In the Trenches: A Successful Vacation

As you may recall, I planned to take a vacation this month. Why would you remember that? Because I’ve written about it twice for In the Trenches. Taking time off had me both excited and nervous, and I’m happy to report that business ran smoothly in my absence.

Back in May, I wrote that the one thing standing between me and my first real vacation in more than three years was having someone to help me book client travel. After I hired Kevin, my first travel architect, I set my sights on being ready to take a vacation in Hawaii by September. Since that time, I’ve hired another part time employee and I have my four concierges (independent contractors) as well.  I was hopeful that the team would be able to handle things when I went away.

I took a “test vacation” in June, and things went well, but that was just for a day. There were issues to address. In early August, I went to London for a few days, and I hoped that would work out. It ended up being a little rough, due to complex client problems: I found myself on the computer in the middle of the night trying to help sort things out.

Each time I stepped out, we learned better ways to deal with the issues. So when Sept. 14 came, I was ready to step on an airplane and spend a week at the beach. I felt confident, albeit clearly nervous.

I had adopted a vacation mind-set the day before I left. Although I normally divide up the workload myself, I had Kevin step in and decide who should do what, so that there would be good continuity while I was gone. That night, I set my out-of-office replies and phone messages and turned things over to my team.

My plan was to check email twice a day, once in the morning and once at night, addressing any issues that came up and generally clearing out my mailbox. I asked Kevin to text my cell phone if he needed anything urgently, so I didn’t have to worry about checking email on any kind of deadline.

Incredibly, Kevin only texted me a couple of times for minor issues. Despite a crushing amount of work that came in toward the end of the week, the team handled everything well. Sure, there were a couple of minor errors, and I suspect Kevin was seeing double by the end of the week, but the business moved forward, and I took a much-needed break. I’m so proud of my team. It makes me realize how far we’ve come in just a few short months!

About Brett Snyder

Brett is the Founder and President of Cranky Concierge air travel assistance. He also writes the consumer air travel blog, The Cranky Flier.
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