The Greatest Generation AKA The IDGAF Generation

I never caught his name, we were too busy bullshitting the whole time. But the conversation started when he finished pouring his cup of free car dealership coffee and said something like, "In my business, I deal with a lot of very average people." He was definitely directing the comment to me inviting a conversation. This was a dealership for expensive cars. He was of a generation of people that assumes that wealth always accompanies effort and intelligence. He was wrongly assuming the best of me.

So he says he deals with a lot of idiots, and I tell him I have a good friend who always reminds me, "Mitchell, try to be patient. Try to keep in mind that half of the people in the world are below average." That one always gets a belly laugh when delivered with the right timing. My new octogenarian friend liked the joke, so we kept talking.

He asked if I was working. I had my laptop open and I was logged in to a server fixing some API integration bugs as usual. He said these days you can work from anywhere so you end up working from everywhere, all the time. I asked him what sort of business he was in and he said he owned an insurance agency. He said he had 10,000 clients active on his roster. He was wealthy. He was wealthy in a way that I found very inspiring and interesting.

He said he started his business with a handful of clients. He said he always loved to hustle. He said when he first started out he would sell a policy to anyone. He didn't care. He had and still has an IDGAF attitude. This is what inspired me. He had an attitude and a comportment that signaled that he was never embarrassed to ask for someone's business. He was never too proud to go out and start over if one of his risky ventures blew up. He was always on the hustle, making money, making deals and serving people.

This gentleman kept saying Christ over and over again. It was his form of punctuation. Instead of commas he said 'Christ!' Like, "Christ man! I mortgaged my house like three times just so I could buy more property! Christ! What else am I going to do? What's the worst that can happen?" I bring this up to help emphasize a point about this man. He had grit. He was tough. He was the kind of tough that you want to be. He was not tough like a stone wall. He was tough like a reed or a willow branch. He was mentally resilient, sprightly and lithe. He could always bounce back. He had little fear because he had grown up in the worst of times.

He, like my grandmother, was a product of the Great Depression. He was part of a generation who had a much more immediate connection to the destitution and ruin that lurks around the corner. He told me story after story of business risks he had taken in his 50 years of working life. His explanation for how he reasoned his way into the risk was always grounded in IDGAF. "What's the worst that can happen? I mortgage my house to invest in a new condo development. It goes belly up. I lose everything. I just go and hustle the business again like I always do."

I told him the story of how my grandmother raised three girls on her own, making a living as a nurse and a seamstress. I told him that she had the kind of grit that he has. This came up because he was saying that he thinks the country is getting soft and getting depraved. He thought that we were losing our way and forgetting how to buck up and get shit done. I told him that I had been watching that carefully lately and that I disagreed. I told him that his and my grandmother's qualities were part of the American DNA from what I had seen. We may eat too many burgers, get fat and slow from time to time, but there's still a tidy cross section of America who can crank up Eye of the Tiger, lose the pounds, get back into fighting shape. We can still get our head back in the game and hustle a win. I don't know if he agreed or if he was just entertained by how I deliver most of my rants to strangers.

We talked about his retirement. It doesn't exist. His idea of a round of relaxing golf is to write another million dollar check for another real estate venture and then go shake the tree to find another business opportunity. He had been hustling for so long, putting so much distance between himself and the imminent starvation facing his Depression generation memories that he couldn't really slow down. He was still having fun.

I was really inspired by this guy. He built up his financial success very slowly and gradually over time. He combined grit, courage, resilience and intelligence into a uniquely American package. His swagger was a critical part of his success. He threw himself at life, unafraid of a bruise or a fat lip. He still had bounce and hustle after all those years.

Perhaps the best part was that he was secretly Buddhist in his attitude. He was not attached to his wealth. It was a source of adventure for him. He told me that he could still live on $10,000 a year if he needed to. So he DGAF! He cared more about the hustle than about the money.

I wished I would have caught his name. He split though. He left in a hurry. He left right about the time he thought I was about to try to sell him something.

Sign up for MORE Solspace

No nonsense. No spam. Just useful free tips, insights, guides, resources and stories.