Failing Forward: Why the Psychology of Reinvention Is the Most Underrated Skill Any Leader Can Develop
Rebecca Veksler is a keynote speaker, entrepreneur and founder of SoL Cups, one of the top four reusable cup brands in the world. After a decade of building and scaling a global business, she made the decision to close it on her own terms and rebuild her life from the ground up. She speaks on the psychology of failure, reinvention and resilience through Saxton Speakers Bureau, working with C-suite leaders, founder communities, universities and organisations navigating significant change and transformation.
I spent my entire twenties building a global business from nothing.
I turned thirty not knowing who I was.
The business looked successful from the outside. The offices, the stockists, the corporate partners, the press. All of it was real. And all of it had come at a cost I had not fully reckoned with until I stopped long enough to feel it.
I was depressed. I was in an abusive relationship. I was exhausted in a way that sleep could not fix. And I was terrified, genuinely terrified, to change any of it, because the business had become so intertwined with my identity that I could not imagine who I would be without it.
The decision that changed everything came down to a single question. Am I doing this out of fear, or out of love?
The honest answer was fear. And that was the moment I knew I had to burn it all down.
Why We Stay in Things That Are No Longer Serving Us
The psychology of staying is one of the most underexplored areas in leadership and performance conversations.
We talk endlessly about the psychology of starting. The courage it takes to begin something new. The resilience required to push through the early hard parts. The mindset of the founder, the entrepreneur, the change maker.
What we talk about far less is the psychology of ending. The courage it takes to close something. The identity work required when the thing you built, the role you have held, the version of yourself you have been performing, no longer fits.
And yet this is one of the most common experiences of high achieving people. The leader who has outgrown the organisation they built. The founder who is keeping something alive out of obligation rather than passion. The executive who has been so defined by their title that they cannot imagine who they are without it.
The reason we stay is almost always the same. We mistake fear for wisdom. We tell ourselves we are being strategic, being responsible, being realistic. But underneath those rational explanations is almost always something much simpler: we are scared.
Scared of what people will think. Scared of starting again. Scared that we are not enough without the thing that has defined us.
That fear is human. It is understandable. And it is one of the most expensive things we will ever hold onto.
The Question That Changed Everything
There is a quote that found me at exactly the right moment. If you do not like where you are, move. You are not a tree.
It sounds simple. Almost obvious. But it landed in me like a diagnosis.
Because I had been behaving like a tree. Rooted to a version of my life that I had outgrown, telling myself that the roots were stability when actually they were just familiar.
The other question I started asking myself, the one that I now bring into almost every major decision, is this: am I acting out of fear, or out of love?
Not love in the soft, romantic sense. Love in the sense of genuine alignment with who I am and what I actually want my life to look like. Love in the sense of choosing toward something rather than running away from something else.
When I started applying this question honestly, the answers were confronting. I was staying in an abusive relationship out of fear. I was keeping a business alive out of fear. I was performing a version of myself that I had built for other people out of fear.
Choosing love meant burning all of it down. And it was the most terrifying and the most liberating thing I have ever done.
What Failing Forward Actually Means
Failing forward is not a euphemism for failure. It is not a way of rebranding a bad outcome as something more palatable.
Failing forward is a fundamentally different relationship with difficulty, setback and ending. It is the understanding that what looks like a collapse from the outside is often the necessary precondition for something far more aligned on the other side.
The psychology behind this is well established. Shame, the feeling of I am a failure, consistently produces worse outcomes than guilt, the feeling of I did something that did not work. Shame collapses identity. Guilt drives behaviour change. The leaders who recover fastest and rebuild most powerfully from failure are the ones who can separate what happened from who they are.
This is easier said than done. Particularly for founders and high achievers whose identity is deeply intertwined with their output. When what you have built becomes who you are, losing it feels like losing yourself.
But here is what I discovered on the other side of that loss: I was not starting from zero. I was starting from everything I had already learned.
You Are Not Starting From Scratch. You Are Starting From Everything.
This is the reframe that I believe most profoundly changes the experience of reinvention.
When I closed SoL Cups and began rebuilding, my first instinct was to feel like a beginner again. Like I had gone backwards. Like a decade of work had come to nothing.
But the truth was the opposite.
I understood operations at a level that took a decade to build. I understood consumer psychology, brand strategy, team leadership, global logistics, investor relations, crisis management, and a hundred other things that I could not have understood without having lived them. I had a network, a reputation and a depth of experience that no amount of starting fresh could erase.
What changed was not my capability. What changed was my direction.
And because I was no longer spending my energy maintaining something that had run its course, all of that capability became available for something new.
Within a short time of closing SoL Cups, I had built RLV Projects into a thriving fractional COO and CMO consultancy entirely from reputation and word of mouth. I had co-founded Lumie with one of the most credentialled scientists in the country. I had rebuilt my personal life in ways that I had not believed were possible. I had found the love of my life. I had reconciled with family. I had gotten out of depression and learned, for the first time in a decade, how to rest.
