293: Why You Cannot Fail Forward Alone

Why You Cannot Fail Forward Alone

Selective visibility strategist and business mentor Cindy Gordon delivers the version of failing forward that the motivational posters never tell you about. Failing forward is not a mindset. It is a skill. And it is one most experienced entrepreneurs are quietly bad at, even when they look fluent at it from the outside.

In this episode, you'll discover:

• Why "failing forward" as it is commonly taught rarely produces actual forward motion
• The difference between failing forward and failing past (and the sinking feeling that tells you which one you have been doing)
• The behavior analyst reframe: failure as data, not character, and what changes when you treat it that way
• Why you cannot analyze your own failures cleanly, no matter how self-aware you are
• The three analytical questions to ask yourself about any recent failure
• How to know whether you have the right witness in your business yet

Perfect for: female entrepreneurs and small business owners who have had real failures, real losses, real launches that did not work, and who suspect that the "dust yourself off and try again" version of failing forward did not actually teach them what they needed to learn. There is a more rigorous way to do this work, and it starts with not doing it alone.

Episode Highlights: "Failing forward is not a mindset. It is a skill. And it is one most experienced entrepreneurs are quietly bad at, even when they look fluent at it from the outside." "The most valuable analysis of my own failures rarely came from me. It came from the people I trusted to see my business clearly when I could not." "The entrepreneurs I see compounding their growth are the ones who have built systems and relationships that surface their patterns for them. The ones still trying to do this work in their own heads are usually moving sideways while telling themselves they are moving forward."

Resources mentioned:

• Weekly Thursday newsletter for 1,500+ entrepreneurs (link in show notes)

Failing forward is fundamentally about accuracy. Resilience is just the side effect.

Connect: @exclusivelycindy on Instagram  - BOOK a Strategy Session

About Your Host: Cindy Gordon is a Selective Visibility Strategist and 6x online business owner behind Exclusively Cindy. With a Masters in Special Education and training in Behavior Analysis, she takes an individualized approach to visibility, helping female digital entrepreneurs decide what they stand for, where they show up, and how. 

Learn more at exclusivelycindy.com

💌  Join 1,500+ entrepreneurs receiving weekly strategic insights and business clarity frameworks - sign up now! https://cindygordon.myflodesk.com/countmein

Transcript

Speaker 0:00

Failing forward is one of the Most overused phrases in business right now. You've probably heard it a hundred times. Fail fast, fail often, failure's your teacher, all of it, and almost none of it has actually helped you. Because if you are like most business owners, you have had real failures, launches that didn't work, investments that didn't return, decisions that cost you something you cannot get back, and the motivational version of failing forward did not give you the actual tools you need to extract anything useful from those moments. It just told you to feel better and try again. Hi, I'm Cindy Gordon, a selective visibility strategist and business mentor. I built and sold several businesses, which means I have actually failed in public, in private, and in ways I did not see coming. I think what I wish someone would've told me when I was starting out is that failing forward is not a mindset. It is an actual skill, and it is one that most business owners are quietly bad at, even if they look fluent at it from the outside. So today I wanna give you a version of failing forward that actually works, the behavioral science version, not the motivational poster version. And just a reminder, every Thursday I send out this kind of strategic insights that make business owners actually stop and think. Over fifteen hundred of them look forward to it every single week. Link in the show notes if you want to join us. The story most business owners have been told about failure goes like this: something didn't work, you feel bad for a minute, you pick yourself up, you dust yourself off, you learn the lesson, and you try again, but better next time. That is the story, and it almost never is actually what happens. What actually happens is this. Something doesn't work, you feel bad for longer than you care to admit, you scramble to rationalize what happened so you can stop feeling bad. Then you attach a story to it that is just neat enough to share on social media, and then you move on without ever doing the real analysis of what actually went wrong because the real analysis is uncomfortable. and the rationalization is not That is not failing forward. That is failing past. The lesson never gets extracted. The pattern never gets seen, and the same failure shows up six months later in a slightly different shape, and you call it a different problem. If you have ever had that sinking feeling of, "Wait, this is familiar," while making a business decision, that is a signal that a previous failure did not actually get processed. It got rationalized, and there is a big difference there. So you may or may not know that I have a background in behavior analysis. The discipline trains you to look at behavior as data, not a personality, not as a moral failure, but just data, information. So when I evaluate a client or a customer's situation, I look at the behavior in the same way. The decision that they made, the pattern they kept falling into, the investment that didn't return the way that they thought it would. So none of it is about who they are as a person. It is all information about what is happening in the system. So this is the reframe that most business owners need. Failure is information about a specific decision in a specific moment with specific inputs. And when you treat it as data, you can analyze it and learn from it. When you treat it as a character, you bury it. And buried failures are the most dangerous ones because they keep showing up and creeping up over and over again. Failing forward as a practice looks like this. You name the actual failure aloud, so not the spin, but the actual thing, the launch that flopped or the investment that did not return, the decision that cost you. So naming it out loud accurately is your first move. And then you're gonna ask some questions about it. What specifically did I assume here that turned out to be untrue? What was the input I was missing that would have changed the decision? These are questions that actually teach you something, and then you take it to someone who can actually see it a little bit more clearly than you, because sometimes we're a little bit too close. This is a step that most business owners skip, and the step that turns a failure into an actual forward motion. The witness who sees the pattern that you cannot see. If you do not have a witness in your business right now, this is worth noticing. Smart business owners don't assume that their own analysis is enough. They always build in a second pair of eyes. This can be something as simple as your business bestie, a coach, or even a mastermind group of women who are building something similar to you. Failing forward is fundamentally about accuracy. Resilience is just a side effect. The work is seeing the actual thing that happened, extracting the actual pattern, and making a different decision the next time the same input shows up. The accuracy is rarely possible alone. The business owners I see compounding their growth are the ones who have built systems and relationships that surface the patterns for them. The ones that are still trying to do the work in their own heads are usually moving a little bit sideways and telling themselves they're moving forward. So here is a thing I want you to sit with today. I want you to pick one failure from the last six months in your business. Resist the version of the story that you have already told yourself about it. Instead, ask yourself, "What input was I missing? What pattern is this part of? And who do I trust to actually look at this with me?" If the third question is harder to answer than the first two, that is also your work for the next quarter in identifying where your second set of eyes could be. That's all I have for today. Thank you so much for listening. This is The Strategic Entrepreneur.