What Summiting Mount Kilimanjaro Taught Me About Overcoming Fear

Fear management in B2B professional services is the practice of mitigating psychological and operational barriers to innovation and product development. This process involves helping leaders navigate the uncertainty of shifting from bespoke services to scalable products. Mastering this skill is essential because it allows organizations to grow and protect their business while delivering honest, data-driven feedback to clients. Understanding how to apply risk management to business operations provides a framework for leaders to navigate these uncertainties effectively.

Key Takeaways
• Fear management mitigates psychological and operational barriers to innovation in B2B professional services.
• Leaders can learn how to apply risk management to business by following structured, controllable practices.
• The think big, start small approach mirrors the non-linear progress required for successful product development.
• Focusing on controllable risks prevents analysis paralysis and improves decision-making during complex business initiatives.
• Practicing gratitude and seeking expert guidance builds the resilience necessary for long-term organizational success.

I’ve also watched brave colleagues, friends and family stare down fears when the stakes are much higher - a cancer diagnosis or a sick child, for example. And I think of their ‘fearlessness’ when my smaller work-related fears can feel all-consuming.

In August, I practiced fearlessness by summiting Mount Kilimanjaro, a process that mirrors the risk management required in product innovation. On August 3, I reached the peak with my 16-year-old daughter, Kate. 

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I had been dreaming of a trip like this ever since I discovered that my daughter likes hiking almost as much as I do. Reading Michael Easter’s book The Comfort Crisis, helped me realize that a trip like this would not only give me an opportunity to get closer to my daughter but it would also take me way outside my comfort zone and help me strengthen my fearlessness muscle.

Although hiking Kilimanjaro is accessible for many fitness levels–technical climbing skills are not required, and experienced guides are required by Tanzanian law--it is NOT a zero-risk endeavor. So while I was excited, I also harbored a variety of fears. In the months leading up to the trip, I worried a lot about getting hurt or sick on the trail, especially suffering acute mountain sickness (AMS) from the high altitude. I feared that I would fail to reach the summit (fear of disappointment and embarrassment), and I feared travel snafus like missed flights and lost luggage, and of the whole plan being called off thanks to a positive COVID test. “What if…?” became something of an unhelpful mantra as our departure drew nearer.

Fortunately, I realized that I could use the same fear and risk management practices that I coach–and watch successful leaders exhibit every day–to help us climb Kilimanjaro. Those practices include:

• Think big, but start small,
• Mindfully focus on risk you can control,
• Expect less than perfect,
• Ask for help, and
• Practice gratitude

The “Think Big, Start Small” Approach to Risk Management

The phrase “pole, pole”--Swahili for slowly, slowly–is part of the Kilimanjaro culture, for good reason: the more days you spend on the mountain, and the slower you progress upwards, the better your chances of a successful summit. The best guides insist on hiking slowly–between 7 and 9 days on the trail–and ending each day at a slightly lower elevation than the group’s highest achieved point for the day (“climb high, sleep low”).

 

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In B2B productization, linear progress is often a myth, much like the non-linear ascent of a mountain. I consistently had to remind myself of what success looked like for this experience–and even though I knew I needed to come back down the trail to feel my best and reach a new elevation gain the next day, making so little perceptible progress felt a little bit like failure.

How to Mindfully Focus on Controllable Risks

Disproportionate risk assessment occurs when leaders focus on every possible negative outcome rather than the most probable ones. Focusing on everything that could go wrong can be paralyzing.

A case in point: my reading list for this trip was almost as towering as Kili itself.(I love to research!) I consumed piles of memoirs, blog posts, and videos in the months before the trip, but as time wore on, I found myself growing fearful about any and every negative outcome or scenario. Would one of us get altitude sickness and faint on the way to the summit? How would I manage a week of sleeping in a tent? What about storms and lightning strikes? Rock slides? Lost luggage? Blisters? You get the idea.

Excessive information-gathering can lead to analysis paralysis, a common hurdle in innovation consulting. As information-gathering turned into obsession, I recognized what was happening and stopped reading. I then mindfully refocused on what I felt I personally needed to do to prepare given my capabilities and Kate's capabilities. For example, we are both already fit and experienced hikers, and we were sticking to our training schedule. Our largest risk was driving each other up the wall while sharing a tent for a week.

Why Expecting Less Than Perfect Accelerates Innovation

Psychological safety and resilience involve expecting imperfections and recovering quickly from setbacks. For example, on the second day of the trek we had a steep climb and were ascending to more than 11,000 feet in elevation. In the middle of the hike Kate said she needed her inhaler, but it wasn’t packed in her day pack. Our guide had to radio ahead to our porters to bring her inhaler back to us. I felt like the worst mother–how could I be this unprepared while bringing my child into a risky environment?

