Featured entries from our Journal

Signal vs. Noise: Stock Market Concentration Concerns

The Player or the House?

We’re in the Hospitality Business

Client-Exclusive Webinar with David Booth, Co-Founder and Chairman of Dimensional

A Good Estate Plan Should Make Life Easier

Category: Planning

Free Money from Uncle Sam for your Baby’s Retirement

a woman holding a baby and smiling
Nell Schiffer and her baby Merrill
Trump Accounts Are Live. Here’s Our Take.

When Congress creates a new savings account, there’s usually a lot of excitement, a lot of headlines, and eventually a lot of confusion. Trump Accounts are no different.

Our view is pretty simple: If your family qualifies for the free $1,000, take it.
After that, pause before directing additional savings there. In many cases, we still believe there are better tools available.

What is a Trump Account?

A Trump Account is a new tax-advantaged investment account for children under age 18. The investments are intentionally simple: low cost, broadly diversified U.S. stock index funds.

Children born between January 1, 2025, and December 31, 2028, who meet the eligibility requirements, may receive a one-time $1,000 contribution from the federal government. Family members can also make annual contributions, subject to contribution limits.

Who should pay attention?

If you have:
• A child born between January 1, 2025 and December 31, 2028 (like me)
• A grandchild in that age range
• A niece or nephew whose parents may not have heard about the program

It’s worth making sure someone claims the government’s contribution.

Our Perspective

This is where we think it’s helpful to separate the headline from the planning.
The headline is the free $1,000. The planning question is whether this should become your primary savings vehicle. For most families, our answer is no. If your goal is education, a 529 plan is often the better choice. If your goal is flexible gifting, a custodial or trust investment account may provide greater flexibility. If your goal is retirement, maximizing your own retirement accounts is frequently the highest impact decision you can make. Trump Accounts are another tool, not a replacement for the others.

One Interesting Planning Opportunity

One feature we do like is that these accounts eventually transition into something that functions much like a Traditional IRA.

That creates the possibility of converting the account to a Roth IRA during early adulthood, when many young adults have relatively little taxable income. Decades of tax-free growth after a low tax Roth conversion could make that initial $1,000 much more valuable over a lifetime. It is too early to know exactly how often this strategy will make sense, but it is an opportunity we will be watching closely.

The Bottom Line

At Hill, we don’t chase headlines.
We look for opportunities to make small, intelligent decisions that compound over decades.
For eligible families, claiming a free $1,000 is one of those decisions.

How to Open a Trump Account

If you have a child or grandchild who may be eligible, here’s how to get started.

Step 1: Confirm eligibility.

Children born between January 1, 2025, and December 31, 2028, who are U.S. citizens with a valid Social Security number, may qualify for the government’s $1,000 contribution.

Step 2: Complete the enrollment process.

Parents or legal guardians will need to complete the required enrollment through the IRS and Treasury’s Trump Account program. If your child is eligible, this establishes their ability to receive the government’s contribution.

Step 3: Activate the account.
Once eligibility has been verified, you’ll activate the account through an approved provider. The Treasury will then deposit the $1,000 for eligible children, and family members can begin making additional contributions if they choose.
As with many new government programs, the rollout is still evolving. We expect additional financial institutions to begin offering Trump Accounts over time, making the process even more straightforward.

Helpful Resources
• IRS Trump Accounts page for eligibility requirements, FAQs, and enrollment information.
• TrumpAccounts.gov for program updates, participating providers, and account activation instructions.
• Recommended reading from the New York Times on this topic (free NYT gift link, available for a limited time)

If you have questions about whether a Trump Account fits into your family’s broader financial plan, we’re here for you.

Pay Yourself First

an illustrations of a man picking up coins off the ground

Is your cash working as hard as it could be? Many checking and savings accounts still pay very little interest. That’s why we recommend Flourish, a high-yield cash account for everyday cash and short-term savings (we use it ourselves, too). It keeps your money accessible while earning a competitive rate. 

For a limited time: If you set up direct deposit into Flourish before the end of 2026, you’ll earn a boosted interest rate for your first 90 days. It costs nothing and only takes a few minutes to activate.

After the promotional period ends, your cash will continue to earn Flourish’s competitive standard rate rather than sitting in an account paying little or no interest. 

At Hill, we believe the best financial strategies are often the simplest ones. Small changes like earning more on your cash and automating good financial habits can make a meaningful difference over time.

If you’d like help getting started with Flourish or setting up direct deposit, recurring transfers, and other automations, we’re happy to help. Please reach out to us.

A Book That Changed How I Think About Aging

two adults sitting on a bench looking out

A few years ago, a family member transitioned to assisted living. The decision felt difficult for her, like a loss of independence. She fought it hard. But once she settled in, something unexpected happened: she found routine, connection, and purpose again.

Watching that shift reframed how I think about financial planning.

As planners, we often approach aging and retirement through a practical lens. We focus on the details: health care plans, long-term care, estate documents, and whether the financial plan can support the years of spending ahead.

Those things matter. But quality of life matters too. So does preserving a sense of agency as your needs, abilities, and priorities change.

Earlier this year, during a conversation about a client’s transition into assisted living, his daughter suggested I read Being Mortal by Atul Gawande.

I’m glad she did. The book changed how I think about the later stages of life and the role planning should play in them.

Here are three key lessons:

1. Independence Matters More Than Perfect Safety
One of the book’s core ideas is that many senior living decisions prioritize safety over autonomy. Safety matters, of course. But losing independence can take a real toll on wellbeing.

The best living environments preserve choice: how you spend your day, who you’re around, and what gives you meaning.

We’ve seen this with clients who explore senior communities early, before they need them. Beginning earlier gives families more agency over the decision. It can also help clients gain more life through social connection, activities, and less stress about home maintenance.

2. Purpose Is Fundamental to Wellbeing
Gawande highlights research showing that even small responsibilities, like caring for a plant, can improve wellbeing and longevity for older adults.

The lesson is simple: people need purpose. They need a reason to get out of bed in the morning.

Financial independence is important. But planning should also ask what replaces the structure and meaning that work once provided. People who thrive in this phase often stay connected to hobbies, community, family, or roles where they still feel needed.

3. Define Quality of Life, Before a Crisis
Being Mortal reminds us that our definition of quality of life changes over time.

When we’re younger, it may mean freedom and adventure. Later, it may mean staying close to family, maintaining familiar routines, or enjoying a favorite meal with people we love.

Many families avoid talking about aging until a crisis forces decisions. The book encourages asking better questions sooner:

• What are your fears and goals as you get older?
• What tradeoffs would you be willing, or unwilling, to make?

In our advisory role, we’ve seen how helpful it is when families have these conversations before a medical event or major transition. When your values are clear, decisions become less about guessing and more about honoring what matters most.

Planning for aging doesn’t mean expecting the worst. It means getting clear about what matters most, so that when decisions come, they reflect your values instead of default choices.

At Hill, we believe financial planning is about more than numbers. Taking the long view means helping people live well across every stage of life, with clarity, confidence, and peace of mind.

If this sparks a conversation about aging, independence, or planning for later life, we’re here to help you or someone you care about talk through it. Reach out any time here.

Featured entries from our Journal

Signal vs. Noise: Stock Market Concentration Concerns

The Player or the House?

We’re in the Hospitality Business

Client-Exclusive Webinar with David Booth, Co-Founder and Chairman of Dimensional

A Good Estate Plan Should Make Life Easier

Hill Investment Group