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- Exploring the ask, retiring, and buying back time
Exploring the ask, retiring, and buying back time
Logan
November 13, 2025
In partnership with
Exploring the ask, retiring, and buying back time
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 Ask:
During a college internship, I got coffee with a company leader who told me something that changed how I think about opportunity:
If you don’t a-s-k, you won’t g-e-t.
It was simple, yet profound and effective.
I realized that everything we have is a giant function of our ability to keep asking, and asking, and asking.
It wasn’t during the internship that I saw the elegance.
Waiting for a promotion, a raise, or more responsibility?
They don’t come to those who wait, but to those who ask. What if your manager has no idea you want more responsibility? What if they don’t know you have more capacity? What if they don’t know the value you’ve added over your tenure?
Even if your original ask comes up empty, you’re not walking home broke. You’ve pocketed some knowledge.
Ask what you might do right now that gets you closer to the raise, provides more responsibility, adds more value. This is feedback, this is the bridge to get what you want.
There’s no situation where you’ll walk away without more clarity than you started with.
Persistence is required, dogged persistence, because you will receive a lot of no’s along the way. It’s with each ask that you get feedback. And if you gamify that component of asking for things, seeing the ask as a magnet for feedback, that’s where value appears.
The shorter these feedback loops, the faster your learning.
You could go years waiting, years running suboptimal money strategies.
Or you could ask someone for feedback on your approach: what’s working, what’s broken, what opportunities exist?
In that light, can I ask you a favor? I need your feedback:
If you’ve been reading these for a while, what do you like and dislike?
What would you pay money for each month or year? How much?
What’s stopping you from sharing with a friend, coworker, family member?
Let me know, [email protected]
what can you start asking?
Two quotes on retiring:
When you press the button, write the letter, or send the notice, you need something else to occupy your mind and time.
“The secret of long life is double careers. One to about age sixty, then another for the next thirty years.”
“I see retirement as just another of these reinventions, another chance to do new things and be a new version of myself.”
Three questions on buying back time:
What could I buy that would save me time?
Are there second-order downsides to getting rid of some things that occupy my time? (i.e solving the time problem creates a new problem that is on par or worse than the time cost I was paying)
How much does it really cost to buy back different quantities of time?
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:
Without an ask
You’ll have to wait
To see what comes
From the fickle hand of fate
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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