Fail Forward: Vulnerability, Dealing with Shame, and Self-Compassion

portrait of Ashley Good
Ashley Good is the Founder and CEO of Fail Forward, and in this insightful episode we explore a topic that many avoid — failure. Ashley, an expert in navigating the complexities of failure, discusses why it's essential to confront and discuss our failures, both individually and within organizations. She mentions the isolating nature of failure, the importance of reducing the shame associated with it, and how sharing our vulnerabilities can lead to stronger connections and healing. We also touch on the privilege and societal biases that affect how different people experience and recover from failure, highlighting the importance of offering grace. This episode aims to destigmatize failure and empower you to embrace it as a stepping stone to growth and success.

5 Key Takeaways:

  1. Sharing Our Failures Reduces the Shame: When we experience failure we feel alone. We often think that everyone else has it all figured out except for us and wonder why we can’t do the same. The antidote to this? Sharing our failures when we’re in a psychologically safe environment. Sharing failures openly can make us realize that this experience is universal and can foster a sense of connection.
  2. There’s a Business Case for Embracing Failure: An organization with a culture that supports risk-taking and learning from mistakes can lead to innovation and resilience. In order to do this the organization has to create a safe space where employees can process emotions tied to the failure. Once employees feel heard and understood, then they can discuss what they learned from the failure and move forward – becoming stronger, better, and wiser.
  3. Getting Rid of Our Fear of Failure Isn’t Realistic: What we can do instead is acknowledge our fear and use it as a signal to be better prepared or do more research around the thing we fear. Ask yourself, “What is this feeling trying to warn me about and is this a real risk?” It’s about interrogating the fear to determine whether it’s pointing to a legitimate concern. When we do this due diligence it can motivate us into action so we’re not paralyzed by the fear.
  4. Not All Failures Are Treated Equally: If you look like the person that society expects to see in that job, you’re given the grace of a second chance. People around you will allow you to externalize the blame on outside forces. Unfortunately, if you don’t look like the person society expects to be in that role, the people around you will put the blame on you (e.g. “Oh you weren’t cut out for that role anyway”). If you are this person, don’t take the failure so personally. The best thing we can all do is give everyone the grace of a second chance. 
  5. Give Yourself Time to Grieve When You Fail: Give yourself permission to feel all of your feelings – anger, sadness, disappointment. You need to grieve the loss of what you thought would happen and who you thought you were. The important thing is to not get stuck there. If you’re telling yourself “I’m a failure”, reframe it to “I failed at X.” Remember, you’re still a beautiful, whole human, regardless of your failures. 

Show Notes:

[00:01:23] Ashley elaborates on how discussing failures can reduce the shame and regret tied to them. By expressing these feelings to someone supportive, the emotional burden can be lifted.

[00:01:33] Emphasis on the necessity of risk-taking and stepping out of comfort zones to drive innovation and growth within organizations.

[00:02:46] It’s unrealistic to eliminate the fear of failure entirely. Instead, recognize and manage this fear as part of a thoughtful decision-making process.

[00:06:06] Ashley shares a personal story about taking on a project that was outside her comfort zone. 

[00:07:24] Being open about one’s strengths and weaknesses can actually enhance confidence and trust in professional settings. 

[00:09:52] The importance of asking for help, framing it as a strength rather than a weakness. This approach not only helps individuals but also brings teams closer together.

[00:11:11] Ashley explains that societal biases can lead to certain individuals being unfairly blamed for failures due to not fitting the traditional mold of success. 

[00:12:29] Taking time to process the emotional impact of failure is essential for learning and moving forward.

[00:14:00] The importance of acknowledging mistakes from the top down and the challenges of doing so within an organization.

[00:16:23] Ashley talks about the unique challenges executives face when dealing with failure, particularly the high stakes involved. 

[00:25:55] Not everyone has the same capacity to take risks due to varying levels of privilege and safety nets. 

[00:29:43] Periods of anxiety or depression can make it harder to assess and take risks, highlighting the importance of self-awareness in these moments.

[00:33:37] Ashley provides practical advice for recovering from failure, emphasizing the importance of grieving and processing emotions while avoiding getting stuck in negative self-talk. 

[00:38:00] The importance of celebrating small victories along the way, which can keep teams motivated and provide opportunities for course correction.