The 4 Phases of Retirement: What No One Tells You About Life After Work [Ep. 33]

About This Episode

Retirement planning tends to focus almost entirely on the numbers: how much you’ve saved, what your withdrawal rate should be, when to claim Social Security. Those questions matter. But they don’t answer a different question many retirees find themselves asking six months, or six years, into retirement: 

Why doesn’t this feel the way I thought it would? 

In a recent episode of GDS Unplugged, Glen Smith, Founder, CEO & CIO of GDS Wealth Management, and Robert Casey, Senior Vice President & Cofounder, discussed a framework they have used with clients for more than a decade: retirement isn’t a single experience; it’s four distinct phases. Each one comes with its own emotional shifts, its own risks, and its own financial planning considerations; and understanding which phase you’re in can help put some of the uncertainty into context.

Phase One: The Honeymoon Phase 

The first phase is the one most people picture when they imagine retirement: travel, freedom, and the alarm clock finally staying off. As Glen explains, this phase is less about adding new things to your life and more about removing the stress, structure, and obligations that built up over a career. 

It’s an important phase, and it’s meant to be enjoyed. But Glen is direct about the mistake many retirees make here: mistaking the relief of phase one for lasting fulfillment. That relief isn’t always permanent, and treating this phase as “the rest of retirement” can lead to confusion and anxiety later on. 

Phase Two: The Identity Shift 

For most of a career, identity and profession become deeply intertwined. It’s often the first thing people ask when they meet someone new: What do you do? When that professional identity disappears, the impact can be more significant than most people expect. 

Glen shares an example from the podcast: a client, nine months into retirement, calling on a Monday morning simply because Mondays used to mean something, and suddenly they didn’t. It’s a moment some retirees may recognize. As Glen and Robert discuss, this phase isn’t about avoiding that shift; it’s about being self-aware that it’s happening, and understanding that it may be a normal, temporary part of the transition, not a sign that something has gone wrong.

Phase Three: Experimentation 

The third phase is about trying things: volunteering, part-time consulting, new hobbies, or even, in one memorable story from the podcast, becoming a school bus driver at a net worth north of $10 million. According to Glen, none of it counts as a failure if it doesn’t stick. Each experience simply provides information about what actually brings fulfillment. 

This phase also changes the financial planning conversation. Rather than relying on rigid income assumptions, Glen emphasizes that flexibility becomes the priority — keeping the financial plan and portfolio responsive as income needs change. 

Phase Four: Meaning Over Money 

The final phase isn’t about staying busy. It’s about doing things that are meaningful. Glen explains how the role of money changes here, too: for most of a working life, money functions as a scoreboard, a measure of progress and security. In phase four, that scoreboard mentality often gives way to something more personal, centered on the people and causes that matter most. 

Not everyone experiences this shift in the same way, and Glen is candid about that as well. For some retirees, money remains an important measure of security and progress throughout retirement.

What Should You Take Away From This? 

If any of these phases sound familiar, Glen and Robert suggest asking yourself a few questions: 

• Which phase am I in right now, and is that okay? 

• Am I mistaking a temporary feeling (relief, restlessness, uncertainty) for a permanent state? 

• Is my portfolio flexible enough to support experimentation, or is it built around a rigid assumption? 

• What would “meaningful,” rather than “busy,” actually look like for me? 

The answers can be just as important as any single number in a financial plan.

Final Thoughts

Retirement planning is often treated as a purely financial exercise, but as Glen and Robert discuss, the emotional transitions retirees go through are just as real, and just as important to plan for. Nothing is broken simply because retirement feels different than expected. It’s a phase, and phases move at different speeds for everyone. 

At GDS Wealth Management, we believe wealth management should extend beyond investment management alone. As a fee-only fiduciary firm, we coordinate financial planning, investment management, retirement planning, tax planning, and estate and legacy considerations to help clients navigate not just the financial side of retirement, but the personal transitions that come with it. 

Watch the full episode of GDS Unplugged to hear the complete conversation between Glen and Robert, including the stories behind each phase and how advisors coach clients through them. If you’d like to discuss where you are in your own retirement journey, you can schedule a complimentary consultation.