Are You Giving the Wrong Way in Retirement?

Confessions of a Financial Advisor

The Moment That Changed How I See Generosity

My wife Natasha and I had just finished a wonderful three-day drive up the Oregon coast. As we made our way to the Seattle airport, I already missed the winding curves of the mountains overlooking the Pacific Ocean. 

We pulled off at a red light to fill up the rental car before our flight, and a familiar sight greeted our eyes. A homeless man stood at the corner holding a sign that read: Need help. Need money for food. 

The person to my right looked down into his lap, avoiding eye contact. Another driver was glued to her phone, pretending not to notice. The man in front of me rolled down his window and handed the gentleman a ten-dollar bill. The homeless man nodded. The light turned green. The driver pulled away—maybe never to see him again. 

Now, I can only speculate, but I imagine that man felt like he had done his part. He’d contributed. Helped someone in need. And in a way, he had. 

But I was about to witness the rest of the story. 

We pulled into the gas station. Natasha headed to the restroom while I pumped gas, and then I stood inside waiting for her to freshen up before our flight. That’s when the homeless man walked into the store holding the same ten-dollar bill. He nodded to the cashier like they’d seen each other before. 

And then he asked for a lottery ticket and a pack of Marlboros. 

That was it. Ten dollars gone. No food. 

Are We Helping Others—or Ourselves?

That moment stuck with me. 

Because both men in that moment got what they wanted. The man in the car wanted to feel generous. The homeless man wanted what he wanted in that moment—a shot at better luck and a familiar crutch. 

But here’s the truth: The gift wasn’t lasting. It wasn’t leveraged. And honestly, it wasn’t very loving. 

That may sound harsh. But is it true? 

If your giving doesn’t help someone make real progress in their life… are you helping them, or just helping yourself feel better? 

The Problem with Traditional Giving in Retirement

That moment helped shape how we guide generosity at SWAN Capital…

It challenged me to ask deeper questions—and to help others do the same. 

A Smarter Retirement Giving Strategy

At SWAN Capital, we believe your retirement years are the best years to give. Not just because you’ve saved well, but because you finally have the margin to be intentional. 

Here’s how we guide retirees like you into giving that’s more effective, more joyful, and more aligned with your legacy: 

1. Planned Giving for a Lasting Legacy

One of the simplest and smartest ways to create a legacy is through your beneficiary designations. Too often, retirees leave all accounts equally to heirs—even when that might not be the most tax-efficient strategy. 

One tax-advantaged approach to consider is to: 

• Leave Traditional IRAs (which are taxable) to charities who won’t pay tax on them. 

• Leave Roth IRAs (which are tax-free) to children or grandchildren, who will benefit the most from that tax-free growth. 

You don’t even need to change your will or trust for this strategy. All you need to do is update your IRA or 401(k) beneficiary designations. 

This is what we call a lasting legacy through planned giving. Making sure your generosity is just as tax-smart as your retirement income plan. 

When you give through your estate, make sure you’re giving a hand up, not a handout. Make sure your gift helps someone get on the right path—not fund a joy ride. 

2. Donor-Advised Funds for a Leveraged Legacy

Donor-Advised Funds (DAFs) are one of the most underused and most effective tools retirees can use for tax-smart giving. 

Here’s how they work: 

• You contribute to a DAF (usually in a higher income year) and get an immediate tax deduction. 

• The money stays in the fund, invested and growing tax-free. 

• You then direct grants from the DAF to the charities you care about over time. 

This strategy lets you bunch your giving for immediate tax purposes, grow the fund over time, and make your giving more strategic. 

Let’s say you aren’t giving enough each year to exceed the standard tax deduction. Instead of losing that deduction, you could bundle multiple years of giving into a DAF this year—take the itemized deduction now—and then distribute the funds out over time. 

That’s what we call a leveraged legacy—making your generosity go further by giving smarter. 

3. Volunteering for a Living Legacy

Sometimes, the most meaningful gifts don’t involve writing a check. 

They involve showing up, sleeves rolled up, heart wide open. 

That’s why at SWAN Capital, we host four volunteer events a year, each one supporting a different local charity. We invite all our clients to join us in making a difference. Every year, we rotate the charities to support new causes and reach more people. 

These aren’t just photo ops—these are family legacies being written in real time. 

Bring your kids. Bring your grandkids. Let them see what you value. 

Let them feel the joy that comes from generosity that’s not written on a check, but written on your calendar. Let your loving legacy make an impact for generations to come. 

How to Know If You’re Giving the Right Way

If you’ve ever found yourself wondering: 

• “Am I giving enough?” 
• “Is my giving actually doing something?” 
• “What kind of legacy am I leaving?” 

You’re not alone. 

Let’s talk. 

Schedule a visit with our team at SWAN Capital and let’s walk through your generosity plan.

Whether you plan to give through your will and IRAs, create your own Donor-Advised Fund, and/or volunteer with your family, we would love to sit down with you and help in any way we can. 

Final Thoughts From a Financial Advisor

Confession:

I used to think generosity was mostly about intention.

If your heart was in the right place, that was enough.

But moments like the one I experienced that day reminded me of something deeper—
good intentions don’t always lead to meaningful impact.

And if we’re not careful, our giving can become more about how it makes us feel
than the difference it actually makes in someone else’s life.

The truth is, the best retirement giving strategy isn’t just generous—it’s intentional, thoughtful, and designed to truly help.

It’s about leaving a legacy that lasts.
Not just for a moment… but for generations.

So if you’ve ever wondered whether your giving is really making a difference—
that’s not something to ignore.

It’s something to lean into.

Because at the end of the day,
you’re not just giving money.

You’re shaping your legacy.

COVERING OUR TAIL FEATHERS
Welcome to Swan Capital, LLC (“SWAN”), your friendly neighborhood Registered Investment Adviser (“RIA”). Now, while we may have a fancy title, remember that our registration doesn’t guarantee we’re flying high above the rest. This communication hasn’t been blessed or verified by the United States Securities and Exchange Commission (SEC) or any state securities authority. At SWAN, we believe in giving you personalized investment advice as unique as a swan’s graceful glide. We work with clients in their own states, making sure to play by all the regulatory rules or find the right exceptions. But here’s the scoop: all investments come with risks—like a wild swim in the pond—so no investment strategy can promise profits or protect you from the occasional splashdown. Just remember, past performance is like a cozy old story; it might be nice to reminisce about, but it doesn’t promise what’s coming next. 

SWAN Capital, LLC is an independent firm and is not affiliated with, endorsed by, or sponsored by the Federal Employee Retirement System (FERS) or any government agency. 

Thanks for gliding along with us at SWAN! We’re here to help you soar to new financial heights while ensuring you can truly Sleep Well At Night!