Lessons from Leaders: Career Pivots, Risk-Taking, and the Unexpected Moments That Change Everything

Career advice every marketer should hear

Most career-defining moments aren’t meticulously planned—they often arise from unexpected opportunities, a twist of fate, or the courage to take a leap without knowing exactly where you'll land. In this post, we explore powerful lessons from two 621 leaders who’ve navigated pivotal career shifts.

Scott and Simon’s paths nearly crossed at Clorox, but their careers truly converged at Pure Digital, the startup behind the Flip Video camcorder. Their journey – from corporate roles to entrepreneurial risk – offers valuable insights into seizing the right opportunities, even when the future is uncertain.

In this post, the first in a leadership series, we explore the key decisions that propelled them from corporate careers to the dynamic world of startups—and the lessons they learned along the way.

Scott and Simon on an outing with the Flip team in 2008. Scott is 4th from the left and Simon is 3rd from the right, both in the top row.

Finding Opportunity in the Unexpected

Career shifts can start from seemingly random, serendipitous events. Scott recalls an early experience in college: “I accidentally put my resume in the wrong box while applying for internships, which landed me on Wall Street for a summer and changed my entire career trajectory. While I realized that I didn’t want to go into finance as a career path, the role helped me position myself for management consulting jobs after graduation.”

Simon had a similar experience: “When I started my career, I wasn't exactly sure what I wanted to do – law school seemed like a good bet, but I decided to test the waters first. I signed up for interviews and landed at Swander, Pace, and Company, a highly regarded consulting firm specializing in consumer packaged goods. After two years there, I was put on an exciting project for Clorox, after which their Marketing Director asked if I’d be interested in joining an incoming brand management class. It felt like a shortcut to growth, even though I'd be the only one without a traditional business-school background. I took the leap – a door opened and I had the faith to walk through it.” 

Opportunities aren’t just about landing a new job – we can find them by recognizing ways to grow and evolve within your current workplace.

“Early in my career, I chose Clorox over joining a dotcom, even at the height of the boom, because I knew I’d get a foundation in brand-building, general management, and leadership that would last,” Scott says. “I was fortunate that every time I was ready for a new challenge, Clorox gave me the chance to stretch into a new assignment, enabling me to grow across functions and responsibilities.”

Taking Calculated Risks

Growth often comes from stepping outside your comfort zone. Simon experienced this when choosing between a stable marketing role at Leapfrog, where he could continue working with his longtime mentor, and the chance to step into his first head of marketing role at the early-stage startup Pure Digital. “It wasn’t just a job change – it was a defining leap toward becoming a CMO,” he says. “That decision shaped the rest of my career and ultimately gave me the opportunity to bring Scott into Pure Digital down the line.”

Scott faced a similar decision when leaving Clorox after seven years - with a newborn at home:

“I had the chance to help launch a brand from scratch by joining Pure Digital,” he says. “Simon was the one who encouraged me to take the leap – he made the opportunity feel possible. Even though I had a new (very colicky) baby and plenty of personal responsibilities, I knew I couldn’t wait for a 'perfect' moment. I was clear in my mind: I wasn’t ready to optimize just for stability. It was time to take a risk.”

Both Simon and Scott agree: When you take a professional risk, you’re not just betting on the opportunity – you’re also betting on the people.

“I knew Simon would have my back, and we’d work well together,” Scott says. “You should always assume the business and your role will evolve, especially at a startup, so you want to ensure you connect with the people, mission, and values. That alignment makes the risk worth it – and makes it more likely you’ll succeed when the realities on the ground inevitably shift.”

Balancing Impact and Stability

Marketers often face a critical decision between the stability of corporate roles and the entrepreneurial spirit of startups. Scott describes leaving Clorox to join Simon at Pure Digital as “a leap into the unknown, testing if I could succeed without the safety net of readily accessible data and resources. Transitioning to a startup meant learning to embrace uncertainty.”

Simon experienced this same struggle when moving from consumer packaged goods into the education space, driven by personal passion.

“The company had about $3 million in revenue but had a confusing early-learning product line-up and branding,” he says. “Using insights from focus groups, I led the team to streamline seven products into three clear, age-focused titles. Within a year, revenues surged to $40 million, changing the trajectory of the company. This experience showed me the power of following my passion, trusting the marketing skills I had learned at Clorox, and the real impact I could have by taking risks. Ultimately, our success led to an acquisition.”

Simon also points out that our personal influence on the direction of an organization can emerge gradually as companies evolve and grow. "For me, impact wasn't just about immediate influence – it was about creating something that could grow over time. Joining organizations early, building teams with talented people like Scott, and seeing where the journey went, became a defining and rewarding aspect of my career."

Making the Right Career Move, Even When the Path Isn't Clear

If you’re considering a big career change, complement intuition with research and due diligence. Ask yourself if you’re seeking impact, stability, or growth – and be honest about your priorities for the next phase of your career.

Ultimately, careers are rarely linear or predictable. Sometimes, the best career move you’ll ever make starts with simply having the courage to step into the unknown.

Considering moves of your own? Learn more about fractional marketing and the power of building flexibility, passion and impact in your career – contact us anytime.