Navigating Uncertainty in Business: GOING WITHIN & Lessons from Unlikely Sources

So often, we focus on external strategies—marketing, growth, meetings—but what if the answers to our toughest challenges lie within us? This post is part of a larger series aimed at solopreneurs, startup founders, and creatives seeking a more holistic approach to the challenges of business. This series dives into creative and philosophical insights that can provide a fresh perspective, encouraging you to look inward for clarity and purpose.

When you're forging your own path, uncertainty is inevitable. Whether you're running a business, managing a project, or building something from scratch, you will encounter moments of doubt, confusion, and frustration. But, as we’ll explore through the wisdom of six unconventional figures — Alejandro Jodorowsky, Jorge Luis Borges, Kurt Vonnegut, Hunter S. Thompson, Ursula K. Le Guin, Toni Morrison, and Khalil Gibran — these moments of uncertainty can also become opportunities for growth and transformation.

Alejandro Jodorowsky: The Power of the Unconscious

Alejandro Jodorowsky, renowned for his surreal films, teaches us to embrace uncertainty by looking to the unconscious mind for transformation. His approach to art and life challenges us to break out of rigid thinking and explore the chaos within.

1. Break free from convention.
   “Birds born in a cage think flying is an illness.”
   We often get stuck in conventional thinking, but true innovation comes when we break free from those constraints. Challenge your own boundaries and think beyond the norm.

2. Transformation comes from within.
   “The unconscious is not a bottomless pit of horrors; it is a fountain of creativity, waiting to be tapped.”
   Your best ideas may come from places you haven’t explored yet—look inward, tap into your unconscious mind, and allow the transformation to happen.

3. Let go of control.
   Jodorowsky’s work embraces chaos, reminding us that the more we try to control everything, the less creative we become. In business, sometimes you need to step back and let things evolve naturally.

Jorge Luis Borges: Complexity as Opportunity

Borges, known for his intricate and often paradoxical stories, teaches us that complexity isn’t something to be feared—it’s something to be embraced. His lessons challenge us to view each twist and turn in business as a chance to create something deeper and more meaningful.

1. Turn challenges into resources.
   “All that happens to us, including our humiliations, our misfortunes, our embarrassments, all is given to us as raw material, as clay, so that we may shape our art.”
   In business, every setback can be transformed into an opportunity. View obstacles as raw material for reinvention.

2. Embrace complexity.
   Borges teaches that life and business are rarely straightforward. The complexity you encounter in your projects can add richness—don’t shy away from it.

3. Every decision opens new doors.
   “Reality is not always probable, or likely.”
   In business, as in life, not every path is clear. Borges reminds us that each decision leads to a new opportunity, even if it wasn’t the one you originally planned for.

Kurt Vonnegut: Humanity and Humor in Business

Kurt Vonnegut’s blend of dark humour and humanity offers a grounded approach to navigating the ups and downs of business. His wisdom reminds us to stay true to ourselves and keep perspective, no matter how chaotic things become.

1. Pursue art for growth, not fame.
   “Practise any art... not to get money and fame, but to experience becoming, to find out what's inside you, to make your soul grow.”
   For solopreneurs and creatives, the process of creating is often more important than the result. Focus on growth rather than external validation.

2. Humour as a coping mechanism.
   “The arts... are a very human way of making life more bearable.”
   When business gets tough, don’t forget to laugh. Humour can be a powerful tool to stay grounded and resilient.

3. Be authentic in your goals.
   “We are what we pretend to be, so we must be careful about what we pretend to be.”
   In business, staying authentic to your mission is crucial. If you lose sight of who you are, your business will reflect that.

Hunter S. Thompson: Chaos as Fuel

Hunter S. Thompson’s chaotic yet brilliant life and work teach us that the path to success is rarely straightforward. His lessons encourage us to lean into the chaos and use it to fuel innovation.

1. Embrace the weirdness.
   “When the going gets weird, the weird turn pro.”
   Sometimes the strangest ideas are the most successful. Don’t be afraid to lean into what makes your approach unique, even if it seems unconventional.

2. Immerse yourself fully.
   Thompson’s Gonzo journalism was all about getting fully involved in the story. For business owners, this means deeply understanding your market, customers, and projects. Be present in the work you do.

3. Challenge the norms.
   Thompson constantly rebelled against authority, reminding us that innovation often comes from breaking the rules. In business, don’t be afraid to challenge industry norms.

Ursula K. Le Guin: Vision and Empathy in Leadership

Ursula K. Le Guin’s speculative fiction teaches us how to balance visionary thinking with responsibility and empathy, crucial skills for anyone in business or leadership.

1. Be a visionary, but stay grounded.
   “The creative adult is the child who survived.”
   Dream big, but stay practical. Le Guin reminds us to balance visionary thinking with the realities of the world we work in.

2. Lead with empathy.
   Le Guin’s works focus on the responsibility that comes with power. In business, leading with empathy can create lasting relationships and trust with your team and clients.

3. Adaptability is key.
   Her stories often feature characters who must adapt to new environments. For business leaders, flexibility and adaptability are essential as markets and strategies shift.

Toni Morrison: Storytelling and Resilience

Toni Morrison’s powerful narratives offer lessons on resilience and the importance of controlling your own story, both of which are crucial in business.

1. Craft your own narrative.
   “Definitions belong to the definers, not the defined.”
   Take control of your brand and your story. Don’t let others define your business for you—be proactive in shaping the narrative.

2. Resilience in the face of struggle.
   Morrison’s characters often endure immense hardship but come out stronger. In business, resilience is key to surviving setbacks and continuing to grow.

3. Create spaces for others.
   Morrison’s work is about community. As a business leader, success should be about lifting others up alongside you—whether that’s your clients, partners, or team members.

Khalil Gibran: Purpose through Service and Reflection

Khalil Gibran’s poetic insights on life, love, and work offer practical wisdom for anyone seeking deeper meaning in their business.

1. Work with love and purpose.
   “Work is love made visible.”
   Align your work with what you truly care about. Gibran reminds us that business isn’t just about profit—it’s about serving others through meaningful work.

2. Endure challenges with grace.
   “Out of suffering have emerged the strongest souls.”
   Challenges are part of every entrepreneurial journey. Gibran encourages us to face these struggles with grace, knowing they build strength and character.

3. Balance ambition with humility.
   “To be able to look back upon one's life in satisfaction, is to live twice.”
   Success is not just about external achievements, but also about finding satisfaction and fulfilment in the journey. Reflect on your progress with humility and pride.

Stepping Away from Strategy and Going Inward

The wisdom shared by these six creative minds offers a reminder that sometimes the best way forward isn’t always found in a meeting room or strategy session. As entrepreneurs, creatives and visionaries, we can become so focused on external goals and the hustle and grind of business that we forget to look inward - expect when we are in pain. But the most powerful insights often come when we step away, reflect, and connect with the whole of ourselves.

Whether it’s Jodorowsky urging us to tap into the unconscious, Vonnegut advocating for authenticity, or Gibran reminding us to find purpose through service, the lesson is clear: new answers to your business challenges might not always be found in another strategy, but in your own inner world. Take time to pause, reflect, and embrace the journey—not just the destination.