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The greatest gift of retirement is also its greatest challenge…
When the daily structure and duties of work fall away, you’re left with something both exciting and daunting: a wide-open expanse of time. With this time comes an abundance of choice — how to spend your days, whom to spend them with, what to prioritize… Often these choices sit in opposition of one another as retirement paradoxes.

Without a clear path forward, it’s easy to feel unmoored by the sheer number of options, stuck in the tug-of-war of opposing desires, or regret that you’re missing chances to use your experience and resources meaningfully.

That’s where Retirement Coaching comes in…
You don’t have to face these tensions alone. I’m Sherri Shapiro. I coach thoughtful, curious, and experienced individuals, who are financially prepared for retirement. My clients value lifestyle planning as much as financial planning, and they view coaching as an investment in their ongoing pursuit of a life that brings them meaning.

As your coaching partner, I create a structured space to pause, sort through the noise, and see your choices more clearly. Together we’ll uncover what matters most to you, so you can transform your retirement paradoxes into retirement opportunities.

Over a 90-day period, you’ll trade uncertainty for clarity and momentum by designing your next phase of life through a straightforward three-phase process. — Investigate, Imagine, Invent. You’ll walk away with a vision and personalized plan to create a life that’s filled with intention and integrity.

Don’t let the paradoxes of retirement turn this gift of time into regret. Take the first step todayschedule an Intro Call to start shaping a retirement that works for you.

3-month packages for 6, 1-hour private coaching sessions start at $945.

What Can I Expect from Retirement Coaching?
You can expect to map out your future — on your terms — through thought-provoking conversations and exercises that take place during 6 outcome-oriented 1-hour sessions over 90 days. Below is an overview of a standard process that I use with my clients. You’ll have the option to customize each phase based on your own needs.

1. Investigate: Assess Who You Are
We first take stock of who you are and where you are by:

• Exploring your values and identity.

• Gauging what activities energize and drain you & when.

• Identifying your unique retirement paradoxes.

2. Imagine: Envision Possibilities
Next, the question shifts to: Who am I moving toward? In this phase, we:

Brainstorm ideas for the retirement that you really want.

Design a vision encompassing these findings & enabling you to navigate your paradoxes.

3. Invent: Put It Into Practice
Here retirement stops being an idea and becomes your actual life as we:

• Create a personalized roadmap with goals & accountability.

Build routines that sustain energy, health, & purpose.

• Discuss how to adjust when life surprises you (because it always will).


3-month packages for 6, 1-hour private coaching sessions start at $945.

When Should I Seek Out Retirement Coaching?

My clients seek coaching at various stages of their retirement journey, whether they are pondering, planning or participating in their retirement. They find unique questions and paradoxes that arise at each of these stages, as seen by the examples below:

Pondering Retirement: 3-5 years before your Retirement Date

• How can I start exploring retirement possibilities now?

• What plans do I need now so retirement doesn’t feel wasted later?

• Do I even want to retire?

Planning Retirement: 6-12 months before your Retirement Date

• Am I ready for this transition?

• How will I fill my days in retirement?

• Do I want to make significant changes to my life?

• Who will I be without my job title?

Participating in Retirement: Day 1 of Retirement to TODAY

• What are additional ways that I could be using my time?

Why do I feel uncomfortable living off of my savings?

What will be my legacy?

FAQs

  • Therapy looks at your past e.g., healing old wounds or resolving unfinished business.

    Coaching looks to the future e.g., identifying possibilities, creating structure, and helping you take purposeful action.

    Knowing these definitions, you can decide which option is best for your current needs.

  • That’s a fair question. I’m not retired myself, and I don’t pretend to be. What I bring isn’t my own retirement story — it’s a proven process, professional coaching training, and years of experience helping people navigate during times of transition.

    Here’s what qualifies me:

    • ICF Training & Standards — I’ve been trained and credentialed through the International Coaching Federation, which holds coaches to the highest global standards of ethics, effectiveness, and professionalism. That means you’re working with someone who is skilled in the art and science of coaching — not just offering casual advice.

