The $23 Lesson: Why Keeping Quiet Taught Me Who Really Knew Nothing

When I was younger, I didn’t say much. I figured keeping quiet was the best way to avoid trouble. I didn’t want to create waves, and truthfully, I thought that was how you earned respect, by keeping your head down and working hard. I thought if I didn’t make noise, people would notice my effort and appreciate it. Turns out, silence doesn’t always command respect — sometimes it just gives fools more room to talk.

When I was at Boston University for my LLM, our classes were at night, so I decided to get a part-time job at a law firm. I landed one at Bernkopf Goodman, a medium-sized Boston firm with about thirty lawyers. The place was split between litigation and real estate, with one lonely negligence attorney floating around.

One afternoon at lunch, that negligence lawyer and one of the real estate partners started goofing on me. I don’t even remember what about — probably something stupid. I just sat there, said nothing. They were partners, and I was a $23-an-hour law clerk trying to build a résumé. At that age, you assume anyone older, especially a partner, must be smarter and wiser. You think success automatically equals intelligence.

Here’s the punchline: they weren’t. The negligence guy ended up leaving to hang his own shingle, and the real estate guy had to tag along with a senior partner just to keep clients. In the end, they weren’t anything special, just two insecure lawyers trying to make themselves feel bigger by cutting someone else down.

It took me years to learn that lesson, that title and experience don’t equal competence or integrity. The law is full of people who confuse volume with knowledge and seniority with wisdom. Sometimes the loudest voices in the room are the ones who know the least.

And me? I kept quiet then because I didn’t know better. But life has a funny way of teaching you when to speak up. Today, I don’t stay silent when I see something wrong, whether it’s a bad plan design, a fiduciary mistake, or some self-proclaimed expert making it up as they go. Because I’ve learned that being quiet to keep the peace only helps the people who don’t deserve it.

Those two partners at Bernkopf Goodman? They probably forgot that lunch. I didn’t. Because in the end, they weren’t better, they weren’t wiser, they just got there first. And years later, when I built my own practice and my own voice, I realized something important: I was never beneath them. I was just still becoming me.

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The Hill Worth Dying On

On a client call the other day, we were knee-deep in the usual chaos that comes with transitioning to a new TPA, mapping plan provisions, reconciling documents, and making sure the new prototype plan doesn’t trip over the old one. These calls are a blend of ERISA minutiae and emotional endurance tests.

Then came the sticking point: the automatic enrollment percentage. The old plan defaulted participants at 1%, but the new TPA’s system didn’t like anything under 3%. HR hesitated. “We’ve always done 1%. I’m not sure our employees will go for 3%.”

That’s when I said it: you know your employees better than anyone, even better than an ERISA attorney.

Automatic enrollment isn’t just a checkbox in a plan document; it’s behavioral finance in action. Whether the number starts at 1% or 3% changes how people view saving. One feels like a token effort, the other like a meaningful start. But culture matters, and no one understands the culture of a company better than the people inside it.

Sometimes, plan design comes down to principle. You pick your hills. For me, this one was worth dying on, not because of 1% or 3%, but because ownership matters. A plan sponsor who listens to their workforce and stands by what works for them? That’s fiduciary leadership in its purest form.

At the end of the day, TPAs, attorneys, and recordkeepers all provide structure and compliance. But the sponsor is the heart of the plan. You know your people, their fears, habits, and paychecks, better than any spreadsheet or prototype document.

And that’s why, when it comes to the right default percentage, the real answer isn’t in ERISA Section 404(c). It’s in the breakroom conversations, the payroll deductions, and the quiet trust between employer and employee. That’s the hill I’ll always stand on.

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$2.1 Trillion of Forgotten Assets

Folks, here’s something that ought to wake up even the sleepiest retirement-plan consultant: there are now an estimated $2.1 trillion in “forgotten 401(k)” assets out there — accounts people either abandoned, forgot about, or lost track of. That’s not pocket change. That’s systemic drift.

The Scope of the Problem

We’re not talking about a few stray accounts. We’re talking about trillions. The kind of number that forces you to squint and ask, “How did we let this happen?” What used to be anecdotal is now a deep structural issue. Between job changes, mergers, relocations, or just poor communication, these accounts slip through the cracks.

Why It Matters (Beyond the Headline)

1. Fiduciary exposure. Plan sponsors and administrators can’t wave this off as someone else’s problem. If participants come knocking (and they will), questions will be asked about due diligence, communication, tracing efforts.

2. Participant outcomes. Sure, some of these will be small balances. But left unchecked, even small balances can erode via fees, inflation, misallocation, or poor default investments. A forgotten 401(k) isn’t just “dormant”—it’s being whittled away.

3. Operational burden & inefficiency. The administrative drag of attempting to locate and reconcile these accounts, the headaches of potential litigation, the reputational risks—these are real, material costs.

What Can Be Done (Yes, There Are Moves)

· Proactive outreach & communication. Use data (postal, email, phone) to actively engage participants who haven’t interacted with their account in year(s).

· Automated tracing & matching technologies. Modern tools can help reconcile current and past addresses, employment records, or cross-entity databases to find “lost” participants.

