Reflective Questions for Funding a Good Life
Use structured reflection to plan retirement around happiness, not just a number
Most retirement planning starts with 'what do you want to retire with?' and works backward to a savings number. Felix argues that's the wrong front door. The same dollars produce wildly different happiness depending on adaptation, satiation points, the end-of-history illusion, and the gap between imagined and minute-to-minute reality. Plans that ignore those frictions fund a number that doesn't actually buy the life.
The framework is a set of reflective questions, structured into sections (circumstances and adaptation, income satiation, work and leisure, values change), used inside the planning conversation. Each section gives the client and adviser a way to test whether a stated goal will actually deliver the imagined outcome. Felix wrote it up as the paper 'Finding and Funding a Good Life' after a year-long engagement with Brian Portnoy.
The value is twofold: it surfaces the bad trade-offs (the cottage you'll dread driving to, the toy that'll sit in a box, the salary increase that'll vanish into a bigger garden) and it changes adviser meetings from spreadsheet reviews into trade-off conversations.
- Adaptation erodes the happiness boost from most major purchases.
- More money raises happiness on a log scale, but trade-offs change the calculus.
- People underestimate how much they'll change in the next decade (end-of-history illusion).
- Imagined uses of money differ wildly from minute-to-minute reality.
- Good planning frames trade-offs; clients still make the calls.
- Section 1 — Circumstances and adaptationAsk clients to reflect on past major purchases that were supposed to make them happier. Did they? What about the minute-to-minute reality of the cottage, the bigger house, the boat? Adaptation usually wins.Pro tipUse this with kids too — 'remember the toy you really wanted? Do you play with it now?' Felix uses it on his own children.
- Section 2 — Income satiationAsk: 'How would your life change if you earned an extra $1,000 per month? What would you spend it on?' The answer separates marginal-utility-rich uses (a child's bedroom) from low-utility uses (a second Lamborghini).
- Section 3 — Work and leisure trade-offsAsk: 'Would you work an extra three hours per day for more money?' and 'How much would you need to be paid to give up your favourite leisure activity?' These surface what the marginal hour and marginal hobby are actually worth.WarningWatch for 'no amount of money' answers — they're a strong signal about what really matters and what shouldn't be traded off.
- Section 4 — Values and timeAsk: 'Have your values and preferences changed in the last decade? Do you expect them to change in the next?' This breaks the end-of-history illusion that drives over-aggressive sacrifices today.Pro tipUse parents as reference: 'How did they change between 50 and 70?'
- Run the planning numbers against the answersTranslate the reflective answers into plan inputs — target lifestyle, working years, big-purchase decisions. The plan now hangs off real preferences, not a generic dollar target.
- Revisit annually as a soft layerRe-run a subset of the questions each year. People's answers drift — that's the point. The plan should drift with them rather than calcify around the original target.
Felix walks clients through the cottage purchase question. Most imagine grandkids and summer memories; the reflective question forces them to picture the 2-hour drive, kids spilling drinks, winter pipe-bursts.
When his children ask for a new toy, he asks them about a previous toy they really wanted. They admit it now sits in a box. He asks if the new toy will end the same way; they often agree.
Felix wrote up the framework as 'Finding and Funding a Good Life'. Despite expecting little impact, it became the most-downloaded paper on PWL's website for years and reshaped client meetings.
Felix's firm engaged Brian Portnoy, author of The Geometry of Wealth, for a year of work with their financial planners on softer skills. Felix initially resisted — 'why are we giving people advice not specifically related to finances?' — then realised the gap between funding a number and funding a life. To make the insight actionable he distilled academic papers and books into a short paper with reflective questions at the end of each section. It became the most-downloaded paper on PWL's website.