Navigating Business Terrain: Lessons from Hiking in the Mountains

Hiking in the mountains isn’t just a hobby for me; it’s a passion that mirrors my passion for business building. The two activities, in my mind, are deeply interconnected. Imagine the journey of a novice hiker: it’s mostly about taking one careful step after another, with most of your focus on not tripping over the next rock or root. You spend a lot of energy trying to avoid the obvious dangers that lie ahead. Every once in a while, you stop to look around, to appreciate the journey so far and to plan your next moves. It’s a delicate balance, and a lack of attention, even for a moment, can lead to serious consequences.

I was reminded of the parallels between hiking and business this weekend while I was chatting with a new business owner, who’s also just started working with me as a coaching client. I started to think about some of the sneaky ways things can go wrong when navigating the business world. I made all these mistakes in my early days in business. Despite overcoming them eventually, they were hard lessons learned, causing setbacks and a fair share of stress. For any entrepreneur, understanding your business landscape and being mindful of these pitfalls is crucial. It can make all the difference between a successful journey to the top and an arduous climb with an unfulfilled goal. My own experiences have taught me a lot, and I’m here to share these lessons to help you sidestep the challenges that once tripped me up.

Mistake #1. Charisma vs. Competence: The Guide Who Talked a Good Talk

Picture this: you hire a mountain guide based on their charisma and the confidence they exude. It’s not until you’re halfway up the mountain that you come to the startling realization: they lack the real-world experience necessary for such an endeavor. This scenario is all too familiar in the business world. Often, leaders find themselves enchanted by a team member’s charm, neglecting to thoroughly assess their proven abilities and track record. One time I was working with a person I had hired to manage our accounts receivable and found a drawer stuffed with invoices she hadn’t processed because she didn’t know how—about $40,000 was just sitting there uncollected. Ouch. This was a stark reminder of the importance of competence over mere confidence. Just as you need a guide who intimately knows the mountain trails, your business requires team members whose skills have been tested and verified. As Ronald Reagan used to say, “Trust, but verify.”

Mistake #2. Dangerous Assumptions: The Misjudged Weather Forecast

Here’s something to consider: a hiker sees a clear morning sky and thinks it’s the perfect day for a hike, but they don’t bother to check the full weather forecast. Suddenly, they’re caught off-guard by an unexpected storm. This is a lot like what happens in business when we make assumptions without thoroughly checking the facts. In my early business days, I was confident about our success because we were known for excellent service. It seemed logical to me that this would naturally lead to our business thriving. However, reality was more complex. I learned that not everyone prioritizes service quality as their main decision factor. Influential community members and referral partners, for example, were often influenced by other aspects, such as financial incentives to send business to our competitors. This realization was a shock to me and a tough lesson. It showed me that what I value might not align with what others value. The key takeaway for entrepreneurs is to research thoroughly and test every assumption, much like a hiker should review the entire weather forecast, not just the current sky, to avoid unpleasant surprises.

Mistake #3: The Illusion of the Beaten Path – Expecting a Crowd Where None Exists

There’s a common belief among climbers that a well-marked trail always leads to a crowded summit. Entrepreneurs often fall into a similar trap, subscribing to the “build it, and they will come” philosophy. However, just as a climber might reach the top only to find it deserted, business owners can face the stark reality of no market demand for their product. I learned this lesson firsthand in a particularly tough way. Once, acting on feedback from one really good customer, I decided to launch a specialized service line in my business. The idea seemed promising, so I fully committed, investing $125,000 and bringing on two new employees to manage the project. We launched it with high hopes. But the market’s response? Utter silence. The return was dismal – barely $10,000, a fraction of our investment. In the end, we had to shut down the program. It was more than just a financial hit; it was a stark reminder of the importance of thorough market research and validation. Just as climbers scout their route before setting out, entrepreneurs must rigorously test and validate the market demand for their ideas.

Mistake #4. Feature-itis: The Overpacked Backpack

Consider an inexperienced hiker who loads their backpack with every imaginable piece of gear, believing that more equipment means better preparedness. Ironically, this extra weight only makes the journey more challenging. This is akin to what happens in business with the over-accumulation of features, often dubbed ‘feature-itis.’ In pursuit of creating the perfect product or service, there’s a tendency to add more and more features, assuming it enhances value. Yet, this often leads to an overburdened, less appealing offering.

