The Small Business Vacation Checklist

Why is it so hard to go on vacation? I had this thought recently on vacation of all places. While melting into the hot tub I let go and actually let my mind drift away. As I sat, I was suddenly struck by how unremarkable my vacation circumstances were. We weren’t on a tropical island. But it felt like it. That’s because more than geography I had mentally prepared to be away and when the time came I released.

Many of us struggle with work-life balance. Honestly, there’s no perfect way to do this and I’m certainly no expert. However, this summer I’ve taken two vacations and they were both great for recharging the batteries. Here’s a quick small business vacation checklist that I put together to help you prepare for your time off. Many are applicable to larger organizations as well but small business is what I personally know first hand.

Prepare (Duh)

I know … I know. But seriously, get your vacation on the calendar and back out your schedule accordingly. Make the necessary preparations. The smaller your business, the more critical this first step is. It’s hard to kick back when you’re the only one who makes the donuts. Where should you start your preparations?

Have a Clear Plan for Pre-Launch and Re-Entry

The day before and the day after a vacation can be especially stressful. Before leaving on vacation you have so much to do you are left wondering why you even tried to get away while your return buries you in a storm that leaves you praying for an Alpine avalanche. Head these potential trainwrecks off at the pass by carefully managing your schedule for these two delicate days. If possible, try not to schedule meetings on your final day in the office. This leaves you free to tie up desk work and loose ends. When you return, maybe ease into things by treating the first half-day as a continuation of your trip while you quietly catch up on emails and calls. Speaking of email …

Set the Expectation with Email and Phone

Remember to set up those out-of-the-office email and voice messages. This is an extra step when you’re already in a rush but it does two critical things. First, it makes it real for you so you aren’t tempted to remain in work mode. Second, it diminishes how full your email gets it your absence. Again, this is a small detail but one that sets the tone.

Yeah, I Check Email on Vacation

To be clear, I am not a ‘no-work-on-vacation monk.’ It just doesn’t work for me and how you handle email on your own time is a very personal issue. And frankly, people get a little judgy on the best way to handle this. I check email once or twice a day during a vacation to delete the junk, file the CCs, and flag the key items for follow-up. If I do this five minutes a day during the trip, I can save half a day or more in aggregate when I return. I just don’t believe in absolutes that say you’re bad to your family if you check in on work every now and then on your own time.

Have a Back-Up

This isn’t practical for some but it has helped me immensely. With a clearly designated backup person in your office or on your team, you can leave someone else on the front lines as a first responder to triage and decide if you need to be engaged. Note how I said ‘clearly designated.’ You need to make sure your backup knows they are your backup and be sure to identify them and add their contact info to your out-of-the-office messages. Plus having a backup is good peace of mind. Captain Picard never could have beamed down without Number One back on the bridge.

Be Present Where You Are

A friend of mine is fond of saying this. It’s a great mantra for work-life balance but it’s especially applicable to vacation time. And though I make a point of checking a few things to ‘keep the ball in the air’ until I return, I am ultimately on vacation. The balance has shifted. My work is now ‘the other’ for the duration of my travels.

Disclosure: I did write this post poolside on vacation. You could question my commitment to the aforementioned personal time. But in reflecting on the success of my recent trips it made me realize how important it is to be prepared for vacation mentally. That’s why I wanted to capture these tips in a checklist for small businesses and share them with you. With more relaxing vacations we can not only recharge our batteries but they’ll hold their new charge even better.

What do you do to prepare for vacation? What’s on your checklist? Please take a moment and add any helpful tips that you’ve learned in the comments below.