The Talk - Part 3

Dec 19, 2025

One of the recurring themes of these posts (and life) is Harder Now, Easier Later or Easier Now, Harder Later. You get to choose, but the bill always comes due. It would be neat if life wasn’t like this, but that’s like wishing the sun rose in the west and set in the east.

I’ve been enjoying @KurtSupeCPA‘s posts on X. They are real, relatable, and a good warning for families who choose the Easier Now, Harder Later path by not having The Talk between generations around estate planning, retirement, and inheritance. A recent post did not disappoint, in part noting:

Because here's what nobody talks about:

Your kids watched you clip coupons for 30 years. They watched you skip vacations to max out your 401k. They watched you say 'we can't afford that' a thousand times.

Now they're doing math in their heads. And that math includes YOUR money.

AND NOBODY WANTS TO HAVE THAT DISCUSSION

So here's my advice: Have it anyway. Earlier rather than later.

Because your retirement plan shouldn't come with guilt.

And their expectations shouldn't come with assumptions.

Mom and Dad won at the Game of Life. Mazel! Go enjoy it, it’s your money! You earned it, ride off into the sunset however you want. That said, please make sure the paperwork (will, trust, POAs, etc) are perfect. Being lazy or forgetful or avoiding this critical yet mundane part of adulting could have dramatic consequences for your family.

There is $85T of wealth about to pass to the Next Generation. Without proper planning and paperwork, only the tax man, the lawyers, and the government will win, not the families. Mom and Dad, this is about the process, not the amounts. Let’s all help ourselves move our families forward