22-07-2025
How Chasing Rejection Fuels Success For Creative Leaders
Pushing past fear: Embracing rejection can open unexpected doors to growth, creativity and ... More leadership strength.
Do you recall the first time you were professionally rejected? It stung, right? Your ego probably even got bruised while the self-doubt set in, especially as a creative. Did it deter you from trying again, or did it propel you forward?
Sarah Feingold, attorney, professor and playwright behind Dirty Legal Secrets, understands that rejection isn't just unavoidable; it's essential. She even shares her rejection experiences in detail on LinkedIn.
A 2019 study from Northwestern University's Kellogg School of Management found that professionals who openly share setbacks are viewed as stronger leaders. The study highlighted the 'failure boost' effect, where the potential for setbacks leads to future success.
'If I'm not getting rejected,' she explains, 'I'm not putting myself out there enough.'
This year, she set a unique goal of accumulating 50 rejections. Why? It holds her accountable to apply to more playhouses to run her play; the more you put yourself out there, the greater the chance of success.
Sarah Feingold is an attorney, artist, speaker and professor.
Studies from Harvard Business Review and Stanford consistently demonstrate that individuals who actively seek out and embrace rejection build greater resilience, confidence, and creativity over time. Additionally, individuals who regularly face rejection become significantly more innovative.
Years Before The Rejections
As Etsy's first lawyer, Feingold spent over nine years at the company, guiding it through its IPO before becoming general counsel at Vroom. However, the pivotal moment that inspired her transition from lawyer to playwright was the #MeToo movement. Feingold realized that in-house lawyers often hold untold stories about corporate America due to the attorney-client privilege. Frustrated by the silence and secrecy, she initially considered a career in journalism but quickly realized that none of her colleagues would speak openly.
Instead, Feingold gathered anonymous stories and transformed them into theater, seeing the medium as a way for audiences to collectively experience laughter, shock and empathy around issues usually hidden behind legal confidentiality.
Let The Rejections Begin
Dirty Legal Secrets had a rough start. The rejections poured in faster than she could apply for another opportunity. Feingold could have easily given up after the tenth rejection notice, but she began treating each experience as a data point.
'I've learned more from rejections than any success I've had,' she says. 'Rejection means I'm trying. It means I'm in the arena, not on the sidelines.'
Finally, last year the play had its first off-off-Broadway premiere, produced by Cellunova Productions. As the playwright continued to receive rejections from Broadway playhouses, Feingold pivoted her approach by adapting it as a television pilot, with the hope that it becomes a regular series. The storyline centers around the clash between tech startups and their lawyers.
Feingold likens rejection to a muscle, one that strengthens with use: 'The first rejection really stung. But then you keep getting more, and you're like, 'Ok, that doesn't hurt as much.''
A small sampling of Sarah Feingold's rejection collection from her submissions for the "Dirty Legal ... More Secrets" playwright.
How To Leverage Rejection
Reframe rejection by refraining from measuring success solely by wins alone; instead, turn rejection itself into a goal. 'It flips the switch,' Feingold explains. 'Being rejected is the goal, rather than getting the thing. It reverses your brain. I'm looking to get rejected, not just to make progress'.
Feingold emphasizes that clarity is key. 'One of the reasons why I've been able to move forward is because I've been very specific in what I want,' she shares. Clear goals enable targeted attempts, turning rejection into a focused step forward.
'I carefully reflect on each rejection to refine my goals, skills and strategies,' she points out. 'Rejection without reflection is just a missed opportunity.'
Not all rejections are equal. 'I've received some rejections that have been extremely thoughtful,' Feingold notes. There have been some companies that have provided detailed feedback as to why they didn't choose her play. That actionable feedback helped her with her strategy and fine-tuned her pitch.
Feingold treats rejection like any other critical task: it is scheduled and prioritized. 'I carve out time to prioritize and apply,' she states. 'If you don't make the time, you'll never do it.' The discipline of scheduling rejection attempts ensures consistent action rather than sporadic efforts.
Embracing rejection is about harnessing it as a stepping stone to meaningful development. For Feingold, this bold approach has led to sold-out off-Broadway performances and expanded her leadership capabilities.
Adopting rejection as a strategic goal disrupts the typical avoidance mindset. 'I wanted other people to feel like, if they have big goals, they should be getting rejected too,' she emphasizes.
Rejection is uncomfortable; yet, accepting it becomes your strongest path toward success. The next time you hesitate, remember: sometimes the most powerful move you can make is to seek rejection deliberately, knowing that each 'no' brings you closer to your next 'yes.'
'My ultimate goal isn't just the 50 rejections,' she concludes. 'It's to become braver, smarter and bolder in my career.'