· Default consolidation policies. When employees leave, making consolidation (or forced rollover) the default unless they opt out reduces fragmentation.

· Standardized disclosure and reporting rules. Benchmark what “best practice” looks like (timely statements, nudges, transparency) and push the envelope there.

· Collaborative industry efforts. Cross-plan data sharing (within privacy and regulatory bounds), third-party locate services, or even regulatory nudges can help reduce the burden on individual plan sponsors.

A Warning & a Call

Let me be clear: this is not a quaint administrative nuisance. This is a symptom of a retirement system under strain. If $2.1 trillion can just evaporate into “forgotten” accounts, how many other cracks are we ignoring? If we let complacency reign, we risk undermining confidence in workplace retirement plans.

My appeal to all of you managing, governing, advising: treat forgotten accounts as a first-order priority. Don’t relegate them to the “administrative back burner.” Get moving now — because those assets? They belong to people, not spreadsheets.

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When $17.5 Million Is the Real “Fiduciary Breach”

Another week, another headline from the ERISA litigation circus — this time it’s Jerry Schlichter asking for a $17.5 million payday in the Pentegra case. That’s right, after landing what’s being called the largest jury verdict ever in an ERISA class action ($38 million) and then settling for $48.5 million, Schlichter’s firm now wants a third of the pot.

Don’t get me wrong — they did the work. Five years, 16,000 hours, over a million dollars advanced in expenses. But when the attorneys’ fee motion is as big as the recordkeeper’s alleged overcharges, it makes you wonder who really benefits from “fiduciary duty.”

If the court grants it, this could set a new benchmark — not for prudence, but for profit. Plan sponsors should take note: these lawsuits aren’t just about plan fees anymore; they’re about who gets the biggest slice of the settlement pie. The plaintiffs’ bar calls it justice. I call it a business model.

As Lucille Bluth would say, “Good for her.”

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When Default Rates Spike — Don’t Let Your Plan Be the Next Headline

We’ve all kept an eye on default rates creeping upward lately. But here’s what catches my attention: rising defaults don’t just affect participants, they test the backbone of a plan’s design, governance, and fiduciary discipline. As defaults increase, questions cascade: Are your safe-harbor defaults still appropriate? Are participants being nudged properly, or shoved into poor allocations just because inertia took over?

Higher default rates can mask hidden trouble. Plans that lean too heavily on default strategies may see behavior that deviates wildly from expectations. That increases the risk that someone will point at you and say your “qualified defaults” weren’t in participants’ best interests after all.

The fix begins before defaults spike: regularly stress test your default strategy; monitor participant behavior; consider a tiered or graduated approach rather than a one-size option; and document your rationale every step of the way. When default rates go up, the difference between prudent design and litigation bait is how defensible your structure and process were before the risk spike.

Because once default rates are high and things go sideways, plaintiffs and regulators don’t ask whether you hoped it would be fine, they ask how you prepared for exactly this.

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Fiduciary Duties, Board Retreats, and a Lesson from Sunrise Highway

Serving as counsel to a private school board, I had the chance to join their recent retreat, and I think it went pretty well. I gave a talk on fiduciary responsibility, what it means for the board, how it shapes every decision, and how duties extend beyond the four walls of a classroom. We even touched on social media, which, in today’s world, can be both a blessing and a liability for schools.

That reminded me of a story I wrote about in Full Circle. Fifteen years ago, I told the managing attorney at my old law firm that I wanted to use social media to build a national ERISA practice. You’d think I suggested selling fish out of a trunk on Sunrise Highway and Route 110. She was visibly displeased, as though the mere thought of self-promotion was unbecoming of a lawyer. The firm, already too old in its thinking, couldn’t see where things were headed. And as I predicted, it’s now less than half its size compared to when I left in 2010.

Why do I share this? Because it’s vindication, yes, but also a real-world example of how communication tools—whether Twitter, LinkedIn, or a blog post like this—aren’t frivolous. They’re powerful. They built my practice. They gave me a national platform. And for schools, boards, and nonprofits, they can be equally powerful tools for engagement, transparency, and trust, when used wisely.

Fiduciary duty isn’t just about numbers on a balance sheet; it’s about vision. It’s about seeing risks and opportunities before they knock you over. And sometimes, it’s about not being afraid to sell a dish or two from the trunk if it helps you get the word out.

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Don’t Let AI Become Your Liability: Smart Steps for Plan Sponsors

AI can feel like magic—predicting outcomes, personalizing communications, streamlining decisions. But in the fiduciary world, magic without guardrails is a ticking lawsuit. Here’s what every sponsor should do before turning on the “AI switch”:

1. Start with your risk appetite, not the vendor’s pitch.

AI’s predictive analytics and digital twins are tempting. But before you deploy, calibrate how much error or bias you accept. Don’t let vendor demos drive the strategy—your fiduciary obligations must.

2. Document your governance at every layer.

Every AI model, training dataset, output, override decision—capture the thinking. When plaintiffs probe, “Why did you trust that algorithm?” your minutes and memos must not go blank.

