For professionals preparing to retire and those newly retired
Winning@Retirement™ helps you prepare for the personal side of retirement so you can move forward with clarity, make thoughtful choices, and adjust as life unfolds.
The Spring 2027 Founding Group will be the first to experience this guided program.
Join the Winning@Retirement™ WaitlistWaitlist members will receive the first invitation to our free online workshop and early notice when Founding Group enrollment opens.
Work may end. A fully engaged life shouldn’t.
Early recognition
Before retirement
You may know when you want to retire, what your income will look like, and where you hope to travel.
But work has been doing more than filling your calendar. It has given your week a structure. People have called for your judgment. Your title has made introductions easy. Many of your relationships have come with the job.
When work ends, those things do not automatically replace themselves.
You may find yourself wondering:
Once retirement begins
The questions can become more immediate.
The phone is quieter. Tuesday morning is wide open. Someone asks what you do now, and the answer that once came easily suddenly takes more thought.
Nothing has gone wrong. You are beginning to see the parts of retirement that a financial plan cannot prepare for.
The Winning@Retirement™ difference
Financial planning prepares the portfolio. We prepare the person.
Most retirement planning helps you determine whether you have enough money for the years ahead. Winning@Retirement™ helps you decide what you want those years to hold.
You will look closely at what work is supporting now, what you want to carry forward, and what may need to be built before the role is gone.
Because a full calendar is not always the same as a fully engaged life. You can have errands, lunches, travel, exercise, and people to see, then still reach the end of the day with the sense that something in you is going unused.
The answer is not a rigid plan for the next 20 years. It is knowing what matters, making intentional choices, and having a way to adjust when life changes.
What becomes possible
Winning@Retirement™ is for professionals who want to shape who they are becoming and design a retirement that reflects it. Through focused preparation, guided support, and group coaching labs, you will learn how to:
Recognize the strengths, values, and parts of yourself that were never dependent on a title.
Find ways for your experience and judgment to remain useful without rebuilding the pressure of your career.
Talk with your partner, family, friends, and other important people about time, roles, expectations, and what may change.
Look beyond vacations and special occasions to the rhythm you want your regular weeks to hold.
Test what might fit, notice what is working, and change direction when something no longer feels right.
The method
The WIN Framework™ is the method behind Winning@Retirement™.
It takes you from deciding what you want, to making deliberate choices, to navigating the changes that come with a life still unfolding.
Clarity about what matters and what you want to carry forward.
Choices that move your life in the direction you want it to take.
The ability to notice, test, adjust, and keep moving.
You do not need every answer before retirement begins. You need a way to make the next good decision.
Your personal guide
Throughout Winning@Retirement™, you will create Your Winning Playbook, a personal guide for the life you want to shape.
Your Playbook will bring together:
It is designed to change with you. You can return to it when a new opportunity appears, a relationship changes, your weekly rhythm stops fitting, or life asks you to reconsider what comes next.
Meet Lori and Jenny
Winning@Retirement™ was created by Lori Harrow and Jenny James.
Lori is a Retirement Transition Specialist with a 14-year background in clinical mental health. Her experience helping adults move through major life transitions shapes the behavioral and psychological foundation of Winning@Retirement™.
Jenny spent 35 years in finance and has retired twice. Her first retirement began without a clear place for her experience and attention to go. She approached her second retirement differently, thinking carefully about what she wanted to carry forward before she left.
Together, we created Winning@Retirement™ for professionals who have prepared financially and want to prepare for the changes in identity, relevance, relationships, and everyday rhythm that can come when work ends.
The experience
Winning@Retirement™ combines focused self-paced content with a defined period of live guidance and personal support.
You will receive approximately 3½ to 4½ hours of focused core content, organized around clear milestones you can complete on your own schedule.
You will have lifetime access to the content, exercises, tools, and Your Winning Playbook.
Your eight-week support window gives you live guidance and direct access to Lori as you apply the work to your own life.
It includes:
The eight weeks describe how long the live support is available. They are not a deadline for finishing the program or a requirement to attend something every week. You can move through the core content at a pace that fits your life, while using the support window to ask questions, work through decisions, and receive feedback when it will be most useful.
Four parts of life worth preparing for
Who are you when your title is no longer the quickest way to explain yourself?
Recognize what belongs to you, not only to the role you held.
Where do you want your experience, perspective, and judgment to go?
You can remain useful without recreating the demands of your career.
How might retirement change the time, roles, and expectations you share with your partner, family, friends, community, and work relationships?
More time together still needs a conversation.
What do you want an ordinary week to feel like?
A satisfying retirement needs more than trips and special occasions. It also needs a rhythm that works on a regular Tuesday.
The research
A 2025 Financial Planning Association survey gathered responses from 167 financial planners. More than half believed their clients were financially prepared for retirement. Only 11% believed their clients were emotionally prepared.
The planners reported concerns about adapting to life without work, losing a sense of identity, and becoming a burden to loved ones.
Money matters. So does preparing for the changes in identity, relationships, usefulness, and everyday life that can come when work ends.
Source: Financial Planning Association, 2025 Trends in Retirement Planning
11%
of the 167 financial planners surveyed believed their clients were emotionally prepared for retirement.
The free workshop
In early 2027, we will offer a free online workshop introducing the ideas behind Winning@Retirement™ and why preparing the person matters alongside preparing the portfolio.
You will also get a closer look at the Spring 2027 Founding Group and decide whether the program may be right for you.
Winning@Retirement™ waitlist members will receive the first invitation when workshop registration opens.
Join the Winning@Retirement™ WaitlistThe Retirement Transition Audit
The free Retirement Transition Audit gives you a personal look at four parts of life that work may be supporting more than you realize:
In about 10 minutes, you will see where you already feel prepared and which area may deserve more attention as retirement approaches or begins.
Take the Free Audit16 questions. Free. Immediate results.
Spring 2027 Founding Group
The Spring 2027 Founding Group will be the first group guided through the complete Winning@Retirement™ experience. Join the waitlist to:
Joining the waitlist does not commit you to the program. It simply makes sure you hear from us first.
Work may end. A fully engaged life shouldn’t.
Work may end. A fully engaged life shouldn’t.
Helping accomplished professionals prepare for the personal side of retirement — identity, relevance, relationships, and the rhythm of an ordinary week.
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