What's in store for you:

1. Photo From My Life
2. Life Thought: Remembering the Good Times
3. Financial Thought: Concentrated Stock Positions
4. Good Sh*t: Playing Hooky as an Adult

Photo From My Life:

Life Thought:

Remembering the Good Times: Every year, my wife and I sit down and put together a photo album filled with the greatest hits from the past 12 months. It’s a simple habit, but one of my favorites. Life moves fast—too fast—and it’s easy to forget all the little (and big) moments that made a year special. Looking back at our albums, we get to relive the best trips, the best laughs, and the tiny everyday moments that made us smile.

It also creates a pretty cool physical memento. Over time, these albums will compound, building a tangible record of our life together—something we can flip through decades from now when memories start to fade and our kids don't believe that Dad went skydiving (sorry Mom!).

I can’t take credit for this idea—my business partner Ben and his wife have been doing it for years. As usual, he shared a great tip, and I’m glad we ran with it.

If you’re looking for an easy way to reflect and appreciate the good stuff, I highly recommend it. Plus, nothing beats the feeling of cracking open a book of memories instead of scrolling through a camera roll. I highly recommend using the Apple Photos app to make a book. It's super easy and can be done in a few hours.

Financial Thought:

Concentrated Stock Positions: If you’ve got a large chunk of your net worth tied up in your employer’s stock, it’s worth asking—is the upside really worth the risk?

Look, I get it. You believe in your company. Maybe you’ve been there for years, maybe you scored a sweet equity package, and maybe you’re convinced the stock is only going up. But here’s the problem: your salary and your biggest investment are riding on the exact same risk factor. If things go south, you’re not just watching your stock take a hit—you could also be out of a job.

Diversifying doesn't mean completely divesting your employer's stock. Instead, it's about ensuring that this position aligns with your overall financial goals and risk tolerance. Maintaining an outsized position can be beneficial, especially if you believe in the company's long-term prospects. However, it's essential that this holding doesn't overwhelm your portfolio.

I’m not saying you should dump all your shares and run. A balanced approach is key—you can still have an outsized position if you truly believe in your company, but it shouldn’t dominate your portfolio.

The trick is managing diversification while being smart about taxes, liquidity, and your long-term goals. There are a few ways of doing this and per usual, the right answer depends on the person and their specific goals.

1. Gradual Share Sales: Selling portions of your stock over time can help manage tax liabilities by spreading gains across multiple tax years. This approach also allows you to take advantage of favorable market conditions.
2. Exchange Funds: These allow you to pool your shares with other investors, effectively exchanging your concentrated position for a diversified portfolio without triggering immediate capital gains taxes. However, they often require a commitment of several years.
3. Tax-Loss Harvesting: Offset gains from selling your employer's stock by realizing losses in other investments. This strategy can reduce your overall tax burden.
4. Charitable Donations: Donating appreciated stock to charitable organizations (or a Donor Advised Fund) can provide a tax deduction while allowing you to avoid capital gains taxes.

At the end of the day, betting big on a single stock—especially the one that also pays your salary—isn’t a risk most people should take. Play it smart, hedge your bets, and make sure you’re not putting all your financial eggs in one (company-branded) basket.

Good Sh*t:

Playing Hooky as an Adult: Taking a random day off when everyone else is working might be the most underrated life hack out there. It’s the closest thing to playing hooky as an adult—except no one can actually get you in trouble.

I pulled this off on Presidents' Day. Technically a holiday, but my wife still had work, and my son was in daycare. The result? A full, obligation-free me day. No emails (okay, maybe a few). No meetings. No tiny human demanding snacks. Just pure, unfiltered freedom.

It felt like I had found a glitch in the system. I went out for a walk in the middle of the morning just because. Actually sat down for lunch instead of inhaling it over my keyboard. I even played 18 holes of golf. Amazingly, I only lost 3 balls too!

If you haven’t done this, I highly recommend it. Pick a random weekday, take the day off, and just exist while the rest of the world is busy. It’s a mini vacation without the travel hassle, PTO guilt, or a small fortune spent on flights. 10/10, will be doing it again.

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