_{Exploring regret minimization, the value of a good advisor, and the cost of social media}

Happy Thursday! Thanks for reading Intentional Dollar — where we look at old money ideas through a new perspective.

What’s inside?

• One idea to experiment with

• Two quotes from others

• Three questions to dig deeper

• Four lines of poetry for the point

Disclaimer: This is not investment advice. These weekly posts represent my simple thoughts, a few quotes, and some questions — for educational purposes only.

_{One idea to experiment with:}

Regret Minimization

Jeff Bezos started Amazon after working through what he called a regret minimization framework.

He projected himself to age 80 and looked back on his hypothetical life with one goal in mind: to minimize the number of regrets he’d carry. In the context of starting Amazon, he knew that, at 80 years old, he wouldn’t regret having tried to build something on the internet—something he had deep conviction in.

He then carried forward the potential failure: if Amazon didn’t work out, if he left a high-paying job and it all collapsed, he could live with that. That wouldn’t be a long-standing sore spot of regret. But not trying, not following that conviction, as he put it, “would haunt me every day.”

Bezos recognized how short-term confusions—like the comfort of a steady job or the allure of an annual bonus—cloud long-term judgment. But from the vantage point of age 80, those distractions faded into irrelevance. The murky present came into sharp focus.

It’s an elegant approach. Simple, wildly effective—and it offers a kind of short feedback loop. A future self, whispering guidance into today’s decision.

But regret is a double-edged sword.

As easily as we might regret the paths not taken, we can also regret the ones we did. Regret doesn’t discriminate. Choosing poorly can leave us just as haunted as never choosing at all.

If we repeatedly neglect the future for short-term pleasure, we might one day regret that lack of foresight. Or we might reach age 80 sitting atop a pot of gold—but with poor health, shallow friendships, and broken family ties.

Regret wears many faces:

• Regret that you worked too much

• Regret that you saved too little—or too much

• Regret that you missed out on family trips

• Regret that you didn’t write down the details of daily life, now lost to time

• Regret that you didn’t care for your body while you were young

• Regret that you didn’t take that job—or start that business

We can’t walk through life without regret. But we can construct a kind of mental time machine—step into the shoes of our future self, and ask: What will I wish I had done? What would I go back and change?

That answer might not be perfect, but it gives our present choices texture, clarity, and meaning. It helps us live a life that, in the end, we’re proud to have lived.

_{Two quotes on the value of a good advisor:}

A good advisor’s job is not to beat the market. Good advisors do two things: 1) Help you craft and manage the plan to get you where you want to be. 2) Help you avoid catastrophic money mistakes. The latter is not done through coercion, but positive reinforcement, education, and thoughtful discourse.

_{Three questions on the cost of social media:}

1. How often do I purchase things because I’ve been influenced on social media?

2. What percentage of these purchases end up adding meaningful value to my life?

3. What percentage of the purchases come from trusted friends vs sponsored influencers?

Which question stuck with you? Questions like these are spotlights for the mind. Reply to this email and let me know which one shined light on a previously dark cave.

_{Four lines of poetry for the point:}

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Content ideas, questions? Reply to this email or reach out to me at [email protected]

Disclaimer: This is not investment advice. These weekly posts represent my simple thoughts, a few quotes, and some questions — for educational purposes only.