At 25 years old, Molly Graham was thriving in Facebook’s HR department when a senior executive urged her to transfer out of her stable role and help build a mobile phone instead.
She took the risk — and it could have derailed her career.
But Graham, who later became a C-suite executive at some of America’s biggest companies and philanthropies, now views that risky bet as one of the most important moves she ever made.
“It just felt like falling off a cliff,” Graham, now the founder of Glue Club, said in a recent interview on Lenny Rachitsky’s podcast. “Taking risks, accepting the terrible fall and that experience of falling has been more than worth it.”
Graham described the experience as part of what she calls the “J-curve” — a career trajectory where a risky move leads to an initial drop before eventually producing outsized gains. Visually, she describes it as standing on a ledge, stepping off, sinking briefly, and then rising far higher than where you started — just like the shape of the letter J.
The concept, which she has also written about in her Lessons Substack, challenges the idea of a steady career ladder that steadily moves up and to the right.
Instead of climbing rung by rung with promotions every two to five years, Graham argues that some of the most valuable professional growth comes from jumping into roles you aren’t ready for and surviving any setbacks.
Graham’s own J-curve began when billionaire investor and “All-in” podcast host Chamath Palihapitiya, then Facebook’s vice president of growth, recruited her to help develop a smartphone, encouraging her to make the move by sketching out the J-shaped trajectory on a whiteboard.
He brought her on despite her having no experience in product development, dropping her into rooms filled with engineers and phone specialists with deep subject matter expertise. She recalled feeling like an “idiot” for much of her first six months.
Molly Graham
At her midyear review, Palihapitiya delivered what Graham called the worst performance evaluation she had ever received. But the new experience eventually expanded her expertise.
“Slowly, I remember I had been doing all these trips to Taiwan because we were actually working on hardware and I, at some point, came back from Taiwan and I like drew on a whiteboard for him the layout of a mobile phone, trying to explain to him kind of like why something he wanted to do was not possible,” Graham said. “And I so vividly remember walking out of that meeting being like, ‘Oh like I actually know things.’ And slowly then over the following three years I became an expert in mobile.”
Palihapitiya did not respond to Business Insider’s request for comment.
“The phone itself was a giant failure — a massive, costly failure for Facebook,” Graham told Rachitsky on the podcast. “But it was not a failure for me.”
She credits the experience with teaching her that she could operate far outside her comfort zone — a lesson that later helped her take on senior leadership roles, including serving as COO of Quip, which Salesforce acquired for $750 million, and overseeing operations at the $7.4 billion Chan Zuckerberg Initiative.
The J-curve, Graham said, is especially common at fast-moving companies like Meta, Alphabet, Nvidia, and SpaceX, where leaders value employees who are willing to take big risks early and learn quickly. In those environments, proving adaptability can matter more than checking every qualification box.
Not everyone supported Graham’s decision at the time. She said Facebook COO Sheryl Sandberg, then the number two at the tech giant, advised against the move — as did her father.
“When wiser, more experienced people questioned the job offer, it definitely made me pause,” Graham told Business Insider in a follow-up email. “But my gut felt really strongly that I needed to take the risk.”
That instinct, she said, ultimately helped her discover what kind of work she didn’t want to do, and where her strengths lay. She didn’t want to sift through mock ups of hardware design and argue about a button’s placement. Instead, she sharpened her management skills and prepared to help lead large organizations.
“The much more fun careers are like jumping off cliffs,” Graham told Rachitsky. “They can take you to places that you never could have imagined.”