    • Career in Change Management — My background includes years of working with individuals and organizations through major transitions. Retirement is one of the biggest transitions you’ll ever face, and I bring tested tools to help you navigate it with confidence.

    • Specialized Retirement Focus — Unlike general life coaches, I focus specifically on the paradoxes of retirement. My entire approach is designed to help you move beyond financial planning and into lifestyle planning.

    • Your Experience + My Process — You bring decades of life and career wisdom. I bring a structured process to help you shape that wisdom into your next chapter. Together, we create a retirement that is purposeful and balanced.

  • That’s perfectly okay. Many clients start with curiosity, not certainty. What I recommend is a conversation — no pressure, no obligation — to explore what’s on your mind about retirement. You’ll leave with clarity about whether coaching is the right next step for you.

  • Coaching isn’t about me handing you a giant to-do list. It’s about creating a plan that fits you — your pace, your energy, your priorities. Some clients dive in with big projects, others take smaller steps that feel sustainable. Both approaches are valid.

    What matters isn’t checking off every box — it’s that you’re making meaningful progress in the direction you want to go. As your coach, I’ll help you choose the right amount of work for where you are, and I’ll keep you accountable without overwhelming you.

    In other words, this is not about doing everone. It’s about doing the right work — the pieces that will actually make your retirement feel fulfilling, purposeful, and uniquely yours.

  • Over a 90-day period, we would meet for 6, 1-hour session. Sessions are scheduled for the same day and time every other week.

    We can easily make adjustments to this schedule to accommodate travel, holidays or other commitments as needed.

  • Absolutely — and many people try. The challenge is that information alone doesn’t create transformation. You can gather endless ideas, but it’s hard to filter what matters, stay accountable, and move from ideas into action. Coaching gives you something these esources can’t:

    • A thinking partner who reflects back what you can’t see on your own.

    • A structured process that moves you from reflection to action.

    • Accountability to keep you moving forward when resistance shows up.

    You can collect ideas from ChatGPT (or anywhere else) — but coaching turns those ideas into a plan you’ll actually live.

  • That’s a wise question — and the truth is, retirement coaching is an investment in protecting the life you’ve worked so hard to create.

    You’ve already invested decades building your career and saving financially for retirement. But money alone doesn’t guarantee fulfillment. Without a clear plan for your time, identity, and purpose, it’s easy to feel lost, restless, or dissatisfied — no matter how financially secure you are.

    Retirement coaching helps you:

    • Avoid costly mistakes like drifting into boredom, overcommitting out of guilt, or making choices that don’t align with your values.

    • Make the most of your financial plan by aligning it with a lifestyle plan — so your resources fuel meaning, not just comfort.

    • Gain clarity and focus faster than trying to figure it out alone, which saves time, energy, and money in the long run.

    You invested in your financial security. Coaching ensures you also invest in your personal fulfillment — so those savings translate into a life that feels rich, not just funded.

About Me

I bring a long professional history of working with individuals who are experiencing change to my Retirement Coaching practice. Before becoming a coach, I was a Change Management consultant for over 15 years, partnering with multi-national companies — and their people — during times of transformation. My experience taught me that, above all else, what truly determines successful change is how people reimagine their identity, move forward and adapt. I believe the same is true for individuals who are navigating one of life’s biggest transitions: retirement.

As an ICF-accredited coach, my approach blends proven coaching and change management practices with insights from modern thought leaders in the areas of life design, time management, financial psychology, conscious leadership, and purposeful aging. This integration allows me to provide clients with fresh perspectives and practical tools while honoring the deeper questions of identity, meaning, and legacy.

When partnering with clients, I show up as:

objective and practical – providing grounded, realistic guidance.

non-judgmental and respectful – creating a safe, open space for exploration.

challenging yet empathetic – asking the hard questions while offering warmth and understanding.

professional, but with laughter – balancing seriousness with humanity and lightness.

More About Me
I was born and raised in New Orleans, LA, which will always be home in my heart. I now live in beautiful Boulder, CO, following a long-time residence in Atlanta, GA. When I am not coaching, I can be found hiking or on my Stand Up Paddleboard, or out exploring the world (52 countries visited… and counting).

Here are some testimonials from some of my previous clients:
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