Business Outside the Box: Running Sidkik from Japan's 750-Mile Pilgrimage Trail

It's 3 AM, and I'm wide awake again. My mind is toggling between waterproofing solutions for my tablet (because "waterproof" isn’t always as waterproof as it claims) and wondering if I've automated enough of our marketing content. In two days, I'll be taking business operations to an entirely new level - running Sidkik while walking the 750-mile Shikoku Pilgrimage in Japan, carrying our entire business operations quite literally in my backpack.

Twenty-five years ago, I thru-hiked the Appalachian Trail (AT). That journey changed everything about how I saw the world and my place in it. Now, as I prepare for another life-changing trek, I'm bringing my business along for the adventure. But running a growing company from temple steps and mountain trails requires a bit more preparation than simply loading up on onigiri and checking the weather forecast.

Let's get real about what it takes to step away from your desk for nine weeks while keeping your business not just running, but thriving. Over the past six weeks, I've been in what I call "time-bending mode" – essentially cramming three months of work into a month and a half. It turns out, preparing a business to run without you is a bit like packing for a lengthy backpacking trip: you need to be ruthlessly minimal while ensuring you have everything truly essential.

The secret? Boring is beautiful. The most reliable businesses are often the ones that run like well-oiled machines, doing the same things consistently, over and over. While I can (and do) use automation and AI to handle many tasks, there's still the very human element of creating engaging content, crafting meaningful social posts, and maintaining the authentic connection our community expects.

I've spent countless hours creating SOPs (Standard Operating Procedures) for our content creation - everything from blog posts to social media - and building comprehensive help documentation for Sidkik. This wasn't just about writing procedures; it was about creating a content ecosystem that could run smoothly in my absence.

The content batching process alone was a master class in organization. Picture this: one giant Google spreadsheet tracking everything from inspiration-centered posts to four-part blog series, from quote graphics to deeper dives into Sidkik's core beliefs. Each piece carefully themed and templated in Canva, with assists from Claude for writing and Midjourney for getting our color schemes just right. Later.com became my best friend for scheduling it all.

But the real heavy lifting came with overhauling our help documentation. Using AI, I created templates for everything from basic tooltips to advanced implementation guides. By feeding Claude screenshots of our system, we generated comprehensive guides for every aspect of our platform - from creating landing pages to setting up complex automations. Using AI has been a game-changer for content creation, but it's still me at the keyboard, shaping each piece to maintain our voice and ensure every word adds value for our community.

Just as every piece of gear in my backpack must earn its place, every piece of technology in my mobile office setup has been carefully chosen. I'm trading my trusty MacBook Pro for a Google Pixel tablet and relying heavily on my smartphone. But here's the reality that keeps me up at night: all of this tech needs to stay dry in the notoriously wet Japanese spring.

After the personal experience from the AT of finding myself unexpectedly surrounded by water - think “pillows of water” under the floor of my tent - leaking into everything I owned, I've become slightly obsessed with waterproofing. My solution? A lightweight poncho to cover everything, plus the tried-and-true combination of zip-lock bags and trusty trash bags. Because when you're running your business from a backpack in rural Japan, "water-resistant" isn't good enough – you need "monsoon-proof."

The connectivity question required careful planning. I opted for a 10GB eSIM plan that provides not just data but also a local phone number - crucial for making reservations at traditional inns that don't take online bookings. The voice plan allows me to use my phone as a hotspot, feeding data to my tablet when needed. If things go sideways? There's always (hopefully!) WiFi at inns and hotels as backup.

My digital toolkit is purposefully minimal but mighty: Signal for secure communication with Chad, Slack for team updates, Google Cloud for all our documents, and essential marketing apps like Meta and LinkedIn. I've even loaded up Spotify with Japanese language lessons for those long walking days. Google Maps is non-negotiable for navigation, especially in remote areas - another reason that reliable data connection was top priority.

