Are You Leaving Money on the Table? Make the Most of Your Employee Benefits

July 12, 2024

Let's start with a little thought experiment. If we offered you an instant 30% pay raise, no strings attached, would you take it? Of course, you would! Who wouldn't want that kind of influx of extra cash?


Well, here's the thing — you may already be entitled to the equivalent of a huge pay bump through your employee benefits package. The only catch is that you actually have to take advantage of the benefits to reap the rewards.


You've worked hard to earn what you have. So why leave money on the table by not fully utilizing all your employer's perks and benefits? It makes no sense! 


Keep reading to discover how you can maximize your employee benefits and unlock their full potential. We'll show you just how lucrative employee benefits can be.


Understanding Your Benefits Package


First things first — familiarize yourself with what's included in your benefits package. This might seem basic, but you’d be surprised how many people don't fully understand their benefits. Key areas to focus on include:


  • Health Insurance
  • Retirement Plans
  • Stock Options and ESPPs.
  • Flexible Spending Accounts (FSAs) and Health Savings Accounts (HSAs)
  • Life and Disability Insurance


Your 401(k) Match 


Let's kick things off with a big one — your employer's 401(k) match. This is easily one of the most valuable benefits out there, yet it's still sadly underutilized.


For every dollar you contribute to your 401(k) retirement account (up to a certain percentage of your salary, usually 3-6%), some employers will match those contributions with free money from their end. You're literally getting paid to save for your future!


Let's say your employer offers a 4% match, and you earn $200,000 per year. If you max out the match by contributing 4% ($8,000) annually, your employer will kick in another $8,000 on top of that. Suddenly, your original $8,000 contribution has doubled to $16,000! Where else can you get a 100% return on your money just like that?


Over 30+ years that 401(k) match money could translate into hundreds of thousands of extra dollars for your retirement. It's such an easy way to accelerate your retirement savings and prepare for the future you want.


Even if your employer doesn't match your contributions, maximize your retirement contributions if you can afford it. In 2024, employees can contribute up to $23,000 into their 401(k), 403(b), most 457 plans, or the Thrift Savings Plan for federal employees. 


Maximize Health Insurance Benefits


Health insurance (including dental and vision) is often the most complex part of an employee benefits package. However, it’s also one of the most critical. Here are some tips to help you make the most of your health insurance:


  • Preventive Care: Take advantage of free preventive care services like annual check-ups, screenings, and vaccinations. These can help you catch health issues early, potentially saving you money and hassle down the line.
  • Wellness Programs: Many employers offer wellness programs that provide incentives for healthy behaviors, such as gym memberships, weight loss programs, or smoking cessation programs. Participating in these can improve your health and potentially reduce your insurance premiums.
  • Telemedicine: Check if your plan covers telemedicine services. Virtual doctor visits can be more convenient and sometimes cheaper than in-person appointments.


Take the time to understand the different plan options offered by your employer, including deductibles, copays, and out-of-pocket maximums. Carefully review the health insurance options during open enrollment each year. Don't just go for the cheapest option — consider your family's healthcare needs and choose a plan that provides the right coverage at a reasonable cost.


Flexible Spending Accounts (FSAs) and

Health Savings Accounts (HSAs)


FSAs and HSAs offer excellent tax advantages for covering medical expenses. Here’s how to maximize their benefits:


  • Contribution Limits: For 2024, you can contribute up to $3,200 to an FSA and $4,150 to an HSA ($8,300 for a family). If you’re over 55, you can contribute an additional $1,000 to an HSA.
  • Qualified Expenses: Use these accounts for qualified medical expenses, which can include doctor visits, lab work, prescription medications, and even some over-the-counter items.
  • HSA as a Retirement Account: HSAs have a triple tax advantage (tax-deductible contributions, tax-free growth, and tax-free withdrawals for qualified medical expenses). If you don’t need to use the funds immediately, consider investing the money for future healthcare costs in retirement.