Not because I started from scratch. Because I started from wisdom.
The Psychology of Reinvention for Leaders and Organisations
Everything I have described at a personal level applies equally to organisations navigating transformation, restructure or significant change.
The leaders who navigate change best are the ones who can hold two things at once: genuine grief for what is ending and genuine curiosity about what is becoming possible. They do not minimise the loss. They do not pretend the ending is not hard. But they also do not allow the fear of what is next to keep them rooted to what no longer serves.
The organisations that come through transformation strongest are the ones that treat it as a genuine reinvention rather than just a restructure. That ask not just what needs to change but who do we want to become. That bring their people into the why before they move to the what.
And the leaders who emerge from personal failure most powerfully are the ones who do the identity work. Who are willing to ask honestly: outside of this role, this business, this title, who am I? What do I actually value? What kind of leader do I want to be next?
These are not comfortable questions. But they are the questions that make the next chapter possible.
How to Fail Forward: A Framework for Reinvention
Whether you are a leader navigating a career transition, a founder at a crossroads, or an organisation in the middle of significant change, here is the framework I come back to.
Ask the fear or love question honestly. For every major decision you are sitting with right now, ask yourself: am I choosing this out of fear, or out of genuine alignment with what I want my life and work to look like? The answer will tell you more than any strategic analysis.
Separate what happened from who you are. A failed venture, a closed business, a role that did not work out: these are things that happened. They are not definitions of your worth or your capability. The faster you can make that separation, the faster you can access what you actually learned from the experience.
Inventory what you are taking with you. Before you focus on what you have lost, get rigorous about what you are keeping. The skills, the relationships, the hard won knowledge, the things you now know that you could not have known without having lived through what you just lived through. This is your foundation, not your starting line.
Give yourself permission to grieve and to be excited at the same time. Reinvention is not linear. The grief for what is ending and the excitement for what is possible can coexist. Making space for both is not weakness. It is wisdom.
Choose toward something, not just away from something. The most powerful reinventions I have witnessed are driven by a genuine vision of what is possible, not just a desire to escape what is uncomfortable. Get clear on what you are building toward, and let that pull you forward.
Frequently Asked Questions About Failing Forward and the Psychology of Reinvention
What does failing forward mean? Failing forward means approaching failure, setback and ending not as a final verdict on your worth or capability, but as the necessary precondition for a more aligned next chapter. It is a fundamentally different psychological relationship with difficulty, one that separates what happened from who you are and uses the learning from every ending as the foundation for what comes next.
Why is the ability to fail well so important for leaders? Because every leader who performs at a high level over a long career will face significant failure, setback or transition at some point. The ones who recover fastest and rebuild most powerfully are not the ones who never fail. They are the ones who have developed the psychological capacity to process failure without collapsing their identity around it, to extract the learning, and to move forward with genuine clarity about what they want next.
What is the psychology of reinvention? The psychology of reinvention involves the identity work of separating who you are from what you have built or the role you have held, the grief work of genuinely processing what is ending, and the future focused work of getting clear on what is becoming possible. It requires the capacity to hold loss and possibility at the same time, and the courage to choose toward something genuinely aligned rather than staying rooted in something familiar out of fear.
How do you rebuild after closing a business or a major life change? The most important reframe is this: you are not starting from scratch, you are starting from everything you have already learned. The skills, relationships, knowledge and hard won experience you have accumulated do not disappear when a chapter ends. Inventory what you are taking with you, separate what happened from who you are, and get clear on what you are building toward, not just what you are moving away from.
What is the difference between shame and guilt in the context of failure? Shame is the feeling of I am a failure. It collapses identity and consistently produces worse outcomes. Guilt is the feeling of I did something that did not work. It preserves identity while driving behaviour change. The leaders who fail forward most powerfully are the ones who can process what happened through the lens of guilt, learning and accountability, rather than shame and self definition.
What does Rebecca Veksler speak about regarding failure and reinvention? Rebecca Veksler speaks on the psychology of failure, reinvention and what it takes to rebuild more powerfully after a significant ending. Drawing on her own experience of closing a decade long global business, leaving an abusive relationship and rebuilding her life and career from the ground up, she speaks for C-suite leaders, founder audiences, universities and organisations navigating transformation and change. Her session Failing Forward: The Psychology of Reinvention is available as a keynote, fireside or workshop through Saxton Speakers Bureau.
Rebecca Veksler is a keynote speaker, entrepreneur and fractional COO and CMO. She founded SoL Cups, one of the world's top four reusable cup brands, and speaks on the psychology of reinvention, resilience and consumer psychology through Saxton Speakers Bureau. To enquire about bookings, visit rebeccaveksler.com