Request Information from Booth

Loading...

  • Select
  • Submit
  • Success
Sumit Singh speaking at Chicago Booth's MBA graduation

Taking Mindful Risks

Chewy’s Sumit Singh, ’14, reflected on the rewards of nonlinear career paths at this year’s graduation.

How do you weigh the pros and cons of a pivotal career move? What separates the right career decisions from the wrong ones? For Sumit Singh, ’14, CEO of Florida-based online pet retailer Chewy, the key is “intelligent risks.”

In a commencement speech to Chicago Booth’s 2024 graduates, Singh shared the logic behind the choices that shaped his career trajectory. No matter your path, Singh said, confidence, humility, and lifelong learning will transform any detour into a meaningful career step.

Here are Singh’s three pieces of advice for navigating challenging moments throughout your career.

Never Stop Learning

Sumit Singh headshot
Sumit Singh

I have two degrees in industrial engineering with a focus on supply chains. Yet, I am one of the youngest CEOs to grow a startup into a Fortune 500 company. How did that happen? By making nonlinear career decisions. Pursuing a nonlinear path is different from job hopping or aimless wandering. It’s about amassing skills, even if you’re not exactly sure what you will use them for just yet.

Early in my career, after a couple of years in engineering, I took on an operations-management position at an assembly plant. As a 24-year-old, I got to learn about managing and leading people in a fast-paced environment. That turned out to be invaluable. Much later in my career, I’d gotten pretty good at those people skills. But I gave up managing a large team to take on a new role—building a venture from the ground up. I had to test my chops in a new way. And that experience, too, has been an incredible tool to have in my leadership belt.

It is helpful to think of your career as a collection of skills that you amass over the long run and to keep learning what you don’t know instead of relying on what you do know. Not everything will connect in the short run, but if you’re considered in your choices, your experiences will blend like colors in a painting. And the overall picture will turn out to be quite powerful.

Balance Judgment and Risk-Taking


The first principle of developing good judgment is to gain varied experiences and to live in a feedback loop of continuous evaluation and improvement. It is inevitable that you will find yourself in situations where you do not have perfect information. This is where risk-taking comes into play.

Before joining Chewy, I worked at Amazon in Seattle. I had a global job leading a large team with significant P&L [profit and loss] responsibility. That’s when I was approached by Chewy for a job in Florida. It wasn’t a CEO job. Chewy was an unknown startup at the time, and it was led by an unknown founding team. My compensation would be one-third of what I was making at Amazon. As one of my mentors put it, “I wouldn’t touch this with a 10 ft. pole.”

But my instinct kept nagging at me, telling me there was something there. Critically, my wife was supportive, which really mattered. So I took the job, and our family moved from Seattle to Florida. My risky choice was based on more than just instinct. I assessed the risk based on three factors:

  1. Opportunity. I believed Chewy had a strong founding base and good overall financial discipline, and that the pet category was transitioning online.
  2. Self-confidence. I believed that I could make a real impact on the trajectory of the company and on the culture of the organization.
  3. Comfort in failure. I knew I didn’t have the full picture, but I was comfortable with the unknown, with accepting that Chewy might fail, and I might fail.

Now, Chewy has grown fivefold in revenue, approaching more than $12 billion with over 20,000 employees. We’re a public Fortune 500 company, one of the largest direct-to-consumer brands in the United States, and debt free.

“It is helpful to think of your career as a collection of skills that you amass over the long run and to keep learning what you don’t know instead of relying on what you do know.”

— Sumit Singh

Be Humble in the Face of Failure and Success


No matter how hard you’ve worked, we all need humility when it comes to success and when it comes to failure. I believe that luck—serendipity; right time, right place—is a real and powerful element in every life journey and in every professional journey. There are factors operating beyond our control and field of vision. Blaming yourself for these factors when they go against you is unfair. And taking credit when they’re in your favor is unwise.

The mind games we play with ourselves about success and failure can be an easy trap to fall into. But if we can be ruthlessly honest with ourselves, we can stay grounded in any environment.

Failure is inevitable, so don’t despair when things don’t work out. Learn from it and accept it. Similarly, stay humble when you achieve success. Be grateful for the good fortune that has come your way.


This essay is adapted from Singh’s speech at Chicago Booth’s 2024 Graduation Ceremony for the Evening, Weekend, and Executive MBA Programs.

An excerpt of this essay appeared in the Fall 2024 print issue of Chicago Booth Magazine as “Painting the Big Picture.”

Related Topics

More Stories from Chicago Booth

Email icon

Booth News & Events to Your Inbox

Stay informed with Booth's newsletter, event notifications, and regular updates featuring faculty research and stories of leadership and impact.

YOUR PRIVACY
We want to demonstrate our commitment to your privacy. Please review Chicago Booth's privacy notice, which provides information explaining how and why we collect particular information when you visit our website.