I remember one time when I enthusiastically invested in a new technology for my business. To me and my team, the advantages seemed crystal clear. We were so convinced of its usefulness that we never paused to ask our customers if they needed or even wanted this technology before we committed a substantial amount of money to it. Had we sought their input, we might have discovered a crucial truth: what we found exciting was not necessarily a hit with our customers. The result was an expensive distraction that did little to drive our business growth.

The lesson here is to aim for a ‘light but right’ approach. In business, as in hiking, it’s not about the quantity of what you carry, but the quality and relevance. Focus on essential features that genuinely meet customer needs, rather than an overwhelming array of bells and whistles.

Mistake #5. Vanity vs. Meaningful Metrics: The Misleading Trail Markers

In hiking, just as in business, following the wrong signs can lead you off course. On the trail, it might be misleading markers, but in business, it’s often vanity metrics like social media likes. These can give a false sense of direction. In the early days of my business, I was laser-focused on growth, but I overlooked a critical question: were we growing profitably? I was keen on adding new clients, but I didn’t always stop to consider if it truly benefited our company or if the costs of delivering our promises exceeded the revenue we’d earn.

This realization led me to reevaluate our objectives and retrain our team. We shifted from seeking growth at any cost to aiming for profitable growth. It was about changing our approach to measure what truly matters, much like using a reliable compass and map to navigate a hike. This shift in focus ensures that every business step we take moves us closer to our real goals, not just the ones that look impressive on the surface.

Mistake #6. Blind Optimism: Ignoring the Signs of a Landslide

This was the hardest mistake for me to overcome, especially early on. Blind optimism in the business world is akin to a hiker overlooking warning signs of an impending landslide. It’s essential to balance optimism with a preparedness for potential risks. Just as a prudent hiker evaluates the path ahead for stability, entrepreneurs need to exercise cautious trust, waiting for concrete evidence of reliability before fully committing.

One of my favorite books in my early business journey was Jim Collins’ Good to Great, which introduces the Stockdale Paradox, named after Admiral Jim Stockdale, a Vietnam War POW. His harrowing experience led to a profound realization about enduring adversity.

Here’s a concise summary of the Stockdale Paradox:

  1. Confront the Brutal Facts: This means accepting the tough realities of your situation. It’s not about pessimism; it’s about facing the truth of the challenges and obstacles you encounter.
  2. Maintain Unwavering Faith: Despite these harsh realities, it’s crucial to hold on to the belief that you will ultimately succeed, no matter the hardships.

Stockdale spent years in captivity under harsh conditions, yet he never lost his conviction that he would survive and use his ordeal as a pivotal life experience. At the same time, he was acutely aware of the grimness of his situation.

The essence of the paradox is in balancing realism with optimism. It involves keeping a hopeful outlook towards the future while simultaneously navigating the most challenging aspects of your current circumstances. This principle is not just applicable in extreme scenarios like Stockdale’s but is also relevant in business and personal challenges. Recognizing the hard truths while fostering a firm belief in eventual success is vital for sustained achievement.

Summit Insights

Navigating through the entrepreneurial world really is a lot like planning a very, very long mountain hike. It takes a great deal of diligence, some smart preparation, and a good dose of foresight. Think of it this way: by understanding and steering clear of the common missteps I’ve shared – those I’ve stumbled over myself – you’re setting yourself up for a smoother climb in your business endeavors.

In hiking, as in business, each challenge is more than just an obstacle; it’s a chance to learn something new, to build your strength. It’s about putting together a solid plan and gathering a team that shares your vision and determination. Picture reaching the summit after all that hard work and savvy navigation. That’s what we’re aiming for in business. Keep pushing forward with grit and resilience. Trust me, the view from the top, after all those ups and downs, is going to be worth every step.

