Most retirees who make this mistake aren’t reckless. They’re careful. They’re doing what they believe is responsible, and that’s what makes it so painful to see when it backfires.James explains why...
A $10 million retirement is often imagined as the finish line — complete freedom, unlimited spending, and no financial stress. The reality is more complex.James walks through what an eight-figure r...
Retiring after age 65 changes the math and the priorities. You have fewer high-energy years, shorter tax planning windows, and RMDs much closer than most people realize. But you also often have hig...
Christian thought he was ready for retirement. He just didn’t realize how heavy the weight had been until he finally set it down.After more than 30 years in a high-stress, always-on role at a globa...
Some of the most damaging financial advice doesn’t look shady at all. It looks responsible. It looks optimized. And it looks great on a spreadsheet. This episode breaks down one of the most unethic...
Retirement doesn’t always arrive on your schedule. Sometimes it shows up early, uninvited, and forces you to rethink everything you thought you knew.For Jim, that moment came at 5, four years befor...
Roth conversions can save thousands in taxes, but they can also trigger Medicare IRMAA surcharges that quietly add up to more than $5,000 a year. Most retirees never see it coming, because the rule...
Steve spent more than two decades building video games, working with a team that felt more like family than coworkers. By all measures, he loved his work. But a heart attack in 2021 changed everyth...
Most retirement advice quietly assumes you have a partner: two incomes, two Social Security checks, someone to split expenses with, someone to catch the slack if something goes wrong. But for singl...
Retiring at 50 sounds bold, almost unthinkable for most people, but for Kent, it was the only decision that made sense once life, loss, and perspective pushed everything into focus. In this convers...
Think waiting until 70 is the gold standard for Social Security? We dig into the real math behind delayed retirement credits and the hidden trade-offs that rarely make it into the headlines. Drawin...
Retiring with a pension changes everything about your retirement math.Most people think about retirement in terms of net worth—how close they are to a million, two million, or more. But if you have...
Some retirees have more money than they ever imagined… and still feel guilty buying the $5 M&Ms.This episode is for the lifelong savers who nailed the retirement planning side—maxed out account...
A cancer diagnosis changed everything. When Michael’s wife began chemo, time took on a new meaning. The long-term financial plan suddenly felt secondary to the years they still had together. That w...
Forget the race for the biggest Social Security check. The real question isn’t how high your benefit can go, it’s how well it fits your life, taxes, and long-term plan.In this episode, James breaks...
In this episode of Retirement Reality, Darren shares what it’s really like to walk away from work at 54 and why it still feels surreal. After decades of saving, hitting his number, and paying off t...
A single misunderstanding about Social Security spousal benefits can cost couples thousands over retirement. This episode unpacks the real math behind how Social Security treats spouses, ex-spouses...
What if the “smart” money choice isn’t the choice that builds your best life?This Root Talks episode starts with a bucket-list moment for James—throwing the first pitch at a Padres game—and turns i...
Those “3x by 40, 6x by 50, 10x by 67” charts feel official—until your life doesn’t match the average. In this episode, James shows why age-based savings benchmarks miss the mark and replaces them w...
In this episode of Retirement Reality, meet Donovan, a 55-year-old retiree who turned an unexpected career exit into an opportunity for freedom, reflection, and new purpose. Donovan shares how one ...
