The Contrarian Mindset: Deviating from the Known Path

“This isn’t about abandoning your experience—it’s about shaping it to meet today’s challenges. The road ahead might look different, but the courage to step off the old one is where real growth begins.”

Change is the new constant—but it rarely feels that way when you’re the one standing at a crossroads. Many of us build careers, reputations, and lives on a set of strategies that used to work. So what happens when the world shifts, but we resist shifting with it?

In this episode of Bite Size Fridays, we explore the fear of deviating from the known path—and how the contrarian mindset helps us make brave, thoughtful pivots when the familiar starts to limit us. Through the story of Sophia, a seasoned marketing leader, you’ll see what it means to move from rigid routines to adaptive thinking—and how that shift can reignite both purpose and performance.

What You’ll Learn in This Episode

• How to spot when old strategies are holding you back, even if they once led to success
• Practical tools to reframe uncertainty as opportunity
• Why letting go of fixed outcomes opens up new pathways to progress
• How to normalize change through experimentation instead of big leaps
• The importance of leaning on others for insight, courage, and creative breakthroughs

If you’ve ever felt stuck doing “what worked before,” this episode offers practical strategies to help you lead, create, and grow with confidence in the unknown.

Contrarian Strategies from This Episode

• Reframe uncertainty as opportunity
  When things get unclear, don’t rush to fix them—pause and ask: What could I learn from this? What might be possible here that I haven’t yet considered?
• Let go of rigid outcomes
  Flexibility doesn’t mean compromising goals—it means exploring new ways to reach them. Think in Plan A, B, and C—not just one “right” answer.
• Turn obstacles into signals
  Friction isn’t failure—it’s feedback. Identify what’s not working and use it to spark change.
• Build a habit of experimentation
  Small, low-risk changes add up. Test new methods regularly to normalize innovation and reduce resistance to change.
• Lean on connection
  Surround yourself with people who think differently. Curiosity thrives in conversation, not isolation.

Perfect for You If You’re Asking:

• How do I know when to shift my approach—even if it worked in the past?
• Why does change feel so threatening, and how can I move through it with less fear?
• What does healthy risk-taking look like for a team or leader?
• How can I stay relevant without abandoning who I am or what I’ve built?

Additional Resources

This is Part 7 of the 15-part Contrarian Mindset series—each short episode helping you challenge old habits and build the mental flexibility to thrive in uncertainty.

Catch up on previous episodes:

1. Facing the Fear of Vulnerability
2. Breaking Free from Perfectionism
3. Moving Through Imposter Syndrome
4. Overcoming the Fear of Not Being Good Enough
5. Replacing Reactivity with Response
6. Embracing Change Instead of Resisting It

