July 2025
Let’s say I have a friend who hates taxes in the worst way—not just paying them, but the complexity of the paperwork, the IRS legislation, all of it. So when the TCJA was passed at the end of 2017, he saw an opportunity: Take advantage of higher estate and gift tax exemptions and lower tax rates, get his finances in order (via a Trust), and bam—he wouldn’t have to worry about that part of the tax equation anymore.
… Imagine his frustration earlier this month when the Big Beautiful Bill made the estate and gift tax exemptions permanent and extended the current low marginal rates. The tax win he was chasing? Gone. The complications? Still there.
He tried so hard to simplify his life … that he actually made it more complicated.
Here’s the thing: many of us overcomplicate our lives frequently, for various reasons. Let’s get into why we fail to simplify things, so we can see if there’s a better way.
(By the way, we’ll be reviewing ALL of our clients’ financial plans in light of the Big Beautiful Bill Act, but that doesn’t you should be stressing over the details.)
(p.s. Did you know the phrase KISS is the brainchild of a Midwesterner?)
“Trust me, I’m a professional”
That phrase inspires more laughter than trust most of the time. Why?
In the world of finance, I suspect it’s because no one really knows what financial professionals do. Some of this is by design. Investment advisor (technically adviser) is a regulated term. But most of the other job titles out there? It’s the wild west.
If someone tells you they’re a banker, it could mean anything from “teller at your local branch” to “financing billion-dollar deals.” A financial advisor can be equally vague—you don’t know whether they do planning, investments, taxes… the services, or lack thereof, can be a mixed bag.
So how do you simplify things?
Most people will tell you to look at credentials and certifications. And that’s a nice place to start. But frankly, it’s not enough. That will tell you what people are qualified to do, or allowed to do. Certifications and the fancy letters after someone’s name don’t tell you who to call when there’s a problem.
If you really want to simplify your finances, I suggest spending (investing!) some time finding a holistic wealth advisor who can serve as the “quarterback” for your finances. Yes, it might take you more time to find this person, which doesn’t feel simple. But once you do, they’re your first and only call 90% of the time. They’ll tell you who you need to call next (if you need to call someone else), then make a referral or, better yet, make the call themselves.
This type of service is called a virtual family office, and it’s what we offer at Trailhead. We create not only your investment and financial plan, but also help source and coordinate a whole host of professionals working in your best interest. Because what’s simpler than narrowing the number of financial names and numbers you need to remember… down to one?
This meeting could have been an email
Raise your hand if you hate meetings. Most people I know do. We’re inundated! Overwhelmed! And most meetings are inefficient and poorly run.
But that creates a catch-22 when it comes to money and family.
Most of the family disagreements about money come from people not being on the same page. One spouse has different expectations around saving than the other… or parents get frazzled every time they need to make a call on extracurriculars.
And this is where family meetings—something that can seem complicated on the surface—actually simplify things. Those meetings can help you get on the same page about big picture ideas, which makes it much easier (simpler!) to make day-to-day decisions.
You can make those meetings more effective by bringing an agenda to the table. I know what you’re thinking—an agenda seems formal and complicated! But agendas help make sure you don’t forget things, so you can take care of business quickly and get back to life. I’m including a sample agenda here.
I also thought I’d share my family’s mission statement. It’s something we put together during a family meeting, and it helps us simplify our daily life.
“I should have told them straight to you”
One of the big morals of this email? Even when it feels complicated, direct communication is important.
I’ve spent too many words already making this point in an academic fashion. Now it’s time to make the point in a… more artistic way. The music video for my band’s ballad, Riverside, is out now. After thinking through this month’s email, the lyrics hit just a little bit harder. (And fast forward for a view of my very cold fingers trying to remember the guitar solo before a winter gig earlier this year).