The time zone dance will be interesting. Chad will be handling our current clients' immediate needs, while I'll be available via email and can jump on urgent issues through Signal during the overlap in our days - very early for me, very late for him. We'll be tracking key metrics like page views, engagement, and email list growth, but the beauty of good systems is that they keep working while you're sleeping (or walking).

The question I keep getting is "Why now?" The answer is both simple and complex. I'm in my early 50s, healthy, financially stable, and have a supportive partner in Chad who's there for our daughter and available for our clients daily. But more than that, I believe we shouldn't work our lives away or let logistics hold us back from our dreams.

This pilgrimage has been calling to me since my Appalachian Trail days. There's something powerful about following in the footsteps of countless others who've walked these paths before. On Shikoku, they say you never walk alone - you walk with Kobo Daishi (Kukai), the monk who established this pilgrimage route and who, they say, walks beside each pilgrim in spirit. As someone who spent months on the AT learning about resilience and transformation, the idea of walking in thought of one of Japan's most beloved Buddhist saints feels like a natural next step in my journey.

The preparation has been as much mental as physical. While the ultra marathon I ran in Moab this January helped with the physical training (there's nothing like desert running for building endurance), the real preparation has been about mindset. There's a vast difference between hiking for a few days and maintaining your body and spirit through months of continuous movement. You inevitably enter what ultra runners call "the pain cave," and the key is learning to transcend it rather than fight it.

The late-night anxiety is real – about being away from family for nine weeks, about navigating a country where I don't speak the language, about running a business from temple steps. But these fears are exactly why this journey matters. Growth happens at the edge of our comfort zone, whether in business or life.

I'm particularly excited about the sections of the trail that overlook the ocean. There's something about that intersection of mountains and sea that speaks to the soul. It reminds me of why we're doing this work in the first place - not just to build successful businesses, but to create lives rich with experiences that take our breath away.

While I've got clear business goals and metrics to hit during this journey - page views to track, engagement rates to monitor, email lists to grow - the real measures of success go deeper. This journey isn't just about maintaining our business momentum; it's about expanding what's possible in business and life.

The anticipated benefits fall into several categories:

The best ideas often come when we create space for them. By stepping away from the daily grind, we make room for innovation and creativity to flourish. And yes, I'll be documenting exactly how to run a business from a backpack while trekking 750 miles – because sometimes the best business lessons come from unexpected places.

This journey will be shared through our social media posts, detailed articles, and newsletter updates. We're particularly excited about inspiring others in our community to take risks and tackle difficult challenges - whether that's launching a new course, expanding their business, or yes, maybe even planning their own adventure.

You might not be planning to run your business from Japanese temple steps (though how cool would that be?), but the principles of creating a business that serves your life rather than consuming it apply universally. Through this preparation process, I've discovered some fundamental truths that can help any business owner create more freedom:

Most importantly, remember that running a successful business doesn't mean being chained to your desk. With thoughtful planning and the right systems, you can create space for whatever adventures call to you - whether that's a two-month pilgrimage, a weekend getaway, or simply more time with family.

As I prepare for this journey, I'm reminded that business success and personal growth aren't opposing forces – they're complementary paths leading to the same destination: a life well-lived.

I invite you to follow along on this adventure. Over the next nine weeks, I'll be sharing real, unfiltered insights about running a business from the pilgrimage path. Expect stories about tech fails, connectivity challenges, cultural mishaps, and hopefully, some wisdom gained along the way.

Because at the end of the day, isn't this what we're all working for? Not just to build successful businesses, but to create lives rich with experience, growth, and adventure. To show our children what's possible. To push our own boundaries. To discover what we're capable of achieving.

Maybe your dream isn't walking 750 miles through Japan. Maybe it's having the freedom to pick up your kids from school every day, or spending a month writing that book you've been thinking about, or finally taking that cooking class in Italy. Whatever it is, your business should help you get there, not hold you back.

Want to start building more freedom into your business? Download our free guide "25 Smart Ways to Share Your Expert Knowledge for Added Revenue" to begin creating systems that work for you, not the other way around. 

And stay tuned for updates from the pilgrimage path - where this business owner is putting her systems to the ultimate test!