How Becoming a Student Again Opens Up Possibility and Purpose

After leading one of the nation’s largest independent wealth management firms through a period of extraordinary growth, Bob Oros entered the Leadership & Society Initiative Fellowship expecting a bridge to his next chapter. Instead, he found something more transformative: the opportunity to embrace uncertainty, rediscover learning, and explore purpose beyond a carefully crafted plan. Through deep reflection, intellectual challenge, and meaningful connections with fellow leaders, Bob is reimagining what it means to lead, serve, and grow in this next stage of life.

As Chairman & CEO of Hightower Advisors, Bob Oros presided over a period of exponential growth for one of the country’s largest independent wealth management firms. Between 2019 and 2025, Hightower soared more than 30x, from $57 billion to $1.8 trillion in assets under advisement. When he decided to step down, he was following both a personal plan and a firmly held belief about leadership.

“I’ve long had a philosophy that most leaders stay too long,” he says. “I get why it happens. These are really prestigious jobs. You have power, you have control, and you’re probably not paid too badly either. But I feel like in 5 to 7 years, I have brought whatever unique gifts I have to the role, and then it’s probably time to let someone else bring their unique gifts to it.”

Having led the firm for about six and a half years, he hit his mark square on and made good on a plan he’d nearly forgotten he’d made. “I was talking to an ex-colleague from 20 years ago and he asked if I remembered having told him, back then, that my plan was to retire by 60 and to sit on boards. I didn’t remember, but it didn’t surprise me, because I’m a planner.”

What seemed to Bob like “pie in the sky” two decades ago actually came to be. But he found himself feeling younger than he’d planned to feel at this stage of life. “I would also say I feel younger at 60 than I did at 50,” he says. “I really do believe I’m now in middle life. I’m not in late life, as my parents were at this age. So when I heard that story I thought maybe I’m too much of a planner. Because over-planning takes away some of the variability that you want to expose yourself to.”

Bob credits author and longevity thought leader Chip Connolly with inspiring him to re-consider his path forward after Hightower. “Chip’s view is that there’s this first phase of life which is all around building your capabilities, bigger job, next job, bigger house, nicer car, whatever it is. The next phase is all around what he calls ‘crystallized wisdom’and becoming a modern elder, which is somebody who’s as curious as they are wise,” Bob says. “I started thinking about all of this last fall, before I had even announced publicly that I was leaving Hightower. Then somehow LSI popped into my LinkedIn and I thought this is it. But I actually didn’t understand at that moment why it was it. I thought it would be a great bridge from my work career to my portfolio life.”

But becoming a member of the 2025-26 LSI Design Pathways Fellows cohort has offered Bob far more than a bridge to any predictable place.

“I came into it in September thinking if I had to stand up and do my purpose plan right now, I could do it,” he says, referring to the plans that LSI Fellows develop over the course of their fellowship term. “I was overconfident, because I had a plan; having a plan makes it safe. Having a plan gives you a sense of control,” he says. “I needed to let go of that; let go of control. I needed to get uncomfortable. And so, what I thought of as a bridge has actually completely disrupted me. Which I think was the point.”

As planned, Bob joined a number of boards and began building his new portfolio life (mixing new professional opportunities with philanthropic and personal pursuits) but his experience at LSI has taught him the power of letting plans go and opening to new possibilities.

“Let yourself have that uncertainty. It’s actually a gift. Because the uncertainty is where you get real discovery.” he says, emphasizing the importance of interacting with other Fellows outside of his own field of expertise and the ways in which this has expanded his sense of possibility. “The program’s been unbelievable; I can’t even begin to describe the power of the cohort. It’s like nothing I have ever experienced. These are relationships built on a lot more depth than most of mine had before. It’s been amazing in ways that I didn’t expect.”

The challenges and rewards of shifting his self-identity from a man with a plan to a student with a backpack has been another happy surprise for Bob. “I’ve been learning how to learn again. It is amazing and hard,” he says. “What I didn’t fully appreciate being a CEO was that all the information I got was very synthesized and distilled. Now I have to actually read and comprehend. I’m a business person; I didn’t have a liberal arts background. So I’m reading things I’ve never read before, I’m seeing words I’ve never seen before!”

The fellowship has helped him to build an unexpected new skillset. “You learn how to get some tricks and some structure to get through it,” he says. “Being on a college campus, I just can’t describe how liberating it is, how energizing it is, being around knowledge and students. It’s just hard to fully articulate the value of that, but I completely get why the program is in person. It’s just such a rich experience. It’s been challenging me in ways I haven’t been challenged in a long time.”

He’s found that the challenges can be both broad and intimate in nature and scale. “In the beginning of December, at the end of the term. I had to share with one of my cohort members two minutes on things that scare me and two minutes on things that make me mad,” Bob says. “They’re really simple questions, but to have to look at somebody who’s just inches away from you and talk about these things opens you up in ways we just normally don’t engage. The amount of intimacy and depth of the relationship gets formed really quickly when you do it; it’s amazing what it feels like, and it’s just exploring all these parts of you that are there.”

