Is the constant push to be great quietly making life (and money) harder than it needs to be?
This vault-worthy episode from 2023 hits differently, especially during a season when expectations run high and energy can run low. Joe Saul-Sehy is joined by Len Penzo, Paulette Perhach, Diania Merriam, and special guest Stephanie O’Connell Rodriguez for a candid roundtable about ambition, procrastination, perfectionism, and the surprising freedom that comes from choosing good over exhausting.
Instead of chasing flawless systems or ideal outcomes, the conversation explores what actually moves the needle in real life. Building momentum. Removing friction. Letting go of the idea that every decision has to be optimized. Whether it’s money habits, career goals, or simply getting unstuck, this episode offers a calmer, more sustainable way forward without lowering your standards or your future.
Along the way, the group shares personal stories, practical strategies, and a few moments that only happen when smart people stop pretending they’ve got it all figured out. It’s thoughtful, honest, and exactly the kind of perspective many Stackers didn’t know they needed.
What You’ll Take Away from This Episode:
• Why perfection often slows progress more than fear or lack of knowledge
• How “good enough” can be a powerful financial strategy, not a compromise
• Practical ways to break through procrastination without burning out
• When delegation and automation actually help and when they just add complexity
• How to balance ambition with contentment without feeling like you’re settling
• Why consistency beats intensity in both money and life
Questions Worth Sitting With:
Where are you chasing “perfect” when “done” would be better? What would improve immediately if you lowered the bar just a little? Which money habit could become easier if you stopped optimizing it?
We’d love to hear your take. Share your thoughts in the Spotify comments or bring the conversation into the Basement Facebook group, especially if this episode gave you permission to ease up without giving up.
Sometimes the best financial move isn’t pushing harder. It’s choosing progress that actually fits your life.
This one’s a quiet classic, and those tend to age the best.
Please disregard any mention of current events. The original show notes can be found here.
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201
Enjoy!
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Written by: Kevin Bailey
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