Do I Really Have Enough? Turning Retirement Anxiety Into a Clear Plan
Episode 072
Aired on January 24, 2026
“When people understand what they can spend and why, their confidence in retirement changes completely.”
Retirement is often painted as the finish line. The reward after decades of work. But for many people, retirement feels less like a victory lap and more like stepping onto unfamiliar ground. In this episode of Retire Well, Josh Bretl and Mark Elliott explore why confidence in retirement has declined and what it really takes to feel comfortable spending the money you worked so hard to save.
What Rock Climbing Teaches Us About Retirement
Josh opens the show with a story from a recent family outing to an indoor rock climbing gym. Watching his kids push themselves to try new routes and trust unfamiliar holds became a powerful reminder of what retirees experience when they leave the structure of work behind. Retirement, much like climbing, requires adaptability, confidence, and a willingness to move forward even when the next step feels uncertain.
Just as his daughter paused to think through a difficult move on the wall, retirees often pause when faced with questions like “Do I have enough?” or “How much can I safely spend?” The challenge is not just financial. It is emotional. Retirement represents a major life transition, and transitions can be uncomfortable without a clear plan.
Key Financial Changes Retirees Should Know for 2026
The conversation then shifts to several important updates that could impact retirement planning in 2026. These changes create opportunities, but only for those who understand how they fit into their overall strategy.
- Higher IRA and 401(k) contribution limits, including expanded catch up options for those nearing retirement
- Social Security cost of living increases and how Medicare premiums may offset them
- Major changes to Medicare Part D that are creating confusion for many retirees
- Temporary senior tax deductions and new charitable giving rules, including deductions even for those who do not itemize
Josh emphasizes that these changes should support your broader plan, not drive it. Chasing deductions or rule changes without context can create more problems than they solve. The goal is thoughtful planning that aligns with how you actually live.
Why Retirement Confidence Is So Hard to Find
A recent study found that only about 30 percent of retirees feel optimistic about their financial future. Josh explains why this number is not surprising. Retirement requires a complete mindset shift. After decades of saving, avoiding debt, and building independence, retirees are suddenly asked to spend their assets, rely on Social Security, and navigate Medicare.
The loss of pensions has only made this transition harder. Previous generations retired with predictable income streams. Today, many retirees rely heavily on their own savings, which makes market volatility and inflation feel far more personal.
“If I run out of money, I’ll live in my daughter’s basement. She knows the plan. Not everyone is quite that comfortable.”
The Role of Income Planning and Sequence of Returns Risk
One of the biggest threats to retirement confidence is sequence of returns risk. Josh explains how market losses early in retirement can have a much larger impact than losses later on, especially when withdrawals are happening at the same time.
This is why income planning matters. The focus is on building an income floor designed to cover essential expenses while allowing other assets time to grow. This approach can help retirees avoid pulling money from the market at the wrong time and feel more comfortable spending.
When retirees understand where their income is coming from and how long it is designed to last, optimism tends to increase. Planning replaces fear with clarity.
Ready to talk? Call (630) 478-9599 to schedule your complimentary 15-minute call with a Wellment advisor.
