The Open Enrollment Trap: How High-Earners Leave Money on the Table Every Year
Every fall, it happens. You log into your company’s benefits portal between meetings, click through a few boxes, and tell yourself, “Done for another year.”
Except… those few clicks may have just cost you thousands.
For high earners, open enrollment isn’t HR busy work, it’s a stealth wealth opportunity. The choices you make this season can shape your tax bill, your savings, and your long-term financial security for years to come.
Let’s break down the biggest plays…and how to stop leaving money on the table.
1. HDHP vs. PPO: The Great Health Plan Debate
This is the decision that trips up even the savviest professionals. Many default to the comfortable PPO — the “safe” option with predictable copays and lower deductibles. But for healthy families and disciplined savers, that choice often leaves real money behind.
Enter the High Deductible Health Plan (HDHP) the hidden gem of open enrollment strategies. Pair it with a Health Savings Account (HSA), and you’ve unlocked a triple-tax-advantaged tool that lets you:
Contribute pre-tax (reduces taxable income)
Grow tax-free (invest it like a stealth IRA)
Withdraw tax-free for qualified medical expenses
Here’s the kicker: Unused funds roll over forever. Treat your HSA like an extra retirement account wearing a doctor’s coat.
The Play:
If your household’s medical needs are relatively light, an HDHP with HSA access is often the smarter long-term choice. You’re not just saving on premiums, you’re compounding wealth.
2. HSA vs. FSA: Know the Difference or Lose Real Money
Confusing these two accounts is like mixing up a Roth IRA and a checking account — both save taxes, but one builds lasting wealth.
The Opportunity:
If you’re eligible, the HSA is your secret compounding engine. If you’re not, an FSA still provides solid, short-term tax relief for predictable expenses like contact lenses or orthodontics. Just make sure you actually use the funds before the year ends.
Mid-Season Timeout:
Not sure which plan fits your playbook? That’s where strategy pays off. Book a Clarity Call to ensure your benefits are aligned with your broader wealth plan — not working against it.
3. Disability Insurance: The Most Underrated Protection
Here’s a stat most overlook: For high earners, your future income stream could easily be worth $5–$15 million over the next 20 years. Yet many professionals protect their car better than their paycheck.
Employer-provided disability insurance often falls short — limited coverage, taxable benefits, and caps that ignore bonuses or equity.
Think of it this way: Going without adequate coverage is like Tua Tagovailoa lining up without an offensive line — one hit, and your financial game could change overnight. And as any Dolphins fan knows, that’s happened far too many times.
The Play:
Supplement your employer plan with private coverage or better coverage than the free option so it protects your full income picture. It’s not fear-based, it’s fundamentals.
4. Life Insurance: Protect the Household MVPs
If someone depends on your income, you need term life insurance. Full stop. Benefits season is the perfect time to review whether your coverage actually fits your family’s needs.
Most employer plans:
Don’t cover your full income replacement goals
Often disappear when you leave the company
Rarely account for future obligations like college tuition or mortgage payoff
The Opportunity:
Own a portable, personally underwritten policy that stays with you. The goal isn’t morbid planning; it’s peace of mind for your family.
5. 401(k) Contributions: Don’t Leave Free Money on the Bench
If your employer offers a match and you’re not contributing at least that much…you’re refusing a guaranteed raise.
Beyond that, high earners should explore:
Roth 401(k): If you expect higher taxes later.
After-Tax Contributions + Mega Backdoor Roth: If your plan allows it, this is the ultimate tax-advantaged savings accelerator assuming proper short-term liquidity.
The Play:
This isn’t just retirement saving. It’s future freedom funding.
The Bottom Line: Treat Enrollment Like a Financial Playbook
Most high earners skim benefits forms like they skim Terms & Conditions. But those choices — plan types, contributions, coverage levels — quietly shape your long-term financial success.
Treat open enrollment as a chance to optimize, not overlook.
You’ve worked too hard to let default boxes dictate your financial future. Make this year the one where your benefits actually benefit you.
Ready to elevate your strategy?
Learn more about our 360° Wealth Process and discover how Julius Wealth Advisors helps you build wealth by choice, not chance.
Disclosures:
This piece contains general information that is not suitable for everyone and was prepared for informational purposes only. Nothing contained herein should be construed as a solicitation to buy or sell any security or as an offer to provide investment advice. The information contained herein has been obtained from sources believed to be reliable, but the accuracy of the information cannot be guaranteed. Past performance does not guarantee any future results. The information in this material is not intended as tax or legal advice. Please consult legal or tax professionals for specific information regarding your individual situation. For additional information about Julius Wealth Advisors, including its services and fees, contact us or visit adviserinfo.sec.gov.