In thirty-eight years of selling real estate, I never once had a regular paycheck.
That’s not a complaint. It’s just how the business works. There were stretches — sixty days, sometimes ninety — with no income at all. And then, if I was fortunate, a single closing on a higher-priced home would land and the dry spell would be forgotten overnight. That was the rhythm of my working life: feast, famine, feast again. I built an entire career, raised a family, and never once knew with certainty what the next ninety days would bring.
I assumed, when people talked about the psychological adjustment of retirement, that it was about losing a regular paycheck. I didn’t have one to lose. What I’ve actually had to adjust to is something almost the opposite, and nobody warned me about it.
The Ghost Commission
What disappeared wasn’t predictability. I never had that. What disappeared was upside — the possibility that the next ninety days could produce something extraordinary. In real estate, you live with uncertainty, but you also live with hope of a particular kind: the lottery-ticket hope that the next deal, the next closing, the next client, could change everything. Even in the leanest months, that possibility was always technically still alive.
Fixed income doesn’t work that way. Social Security and the modest other income Bonnie and I rely on now arrive exactly on schedule, exactly the same amount, month after month. There is a real comfort in that predictability, and I don’t want to undersell it. But there is also something quietly strange about losing the chance for a windfall after thirty-eight years of structuring your entire identity around the possibility of one.
I think most men coming out of careers with genuine upside — sales, entrepreneurship, commission-based work of any kind — feel some version of this, even if they’ve never named it. It isn’t about the amount of money. It’s about the disappearance of possibility itself.
It isn’t about the amount of money. It’s about the disappearance of possibility itself.
Why I'm Betting Again
Here is what I haven’t said publicly until now: I am three years into building The Encore Project without taking any income from it. I’ve spent meaningful savings developing it. It may be another year or two before that changes.
If you are considering something similar — starting a business after retirement, whether out of necessity, restlessness, or a long-deferred dream — I want you to know two things before you decide whether the risk makes sense.
The first is that the odds are far better than conventional wisdom suggests. Research has found that entrepreneurs who start a business at fifty are twice as likely to succeed than those who start in their thirties, and that probability of solid profitability continues to climb with age after that. Nearly a quarter of new businesses in recent years were launched by founders between fifty-five and sixty-four — up significantly from just fifteen percent two decades ago. More than half of small businesses in this country are now owned by people fifty-five and older. This is not a fringe activity for restless retirees. It is, statistically, one of the strongest windows of entrepreneurial success in a person’s life, precisely because decades of judgment, networks, and hard-won expertise are not liabilities at this age. They are the advantage.
The second thing I want you to know is more personal, and it’s why I’m doing this anyway, knowing the numbers don’t guarantee anything. The Encore Project has become, in a very real sense, my new version of waiting for the big closing — except the paydays, if they come, won’t arrive every three or four months the way they sometimes did in real estate. This is a longer, slower bet. What keeps me at it isn’t blind optimism. It’s confidence that there is real demand for content that offers men our age genuine hope and inspiration, delivered with honesty rather than the generic, algorithm-chasing material that dominates so much of what’s published for this audience. If that confidence is correct, the eventual payoff could make any single real estate commission I ever earned look small by comparison.
I don’t say this to boast. I say it because I think there’s real value in naming what it actually feels like to step away from a volatile income you understood completely and into an even less certain bet on something brand new — at an age when conventional wisdom says you should be reducing risk, not increasing it. The data suggests that wisdom may be backward. The risk, it turns out, may be smaller than it looks, and the advantage may be larger than anyone tells you.
The Discipline of Delaying
One piece of financial strategy I do think every man in a similar position should understand, whether or not he’s building something new: the decision of when to claim Social Security is far more consequential than most men realize, and it is one of the few truly controllable levers left in retirement income.
Delaying your claim from full retirement age to age seventy can increase your monthly benefit by up to 24 percent for the rest of your life. For a married couple, the math becomes even more significant: when the higher-earning spouse delays claiming until seventy, it doesn’t just maximize that one benefit — it also maximizes the survivor benefit the remaining spouse will receive for the rest of her life. In practical terms, this means a man’s decision about Social Security timing can function as a final, deliberate act of financial protection for his wife, executed years or even decades before either of them might need it.
This isn’t a decision to make casually or alone. Health, other income sources, and life expectancy all factor in. But too many men treat the claiming age as a formality rather than what it actually is: one of the most powerful financial decisions available to them, requiring nothing more than patience.
A man’s decision about Social Security timing can function as a final, deliberate act of financial protection for his wife.
The New Vulnerability
There’s a harder truth I think men our age need to hear plainly, because it directly threatens everything else discussed here: we have become the primary target of financial fraud in this country, and the numbers are not improving.
Adults sixty and older reported losing more than seven billion dollars to scams in a recent year alone — a roughly sixty percent increase from the year before. Investment fraud and impersonation scams, often involving someone posing as a bank, a government agency, or even a family member in distress, account for the largest losses. And the bitter irony, confirmed by federal regulators who study this closely, is that scammers don’t primarily target confusion or weakness. They target confidence. They target the decisive problem-solver in the family, the one who handles things, because that exact instinct — the urge to act quickly and fix the threat himself — is precisely what the scam is designed to exploit.
I don’t have a tidy solution to offer here beyond this: the instinct to handle it yourself, immediately, without checking with anyone else, is no longer a reliable signal of strength. In this particular arena, slowing down and asking someone you trust before acting is the more capable move, not the weaker one.
What I Want You to Take From This
If you spent your working life on commission, in sales, running a business, or in any career where the next big payday was always theoretically possible — and you’re now living on a fixed income that, for the first time, forecloses that possibility — I want you to know that the strange grief you might feel about that isn’t really about money. It’s about identity. It’s worth naming honestly rather than pretending the only adjustment retirement requires is learning to live on less.
And if, like me, you’ve decided that fixed income isn’t the end of the story — that there’s one more bet worth making, even at this stage, even without certainty — the numbers are actually on your side, even if the outcome is never guaranteed. It is not reckless. It is simply a man who spent decades comfortable with uncertainty, choosing to be uncertain one more time, for something he believes in.
