Private strategy session with Lori Harrow, Retirement Transition Specialist

WIN Strategy Session

You planned the money with help. You’ve been working out the rest of it alone.

Sixty minutes with me, then a written brief within 48 hours: my direct read on what deserves your attention now, and what I’d do about it first.

Book Your WIN Strategy Session$297

The retirement date may be clear. The personal transition is less so.

  • You’re ready for less pressure. You’re not ready to lose the strengths and judgment that good work brings out in you.
  • You want more time with the people who matter. You haven’t fully talked through what that time will mean for everyone.
  • You can picture the trips and the special plans. An ordinary Tuesday is harder to see.
  • Someone asks what you’ll do next, and your answer sounds thinner than you want it to.

The retirement date arrives on schedule. The personal decisions don’t.

You worked too hard to let the years after work happen by default.

One conversation, built around you

Before we meet, you’ll complete the Retirement Transition Audit. The Audit looks across four areas: your sense of self, where you feel useful, the people around you, and the rhythm of your days. If you’ve already taken it, we’ll use those results.

The Audit can show you a pattern. It can’t account for your retirement timeline, the role work still plays in your life, what the people around you are assuming, or what you’ve already put in place and tried.

Two people can get the same four scores and need completely different advice.

What we’ll work through

  • What work is still holding in place for you, and what shifts when it stops
  • What looks solid, and what’s resting on an assumption nobody has checked
  • The thing the Audit can’t tell you
  • Where your attention will make the most difference over the next year

This is where a pattern becomes specific to your life.

Book Your WIN Strategy Session$297

What you leave with

  • A direct read on where you actually are

    What deserves attention now, what can wait, and why.

  • Your WIN Strategy Brief

    Within 48 hours, in writing:

    • What I see
    • What may not yet be named
    • Why it matters in your circumstances
    • What I recommend
    • One action, conversation, or small experiment to begin in the next 30 days

Who this is for

The WIN Strategy Session is for you if you’re financially prepared, approaching retirement or newly retired, and life after work is asking for your attention.

Do any of these sound familiar?

  • Your financial plan is in place, but the personal side still feels unsettled
  • You can name what’s bothering you, but not what to do about it
  • You’ve been circling the same questions for months without landing anywhere
  • You’ve thought about getting help with this, but you don’t want to commit to something open-ended

This is one session, not a coaching commitment. It doesn’t include financial planning or therapy, and it isn’t ongoing.

How it works

  • Book your session.

    Choose your time and complete payment.

  • Complete the pre-work.

    The Retirement Transition Audit, if you haven’t taken it. I’ll review it before we meet.

  • Meet with me on Zoom.

    We’ll have a focused hour together. Your WIN Strategy Brief arrives by email within 48 hours.

If the answer is bigger than one session

Some people leave with exactly what they came for: a direction and a first move they can make on their own.

Others find the work is larger than one conversation. Winning@Retirement™ is the program where that work happens, with a founding group opening in Spring 2027. If it’s the right next step for you, I’ll say so in your brief.

Session clients get first word when the founding cohort opens. If you’re not ready to book, you can add your name to the waitlist now.

Meet Lori

Financial planning prepares the portfolio. We prepare the person.

For more than a decade I’ve sat with people one at a time through divorce, job loss, career changes, and retirement. Different events, same underlying work: how you see yourself, who you’re close to, and what your days are built around all shift at once.

My training is clinical: behavior change, and how people actually move through transition.

Retirement is the one people expect the least trouble from. It rarely announces itself as a problem. It arrives as ease. And ease, without intention, lets life get smaller.

I’m not going to tell you what your retirement should look like. I’ll tell you what I see in your answers, what I think you aren’t accounting for, and what I’d pay attention to first.

Lori Harrow, MA, LCMHCS, NCC
Retirement Transition Specialist
Co-Founder, Winning@Retirement™

The investment

Your WIN Strategy Session

$297

$297 through December 31. After that, $397.

Your session includes:

  • Advance review of your Retirement Transition Audit results and questionnaire
  • Private 60-minute Zoom consultation
  • WIN Strategy Brief within 48 hours, with my assessment, my recommendation, and one practical next action, conversation, or experiment
Book Your WIN Strategy Session$297


Need to move your time? One reschedule, with at least 24 hours’ notice.
Questions? [email protected]

You don’t have to decide the shape of the next twenty years. Knowing where to start is enough.

Book Your WIN Strategy Session
Winning@Retirement™

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.

Explore

Connect

winningatretirement.co Winning@Retirement™ © 2026 · All rights reserved. · Privacy Policy · Terms & Conditions