On October 8, 2025, we decided to go on a family vacation I was decidedly unexcited about. That entire week was supposed to be my time to attend the Fairfield Challenger tennis tournament every day with my buddy Richard. September and October are tennis paradise months in the Bay Area, with multiple tournaments and ideal […]
Vacations Just Aren’t As Great Anymore Once You Retire Early Read More »
Picture this: no alarm clock jolting you awake at 6 a.m., no endless meetings that could’ve been emails, and no scrambling to stretch your paycheck to cover bills. Instead, your money is working for you—even while you’re sipping coffee on your porch or traveling somewhere sunny. That’s the dream of financial independence. For many, retiring
The Financial Independence Playbook: Using Passive Income to Retire Early Read More »
Before I retired from finance in 2012, I struggled with chronic back pain, sciatica, and TMJ. The stress was so overwhelming, I even paid a dentist $700 to drill divots into several teeth just so I could close my jaw more easily. At only 34, my body was breaking down, and I had no choice
Health Issues Or A Disability May Force You To Retire Early: Prepare Accordingly Read More »
If we’re not already in a recession, we may soon enter one due to aggressive trade policies that are fueling tremendous uncertainty. As companies and consumers pull back on spending, millions of jobs could be lost, trillions in stock market wealth may disappear, and inflation could persist—potentially ushering in a stagflationary environment. If you’ve been
What A Recession Is Like For Early Retirees: The Good And Bad Read More »
Despite the wonderful peace of mind that comes with owning a home free and clear, deciding to pay off a low-interest rate mortgage early is not always straightforward. If your mortgage rate is low compared to risk-free investment returns, keeping the mortgage and investing excess cash elsewhere often makes more financial sense. What Is Considered
The Only Good Reasons To Pay Off A Low-Interest-Rate Mortgage Early Read More »
One of the biggest reasons I was against contributing to a Roth IRA is my belief that most people won’t make more money in retirement than while working. As a result, they’re unlikely to pay a higher tax rate in retirement than during their working years. This belief also assumes that tax rates will stay
Why You Could Make More In Retirement Than While Working Read More »
Happy New Year everyone! I hope you’re enjoying the time off and doing some reflecting. I’ve returned to San Francisco and am ready to relax some more! Now that I’ve shared my 2024 year in review, I wanted to share my goals and resolutions for 2025. Although 2024 was a great year, I still have
2025 Goals And Resolutions: Back To A Simple Retirement Life Read More »
When saving for retirement, understanding the various account types and their funding priorities is crucial for maximizing your savings and minimizing taxes. Below, I break down the key account types and outline a suggested order of funding for optimal retirement planning. The ideal order to fund retirement accounts focuses on minimizing tax liability, reducing the
The Best Order To Fund Retirement Accounts And Minimize Taxes Read More »
There’s a lot of enthusiasm for Roth IRA conversions and Mega Backdoor Roth IRAs—and for good reason. Paying taxes upfront on your retirement accounts can be a savvy move, especially if you’re in a mid-to-lower federal income tax bracket, as it allows for tax-free withdrawals in the future. That said, thanks to the latest standard
Maximizing Tax-Free Income and Withdrawals In Retirement Read More »
Ever since I started saving for retirement in 1999, I’ve been a proponent of tax-deferred retirement vehicles like the 401(k) and skeptical of tax-now vehicles like the Roth IRA. Working in banking, I was already being taxed out the wazoo and had no desire to pay even more. Frankly, I wasn’t even familiar with the
Mega Backdoor Roth IRA: Supercharging Your Retirement Savings Read More »