Really, it was no big deal. Kate was fine. My guide reassured me, no worries, “hakuna matata.” And I had a moment where I had to confront my own expectations of what a “perfect” mother would have done in this scenario (as if she even exists!) and instead focus on what really mattered: doing what it took to safely experience the hike with my daughter, get some incredible one-on-one time with her, and to enjoy ourselves along the way.

The Importance of Seeking Expert Guidance and Investing Resources

Seeking expert guidance is a critical risk mitigation strategy for both high-altitude climbing and professional services productization. The support of expert guides is invaluable–and required by Tanzanian law to scale Kili–and there were so many times on the trail when we needed help with equipment, navigating tough terrain, adjusting our expectations, and staying focused on our goal.

I have to admit: part of my risk management/anxiety reduction strategy for Kilimanjaro was to over-buy. My REI store knows me by sight now, and I left for my trip with no fewer than seven prescriptions for in-case-of-emergency antibiotics, anti-nausea meds, and an anti-inflammatory should one of us develop edema.

I have since reframed my over-buying as a form of asking for help: seeking the advice from experienced hikers, gear experts, and my physician helped me understand what my personal needs were, and how to address them. Their input helped me understand where to invest resources for this trip–planning more nights on the trail to support acclimatization and ensuring that we had enough warm layers–and was necessary for success.

And a hard lesson from my business and product development experience hit home here: if you are not willing to invest sufficient resources into achieving your goal, don’t do it.

How Practicing Gratitude Builds Resilience

When the hike became challenging, or my fears overwhelming, feeling gratitude for the journey itself, rather than focusing on the summit, was a powerful fear-buster.

Kate is a typical 16 year old: growing up fast, trying to figure out who she is, and eager to exert her independence. The time we spent together training for the trip (four months of weekly long hikes) and hiking phone-free for 8 days in the mountains was priceless. Watching her summit Kilimanjaro is an experience for which I am incredibly grateful. I was inspired by her willingness to take on this challenge and face it fearlessly. Pausing to be grateful for this once-in-a-lifetime bonding experience with my daughter kept me focused and able to hike through discomfort and fear.

Why Fearlessness is a Trainable Skill for Business Leaders

On our flight to Tanzania, I serendipitously ran across a recent LinkedIn post by Joe Terry, CEO of Culture Partners, that spoke to the heart of this adventure on Kilimanjaro. Reflecting on how our innate human desire for comfort keeps us from growing, Joe wrote compellingly about when we deliberately step out of our comfort zone, we acclimatize our minds and bodies to handle the unexpected. Taking on challenges–which can be as small as actively listening to your co-workers or family when you are tired or as big as hiking to the top of a 19,000+ foot mountain–builds your resilience to adversity when we encounter it.

Fearlessness is a transferable skill; practicing it in personal challenges enhances a leader's ability to take calculated risks in business. When Kate and I reached the summit after a week of self-imposed adversity, I couldn’t help but feel simultaneously strong and humble: confident in my ability to do hard things and more in awe of the effort required to do them. We are indeed so much more capable than we think we are, and sometimes, we need to stretch our boundaries, face our fears, and become uncomfortable in order to see that.

If you are thinking of climbing Kilimanjaro, please reach out. I would be happy to share more lessons learned!

Frequently Asked Questions

How do I learn how to apply risk management to business effectively?

Learning how to apply risk management to business involves adopting a mindset of thinking big while starting small. Leaders should focus on controllable risks, expect imperfections during innovation, seek expert guidance, and practice gratitude to build the organizational resilience necessary for navigating uncertainty and achieving long-term strategic goals.

What is the role of fear management in professional services?

Fear management is the practice of mitigating psychological and operational barriers to innovation. It helps leaders move from bespoke services to scalable products by reframing uncertainty as a manageable process, ensuring that organizations can grow while maintaining the ability to provide honest, data-driven feedback to their clients throughout the journey.

Why is the think big, start small approach important for innovation?

The think big, start small approach is a critical risk mitigation strategy that mirrors non-linear progress. By breaking down large goals into smaller, manageable steps, leaders avoid the paralysis of perfectionism and ensure consistent progress, which is essential for successful productization and overcoming the inherent challenges of business development.

How does practicing fearlessness enhance leadership capabilities?

Practicing fearlessness builds resilience by acclimatizing a leader’s mind to handle the unexpected. When leaders deliberately step out of their comfort zones, they improve their ability to take calculated risks in business, allowing them to face adversity with confidence and humility while fostering a culture of continuous professional growth.