Don’t Treat Retirement Like One-Size-Fits-All with Bonnie Treichel, Endeavor Law
Summary:
In this thoughtful and energizing episode of Don’t Do That, Kelly Waltrich sits down with Bonnie Treichel, Chief Solutions Officer at Endeavor Retirement and Endeavor Law, to explore why retirement planning—and entrepreneurship—should never follow rigid, one-size-fits-all rules.
Bonnie shares her path as a multi-business founder serving financial advisors in the retirement plan and wealth management space, including why she chose the title “Chief Solutions Officer,” how listening to clients led to launching a second business, and where advisors continue to misstep around compliance, ERISA, and participant communication.
The conversation centers on Bonnie’s upcoming book, Your Retirement Sketchbook (co-authored with Jamie Hopkins), which reframes retirement as a flexible, evolving journey shaped by personal values, emotions, and life transitions—not just spreadsheets. Together, Kelly and Bonnie discuss how advisors can better support clients through both the financial and human sides of retirement, the power of “what-if” planning, and why failure has been one of Bonnie’s greatest teachers.
Kelly and Bonnie cover:
00:00 Don’t Treat Retirement Like One-Size-Fits-All
00:24 Welcome to the Don’t Do That Podcast
01:22 Meet Bonnie Treichel and Endeavor Retirement
02:42 Building Two Businesses by Listening to Clients
03:41 Why “Chief Solutions Officer” (and Not CEO)
04:31 The Compliance Gaps Advisors Miss in Retirement Plans
05:53 Turning Complex Rules into Client-Friendly Marketing
06:40 Advisory Boards, Networking, and Pickleball Lessons
09:21 Introducing Your Retirement Sketchbook
10:21 Making Retirement Planning Approachable and Visual
11:53 Social Security, Flexibility, and Personal Philosophy
14:10 Planning as a “What-If” Exercise, Not a Formula
15:18 The Emotional Side of Retirement Nobody Talks About
16:12 Identity, Community, and Purpose After Work
18:11 Don’t Do That: Retirement Is Not One-Size-Fits-All
19:13 Don’t Be Afraid to Fail (In Business or Life)
21:02 Learning Faster Through Mistakes
22:08 Why Failure Makes Better Advisors and Leaders
23:07 Final Thoughts, Book Details, and What Not to Do Next
Connect with Kelly Waltrich:
Connect with Bonnie Treichel:
- LinkedIn: Bonnie Treichel
About Our Guest:
Bonnie Treichel is the Founder and Chief Solutions Officer of Endeavor Retirement, a consulting firm that helps plan sponsors, advisors, and service providers solve complex challenges in the retirement plan industry. Drawing on her background as both an ERISA attorney and advisor, Bonnie delivers practical governance and compliance solutions for the day-to-day realities of running successful retirement plans.
Bonnie is also a Partner at Endeavor Law, where she advises financial services firms on retirement plan-related documentation, regulation, compliance, and litigation. A recognized thought leader in retirement plan governance, she has been featured in The Wall Street Journal, InvestmentNews, PlanAdviser, 401(k) Specialist, Ignites, NAPA Net Daily, and the Journal of Pension Benefits.
Her accolades include InvestmentNews 40 Under 40 (2023), the ABA’s On the Rise – Top 40 Young Lawyers Award (2022), and NAPA Top Influencers (2024, 2025). Bonnie is an active member of the American Retirement Association and the American Bar Association’s Tax Division, serves on RISA’s advisory board, and is a board member of the FinServ Foundation. Outside of work, she enjoys traveling, running, biking, spending time with her golden retrievers, Sadie and Sunny, and volunteering with Make-A-Wish.