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_{Exploring retention vs outsourcing, increasing power, and settling}

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.

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_{One idea to experiment with:}

Retention vs Outsourcing:

Look around. More and more of your family, friends, and coworkers are integrating AI into their daily lives. It’s no longer an obscure search engine or a cold, customized solution provider. AI is a friend, a therapist, an advisor, a chef, a computer engineer, an Excel wizard, a world-class artist, an interior designer, and a workout coach — nearly anything you want it to be. It knows your thought patterns, your preferences, even your tone of voice.

We’ve already jumped headfirst into a technological revolution that will bring more productivity and longevity than we can fathom. The economy will grow. Medicine will improve. Mistakes will be reduced, and so will death rates.

But what about our money?

I’m willing to bet there’s plenty of low-hanging financial fruit AI can help you pick. Need a net worth tracker? Built in seconds. Need a budget? It can distill your last twelve months of spending before you set your coffee down. Need your investments analyzed? Done. There are still complex elements of planning best left to real advisors, but the tool in your pocket can already improve your financial life now — not just at next year’s annual meeting.

Yet as AI grows more capable, the temptation will be to outsource everything — even the things worth keeping. We’ll face the question of retention: should we do this ourselves, or let our artificial friend do it for us?

Some tasks are worth doing for their own sake—autotelic activities. The meaning comes from the process, not the result. Think gardening, cooking a meal from scratch, or writing in a journal. Optimizing these for efficiency can poison the joy they bring.

This week, I was tempted to have ChatGPT write for me. I already use it as an editor, so it would be easy: generate a list of ideas, pick my favorite, instruct the composition. Ten minutes, tops. I know because I tried it. The result was excellent — but it wasn’t mine.

I had to remind myself that the small inconvenience of writing is the exact inconvenience I choose. I like being generative. I like the process. Removing the process in favor of cold output is a recipe for efficient unhappiness.

It’s the same reason I’d never take a magic fitness pill. Even if it gave me the same physical results, I’d miss the satisfaction of moving my body, of sweating, of pushing myself. The process is the reward.

So while efficiency rises all around us, the more important question will be: What do I want to keep doing despite the inefficiencies?

AI could be your best friend — no fights, no awkward silences, always agreeable. But is that the friendship you want? AI can create for you — no staring at a blank page, no struggle. But is that the creativity you want?

In a world where we can outsource almost everything, maybe the most valuable thing to know is what’s worth optimizing. 

_{Two quotes on increasing power:}

Power is accessible outside of the structural imperative. Robert Caro didn’t think power had to corrupt but was certain that it revealed what already existed inside. Increasing power isn’t a bad thing and can wield many positive downstream effects.  

_{Three questions on settling:}

1. Where am I settling because things are fine? 

2. What terms am I accepting because I don’t see upside outside of my existing situation?

3. How much downside-casting occurs in my attempt to rebel? But what if this happens? What about that? What if I can’t find something better?

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.

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