A Mid-Year Money Date: Reflect, Reset, Recommit

Ever feel like the year is flying by and you're not quite sure where your money is going — or whether you're on track? Same here.

That’s why now is the perfect time to set a money date with yourself (or with your partner) to pause, reflect, and reset. I’ll be doing this over the next couple of weeks — not to be perfect, but to be intentional.

We love the idea of calling it a money date because it makes this process feel lighter, even a little fun. You can dress it up or down: order takeout, sit outside with your favorite drink, or go for a walk and talk it through. The point is: make space for it.

Why Set a Money Date?

Think of it like a check-in with your future self. It’s not about fixing everything overnight. It’s about asking, “What matters most right now, and how can I support that with my money?” When we track and give something attention, it tends to improve — and your financial life is no exception.

Here Are Some Conversation Starters for Your Money Date:

Use these prompts to spark reflection and action. You don’t have to cover everything — just pick 2–3 that feel meaningful right now.

1. “How are my financial goals feeling right now?”

Maybe you’ve crushed a few (yay!). Or maybe something you were aiming for no longer fits. This is your chance to:

• Reconnect with your goals

• Update or delete any that feel outdated

• Set a fresh goal for the next 90 days

If you can’t tell whether you're making progress, your goals might not be specific enough — try rewriting them using clear numbers and dates.

2. “What’s going on with my spending — and does it still align with what I care about?”

Open your bank or credit card app and take a scroll. What categories are taking up the most space?

• Are those aligned with your values?

• Is there anything that surprised you?

• What spending brought you joy? What didn’t?

No shame here — just awareness.

3. “Do I feel good about how I'm using my income?”

Let’s take it further:

• Have your savings or debt payoff plans stalled?

• Are you putting extra income or bonuses toward your priorities?

• Could you increase a contribution by even $25 a month?

You don’t have to change everything — just look for small tweaks that help your money feel more intentional.

4. “Have I done a financial cleanup lately?”

This one’s about tidying up the little things that add up:

• Are you still using all your subscriptions or memberships?

• Did you check your free credit report this year?

• Do your financial accounts have up-to-date beneficiaries?

Grab your favorite drink and take 10 minutes to knock one of these off. Quick wins feel good.

5. “Is my savings system working for me?”

Check in on:

• Your emergency fund: Have you dipped into it? Is it fully funded?

• Short-term goals: Travel, gifts, holidays, house projects?

• Are your automatic transfers happening? Should you adjust amounts?

You might realize you’re closer to a savings goal than you thought. That’s worth celebrating.

6. “What financial win can I celebrate?”

We often rush past progress without pausing to recognize it. Ask yourself:

• What did I do with money in the last 6 months that I’m proud of?

• Did I say no to something I didn’t truly want?

• Did I start a habit, automate a bill, or stick to a boundary?

Write it down. Toast to it. Tell your partner or a friend. These moments matter.

7. “Am I moving forward in my career or income goals?”

Your income is a powerful financial lever. Consider:

• Are you tracking your professional wins? Use our free Brag List to track them!

• Is it time to ask for a raise or pursue something new?

• Could a small side hustle bring in some breathing room?

Sometimes the best money moves are outside the budget.

8. “When’s our next money date?”

Don’t wait another 6 months. Before you wrap up, look at your calendar:

• Choose a date for your next check-in — even if it’s just 30 minutes.

• Decide how you’ll make it enjoyable again (coffee shop, cozy PJs, celebratory glass of wine, etc.)

• Write down 1–2 action steps from this money date to review at the next one

Don’t Forget Your Free Resource

If you’d like a simple checklist to walk you through all of these areas, grab our free Mid-Year Money Check-In Checklist! It’s the perfect companion to your money date and includes space for notes and priorities.

Your Money Date Toolkit

Here’s what to bring to your check-in:

• 📄 Free Mid-Year Money Checklist

• 🖊️ Pen + notebook (or open your Notes app)

• ☕ A fun drink or snack

• 📅 Your calendar to schedule the next date

• 💛 A recent money win to celebrate

Final Thoughts

You don’t need to have all the answers or do it all at once. The magic is in showing up, checking in, and choosing one thing to move forward with. That’s how change happens — one intentional step at a time.

This is your invitation to pause, reset, and honor the effort you’ve already made. Your money date is just the beginning.