This Indiana Jones–inspired episode of Retiring Today with Loren Merkle turns a common worry—how to start planning for retirement at 55—into a guided trek through six milestones: lifestyle, income, taxes, investments, health care, and legacy. We go on an adventure that blends adventure with practical guidance in search of the “compass of clarity.”
Finding Your Way Out of the Cave
Retirement planning can feel like stepping into a dim maze. As Retirement Planner Loren Merkle puts it, “So often families just don’t know–where do I even start and when’s the right time to get started in building out their plan.”
The map begins not with spreadsheets but with lifestyle—because the life you want drives every financial choice that follows. “So many families often get lost in the financial details. And they forget that retirement’s really all about lifestyle,” Loren says.
The first assignment is simple and revealing: sketch the day-to-day you’re aiming for—travel, grandkids, part-time pursuits, or a second home—and let those aims steer the plan.
Milestone One: Lifestyle
It may surprise people that the first step in retirement planning isn’t financial at all. Lifestyle comes first because everything else—income, taxes, investments—should support how you want to live.
“We have every family that we work with fill out a lifestyle survey,” Loren explains. “If it’s a husband and wife or a couple, they can just sit down and go through it together and say, hey, do we want travel to be a big part of our lifestyle in retirement? Do we have big trips that we’re doing? Do we have a vacation home?”
That clarity helps shape the five financial pillars that follow.
Milestone Two: Income
Once the dream is defined, the next question is practical: how much will it cost, and where will that money come from? Loren’s advice is straightforward: “It’s always great to just take a look at: what guaranteed income sources do you have? Do you have a pension? Do you have Social Security?”
If there’s a gap between what you want to spend and what’s coming in, that’s where distribution-focused strategies come in. These strategies work differently than the ones used while you’re still saving.
Social Security decisions, in particular, can make a meaningful difference. “A married couple on average has up to 81 options to choose from,” Loren says.
He recalls one case where “the wife’s Social Security increased about $1,000 per month” simply by identifying a spousal benefit they hadn’t known about. Early awareness—yes, even at 55—gives you time to plan around those choices.
Milestone Three: Taxes
Tax planning is where many people want to turn back. Loren gets it: “People would probably avoid that part of the cave if they could.” But proactive planning brings control. The Merkle Retirement Planning team often starts by projecting what happens if you “did nothing,” then compares it with strategic moves like Roth conversions. The difference can be dramatic.
“In the right circumstances,” Loren says, “people can save over $500,000 (in taxes) if they’re starting with a million-dollar portfolio at retirement.”
He also points out a recent law change (One Big Beautiful Bill) that may benefit some retirees: “Because you’re both 65 and older, married, filing jointly, you’ve got a new $12,000 actual addition to your standard deduction, that’s a senior bonus.”
Small legislative shifts like this can make a major impact—but only if you plan for them.
Milestone Four: Investments
Investment planning isn’t about chasing returns anymore—it’s about positioning for reliability. Market swings feel different when paychecks stop, and your portfolio should reflect that shift. Clint Huntrods sums up the goal: “And who doesn’t want clarity?”
That clarity starts with risk. Measuring how much you’re taking and how much you’re comfortable taking is key. If the market drops 25%, will you stay calm—or will that derail your plan? Adjustments made before retirement can preserve both assets and peace of mind.
Milestone Five: Health Care
Loren admits, “Families often don’t get excited to talk about health care.” But, as he emphasizes, “the health care is a big part of your plan. We want to make sure that you’re prepared for it.”
For anyone hoping to retire before Medicare eligibility, bridge coverage should be part of the budget. That might include COBRA or marketplace options. Planning ahead helps avoid surprises. This part of the plan can feel complex, but walking through it now can lead to more confidence later.
Milestone Six: Legacy
Legacy planning isn’t just for the ultra-wealthy. It’s about protecting what—and who—matters most. Loren reminds families to “begin with the end in mind,” keeping both goals and documentation up to date. “And don’t forget about beneficiary designations,” he warns. “We just worked with an individual recently. She still had her ex-husband listed as 100% primary beneficiary. She said, let’s change that as soon as we can.”
From wills and trusts to powers of attorney, these details form the final piece of the plan—and prevent unintended outcomes later.
The Compass of Clarity
Thread these milestones together, and the path looks far less like a maze. Define the life you want, map income, plan for taxes, understand your investment risk, price health care, and keep legacy documents and beneficiaries current. Along the way, keep an eye out for common misconceptions—assuming you’ll be in a lower bracket by default, ignoring Social Security coordination, or letting outdated forms steer assets where you no longer intend.
In the end, this Indiana Jones-inspired episode artifact—the “compass of clarity”— a framework built around six essential milestones that can help families prepare for retirement with more clarity.
Make decisions in sequence and keep revisiting them, make decisions in sequence, and keep revisiting them as laws and life change. The RetireSecure Roadmap is designed to guide you toward your retirement vision.
Watch the full episode on YouTube and learn about how to start planning for retirement at 55+.
