My “Dark Side” of Generosity: How I’m Curbing it in Retirement.

I’ve always had a bit of a dark side, one I never really tried to control and certainly didn’t think of as a problem. This was especially true when I ran my own business. Through sheer effort and hard work, that business threw off a lot of free cash flow. With all that cash sloshing around, I christened my peculiar habit: Random Spontaneous Generosity (RSG).

RSG would manifest in unpredictable ways, at random times. For instance, I was walking past the pay station at a restaurant after a dinner I was attending and, on a complete whim, decided to pay for the entire 30-person seated dinner. Another time, I promised a friend’s daughter ownership of one of my (admittedly older) cars if she passed her driving test on the first attempt—and yes, I carried through on that promise. I even remember filling a person’s heating oil tank when I found out they couldn’t afford oil during a cold snap. The list, believe me, goes on.

I should quickly add, all this was in addition to every single one of my own expenses, investment goals, and savings being fully met and funded. I accept that this generosity stemmed from a place of reasonable abundance. But now, since I’m retired and drawing from my portfolio and fixed income, I’ve had to face facts: I need to stop doing it. At least to the same degree.

The simple key to control in many situations, I’ve found, is recognition. Once I understood the beast, I could start to tame it. I’ve since implemented a few simple protocols to manage my self-named RSG issue, creating a layered defense system. Sounds technical doesn’t it?

My first line of defense is, ironically enough, a line itself. This line lives in my expenses spreadsheet under “discretionary generosity.” Once this monthly allocation is depleted, that’s it. I have to play hardball with myself; the well’s dry until next month.

My second defense measure is a 24-hour cooling-off period. Before making any sudden offers of help or grand gestures, I force myself to wait a full day. This pause gives me time to properly consider the decision and its implications, rather than just acting on an impulse.

But my third, and frankly, most solid line of defense is my wife, Suzie. Now, before any RSG urgings can take hold, I run them through the “wife filter” before I commit to anything. Just for laughs, I’ve even put Suzie’s number on speed dial, because you never know I might get the urge when ordering a Guinness in a crowded bar!

It feels good to have these boundaries in place. It means I can still be the generous person I am, but in a way that’s eminently more sensible, and at the very least, it’s going to stop my friends’ delight in exaggerating my past hair-brained gestures even further from reality.