What I Learned Too Late: AI for Family Decisions That Matter

Why strategic thinking beats information gathering when family relationships are on the line.

Look, I'm not going to sugarcoat this.

In 2018, my mother called needing help.

We hadn't been close—just occasional, strained conversations over the years.

Part of me wanted to say I couldn't do it. That I didn't have the bandwidth to step back into years of tension, anxiety, and unresolved history.

But something in me said no. Maybe it was the cultural expectation—my mother was Japanese, and in our family, you respect your elders whether or not things have been perfect. Maybe it was something deeper.

So I booked a flight for the next day. My wife was surprised I didn't say no—and honestly, so was I.

⸻

What I Didn't Expect

What I didn't expect was how fast everything would happen—and how unprepared I'd be despite thinking I knew how to solve complex problems.

Most families get months to adjust between phases of decline. I got weeks.

She had been living alone for nearly 20 years since my dad passed, never drove, and had become completely dependent on me for everything outside the house. She didn't want a caretaker, refused assisted care, and was determined to stay in her house.

In five months, we went from "okay, let's modify the house for safety and get her a walker" to medical bed, to assisted care, to hospice, to closing everything down.

Each week brought a different crisis that other families typically have months to navigate.

⸻

The Research Trap

I did what any responsible adult child would do: I researched everything.

Googled "aging parent care," read dozens of articles, called everyone I knew who'd been through it. I had spreadsheets comparing assisted living facilities and Medicare guides covering my kitchen table.

Here's the thing though—all that information didn't help me navigate the real problem: how to talk to my mother about her declining independence without making our already fragile relationship worse.

One example: My mother became convinced my sister was financially abusing her. Given her anxiety and some confusing bank statements, I felt like I had to take this seriously.

So I did what felt responsible: hired forensic accountants, consulted attorneys, even brought in my CPA wife to review every transaction.

Months later, and after spending over $15,000 trying to get clarity, the conclusion was: no criminal case. Just confusion from medication side effects and normal anxiety about losing control.

Looking back, all that investigation could have been replaced by conversations that addressed my mother's real fear—feeling powerless—while keeping the family together.

I was doing everything "right" according to the advice I found online. But I was treating a relationship problem like a business problem that needed data and escalation.

⸻

Fast Forward to 2023

As we exited COVID, my father-in-law started declining.

My wife and I thought we had this figured out. I'd been through it before, right? Plus, this situation seemed more manageable—he was local (though an hour drive), and my wife's sister lived five minutes from him. We had family support, better logistics, lessons learned.

Turned out, different people means different everything. Different personalities, different medical issues, different family politics.

Everything I thought I'd learned didn't apply.

But here's what was different: by 2023, I'd been using AI strategically for business decisions. Not just "write me an email," but actually thinking through complex problems with multiple stakeholders and competing interests.

And something clicked—why wasn't I using this same strategic thinking approach for family decisions?

⸻

What I Learned About Strategic Thinking

Instead of asking generic questions:

How do I talk to my aging parent about driving safety?

…and getting generic answers, I started giving AI real context:

My father-in-law values independence above everything. My wife feels guilty about limiting his autonomy but is terrified something will happen. Her sister tends to avoid hard conversations. Help me think through how to approach this so we can make progress without everyone getting defensive.

It was a completely different kind of response.

One that actually felt useful.

The key was treating family decisions as strategic thinking problems—not just information problems.

⸻

Why Templates Don't Work for Families

Templates work fine for business tasks: writing emails, creating plans, summarizing data.

But family decisions aren't template problems.

Your dad isn't a generic "aging adult." He has specific triggers, communication patterns, decades of history with you. Your siblings aren't just "family members"—they're individuals with their own guilt, fears, and ways of avoiding conflict.

When I started providing context—personalities, history, what usually works and what definitely doesn't—AI became genuinely helpful.

Better conversations. Less drama. Decisions that actually stuck.

⸻

The Thing I Can't Change

I can't go back and handle my mother's situation differently.

But I can tell you that when family relationships are on the line, thinking strategically beats reacting to each crisis as it comes.

Because the decisions that matter most aren't just about finding the right information—they're about navigating relationships when everyone's stressed and scared.

And getting them wrong doesn't just mean inefficiency. It can mean damaged relationships that don't recover, expensive mistakes that seemed necessary at the time, and months of stress when time together was what mattered most.

That $15,000 investigation wasn't just wasted money. It was lost time when my mother needed care, not investigation. It was family relationships damaged by suspicion. It was my mother's dignity affected by a process that felt like we didn't trust her concerns.

All because I reacted to her fear with investigation instead of thinking strategically about what she really needed.

⸻

What's Next

If you're dealing with family decisions that feel bigger than any advice column can cover, you're not alone.

I'm sharing more about this approach—how to combine strategic thinking and AI to make decisions you can feel at peace with, even when they're difficult.

⸻

P.S. : I'm working on a course to help you apply this same approach—combining strategic thinking and AI—to make clearer family decisions with less stress and more confidence.

If you'd like early access (and early-bird pricing), you can join the waitlist here:

👉 Join the Waitlist

If you’re dealing with complex family decisions and feeling like generic advice isn’t cutting it, you’re not alone. I’m working on better approaches to this stuff. Subscribe here if you’d like to stay in the loop.