September is Life Insurance Awareness Month, a good a nudge as any to revisit the paperwork nobody loves thinking about. The kids are back in a routine, summer travel is behind you, and the “I’ll get to it” list from earlier this year is still sitting there.
This month, we’re focused on the documents and decisions that protect the people you love ,not because something is wrong, but because “eventually” has a way of arriving sooner than planned.
September: Protect What You Will
🗂️ The Four Documents Everyone Needs
“Estate planning” sounds like something for other people — people with more assets, more complexity, more reasons to bother. In practice, it’s four documents that matter at any net worth:
- A will: says who gets what, and just as important, who takes care of your kids if something happens to you
- A financial power of attorney: names someone to manage your money and pay your bills if you can’t
- A healthcare power of attorney and advance directive: spells out who makes medical decisions for you, and what you’d want them to decide
- Beneficiary designations: the forms on file with your 401(k), IRA, and life insurance, which override whatever your will says
🛡️ Where People Leave Gaps
The documents above are the foundation, but a few other things tend to get overlooked, not because they’re complicated, just because there’s never an obvious moment to deal with them:
- A life insurance review: coverage that made sense at 30 often doesn’t match your life at 45
- Disability insurance: far more likely to be used than life insurance, and far less often in place
- An umbrella liability policy: inexpensive protection once your net worth is worth protecting
- A digital “letter of instruction”: where accounts, passwords, and key documents actually live, for whoever has to find them
- Beneficiary designations you set up a decade ago and haven’t looked at since
“Protecting what you will isn’t about assuming the worst. It’s about making sure the people you love aren’t left guessing.”
From the Studio
Newest Episodes:
This month, we’re talking to a guest who’s built not one but two businesses before turning 25 and figured out how to make them work together. Mary Esposito is the founder of Purple Pear, a crochet brand she started as a teenager, and the creator of Money with Mary, a personal finance platform built around bringing more young women into investing and money conversations.
Newest Episodes:
Episode 16: Cracking the College Admissions Code: Scholarships, Myths & AI with Shellee Howard
This month, we’re talking to a guest who’s helped families collectively earn more than $80 million in scholarships and get thousands of students into some of the most selective schools in the country. Shellee Howard is the founder and CEO of CollegeReady, a 2026 Global Educational Consultant of the Year, a two-time bestselling author, and host of the podcast Parents, Is Your Teen College Ready?
Newest Episodes:
Pocket-Sized Advice: The Insurance Lesson Hiding in Half Marathon Training
September is Life Insurance Awareness Month and Emma Schneider is using her own half marathon training to make the case for why it matters.
You don’t train for 13.1 miles because you expect the worst mile of your life, you train so you’re ready no matter what race day brings. Life insurance works the same way: it’s not flashy, and you hope you never need it, but it’s what makes everything else possible for the people who depend on you.
Pocket-Sized Advice: Holiday Budget Tips: Set Your Number Before the Sales Start
Want to avoid holiday debt this year? The best time to build your holiday budget isn’t December, it’s right now. In this episode of Pocket-Sized Advice, TradeWinds President Stephanie Williams shares one simple holiday budgeting tip: look back at what you spent last summer, then set a real number for the holidays before the sales even start. A little planning now means a lot less financial stress in December.
Housing, career, savings, and how you talk about money with the people you love, none of these show up on a balance sheet or a portfolio statement, but they may matter more to your financial life than anything that does.
In this episode, TradeWinds advisors Jeb Bowie and Miller Hoffman break down four fundamentals that are easy to get wrong even though they’re not “basic”.
Inside TradeWinds
A Successful Trip to Dress for Success
A few members of our TradeWinds team — Mike Manganillo, Jeb Bowie, CFP®, Austin Moore, CFP®, and Grayson Tanner, FPQP® spent the morning volunteering at Dress for Success Triangle NC, helping get clothing ready for their upcoming Fall Boutique Sale.
Dress for Success does incredible work helping local women advance their careers and build financial stability, and it was a privilege to spend time supporting their mission alongside Laurin Norwood and the rest of the DFS team.
Teeing it up for Life Experiences
TradeWinds was proud to sponsor the Harry H. Montgomery Golf Tournament for the 3rd year running, benefiting Life Experiences, Inc. and their mission to support adults with intellectual and developmental disabilities.
Getting to spend the day on the course at Prestonwood Country Club with friends and clients, all in support of such a meaningful cause, is one of our favorite days of the year. Watching this event grow and seeing the community show up year after year is a great reminder of why we do what we do.
Sponsoring the Marbles Imagination Ball
We’re proud to support Marbles Kids Museum year after year, and this year’s “Dive Deeper” theme brought out our team’s best under-the-sea looks — trident and all. Every dollar raised helps ensure that every child in our community has the chance to imagine, discover, learn and play at Marbles, no matter their family’s circumstances.
TradeWindse Recommends
Tim
No one at TradeWinds gets more into the Halloween spirit than Tim. He transforms his home and office into a haunted showcase each October, and he’s never met a decoration too spooky.
Austin
For Austin, Halloween isn’t official until he’s rewatched The Office Season 2’s “Halloween” episode. It’s a quick, laugh-out-loud way to get into the spirit of the holiday.
Stephanie
Stephanie’s favorite Halloween tradition is walking Historic Oakwood to see the neighborhood’s legendary decked-out houses. Raleigh’s own front-yard haunted attractions never disappoint.
Mike
Mike’s Halloween tradition is a rewatch of Hocus Pocus. It’s the one movie that officially kicks off the season for him every year.
Question of the Month
“If my 401(k) and life insurance already have beneficiaries listed, do I still need a will?”
Yes, beneficiary designations and a will do different jobs. Accounts with a named beneficiary (retirement accounts, life insurance, many bank and brokerage accounts) pass directly to that person, regardless of what your will says, which is exactly why it’s worth double-checking those forms every few years. But a will still covers everything else — property, personal belongings, anything without a named beneficiary and it’s the only place you can name a guardian for minor children. Think of beneficiary designations and a will as two different tools doing two different jobs, not one replacing the other. Your estate attorney can help make sure the two are actually working together instead of pulling in different directions.
What’s Next?
October: Financial Horror Stories
Coming up in October: a look at some of the scariest financial horror stories out there, from identity theft to investment fraud. We’ll break down the warning signs and simple security habits that can help you avoid becoming the next cautionary tale.
Onward with Optimism,
The TradeWinds Team
