Ready For Retirement

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 unethical practices James sees in financial planning, not selling high-fee products, but using projections and tax strategies to justify an advisor’s fee while ignoring the life those numbers are supposed to support. 

The problem starts...

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 before the retirement date he’d carefully planned for. One unexpected layoff, and suddenly the identity he’d built over decades in big tech was shaking underneath him.

In this episode of Retirement Reality, James shares the ...

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 rules for Medicare premiums don’t line up with the tax brackets everyone focuses on.

In this video, James breaks down how Roth conversions interact with Medicare Part B and Part D premiums, why modified adjusted gross income matters ...

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 everything, and it became the moment that pushed him to rethink the one thing he’d always said he wanted someday: an early retirement.

In this episode, Steve sits down with James Conole, CFP®, to share how a health scare, a divorce, and...

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 singles, the margins are tighter and the freedom can be much greater. Planning alone means every decision carries more weight, but it also means you have full control over the life you want to build.

This video centers on Tina, a 62-y...

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 conversation, he sits down with James Conole, CFP®, to share the honest story behind leaving work two decades earlier than expected.

Kent talks about saving from age 18, building a plan long before he knew what retirement would look lik...

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. Drawing on years of planning experience and two vivid case studies, we show how the “bigger check later” can either amplify your lifetime income or quietly drain the resources you need to feel secure.

We start with the promise of delay...

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 a pension, that old framework can send you down the wrong path. In this episode, James explains why retirees with pensions need to think in terms of cash flow, not balances on a statement.

James begins with a simple shift: ...

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 accounts, invested consistently, hit their “number”—but feel stuck when it’s time to actually spend. James and Ari share real client stories of multimillionaires who still walk past convenience to save a few dollars, not because they need to… bu...

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 wake-up call led Michael, then 57, to retire a full decade earlier than planned, trading more income for more life.

In this conversation with James, Michael shares the mindset shift that made him walk away from a thriving career a...

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 down how the timing of your claim shapes everything: portfolio resilience, tax efficiency, survivor benefits, and the freedom to retire when you want, not when the system says you should.

Starting with the foundation (your 35 highest earn...

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 the house, a company reorg gave him the push he needed to finally make the leap.

He talks about how it feels to go from structure to freedom overnight, what surprised him about early retirement, and why he refuses to see it as a “...

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, and survivors, so you can make smart claiming decisions that protect both cash flow and long-term security.

Listen to learn how the spousal benefit actually works: it’s based on 50% of the primary earner’s full retirement age benefit, no...

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 into a bigger lesson: money is a tool to create meaning, not a score to keep. It’s a look at the Five Types of Wealth (financial, time, social, mental, and physical) and why the spreadsheet answer isn’t always the human answer.

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 with a simple, four-step method that fits you.

First, get clear on spending in retirement (inflation-adjusted, lifestyle-aware). Then credit guaranteed income, like Social Security, pensions, annuities, part-time work, help to size the real...

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 defining word, choice, shaped his journey before, during, and after retirement.

From years of disciplined saving and intentional living to facing an unplanned exit from corporate life, Donovan opens up about how preparation, mind...

Early retirement income can feel complicated, but a steady paycheck from savings starts with a simple framework. This episode reframes withdrawal decisions, explains why a fixed 4 percent rule can be too conservative in some cases, and shows when a 5 percent starting point may fit with the right allocation and ongoing adjustments. A million dollar case study turns rates into an annual paycheck while addressing sequence risk and fle...

Retiring early isn’t just about having enough money, it’s about using the right tax moves in the right years. This conversation between James and Ari maps the three biggest levers for early retirees: Roth conversions, ACA health insurance subsidies, and 0% long-term capital gains. A real-world case study shows how account mix and spending levels can flip what’s “best,” and how small income shifts can change the math in a big way.

Th...

What if the next 10 years bring just 3% returns from the S&P 500?
In this episode, we turn that forecast into a real-world retirement plan—not panic. You’ll learn how to stress test your portfolio, build flexibility into your spending, and design a withdrawal strategy that can survive tough markets.

Listen as James and Ari break down:
Sequence-of-returns risk — why bad early years hurt more than bad averages.
The mod...