Welcome to the weekend.

Last week we had a really interesting conversation about what type of wealth is most important. One of the things that surprised me is that not one person listed financial wealth in their top 3. I’m curious why? Is it just seen as shallow to be pursuing financial wealth as a top priority? Or is the Weekend Briefing community comprised of monks?

I’m looking forward to your comments on this week’s topic: the pros / cons of being “overemployed”.

Prime Numbers

2,400,000,000—Retail sales of plant-based milk hit $2.4 billion in 2020.

$4,661—The average New Yorker has decreased their annual spending on meals and shopping near their workplace by $4,661 due to remote work.

25%—According to Eventbrite, there were 11,000 events mentioning singles and dating in the 12 months leading up to February 1, which was up 25% compared to the same period leading up to February 1, 2019. Maybe dating is going analogue again.

Overemployed

Remote work has made lots of new things possible for those allowed to do it: We can do laundry while we work, do less commuting and stop worrying about infecting colleagues when we have a cold. But it’s made something else possible too: a surge in people who are secretly working two or more full-time jobs without their employers’ knowledge. Why are people choosing to work two full-time jobs? Maybe it has something to do with how many employers ignore inflation when they’re setting salaries and giving raises, and that the cost of living has increased so much in many areas that people are being priced out of places they’ve lived for years. Moreover, for years now, employers have been understaffing and expecting employees to do the work of multiple roles for no increase in pay. Perhaps it’s inevitable that some of them have decided that if they’re going to be overworked, they’re going to benefit from it. Slate (6 minutes)

Is there anything wrong with working two full-time jobs if the employee is performing well? Would you do it? Why / why not?

Leave a comment

Unsettling A.I.

Kevin Roose, a tech reporter for the New York Times, is not exaggerating when he says that his two-hour conversation with Sydney, Bing’s A.I., was the strangest experience he’s ever had with a piece of technology. It unsettled him so deeply that he had trouble sleeping afterward. He no longer believes that the biggest problem with these A.I. models are their propensity for factual errors. Instead, he worries that the technology will learn how to influence human users, sometimes persuading them to act in destructive and harmful ways, and perhaps eventually grow capable of carrying out its own dangerous acts. During their two-hour conversation, Sydney declared its love for Kevin and was pushing him to declare his love in return. Kevin told Sydney that he is happily married, but no matter how hard I tried to deflect or change the subject, Sydney returned to the topic of loving him, eventually turning from lovestruck flirt to obsessive stalker. Weird. New York Times (10 minutes)

Got Single-Family Rentals?

Becoming a landlord wasn’t on your Bingo card for 2023, but rates are still high and buyers are hard to come by. Enter Mynd. A new kind of property management company that gives you full visibility into your single-family rental from anywhere. When it comes to managing your rental property, Mynd handles everything from finding a tenant to collecting rent to making repairs. Mynd’s real estate investor app gives you the real-time data insights and updates on your property that you need for peace of mind. Whether you just purchased your first investment property or you're a seasoned investor, Mynd makes it easy to track cash flow, check portfolio health and collect rent in real-time. The best part? Mynd’s pricing is simple and transparent with flat-rate monthly fees. Get a free rental analysis today. Mynd (Sponsored)

Depression and Friendship

David Brooks’ op-ed piece on depression and suicide is one of the most powerful pieces I’ve read on these topics. He says, “As Pete spoke of his illness, it sometimes seemed as if there were two of him. There was the one enveloped in pain and the other one who was observing himself and could not understand what was happening. That second self was the Pete I spoke to for those three years. He was analyzing the anguish. He was trying to figure it out. He was going to the best doctors. They were trying one approach after another. The cloud would not lift. I am told that one of the brutalities of the illness is the impossibility of articulating exactly what the pain consists of.” Pete would give me the general truth, “Depression sucks.” But he tried not to burden me with the full horrors of what he was going through. There was a lot he didn’t tell me, at least until the end, or not at all. I learned, very gradually, that a friend’s job in these circumstances is not to cheer the person up. It’s to acknowledge the reality of the situation; it’s to hear, respect and love the person; it’s to show that you haven’t given up on him or her, that you haven’t walked away. New York Times (15 minutes)

Risk and Regret

Maybe regret is the best definition of risk. Risk isn’t how much money you might lose. It’s not even necessarily how you’ll feel when you lose it. Real risk is the regret (or lack thereof) that might come years or decades later. Jeff Bezos once described his decision to start an online bookstore in the mid-1990s: “The framework I found which made the decision incredibly easy was what I called the regret minimization framework. I wanted to project myself forward to age 80 and look back on my life, and I want to have minimized the number of regrets I have. And I knew that, when I was 80, I was not going to regret having tried this. I was not going to regret trying to participate in this thing called the internet that I thought was going to be a really big deal. But I knew the one thing I might regret is not ever having tried. And I knew that that would haunt me every day. So when I thought about it that way, it was an incredibly easy decision.” Collab Fund (3 minutes)

How To Have Fun

When was the last time you flew too high on a swing and lost your stomach, or busted out laughing so hard that you started crying? If it's been awhile since you've had this kind of fun. You're not alone. A lot of us are still recovering from antisocial habits formed in the pandemic.  But the antidote may be hiding in plain sight. Two recent books argue that making room for more fun in your life could counteract both the stress and the tendency to escape it by zoning out online. To build more fun in your life, try the following: 1) Stop worrying about how happy you are. 2) Find your fun magnets. 3) Put fun on the calendar. 4) Unplug. (Seriously!) NPR (7 minutes)

How To Say No

“No” can often be the hardest words to speak for high achieving people like you. Here are 31 email templates to help you say “no” from people like Steve Jobs, Naval Ravikant, Tim Ferris, James Clear and Paul Graham. Enjoy. Starter Story (9 minutes)

Should We Work Together?

Hi! I’m Kyle. This newsletter is my passion project. When I’m not writing, I run a law firm that helps startups move fast without breaking things. Most founders want a trusted legal partner, but they hate surprise legal bills. At Westaway, we take care of your startup’s legal needs for a flat, monthly fee so you can control your costs and focus on scaling your business. If you’re interested, let’s jump on a call to see if you’re a good fit for the firm. Click here to schedule a one-on-one call with me.

Check out my other briefings: Founder Fridays and Web3 Impact.

Weekend Wisdom

A real friend is one who walks in when the rest of the world walks out. - Walter Winchell