MML #048: Why Smart Lawyers Struggle to Hire Financial Advisors (And What to Do About It)

This past week I had a conversation with an extremely accomplished lawyer who now helps other attorneys position their firms for sale. Among the many fascinating topics we covered, we landed on something that's been rattling around in my head ever since: why lawyers struggle to pull the trigger on hiring financial advisors.

Now, before you shoot the messenger, hear me out. What this lawyer shared rubbed me the wrong way at first too. But the more I've reflected on it—and the more I've experienced it firsthand working specifically with attorneys—the more I've realized there's real truth here.

You're Skeptical

Lawyers are trained to be skeptical. It's what makes you exceptional at your craft. You're educated to look under every stone and peer into every corner. Most of your client answers start with "It depends," right? Facts and circumstances matter.

These are fantastic qualities that prevent impulsive decisions. But they can also severely hinder your ability to trust another professional—especially one handling your money. And let's be honest: in your line of work, you've either met a bad apple or two, or you've seen clients' misfortunes from trusting the wrong financial advisor.

I get it. I'm naturally skeptical too. My wife sees a benefit and she's ready to pounce. I see a benefit and immediately ask, "What's the catch?" So understand I'm also preaching to myself here.

There's no perfect remedy for this, other than taking baby steps. Read some articles. Follow some content. Schedule an introduction call. Just don't let the research lead to paralysis by analysis.

You're Cheap

Okay, that's harsh. Let me rephrase: you struggle to see the value in certain professional engagements, especially when you don't fully understand the benefits.

Here's an example from my industry. Many advisors, including myself, charge an "Assets Under Management" fee for financial planning and wealth management services. It's not a perfect fee model—no model is.

It's easy to find advice like "Save yourself the 1% and just invest your money in an index fund." Charts showing the erosion impact of an advisor's fee over a portfolio's lifetime are everywhere. Talking heads like Ramit Sethi have beaten this drum in his bestselling book I Will Teach You to Be Rich and his Netflix show How to Get Rich. (By the way, I genuinely appreciate Ramit's work—it's entertaining and inspiring. I don't have to agree with everything to embrace his effort to bring financial education to his audience.)

But here's what I often find missing from these articles: any discussion of what advisors actually do beyond building portfolios. No mention of tax planning. No estate planning. No risk management. No aligning your purpose with your money.

Dr. Derek Tharp, lead researcher at Kitces.com, wrote an excellent article called Quantifying (More Accurately) The Real Impact Of A Financial Advisor's Costs On Their Clients' Nest Eggs. He outlines the fallacies in common assumptions and the math that gets misrepresented.

The takeaway here is that if your financial advisor just talks about the S&P 500 once a year, you're probably better off saving the fee. But the returns of a good financial planner won't always show up as an itemized line on your brokerage statement. They show up in tax savings, estate efficiency, risk mitigation, and living a life aligned with what actually matters to you.

"I Can Do This Myself"

This one's huge, and it ties into the previous point. It runs deeper into your identity as an intelligent person. Some of this finance stuff seems pretty basic, and let's be honest—you have more formal education than most financial "sales professionals." Plus, if you can DIY it, you don't need to worry about any of the issues I've mentioned so far, right?

But let me ask you this: Have most of your clients Googled their legal needs and asked ChatGPT for opinions? Of course they have. Yet they're still knocking on your door because they know the details matter. Putting it all together isn't as simple as asking AI. It's nuanced. Sometimes you only get one shot at getting something right, and you charge handsomely for that important counsel—as you should. You're not charging for the template. You're charging for the years of education and expertise that went into creating that perfect template.

To put data around this, Vanguard published its Advisor's Alpha study highlighting the value a real financial planner brings beyond "picking investments." Let me say it again for the people in the back: Vanguard—the investment management juggernaut that prides itself on low fees—published this. Check it out if you're up for a deeper dive.

The Bottom Line

Look, skepticism is healthy. Being thoughtful about expenses is smart. Wanting to understand things yourself is admirable. But don't let these qualities—the same ones that make you an excellent lawyer—prevent you from getting the financial guidance you need.

The holidays are here, which means another year is almost in the books. If you've been thinking about working with a financial advisor but haven't pulled the trigger, I have a few remaining time slots for introduction calls before wrapping up 2025. No pressure, no sales pitch—just a conversation about whether working together makes sense.

Click here to schedule.

Next week, we’ll continue our recent theme of end-of-year planning strategies that bring real value (but may not show up on your brokerage statement).

I hope you’ll join me. I’m off to hang more lights..