Thomas Martin had worked since he was 10 years old, across military service, a stint as a Merrill Lynch investment advisor, and a long career in technology strategy. His informal approach to retirement planning: work until 62 and figure out the rest later.
His wife Leslie had a different instinct. A CPA by background, she knew their numbers. But knowing your numbers and trusting your plan aren’t the same thing.
“You’ve just become this habitual saver,” Leslie said on a recent episode of the Boldin Your Money podcast. “You just kind of put it away because that’s what they told us to do… And I got to a point where I was like, ‘Do we have enough?’”
Neither of them had a real answer.
Do You Need a Financial Planner to Retire, or Can You Do It Yourself?
Retirement planning doesn’t always require hiring a financial planner. Some people want direct advice and a professional set of eyes. Others prefer to run the numbers themselves and stay hands-on as their plans change. The important thing is making informed decisions with enough clarity and confidence to follow through.
Leslie started where her background pointed: Excel. She built their picture out, ran numbers and tests. Then she hit a wall. “I remember sitting there one day and going, there has to be an easier way,” she said.
Thomas suggested hiring an advisor. Leslie pushed back. “I’m a DIYer,” she said. “I wanted to have control over what this is. I don’t want to have to keep running to someone to say, ’Hey, can we do this? What if we do that?’ I really wanted to run the what-ifs.”
A search through YouTube personal finance content led her to Boldin. Planning went from a solo spreadsheet exercise to something they did together. “We started having weekly family meetings,” Thomas recalled. “Leslie would go through what she saw, what she learned, what we might be missing. For a while, it was a weekly thing, sitting down to review what the tools were saying.”
Thomas had worked as an advisor himself. He’d seen how those relationships operated from the inside, and both of them reached the same conclusion. “The questions that would need to be answered were things we had to answer ourselves,” Thomas said. “They’re the same questions an advisor would put to us. So we started working through things on our own.”
Leslie put it more plainly. “I have a thing about paying for parking,” she said. “I don’t want to pay for advice. But I will pay for a tool that makes me more self-sufficient.”
The tools were a way to pressure-test assumptions and get to a level of confidence that general advice couldn’t give them.
How to Know When You Can Retire Early
Thomas had a date in his head for when to retire: 62. But at 58, the job market shifted, his interest in continuing his current path shifted with it, and Leslie’s modeling gave him actual numbers to consider.
“If I couldn’t look at some of the modeling that Leslie had done with the tools,” he said, “I wouldn’t have just said, ‘I think I’m ready.’ I would have said, ‘No, I’m going to go find something different to do or change what I’m doing.’”
There was something else. Thomas’s parents, both active and healthy in their mid-70s, went from swimming competitions to a care home within six months. One developed dementia. The other was diagnosed with ALS.
“I’m 61, I’m not taking anything prescription-wise. I’m somewhat healthy,” Thomas said. “But that could all change tomorrow. So let’s enjoy retirement while we can.”
How Do You Know When It’s Safe to Spend in Retirement?
For people who’ve spent 20 or 30 years saving, spending in retirement can feel like moving away from the habits that got them there. So the instinct is often to wait, or skip certain purchases. What tends to break that pattern is being able to put a number into a tool, watch it move through 10- and 20-year projections, and see the plan hold.
About 90 days after retiring, Thomas got an idea. He wanted a Honda Gold Wing, specifically the 50th anniversary edition, which cost $33,000. In the past, that conversation would have hit a wall.
“Having the plan allows you to have a different type of conversation,” he said. “That can actually go into the plan. Which is a very different discussion than… just my emotional need or desire and a reaction around it.”
The plan didn’t just say they could retire. It gave Thomas permission to spend. “I see and understand how it’s going to play out, worst case, best case,” he added. “I don’t feel paralyzed about not having a direct income anymore.”
Leslie organizes their thinking around what she and Thomas call their go-go, slow-go, and no-go years. The go-go years are now. The Winnebago Rebel they bought before the pandemic, the national parks trips, the fishing. She’s not trying to preserve everything for the end.
“I don’t want to blow the nest egg,” she said, “but I also don’t want to skip something just because I’m worried about money when I’m in the no-go years.”
Research backs this up. An analysis from JP Morgan found that retirement spending usually starts higher in the early years and falls about 5–8% every five years, then levels off in the late 80s and 90s.
Staying Invested When the Market Drops
Leslie came close to pulling everything into cash during the early 2000s downturn. Thomas talked her out of it. “I got scared,” she said. “I thought I’m just going to pull everything out. And Tom said no. I’m thankful for that, because over time things write themselves.”
Staying calm amid market turmoil wasn’t a personality trait they relied on. It came from understanding their exposure. Leslie landed on a clear picture of the two things she could control.
“It’s really about managing your taxable income in retirement and your expenses,” she said. “Those are the two levers. What happens in the market you don’t have control over. So we plan for the worst case. What if we’re in a slump for 10 years?”
Running that scenario in the Boldin Planner, rather than estimating on instinct, gave them a frame for decisions they’d otherwise make out of fear.
Start Your Retirement Plan Before You Think You Need To
Thomas’s retirement planning advice is specific: don’t wait until retirement is close. “Whatever day you think you’re going to retire, have your plan figured out four or five years before that,” he said. “You can then focus on a lot of the other non-financial aspects of retirement prior to getting there,” like building a new social network and activity network.
That way, “if something good happens and it gives you the opportunity to retire, or something bad happens and it causes you to have to retire, you’re not scrambling.”
Leslie keeps it straightforward. “Saving is great,” she said. “But saving with a plan is better. Even if the plan is going to change, you have a better understanding of what you can do and what you want to do. You’re trying to bring those two things together.”
If you’re working through the same question Leslie and Thomas started with, the Boldin Planner lets you model different retirement timelines and spending levels and see how each one flows through your projected income and plan health over time. Get started for free.
Frequently Asked Questions
The best time to start retirement planning is as early as possible, but if you haven’t, now works. Thomas Martin’s advice from his own experience: aim to have a working plan in place at least four or five years before your target retirement date. That window gives you time to run scenarios, make adjustments, and sort out the non-financial side of retirement, your social network, how you’ll spend your time, what the transition will look like, before you actually need those answers.
Knowing whether you have enough to retire comes down to your complete financial picture. You need your savings and investments, your expected Social Security income, any pension or other fixed income, your projected spending, and a realistic sense of how long you might need the money to last. Running those inputs through a planning tool and stress-testing them against bad market scenarios, like a 10-year downturn early in retirement, gives you a much clearer read than any rule of thumb can.
The right withdrawal order in retirement is generally taxable accounts first, then tax-deferred accounts like traditional IRAs and 401(k)s, with Roth accounts last since those withdrawals are tax-free. The actual answer depends on your income picture in a given year, including how Social Security and any required minimum distributions factor in. The goal is to manage your taxable income so you don’t push yourself into a higher bracket or trigger Medicare surcharges you could have avoided.