The Contrarian Mindset: Mastering the Art of Uncertainty.

Uncertainty tends to make us hesitate. We overthink. We stall. We imagine worst-case scenarios. But what if uncertainty wasn’t something to avoid—but something to work with?

In this week’s episode of Bite Size Fridays, we unpack the fear of uncertainty through the lens of the contrarian mindset. I share James’s story—a seasoned financial professional whose desire for stability kept him stuck. Through coaching, reflection, and deliberate skill-building, James learned to stop resisting uncertainty and start engaging with it as a space for discovery and growth.

Here are the contrarian strategies James used to reshape his relationship with the unknown:

• Embrace uncertainty – start with low-stakes experiments to build comfort and confidence
• Let go of fixed outcomes – practice flexibility and open-mindedness toward different results
• Focus on objective reality, not emotional bias – separate facts from fear through journaling and reality-checking techniques
• Practice courage – take small, brave steps daily, even in the face of fear
• Counter rumination and overthinking – write it out, then interrupt thought loops with action

James’s transformation didn’t come from eliminating fear—it came from building a stronger relationship with it. This episode explores how you can use the same mindset to face uncertainty with resilience, flexibility, and growth.

Additional Resources:
Interested in building a contrarian mindset for resilience, fortitude, and psychological strength? Check out the other episodes in this series linked in the show notes, and subscribe to It’s an Inside Job for more insights on resilience, well-being, and personal growth.

Part 1 – Discover the Power of The Contrarian Mindset: A New Approach to Rewiring Your Brain for Resilience and Growth

Part 2 – Discover the Power of The Contrarian Mindset: A New Approach to Rewiring Your Brain for Resilience and Growth

This is Part 7 in a 15-part Contrarian Mindset series that helps you confront hidden fears and mental habits that hold you back—one mindset at a time.

🔹 Part 1 – Facing the Fear of Vulnerability
🔹 Part 2 – Breaking Free from Perfectionism
🔹 Part 3 – Moving Through Imposter Syndrome
🔹 Part 4 – Overcoming the Fear of Not Being Good Enough
🔹 Part 5 – Replacing Reactivity with Response
🔹 Part 6 – Embracing Change Instead of Resisting It
🔹 Contrarian Skills Series (Season 7) – Scroll back to January 2025 for individual deep dives on each skill

