Fall often marks the start of Open Enrollment, the brief window when you can review and adjust your employee benefits for the upcoming year. While it’s tempting to hit “renew” on last year’s elections and call it a day, doing so means potentially leaving money, tax savings, and long-term growth opportunities on the table.
If you’re a high earner focused on saving for retirement and building lasting wealth, Open Enrollment is more than an HR formality. It’s also a powerful moment to align your benefits with your broader financial goals.
Here’s how to make the most of this season, from optimizing your healthcare and retirement contributions to reviewing insurance coverage, equity compensation, and overlooked perks.
Planning for Open Enrollment
Open Enrollment typically takes place in the fall and lasts only a few weeks, with any changes taking effect in January. This short window is your opportunity to make important decisions that can shape your financial well-being for the year ahead.
Starting early gives you time to:
- Review last year’s benefit elections and how they served you
- Estimate upcoming medical expenses or life events, like a move, growing your family, or a career change
- Compare this year’s plan options and contribution limits
- Gather any necessary documents, such as pay stubs, prior benefit summaries, and health expense records
Rushing through these choices can potentially lead to costly missteps. According to a recent Equitable survey, 53% of employees with access to workplace benefits regretted their choices during the previous Open Enrollment period. The most common reasons included:
- Failing to adjust benefits after major life changes (25%)
- Missing the deadline altogether (20%)
- Not fully understanding their options (19%)
This is also an ideal time to check in with your financial advisor or CPA, especially if you’re coordinating benefits with a spouse, adjusting your retirement strategy, or planning around significant tax considerations.
#1: Healthcare Benefits
As healthcare costs continue to rise, your employer-sponsored health benefits can represent a significant portion of your total compensation, making them a smart starting point during Open Enrollment.
Health Insurance
Begin by taking a close look at your current healthcare plan. It’s important to assess whether you’re paying for more coverage than you need, or if you’re exposed to potential out-of-pocket costs that aren’t adequately covered.
For those in good health with sufficient savings, a high-deductible health plan (HDHP) combined with a Health Savings Account (HSA) can be a strategic choice, offering lower premiums and valuable tax advantages.
Health Savings Accounts (HSAs)
If you’re enrolled in a high-deductible health plan, an HSA can be a valuable benefit during Open Enrollment. HSAs come with a rare triple tax advantage: contributions are tax-deductible, the money grows tax-free, and withdrawals for qualified medical expenses are also tax-free.
For 2026, IRS contribution limits will increase to:
- $4,400 for individuals
- $8,750 for families
- An additional $1,000 catch-up contribution if you’re age 55 or older
Unlike other healthcare benefits, HSAs are yours to keep. The funds aren’t tied to your employer and never expire, which means you can take your HSA with you if you change jobs and continue using it as a long-term savings vehicle, even in retirement.
Flexible Spending Accounts (FSAs)
If you aren’t eligible for an HSA, a Flexible Spending Account (FSA) also offers meaningful tax savings. FSAs let you set aside pre-tax dollars for qualified healthcare or dependent care expenses, reducing your taxable income.
Just be aware of the “use it or lose it” rules. Unlike HSAs, FSA funds generally must be used within the plan year, unless your employer offers a short grace period or limited carryover.
Dental and Vision Coverage
Lastly, take a close look at your dental and vision options to determine whether higher-tier coverage makes sense for the year ahead. Upgrading may be worthwhile if you or a family member expects to need orthodontics, LASIK, or other major procedures that come with significant out-of-pocket costs.
#2: Retirement Benefits
Retirement benefits play a critical role in your long-term financial plan, often offering valuable opportunities to accelerate your tax-advantaged savings through employer-sponsored plans and contributions.
401(k) and Roth 401(k)
During Open Enrollment, review your contribution rate and consider increasing it if you have room to save more. The IRS typically announces updated contribution limits near year-end, so check that you’re on track to maximize contributions.
If your employer offers a match, make sure you know how to receive the full benefit as this is essentially free money. You’ll also want to revisit how you’re dividing contributions between traditional and Roth accounts (if available).
Roth 401(k)s offer tax-free growth and withdrawals in retirement, which can be particularly valuable if you expect to be in a higher tax bracket later or want to hedge against future tax increases. And unlike Roth IRAs, Roth 401(k)s have no income limits, making them an excellent option for high earners who may be ineligible to contribute directly to a Roth IRA.
After-Tax Contributions and Mega Backdoor Roth
If your 401(k) plan allows after-tax contributions beyond the standard IRS limits, you may have access to a strategy known as the Mega Backdoor Roth. This involves making after-tax contributions to your 401(k), then rolling those funds into a Roth IRA or Roth 401(k), allowing for even more tax-advantaged growth.
