The Art of Bouncing Back: From Risk Taking to Rejection Resilience

Embracing Rejection and Building Resilience for Lasting Success

A recent chat with My Rejection Story host Alice Draper reveals how entrepreneurs can embrace rejection, build resilience, and turn setbacks into success.

Alice Draper and I connected online through our mutual love of podcasting, partnering with ambitious solopreneurs and knowledge workers and helping others become more skillful at taking risks, facing rejection and building resilience. 


Alice, the brilliant mind behind the "My Rejection Story" podcast, is no stranger to rejection. Our conversation began with a metaphor that stayed with me long after we stopped talking. She likened tackling formidable challenges to diving into the deep end of a pool. Alice, though she admits to lacking formal expertise in human behavior, trusts her intuition—a valuable trait we often underestimate, but one which frequently turns out to be our most accurate guide.

She shared a poignant story about her best friend who faced burnout—a familiar tale for many of us. This friend’s confidence was so severely impacted that it underscored a critical point: sometimes, pursuing ambitious goals immediately after setbacks isn’t the wisest choice. This narrative was a wake-up call, emphasizing how crucial self-awareness and boundary-setting are, especially when we are self employed. Resilience isn’t about constant forward motion; it’s also about knowing when to pause and recalibrate.

One of the most heartfelt parts of our discussion revolved around the power of understanding our "why." Alice recounted how Haley Jakobson, a previous guest on her podcast, discovered her true passion for writing, after pursuing an acting career. Haley’s journey illustrated a profound truth: caring deeply about our goals can help sustain us through the inevitable rejections, because we care enough to persevere. Our motivations are our lifeline, and recognizing them can make the rough seas a bit more navigable.

As two female entrepreneurs, we couldn’t  ignore the gender dynamics at play when it comes to risk taking and rejection. Reflecting on the book, "The Confidence Code," I observed how societal conditioning affects risk tolerance. Men and women approach job applications differently: men often apply even if they only partially meet the criteria, whereas women hesitate unless they fulfill all the requirements. It was a vivid reminder of how past traumas and cultural norms shape our risk-taking behaviors. In professional contexts, as in dating, men are conditioned to handle rejection, seemingly giving them a confidence advantage.

Alice shared a concept that resonated deeply—building a "rejection resilience muscle." Facing small rejections regularly can bolster our ability to handle larger setbacks. Interestingly, research shows that initial rejections often lead to stronger, more captivating proposals later on. Alice highlighted the role of community support in this process. Her participation in a "100 rejection challenge" within a writers’ group demonstrated how celebrating rejections collectively can transform them into badges of honor rather than marks of failure.

We delved into how community and accountability are vital to our entrepreneurial endeavors and provide the needed support to face rejection and build resilience. Alice’s stories about group challenges underscored how collective goals and shared experiences amplify motivation.  Community turns solitary struggles into shared journeys, making the path to resilience less daunting. For those of us with ADHD, challenges can provide the much-needed interest, challenge, novelty, and urgency to create focus and consistency of action.

During our chat, Alice opened up about the sting of personal rejections in the world of PR and visibility strategy. One instance, in particular, stood out: being accused of creating fake familiarity felt more like an attack than a standard rejection. It reminded me of times when my personal quirks, like swearing too much, led to declines. These rejections cut deep because they feel like critiques of our very identities. Yet, Alice’s advice to acknowledge the pain and seek support from trusted friends offered solace and a practical approach to moving forward.

Another key takeaway was the importance of honest feedback. Surrounding ourselves with people who provide constructive criticism, rather than empty validation, is crucial for growth. Alice spoke about insights from the My Rejection Story podcast, revealing that even the most successful individuals grapple with the fear of rejection. It’s a universal and ongoing human experience, irrespective of one’s achievements.

Ironically, we observed how the fear of rejection can increase with success. As expectations rise, so does the pressure to meet them. The initial phases of content creation felt less pressured because the stakes were lower. Now, with heightened visibility, the fear of not living up to past standards can be paralyzing. Navigating this paradox is a challenge many successful female entrepreneurs face.

Towards the end of our conversation, we tackled different approaches to rejection. While building resilience through small steps is widely recommended, I pondered the potential value of diving into significant challenges headfirst. Such bold moves can sometimes spark unexpected growth and insights, pushing us beyond our perceived limitations.

Finally, we touched on the intersectionality of rejection fears. Alice noted that marginalized individuals often face higher levels of doubt and fear. Factors like gender, race, and cultural background add layers of complexity to these fears. Acknowledging this intersectionality is essential in understanding the diverse experiences of rejection and resilience among female entrepreneurs.

As we wrapped up, I couldn’t help but reflect on the multifaceted nature of our journey as female entrepreneurs. Navigating risk, rejection, and resilience is no simple feat. It demands aligning our actions with our core values, understanding our "why," and building a supportive community. Rejections, no matter how personal, are part of the path to resilience and success.

If you'd like to hear the full episode on ADHD-ish Podcast, you can do that here

Diann Wingert

Former psychotherapist turned business coach for ADHD-ish creatives and small business owners.

https://www.diannwingertcoaching.com
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