Chapters

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

Transcript

Speaker: 0:08

Music. Well, welcome to It's an Inside Job Bite Size Fridays, your weekly dose of resilience, optimism, and well-being to get you ready for the weekend. Now, each week, I'll bring you insightful tips and uplifting stories to help you navigate life's challenges and embrace a more positive mindset. And so with that said, let's slip into the stream. Music. In our last series, we explored the 12 skills of the contrarian mindset. Skills that challenge conventional thinking and help us build true resilience. But resilience isn't just about what we cultivate. It's about what we confront. That's what this series is all about. Over the next 15 Bite Size Friday episodes, we'll take a hard look at the fears and unhelpful mindsets that hold us back, the ones we all face but rarely talk about. For example, the fear of failure, the fear of vulnerability, fear of change or uncertainty, the fear of conflict, the imposter syndrome, or the weight of perfectionism. These fears don't just slow us down, they quietly shape our decisions, limit our potential, and keep us stuck in patterns that no longer serve us. Most self-help advice teaches you how to work around these fears. This series challenges you to face them head on. Because if we want real growth, deep, lasting change, we can't afford to ignore what makes us uncomfortable. Contrarian thinking isn't about being difficult for the sake of it. It's about questioning default reactions, breaking free from limiting beliefs, and seeing challenges from an angle most people overlook. So let's cut through the noise, break the patterns, and reshape the way we think, one fear at a time, one unhelpful mindset at a time. Music. Well, welcome back. This week, we are going to tackle the fear of uncertainty. You know, Pema Chodron. Pema Chodron has been quoted as saying, the only time we ever know what's really going on is when the rug is pulled out from under us and we can't find anywhere to land. We use these situations to either wake ourselves up or to put ourselves to sleep. So the contrarian mindset turns the fear of uncertainty into seeking out uncertainty as a catalyst for growth, learning, and an evolution of ourselves, both professionally and privately. So this week, as I usually kick off, I'm going to introduce you to a former client of mine. Again, I've changed the name and the industry, but this week I'd like to introduce you to James. Now, he's an experienced financial professional. He's skilled at balancing risk and reward. He appeared confident and accomplished from the outside, but our early coaching sessions quickly revealed a hidden obstacle, his fear of uncertainty. Now, this underlying fear quietly guided his choices, causing him to shy away from opportunities that required stepping into the unknown. Despite his successes, Jayme was strongly risk-averse. Each career decision revolved around predictability, stability, and avoiding potential failures. This tendency extended beyond his professional life, affecting his self-confidence and personal growth. There was a turning point. The real breakthrough for James came when we reframed his view of uncertainty and failure. We worked together to shift his perception from viewing setbacks as threats to seeing them as valuable opportunities for learning and growth. Now this change, this transition, this evolution in his mindset wasn't immediate and it was not easy. It challenged his deep-seated beliefs about success, risk, and personal worth. However, through consistent reflection and practical strategies while he began recognizing failure not as an end but as a step towards growth, a stepping stone to the other side of the river. James gradually adopted a growth mindset, acknowledging failures as necessary learning elements. Now this new mindset transformed his approach toward uncertainty. Instead of avoiding them, well James actively sought uncertain situations. Recognizing them in a space filled with potential and opportunity. Of course he started with the low-hanging fruit before diving into bigger things. One critical moment occurred during an important decision-making process at work. Faced with an uncertain and risky choice, James consciously decided to apply our coaching strategies. He proactively engaged with the uncertainty rather than retreating to safer ground. The outcome was successful, significantly boosting his confidence and demonstrating the tangible benefits of confronting uncertainty head on. Now, this shift in James' mindset wasn't confined to his career. It also positively affected his personal life, becoming more comfortable with uncertainty while it allowed James to explore new experiences and relationships. He became more genuine in interactions, open to diverse perspectives, and built stronger, deeper connections. And of course, this didn't happen overnight. It wasn't a flick of the switch. It took time. Sometimes it was two steps forward, one step back, but pulling out and looking at the bigger picture, the trend was a slow climb upwards. Now, I want to talk about some of the contrarian strategies James implemented in his development towards a more contrarian mindset when tackling with uncertainty. Embracing Uncertainty It's about viewing uncertainty, the unknown, as a space filled with opportunity rather than obstacles and danger. And a very easy way to migrate into this territory is to pick the low-hanging fruit. What I mean by that is maybe find things that you can regularly place yourself into mildly uncertain situations. That may be to speak up in meetings, maybe trying a new hobby or activity, or introducing yourself to someone new. And you can gradually increase the level of this kind of challenge as your comfort expands with dealing with the unknown. And a way to help you debrief this is maybe considering writing an uncertainty journal. You know, so like every time you've had a new experience, you can briefly know it by answering two questions. What happened and how did you feel? What did you learn about engaging with uncertainty? These kind of self-coaching questions, they help us to articulate the lessons we can learn from that. Things that we did well and things that we can improve. A couple of other questions we can ask ourselves is like, what small step into uncertainty can I take today? Maybe it's buying your food basics from a new grocery store. Maybe it's buying your gourmet coffee from a different coffee shop. Another great question is to ask yourself, how have uncertain situations in my past positively impacted my growth? Letting go of fixed and desired outcomes. This skill is about developing adaptive flexibility, to be more nimble. It's the capacity to be able to adjust smoothly when reality diverges from your expectations. So some actual exercises. One is what an exercise I call is called outcome flexibility mapping. So before any key decisions, what you want to do is take three steps. Step one is to outline your primary desired outcome. Step two is to think about two or more alternative outcomes that you could consider acceptable. And then step three is what are some specific ways you could adapt if these alternative outcomes