The Black Oak Podcast
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How to Spend on Travel Without Derailing Your Retirement
Summer's here. And somewhere between the excitement of planning a big trip and the anxiety of what it costs, a lot of retirees end up doing something that surprises us… they feel guilty about it. They worked hard, saved, planned...
More Episodes
Should You Sacrifice Pension Income for Spousal Protection?
When retirement is around the corner, some of the biggest decisions aren’t about when to retire, they’re about how income continues if one spouse is gone. Ryan walks through a listener question about pension survivor options and why these decisions...
Three Questions From People Thinking About Retiring In 2026
Ryan’s doing something a little different today. Three listeners wrote in with variations of the same question, “Am I ready to retire in 2026?” Same question, three very different situations, three very different answers. If retiring in 2026 is on...
“I Wish I Knew This at 25” — Young Adult Money Mistakes
Spend five minutes on Reddit or YouTube and you’ll find people being brutally honest about what they wish they had done differently with money. Today, Ryan’s pulling from some of those real conversations and breaking down the lessons behind them....
The Financial Side of Taking Care of the People You Love
Financial planning isn’t really about spreadsheets, rates of return, or chasing the perfect investment strategy. At its core, it’s about making sure the people you love are protected if life takes an unexpected turn. Ryan discusses the often-overlooked side of...
You've Managed Your Own Money Successfully - Why Would You Need an Advisor Now?
You’ve done a great job managing your money over the years, but retirement changes the game. Ryan looks at the deci-sion many investors face: should you keep doing it yourself, or bring in a financial advisor? He walks through what...
My Investments Underperformed the Market - Should I Fire My Advisor?
It’s a question a lot of people ask at some point: if your investments aren’t keeping up with “the market,” is it time to move on? Ryan breaks down what you’re actually comparing against, why that comparison can be misleading,...
A New Proposal Might Cap Your Social Security Payments
A new proposal out of Washington is adding a fresh angle to the Social Security conversation, and Ryan is breaking down what it could mean. He walks through what’s being discussed, who it might impact, and how it fits into...
Why Spending in Retirement Is Harder Than It Sounds
Most retirement conversations are about saving enough, but Ryan flips the script and talks about what happens after you get there. Why is it so hard to actually spend the money you worked decades to build? This episode dives into...
Long-Term Care Insurance: Worth It or Waste of Money?
Long-term care is one of the biggest financial risks in retirement, and one of the most uncomfortable topics to talk about. Most people know it’s important, but few have a clear plan for how they’ll actually handle the cost if...
Put Off Social Security Or Start It Earlier?
When should you take Social Security? It’s one of the biggest financial decisions you’ll make in retirement, and one of the easiest to get wrong. It’s not about finding “the best” age, it’s about making an educated decision based on...
Tax Mistakes New Retirees Make
Nobody likes tax season, but for new retirees, the rules can feel completely different. Income changes, required withdraw-als begin, and decisions that once lowered taxes can create bigger bills later. Ryan unpacks some of the most common re-tirement tax mistakes...
And the Oscar Goes To... Your Retirement Strategy
The Oscars have passed, but we’re handing out a few awards of our own. Not for films, but for financial planning. Be-cause when you think about it, a great retirement plan has a lot in common with a great movie:...
Use Target-Date Funds or Customize Your Portfolio?
Target-date funds are one of the most common investments inside retirement plans, largely because they’re simple and automatic. But are they really the best option for your long-term portfolio? In this episode, Ryan explains how these funds work, why they’ve...