Stock Options and Employee Stock Purchase Plans (ESPPs)


Stock options and ESPPs can be a fantastic way to build wealth, but they require careful planning:


  • Understand the Terms: Know the vesting schedule, the exercise price, and any stock selling restrictions.
  • Tax Implications: Be aware of the tax implications of exercising options or selling ESPP shares. Timing can significantly impact your tax bill.
  • Diversification: Avoid having too much of your portfolio tied up in your employer’s stock. While it's great to have faith in your company, you want to avoid risking your financial future on just one stock.


Evaluating Life and Disability Insurance


Life is unpredictable, and having adequate insurance coverage can provide peace of mind for you and your loved ones. Many employers provide basic group life insurance to their employees for free or at a heavily subsidized rate. However, the coverage amount is usually just 1-2 times your annual salary, which may not be enough for your needs. Review these options carefully and determine if they meet your needs or if you require additional coverage.


Here’s how to make sure you’re adequately covered:


  • Coverage Amount: Assess if the coverage provided by your employer is sufficient. You may need additional coverage to protect your family’s financial future.
  • Supplemental Policies: Consider purchasing supplemental life or disability insurance if your employer’s policy doesn’t meet your needs.
  • Beneficiary Designations: Regularly review and update your beneficiary designations to ensure they reflect your current wishes.


Take Advantage of Other Awesome Perks


We've covered some of the essentials, but there are so many other valuable employee benefits that can help you make the most of your earnings:


  • Employer-paid training, education, and professional development opportunities
  • Commuter benefits to save on public transportation, parking, carpooling options, etc.
  • Employee discounts on products, services, travel, and more
  • Childcare reimbursement
  • Tuition reimbursement
  • Generous paid time off, parental leave, sabbaticals and more
  • Employee Assistance Programs (EAPs) provide confidential counseling, legal assistance, and other valuable resources to help you navigate personal or work-related challenges.


The list goes on and on! But here's the catch — you have to take the time to learn about your benefits and what's available to you. Don't just let these valuable benefits go to waste!


Let Five Pine Help You Make the Most of Your Benefits


When it comes to your finances, small overlooked areas of inefficiency can add up to a staggering amount of money over time. Your employee benefits package represents a prime opportunity to gain additional income if you take advantage of them.


By thoroughly reviewing your available benefits each year and taking full advantage of them, you could easily inject a 10-30% raise into your household's finances. For a high-earner making $500,000+ annually, we're talking about tens of thousands of dollars in additional wealth-building power.


Of course, maximizing your benefits takes a little work and conscientious planning up front. However, the incredible value

you'll get in return is well worth the effort. After all, you've earned these benefits through your hard work and professional success.


If you need help figuring out where to start or could use some guidance, reach out anytime. As your financial advisors, we're here to help you maximize every possible resource available to you. 


To schedule a meeting, email us at info@fivepinewealth.com or call us at 877.333.1015. At Five Pine Wealth Management, we want to ensure you're taking full advantage of your employee benefits package!

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You've Maxed Your 401(k). Now What? A Strategic Guide for High Earners

