Financial Planning Lessons from I-95 | Old Peak Finance

What a Drive Down I-95 Reveals About Smart Financial Planning

January 15, 2026

Financial planning lessons from I-95 illustrated by a highway billboard

What a Drive Down I-95 Reveals About Smart Financial Planning

January 15, 2026

I have had reason to spend time driving on I-95, one of the busiest highways in the US. It occurred to me you can learn a lot that’s relevant to your finances.

You might expect me to write something like: “there’s a ton of traffic, so the economy must be strong”, or “there’s a ton of construction, so that’s good for our national infrastructure but maybe hard on government finances”, or “I should buy more Amazon stock since every third truck I see has their logo.”

But I suspect those observations would not come as a surprise.

Instead, I want to raise something you would surely notice but might not connect to your financial plan. It’s the dozens of highway billboards offering one particular service: legal help if you have been injured, whether on the job or in your vehicle.

My point: check your liability insurance coverage.

If you have any meaningful assets apart from your primary home and retirement accounts, you need liability insurance. Most auto and home insurance policies have some coverage. But it’s never more than $500,000, and often less. That means most people reading this need an excess liability insurance policy, also known as umbrella insurance. Policies are sold in $1 mm increments and are typically inexpensive: $100-250 annually per $1 mm of coverage. You typically buy it from your primary insurance carrier; sometimes, they will find a third-party insurer for you. Most people should have a policy equal to the amount of your unprotected assets: bank and brokerage accounts plus other assets like a second home. People with a high and predictable income (doctors, for example) are theoretically at risk of the plaintiff garnishing their future income. That would argue for even more umbrella coverage.

Now put yourself in the shoes of one of the lawyers with their faces plastered over these billboards. Their first job is to get hired. Their second job is figure out if the defendant has any assets and to sue to get as much as they can. They are working on a contingency basis and will get a percentage of the settlement – so they have every incentive to ask for a lot. But the lawyer’s third job is to wrap the case up quickly and move onto the next client. The win-win: grab the umbrella policy payout. Fast, and a lot less painful for everyone but the insurer.

If it makes sense for all these attorneys to spend all this money on highway billboards, it has to make sense for anyone with meaningful unprotected assets to have a nice, fat umbrella policy.

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