Stepping Stone Wealth

10/30/2026

Tomorrow may be Halloween, but retirement planning doesn’t have to be scary. 🎃

In our first edition our Ask Our Advisors, we’re answering common questions about retirement and the decisions that can come with it.

Watch the video to hear our take. Time stamps below for each question:
1:03 — How do I know if I can afford to retire?
1:43 — What happens with health insurance if I retire before 65?
2:17 — Should I take Social Security as soon as I'm eligible or wait?
2:58 — Where does the money actually come from once my paycheck stops?
3:34 — What if the market drops right before I retire?
4:28 — Will my taxes go down in retirement?
5:06 — Does it still make sense to do Roth conversions after RMDs have started?
5:46 — How do I make sure I don't outlive my money?
6:43 — What surprises people most during their first year of retirement?
7:17 — What's the biggest mistake you see people make in the first five years before retirement?

Legal File #9147365

10/27/2026

Some of the best advice I give sends money out of the portfolio.
Pay down the mortgage. Keep more in cash. Take the trip. Help your children now instead of leaving it to them later.
I've recommended every one of those, and sometimes it means less money invested with us.
My view is simple. It's not my money.
My job is to help you use what you've built to live the life you want. Sometimes that means investing for the future. Sometimes it means spending some of it today, and sometimes it means a choice that makes no sense if you only look at investment returns.
The reason this matters is that the way an advisor is paid can shape what gets recommended. Pay doesn't decide the quality of the advice, but it's fair to ask about it.
The question I come back to is always the same: what is this money supposed to do for the person who owns it?
Building wealth matters. Knowing when to use it matters just as much.

10/20/2026

Before I became a financial advisor, I worked as an actuarial associate. One of the first things that work teaches you is that you can't change one variable and expect the rest of the model to hold still.

Financial lives work the same way.

A Roth conversion looks like a tax decision. It can also affect what your heirs eventually receive and the taxes involved. How an account is titled looks like paperwork, but it can determine whether the trust your attorney drafted controls that money. A beneficiary designation looks like a formality, but it can determine where an account goes, regardless of what your will says.

Each of those decisions usually sits with a different professional. Your CPA, your estate attorney, and your financial advisor are each working on their own part of the model. Each of them can be right about their part while the whole thing stops adding up.

The risk isn't always bad advice. Sometimes it's good advice that nobody checked against the rest of the plan.

That's why I want to know what the CPA is projecting before I recommend anything that changes taxable income, and why the estate documents belong on the table when we talk about which accounts to draw from first.

It gets complicated when these decisions happen in three separate rooms.

Three good answers can still add up to a bad plan.

The work is making them fit.

10/16/2026

Our COO, Jennifer Gray, spent part of this week in Boston at the Jambalaya Group Operations Leader Conference.

If you haven't heard of Jambalaya Group, it's a coaching and consulting firm that works with financial advisory practices. Its focus is helping successful advisors become equally successful business owners. Its annual Operations Leader Conference brings together COOs and operations leaders to share best practices, hear industry updates, and connect with peers.

Jenn also spoke on a panel called "Creating Capacity & Supporting Growth." It's a topic she thinks about every day as she builds the systems and team that let our advisors spend more time with the people they serve.

Jenn, thank you for representing Stepping Stone Wealth and sharing what we've learned along the way!

10/13/2026

There is a kind of financial advice that is technically correct and still leaves someone stuck.

It lays out the options. It explains the tradeoffs. Every fact in it is accurate. And the person who asked for help walks away with more information and the same unmade decision.

I understand why it happens. Presenting options feels safe, because if you never recommend anything, you’re never wrong. But the decisions that matter most in a financial life rarely stay in one lane. They touch taxes, estate documents, cash flow, and family all at once, and when every professional explains their piece and stops there, the decision lands back on the person who came in hoping someone would help carry it.

That’s the part I don’t hand back.

When something is complicated, my job is to hold the whole picture, form a view, and say it out loud: here is what I see, here is what I recommend, and here is why.

If I need the CPA’s read or the attorney’s, I pick up the phone. If my first answer doesn’t hold up, I keep working until one does.

And once a decision is made, I stay involved to help make sure the next steps actually happen.

I’m not always right. I would still rather make a clear recommendation and own it than hand someone a balanced list and call that help.

The reason this matters is that an unmade decision is still a decision. It just doesn’t have anyone’s name on it.

10/07/2026

We're celebrating Camille Gagliardi's 30th year with Ameriprise!

A lot has changed in three decades. What hasn't changed is the standard she set from the start, and our team still lives by it: Relationships First.

For us, that means listening before recommending, bringing the right people into the room, and making sure clients understand the decisions in front of them.

Camille built Stepping Stone Wealth around that idea, and we're proud to carry it forward with her.

Congratulations, Camille, and thank you.

10/05/2026

Today we're celebrating Neil Holt's 4-year anniversary with Stepping Stone Wealth!

Before financial planning, Neil spent years in Connecticut schools. You can still hear that background in the way he works: explain the why, slow down the decision, and make sure the person across the table understands what comes next.

We're grateful for the way he keeps growing alongside our team, from earning his CFP® designation to leading our work with educators planning for retirement.

Happy anniversary, Neil.

Visit his advisor website to learn more about Neil: https://bit.ly/4jGQgdn

09/28/2026

You might see a familiar face on TV this fall. 📺

Stepping Stone Wealth commercials are airing now through December across the greater Hartford area, including Hartford, Manchester and Enfield.

Where to watch for us: 🏈 Sports: ESPN, ESPN2, NESN, NBC Sports Boston, NFL Network, FS1 and Golf Channel 📈 News and business: CNBC, CNN, Fox News, Fox Business and MSNOW 🏡 Lifestyle and entertainment: HGTV, Food Network, Magnolia, Bravo, Comedy Central, History, TNT, USA and more

Most spots air during the morning news and evening sports.

If you catch one, let us know in the comments or send us a message. We'd love to hear where you saw it!

09/22/2026

How might the 2026 midterm elections affect markets and your investment strategy? Explore key issues, historical trends and potential sector impacts.

Explore potential market, sector and investing implications of the 2026 midterm elections.

09/10/2026

Great companies don't happen by accident.

Ameriprise Financial was named one of Newsweek's America's Greatest Companies of 2026.

This recognition reflects the people, culture and client-focused approach that help make Ameriprise stand out.

Learn more about what sets Ameriprise apart: https://bit.ly/3df9a5L