Jack's January 2024 Recap

Life updates, good books, good articles, and more.

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I’m doing something a bit different today.

For the last two years, I’ve been sharing links to different articles and podcasts at the bottom of my blog posts in my “Jack’s Picks” section, but I wanted more room and flexibility to share books and other miscellaneous content. I also wanted some space to provide general life/business updates, plus any other content that just doesn’t really fit within the context of any individual blog post.

Let’s get started!

General Update

After spending the last two and a half years on the “jobs suck, do your own thing” train, I’ve come around to the idea that, actually, a stable income isn’t necessarily a bad thing. Social media influencers tend to glorify the “be your own boss” lifestyle, but social media is also filled with grifters and charlatans (if an “entrepreneur’s” primary business is teaching you how to build your own business, it’s a pyramid scheme), and even those who do manage to profitably do their own thing are in the minority. Survivorship bias is alive and well. I have been fortunate to support myself as a freelancer both living abroad and attending business school in NYC over the last three years, but I’ve also realized that the freelancing lifestyles isn’t all sunshine and rainbows. Let me tell you a few things that suck about being a freelancer:

1) Health Insurance. Something I didn’t think much in 2021 when I threw caution to the wind and embarked on my backpacking trip around the world was that at 24, I could go back on my dad’s health insurance, but once I turned 26 I would have to figure that out on my own. Navigating health insurance on your own is annoying and frustrating and you’re constantly worrying if you are going to accidentally be charged $427 for a checkup because you have a runny nose. Not great!

2) Taxes. Unlike salaried jobs, where your taxes are automatically deducted, you have to pay your own taxes when you’re self-employed. When the money never actually makes it to your checking account it doesn’t feel like you’re losing much. When you have to physically make that payment yourself, it hurts. And if you don’t take care to set aside enough money over the course of the year, you could put yourself in a bad spot.

3) Instability. The freedom of freelancing comes with a cost: it’s on you to earn every dollar every month. You have to do the work and send the invoices. If someone’s late paying you, that sucks. Deal with it. Have a lead fall through? Oh well. Sponsor is annoyed about an underperforming ad? Deal with that too. Not having a boss also means not having a paycheck, and instability can wear on you after a while. As a 24-year-old living in $20-per-night hostels, instability is exciting. You feed off of it. As an almost-27-year-old living in a HCOL city, instability is a gateway drug for increased cortisol levels.

4) Pedigree. I have benefited from being “guy who blogs and writes a newsletter while attending an M7 business school” vs being “guy who blogs and writes a newsletter from Spain/Argentina/wherever.” Pedigree matters, and all of us, myself included, silently judge people by it. It’s why VCs swoon when they hear about a “Stanford dropout,” but couldn’t care less about the scrappy entrepreneur who never went to school in the first place. With graduation coming up in a few months, I’ve thought more about pedigree in my post-MBA life.

Two years ago, I would have turned my nose up at anything that remotely resembled a “job.” Now? I still wouldn’t pursue anything that conflicted with my interests and values, but I’ve been thinking more about what my future career might look like.

Enough of that, onto the books and other fun stuff.

Books I Liked

1) No Worries by Jared Dillian

I’ll be the first to say that most personal finance books are a drag, but No Worries by Jared Dillian was a surprisingly refreshing book that provided sensible personal finance advice.

This book wasn’t quantitative drudgery that discusses the most efficient retirement allocation, and it certainly wasn’t promotional FIRE material that compels the reader to postpone all enjoyment to some future date in one’s life. No Worries felt like sitting down with a trusted boss, football coach, professor or some other mentor and having a real discussion about money. Dillian gave cautionary tales about taking on bad debt, discussed the truth about finding a career path that will maximize your income, and provided anecdotes about how financial risk creates stress that impairs other facets of your life.

I’m not going to recommend many personal finance books, but No Worries is great. Check it out on Amazon.

