Let’s challenge conventional wealth accumulation wisdom…
Our team recently read the book, Die With Zero: Getting All You Can From Your Money by Bill Perkins. It’s an easy-to-read personal finance book that challenges current retirement norms.
(We have extra copies—feel free to stop by and pick one up. We’d love to meet you!)
Today, we discuss how to:
- Get all you can from your money, (i.e., highlight ideas from the book Die With Zero).
- Spend confidently and without regret in retirement.
- Decide the right time to give—now or later—using sophisticated money modeling.
Get All You Can From Your Money
Bill Perkins’ “Die With Zero” overall argument is:
When preparing for retirement, people often save too much and spend too little, ultimately missing out on meaningful life experiences.
Perkins argues money should be spent strategically for fulfillment, not just left behind.
Before going any further, let’s be clear…
We’re not encouraging you to be financially irresponsible. Absolutely not!
But, Perkins is definitely onto something—especially when you combine his ideas with strategic financial planning.
Here are some of his key points:
Maximize Life Experiences: Instead of focusing solely on accumulating wealth for retirement or your heirs, think about how you can use your money to create meaningful experiences while you’re able to enjoy them.
Time-Bucket Your Life: Your life has different stages, and each one comes with unique opportunities. Be intentional about how you allocate your money so you can make the most of every phase—especially while you’re healthy.
Invest in Experiences Early: The best time to create lasting memories isn’t “someday”—it’s now. Enjoying experiences earlier in life helps you feel more fulfilled.
Avoid Over Saving: Too many people work longer than they need to and save more than they’ll ever spend. The result? They leave behind wealth they never got to enjoy themselves.
Optimize Giving: If you plan to leave money to loved ones or charities, consider giving earlier rather than waiting until after you’re gone. Your generosity could have a much bigger impact now.
[Related Blog Post]: One of the best times to use Qualified Charitable Distributions (QCDs) is early in the year. Learn why in our post, 2025 Tax Planning Resources & Key Financial Data Spreadsheet.
Plan for a Declining Health Curve: Your ability to travel, explore and be active won’t last forever. That’s why it’s important to strike a balance between financial security and truly living while you can.
Perkins’ ideas sound reasonable. In reality, though, most require detailed financial planning.
This is where we come in…
Spend Confidently and Without Regret in Retirement
Many retirees worry about spending their money, i.e., What if the market takes a downturn? What if I outlive my savings?
While these concerns are natural, a well-structured financial plan helps you be intentional with your spending and feel secure knowing your money will outlive you.
Our role is to guide you through this process with a clear four-step approach:
Step #1—Determine Your Retirement Spending Capacity & Create a Tax-Efficient Withdrawal Plan
Everyone’s financial situation is unique, with different levels of savings, income sources and comfort with risk. We take a personalized approach to managing your investments—balancing growth with stability while ensuring you can spend confidently in retirement.
A key part of this strategy is minimizing taxes on your withdrawals so you keep more of what you’ve saved. We do this by carefully selecting which accounts to withdraw from first—whether taxable, tax-deferred or tax-free—based on your income needs and current tax rates.
This approach helps extend the life of your portfolio, allowing your investments to continue growing even as you draw from them.
Overall, it’s our job to tell you how much you can afford to spend in retirement. A primary tool we use to help you is advanced software (aka Income Lab) that includes sophisticated money modeling guardrails.
Resource: We discussed money modeling guardrails in a recent post: 3 Steps To Help Your Money Outlive—You.
Step #2—Create a Monthly Paycheck for You
One of the biggest adjustments in retirement is transitioning from a regular paycheck to drawing from multiple income sources.
Most of our clients rely on a mix of Social Security, pensions, part-time work and investment withdrawals for their retirement income.
Some also have additional income streams, e.g., rental properties, royalties, payments from seller financing, etc.
Understanding how these income sources interact is essential for confident retirement spending.
That’s why we focus on transforming your various income streams into a tax-efficient monthly paycheck.
Simple Example:
Imagine your annual withdrawal plan from investments is $84,000 (excluding Social Security, pensions and other income sources). Each month on the 15th, we’ll deposit $7,000 from your investment portfolio into your checking account, ensuring you receive a steady stream of income.
This way, you can enjoy a sense of stability, knowing a $7,000 “paycheck” will arrive in your account every month.
Step #3—Put Aside Two-to-Four Years of Safety Net
To help ensure you can weather market fluctuations without disrupting your lifestyle, we set aside two-to-four years’ worth of income needs in a conservative investment account (that still grows).
For example, if you plan to spend $84,000 per year, we earmark $252,000 to cover the first three years of retirement.
This portion of your portfolio is stable, meaning that even if the market declines, your ability to meet your spending needs remain intact. Meanwhile, the rest of your investments continue growing for the future.
Step #4—Perform Annual Audits & Make Smart Adjustments
Each year, we reassess your portfolio balance versus your spending and market conditions.
If the market performed well, we “refill” the amount spent from the safety net.
However, if the market had a down year, we hold off on refilling and use the second year’s reserve instead.
Since market recoveries typically take six to 18 months, this approach helps protect your long-term investments.
Audit: Keeping Spending on Track
As part of the audit, we discuss your spending target. Again, let’s say it’s $84,000. If you end up spending more, perhaps $98,000, it may not be an issue if the market was strong. However, if higher spending becomes a pattern, we’ll flag it and have a conversation about sustainability.
Retirement should be about enjoying life, not worrying about money.
By following a plan that balances stability with flexibility, you can confidently spend with the knowledge that your financial future is secure.
Decide the Right Time to Give—Now or Later
Imagine sharing your wealth with loved ones now—without stressing about your future finances.
How does Windsor Wealth Management help you decide whether to give money now (especially if your loved ones could really use it), or wait?
We typically present two scenarios:
Scenario One: You hold onto your money and pass it on after you’re gone.
Scenario Two: You gift, say, $5,000 to each grandchild now and see the impact on your financial plan.
Most of the time, the effect from early giving is minimal.
Using our real-time software modeling, we run the numbers so you can see the difference.
For example, perhaps instead of spending $12,000 per month, you adjust to $11,500.
This way, you can give—now—with confidence.
Final Thoughts
Bill Perkins offers some good insights, encouraging people to make the most of their wealth during their lifetime.
Keep in mind, his perspective comes from the lens of a successful (and wealthy) hedge fund manager and entrepreneur.
Ultimately, as with all things in life, balance is key—enjoying your wealth while ensuring financial security for the long run.
–David Bunker, Financial Advisor & Licensed Fiduciary
Before You Go
Get help optimizing your retirement income. Download our FREE “Prolonging Retirement Income” checklist.
Also, receive help retiring to the life you want, schedule a complimentary financial planning consultation.
This communication was prepared with financial writer Sharron Senter’s assistance, based on interviews with David Bunker, a financial advisor and licensed fiduciary.