Podcast Summary: The Stacking Benjamins Show
Episode: The Perfection Trap: Why Striving Less Might Help You Save More (SB1779)
Date: December 26, 2025
Host: Joe Saul-Sehy
Guests: Stephanie O’Connell Rodriguez (Money Confidential), Diana (Economy Conference), Len Penzo, Paulette Perhach
Overview:
This episode dives into the hidden costs of perfectionism—in finance, work, and life—and explores the freeing benefits of embracing “good enough.” The roundtable unpacks how the relentless drive for greatness can hold people back from making progress, cause procrastination, and even lead to burnout, especially when it comes to managing money. With signature humor and warmth, Joe Saul-Sehy and his co-hosts tackle the Outside Magazine article, "It's OK To Be Good And Not Great," discussing practical ways to move forward, celebrate small wins, and create systems that prioritize action over perfection.
Main Discussion Points & Insights
1. Perfectionism and Its Paralysis
[13:23] - The episode is sparked by Brad Stulberg’s Outside Magazine piece, asking: “Is it OK to be good and not great?”
- Paulette Perhach describes letting go of her morning routine to connect with a neighbor, embracing presence over rigid productivity:
“It is this balance of presence and growth where it's like, I want to grow and do great things, but I also want to enjoy the present moment.” (13:23)
- Stephanie O’Connell Rodriguez shares how striving for “the best” can undermine authentic growth, advocating for a well-rounded, diversified life instead:
"Perfection...is just really antithetical to growth that feels authentic and connected to your uniqueness.” (15:51)
2. Community vs. Competition
[18:46] - Paulette reframes striving for “the best” as sometimes antisocial:
“I truly started to really feel that I was in community when I didn’t need to be the best... striving to be the best, in a way, is antisocial behavior.”
- She recounts a South American strawberry-sellers’ community where no one aims to outshine the other, linking the idea to how creative communities thrive.
3. Letting Go & Delegation—Why “Jack of All Trades” Matters
[21:59] - Len Penzo distinguishes between striving for greatness and getting stuck chasing perfection, highlighting the value of being a “Jack of all trades”:
“Be great, but don't try to be perfect... You're never going to be perfect. Mistakes help you grow and are part of life.”
- Delegation is emphasized—knowing when to outsource or ask for help instead of inefficiently doing everything alone.
“Jacks of all trades are very important people. They're not experts at anything, but they're good at knowing what to do and who to contact.” (21:59)
4. Perfectionism in Leadership & Event Planning
[25:07] - Diana describes crumbling under self-imposed pressure while organizing the Economy Conference, only to realize that letting tasks go didn’t harm the end result:
“I felt like I was failing... But then I showed up to the event and guess what? It was fine. Better than fine. It was awesome.” (26:37)
- She recognizes overcomplicating things and missing the joy in her work, learning to prioritize relationships over minutiae.
5. Procrastination: When the Drive for “Perfect” Stops Us From Starting
[40:08]
- Stephanie admits:
“I am incredibly unproductive. This idea of having to be great and perfect is often conflated with productivity and hustle culture.”
- The group discusses tools for overcoming inaction:
- External deadlines and constraints
- “Body doubling” (having an accountability partner physically present)
- Redefining procrastination as potentially productive reflection and rejecting shame
6. Constraints: Help or Hindrance?
[43:55]
- Constraints and deadlines help creatives and entrepreneurs finish work by forcing decisions:
“An artist without constraints will never get anything done.” (Joe referencing producer Don Hahn; 44:30)
Money & Perfectionism: Practical Takeaways
7. Financial Paralysis & Small Steps Forward
[48:47]
- Many people freeze financially, feeling not “great” with money, which blocks progress (not starting a savings account, opening a Roth IRA, etc.).
- Len:
“If you want to invest in something you’re not good at, delegate out... Don't let perfect be the enemy of good.”
- Paulette and Stephanie advocate for automation, support groups, robo-advisors, and focusing on behavior rather than labeling oneself as “bad with money.”
8. Identity vs. Behavior
[53:19]
- Stephanie notes that people see financial struggles as a reflection of their worth, making change difficult:
“Every moment is an opportunity for a new behavior. If you internalize money struggles as your identity, it's very hard to make changes.”
- She encourages clients to find what they’re doing right, no matter how small, and build from there.
9. Curiosity Over Shame; Progress Over Perfection
- Diana’s “let curiosity be bigger than fear” mantra is echoed: Confronting financial realities—even uncomfortable ones—creates the space for positive action.
10. Work From Strength, Not Just Fixing Flaws
[56:48]
- Joe shares a lesson from Strategic Coach:
“If you're always working on the things that you suck at, you might come up to the middle. If you work at what you're great at, you'll have exponential results.”
Notable Quotes & Memorable Moments
- Stephanie O’Connell Rodriguez [15:51]:
“Disconnect the idea of striving from the idea of being the best.”
- Diana [26:37]:
“I overcomplicate my work. A bunch of the stuff that I think I have to do, I actually don’t have to do it.”
- Len Penzo [21:59]:
“Jacks of all trades are very important people... They’re not experts at anything, but they’re good at knowing what to do and who to contact.”
- Paulette Perhach [52:16]:
“Buffalo know that if a storm is coming, they run toward the storm because they'll get through it faster... you have to run toward the storm and be willing to say, ‘I really struggle with this and I need help.’”
- Stephanie O’Connell Rodriguez [53:19]:
"If you attribute your money habits or outcomes to your identity, it’s very hard to make changes."
Key Timestamps for Important Segments
- 13:23 – Is striving to be great wrong? Presence vs. growth (Paulette)
- 15:51 – Authentic growth vs. perfection and happiness as a metric (Stephanie)
- 18:46 – Community vs. competition and the value of being "one of many" (Paulette)
- 21:59 – Letting go of perfection and the importance of delegation (Len)
- 25:07 & 26:37 – Event anxiety, letting go, and the power of showing up (Diana)
- 40:08 & 41:40 – Procrastination, external deadlines, and giving yourself grace (Stephanie)
- 44:30 – Constraints forcing completion in creative work (Joe referencing Don Hahn)
- 48:47 – Letting go of needing to be great with money; automation and delegation
- 53:19 – Identity vs. behavior in money management (Stephanie)
- 56:48 – Leveraging your strengths versus constantly fixing your flaws (Joe)
Takeaways
- Don’t let perfect be the enemy of good. Progress—especially with money and personal growth—often happens when we embrace “good enough” and just start.
- Find the joy in the process, not just the outcome. Growth is more satisfying than the pursuit of perfection.
- Delegate, automate, and ask for help. Outsourcing and accountability are powerful tools to overcome procrastination and perfectionist paralysis.
- Work from your strengths and positive behaviors. Building on what you do well is more impactful and enjoyable than constantly trying to fix your weaknesses.
- Curiosity is your ally. Let curiosity—not shame—lead you to uncover and address what’s holding you back in your financial life.
Original Tone & Humor
The hosts pepper the show with banter, self-deprecating jokes, and playful ribbing—especially around topics like junk mail, DoorDash, and the perils of KFC delivery. The group keeps a light, encouraging tone, emphasizing that everyone struggles with these issues and that small, imperfect actions are still worth celebrating.
For more, check out Stephanie’s Webby-winning podcast “Money Confidential” and Diana’s Economy Conference at economyconference.com (discount code provided for Stackers).