Alice Rolli made a truly bold vocational bet in 2023: with no prior experience in elected office, she ran for mayor of Nashville, a major metropolitan city. With an MBA and a background in high growth firms, this was a significant departure, and we talked about her reasons for getting into the race and what she learned along the way. A few insights: 1. The person stopping you is probably you I asked her what holds most people back from making a change when they are unhappy. She described what it was like to be outspent 10-to-1 and find a way to keep going. “The big shots can’t elect you, but they can defeat you. If you spend your time listening to people who say you can’t win, you’ll convince yourself never to do it.” 2. Imposter syndrome lies about who belongs Early in the campaign at a public forum, Alice sat on stage with city council members, state senators, candidates writing seven-figure checks. That unhelpful inner voice whispered: I don’t belong here. Her childhood friend watched from the audience, knowing nothing about Nashville politics. After the event she told Alice, “You’re so much more qualified than all these other people.” The encouragement of people close to her, reminding her what she was capable of during times of self doubt, pushed her to keep going and keep taking risks. 3. Nine nos get you to one yes She often heard in early donor pitch meetings: “I’m supporting someone else.” “Come back when you have more traction.” “I don’t think I’m gonna get involved.” Alice borrowed the Mary Kay principle: you need nine nos to get a yes. Her response: “I appreciate your loyalty. Can I be your first second choice?” Three months after former Senate Majority Leader Bill Frist said no, he texted: “I’m going to send you some money. I want to host an event.” The no meant “not today, not “not ever.” 4. Public failure is more rewarding than private safety After the election, she felt like she’d let supporters down, all the people who invested hours and money and belief. But then she’d encounter people around the city: strangers at Costco, health clinics, football games. They shared messages like, “I voted for you. Don’t give up.” People admire people who stand up for what they believe in. They don’t reject failure. Now Alice leads the Children's Hospital Alliance of Tennessee, advocating for health policy to support non-profit children's hospitals in the state. It’s a role that opened because she was “very publicly unemployed” and willing to take the leap. 5. Operate with singular focus Alice’s husband Michael, a combat veteran, helped her focus by likening the campaign to a combat deployment: “Right now you are deployed. You are not here. You have no responsibilities here [at home]. Go.” It's a worthwhile principle for startups. Companies with founders who have no backup plan get further than those operating with “if this doesn’t work in six weeks, I’ll just drop out.” If you’re stuck where you are, are you operating as if you’re living your backup plan? Where are you hedging?
