The Retirement Mindset Shift with Lindsay Troxell

Mar 15, 2025

Lindsay Troxell, a coach and life planner, dives into the emotional side of retirement. She reveals how financial readiness doesn’t guarantee happiness and discusses the identity crises that often accompany this life transition. Lindsay emphasizes the importance of redefining purpose and values, advocating for a holistic approach to planning. She encourages embracing a growth mindset to find joy and fulfillment in the second half of life, especially for child-free entrepreneurs, shifting the focus from mere numbers to authentic living.

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INSIGHT

Retirement as Human Transition

Retirement is a human transition involving emotional, physical, social, and purpose needs, not just a financial math problem.
Preparing emotionally for retirement prevents shock and opens opportunities for joy and resilience.

ANECDOTE

Reinventing Identity in Retirement

A client discovered that retirement required reinventing parts of his identity tied to his executive role.
Rekindling neglected aspects like spirituality allowed him to embrace retirement with excitement and purpose.

ADVICE

Shape Retirement Identity Purpose

List all your identities, intentional and assigned, then decide which to keep or release going forward.
Explore the values, actions, and purposes tied to your core identities to shape your post-retirement self.

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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).