Day: November 3, 2025

• About 15 years ago, Vanguard’s chief data analytics officer, Ryan Swann, debated law school.
• Swann said his mentor asked three questions that changed his life — and his mind.
• He said that those thinking about grad school should also consider other paths to achieve their goal.

This as-told-to story is based on a conversation with Ryan Swann, 45, Vanguard’s chief data analytics officer. As law school applications surge, Swann shared how he weighed the decision to go to law school — and why he opted for an MBA instead. This story has been edited for length and clarity.

Throughout my career, I’ve had the opportunity to lean in and raise my hand for the hard things, even if I didn’t know how I would do it.

I was in the Marines while I was in undergrad and 9/11 happened, so I did a tour in Iraq. When I left the military, I entered the public sector and started working for the Department of the Treasury in 2006. In 2008, the financial crisis happened, and I raised my hand to be on the Tiger team, without knowledge about finance or economics.

To this day, the best advice I’ve received is to keep challenging yourself and never stop learning — and that’s what I did.

I had a great experience at the Treasury, and that told me a whole lot about markets that I didn’t know, and I was really intrigued by it. I ended up getting an MBA from Wharton in 2017 and a Master’s in public administration at Harvard in 2019 — but that wasn’t what I originally had in mind.

When I was around 30 years old, I had plans to go to law school. As a believer in life-long learning, I originally wanted to go to law school because I saw how smart data-driven policy could have a meaningful impact.

I took the LSAT, got a great score, and was going to the best law school I could get into. My mentor at the time was a great corporate lawyer, and I went to him to ask for a recommendation. His response blew my mind.

3 questions changed my trajectory

My mentor told me he would write my recommendation, but that nothing about me told him I liked law. Then, he asked me three questions that fundamentally changed my life.

The first question was: What is it that you want to accomplish?

The second question was: What about law is going to help you accomplish that?

The third question was: When you look up in five or 10 years, where do you want to be?

The three prompts made me question why we do the things we do, and whether we’re just chasing something or actually have a passion we want to learn about. That’s how I came back to business school — I had to do the self-reflection to ask myself, what do I need?

It helped me realize that there are multiple ways to achieve my goal. It also helped me uncover some benefits that law school didn’t afford at the time, like going deep on venture capital. As I dug deeper by talking to lawyers and business executives, I realized that I could create value for society in a variety of ways.

The process made me realize that while I’m a public servant at heart, I think like an innovator and entrepreneur. I saw I could expand on my tech background by applying advanced analytics in the business context to create value at large enterprises, startups, and non-profits — which I am doing today.

In my role as chief data analytics officer at Vanguard, I get to apply what I learned from grad school to help drive responsible innovation and deliver meaningful outcomes for our clients. It’s the perfect intersection of purpose, data, and leadership.

Keep learning, even if it’s not in grad school

I would encourage anyone thinking about going to grad school to step back and ask themselves what they are trying to solve and where they see themselves in five to 10 years. Have you talked to the people who are doing what you want to do? Use all that information to make an informed decision.

Sometimes, people look at master’s or business schools and say, “Oh, I need to do that to get there.” But do you really? Have you actually gone and talked about it with someone?

You can learn a lot in places where it’s not a full master’s. You can get a certificate or maybe enroll in a leadership program. Today, information is at your fingertips. You can use generative AI, you can use YouTube, you can use all of these resources to learn things that used to take years of training.

There are a lot of things that you can do. So you should be considerate about where you spend your time, resources, and money to do that. But either way, you should never stop learning. Use the tools, people, and technology available to you to help you grow and develop.

No matter what path you take, you’re going to zigzag your way to success. Success is never a straight line.

• Two partners at Goldman both said they lie awake thinking about their colleagues, or “our people.”
• One also said she still sweats the details, even in such a senior role.
• Goldman Sachs is about to announce new managing directors, shaking up the leadership of its people.

Between billion-dollar investments and global market shocks, partners at Goldman Sachs have no shortage of things to worry about. But two of them share a common nighttime preoccupation.

Business Insider separately asked Meena Lakdawala-Flynn, co-head of Global Private Wealth Management and One Goldman Sachs, and Asahi Pompey, global head of the Office of Corporate Engagement and chair of the Urban Investment Group, what keeps them awake at night.

“I’m always thinking about our people,” said Lakdawala-Flynn, who has been at the firm for more than 25 years and became a partner in 2014. “You’ve built talent, you’ve invested in talent, they’re cultural stewards. To me, it’s about retaining people.”

She added that having a “rotating door” makes it more difficult to create strong businesses and client solutions. Lakdawala-Flynn manages teams of private wealth advisors, who themselves work with the bank’s ultra-high-net-worth clients. As of late last year, Goldman had 39 private wealth management offices around the world.

Pompey, who is nearing two decades at Goldman and became a partner in 2018, also said “our people.”

“You have the careers of all these individuals in your hands,” she said. “Are you doing the very best you can to amplify their talents, give them the opportunities that they need to succeed? I think about that. That keeps me up.”

The firm will, she said, “ultimately win or lose on the back of the talent that we have and the development of that talent.” Pompey oversees initiatives including 10,000 Small Businesses, 10,000 Women, and One Million Black Women.

Goldman is about to announce its next class of managing directors, who sit one rung below partners in the firm’s leadership hierarchy. The bank has come under scrutiny in recent years for an exodus of female leadership and a general lack of women in the most senior positions. Yesterday, CEO David Solomon said Goldman had “made a bunch of progress, especially in the senior ranks, but candidly not enough, and we continue to be focused on creating opportunities.”

Pompey also said that she still worries about the little things when trying to fall asleep.

“The thought that the more senior you get, you somehow don’t sweat the details — I sweat the details about what we’re doing, being stewards of the firm’s resources, that we’re doing it at the highest level for maximum impact, where we should be pivoting or doing things differently,” she said.

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