In 2017, I climbed Mt. Fuji in sneakers. This was not a deliberate choice to increase the challenge—it was the result of excellent research and poor judgment about what that research actually meant.

Everything I’d read suggested that Mt. Fuji was the “cakewalk of mountain climbing.” Physically, the hardest portions amounted to scrambling over some big boulders. Most of the climb was no more taxing than hiking or climbing stairs. Japanese folks in their eighties made the journey for spiritual reasons. There were huts along the way for rest, food, and water. Based on this research, I concluded that sneakers would be perfectly adequate.

The ascent was everything I’d been promised. I experienced sights I’d never imagined—cities glowing through breaks in clouds from above, walking through paths of grey nothingness where the trail disappeared into cloud cover. Each station marker brought genuine pride and accomplishment. Even the pre-dawn summit queue with 5,000 other climbers, standing in freezing darkness for hours, felt manageable. We reached the summit before sunrise, and it remains one of the most beautiful moments I’ve experienced.

Then came the descent. That’s where I learned that all the research in the world about reaching goals doesn’t prepare you for what comes after you achieve them.

When Success Becomes the Set Up for Failure

The descent from Mt. Fuji is essentially a loosely-packed dirt and gravel road on a steep decline. With proper hiking boots and trekking poles, it’s probably manageable. In flat-soled street shoes, I fell constantly, and fell hard—every three steps, for hours. I tried to take larger steps; it didn’t help. I tried to take smaller steps; that didn’t help, either. I tried cunningly to find a way to surf-slide my way down the mountainside and nearly ended up with a mouthful of dirt. As if literally rubbing salt into my wounds, without the gaiters I hadn’t brought, sand found its way into my shoes. It was without a doubt the most stupefyingly discouraging experience of my life.

As I picked myself up repeatedly, covered in dirt with scratched elbows, seasoned hikers passed me with ease. Many of them could have been my grandparents, using proper equipment and technique to descend at a steady pace while I struggled and stopped to pour tiny rocks out of my sneakers. The contrast was humbling and instructive.

This experience taught me something crucial about leadership that I’ve applied countless times since: the skills and preparation that get you to success are often different from the skills required to maintain or scale that success. The descent is frequently harder than the climb, and most people don’t prepare for it adequately.

The Post-Achievement Challenge

In business and team leadership, I’ve watched this pattern repeat consistently. The energy, skills, and resources required to achieve a goal are usually well-understood and planned for. But the challenges that come after success—maintaining market position, scaling team culture, or managing the operational complexity of growth—often catch leaders unprepared.

I’ve seen teams that executed brilliant product launches struggle with customer support and maintenance. Startups that successfully raised funding stumble when it comes to executing on their promises to investors. Engineering teams that built innovative solutions fail to create sustainable systems for maintaining and scaling those solutions. The problem isn’t lack of capability—it’s that the descent requires different preparation and different skills than the ascent. What gets you to the summit (innovation, speed, breakthrough thinking) often isn’t what gets you safely back to basecamp (consistency, processes, systematic execution).

Learning from Those Who’ve Made the Journey

Watching those experienced hikers pass me on Mt. Fuji was initially frustrating, but it became one of the most valuable parts of the experience. They had proper equipment, understood the terrain, and moved with confidence that came from experience. Most importantly, they had prepared specifically for the descent, not just the climb.

In leadership roles, I’ve learned to actively seek out people who’ve successfully navigated the “descent” phase of challenges I’m facing. Entrepreneurs who’ve managed hypergrowth. Product managers who’ve maintained market leadership over multiple years. Engineering leaders who’ve scaled teams from ten to fifty people, or CEOs who’ve scaled companies from fifty to five hundred.

These conversations can reveal patterns you may not have discovered on your own. Successful scaling requires different organizational structures than startup growth. Maintaining team culture during rapid hiring requires intentional systems that don’t emerge naturally. Sustaining innovation while managing operational complexity demands new kinds of leadership skills.

People who’ve successfully managed the descent often have hard-won wisdom about preparation and technique that isn’t captured in most “how to reach the summit” advice.

Building Skills Before You Need Them

The most effective leaders I know prepare for post-success challenges while they’re still climbing toward their initial goals. They think systematically about what will be required to maintain and scale whatever they’re building, not just achieve it.

This means building operational capabilities alongside product capabilities. Developing team management skills in individual contributors. Creating sustainable processes while you’re still in startup mode. Planning for the maintenance and evolution of systems as part of their initial implementation.

It also means recognizing that the mindset and skills that drive breakthrough achievements—risk-taking, speed, creative problem-solving—need to be balanced with different capabilities like consistency, systematic thinking, and process optimization. I’ve learned to explicitly ask: “What will success look like, and what challenges will that create?” This question reveals preparation gaps that aren’t obvious when you’re focused entirely on reaching your goals.

When You Find Yourself Unprepared

Despite best intentions, you’ll sometimes find yourself in descent mode without proper preparation—leading a team through unexpected growth, managing a product that succeeded beyond projections, or scaling systems that weren’t designed for current loads. The Mt. Fuji experience taught me how to navigate these situations effectively.

First, acknowledge the reality of your situation without wasting energy on regret about preparation gaps. You can’t change what you didn’t know or plan for previously, but you can adapt your approach based on current conditions. Take the time to solidify new goals in writing, then evaluate whether your efforts are serving them effectively.

Second, focus on learning from people who are managing similar challenges successfully. This isn’t the time for pride or trying to figure everything out independently. The hikers who passed me weren’t showing off—they had practical knowledge that could help. Conversations you have with others who came before you can save you from a lot of stumbles.

Third, lift your gaze. While the ascent phase requires day-to-day tactical thinking, the descent phase requires a strategic longer-term outlook. Implementing systems and culture that support continued success will require patience, persistence, and often a completely different pace than what got you to the summit. Expecting it to be as expedient as the climb leads to frustration and poor decision-making.

Finding Meaning in the Difficult Parts

Eventually, I reached the bottom of Mt. Fuji, exhausted and humbled but intact. At a tiny basecamp shop, I ate the most delicious bowl of ramen and the tastiest mountain-shaped sponge cake I’ll likely ever have.

Even when you’re unprepared and struggling, there’s value in the journey itself. The descent taught me lessons about preparation, humility, and persistence that I’ve applied to all sorts of challenges for years since.

Preparing for Your Next Descent

There is a Japanese proverb: “A wise man will climb Mt Fuji once; a fool will climb Mt Fuji twice.” I suspect this wisdom is based entirely on the difficulty of the descent. But in leadership, you don’t get to choose how many times you’ll face descent challenges—they’re inevitable parts of any significant journey.

The key is recognizing that achieving your goals is often just the beginning of a different kind of challenge. Success creates new problems that require different skills, different preparation, and different mindsets than what got you there initially.

Whether you’re building teams, scaling products, or managing organizational growth, prepare for the descent while you’re planning the climb. Study what happens after success. Learn from people who’ve navigated similar transitions. Build operational capabilities alongside innovative ones.

Most importantly, remember that the descent is still part of the journey, not a failure of the ascent. The challenges that come with success are signs that you’ve accomplished something meaningful. Navigate them with patience, preparation, and the understanding that getting back to basecamp safely can be an even more important achievement than reaching the summit.