Financial Autopilot vs. Hands-On Investing: How to Choose the Right Balance

Last week, I sat in on one of my son’s classes, and they were discussing the trolley problem - that well-known ethical dilemma where you have to decide whether to let a runaway trolley continue on its path and hit five people, or deliberately pull a lever to switch tracks and hit just one.

The conversation got even more interesting when they applied it to self-driving cars.

For instance, if a large object falls off the truck in front of you, what should the self-driving car be programmed to do?

Hit the object and risk the passengers?

Swerve and hit the bicyclist to the right?

Or hit the minivan full of kids to the left?

It’s unsettling when you realize that we’re programming machines to make moral choices.

Oftentimes we do something kind of similar with our money.

We’re all deciding, in one way or another, how much control we want to have and how much we’re comfortable outsourcing.

Some people want to hand things off completely. They’ve got financial advisors, robo-investing apps, index ETFs, and/or Limited Partnership (LP) passive investments - the whole “self-driving” setup. Their investments just hum along with little input from the owner, and they like it that way.

Others want their hands firmly on the wheel. They want to understand every investment, every tax move, every turn their money takes. They’re not about to trust an algorithm to steer their future.

And honestly? Both approaches are totally fine.

Letting your finances “drive themselves” can make life simpler and help you stay consistent when markets get bumpy. But it also means trusting someone (or something) else’s definition of “the right path.”

Even investing in an S&P 500 ETF (which can be an easy and great financial move!) means you may be supporting people and behaviors that you don’t morally agree with.

Taking full control gives you freedom, but it can also feel like a lot of pressure when you’re the one making every call. (And every year when I’m about 100 pages into my 400-page tax return, I wonder why I keep doing this to myself!)

I recently wrote about my cabin dilemma (whether to sell at a big loss) and honestly, it feels a lot harder when I’m the one behind the wheel. Earlier this year, I also lost money as a Limited Partner in a commercial real estate deal, but at least there I could blame someone else for the timing, management, and decisions. With the cabin, though, every decision (and every dollar) is mine. I jokingly think that I should just put up two signs in the road - Keep and Sell - and let the next Waymo that passes choose which one to hit!

But the real secret I think is in finding your balance. Maybe your retirement savings run on autopilot, but you make the big strategic decisions yourself - when to invest, when to slow down, and what kind of life you actually want to build.

Maybe you invest in the S&P 500 ETF, but you also allocate a small portion of your investments to women-owned businesses. Or you leave your retirement in a Target-date Fund but take more control over your taxable brokerage account. Or split your real estate investments between personal investment properties and LP passive syndication investments.

In the end, wealth isn’t about control - it’s about confidence. The confidence that no matter if it’s you or the self-driving car who’s steering, you feel good about the decisions being made and where your life is headed.

If you’re ready to take back the wheel - or just want to make sure your financial autopilot is headed in the right direction - check out our Wealth by Design course. It’ll help you build a financial system that actually reflects your values (no AI required).