White paper
Built for a Buyer,
Retiring as a Seller
The skill that built your wealth is a buyer’s skill. The day you retire, you become a seller.
You know exactly how you would handle a 2008 while you are still working: hold, and buy more. Do you know, to the dollar, how you would handle one while you are living off the money instead of adding to it?
Nothing about the market changes when you retire. You do.
For thirty years you were a buyer. A crash was a gift: you bought the same shares on sale. The day you live off the portfolio, you become a seller for the first time in your life. Now a crash means selling at the bottom to pay for your life. Same market, opposite result.
The market did fine. Only the timing was different, and that is the one thing you do not get to choose.
For you, the danger was never running out.
People like you almost never go broke. The affluent tend to die with most of their money untouched. The danger was never the empty account. It is reaching the end with more than you started, having spent your one good decade braced for a disaster that never came for you.
You get the recovery. You do not get the years.
The fix
It isn’t to get conservative. It’s to sequence the risk.
You earned your edge and you do not have to surrender it. Protect the income and the years you cannot afford to gamble, so a bear becomes background noise again. Then stay as aggressive as you like above that line. Not less ambition. Ambition in the right order.
So, do you know, to the dollar, how you would handle the next 2008? If the answer is “not yet,” that is the hour worth spending. Thirty minutes with Jun. No products, no pitch.
Sources: Kitces & Pfau (2014, 2015); Morningstar “State of Retirement Income” (2024, 2026); Blanchett (2014); Banerjee (EBRI, 2018); S&P 500 total return (Shiller). Figures illustrative.