From the Campfire to the War Room: A 59-Day Migration Challenge

After the post-merger integration of my second smaller business, I took a much-needed sabbatical—a full year to focus on home DIY projects and reflect on what I wanted next. I’d spent time as an individual contributor and a manager, and while I was good at helping teams plan and deliver, I felt my hands-on technical skills had started to lag. By this time, I had been exposed to Agile ways of working and realized that my servant leadership style naturally aligned with Agile principles.

I was in no rush to jump back into work—until an unexpected phone call changed everything.

The Call in the Wild

It was midday, during a camping trip with family and friends. We’d been settled in for several days, enjoying the great outdoors, and had planned to tear down and head home the next morning... That’s when my phone rang.

Through a series of referrals, a VP of Engineering cold-called me with an opportunity:

• Migrate their primary and disaster recovery SaaS financial solution to an entirely new infrastructure and pair of data centers

• The deadline was set in stone 🪨 already announced and committed to customers.

• The go-live date was 59 calendar days from my first official day on the job.

It was a 45-minute conversation—me, sitting under a shade tent in the near 100-degree summer heat, listening to the scope. As I heard the details, my hindbrain kicked into gear—no hesitation, no fear.

I wanted in.

The Paper Towel Plan

By the time the call ended, I had already started outlining key questions and risks:

✅ Client Communication – Had customers been informed properly? What had they been told?

✅ Infrastructure Readiness – Was all required hardware and infrastructure at least on-site?

✅ Platform Change Risks – This was more than just a migration—a major platform upgrade was happening simultaneously.

✅ Testing Status – Where were we with configuration, testing, bug count, and severity?

This last one—combining a migration with a major platform change—was the biggest red flag I saw.

I needed to get to the East Coast ASAP to dive in. So instead of waiting until morning, we broke camp immediately. As we tore down, packed up, and loaded the vehicles, my hindbrain kept working. By the time we were heading home, I had 95% of a plan sketched out on a bunch of paper towels.

Hitting the Ground Running

I landed on-site and quickly realized that 85-90% of my paper towel plan held up. But there was one major adjustment; a large financial client (and partial owner of the platform) had strict change management processes that needed to be integrated into our plan.

Despite my "left Coast" home location, I quickly bonded with the teams, building trust and working effectively alternating every other week until migration day.

The Migration—High Stakes and Wild Turkeys

For the first several hours, everything was running ahead of schedule. Then—a major issue.

The large financial client that we needed to complete a critical step was delayed by nearly three hours. We had built our entire migration plan around tight timing, and while we had started out ahead, this delay threatened to push us past our scheduled downtime window.

I started weighing worst-case scenarios. Would we have to extend downtime? Would we have to roll back? Then, all that contingency planning and dry-run practice paid off.

The moment “Big B” (the client) finally showed up, the teams jumped into action. We worked fast and precisely, knocking out their required steps and moving forward without missing another beat.

While we were waiting something unexpected happened... We had set up a massive war room in the company’s largest conference room. This office was in a rural area, and outside our floor-to-ceiling windows, there were herds of wild turkeys wandering about.

At the height of the migration, when tension was thick and we were all waiting on “Big B,” the turkeys suddenly started attacking the glass windows.

Were they fighting their own reflections? Were they trying to help us debug? Who knows.

But for a few moments, the entire room burst into laughter. Stress levels dropped. And when we got back to work, we were re-energized. (Yes, I still have video of this!)

Aftermath & Takeaways

The migration was a success... We hit the committed date (despite the delay). Downtime was even shorter than planned, and the whole experience reinforced my belief in servant leadership—trusting your teams builds momentum.

The experience also solidified my interest in Agile. While the company itself wasn’t deeply Agile, the way we worked—the rapid response, the collaboration, the iterative approach—felt Agile.

With some time before my next role, I decided to pursue my ScrumMaster certification. As fate would have it, I ended up being trained by Jeff McKenna, one of the founding contributors to the Scrum Guide. (But that’s another story!)

Final Thought

Sometimes, the biggest career pivots start with an unexpected phone call in the middle of the woods. No office, no prep—just instinct, experience, and a plan scribbled on paper towels🧻. This one led me straight into the world of Agile, and I haven’t looked back since.