For high earners who have already maxed out traditional and Roth 401(k) contributions, this strategy can significantly expand retirement savings in a tax-efficient way. Not all plans offer this feature, so it’s worth checking with your HR or benefits team to see if it’s available and working with a financial advisor to execute it properly.
#3: Equity Compensation
Equity compensation can be a valuable component of your total benefits package, but it also comes with layers of complexity. Open Enrollment is a smart time to review your equity and ensure you’re maximizing its long-term value within the context of your broader financial plan.
Employee Stock Purchase Plan (ESPP)
If your employer offers an ESPP, take time to review your contribution level and evaluate whether you’re taking full advantage of the plan’s benefits. Many ESPPs allow you to purchase company stock at a 10–15% discount, creating an immediate return on your investment and a potential tax advantage if you qualify for favorable capital gains treatment.
While ESPPs can be a compelling way to build wealth, be mindful of overexposure to a single stock. Holding too much company equity can increase risk, so consider how ESPP shares fit into your overall portfolio and diversification strategy.
RSUs, ISOs, and Stock Options
If your employer has granted you equity awards like Restricted Stock Units (RSUs), Incentive Stock Options (ISOs), and non-qualified stock options, Open Enrollment is a good time to review your upcoming vesting schedules and prepare for key tax milestones. Keep in mind:
- RSUs are taxed as ordinary income when they vest, regardless of whether you sell the shares.
- ISOs may qualify for favorable long-term capital gains treatment if holding requirements are met, but they can also trigger Alternative Minimum Tax (AMT).
If you’re approaching a liquidity event, changing jobs, or holding concentrated stock, it’s essential to align your equity decisions with your tax strategy and overall portfolio to reduce risk and maximize the potential value.
#4: Insurance Coverage
Open Enrollment is a key opportunity to identify and address any gaps in your insurance coverage, ensuring you have the right protection in place.
- Life Insurance. Most employer-provided life insurance covers just 1–2x your salary, which is often far less than what’s needed to protect a family or meet long-term financial obligations. If you have dependents or significant responsibilities, review your coverage carefully and consider adding supplemental insurance to bridge the gap.
- Disability Insurance. Employer-sponsored disability plans often replace only a portion of your base salary and may exclude bonuses or equity. As you review your benefits, consider whether you need individual long-term disability coverage to fully protect your earnings.
#5: Legal and Estate Planning Benefits
Estate planning support is becoming an increasingly common part of employee benefits packages, and more employees are taking advantage of it. According to Mployer, the share of U.S. employers offering legal services rose by 6% in 2022, reaching 42% in 2023.
If your employer includes legal or estate planning services, Open Enrollment is a great time to take advantage. Be sure to review:
- Employer-sponsored legal services for drafting a will, establishing a trust, or creating other estate planning documents
- Beneficiary designations on your life insurance and retirement accounts, especially if you’ve experienced a major life event such as marriage, divorce, or the birth of a child
#6: Lifestyle Perks and Underused Benefits
In addition to core offerings like healthcare and retirement, many employers provide lifestyle perks that can meaningfully support your well-being and long-term growth. These benefits are often underused, but they can add real value when you take full advantage of them.
During Open Enrollment, look for options such as:
- Wellness or fitness reimbursements
- Mental health support or therapy stipends
- Continuing education or professional development opportunities
- Charitable donation matching programs
While they may not have the immediate financial impact of a 401(k), these benefits can enhance your quality of life and contribute to a more well-rounded compensation package.
TrueNorth Wealth Is Here to Help
For many employees, Open Enrollment is a key milestone in your financial planning year. Taking time to review your benefit elections with intention can help you make the most of your total compensation, lower your tax liability, and build a stronger foundation for long-term success.
At TrueNorth Wealth, our team of fiduciary CFP® professionals is here to guide you through the process. We’ll help you evaluate your options, align your benefit choices with your broader financial goals, and build a personalized plan that supports both your current lifestyle and your future aspirations.
TrueNorth Wealth is among the top Wealth Management firms in Utah and Idaho, with offices in Salt Lake City, Logan, St. George, and Boise. At TrueNorth Wealth, we focus on helping our clients build long-term wealth while maximizing the enjoyment they receive from their money. We do this by pairing our clients with a dedicated CFP® professional backed by an incredible team.
For our team at TrueNorth, it’s about so much more than money. It’s about serving families all across Utah and helping them achieve freedom and flexibility in their lives. To learn more or schedule a no-cost consultation, visit our website at TrueNorth Wealth or call (801) 316-1875.
