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Welcome to the Pride's Friday Five

This week's edition is personal for both of us.

FLIP was honored to be featured in Independent Agent magazine's cover story on the industry's talent crisis. Mindi Zissman, freelance writer at large, did a fantastic job capturing the challenges and opportunities we're all facing. We're also sharing a powerful piece from our friend Brenden Corr on mental health, and closing with a wellness message from Tash.

Every Friday the team rips through 200+ insurance, legal, and market-risk articles and brings you the three your board needs to hear about in its Monday briefing.

Here's what caught our attention this week:

• The BIG I's Independent Agent magazine's cover story on the industry's talent crisis. Insurance is approaching a 400,000-worker deficit, but the problem isn't exactly what you think.
• Our friend Brenden Corr tackles a critical blind spot: 78% of employers have taken no steps to address secondary trauma in insurance professionals. Burnout isn't a personal failure. It's a system failure.
• And something different this week — a message from Tash on the 250 Pilates classes she completed last year, and what Joseph Pilates' six principles taught her about running an insurance operation.

Three events we think deserve a deeper dive…First, If you'd rather listen check out the audio version.

The 400,000-Worker Industry Problem Isn't What You Think

Summary

From FLIP: I shared some thoughts recently with the BIG I for their Independent Agent Magazine on what we're doing about it at LION. How we're using social media, leading with tech opportunities, and training people from the ground up.
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The professionals who taught us this business didn't hoard the knowledge. Neither should we!

LION's friend Mindi Zissman did a fantastic job capturing what's really happening. The real problem isn't what most people think. The insurance industry is approaching a 400,000-worker deficit as baby boomers retire. That number sounds catastrophic until you understand the gap. Gen Z isn't avoiding insurance careers. They simply don't know fulfilling insurance careers exist.

College juniors and seniors pursuing insurance show clear preferences for organizations that prioritize people, mental well-being, equitable pay, and community support, according to Gamma Iota Sigma's 2025 recruiting survey. When comparing employers, students most often highlighted corporate culture as their key differentiator. The industry has what younger generations want.

The gap is awareness, not appeal. What are we all doing about it is the billion dollar question!

(source: IA Magazine / Mindi Zissman)

So what?

The talent pipeline requires deliberate investment, not passive hope.

Independent agencies succeeding at recruitment share common strategies: authentic social media presence, classroom engagement at local high schools and universities, structured internship programs, and internal professional development tracks.

The math is simple. 400,000 jobs won't fill themselves tomorrow. But there's nothing that says they can't be filled in the next five to ten years...If the industry invests in telling its story now.​
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The Burnout Blind Spot That Needs Some Sunlight

Summary

Insurance professionals are experts at managing external risk. The internal resilience of the workforce? That's the next frontier — and right now, it's a blind spot.

A 2023 Chartered Insurance Institute study asked whether claims professionals in the UK experience secondary trauma while managing distressing claims. The findings were stark. Senior leadership often dismisses exposure to traumatic claims as merely part of the job. The psychological toll of claims work remains largely unstudied in an industry built around risk mitigation.

The World Health Organization classifies burnout as an occupational phenomenon resulting from chronic workplace stress that hasn't been successfully managed. It manifests in three dimensions: exhaustion, cynicism, and reduced professional efficacy. Insurance professionals recognize these signs well — the exhaustion no amount of coffee can counteract, the cynicism that breeds frustration, the declining performance despite ever-longer hours.

As Brenden Corr writes, addressing this requires deliberate action: prioritizing mental health alongside physical health, encouraging transparency and open dialogue, supporting colleagues through active listening and empathy, monitoring for and quickly stepping in amid signs of burnout, and leveraging community resources like Project 55.

(source: Insights Magazine / Brenden Corr)

The LION Lens

What happened — The CII study found 78% of employers have taken no steps to identify, prevent, or manage instances where secondary trauma could arise. 54% of employers provide no support to employees who encounter distressing claims. And 56% of claims professionals who suffered stress from handling distressing claims didn't feel comfortable disclosing it (source: CII, 2023).

Why it matters — The data reveals a critical gap between how the industry manages external risk and how it manages internal resilience. Behind every policy, every renewal, and every client interaction is a human being who deserves to be well.

Practical implications — Burnout is not a personal failure. It's a system failure. The by-product of a culture that rewards overextension. Recovery requires shifts in both culture and practice.

So what?

Brenden offers five ways to rethink burnout at the organizational level:

Normalize acknowledgment and dialogue. Recognizing burnout is the first step. Following up with transparent conversations with managers or HR can lead to redistributed workloads and prioritized tasks.

