A Financial Planner’s Weird Birthday Tradition (That Might Just Be Genius)

Financial planning isn’t about spreadsheets—it’s about structure, choices, and a little creativity.

Every May, when most people are planning BBQs and buying sunscreen, I sit down for a little celebration of my own: logging into SSA.gov.

Yes, my birthday tradition involves downloading my Social Security statement and pretending I’ll cross-reference it with my W-2s (spoiler: I won’t). But if I’ve managed to remember my login credentials and survive their two-factor authentication system? I consider that a birthday miracle.

Some people treat themselves to spa days or shopping sprees. I check government websites, update my financial dashboards, and renew my vow to finally—finally—update our estate plan. Shoemaker’s children and all that...

But this year, I decided to take it one step further and formalize my weirdly satisfying habit into a Birthday Financial Checklist. Because while it’s not festive, it is freeing—and it feels great to hit my birthday knowing our financial house is at least mostly in order.

The Birthday Financial Checklist

✅ Check Social Security Statement (SSA.gov: because I'm the life of the party)

If you’d like to learn how to calculate what your future Social Security benefits are actually worth, you can download our free guide that walks you through how SS benefits are calculated and how you can use a simple Excel formula to see what your benefits are worth.

✅ Confirm taxes were filed and collect deductible expenses like child care and vehicle registration
✅ Check credit reports (at AnnualCreditReport.com)
✅ Run a spending review in Monarch Money – I do 15–45 minutes each week to stay on track (Click HERE for 50% off your first year)
✅ Review subscriptions and recurring charges – Summer’s a great time to say goodbye to the apps and services that just aren’t earning their keep
✅ Make birthday resolutions – This year: finally update our estate plan, which I started back when COVID and our Nevada move were still fresh
✅ Family finance pulse check – Talk with the kids about money goals, screen time trades, and what I will and won’t buy next school year

Summer Spending & The Screen-Time Economy

A May birthday also means one thing: school’s out, wallets out. I just paid what feels like a small mortgage for summer camps to keep their bodies busy. But idle brains? That’s where my favorite family tradition kicks in:

Welcome to the Bray Family Screen Time Economy—where reading, Kumon, and workbook pages earn screen time, and screen time can be converted to cold, hard cash. (Don’t worry, it’s budgeted.)

This summer, I’ve given them a chance to earn big:

• Billy’s tutoring dream is finally happening. He wants to make real money and I think he's ready—for the right family and the right kid in our neighborhood.

• I've laid out exactly what I’ll buy for fall, winter, and spring. If they want more, they have to budget, save, and pay for it.

• We're using Greenlight to track their earnings, set spending limits, and—crucially—make sure I get paid back for those golf shoes. (Charlotte offered to split hers after realizing the cheaper ones were out of stock in her size. Savvy is catching on.)

💸 Want to start your own screen-time economy?
Sign up for Greenlight and earn $30.
It’s a debit card and money app for kids and teens that lets you instantly send money, assign chores, set savings goals, and even introduce investing. (Also: it's way more fun than nagging.)

Mid-Year Family Financial Moves to Steal

Whether your birthday's in May or not, mid-year is a great time to check in on your household money. Here's what else I recommend:

1. Check your tax withholding

Make sure you’re not setting yourself up for a surprise in April. Use the IRS estimator.

2. Revisit your budget and cash flow

If you set a 2025 budget, does it still reflect reality? (Looking at you, rising grocery and summer camp costs.)

3. Update your emergency fund

Have you tapped it this year? Adjusted for any lifestyle changes?

4. Review insurance coverage

This includes umbrella policies—especially if you now have teen drivers, pools, or businesses.

5. Max out (or catch up)

Check your pace for 401(k)s, IRAs, 529s, and any other contribution-based goals.

6. Review your subscriptions

I love this one: cancel the zombie apps that auto-renewed when you blinked.

7. Talk about money as a family

This summer, build habits—not just memories. Talk about earning, saving, investing, and yes, spending. Little things like paying you back for golf shoes are big lessons in the long run.

So yes, I check my SSA.gov account on my birthday. But I also check in on my family’s future.

Because financial planning isn’t about spreadsheets—it’s about structure, choices, and a little creativity… especially when you’ve got three kids and an iPad habit to manage.

Now if you’ll excuse me, I have to categorize a few expenses before cake.

The content is developed from sources believed to be providing accurate information. The information in this material is not intended as tax or legal advice. It may not be used for the purpose of avoiding any federal tax penalties. Please consult legal or tax professionals for specific information regarding your individual situation. This material was developed and produced by GW Financial, Inc. to provide information on a topic that may be of interest. The opinions expressed and material provided are for general information, and should not be considered a solicitation for the purchase or sale of any security. Copyright 2025 GW Financial, Inc.