Ep. 15 - Risk and Reflection: Guest - Isaac St. John

Podcast Description

In this episode of Fulfillment Project, host Andy sits down with his lifelong friend, Isaac St. John, owner of Acorn and Oak PLLC. Isaac shares his journey of prioritizing family and faith over career in public accounting, offering insights on vocation, risk-taking, and personal growth. From his disciplined approach to reading to his candid LinkedIn presence, Isaac reveals how he turned "maybes" into "yeses" by taking calculated risks and staying true to his values.

The episode dives into the five pillars of fulfillment—money, health, community, values, and vocation—and challenges listeners to reflect on their own priorities through actionable wisdom and "Ikeisms." Perfect for aspiring entrepreneurs, professionals seeking purpose, or anyone looking to align their life with what truly matters.

Top Quotes

1. Isaac St. John: "I definitely called to lead that family life, be the head of the house and provide and bring my children closer to Jesus." (00:19)

2. Andy: "You are the average of the five people you spend the most time with." (01:12)

3. Isaac St. John: "When you start a book, you finish it. You don’t stop halfway through." (02:01)

4. Andy: "In order to get to the concluding thought, you have to read the whole book." (02:26)

5. Isaac St. John: "I can think of so many books that I’ve read that they weren’t really ready for me yet. But then as I developed as a person, I still remembered enough of the content that it shaped decisions I was making." (03:20)

6. Isaac St. John: "I reread books all the time." (03:49)

7. Isaac St. John: "The reality is who you are five years from now isn’t who you are today." (04:16)

8. Isaac St. John: "Candor is kindness." (09:32)

9. Andy: "Start with love, go to correction, end in affirmation." (09:38)

10. Isaac St. John: "Try to catch someone doing good because that positive reinforcement carries so much more weight." (10:56)

11. Andy: "If you’re too scared to act, then you’re too scared to grow." (11:49)

12. Isaac St. John: "You’re hitting way over 90 percent, right? So like reframing it so that they have the perspective of there’s all these things you did right." (13:51)

13. Andy: "If you aren’t your greatest critic, then you’re a loser." (14:17)

14. Isaac St. John: "You are who you surround yourself with." (42:57)

15. Isaac St. John: "There’s rewards that come with taking risk." (20:57)

16. Isaac St. John: "I made sure that I had a certain amount of runway so that if business was terrible and it was a crash and burn, I knew my family would be okay." (22:41)

17. Andy: "What passion do you have in your life that’s worth suffering for?" (24:46)

18. Isaac St. John: "There’s a lot to be said for showing up in person and closing things in person." (25:25)

19. Isaac St. John: "As humans, we have some automated responses almost built into us." (26:32)

20. Andy: "Pay yourself first in everything." (30:09)

21. Isaac St. John: "Unless you have that framework of how you’re directing your money, your money is just gonna do kind of what it wants." (31:33)

22. Isaac St. John: "Our jobs don’t define us, no, they don’t. They’re just what we do." (34:07)

23. Isaac St. John: "Work moves you towards sainthood. Being married moves you towards sainthood. Being single moves you towards sainthood." (39:40)

24. Isaac St. John: "If someone outside of my life looked in, what would they tell me is important to me?" (42:18)

Chapters

• 00:00: Introduction – Andy introduces Isaac St. John and the Fulfillment Project.

• 00:41: Childhood Friendship and Reading Habits – Andy and Isaac reminisce about their lifelong friendship and discuss Isaac’s disciplined approach to reading.

• 02:26: The Value of Rereading Books – Isaac challenges the idea of only reading immediately applicable books and shares his habit of rereading for long-term growth.

• 04:45: LinkedIn Presence and Candor – Isaac explains how his accidental LinkedIn following grew and introduces the concept of "candor is kindness."

• 09:32: Leadership and Positive Reinforcement – Isaac and Andy discuss catching people doing good, reframing mistakes, and the importance of self-criticism.

• 14:17: Self-Reflection and Wisdom – The power of revisiting books and reflecting on wisdom at different life stages.

• 17:04: Starting a Business – Isaac shares his journey of leaving a secure job to start Acorn and Oak, emphasizing risk appetite and calculated steps.

• 23:40: Turning Maybes into Yeses – Isaac’s creative approach to securing clients, including in-person persistence and leveraging human psychology.

• 27:29: Financial Discipline – Andy and Isaac discuss paying yourself first and the zero-based budget for financial control.

• 32:22: Defining Vocation – A deep dive into vocation, work, and family, with Isaac emphasizing that jobs support, not define, one’s true calling.

• 42:20: Priorities and Influence – Isaac introduces the "time audit" and the importance of choosing who influences your life intentionally.

• 49:11: The Five Pillars of Fulfillment – Isaac critiques the role of money in fulfillment, emphasizing community, values, vocation, and health.

• 55:07: Closing and Call to Action – Isaac shares where to find him on LinkedIn and describes his ideal customer, followed by Andy’s closing remarks.