My last role as a Contracting Officer was at US Special Operations Command at MacDill Air Force Base, just south of Tampa, FL. When I decided to step out of my CO role officially and start Skyway, I chose to set up the company in St. Petersburg, Florida. While some people don’t like the lack of seasons, the heat, the humidity, the water, and the fact that sun is out pretty much every single day…it’s a great fit for me.

Here’s the catch (why does there always have to be a catch?), one season in particular can be particularly maddening: Hurricane Season. It runs from June 1 to Nov 30 each year. However, the part we all really notice is the few weeks before and after Labor Day, when the risk of storms actually showing up is highest. This year, during that notorious window, Hurricane Irma ripped through the Caribbean (as a Category 5 monster), then made a bee line for Tampa Bay – and ended up ripping up the west side of Florida, including the Keys, Marco Island the large chunks of Ft. Myers and Naples.

Living in Florida is 99.5% awesome. The .5% is Hurricane Season.

Which brings us to this blog topic. In late August 2017, Hurricane Irma was plowing through the Caribbean on her way to the Southeastern US. We knew we were going to be impacted about a week ahead of time so we started making alternate plans. Five days before landfall in south Florida, it was tracking for the east side of Florida. Then, about two days before landfall, it tracked further west and was headed right for our neighborhood, literally. So we started planning and packing to evacuate. Then Irma would slow down, drift east again, then speed up, and so on. As we rushed to pack, then waited to see the track, we adjusted our plans to make sure we weren’t going to evacuate into the path of the hurricane and then end up riding out a Cat II Hurricane in a hotel room.

As I contemplated the best and worst-case scenarios, I said to one of our team members, “This feels a lot of like proposal planning.” There was a laugh, then an awkward silence as we digested just how eerily true that was. I decided after the storm was over, I’d write a blog post called “The Top 10 Ways Proposal Planning is like a Hurricane.”

In case you’re curious, the eye was within fifty miles of my house, but since we were on the west side of the storm we did not get hit as badly as we expected. We were prepared, shuttered, sandbagged, and locked up. Other than minor damage to our house, and a huge tree that fell into the street (and not into the house), we did ok. We were lucky (see Reason #9).

Here is the list finally.

  1. As dates and timelines change, we can prepare, but not really plan.
  2. We know it’s coming, but we don’t know the exact schedule or track until it happens.
  3. When it arrives, it’s too late to prepare.
  4. We have to hurry up and wait.
  5. We have to focus on what we CAN do. We need to do things in order because we can’t do everything at once.
  6. Capacity matters (the size of our evacuation vehicle is like the proposal page limits)
  7. It’s a team effort
  8. We’re usually at least a little lucky (and may not even know it)
  9. When it’s all over, it may be anticlimactic
  10. Much, but not all, of the process is repeatable

I’ll be doing a series of these to unpack each one over the coming months so we’re ready for Hurricane season next year. Incidentally, the irony is not lost on me that the heart of PROPOSAL season (mid-June to mid-Sep) is also the heart of Hurricane Season. I was actually helping two of our members with proposal projects while we were evacuated to South Carolina – where Paul Schauer and I recorded Episode 152 of the Contracting Officer Podcast, aptly titled “Excusable Delays”.