January 26, 2026
Key Takeaways High earners maxing out 401(k)s at $24,500 are only saving about 8% of a $300,000 income in their primary retirement account. The mega backdoor Roth strategy can increase total 401(k) contributions to $72,000 annually with tax-free growth. A comprehensive approach can create nearly $3 million in additional retirement wealth over 20 years. It's 2026. You're checking all the boxes. You're earning upwards of $300,000 annually, and you're maxing out your 401(k) every year. You've reached the $24,500 contribution limit and feel confident about securing your financial future. Then you realize $24,500 represents less than 8% of your income. Over 20 years, this gap adds up to millions in lost opportunity. Thankfully, you're not stuck with the basic 401(k) playbook. There are sophisticated strategies beyond your contribution limit. 5 Strategic Moves for High Earners with Maxed-Out 401(k)s Here are five sophisticated strategies that can help you build wealth beyond your basic 401(k) contributions. All projections assume a 7% average annual return and are estimates for illustrative purposes. 1. Mega Backdoor Roth Contributions If your employer's 401(k) plan allows after-tax contributions, this could be your biggest opportunity. With employee contributions, employer match, and after-tax contributions, the combined 401(k) limit for 2026 is $72,000 ($80,000 if you're 50 or older). The mega backdoor Roth works because you immediately convert those after-tax contributions into a Roth account, where they grow tax-free forever. The catch: Not all employers offer this option. You need a plan that permits after-tax contributions and in-service Roth conversions. The impact: The available space for after-tax contributions depends on your employer match. With a typical employer match of 3-6% (roughly $10,000-$21,000 on a $350,000 salary), you could contribute approximately $26,500-$37,000 annually. At 7% average returns over 20 years, this creates approximately $1.1-$1.5 million in additional tax-free retirement savings. 2. Donor-Advised Funds for Charitable Giving If you're charitably inclined, donor-advised funds (DAFs) offer a way to bunch several years of charitable contributions into one tax year, maximizing your itemized deductions while still spreading your giving over time. You get an immediate tax deduction for the full contribution, but you can recommend grants to charities over many years. The funds grow tax-free in the meantime. The catch: Once you contribute to a DAF, the money is irrevocably committed to charity. You can't get it back for personal use. The impact: Contributing $50,000 to a DAF in a high-income year (versus giving $10,000 annually) can create immediate federal tax savings of $15,000-$18,500 while still allowing you to support the same charities over five years. 3. Taxable Brokerage Accounts with Tax-Loss Harvesting Once you've maximized tax-advantaged accounts, strategic taxable investing becomes your next move. The key is working with a financial advisor who implements systematic tax-loss harvesting throughout the year. Tax-loss harvesting involves selling investments at a loss to offset capital gains elsewhere. Done strategically, this can save thousands in taxes annually. The catch: Long-term capital gain rates (0%, 15%, or 20%) are lower than ordinary income tax rates, but you're still paying taxes on gains. It's less tax-efficient than retirement accounts, but far better than ignoring tax optimization. The impact: For high earners in the 35-37% ordinary income brackets, the difference between long-term capital gains (20%) and ordinary rates is significant. Effective tax-loss harvesting on $50,000 in annual gains over 20 years could save $150,000+ in taxes. 