This uncanny experience of discovery and possibility has been intentionally built into the LSI Fellowship.

Diana Petty, Executive Director of the Leadership Society Initiative sees Bob’s journey as a perfect reflection of the fellowship’s mission to support accomplished leaders in transitioning beyond their primary career arcs into purposeful next chapters characterized by intellectual and personal growth. “We do this through a liberal arts style learning experience built around three pillars: knowing oneself, understanding the world, and envisioning the future,” Diana explains. “The University of Chicago has a very rich tradition steeped in the liberal arts with the belief that critical inquiry and a rigorous intellectual expansiveness are key to shaping better questions and learning how to flex those muscles of fluid intelligence…being able to think more deeply about how to ask and re-ask questions is actually more valuable initially than knowing exactly what the answers might be.”

Not that plans don’t factor into the LSI fellowship. “The capstone of this fellowship experience is what we refer to as a next chapter roadmap, “Diana explains. “Over the course of their time in the fellowship, each Fellow, through this liberal arts exploratory process, is distilling down their why, their what, and their how for this next stage of living and leading purposefully. This is helping them discover the nexus of what they see as their superpowers, the values that are really animating them at this moment in time and where there might be opportunities or unmet needs in the world that they are well-positioned to offer their talents, their wisdom, their capabilities towards. It’s very liberating for Fellows to walk into a 9-month liminal space together, where their only mandate is to discover, to experiment, to reflect, and to trust that in doing that, they will ultimately create for themselves greater clarity and confidence about this next chapter of their lives.”

Bob’s next chapter roadmap and purpose plan currently includes building a portfolio life of professional, personal, and mission-driven growth. “I went into this with a huge passion for mental health,” he says. “This issue had touched me personally and my family, and I wanted to make an impact there. Now I’m shifting towards addressing this on the college level, creating a program around balance, because I’ve observed that especially high-performing students are so over-indexed, they’re losing touch with other things that are really important. So, I’m creating a program that sort of ‘forces functions’ academic excellence with mental health, physical health, with overall wellness, with the idea that kids have enough pressure. They don’t need to come out of college having never experienced building social relationships, having fun. It’s actually a work in process right now with my alma mater, and I’m thankful they’re very engaged in wanting to work with me. I’m not gonna say solve it, because I don’t think you solve anything, but to contribute to making an impact. We want to start with college freshmen, because you then have 4 years to propagate this thinking so we can start to get some exponential impact.”

Diana notes how this sense of a process is key to the LSI experience, paraphrasing President Dwight Eisenhower, “He said that in the Army, he learned that there are no plans, there is only planning,” she says. “So though we use this nomenclature of a purpose plan, it’s a bit of a misnomer for two reasons. One is that there’s no perfect silver bullet of a 9-month fellowship for perfect clarity for the next, possibly, multiple decades of your life. Also, part of the beauty of this life stage is being dynamic, being innovative and iterative. Part of the reason that the liberal arts is so powerful in our context is it sets our Fellows up with a multifaceted toolkit that they can pick up and put down as they go through that iterative cycle. What goes into the purpose plan is their codifying and solidifying their approach, staying grounded in their principles for purposefulness that they’ve set forward. That is their North Star, that is helping them navigate; what is in alignment with their vision and what might not be, and they say no to. We have seen a bit of a spectrum form of the types of visions and approaches that fellows take leaving their time in LSI.”

Diana notes how Bob’s experience reflects the LSI’s “outside-in approach and an inside-out approach” and explains, “what we mean by that is outside-in, there are Fellows who spend their time in LSI with a deep calling of service to a societal need. It ranges very widely. We have fellows working on violence prevention, food insecurity, economic mobility, education reform, it really runs the gamut. Their discernment process is realizing that if they can even move the needle in the smallest way in an area that is of deep, personal meaning to them, that they will derive a sense of purpose, fulfillment, enrichment, and feel like they are purpose-driven in this stage of their lives.

“On the other end of the spectrum, we have a lot of Fellows for whom their big ‘Aha’ and transformative learning moments are more in that knowing oneself side of our curriculum. They have realizations around asking how they can reinvest their own wisdom and activate that outwardly in new ways.”

For Bob, developing self-knowledge has been key. “You gotta know yourself. And you’re going to know a different self as you start to experience it. I had a plan, so that took away anxiety. I’d say it’s okay to have a plan. It’s okay to give yourself some comfort that you can create the thing you think you want. I think it then gives you the courage to push forward. But also to be willing to throw it all away. So create the plan, but be willing to throw it off to the side. I think people just tend to like to play things safe. If you’re going to truly explore yourself and what, at your deepest core, motivates you and gives you joy and satisfaction, you can’t play it safe. You have to get very vulnerable to explore things you haven’t ever explored. But the return for that can be incredible.”

He adds, “Let the journey, the discovery, the instability and the discomfort actually be a joy. You can always come back to what you know.”

To begin your own journey of discovery today, request information about the Leadership & Society Initiative.

This piece was developed in partnership with ROAR Forward. Learn more about ROAR Forward here.

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