The Four Seasons of Planning
Winter Season: Retirement & Cash Flow
Why This Season Matters
Winter is the perfect time to get your financial house in order. The new year is here — a new financial you. I put this guide together because I want to motivate you to take action. A conversation covering your cash flow, your retirement income strategy, and your next chapter sets the tone for everything that follows. The more prepared you are walking in, the more we can accomplish.
What You'll Walk Away With
- ✓A clear picture of your monthly cash flow — what's coming in, what's going out, and where you can optimize.
- ✓Confidence in your retirement income strategy, including when and how to claim Social Security.
- ✓An understanding of how to protect your future income from market volatility and sequence-of-returns risk.
- ✓A personalized action plan — specific next steps tailored to your situation after our meeting.
💰 Cash Flow Topics
- Discuss budgeting with Monarch Money
- Search for missing money at your state's unclaimed funds website
- Build your financial plan with Right Capital
- Discuss account funding or distribution needs
- Review your cash management strategy
- Review our Prioritizing Cash Flow guide
- Review Flourish Cash and the client portal
- Get organized with insurance and asset spreadsheets
📈 Retirement Topics
- Review your Social Security statement and claiming strategy
- Discuss the 8 Levers of Retirement piece
- Discuss the 5-Year Protection Shield
- Understand safe withdrawal rates
- Understand sequence-of-returns risk
- Discuss your retirement picture
- Review your RMDs strategy
- Discuss your legacy and inheritance goals
The Big Idea This Season
There are actually two ways a retirement can fail. The first is running out of money. The second — and just as real — is leaving this world with $3 million you never touched because you were too afraid to spend it. Both are failures. My goal this season is to help you run the numbers and make the best, most confident choices for your retirement income needs.
Questions to Think About Before We Meet
Do you know exactly where your money goes each month — and does it reflect what matters most to you?
Have you checked whether you have unclaimed funds sitting at your state's treasury?
Are you confident in when you'll claim Social Security — and do you know how that decision affects your lifetime income?
If the market dropped significantly the year you retired, would your plan still hold up?
Do you have a clear strategy for how you'll draw down your accounts in retirement — and in what order?
Is your cash sitting in an account earning a competitive rate, or is it working harder somewhere else?
How to Prepare
-
Social Security StatementYou can retrieve yours by creating a free account at www.ssa.gov
-
Mortgage InformationOriginal balance, current balance, interest rate, loan term, and your principal & interest payment.
-
Other Loan InformationStudent loan statements and outstanding credit card balances.
-
Monthly Average Spending FiguresAn approximate figure is totally fine — we just want a reasonable ballpark to work with.
📎 Send your documents securely before the meeting
Your files are encrypted and go directly to David.
Tools & Technology Powering This Season
Here are the tools we use to power your financial plan.
Right Capital
Your comprehensive financial planning platform — built around your goals.
Monarch Money
Smart budgeting and cash flow tracking to see exactly where your money goes.
Flourish Cash
High-yield cash management so your savings are always working harder for you.
Encyro
A secure encrypted platform to safely share sensitive documents.
Ready to Make the Most of This Season?
Let's sit down and work through these topics together. Whether you're focused on cash flow, retirement planning, or both — a simple conversation can make all the difference. Book your Winter Season meeting below.