Lessons From the Overlook: Sometimes Work Isn’t Fun


There are times when we have to put in hard work and long hours, and it seems like there's no reward in sight. It's natural to ask yourself, "Why am I doing this?"

I recently experienced one of those times with The Overlook.

My wife, Sally, and I try to visit the cabin every four to six weeks to inspect it, bring supplies, and do routine maintenance. Unfortunately, making that visit this past September was difficult. Sally was traveling extensively and I was frantically working on the launch of my new book before we went on vacation at the end of the month.

So I took a day to drive the two hours from my home to The Overlook, did work for a couple of hours, and then drove the two hours back that same day. It was a long day—especially since I worked on the new book before I left and again when I returned home.

I must admit, I felt a small amount of resentment. Not towards anyone in particular; just the idea of visiting the cabin and not being able to have any fun bothered me!

It was a reminder that you have to have fun when you can.

The kitchen has a new mat, a couple broken glasses were replaced, and everything is ready for our next guests.


Rediscover Your Purpose

Sally and I originally purchased The Overlook because we wanted a vacation cabin, and making it a rental would help offset the costs. We envisioned it as a place where we could relax while taking in the fresh mountain air, or use it as a home base for hiking and other outdoor adventures.

Our customer service vision for The Overlook reflects both the way we feel about the cabin and then way we hope our guests will feel also:

Welcome to your mountain retreat

I thought about this as I spent the day driving to and from The Overlook.

I realized that part of my frustration came from a short visit in August, where a thunderstorm warning cancelled a hike that I had been planning for a long time. Instead of spending the day hiking in the nearby mountains, I spent that time doing chores at the cabin. Now I was heading back to do more chores without getting a chance to have some fun.

Chances are, you too had a purpose when you started your job.

Maybe the job offered an exciting career opportunity, or you were excited about the chance to develop new skills. It could be you really admired the company or its products and wanted to be part of something cool and interesting. Perhaps you just wanted to help people.

And chances are, you’ve had days like mine when it wasn’t fun.

When that happens, it helps to rediscover your purpose. In some cases, you’ll realize what you are doing has meaning and you’ll feel better about it.

One way to do that is through the Thank You Letter Challenge. This guided activity will help you envision the type of service you'd like to provide to your customers, and then invest <1 minute per day towards making that service a habit. 

So why was I slogging up to Idyllwild on a day when I felt so short on time?

Make Your Vision a Priority

It's easy to put off work if you don't understand the purpose behind it.

If I was honest with myself, I didn't need to visit The Overlook in September. The summer is our slow season, made even slower this year by a terrible fire that mostly spared the town of Idyllwild but scared away many would-be tourists. All of the chores were minor and could have been put off for a month or so.

But our vision kept nagging at me.

We already had several bookings for October, including a week-long stay. There were things I wanted to get done that I knew would make an impression on our guests, such as replacing some worn-out mats in the kitchen and bathrooms and fixing patio furniture cushions that had been torn.

I wanted The Overlook to be a welcoming retreat for our guests, just like it is for Sally and me whenever we visit.

There were some chores left for a future visit that I knew would not impact our guests. For example, we have some items that need to be donated or recycled. But they're all tucked away in storage, so guests won't see them. That can wait.

Think about your vision the next time you feel tempted to avoid work. It's okay to put something off that's not value-added. Just make sure you prioritize work that impacts your vision.

This is also a good time to ask whether what you’re doing is really adding value to your vision. Years ago, as a young nonprofit leader, I cancelled my organization’s biggest fundraiser because it didn’t help our mission. It turned out to be a liberating decision.

Remember to Have Fun

Work is so much better when we can find the joy in it.

Back to our purpose, Sally and I have a trip to The Overlook planned for later this month. I'll have fewer to do on this visit because I did so many chores in September.. Which means I am going to do that big hike I missed out on in August.

I'm really looking forward to it.

Your job has to be fun at some point. There needs to be something to look forward to that can make those frustrating days a little brighter.

Perhaps it’s a project you’re itching to work on. Maybe there’s a goal your team is trying to achieve, and you know there will be a big celebration when you reach it. Or it could be you’re just happiest when you are making an impact on your customers, and you realize you need to fix some problems to allow that to happen more often.

Whatever it is, find the fun or the whole thing will become one big, dreary chore.