There’s a hard truth in life, and I learned it the long, slow, and silent way: if you don’t speak up for yourself, you’ll be passed over, stepped on, and probably volunteered to clean up after someone else’s kugel spill. As I wrote in Full Circle, back in my teenage years at Young People’s Synagogue at East Midwood Jewish Center, I played the role of the dutiful nice guy. You know, the one who showed up early, stayed late, and never got the title—kind of like the unpaid intern who’s somehow also your carpool ride. Leadership roles were doled out like parts in a high school musical directed by someone’s passive-aggressive older cousin. The person assigning them? A college student named Adam. And every year, Adam gave me the same role: guy who does everything and gets nothing. He made people co-officers who didn’t even show up. He passed me over for president like it was a sacred tradition. And what did I do? Nothing. I sat there quietly, like a mensch with a clipboard, smiling through clenched teeth and rationalizing, “Maybe next year.” Spoiler: next year never came. Fast forward a couple of decades, and the stakes are a little higher now than who leads Shabbat announcements. I’m running my own law firm, negotiating retainers, and trying to deliver ERISA compliance without losing my mind—or my voice. So when a client recently slighted me, again and again—ignoring my reasonable request to revise a retainer agreement—I remembered Adam. And I remembered that feeling. The one where you know you’re being taken for granted, but you stay silent because it’s easier. Only this time, I wasn’t seventeen. This time, I said something. Actually, I said everything. I warned one of the client’s employees, “I’ve got one foot out the door.” A week later, I picked up the other foot and walked. I quit. And it felt… amazing. Liberating. Like finally being promoted to president of a synagogue you no longer care about. Here’s the truth: no one’s coming to rescue you. No one’s handing you the title, the recognition, or the revised contract. If you’re waiting for fairness to find you, it’s probably stuck in traffic behind a bar mitzvah procession. So speak up. For your fees. For your worth. For your teenage self who should have gotten the gavel instead of the handout flyer duty. Because being silent doesn’t make you righteous—it just makes you invisible.

I’m not anti-life insurance. In fact, I have life insurance, and I believe it’s one of the most important financial tools out there for protecting your loved ones. But when it comes to stuffing life insurance into a 401(k) plan, I have some strong reservations—and those reservations are grounded in reality, not theory.

Let’s be clear: I’ve seen what goes wrong when someone tries to get too clever with life insurance in a qualified plan. Sure, there are consultants and insurance agents who will spin it as an executive benefit strategy or a way to build cash value in a tax-deferred wrapper. But when the rubber meets the road, these arrangements often blow up in the face of the plan sponsor—and it’s the kind of explosion that can cost you the qualified status of your plan.

I’m not going to go into the defined benefit plan disasters where the plan is nothing more than a shell to pay insurance premiums—though I’ve seen enough of those trainwrecks to fill a chapter in a compliance horror storybook. I want to talk about what I see in 401(k) plans.

Problem #1: Discrimination Issues

Too many times, the life insurance component is offered only to company owners or a select group of executives. That’s a benefit, right, and feature. And if that benefit isn’t available to the rest of the plan participants, guess what? You’ve got a discriminatory feature that can cause a compliance failure. A 401(k) plan isn’t a private club for the C-suite. If you want to offer life insurance, it better pass coverage testing and be nondiscriminatory. Otherwise, you’re playing games with your plan’s tax qualification.

Problem #2: Titling the Policy

Here’s another compliance grenade I see too often: the insurance policy is titled directly in the name of the participant. That’s a problem. When an asset is held in a 401(k) plan, it needs to be held by the plan. If the policy is titled in the participant’s name without clearly being owned by the plan, you’ve just crossed into prohibited transaction territory. ERISA doesn’t play around with this stuff.

It’s not enough to say “Well, it’s in the plan documents.” It has to be executed properly—ownership needs to be in the name of the plan, there must be clear documentation, and it must comply with DOL and IRS rules. Otherwise, you’ve just created a liability where there didn’t need to be one.

Problem #3: Nobody Knows What They’re Doing

Let’s be honest. Most of the life insurance in 401(k) plans that I’ve seen was pitched by someone who didn’t fully understand the ERISA ramifications. This is not a plug-and-play product. If you’re not working with a team that understands both qualified plans and the nuances of insurance within those plans, you’re asking for trouble.

Look, I’m all for creativity in plan design when it serves participants, complies with the law, and avoids risk. But stuffing life insurance into a 401(k) plan because someone convinced the business owner it’s a slick tax shelter? That’s not creativity—that’s negligence.

Final Thought

If you’re a plan sponsor, keep it simple and compliant. Don’t chase shiny objects. Focus on good providers, reasonable fees, and a prudent process. That’s what ERISA demands—and that’s what protects your plan and your business.

And if you still want to put life insurance into a qualified plan? Fine. Just make sure your advisor actually knows what they’re doing. Because the IRS and DOL won’t accept “We didn’t know” as a defense.