2) Trust Me, I’m Lying by Ryan Holiday

Ryan Holiday was my inspiration for this list, and one of his first books, Trust Me, I’m Lying, is a fascinating exposé of the media industry. Before becoming a best-selling author, Holiday spent years working as a PR and marketing Swiss Army Knife, and he learned every trick in the book for generating attention.

In his book, Holiday explains how the internet’s near-instantaneous feedback loops have created a system where journalists need information in real time, all the time, and much of what we see on The Wall Street Journal and The New York Times begins in niche blogs and random corners of sites such as Twitter and Reddit. Holiday brought the sloppiness of modern journalism to light, showing how misinformation campaigns can explode online as speed has become the most important metric. Check it out on Amazon.

3) Fooled by Randomness by Nassim Taleb

I’ve been following Taleb on Twitter for years, and I’ve probably read a dozen of his essays, but somehow, I never opened any of his books until recently. And I loved this one.

After a career spent as an options trader who specialized in low-probability events that drove massive outcomes, Taleb turned to writing, and his snark and disdain toward many in the investing industry drips from every word in Fooled by Randomness.

And the book is excellent because of it.

Fooled by Randomness, to me, is an illustration of how folks who confuse the roles that luck and skill played in their fortuitous outcomes can quickly lose everything for the same reasons that they made it. It’s a fascinating case study on hidden risks, and Taleb’s air of superiority only made the language better. Check it out on Amazon.

Other Content

  • Corry Wang, a former tech equity researcher at Bernstein Research, published an interesting thread looking back at Nathan Myhrvold’s internal Microsoft memo, “Road Kill on the Information Highway,” from 1993. Many of Nathan’s predictions from 31 years ago proved to be shockingly accurate.

  • Gergely Orosz, the writer behind Pragmatic Engineer, wrote an excellent article on what the end of 0% interest rates means for tech startups and the broader tech industry. I have previously written a satirical piece on the same topic, but Gergely’s article is an excellent resource for anyone curious.

  • Adam Geringer published an interesting tweet (I’m assuming we still call them “tweets” ) on his decision to move from machine learning to geomatics and surveying. His reasoning was that there is an increasing waste of intellectual talent in fields like AI and tech, and skilled workers can make a much bigger impact by applying their talents to other overlooked industries that are traditionally seen as more “blue collar.” I hadn’t thought about this shift before, but it will be interesting to watch if Silicon Valley tech talent begins exploring other areas.

  • Derek Guy, the man behind Twitter’s most prolific work wear-focused account, wrote a great article about how and why you should find a good tailor. Fashion, especially men’s fashion, feels like it’s fading into obscurity as “smart casual” becomes the norm, but suits are cool, and everyone secretly wants to dress well. Derek is one of the few online voices still focused on men’s fashion.

  • Chris Arnade, who writes an excellent travel blog covering his journey walking around different cities around the world, wrote good article on the issue with American cities, in which he discusses the filth and poor infrastructure that exists here that otherwise poorer countries have managed to solve. (Chris also has an interesting life story in general.)


  • I’ve been using italki for more than a year now, and I think it’s the most valuable foreign language acquisition tool on the web. Basically, italki is a platform where you can find foreign language instructors from dozens of countries who speak dozens of languages. After chatting with a few different Spanish instructors, I’ve been meeting regularly with one Colombian woman for the last year+. Unlike in person lessons, which can cost upward of $50 per hour, I typically pay $8 per session (shout out to the US dollar, I guess). You can check out italki here.

  • Last year was my first year generating a meaningful income as a self-employed individual, and tax season was a nightmare as all revenues and expenses went through my personal bank accounts and credit cards. I set up a business account on Mercury for my one-person LLC in January, and it made separating my finances a million times easier. If you have a small business or run a one-person shop, Mercury is an excellent banking solution with the friendliest UI that I’ve seen. Check it out here.

As always, thanks for reading! If you want to send any interesting content my way, please drop the link(s) here.

- Jack

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