Retirement and legacy planning in the “messy middle”: Make savings last and leave a legacy

Most couples in their 50s and early 60s don’t feel wealthy — even when the numbers say otherwise. Maybe you’ve recently crossed the million-dollar mark after decades of saving, or a recent inheritance pushed your account balances higher than you ever expected. On paper, you have more money saved for retirement than you ever imagined and quitting your job finally feels within reach. But somehow, your finances still feel fragile. The questions start piling up:

“Will our retirement savings last as long as we need them to?”
“What if one of us needs long-term care?”
“Will there be anything left for the kids?”
“How do we make sure they don’t go through the mess we just went through with our parents’ estate?”

If that sounds familiar, you’re not alone. Many couples come to me at this exact crossroads — grateful for what they have, but worried about how easily it could all disappear. Their goal is simple: enjoy a comfortable retirement now and leave something meaningful to their kids later.

The good news is that both are possible. With a Rock-Solid Family Wealth Plan grounded in communication, protection, and clarity, you can make confident decisions about your future and give your children the gift your parents may not have left you – a meaningful, drama-free inheritance.

Many families combine retirement and legacy planning in a single, structured financial plan, which is exactly how Berkshire Money Management helps clients align retirement income security with long-term legacy goals.

Lessons learned the hard way: What parents take away from their own inheritance

It’s not uncommon for couples in their 50s and 60s to cross the $1 million retirement savings threshold through inheritance. If your parents or in-laws have passed away, you may already know just how emotionally charged and complicated estates can be. I’ve heard stories like these countless times:

• Siblings who stopped speaking because they disagreed about dividing assets.
• Families who spent months in probate, losing their inheritance to probate fees and opportunity costs.
• Adult children stuck trying to pick up the pieces because their parents didn’t update their wills, account beneficiaries, or other estate documents.
• Inheritances drained in a few years, not because anyone was irresponsible, but because no one was prepared to manage large sums of money.
• Confusion over what Mom or Dad “would have wanted”, simply because the parents never shared their intentions.
• Family homes lost forever because they weren’t held in trust.

If your experience was anything like this, it’s likely already shaping how you’re approaching your own retirement and legacy planning. The good news is that, by taking action now, you can make things a lot easier for your own kids.

Retirement and legacy planning: the dual challenge for couples at $1 million

Couples in their 50s and 60s with $1 million to $2 million saved typically find themselves balancing two major goals:

1. Ensuring your own retirement is secure for 20–30 years or more
   A million dollars is a hefty sum, but without careful planning, it can run out faster than you might think.
2. Protecting what’s left for your children and grandchildren
   End-of-life expenses, taxes, probate, and family infighting can destroy the legacy you envisioned.

The solution for both of these challenges is proactive planning. To avoid running out of money in retirement, you need income you can count on, an investment strategy that supports your lifestyle, and a clear understanding of how long your assets will last. To protect your legacy for your children, you’ll need an estate plan to legally protect your wealth and a plan to convey your wishes to the next generation.

In my experience, it’s easier than you may think to achieve both goals. Balancing retirement income and legacy protection typically benefits from complete financial planning, which Berkshire Money Management provides for many families in this stage of life.

How a Rock-Solid Family Wealth Plan helps families with $1 million to $2 million create a plan for both retirement and legacy

When building a Rock-Solid Family Wealth Plan for families in your situation, we focus first on the Cornerstones that make the biggest difference.

1. Communication gives your heirs clarity about your wealth.
   Communication is the most critical Cornerstone of family wealth planning for every family, regardless of how much money is in the bank. Open, honest communication prevents conflict and confusion in every part of your financial and estate plan.
2. Risk Reduction protects what you have from unnecessary loss.
   $1 million is a lot of money on paper, but injury, illness, lawsuits, and other risks can reduce your nest egg to nothing in a heartbeat. It’s essential that you guard your family’s wealth with right-sized insurance, trusts, and other protections.
3. Plans that fit your lifestyle are easier to keep.
   Your wealth should be a source of strength, not stress. A complete financial plan can help you feel confident about enjoying the lifestyle you want today while still leaving the gift you envision for your kids and grandkids later.

Touchstones help you make high-stakes decisions about your family’s money

We encourage families to create their own unique Touchstone questions to help them turn their values into actions. Once you’ve identified the values that matter most to your family, you can turn each into a guiding question – a Touchstone – that you and your family can return to whenever you find yourselves at a financial crossroads. For example:

• Will this choice protect our long-term retirement income?
• Does this reduce the burden on our kids later?
• Does this simplify our estate or complicate it?
• Are we preparing our kids emotionally and practically?
• Does this help us maintain flexibility as we age?