Chapters

• 0:16 Introduction to the Podcast
• 1:42 Practical Tips for Everyday Challenges

Transcript

Speaker: 0:08

Music. Welcome to Bite Size Fridays on It's an Inside Job, your weekly dose of resilience and perspective to carry you into the weekend. In our last series, we focused on the 12 core skills of the contrarian mindsets, tools to build real, lasting resilience. But mindset isn't just about what we grow, it's also about what we face. This series dives into the fears and mental habits that quietly hold us back, like perfectionism, imposter syndrome, or the fear of conflict and failure. Most advice teaches you how to sidestep these fears. Well, this series, it helps you meet them head on, one mindset at a time, one breakthrough at a time. Music. This week, we're going to dive into the fear of deviating from the known path. Change is the new law of life, and those who look only to the past or present are certain to miss the future. That's a quote by John F. Kennedy. There's comfort in the familiar. We build habits, systems, and routines that help us feel in control. Over time, these become our default settings, how we approach our work, lead our teams, and solve problems. And when these methods bring success, we grow even more attached to them. But what happens when this landscape shifts? When does what worked before start to fall short? This episode is about that moment when staying on the known path feels safe, but choosing it starts to hold you back. Many of us face this moment, especially when we've worked hard to earn our credibility and build our reputation. Letting go of what made us successful can feel like a step backwards, but in reality, it's often the first step forward. A contrarian mindset challenges the assumption that what's familiar is always best. It invites us to explore new methods, question old beliefs, and develop the courage to adapt even when it feels risky. This mindset doesn't mean rejecting everything we know. It means staying open to the possibility of a better way, even if it doesn't look like what we've done before. Let me give you a real example. I'd like to introduce you to Sophia. Now, Sophia is an experienced marketing leader. She had a long track record of successful campaigns and a team that respected her approach. Her strategies were clear and consistent and had served her well. But something was shifting. The market was evolving. customer expectations were changing, and new competitors were emerging with faster, more adaptive strategies. Still, Sophia stuck to her usual playbook. When we started working together, it was clear that she felt the tension. She could sense things weren't clicking the way they used to, but every time she considered trying something new, hesitation would creep in. Her thinking made sense. If this strategy brought me here, why wouldn't it take me further? That thinking works until it doesn't. Then came a turning point. Sophia had a significant product launch using the same proven formula she always relied on. But this time, the response was lukewarm. The message didn't land. The team delivered well, but the results didn't follow. This wasn't a failure in effort. It was a failure in fit. We unpacked it together. No blame, just honest reflection. And in that space, something important surfaced. Her reluctance to let go of what had worked in the past. That's when we introduced the concept of killing your darlings. It's a phrase we often use in writing or creative work. It means letting go of your favorite ideas when they no longer serve the bigger picture. Sophia's case meant questioning the assumptions and methods she relied on for years. At first, well, of course, she resisted. That's normal. Change comes with uncertainty. But slowly, she began to experiment. Small shifts, new messaging styles, fresh platforms, involving voices from outside her usual inner circle. And then things began to move. The team noticed it too. There was a new energy, more curiosity, more openness. Instead of defending old habits, they started exploring new possibilities together. Sophia didn't throw away her experience. She used it as a foundation, but now she approached each project as something alive, something to be shaped by the present, not just by the past. This is what it looks like to move from rigidity to responsiveness, to shift from repetition to relevance. It begins by facing the fear of change with intention, not bravado, but an honest willingness to grow. Putting contrarian strategies into practice. Sophia's experience highlights skills that anyone can build to become more adaptable. These aren't personality traits, they're practical, learnable skills. So I'd like to highlight now five approaches that you can start applying today. Reframe uncertainty as opportunity. Uncertainty is often seen as a problem to solve or a threat to manage, but it can also be a signal, an invitation to try something new. So what you can practice is this. When you're in the middle of something unclear or uncomfortable, pause and ask, what could I learn from this? Or what might be possible here that I haven't considered yet? Write down three positive outcomes that could come from the situation, even if they seem unlikely. Then, reflect on a time when something uncertain turned out better than expected. You know, what this does, it helps your brain to build evidence that not knowing everything right away can work in your favor. And when we tap into our past experience, well, we can learn from that past experience. As we've talked ad nauseum on this podcast, the brain is, well, it's based on the negative bias and it will tend to look at the threats and dangers. But if we invest our attention in the right way by looking at successes or achievements we've had in the past, well, that can be the arrow that points us in the right direction. Let go of rigid outcomes. Sometimes we're so attached to a specific outcome or method that we stop seeing other paths forward. Flexibility doesn't mean giving up your goals. It means staying open to multiple ways of getting there. So try this. Choose a current goal. Map out your ideal way to reach it. Then write down two alternative ways that could also succeed. You can ask yourself, if plan A doesn't go as expected, how could I adapt without losing momentum? By loosening your grip, you expand your field of vision. And again, it's killing our darlings. It's not getting fixed on one outcome because as we all know, there are variables in play that we see and that we don't see. That can shift the outcome. Being a coach and a sparring partner for so many years, I've seen how prudent it is to come up with a plan B, a plan C, even a plan D if necessary. Turn obstacles into signals. Setbacks aren't always signs that something's going wrong. Often they're cues that something needs to shift. They highlight friction and friction is where change starts. So you can practice by thinking of a recent obstacle you faced. Name it, make it specific, make it tangible. Now write down one thing it revealed. and then ask yourself, well, how can I use this to try something different? What this question does, it turns frustration into forward motion. Build a habit of experimentation. You don't need to make significant sweeping changes to grow. Small, low-risk experiments can open the door to new ideas with minimal pressure. So what you can practice is this. Set up a micro-challenge for yourself each month. It could be something small, a low-hanging fruit that is not so consequential. And then test a new method. Change a small part of your process. Tweak the pattern. Pivot just slightly and involve someone new in your workflow, for example. Afterwards, I want you to reflect and ask yourself, what did I learn? What worked better than expected? Over time, this normalizes change and makes innovation less intimidating and more productive Because as we all logically know, change is inevitable But emotionally, we're not always aligned with this logical thinking And through experimentation, making it a part of the DNA of how we approach different methodologies How we approach problems or objectives Right? Well, this can make part of our thinking, part of our contrarian thinking into understanding that change is normal and this normalizes change for us. Lean on connection. Adapting doesn't mean going it alone. Surrounding yourself with others who think differently can offer insight, support, and shared courage. So here's a practice that works for many of my clients. And that is schedule short, intentional check-ins with peers or team members. Use them to share challenges, not just updates. Create a space where curiosity is welcome and ideas can evolve together. Ask yourself, who could I learn from this week? And reach out. Collaboration often holds the keys to breakthroughs. So we've talked about five practices that I know work in different situations. But of course, this is not an exhaustive list of skills and practices. I'm sure there are ones that you use that work effectively. And so when I talked about Sophia, you know, her experience shows us that learning and growth isn't about abandoning everything we know. Far from it. It's about staying open even when we feel most inclined to close in. The fear of stepping off the known path is absolute. It shows up in all of us at some point, but it doesn't have to stop us. With the right mindset and practical tools, we can meet that fear with clarity and action. When we do, well, we create space. Not just for better work, but also for new energy, new ideas, and fresh momentum. The contrarian mindset doesn't reject experience. It builds on it with curiosity. It turns change from a threat into a tool. And most importantly, well, it helps us to keep moving forward, even when the road ahead looks different from the one we've traveled before. And sometimes the road is unclear, and it's just about one step forward each time, one brick each time to build that wall. If you're curious to know how to build a contrarian mindset for greater resilience fortitude tenacity psychological strength and a sense of well-being well you'll find the links to the other episodes in this series in the show notes so make sure you hit that subscribe button and i'll be back next week with my long-form conversational episodes on monday and the latest Bite Sides episode on Friday and have yourself a relaxing and rejuvenating weekend. Music.