About the Author

Ron Tester is a Certified Executive Coach and Book Yourself® Solid Coach who helps service professionals and solopreneurs grow their businesses without sacrificing their personal lives. With over 20 years of entrepreneurial experience, Ron provides practical guidance on marketing, sales, operations, and work-life balance. Learn more at

Read This: Find Your Red Thread: Make Your Big Ideas Irresistible

Are you a solopreneur or small business owner searching for that elusive ingredient that will make your ideas resonate and your business thrive? Find Your Red Thread by Tamsen Webster is a transformative book that unveils the secret to turning your big ideas into irresistible propositions. Whether you’re struggling to stand out in a crowded market or seeking a more authentic connection with your audience, Find Your Red Thread could be more than just a book—it might be the blueprint you need to bring clarity, purpose, and success to your entrepreneurial journey. Read on to discover how this book can be the catalyst for your next big breakthrough.

  1. Target Audience: Anyone who has a big idea and wants to communicate that idea clearly. Because I work with solopreneurs and small business owners, I find this book particularly helpful for the kind of people I work with,  individuals running their own businesses looking for effective ways to communicate their unique value proposition and stand out in the market. I do think this book would also be enormously helpful for marketing professionals,  coaches and consultants— people who are looking for better ways to articulate their ideas and concepts to clients.
  2. Key Points and Action Steps:
    • The Concept of the Red Thread: The book introduces the ‘Red Thread’ as a metaphor for the underlying message or theme that ties together an idea, story, or business strategy. It emphasizes finding and articulating this central thread to make ideas more compelling and understandable.
    • Defining Clear Goals: Webster stresses the importance of having clear, well-defined goals. For solopreneurs, this means understanding what they want their business to achieve and what unique value they offer.
    • Problem Identification: A significant portion of the book is dedicated to identifying and articulating the problems that a business or idea is solving. This is vital for targeted marketing and for ensuring that the business is addressing genuine needs.
    • Establishing Core Truths: The author encourages finding a core truth or principle that defines your business or idea. This truth serves as a guide for both personal development and business strategies.
    • Actionable Steps for Change: The book outlines how to define the change your business promises and the actions needed to realize this change, providing a roadmap for business growth and strategy implementation.
    • Effective Communication: Webster provides guidance on creating a compelling statement or pitch that encapsulates your ‘Red Thread,’ essential for effective marketing, networking, and brand building.
  3. Themes:
    • Clarity and Purpose: The central theme is the importance of clarity and purpose in business and personal endeavors. Understanding your ‘Red Thread’ helps maintain focus and direction.
    • Storytelling in Business: The book emphasizes the power of narrative and storytelling in making business ideas resonate with the audience, an essential aspect of marketing and brand building.
    • Alignment of Personal and Business Growth: There’s a strong theme of aligning personal values with business objectives, which is particularly relevant for solopreneurs, whose personal and professional lives are often closely intertwined.
  4. Unique Insights:
    • Unique Value Proposition: Solopreneurs can use the ‘Red Thread’ concept to clarify and communicate their unique value proposition, setting them apart in a crowded market.
    • Authentic Marketing: The book’s focus on storytelling and core truths offers a more authentic approach to marketing, moving away from traditional sales pitches to narratives that genuinely connect with the audience.
    • Strategic Planning: Webster’s framework can assist in strategic planning, ensuring that business actions are aligned with the overarching goals and values, leading to more cohesive and effective growth strategies.
    • Personal and Professional Synergy: The book encourages solopreneurs to find a balance where their personal beliefs and business objectives support and enhance each other, leading to more sustainable growth and personal fulfillment.

Find Your Red Thread provides a framework that can be exceptionally beneficial for solopreneurs and small business owners in clarifying their business’s purpose, enhancing their marketing strategies, and aligning their personal growth with their business goals.

Caveat: the effectiveness of these concepts largely depends on the business owner’s ability to introspect, adapt, and apply these ideas in the context of their specific business challenges and opportunities. And that requires time. And that’s something many of us feel like we don’t have enough of.

But my question to you is, if not now, when? When are you ever going to take the time to do the important but not urgent work in your business? And how long will you be able to go on, struggling to get your message out there in the world? Take the time now to do this right and you will reap the rewards far into your better future.

About the Author

Ron Tester is a Certified Executive Coach and Book Yourself® Solid Coach who helps service professionals and solopreneurs grow their businesses without sacrificing their personal lives. With over 20 years of entrepreneurial experience, Ron provides practical guidance on marketing, sales, operations, and work-life balance. Learn more at