pre-retirees

Retirement Is Coming Faster Than You Think. Are You Ready?

You’ve worked hard to get here. You’ve saved, invested and planned for the future. But as retirement approaches, the stakes get higher. The decisions you make now will determine the life you live for decades to come. Will you retire with confidence—or with questions?

At Sherpa Wealth Strategies, we guide pre-retirees like you through the crucial final stretch before retirement. We help you optimize your savings, navigate complex decisions and ensure your money lasts as long as you do.

If you’re within 10 years of retirement and have at least $1 million in investable assets, we should talk.

Does This Sound Like You?

You’ve built a strong financial foundation, but you want to be sure you’re truly on track.
You’re balancing competing priorities—enjoying life today, helping children or grandchildren with education, saving for retirement and caring for aging parents.
You know you don’t get a second chance at retirement planning. You want a guide who understands how to structure your wealth for security, freedom and peace of mind.

If this resonates, you’re in the right place.

What We Do for Pre-Retirees

We Turn Uncertainty Into Clarity 
You have questions. We have answers. How much will you need? When should you take Social Security? How do you optimize taxes? We build a customized plan so you can retire without guesswork.
We Align Your Money With Your Life 
Retirement isn’t just about money—it’s about freedom, family and fulfillment. We help you design a financial strategy that lets you live fully today while securing your future.
We Help You Avoid the Big Mistakes 
One wrong move—claiming Social Security too early, mismanaging investments, or underestimating healthcare costs—can derail your retirement. We ensure you don’t fall into common traps.

Top Questions Pre-Retirees Ask About Their Financial Future: FAQs

How do I know if I have enough to retire?

We run detailed projections based on your income needs, inflation, taxes, healthcare and investment strategy. No vague guesses—just data-driven answers.

When should I claim Social Security?

The difference between claiming at 62 vs. 70 can mean hundreds of thousands of dollars over your lifetime. We analyze your options to maximize your benefits.

How do I balance spending now with saving for the future?

Retirement isn’t about sacrifice—it’s about strategy. We help you build a plan that funds your current lifestyle without jeopardizing your future security.

What’s the biggest risk most pre-retirees overlook?

Taxes. Without proper planning, you could end up paying more than necessary in retirement. We help you implement smart tax strategies to keep more of your wealth.

How do I choose the right Medicare plan as I approach retirement?

Selecting a Medicare plan is more complex than it may seem. You’ll need to choose between Original Medicare (Parts A & B) and Medicare Advantage (Part C) and consider whether to add prescription drug coverage (Part D) or a Medigap policy to help cover out-of-pocket costs.

Each path has pros and cons in terms of:

Cost structure (monthly premiums vs. pay-as-you-go)
Provider access (freedom to see any doctor vs. limited networks)
Coverage flexibility (especially if you travel frequently or live in multiple states)

Enrollment deadlines and coverage coordination with employer or retiree health benefits can also impact your decision. We help clients weigh these factors and choose a Medicare strategy that fits both their healthcare needs and retirement lifestyle.

What’s the best way to use my Health Savings Account (HSA) as I transition into retirement?

Your Health Savings Account (HSA) becomes even more valuable as you near retirement. HSAs are the only investment vehicle that offers triple tax advantages: tax-deductible contributions, tax-free growth and tax-free withdrawals for qualified medical expenses.  In retirement, you can use your HSA to pay for:

Medicare Part B, Part D, and Medicare Advantage premiums (not Medigap)
Out-of-pocket costs like deductibles, copays, and dental or vision care
Long-term care expenses (including some insurance premiums)

After age 65, you can even use your HSA for non-medical expenses without penalty (though they’ll be taxed as income). We guide clients on how to invest and time withdrawals to maximize these tax benefits and support long-term health needs.

How should I prepare for the cost of long-term care in retirement?

Long-term care is one of the most overlooked—and expensive—retirement risks. Medicare doesn’t cover most long-term care services like home health aides, assisted living, or nursing home stays. And the costs can easily run into the hundreds of thousands of dollars over time.

There are several ways to prepare:

Traditional long-term care insurance: Pays benefits if care is needed, but premiums can rise and are “use-it-or-lose-it.”
Hybrid life insurance policies: Combine a death benefit with long-term care coverage—unused benefits go to your heirs.
Self-funding strategies: Set aside specific assets earmarked for care, often coordinated with income and tax planning.

We help clients evaluate which approach best fits their financial situation and personal values, so they can protect their assets and ensure quality care without burdening loved ones.