S. 2 Ep 21: Let’s Get Fiscal: HR’s Guide to Retirement Realness with guest Courtenay Shipley

Grab your coffee—and maybe a calculator—because we’re getting real about retirement. In this episode, I sit down with retirement plan whisperer Courtenay Shipley to chat about all things 401(k), from why this benefit is more than just a line item to how we really need to be talking about it with our employees.

Whether you’re a manager, an HR pro, or someone who just keeps “set up 401(k)” on your to-do list indefinitely (we see you), Courtenay brings the clarity, strategy, and humor needed to finally make retirement planning feel… possible.

We talk about:
✅ Why retirement benefits still matter—yes, even for Gen Z
✅ The value of automatic enrollment (hint: it helps people who forget to adult)
✅ Why skipping the company match is like turning down free money
✅ The most common types of 401(k) plans and what makes each one tick
✅ Growth strategies that don’t require a finance degree
✅ Communication tips to help employees actually understand their retirement options
✅ Why helping people “get the why” is the key to better participation and less future regret

Courtenay also breaks down how to prepare for the transition to retirement and how organizations can support employees at every stage of their financial planning journey.

This episode is all about turning that “I’ll get to it later” mindset into “I’m on it!” Because let’s be honest—future-you deserves a nap on a beach, not a panic attack at 68.

Resources Mentioned:
🔗 Learn more about Courtenay and Retirement Planology: https://retirementplanology.com

📞 Connect with Courtenay Shipley

Courtenay Shipley, CRPS®, AIF®, CPFA, CEPA
Founder & Chief Planologist, Retirement Planology, Inc.

• 📧 Email: cshipley@retirementplanology.com
• 📞 Phone: (703) 595-2829
• 🌐 Website: www.retirementplanology.com
• 📍 Address: 950 N Washington Street, Suite 242, Alexandria, VA 22314
• 🔗 LinkedIn: linkedin.com/in/cshipley
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 📊 Want a better way to explain your 401(k) benefit? Courtenay’s team offers great tools to simplify complex terms for employees.

Three Takeaways for Managers & HR Leaders:

1. Don’t just offer the benefit—explain it like a human. Use real-life examples to make it click.
2. Default your people into greatness. Automatic enrollment works. Period.
3. Start the retirement convo early. Help your employees see their 401(k) not as a luxury, but as a lifeline.

Connect with Us:
💬 What’s the best financial advice your company ever gave you? DM me @managewithhart or tag us using #DearHRDiary
📩 Want help explaining benefits to employees? Visit www.managewithhart.com for tools and training.