First Wins: What We Actually Felt Good At

Everyone remembers that first time you thought, “Hey, I’m actually good at this!” For Tom, it was falling into a work groove, whether he was pushing carts in the grocery store or working the farm. Routine made it feel easy, or at least doable.

Shirley cracked me up: her first “skill” was just smiling at people. She said it helped her out with business and even came in handy on the side of the road with a flat tire! Later on she got really good at bookkeeping, a skill she took major pride in. For Kim, it was learning to scoop the perfect ball of ice cream in sixth grade. (I get it: service jobs teach you a lot about hustle and being quick on your feet.)

Me? I always found confidence in doing the simple stuff well, ringing up groceries, handling payroll, until those “small” wins started to add up.

That First House: What Could You Actually Afford?

This part of our chat had everyone laughing and shaking their heads. Tom and Shirley remembered buying their first home, a finished basement for $5,000, then a whole house for $16,000 in the 60s! Their payment was $111 a month, but fun fact, their weekly income was only like $110. The bank nearly wouldn’t lend them the money because they were $11 short on the paperwork, which just sounds wild today.

Kim bought her first house for $30,000 in 1984, and her payment started high ($250 a month) and actually dropped as her interest rate went down. My first house in 1986 was $45,000, with a $365 mortgage at 9.5% interest (which somehow felt “normal” back then). And we always had to put 20% down, no exceptions, no first-time buyer deals.

Sure, prices sound cheap now, but our paychecks matched the times. Back then, my $400/week felt like a solid gig running a grocery store; now that same job pays way more.

The Fun Stuff: Gas, Groceries, Candy Bars

Some of the memories that came up were kinda hilarious. Like, Tom paid 19 cents for a gallon of gas at one point, and Shirley swears there were “gas wars” with prices down to nine cents! When Kim and I started driving, gas hovered around a buck thirty, and it just kind of stayed there forever. These days? I wish, it’s $2.30 to almost $3.00, depending on where you live.

Groceries were another level. Back in the 60s, spending $10 a week to feed everyone was tough—they’d actually try to hit $10 just to get enough Green Stamps for a bonus! A loaf of bread was maybe 20 or 30 cents, a candy bar was a nickel or a dime, and penny candy was everywhere. It sounds unreal but, yeah, a buck actually meant something.

How All That Money Stuff Changes Your Plans

We wrapped it up talking about how inflation, price jumps, and rising wages totally mess with your business or career goals. Years ago, $50,000 was big money, now, not so much. And a $10,000-a-year side business once bought you two new cars. If only.

Here’s the rub: When prices go up, they mostly stay up. Gas and food might bounce, but your basics - homes, cars, salaries - they don’t drop back. What counts as a “good income” today would have been king-size years past. So you always have to ask, “Does this gig still work for my life?”

We All Start Out Basic…And That’s OK

So what’s the lesson in all those old stories? Nobody starts out in a perfect house or job. People build up little by little. Whether it’s your first home, your first real paycheck, or just your first sense of being “good at something,” every family has their own road. The numbers might change, but the effort and learning don’t.

Hope you liked these stories. Check out episode 76 right here!