Mark Eakle had two people at work he trusted. When he was 42 and his employer shifted from a pension to a 401(k), those colleagues pulled him aside and told him something that stuck: get the match, be happy with 7%, and take the long view. That advice became the foundation of a DIY retirement planning approach he now shares with a small group of peers who trust each other with their actual numbers.
The importance of financial planning and literacy “has changed in my lifetime,” Mark remarked on a recent episode of the Boldin Your Money podcast. “My father came at a time when companies really took care of this for you. That transitioned…. I kind of lived through that transition.”
It was a pivotal moment that led to decades of learning… and a retirement plan that finally clicked into place.
When to Start Retirement Planning
The best time to start retirement planning is before retirement feels urgent. Early on, that might mean a fee-based advisor or a ballpark projection. Even a rough early plan that maps your savings gaps and a target window means you’re preparing at pace rather than under pressure. The habits you develop are what make self-directed planning possible later.
Mark didn’t wait until retirement felt close and he had to scramble, though how he got there wasn’t obvious from the start. When the pension ended, his employer offered training sessions and most people absorbed the basics and moved on. Mark listened more carefully to the two colleagues who told him to stay consistent and let compounding do its job over time.
He also found a fee-based advisor who helped him sketch out what the road ahead could look like. The projection was specific: pay off the house and get the kids through college without debt, and you’ll hit a window to accelerate. That window was the whole point.
“He just kind of predicted it and painted a picture,” Mark recalled. “We were able to embrace it when the time came.”
How to Catch Up on Retirement Savings in Your 50s
Catching up on retirement saving in your 50s often means eliminating expenses and obligations that compete with it. Reduced obligations can make this the most productive saving window of a career. Once the mortgage and major expenses are behind you, workers 50 and older can take advantage of catch-up contribution rules that allow higher annual limits in 401(k)s and IRAs. (The IRS sometimes adjusts these limits, so it’s worth checking the current figures before you plan your contributions.)
That’s the window Mark’s fee-based advisor had sketched out years earlier. The mortgage was gone and he had gotten his daughters through college without debt. With two incomes and no major obligations pulling them sideways, he and his wife finally had the room to move.
They’d kept the match without fail throughout, even during the years when the mortgage and tuition took everything else. When the window finally arrived, it was exactly what the advisor had called it: catch-up in the true sense.
“Two incomes, you have that choice now,” he said. “You can say, I want to accelerate.”
That’s when maxing out accounts in earnest becomes possible.
How to Build Confidence in Your DIY Retirement Plan
Gaining confidence in a DIY retirement plan comes from understanding it well enough to explain it, not just follow it. That means knowing why your allocation is what it is, and how your income sources hold up if markets drop for a decade. The turning point for most people is when they can run their own scenarios and check the work.
Mark worked with an advisor for years, and at some point the relationship changed. Then he moved toward DIY retirement planning tools he could run himself.
“The one thing that surfaced to the top of importance for me is that confidence to embrace the do-it-yourself,” he said.
The question most people face isn’t really advisor versus no advisor. It’s whether you understand your own plan well enough to make decisions without flinching. Mark’s answer landed somewhere specific. “Don’t go alone,” he said. “And don’t go in the dark.”
That means understanding the incentives behind your advisor’s recommendations and having tools to check the work yourself. The Boldin Planner gave him a way to do that. “We really know everything,” he said. “We feel like we’re solid.”
That kind of confidence comes from seeing how the numbers hold up under bad conditions, which is a different thing from hoping bad conditions don’t come.
DIY Retirement Planning Doesn’t Mean Going It Alone
It can be helpful for DIY retirement planning to involve a small, private group of peers at a similar life stage. People who share their actual plans and work through big decisions together can offer accountability and honest feedback that’s hard to find elsewhere. The only requirements are mutual trust and a commitment to keep what’s shared private.
Mark joined the Boldin Facebook community and came across a post with a specific suggestion: let’s form a small group, maybe eight or ten people, meet once a month, and agree to keep what we hear in the room. Bring your plan details and talk about real decisions.
He was the last person invited to join the group, and it’s been running for more than a year and a half. “That ability to talk to somebody else doing the same effort with similar goals, different strengths, and different experiences has just been incredible,” Mark said.
The group includes an economist, a CPA, people still working, and people already retired. The ones who have crossed over come back and report what year two looked like, what they got right and what they missed. When a member recently picked a retirement date and followed through, the group celebrated the milestone. “He got to have the first 10 minutes of the next meeting to let us applaud the success and then watch the relief,” Mark said.
The group also has a protocol for big decisions they call the gut-buster. If you’ve got a consequential choice coming up, you bring it to the group, walk through it, and ask what you might be missing. It’s the same thing a good advisor does in a review meeting, but with people who have no stake in the answer except getting it right.
DIY Retirement Planning Advice for Anyone Starting Out
If you ask Mark what he’d tell someone earlier in their financial life, the list is clear:
- Get the match without fail
- Don’t underestimate what debt costs you
- Understand compounding and give it time to work
- Have people in your life you can talk money with
That last one is what he comes back to most, connecting with others without posturing or pretense.
“It’s an independent set of eyes to look at what you’re doing to help you think it through,” he said. That process of discussing your plan with peers and going back to update the numbers is what turns retirement planning into something you stay curious about.
“I had a mild interest in the beginning, and every little bit of progress enticed more interest and more education, and now it’s kind of fun,” he said. “Even if it’s simple, just have a plan.”
The Boldin Planner helped Mark get to a place where he understood his own retirement planning well enough to own it. Work through your own numbers until you can say the same.
Frequently Asked Questions About DIY Retirement Planning
DIY retirement planning is the practice of managing your own retirement strategy rather than delegating decisions to a financial advisor. This involves tracking your savings, modeling your income sources, stress-testing your assumptions, and adjusting your plan as your situation changes. Doing it yourself means understanding your numbers well enough to own your decisions.
Starting retirement savings in your 40s or 50s still leaves a meaningful accumulation window. The years after the mortgage is paid and the kids are through school can become your highest-saving period, especially with catch-up contribution rules that let workers 50 and older contribute at higher annual limits in 401(k)s and IRAs. What matters most at that stage is clearing the debt that competes with savings and redirecting that money.
A retirement peer group is a small, private group of people at a similar life stage who meet to share their actual plans, push back on each other’s assumptions, and work through big decisions together. Participants typically agree to keep each other’s numbers confidential. Some form through communities like the Boldin Facebook group and others come together through local professional connections.
Knowing when to move from a financial advisor to managing your own retirement plan comes down to whether you can explain the plan you’re in. If you can’t articulate your allocation or say what would happen if markets dropped for a decade, you’re probably not ready to go independent.
Staying disciplined with retirement savings when markets drop is mostly a function of knowing what you own and why you own it. Panic-selling tends to happen when someone has no clear picture of how their plan holds up under pressure, and running a stress scenario before a downturn hits rather than during one changes how you respond to it.