When the prospect of another long training run feels daunting, David Sullivan has his own way of keeping himself moving forward.

“I start counting telephone poles,” he says. “When you’re on a street…you’ll see maybe four or five telephone poles in the distance. What I say to myself, who’s miserable and wants to start walking, is just ‘make it to that telephone pole that’s at the end of your eyesight there.’ Then I do it again. And the next thing you know, you’re done.”

It may sound simple, but it’s an approach that has carried Sullivan, 52, across the marathon finish line in Boston three times — and also a mindset he brings to work every day as a wealth management advisor at TIAA, a financial services company known for retirement services and for serving people and institutions in the nonprofit, academic, and cultural sectors.

Helping clients build financial security, he says, isn’t all that different from preparing for a marathon. Both require patience. Both demand consistency. And in both cases, success often comes from focusing on the next step instead of the entire distance ahead.

The first step 

More than a decade ago, Sullivan weighed around 330 pounds and knew he needed to take better care of his health. But like many people facing a daunting goal, he kept finding reasons to put it off — until life forced a shift in perspective. 

His family received news that his 5-year-old niece had been diagnosed with a rare and aggressive form of cancer, with doctors estimating a 2 percent chance of survival. 

As someone who works in finance, Sullivan couldn’t help but think about the odds in practical terms. “I’m a numbers guy, and if I was working with a client saying ‘You have a 2 percent chance of a successful retirement’… that pretty much means it’s not going to work,” he says. 

Watching her fight for her life at such a young age reframed everything. “At the time I was like, ‘She’s been rocked. And I’m here, 330 pounds,’” Sullivan says. 

So, he decided to make a change. After undergoing gastric sleeve surgery, Sullivan began rebuilding his health from the ground up despite the physical challenge. 

“When you are 330 pounds, you physically can’t run,” he says. “You can barely walk a few city blocks.” The first time he managed to run on a treadmill, the moment caught him off guard: “I started crying because I was like, ‘I haven’t done this in… I can’t remember.’”

Those early steps gradually turned into something more structured. A 5K became a 10K, then a half marathon — until one day, his cousin, cofounder of the charity Golf Fights Cancer, encouraged him to aim for the marathon in Boston.

In his first two races, he raised $11,000 for the Children’s Cancer Therapy Development Institute (CCDI). By his third marathon, that total climbed to more than $35,000 — all in honor of his niece, who is now in remission. Her journey, however, and the care it requires, will continue for life. Progress, whether physical or financial, isn’t something you achieve once and move on from. It requires ongoing attention, adjustment, and commitment.

Taking the long road 

For the average person, planning for retirement can feel just as overwhelming as a marathon. But Sullivan knows firsthand the importance of taking a long-term, disciplined approach when helping his clients build toward financial security.

“No one just shows up at the starting line of a marathon who’s never run before saying, ‘Hey, this is going to be a breeze,’” he says. “You do have to build up an endurance.” The same is true financially. “It does take months, not days or weeks to finally get to that starting line and then say ‘I will make it to the finish line.’ It is a journey.”

That journey, he emphasizes, isn’t about quick wins or shortcuts. In both running and financial planning, the temptation to rush the process can often do more harm than good.

“A lot of coaches will tell you go slow and then go slower because you get so amped up,” Sullivan says. 

It’s advice that translates directly to how he works with clients. Rather than chasing fast returns or reacting to short-term market shifts, the focus is on building a plan that can withstand time, uncertainty, and inevitable setbacks.

“There are no shortcuts with this,” he says. “You got to put in the work.”

At TIAA, that work begins with understanding the person behind the plan. The firm’s heritage is rooted in serving people and institutions in the nonprofit world, which Sullivan says shapes the conversations he has with clients. 

For many, the questions are not only about returns. They are about responsibility, stability, and what they want their money to make possible for the people and causes they care about. Sullivan takes time to learn what matters most to his clients, their goals, their concerns, and what they ultimately want their financial lives to support.

“I have to understand what keeps them up at night,” Sullivan says.

From there, the process unfolds deliberately. Plans are built, revisited, and adjusted over time, not unlike a training schedule that evolves as race day approaches.

Beyond the finish line

What begins as something tangible — a number on a scale, a race on a calendar, a retirement target — becomes something less defined, but more meaningful.

That shift happened gradually for Sullivan. The discipline that once felt forced became routine. The milestones that once felt distant became part of a larger rhythm.

“I found that this was much bigger than me,” he says.

Sullivan is quick to point out that none of it happened alone. Family members, friends, and colleagues showed up. That support extended into his workplace as well. At TIAA, colleagues rallied around his fundraising efforts, the company matched donations, and leadership gave him the flexibility he needed to train.

It’s a reflection of a broader culture centered on serving others, something Sullivan sees play out not just internally, but in how the firm approaches its clients.

That idea is central to TIAA Wealth Management’s “Invest in Your Worth” platform. The point is to build something meaningful over time, guided by values, not just numbers. In practice, that can mean starting with what matters most, putting a plan in place, and revisiting it as life changes, with the discipline to stay consistent even when progress feels slow.

In that way, the work mirrors the miles. You don’t get there all at once; you get there by continuing to show up, even when progress feels small. 

Whether it’s training for 26.2 miles or preparing for the future, the approach is the same. Start where you are. Stay consistent. Adjust when needed. Lean on your supporters. And just focus on that next telephone pole.

TIAA Wealth Management products/services are provided by TIAA-CREF Individual and Institutional Services, LLC, member FINRA and a registered investment advisor.  5357071.