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When Challenges Become Adventures

Planning & Strategy
Thought Leadership

Recently, my brother and I set out on a short backpacking trip, hoping to find a trail that was both uncrowded and rewarding at the end. We chose our route based on a mix of advice from a backpacking guidebook and discussions on Reddit. With our gear packed and a good weather forecast, we felt prepared for the adventure ahead.

Right away, we could tell the trail wasn’t used much. Every fifty yards or so, fallen trees from a recent ice storm blocked our way. But we kept going, hoping for a great campsite at the end. We fought through thick brush and finally reached what we thought was our destination. But the campsite from the guidebook wasn’t there. There was nowhere to set up camp without a lot of extra work. As it got dark and started to rain, we decided to turn back and head for the truck, knowing that it would better prepare us for more adventures the next day.

Walking back in the dark, I wondered if our trip was a failure or a different kind of success. The obstacles reminded me of tough moments in software projects.

A big software project is a lot like a backpacking trip. You prepare by planning your route, gathering your tools, and setting clear goals. Teams mark milestones on calendars, outline deliverables, and try to anticipate obstacles. But, just like on the trail, you can't foresee every fallen tree or sudden downpour. Unexpected bugs, failing APIs, or surprises from users are the tech world’s brush and rain. The way forward is to keep adapting and pushing on.

When planning a software solution, research and discovery are essential, but so is flexibility. The real test—much like on the trail—is when something doesn't go as planned. Do you set up camp in a tough spot, carve a new path, or backtrack? Experience shows when to adapt, turning setbacks into opportunities. We once used a familiar framework but leveraged its GraphQL capabilities instead of REST to minimize the amount of effort required to build the API. This sped us to a proof of concept, but later, REST proved better at scale. Staying flexible, we refactored accordingly—just like we did when we couldn’t find a suitable campsite.

Of course, not every project means forging a brand-new path. Some follow familiar routes, much like an easy walk in the park. We’ve built dozens of content management-driven websites that highlight each client’s unique brand using proven technology. These projects move smoothly, with most steps unfolding as planned, offering a reassuring sense of predictability.

But honestly, the most rewarding projects are those built around what makes your business unique—even when that means venturing into unfamiliar territory. Even the best-planned trips hold adventure, like figuring out how to debug an issue on a server with limited access. In those moments, we rely on our experience to come up with creative solutions, much like using a headlamp to find our way on a rainy trail.

Driving home, I realized our backpacking trip was still worth framing as a real success—the detours made it a true adventure and have resulted in a lot of good stories. The same holds for software projects full of surprises: each twist is a chance to discover, adapt, and end up somewhere even better than you first set out to reach.

Have any good adventures we can go on together?

Need a fresh perspective on a tough project?

Let’s talk about how RDG can help.

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