As August rolls around and suddenly there are backpacks by the door, supply lists on the fridge, and a new school year humming to life. It turns out August is one of the best-kept secret reset points on the calendar, right up there with January, minus the resolutions.
This month we’re borrowing that back-to-school energy for money: revisiting the lessons we wish someone had taught us sooner, figuring out how to pass a few of them on, and using the “first day” feeling to restart whatever financial habit or conversation has been sitting on the shelf all summer.
August: Back to School Money Lessons
Teaching the Next Generation (Without the Lecture)
Kids don’t need a finance degree explained to them at the dinner table — they need small, repeatable habits modeled early. A few ways families we work with are building that in:
- A simple three-jar system: save, spend, give teaches the framework long before algebra does
- Letting a teenager make a real budgeting mistake with $20 of their own money teaches more than a lecture ever will
- 529 plans and custodial accounts still do the heavy lifting for education costs, Trump Accounts, which we covered last month, are a new addition to the toolkit, not a replacement for them
- Matching a portion of what a teenager saves from a summer job previews the idea of a 401(k) match years before they’ll actually get one
- Talking about money at home, even imperfectly, normalizes the topic before adulthood is forced to teach it the hard way
Back-to-School Money Moves (For the Grown-Ups, Too)
The new-school-year reset isn’t just for households with kids. A few moves worth making while the “fresh start” feeling is still in the air:
- Revisit 529 or custodial account contributions before year-end planning season sneaks up
- Check FSA and dependent-care account balances, “use it or lose it” deadlines arrive faster than expected
- Reset the household budget for the new school-year rhythm: activities, supplies, tuition, before- and after-care
- If a student loan is back in the picture , yours or a new graduate’s, confirm the servicer and repayment plan before payments resume
- Take advantage of a state sales-tax holiday if one applies where you live
“The best financial lessons rarely arrive as a lecture. They arrive as a habit, repeated often enough that it stops feeling like a lesson at all.”
From the Studio
Newest Episodes:
Episode 14: Back to School Money Talk: A Teen’s Take on Budgeting, Saving & AI with Jack Adkins
This month’s theme is back to school, so we flipped the script and put a high schooler in the guest chair. Jack Adkins just wrapped up his summer internship at TradeWinds, and before that, he was figuring out money the same way most students do: mostly on his own.
Newest Episodes:
Pocket-Sized Advice: Pocket-Sized Advice: What Basketball Taught Me About Staying Invested
In this episode of Pocket-Sized Advice, Ralston breaks down why market volatility doesn’t mean something’s wrong, and shares one simple question to ask before making any change to your investment plan: Did my goals change, or am I reacting to how I feel right now?
Pocket-Sized Advice: What Financial Independence Actually Means (It’s Not What You Think)
In this episode of Pocket-Sized Advice, Jeb breaks down financial independence as a threshold, not a finish line: the point where your money covers your life so every decision becomes a choice instead of a necessity. You can keep working, switch careers, or take a year off. The point is that you get to decide, not your bank account.
Inside TradeWinds
New TradeWinds SWAG
New TradeWinds swag has landed and yes, SWAG really does stand for “Stuff We All Get.”
From the water bottles to the tote bags to the golf balls, we can’t wait to start handing these out to our team and sharing them with clients too. We are especially excited about our custom coffee with 321 Coffee | Specialty Coffee Roasters, a Raleigh roaster that employs adults with disabilities, because representation matters well beyond the packaging.
Supporting the Wild Bill 5K
Four years running TradeWinds is proud to be a Gold sponsor of the Wild Bill 5K again this year, honoring Raleigh legend William “Wild Bill” Sonner, who ran daily rain or shine for nearly 70 years.
This year’s heat gave that legacy a real test, and our own Tim Whitney barely made it to the finish line to prove it. Beyond the medals, the race funds The Helene Foundation and new scholarships for local high schoolers who show Wild Bill’s same grit.
TradeWinds Travels
This summer had the team scattered across three very different corners of the map. Stephanie and her family explored Scotland and came home fully smitten with the Highland cows. Mike traded the office for the California coast, road-tripping from the Bay down to the beach. And Ralston’s crew went full magic with a trip to Disney World, we’re told at least one Mickey ear photo is mandatory viewing.
TradeWindse Recommends
Ralston
Ralston is back coaching basketball at Broughton High School this fall. Between advising clients and running practice, we’re not sure where he finds the hours.
Tracey
Ask Tracey and she’ll tell you: fall is the whole point of the calendar. The second there’s a chill in the air, she’s got a firepit going, marshmallows on standby, and zero interest in coming back inside.
Grayson
JFall means one thing in Grayson’s world: draft season. She’s been building her roster since June, keeps a spreadsheet that rivals anything in our client portal, and treats waiver-wire Tuesdays like a second job.
Miller
Miller’s spending this fall on a mission, dialing in the perfect brisket on his Traeger. Low, slow, and (his words, probably) scientific
Question of the Month
“It seems like a college degree is losing its value when the rise of technology/AI. Is college ‘worth it’ anymore?
Education, and the pursuit therefore, it a pretty personal decision. It’s no secret that some degree paths lead to higher incomes; this is also largely true based on level of education. A Bureau of Labor Statistics (BLS) study in 2025 found that the median salary for those with a high-school diploma was about $50,000/year. Compare this to an individual with a Bachelor’s degree who comes in around $82,000/year. Getting a college degree is not a strict requirement for success; the research does suggest education is still a great ‘bet’ on your future income potential.
What’s Next?
September: Protect What You Built
September pivots from back-to-school into protection: it’s Life Insurance Awareness Month and National Preparedness Month, and it’s the natural moment after a summer of spending, when people start thinking about safeguarding what they’ve built before Q4 planning ramps up
Onward with Optimism,
The TradeWinds Team