Your Touchstones can be used to guide decisions about gifting, vacation planning, home purchases, charitable giving, and more. And as your family’s values shift, your Touchstones should change, too.

The keystone of family wealth: your estate plan

Communication, risk reduction, and lifestyle are important Cornerstones for family wealth, and your Touchstones will help you stay on track throughout the years, but let’s not forget the most critical tool for protecting your assets for the next generation: your estate plan.

At $1 million or $2 million, your estate plan won’t look like Kevin Bacon and Kyra Sedgewick’s or Oprah and Stedman’s, but your financial advisor and estate planning attorney will likely recommend a few key tools:

• Revocable living trust to avoid probate
• Updated beneficiary designations and transfer-on-death accounts
• Incentive provisions in trusts to encourage saving, education, or steady employment
• Long-term care planning so medical expenses don’t wipe out your legacy
• Provisions for pets, which many couples in this stage of life include alongside their heirs

These tools add clarity and reduce the chances of conflict, waste, or surprises.

The ultimate goal: retirement security for you, inheritance clarity for your kids

All of this planning comes down to two simple goals: making sure you never run out of money and that your kids never deal with the stress and confusion you faced when settling your own parents’ estate. That’s the heart of retirement and legacy planning at this level. You don’t need a complicated system or a team of highly-paid lawyers. You just need a coordinated retirement and legacy plan that reflects your values, protects your nest egg, and sets clear expectations for the next generation.

When families do this work, something shifts. Retirement starts to feel less like a math problem and more like a stage of life to enjoy. And the legacy you leave your children becomes a blessing, not a burden or a mystery, and certainly not a source of conflict.

Frequently asked questions

1. How much can I safely withdraw in retirement if I have around $1–2 million?

A practical starting point is to keep annual withdrawals around 4%, adjusted for inflation. That means a $1.5M portfolio might generate $60,000 per year of sustainable withdrawals. The right rate depends on your age, health, spending needs, Social Security income, and investment strategy. At Berkshire Money Management, we help clients create a Paycheck Replacement Plan that maps out a predictable income for every year of your retirement.

2. What’s the simplest way to make sure my kids avoid probate when we pass away?

The most effective tools are:

• A revocable living trust
• Updated beneficiary designations on retirement accounts
• Transfer-on-death (TOD) designations on taxable accounts

These typically allow assets to pass directly to your heirs without court delays. For many families at the $1-2 million level, simply getting these three components in place eliminates most probate challenges and preserves more for the next generation.

3. How do I protect my retirement savings from long-term care costs?

A long-term care event in Massachusetts can cost $100,000 or more per year. Three common strategies to protect your retirement savings include:

• Purchasing long-term care insurance or a hybrid LTC/life policy
• Using certain trust structures to protect assets while maintaining access
• Building LTC costs directly into your retirement income plan

Planning early—ideally in your 50s or early 60s—gives you the most options at the lowest cost. Consult with your financial advisor about which long-term care options may be best for you.

4. What steps should I take now to make my children’s inheritance straightforward and stress-free?

To minimize conflict and confusion later, focus on four actions:

1. Document your wishes clearly in an updated will and trust.
2. Simplify your accounts—fewer institutions means fewer headaches.
3. Talk with your children about your goals and intentions.
4. Create a “what to do” list (key contacts, policies, accounts, and instructions). At BMM, we created our own comprehensive estate organizer, lovingly called the “death binder.” If you’d like a copy, send us an email at info@berkshiremm.com.

Most of the estate nightmares adult children face come from missing paperwork, inconsistent instructions, or unclear intentions—not from complicated finances.

5. How can we make sure there’s something left for our kids while still enjoying retirement?

The most reliable approach is to combining retirement and legacy planning is to build a plan that balances three numbers:

• What you need to live comfortably today
• What you must reserve for future healthcare and long-term care
• What you want to leave behind

From there, your advisor can create a distribution strategy—often blending Social Security timing, IRA withdrawals, Roth conversions, and investment income—that extends the life of your portfolio while preserving the legacy you care about.

Plan for your retirement and you legacy with confidence!

If you’re facing the dual challenge of needing to stretch your retirement savings and wanting to leave a meaningful inheritance to your kids, you’re not alone! Berkshire Money Management has been helping families create actionable plans for their retirement and their legacy for more than two decades, and we want to do the same for yours.

The first step is a free 15-minute phone call with one of our licensed financial advisors.