The Cold Reality Old Money Knows Only Too Well

I’ve been lucky enough to have witnessed several rags-to-riches and, well, penny loafers-to-riches stories in recent years. Friends and colleagues have worked hard and done well, and I couldn’t be happier for them.

Unfortunately, and sometimes shockingly, some of their other friends and family members have not been happy to see their success. And, to those who’ve believed, invested, risked, and won, it’s painful. I’ve put my arm around more than one tough-as-nails entrepreneur as he (and she) fought back tears after being stung by petty jealousy and bitterness: family members or (so-called) friends who did some moronic mental math–you won, so I must have lost, or something to that effect, and couldn’t manage a smile and congratulations.

It’s made for some incredibly uncomfortable gatherings, whether it’s in the backyard, the pub, or the country club. Old Money knows this all too well. Some people aren’t happy you have it, whether you’ve made it, or inherited it, or a little of both.

So what do you do when you have a big payday? In private, feel free to pump your fist in the air and scream at the top of your lungs in your own living room (remember the neighbors. Wink, nod.). Dance in your underwear and spew champagne. Celebrate. Be joyful. You’ve earned it.

In public, be discreet. Don’t brag. Avoid bling. Shift the conversation away from yourself. Ask others what’s new with them. Make every attempt in public to act like nothing has changed. Be slow to acquire new material possessions. If you buy new clothes, make sure they whisper Quality and don’t scream New Money. (If you’ve inherited your new-found wealth, don’t say a word about it to anyone. It’s not your place, since you didn’t earn it.)

And now, take stock of how you’re going to share your good news, and with whom, and when…or if at all. Remember, one of the most flattering comments someone can ever make about you is: “Wow. I didn’t know he had that much money.”

Inevitably, people you’ve confided in will spill the beans, despite the best of intentions and the most solemn of oaths. They’re human. Forgive them. Expectations and requests will be put forth, either subtly or boldly, when others find out. Part of your evolution will be in learning to handle these as diplomatically and effectively as you’ve handled your challenges in the business world.

And if you’re ever at a loss, you can always reach out to me. Been there, done that, and, in this regard, not much I haven’t seen.







4 thoughts on “The Cold Reality Old Money Knows Only Too Well

  1. Good points. If we ever had any sort of windfall, I know we’d go to great pains to hide it from everyone we knew. Not only do you open yourself up to the petty jealousy you’ve outlined, but also those pretending to be your friends looking for favors, and lawsuits of whatever flavor.

  2. Very good post and important words of warning. My husband and I live comfortably but far below our means. Very few people have any idea that we have any money. The few times I have tipped my hand I have regretted it. I have learned to think of the budget we have set for ourselves as all the money that we have. That’s how I think, that’s how I live, that’s all anybody needs to know.

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