Recharge without guilt. Taking paid time off, mental health days, or a brief leave of absence can provide the space to recover and return with renewed focus. We need to stop thinking this is weakness. It's maintenance.

Reevaluate workloads. Professionals benefit from reassessing daily tasks, eliminating low-value commitments, and concentrating on essential responsibilities.

Incorporate recovery practices into routines. Short walks, deep-breathing exercises, or scheduled breaks for disconnection function as ongoing maintenance against long-term decline.

Encourage collegial accountability. Colleagues may notice burnout in others before the affected individuals notice it themselves. A culture that normalizes speaking up creates space for early intervention.

Resources exist. Project 55, a not-for-profit co-founded by Justin Goodman and Brenden Corr, offers free Mental Health First Responder Training covering stress, burnout, depression, PTSD, suicidal ideation, and addiction. The goal isn't to transform insurance professionals into therapists. It's to normalize conversations about mental health and ensure that colleagues who express "I am not OK" are met with compassion, not stigma.

The LION POV

Here's how we're thinking about this:

• Acknowledge the disconnect. We manage risk for clients all day. We should apply the same rigor to our own teams. That starts with recognizing burnout as a system failure, not individual weakness.
• Build recovery into the culture. Not as an afterthought. Mental health days, redistributed workloads, and collegial accountability aren't perks — they're operational resilience.
• Check the resources. Project 55's free training program is worth reviewing. The industry's sustainability depends on sustaining its people.

The growing willingness to address mental health openly is itself progress. What was once layered in stigma is increasingly acknowledged as essential to sustaining both people and organizations.

Interested in learning more about Project 55? Visit project55.org or reach out to Brenden Corr directly.

The Six Principles — A Message from Tash

Summary

Joseph Pilates built his practice around six principles. Turns out, they're parallels for running an insurance operation.

I completed 250 Pilates classes last year. The connections weren't obvious at first — until they were.

Breath. In Pilates, you move through hard movements with intentional breath. You're connected to your body, connected to the work. Many of the C-suite executives we work with practice meditation. They know that grounding yourself in chaos is survival.

Precision. Every toe placement, every hand position, every micro-movement matters. This parallels policy review. Line by line, truly line by line. No guesswork.

Control. Not controlling others. Control as in evenness, smooth movements, the ability to stay calm when goalposts move because you've prepared for the permutations. Our 150-day renewal timeline exists for exactly this reason.

Concentration. Pilates demands total presence. When you're in class, you're not thinking about anything else. That same deep focus lets you understand a client's risk well enough to negotiate a deal that actually fits.

Flow. All of those precise, controlled movements with enough repetition, they become graceful. The law of 10,000 hours. We've been running this same process for decades, and the threads pull together into something clients actually feel.

Centering. In Pilates, every movement comes from your core. In our work, the core question is simple: How do we make the client's life easier? That question answers almost everything else.

(source: Natasha Kiemnec / LION Specialty)

So what?

The discipline that makes you stronger in the studio is the same discipline that makes you better at the work. Precision. Presence. The parallels extend beyond metaphor into practice — which is why an increasing number of executives are building physical disciplines into their routines alongside the professional ones.

The Bottom Line

The insurance industry is facing a people problem on multiple fronts. A 400,000-worker deficit demands better storytelling and investment in the next generation. A burnout blind spot requires treating internal resilience with the same rigor we apply to external risk. And the executives leading through this moment? They're building personal disciplines that mirror the professional ones — because sustainable performance requires sustainable people.

And In Case You Missed It!

While Friday is for market signals, Wednesday is for structural intelligence. Insider to insider.

This week's Friday Five featured Brenden Corr's powerful piece on burnout as a system failure. It got us thinking about how we've tried to build the opposite, what we call the Insurance Blue Zone.

When we walked away from the mega-broker machine at the end of 2022, it took six months just to decompress. We'd worn exhaustion like a badge of honor. Long hours. Weekly travel. Drinking too much. We kept telling ourselves, "It's just the business."

Then we started asking a different question: What if the biggest risk to your insurance program isn't the market — it's your broker's burnout?

The Blue Zone approach inverts the traditional model through three disciplines: integrated wellness (not a perk, built into operations), ownership alignment (92% team retention over twenty months), and service excellence as a natural byproduct (you can't manufacture caring from burned-out people).

Brenden's right that burnout is a system failure. We built a system designed to prevent it.

Read: Is Burnout Your Largest Risk Exposure?​
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Stay Covered,

TASH & FLIP

Co-Founders and Managing Partners

LION Specialty