There is no single formula for retiring well, and anyone who sells you one is selling you their retirement rather than yours. But there are patterns. Chris closes his pre-retirement program with this list, and it is the part people photograph.
Read it as a diagnostic rather than a to-do list. The useful question at each one is not have I done this? but who is helping me with this, and when am I starting?
1. You have found your next purpose
Not a hobby. A reason the day needs you in it. It might be a grandchild, a cause, a craft you intend to get genuinely good at, a business, a classroom, or a board. What matters is that it would be noticed if you stopped — by someone, including yourself.
Purpose almost never arrives by waiting. It arrives by trying things, which is why curiosity sits at number three and why the Curious List is usually the first piece of work a client does.
2. You have replaced your work identity
For most of a working life, the answer to what do you do? did a great deal of quiet labour. It told strangers how to place you, told you where you stood, and carried a whole set of assumptions about competence and worth. Handing back the badge hands back all of it.
People who transition well have built a new answer before they needed it. Not a smaller answer, and not a defensive one — a true one. The test is simple: at a party, when someone asks what you do, does your answer feel like a description or like an apology?
3. You are curious, and willing to explore
This is the single best predictor Chris sees. Curiosity keeps you learning, and learning keeps you meeting people, and meeting people keeps you curious. It is a loop, and it runs in both directions — which is exactly why curiosity and connection are worked on together rather than separately.
Willingness matters as much as curiosity. Plenty of people can list ten things they are interested in and have walked into none of the rooms where those things happen. The willingness to be the new person, briefly and slightly uncomfortably, is the skill that unlocks the rest.
4. Your time is filled with things that mean something
Filled, not merely occupied. An empty calendar and an over-full one can both be symptoms of the same problem: no criteria for deciding what belongs in it.
The people who do this well tend to have a rough shape to the week rather than a rigid schedule — something in the mornings, a couple of fixed commitments involving other humans, and real space that is genuinely theirs. The shape is what turns free time into rhythm.
An open calendar sounds like freedom until you live it. Rhythm is what makes the freedom usable.
5. You stay connected, and you stay relevant
Connection is the obvious half and relevance is the half people miss. Staying relevant means remaining part of the current conversation — in your field, your community, your family, and in the technology everyone around you is using to organise their lives.
That last one is not a small point, and Chris asks about it directly at intake. If the people you care about arrange their lives through phones and messages and shared calendars and you have opted out of all of it, you will find yourself further outside the loop each year, through no fault of your own warmth. Staying fluent enough to keep up is a connection strategy, not a technical one.
6. You keep mentally fit and physically active
You may be planning for thirty or forty more years. Everything else on this list runs on the body and mind that have to carry them, which is why the Wellness Review is one of the three core activities.
People know this one. What they usually lack is not information but a plan they would actually keep, and someone to say it out loud to. Two specific commitments beat ten aspirational ones.
7. You feel financially secure
Feel is the operative word, and it is doing real work in that sentence. Chris does not give financial advice — that seat belongs to an advisor. But feeling secure is a different question from being secure, and it is squarely a coaching question.
Plenty of people with sufficient assets still feel precarious, because nobody has ever walked them through what the money is actually for. Plenty of others have never asked the question at all. Either way, the work is making sure the question reaches the right chair, with the right questions attached, and that you follow through — which is what the crew around you is for.
8. For couples: time together, and time apart
For better or for worse — but rarely for lunch, every day, for twenty years. Two people who spent three decades coordinating logistics across two full working lives may never have had the conversation about what each of them wants the next twenty years to look like.
Couples who do well name both halves explicitly: the things that are ours, and the things that are mine. Both lists need to exist. When only one of them does, it usually shows up within the first six months.
This is why couples sessions run a full ninety minutes. Two Next Chapters take more room than one.
9. You are looking at the transitions still ahead
Retirement is not the last transition. It is the one that buys you the vantage point to see the rest coming: ageing parents, your own health, a move, the loss of people you counted on, changes in what you are able to do and want to do.
This is not morbid. It is the difference between deciding in advance and deciding in a crisis. The people who look up the road are the ones who still have choices when it arrives — which is the whole argument for planning any of this early.
Where to start
Read the nine again and one of them will feel more uncomfortable than the others. That is the one to start on, and it is almost never the one you would have guessed before you read the list.
Take the Pre-Retirement Quiz if you want a sharper read on it, or take a look at how the coaching process actually works — the nine marks map fairly directly onto the arc of the sessions.
What Chris recommends reading
- Retirement Intelligence: Personal Retirement Readiness — Robert Laura. The most direct treatment of the non-financial side.
- Keep Sharp — Sanjay Gupta, MD. On staying mentally fit for the long horizon.
- The Blue Zones — Dan Buettner. What the longest-lived communities have in common, and how much of it is connection. The Netflix series Live to 100 covers the same ground if you would rather watch it.
- Modern Elder Academy — meawisdom.com. Programs built around the midlife and later-life transition.
- AARP — aarp.org. Broad, practical, and free.
- Next Chapter Notes — Chris's own monthly newsletter, if you would like one short thing to read each month instead of a book.
The nine marks and the reading list are drawn from Chris's Retirement Reimagined pre-retirement program, delivered to organizations and their employees.