Empowering Child-Free Entrepreneurs

Episode Summary

Retirement isn’t just a financial transition, it’s a psychological and emotional one, too. In this episode of Humans vs. Retirement, I sit down with Lindsay Troxell, a coach and life planner who has been at the forefront of shifting the financial industry’s focus toward a more human-first approach.

Lindsay shares powerful insights on mindset, identity, and habits, and why most people unknowingly experience an identity crisis in retirement. Lindsay and I explore how to reshape your beliefs, redefine purpose, and build new habits for a fulfilling second half of life.

If you’ve ever asked yourself: Who am I without my job title? How do I retire with meaning? or Why does retirement feel like a letdown?, this episode is for you.

What You’ll Learn in This Episode

• Why retirement isn’t just about money—and why financial security alone won’t make you happy.
• How habits and mindset shape your retirement experience (and how to rewire them).
• The common identity crisis retirees face—and how to navigate it with confidence.
• Why traditional financial planning treats retirement as a math problem, when it’s actually a human challenge.
• How to develop purpose, fulfillment, and structure in retirement.
• The importance of coaching and why having a financial plan isn’t enough.
• How Lindsay’s business, Discretionary Inc., helps child-free entrepreneurs create a unique life plan that reflects their values and goals.

Key Topics Discussed

[00:02] – Introduction & Catching Up

• Lindsay’s background in financial coaching and life planning.
• The shift from numbers-focused planning to a holistic, human-first approach.

[00:10] – The Mindset Shift for Retirement

• Why people treat retirement as a math problem (and why that’s wrong).
• The emotional journey of retirement—why so many people feel lost after stopping work.
• The three-dimensional approach to retirement: wealth, health, and identity.

[00:25] – Identity & Purpose in Retirement

• The biggest identity crisis retirees face (losing structure, title, and purpose).
• Why your identity is more than your job title.
• The "retire with" framework: What are you bringing into retirement?

[00:40] – Mindset, Habits & Breaking Old Patterns

• How beliefs shape our retirement experience.
• The role of growth mindset and beginner mindset in reinvention.
• The importance of failure and experimentation in building a fulfilling retirement.

[00:55] – Retirement & Relationships: The Gray Divorce Trend

• How retirement impacts marriages and partnerships.
• The rising trend of gray divorce (and why couples struggle post-retirement).
• The three journeys: Your individual path, your partner’s path, and your shared path.

[01:10] – The Future of Retirement & Financial Planning

• Why coaching is the missing link in financial planning.
• How financial professionals need to adapt their services to serve clients better.
• Lindsay’s business Discretionary Inc. and why child-free entrepreneurs need specialized financial and life planning.

[01:25] – Final Takeaways

• Why the traditional retirement model is outdated and needs to evolve.
• Practical steps to redefine your mindset and habits for a more fulfilling life.
• Lindsay’s best advice for people approaching retirement.

Books & Resources Mentioned

Books:

• The Psychology of Money – Morgan Housel
• Mindset: The New Psychology of Success – Carol S. Dweck
• Let Them – Mel Robbins
• Meditations – Marcus Aurelius
• Letters from a Stoic – Seneca
• The Bhagavad Gita – Hindu Philosophy on Purpose & Duty

Research & Studies:

• Retirement & Depression: 40% increased risk of depression in retirees.
• Gray Divorce Trends: Divorce rates for 60+ have risen from 9% (1990) to 40% (recent years).

Additional Resources:

• Morgan Housel’s Blog on Behavioral Finance
• Carol Dweck’s Research on Growth Mindset
• George Kinder’s Life Planning Method

Connect with Us

Follow Lindsay Troxell:

• Website: www.ourcoachinginitiative.com/
• LinkedIn: www.linkedin.com/in/lindsaytroxell/

Follow Dan & The Podcast:

• Website: www.humansvsretirement.com
• LinkedIn: www.linkedin.com/in/dan-haylett-retirement-coach/
• Subscribe on Apple Podcasts | Spotify | YouTube

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