The Move That Almost Failed — But Didn’t with Victoria Hartman

0:00Every business story has moments that feel like they could break you. The decisions that haunt you in the quiet hours. The strategies that seem brilliant on paper, but terrifying in execution. Most of the time, these moments don't get told. They're hidden behind quarterly reports and LinkedIn posts. Today's episode is about one of those moments. A move that almost failed, but didn't. A decision that carried immense risk, where the stakes were high, the consequences real, and the outcome uncertain. And yet, somehow, it worked. Victoria, welcome to the show. It's great to have you here.

0:37Victoria Hartman:Thank you, Shane. When I think back to that period, I remember feeling like I was standing on a cliff, looking at two very different paths. One was safe, predictable, and boring. The other was risky, messy, and could have destroyed everything we had built. The decision wasn't sudden. It was the result of months of small signals, incremental problems, and late nights questioning my own judgment. Our team was growing, the market was shifting, and what had worked before suddenly wasn't enough. I knew that if we didn't act, we'd stagnate, but acting felt terrifying. Every scenario in my head ended with failure, financial, reputational, and emotional.

1:25So you were carrying both responsibility and fear simultaneously. That's a heavy place to lead from.

1:32Victoria Hartman:It was. Every email, every meeting, every product discussion became a microcosm of the bigger dilemma. I would walk into the office in the morning with a plan, and by the afternoon, second-guess myself. It felt like we were moving through molasses. Everything required twice the energy, and yet nothing seemed certain. Talk me through that internal struggle. How did you process it? Honestly, it was a constant cycle of anxiety and reflection. I questioned whether I was overreacting, whether I was being reckless, or whether my instincts were right. I'd have conversations with my leadership team where I felt I needed to project total confidence, but inside, I was full of doubt.

2:20Victoria Hartman:I remember one night, sitting in my office after everyone left, staring at the spreadsheets and projections, feeling the weight of every person who depended on this company. It wasn't just the numbers. It was their livelihoods, their belief in me, the trust my investors had placed in me. And in that moment, the idea of making the move felt simultaneously inevitable and impossible. That tension between inevitability and impossibility is where most leaders crack. How did you hold it together? I realized that indecision was its own failure. If I didn't choose, the business would slowly erode. I had to lean into the fear, not ignore it.

3:04Victoria Hartman:That meant accepting the possibility of failure and preparing to act anyway. So the move itself, what was it and how did you decide to take it? It was a major pivot in our strategy, a reallocation of resources that felt counterintuitive to everyone but me. We were betting on one product line, one market segment, and a completely new marketing approach. On paper, it looked risky, and for weeks I couldn't sleep without running worst-case scenarios over and over in my head. But at some point, I realized that almost failed is part of every bold decision. The fear itself doesn't mean it's wrong. It just means it matters.

3:47Victoria Hartman:I called a few key advisors, shared my plan, asked for brutal feedback, and then committed. There was no turning back. And committing in that way, that's what separates hesitant leaders from transformational ones. Exactly. The moment you stop hedging, the team senses it. Confidence starts to ripple even when the outcome is uncertain. Once the decision was fully implemented, we were no longer debating. It became real work. It wasn't smooth sailing, though, right? Not at all. Within weeks, early signs suggested the move might fail. Revenue dipped in one region. A critical partner expressed doubt.

4:30Victoria Hartman:Our team was stressed, questioning my judgment. And I won't lie, there were moments I thought, what if I made the wrong call? But this is where preparation met opportunity. Because we had anticipated risk, the team pivoted quickly, communication became clearer, accountability sharpened, and we doubled down on the areas that were working. Slowly, confidence returned, and eventually we crossed the threshold where success was visible, not just on spreadsheets, but in team morale, customer feedback, and market momentum. Looking back, what did that experience teach you? That the most meaningful moves are rarely safe, and the most rewarding decisions are often terrifying.

5:16Victoria Hartman:The fear doesn't disappear, but it becomes manageable when paired with preparation, honesty, and trust in your team. It also taught me that almost failing isn't shameful, it's necessary. Every great leader experiences doubt. Every transformative business has moments of extreme uncertainty. What matters is leaning into it and being deliberate. That's how the move that almost failed became the move that built the foundation for everything that followed. Victoria, thank you for sharing this story so openly. It's a reminder that success often comes from risk, courage, and resilience, even when the path seems impossible.

5:57Victoria Hartman:Thank you, Shane. Reflecting on it reminds me why we do this work. both the stress and the triumph. And to everyone listening, if you're facing a decision that scares you, remember, almost failing is part of every meaningful move. What matters is commitment, preparation, and clarity of purpose. Until next time.