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_{Exploring the procrastinator’s dilemma, learning by doing, and planning and scheduling}

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:}

The Procrastinator’s Dilemma:

What is the procrastinator’s dilemma?

It’s knowing that we should begin our work early—while we don’t need to—yet, despite knowing this, we defer. We wait until our internal clocks sound the alarm of urgency, warning us to begin our Herculean efforts so we may complete the task on time.

And when we inevitably do, we swear to be better.
We swear we’ll start earlier next time.
Yet we never do.
Same cycle. Same stress. Same procrastination.

For a weekly project, instead of stacking a block each day, we wait for the final hour to stack all seven of them the day of. We get it done—barely. And in our haste, we produce shoddy, “good enough” work. Not great, not terrible. But the box gets checked.

These kinds of cyclical effort patterns create their own negative feedback loop:

Delaying work creates more work → More work requires a higher effort in the final hour → A bigger effort in the final hour is more exhausting → Exhaustion leads to delaying the next cycle

Repeat. Repeat. Repeat.

Any long lead time is a procrastinator’s worst nightmare. And the longer the lead time, the easier it is to slip into time’s vortex.

Think about a graduate fresh out of college. They’ve got a bag full of student loan debt, absolutely no money, and something they’ve never had before: a salary.

With this salary, the world seems limitless.
No more ramen.
No more cheap drinks.
No more slumming it in a grungy apartment with seven other people.
This is freedom.

And starting out, the world is vast and unexplored—a problem money can solve.

Parents, professors, and wise old neighbors all echo the trope: “You should save while you’re young.”

But unchained from the shackles of institutional education, the taste of freedom now mutes any logical, dogmatic money spiel—especially one that matters forty years from now. So what do they do? They live.

They travel.
They bounce around jobs.
They upgrade their wardrobes, buy a car that’s more reliable—maybe even a little lavish compared to the old college clunker.

And then there’s the wedding.
The honeymoon.
The house.
The kids.

Suddenly, the 20s are gone.
The 30s are well on their way.

Retirement seems a little closer, but how can they think about that?
Student loans still linger.
The car and mortgage payments are heavy.
What’s left?

So they squeeze through the 30s and 40s, raising kids, saving for college.
Retirement still feels far off—but there’s a greater sense of urgency.

At this point, the long runway has slid away, and the procrastinator’s dilemma is here again.

To sufficiently eclipse the giant hurdle of required retirement savings, they now must summon a Herculean effort—and likely push their retirement date back.

How did this happen?

Subtle, innocent little pushes.
Debates with our past selves.
Handshake deals sealed with the promise of starting tomorrow.

No one tied us to the mast when the sirens sang “don’t worry, you’ve got time.”
And we listened anyway.

To beat the procrastinator’s dilemma, you must work when you feel you don’t have to. You can’t wait for urgency This is the premise behind Jeff Cunningham’s “consistently good vs. occasionally great” philosophy. The turtle wins the long race against an occasionally fast rabbit.

You stack one single brick today and when you show up the next day, you resume building—but from a higher tower. You’re closer to the goal, and the required effort is far more manageable.

Our aim is to systematize the work across time, not merely complete the work and check a box.

In what areas do you see this pattern play out?

_{Two quotes on learning by doing:}

Grasping concepts from pages or professors may not be your best chance at learning. Some things we must go out and do to truly hold onto. Jimmy Iovine became a legendary record producer because Roy Cicala worked through him — he taught Jimmy the board by having him move the dials and hear the sounds Roy wanted him to hear.

_{Three questions on planning and scheduling:}

1. How much extra mental load do I carry trying to keep tasks in my head instead of in a calendar/reminders app?

2. What if I scheduled any non-automated future task or to-do — every single one of them — the slightest and the most consequential?

3. What if I’m not forgetful and lazy, but unorganized?

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:}

Contact Me:

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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