In the Trenches: Preparing for Vacation

BrettSnyder by Brett Snyder on May 2, 2012

It’s been a long time since I’ve had a real vacation. In fact, I think the last real vacation I had was my honeymoon about three years ago. Once I started Cranky Concierge, there was no way to escape for a break. Now, my goal is to make that happen in just a few short months.

I fully realized that when I started this business, I would need to be on duty at all times. But what I envisioned back when it started was that it would grow big enough to have a team that could cover for each other so that everyone could get a break once in a while. We’ve now grown to the point where I feel like that’s actually within reach, and that’s pretty exciting to me.

The biggest issue until recently has been flight bookings. I was the only one who could really do it during the day. The hiring of my first Travel Architect solves that problem. The other issue is simply a logistical one. I’m the glue that holds a lot of pieces together, and most of it is on the financial side. So I’m trying to get people ramped up on that end in order to offer some relief.

Each week, I try to train a new piece of the business with the hope that by V-Day, I will be able to step away for a week.

V-Day (that’s Vacation-Day) falls in mid-September, when I have a family trip planned to Hawaii. I would love nothing more than to be able to know that the business will keep humming along without me for that week.

As I’m sure many of my fellow small business owners will sympathize, this doesn’t mean that I’ll shut off my phone and avoid email. If anyone has questions, I will be available at all times to make sure they get answered. But I won’t be the primary task-handler on anything. I’ll just be there for support, if needed.

Let’s see how the next few months go. I’m feeling pretty confident with the way the team has been ramping up, and I can already taste the Mai Tai.


Brett Snyder is President and Chief Airline Dork of Cranky Concierge air travel assistance. Snyder previously worked for several airlines, including America West and United, before leaving to create a travel search site for Snyder did his undergrad at George Washington and earned his MBA from Stanford.