occur? Another skill you can practice is something I call practicing non-attachment. So for example, once a week, you can select some sort of low stake activity, and then you can consciously enter it without any fixed expectations. You just sort of open to however it plays out. And what you want to do is sort of observe and reflect on how that openness influences your experience. And then you can go back to that journal and take some notes. Because a month, two months, three months from now, you'll look back and think, ah, I captured those insights. Those can really help me. So a couple of self-coaching questions you can ask yourself are, when have rigid expectations limited my growth or options in the past? What possibilities might open up if I release my attachment to a fixed outcome? Focusing on objective reality instead of emotional reality. This skill is about distinguishing factual objective reality from subjective fears and emotions during decision making. So some actionable exercise you can do is something I call reality checking technique. This is about writing down your fears and your assumptions alongside verified objective facts. and then explicitly compare these two lists to reveal any emotional biases. There's another technique that's called distancing. This is like where you imagine you're advising a good friend or a close colleague who's facing an exact situation you're facing. And it's about reflecting on how this shift in perspective changes your insider recommendations. This kind of exercise moves us from the subjective to the objective perspective. Another skill to try is what we're calling emotional fact-checking. This is about identifying emotions that are currently influencing your decisions. It's about evaluating whether these emotions match objective reality or are you exaggerating it. Because when we're faced with change or complexity or challenge that show up on our doorstep uninvited, Well, our brains tend to exaggerate those problems so they seem more scary so we will run in the other direction a lot faster. So in this case, a couple of self-coaching questions I usually assign as homework to my clients are these two. Am I responding to verified facts or am I reacting primarily out of fear? And a second question is, how would I choose differently if emotions weren't clouding my judgment? Practicing courage. Courage is the willingness to take action despite feeling fear. It's not the absence of fear itself. So there's a couple of actual exercises that I would recommend. Something that I call micro bravery challenge. It's about committing every day to one small act of courage. And that might be respectfully expressing your opinion during a meeting. It's about initiating a difficult conversation. Maybe it's volunteering for a new responsibility. Another skill you can try is something called incremental risk exposure. It's about regularly choosing tasks slightly beyond your comfort zone where you're not the master of that domain. It's about, and then afterwards, go back to the journal and then document each of these experiences. Noting how you, what was your comfort level at the time? How did you feel your confidence sort of evolved from that experience? So a couple of self-coaching questions you can ask yourself are these. What's one courageous step I could take today? What benefits did I gain the last time I took action despite my fear? Countering rumination and overthinking. It's the ability to manage repetitive and intrusive thoughts in order to maintain clarity and decisive action. So one exercise is to write down your thoughts and emotions. Whether they are silly or profound, capture those thoughts and emotions on paper. This allows you to look at them more objectively. Once you make your abstract thoughts and emotions tangible, then you can see what is actually factual, what is actually helping you, and what isn't helping you. Another one is to interrupt your thoughts with actions. This may be to prepare and immediately engage in some sort of compelling activity, something you like doing. Maybe it's a video game. Maybe it's exercise or reading or doing what in your creative hobbies. Once we begin an action, it actually turns off the rumination because our thinking is directed on one thing. Because remember, the brain can only focus on one thing at a time. It's either on the hamster wheel of rumination or it's doing something else. And so a couple of really helpful self-coaching questions are this. You can ask yourself, is this worrying helping me move forward or is it simply consuming my energy? Another great question is, what immediate concrete action can I take to break this thought cycle right now? So these are the specific skills that I helped James to incorporate in his day-to-day in order to deal more effectively and constructively with uncertainty. So when we look at James' experience, his story from a fear-driven mindset to one that embraces uncertainty, it provides a story, an example for us on the importance of resilience and adaptability in all aspects of our life. In order for us to grow, it's about stepping into the unknown and it's about facing challenges head on by implementing strategies from the contrarian playbook, such as embracing uncertainty, letting go of fixed outcomes, and practicing courage. Well, you, just like James, he could transform his fear of failure into a source of strength. You know, James' story reinforces that resilience is not about avoiding discomfort, but about using it as a catalyst for growth, for development, for an evolution of ourselves. If you look over your shoulder and you see how far you've come from grade school to where you find yourself presently, uncertainty was a constant companion. It was always there. It is always there. And as we move forward through uncertainty, we've learned, we've developed, we've grown stronger, we've gained knowledge and experience and know-how. But uncertainty is a constant road companion. And when it shows up unexpected, it can feel daunting, scary. It can trigger our anxiety, our concerns, and our worries. But if we take a moment, hit that pause button, and just sit with what our thoughts are and our emotions around that uncertainty, we find that sometimes that narrative that's running through our heads is not helping us. It's serving against us. And if we take a moment and look at uncertainty and we apply some of the cognitive techniques we use today or cognitive techniques that you use that you know works for you, it can change uncertainty. It can flip the script where we can see uncertainty as a lesson learned, a step forward into the unknown, but a step forward that will help us grow stronger and develop us, evolve our mindsets and who we are. If you're interested in any of the cognitive skills we've talked today of the contrarian mindset, you can go back into the episode feed and find a number of episodes which I've dedicated specifically to each of those cognitive techniques. So I hope you found this episode to some measure helpful. 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 the 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 Sites episode on Friday and have yourself a relaxing and rejuvenating weekend. Music.