing of my food options (dehydrated mashed potatoes, anyone?), I didn’t ask my buddy about what clothing he packed. If I had he would have mentioned both his gloves and his puffy vest, and they would have been added to the list. So remember: don’t give yourself a false sense of security just by making a list – you have to check it twice.

Second, it was amazing to disconnect for a few days – and not just in a my-phone-is-right-over-there-I’m-choosing-not-to-look type of way. Being literally unable to get a signal renders the phone useless, which was quite freeing. It was powerless to command my attention (also the cold killed the battery), and I have to admit that I somewhat relished the feeling. It was sad to not get new cute pictures of our 9-month-old Claire (see below) for a few days, but well worth it – I got to see them all when we got a signal again. It’s extremely difficult to fit into most people’s schedules – I count myself very lucky I was able to do it – but having an enforced period where one is disconnected is great. The important part – which I’m still working on – is capitalizing on the experience when you get back by identifying the useless distractions that we’ve allowed to build up in our daily routines. That isn’t to say that all of the non-productive things I do I my phone are going away (they aren’t), but rather identifying the things we check or get alerts about that used to be fun, but have now become habits or chores.

Claire does surprisingly well with air travel, and her smile makes her much more popular with people seated near us than we could have hoped.


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