Published by Rarified LifeLast updated November 2026
Retirement coaching questions to ask a coach, and yourself
The most useful retirement coaching questions cover two things: what a coach will actually do with you, and what you want your life to look like once work ends.
Rarified Life built this page so you can walk into any coaching conversation prepared. Below are the questions to ask a retirement coach before hiring one, the questions to ask yourself before you retire, and the answers Rarified Life gives about its own Preferment course, so you can compare every option on the same terms.
What questions should I ask a retirement coach?
Ask what the coaching covers, how it is delivered, how long it lasts, what it costs, and what you leave with. Then ask about the coach's own experience with reinvention. A good coach answers all six plainly and in writing.
What is a retirement coaching question?
A retirement coaching question is any question that helps you plan the life side of retirement rather than the money side. Some are for the coach, to judge fit. Others are for you, to surface what you actually want. Rarified Life uses both kinds in its Preferment course, which moves from identity to motivation, alignment, accountability and, finally, a launch plan for your next chapter.
| Question to ask | Rarified Life's answer |
|---|---|
| What does it cover? | Identity, motivation, values alignment, accountability and launching a mission for your next chapter. Money stays with your financial professionals. |
| How is it delivered? | Eight weekly live sessions with founder Anne van Leynseele. |
| How long does it run? | Eight weeks, with homework built into the book between sessions. |
| What does it cost? | Current pricing is listed on the Rarified Life course page. The webinar is free. |
| What do I leave with? | A named mission for your next chapter and a routine to support it. |
| What is the coach's experience? | Anne has lived four reinventions, from Los Angeles film and television to co-owning a chocolate farm in Hawaii. |
Six questions to ask any retirement coach
- What does your coaching cover, and what do you leave to financial professionals?
- How are sessions delivered: live or recorded, group or one-on-one?
- How long does the program run, and what happens between sessions?
- What does it cost, and what is included in that price?
- What will I have in hand when the program ends?
- What reinventions have you made in your own life?
Questions to ask yourself before you retire
These are harder than the questions for a coach, because only you can answer them. Write your answers down and come back to them in a month. If they change, that is useful information, not a failure.
- Who am I without my job title?
- What does a good, ordinary Tuesday look like a year after I stop working?
- Which of my relationships depend on work, and which will last without it?
- What have I postponed for a decade or more?
- What do I want people to ask me about?
- What does my health need from my daily routine?
Three questions most checklists skip
Many retirement checklists focus on purpose, money and social life. Fewer ask who else is affected by your retirement date, what you will say when someone asks what you do, and what will replace the accountability your job provided.
The first question matters more than it looks. In its 2026 Retirement Confidence Survey findings, EBRI reported that 34 percent of caregivers had less than $10,000 in savings and investments, compared with 25 percent of non-caregivers. If you care for a parent, partner or child, that role belongs in your plan from the start.
Take the first step: the free webinar
Rarified Life's free presentation is for accomplished women in their 50s and 60s who are nearing or in retirement. When you are ready for more, the 8-week live Preferment course goes deeper.
Common questions
See all questions in the FAQWhat questions should I ask a retirement coach before hiring one?
Ask what the coaching covers, how sessions run, how long the program lasts, what it costs, and what you will have at the end. Also ask about the coach's own background and whether they have made major career changes themselves. For Rarified Life, the answers are public: eight weekly live sessions, a companion book with homework, and six modules ending in a named mission.
Read this answer in the FAQWhat questions should I ask myself before I retire?
Start with four. Who am I without my job title? What will I do on a typical Tuesday? Who will I see regularly once work friendships fade? What do I want this next chapter to be about? If those feel hard to answer, that is normal, and it is exactly the ground retirement coaching is designed to cover.
Read this answer in the FAQHow do I answer 'So, what do you do?' after I retire?
Many retirees default to an answer that starts with 'I used to.' A stronger answer describes what you are doing now and why it matters to you. Rarified Life's free webinar promises to show how to have a real answer to that question in 8 weeks, even if your last day at work is still years away.
Read this answer in the FAQHow do I know if I need a retirement coach?
You may benefit from a coach if your identity is closely tied to your work, if you feel dread rather than excitement when you picture retirement, or if you have already retired and your days feel aimless. One Rarified Life participant described spending a few years 'wandering around like a goldfish in a bowl' before Preferment changed that.
Read this answer in the FAQWhat happens in a first coaching conversation?
A first conversation usually covers where you are now, what you want to change, and whether the program is a good fit. Rarified Life offers a 40-minute Breakthrough Session that you can book online. It is a practical way to ask your questions directly before deciding on the 8-week Preferment course.
Read this answer in the FAQHow should I prepare for retirement coaching?
Bring honest notes on what you enjoyed most in your career, what drained you, and what you have always postponed. List the people you want more time with. You do not need a five-year plan. As the Preferment course page puts it, you just need a room to start figuring it out in.
Read this answer in the FAQHow this guide was written
This guide was written by Rarified Life using the facts Rarified Life publishes about its own programs and the published sources cited on the page. Statistics are quoted as published with their sources. Rarified Life offers retirement coaching, so this is not an independent review.
Read more about how Rarified Life writes these guides or visit the Rarified Life website.