4. Health Savings Account (HSA) Triple Tax Advantage HSAs offer a unique triple tax benefit: tax-deductible contributions, tax-free growth, and tax-free withdrawals for qualified medical expenses. With 2026 contribution limits of $4,400 for individuals and $8,750 for families, this adds another powerful layer to your strategy. You can invest HSA funds just like an IRA and let them grow for decades. After age 65, you can withdraw the funds for any purpose, medical or otherwise. The catch: You must have a high-deductible health plan to qualify for an HSA. After age 65, non-medical withdrawals are taxed as ordinary income (like traditional IRA distributions), but you still benefit from the upfront deduction and decades of tax-free growth. The impact: Contributing the family maximum ($8,750) annually for 20 years at a 7% average annual return creates approximately $355,000-$360,000 in tax-advantaged savings. 5. Backdoor Roth IRA Contributions Not to be confused with mega backdoor Roth contributions! Even if your income exceeds the Roth IRA contribution limits, you can still fund a Roth through the backdoor method: make a non-deductible contribution to a traditional IRA, then immediately convert it to a Roth IRA. The catch: If you have existing traditional IRA balances, the pro-rata rule complicates things. You may want to consider rolling those funds into your 401(k) first if your plan allows. The impact: Contributing $7,000 annually through the backdoor Roth for 20 years at 7% average annual return creates approximately $285,000-$290,000 in tax-free retirement savings. What Compounding These Strategies Looks Like Over 20 Years Let’s look at approximate outcomes based on a 7% average annual return. 401(k) Only: Annual contribution: $24,500 Total after 20 years: ~$1M 401(k) + Mega Backdoor Roth: Annual contribution: $72,000 Total after 20 years: ~$3M Note: Mega backdoor Roth space varies based on your employer's match. These calculations assume you're maximizing the total annual limit. Comprehensive Approach (under age 50): Mega Backdoor Roth: ~$3.0M HSA: ~$350K-$360K Backdoor Roth IRA: ~$285K-$290K Strategic taxable investing with tax-loss harvesting Total retirement savings: ~$3.6M+, plus taxable investments Comprehensive Approach (ages 50-59): With higher contribution limits and catch-up contributions, total retirement savings can reach ~$4M+ over 20 years. Comprehensive Approach (ages 60–63 with enhanced catch-up contributions) Higher contribution limits during peak earning years allow for meaningful acceleration of retirement savings. The exact impact depends on timing, contribution duration, and existing balances. The Bottom Line The difference between stopping at your basic 401(k) and implementing a comprehensive strategy can approach $3 million or more in additional retirement wealth over time. Why Strategic Coordination Matters These aren't either/or decisions. The most effective approach coordinates multiple strategies while ensuring everything works together. At Five Pine Wealth Management , we help high-earning clients build comprehensive plans that go beyond the 401(k). We coordinate your employer benefits, tax strategies, and investment accounts to create a cohesive approach that maximizes your wealth-building potential. This requires working across several areas: Analyzing your employer's 401(k) plan for mega backdoor Roth opportunities Implementing systematic tax-loss harvesting in taxable accounts Coordinating Roth conversions and backdoor contributions Optimizing your HSA as a long-term retirement vehicle Ensuring charitable giving strategies align with your tax situation Maximizing catch-up contributions when you reach milestone ages As fiduciary advisors, we're legally obligated to act in your best interest. That means we're focused on strategies that serve your goals, not products that generate commissions. Ready to see what's possible beyond your 401(k)? Email us at info@fivepinewealth.com or call 877.333.1015 to schedule a conversation about your specific situation. Frequently Asked Questions (FAQs) Q: Does my employer's 401(k) plan automatically allow mega backdoor Roth contributions? A: No. You need a plan that permits after-tax contributions and in-service conversions to Roth. Check with your HR department. Q: How do I prioritize which investment strategies to use? A: Generally, maximize employer match first (it's free money), then fully fund your 401(k), explore Mega Backdoor Roth if available, max out your HSA, consider backdoor Roth IRA contributions, and then move to taxable accounts with tax-loss harvesting. We can help determine the right sequence for your circumstances.