3. Test for bias, fairness, and “hallucinations.”

Algorithms can replicate systemic bias or “invent” guidance (“hallucinate”) in surprising ways. Have independent audits. Validate recommendations manually in pilot runs before full deployment.

4. Keep humans in the loop.

Even the slickest model should defer to human judgment in edge cases. A chatbot nudging a participant toward a portfolio change? Let a fiduciary reviewer step in when thresholds are crossed.

5. Guard your data and privacy like it’s your last defense.

AI needs data—lots of it. But every data point is a vulnerability. Safeguard participant records, anonymize where possible, control access, and ensure your model can’t be reverse-engineered into private data.

6. Monitor outcomes continuously. Post-deployment, don’t set and forget. Watch for patterns of underperformance, discrimination, or abnormal behavior. If your outputs stray, pause, recalibrate, or shut down features.

7. Disclose transparently—and simply. Your participants don’t need an AI thesis, but they deserve clarity. Explain when AI is used, how, and what oversight exists. Don’t hide “automated advice” behind vague terms.

8. Start small—fewer assets, narrower scope.

Don’t let AI roll out across your entire plan at once. Use it first in lower-risk areas (communications, education, diagnostics). Gain operational trust before letting it touch portfolio or default mechanisms.

AI in retirement plans is not a gimmick, it’s a superpower, if constrained. But superpowers demand discipline, not recklessness. Do the homework now, build defensibility, and treat every AI decision as though it might end up in a complaint. Because in our field, the difference between innovation and exposure is always process.

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$46 Trillion and a Match to Be Reckoned With

When Pew reports that U.S. retirement assets crossed nearly $46 trillion in Q2 2025, it’s easy to be awed by scale. But what really caught my eye was their spotlight on the Saver’s Match, set to launch in 2027, and how it might supercharge automated savings programs like state auto-IRAs.

Here’s why I take this as both opportunity and warning:

· Incentives change behavior. The Saver’s Match promises a 50% federal match (up to $1,000 single / $2,000 married) deposited directly into eligible retirement accounts. That kind of incentive could turn passive savers into active savers. Operational complexity will be your fiercest adversary. The match can only go into traditional IRAs (not Roth), and many eligible contributors don’t even file federal returns. If the claiming process is clunky, much of the upside evaporates.

· Governance & process matter more than ever. With new dollars on the line and more participants entering via auto-IRA programs, the fiduciary exposure multiplies. Every allocation, every match, every error will be under the microscope.

· Disparities at stake. The match is targeted to low- and moderate-income workers—those groups historically underrepresented in plan ownership. So the upside is strong. But failure to deliver could worsen distrust.

So here’s what every plan sponsor, provider, and fiduciary should do now:

1. Model the match impact. Simulate how many new accounts, how much additional assets, and what processing burden the match could generate.

2. Design claiming systems defensibly. Make the match automatic where possible; minimize steps. If the software, payroll systems, or tax forms are awkward, you’ll get caught on the backend.

3. Layer in governance. This isn’t just about new dollars—it’s about managing massive growth while keeping fees, conflicts, and errors in check.

4. Communicate clearly. For people who’ve never been in a retirement plan, the match and how to access it must be simple, transparent, and low friction.

If the Saver’s Match works as intended, it could reshape the retirement savings landscape in America. But with great policy comes great responsibility. In a world of $46 trillion, the biggest differentiator will be who builds systems built for scrutiny—not just scale.

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$46 Trillion: A Milestone Wrapped in Responsibility

When total U.S. retirement assets hit a record $45.8 trillion in Q2 2025, it was headline news—and for good reason. not just a number; it’s a massive concentration of faith, expectations, and fiduciary risk. As one of the largest pools of private capital in our economy, these assets demand more than passive oversight—they demand vigilance.

But here’s the rub: growth begets scrutiny. As assets swell across IRAs, 401(k) plans, defined benefit plans, and annuity reserves, so too does the pressure on those entrusted to manage them. Are fees justified? Are conflicts disclosed and controlled? Are processes defensible? Every basis point and every decision now carries outsized exposure.

Plan fiduciaries must treat every allocation, every document, and every conversation as though it might land in a complaint. In a $45.8T world, there are no small cases—only small defensibility. The capital may be growing. But so is the need for ironclad governance, razor-sharp documentation, independent review, and transparency from top to bottom.

Because when you’re responsible for tens of trillions, there’s no margin for error.

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When Even a Firm of Lawyers Is Accused of Mishandling Retirement Assets

It’s one thing for a corporate giant to be hit with fiduciary litigation—but quite another when the defendant is a law firm built on legal discipline. The recent lawsuit against Husch Blackwell, filed by a former partner, alleges the firm withheld employee 401(k) contributions, failed to timely forward them, and used them to cover its own operating expenses. \

What jumps out to me is how this case exemplifies the “small & grab” risk—where an internal actor becomes plaintiff, and a single misstep can become a full-blown ERISA action. If part of your firm’s compensation structure or benefits plan involves withholding or directing funds, you better have your fiduciary house in order: clean trails, strict oversight, independent review, and no ambiguity about every penny’s direction.

Because in the retirement plan world, the people doing the suing sometimes know the law better than you do—and they’ll drag you through all your own documents.

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