What's the Best Asset Allocation for Someone 10 Years Away from Retirement?

December 22, 2025
Key Takeaways Your guaranteed income sources (pensions, Social Security) matter more than your age when deciding allocation. Retiring at 65 doesn't mean your timeline ends. You likely have 20-30 years of investing ahead. Think in time buckets: near-term stability, mid-term balance, long-term growth. You're 55 years old with over a million dollars saved for retirement. Your 401(k) statements arrive each month, and you find yourself questioning whether your current allocation still makes sense. Should you be moving everything to bonds? Keeping it all in stocks? Something in between? There's no single "correct" asset allocation for everyone in this position. What works for you depends on factors unique to your situation: your retirement income sources, spending needs, and risk tolerance. Let's look at what matters most as you approach this major life transition. Why Asset Allocation Changes as Retirement Approaches When you’re 30 or 40, your investment timeline stretches decades into the future. When you’re 55 and looking to retire at 65, that equation changes because you’re no longer just building wealth: you’re preparing to start spending it. You need enough growth to keep pace with inflation and fund decades of retirement, but you also need stability to avoid the need to sell investments during market downturns. At this point, asset allocation 10 years before retirement is more nuanced than a simple “more conservative” approach. Understanding Your Actual Time Horizon Hitting retirement age doesn't make your investment timeline shrink to zero. If you retire at 65 and live to 90, that's a 25-year investment horizon. Think about your money in buckets based on when you'll need it: Time Horizon Investment Approach Example Needs Short-Term (Years 1-5 of Retirement) Stable & accessible funds Monthly living expenses, healthcare costs, and early travel plans Medium-Term (Years 6-15) Moderate risk; balanced growth Home repairs, care and income replacement, and helping grandchildren with college Long-Term (Years 16+) Growth-oriented with a Long-term care expenses, decades-long timeline legacy planning, and extended longevity needs This bucket approach helps you think beyond simple stock-versus-bond percentages. Asset Allocation 10 Years Before Retirement: Starting Points While there's no one-size-fits-all answer, here are some reasonable starting frameworks: Conservative Approach (60% stocks / 40% bonds) : Makes sense if you have minimal guaranteed income or plan to begin drawing heavily from your portfolio upon retirement. Moderate Approach (70% stocks / 30% bonds) : Works well for those with some guaranteed income sources, moderate risk tolerance, and a flexible withdrawal strategy. Growth-Oriented Approach (80% stocks / 20% bonds) : Can be appropriate if you have substantial guaranteed income covering basic expenses and the flexibility to reduce spending temporarily as needed. Remember, these are starting points for discussion, not recommendations. 3 Steps to Evaluate Your Current Allocation Ready to see if your current allocation still makes sense? Here's how to start: Step 1: Calculate your current stock/bond split. Pull your recent statements and add up everything in stocks (including mutual funds and ETFs) versus bonds. Divide each by your total portfolio to get percentages. Step 2: List your guaranteed retirement income. Write down income sources that aren't portfolio-dependent: Social Security (estimate at ssa.gov), pensions, annuities, rental income, or planned part-time work. Total the monthly amount. Step 3: Calculate your coverage gap. Estimate monthly retirement expenses, then subtract your guaranteed income. If guaranteed income covers 70-80%+ of expenses, you can be more growth-oriented. Under 50% coverage means you'll need a more balanced approach. When to Adjust Your Allocation Here are specific triggers that signal it's time to review and potentially adjust: Your allocation has drifted more than 5% from target. If you started at 70/30 stocks to bonds and market movements have pushed you to 77/23, it's time to rebalance back to your target. Your retirement timeline changes significantly. Planning to retire at 60 instead of 65? That's a trigger. Every two years of timeline shift warrants a fresh look at your allocation. Major health changes occur. A serious diagnosis that changes your life expectancy or healthcare costs should prompt an allocation review. You gain or lose a guaranteed income source. Inheriting a pension through remarriage, losing expected Social Security benefits through divorce, or discovering your pension is underfunded. Market volatility affects your sleep. If you're checking your portfolio daily and feeling genuine anxiety about normal market movements, your allocation might be too aggressive for your comfort, and that's a valid reason to adjust. Beyond Stocks and Bonds Modern retirement planning involves more than just deciding your stock-to-bond ratio. Consider international diversification (20-30% of your stock allocation), real estate exposure through REITs, cash reserves covering 1-2 years of spending, and income-producing investments such as dividend-paying stocks. The Biggest Mistake: Becoming Too Conservative Too Soon Moving everything to bonds at 55 might feel safer, but it creates two significant problems. First, you're almost guaranteeing that inflation will outpace your returns over a 30-year retirement. Second, you're missing a decade of potential growth during your peak earning and saving years. The difference between 60% and 80% stock allocation over 10 years can mean hundreds of thousands of dollars in portfolio value. Being too conservative can be just as risky as being too aggressive, just in different ways. Questions to Ask Yourself As you think about your asset allocation for the next 10 years: What percentage of my retirement spending will be covered by Social Security, pensions, or other guaranteed income? How flexible is my retirement budget? Could I reduce spending by 10-20% during a market downturn? What's my emotional reaction to seeing my portfolio drop 20% or more? Do I plan to leave money to heirs, or is my goal to spend most of it during retirement? Your honest answers to these questions matter more than your age or any generic allocation rule. Work With Professionals Who Understand Your Complete Picture At Five Pine Wealth Management, we help clients work through these decisions by looking at their complete financial picture. We stress-test different allocation strategies against various market scenarios, coordinate withdrawal strategies with tax planning, and help clients understand the trade-offs between different approaches. If you're within 10 years of retirement and wondering whether your current allocation still makes sense, let's talk. Email us at info@fivepinewealth.com or call 877.333.1015 to schedule a conversation. Frequently Asked Questions (FAQs) Q: What is the rule of thumb for asset allocation by age? A: Traditional rules like "subtract your age from 100" are oversimplified. Your allocation should be based on your guaranteed income sources, spending flexibility, and risk tolerance; not just your age. Q: Should I move my 401(k) to bonds before retirement? A: Not entirely. You still need growth to outpace inflation. Gradually shift toward a balanced allocation (60-80% stocks, depending on your situation) and keep 1-2 years of expenses in stable investments. Q: What's the difference between stocks and bonds in a retirement portfolio?  A: Stocks provide growth potential to keep pace with inflation but come with volatility. Bonds offer stability and income but typically don't grow as much.