How I Stopped Feeling Vacation Guilt

I can remember during my first corporate job after College, I received my first work Blackberry. My manager handed the phone to me and said, “Congratulations, you’re married to the company, now, this is your ring.” She laughed and said it was a joke but there is a little truth behind every joke.

The next month I went on a trip to Puerto Rico. I took my Blackberry and enjoyed scrolling through for any updates, until I got the dreaded message that my mailbox was full. Usually in the office, I would file emails or delete emails in order to keep the inbox clear. For whatever reason I called my co-worker/friend FROM PUERTO RICO and asked him to log into my desktop to clear the big emails. He sounded disgusted that I would even call and I vaguely remember him telling me not to call back. Typing out that story truly makes it sound ridiculous to me. I blame it to being fresh out of college and mimicking the Corporate America stereotype. Why didn’t I just turn off my phone and check it when I got back? It wasn’t my fault the company email didn’t allow for a lot of storage.

Check out the work blackberry on my hip in the Puerto Rico Photos.

As the years went on, in certain sales positions, the last day of the month is crucial. It got to the point where I would try not to schedule vacation on the last day of the month. The beginning of the year was also an important time of the year which we usually dealt with change of customers, managers and a lot. One year I was invited to All Star Weekend with a place to stay and passed on it because I didn’t want to use vacation days so early in the year. Another ridiculous story to me.

Due to the nature of Business to Business sales and the duties of my position, this would go on for years. I finally took off the last day of a month and I could be seen logged on to the corporate intranet in the sky to finish last minute contacts and orders as I headed to Vegas for Labor Day weekend. I was in technical sales and the team was dominated by males. For whatever reason I felt I needed to always be at 200% of them to stand out at work.

Racing around the Southeast to meet with customers took a toll on me. I was always on the go. It took me about three years and three promotions at work to realize if I died tomorrow, I would be replaced in a month tops. While I continued to do my job I started to plan trips on every day off. My co-workers would ask me where I was going every holiday.

As time went on my company and management started to show me just how replaceable I was by treating me like a bottom line number and interfering with my desired career path. It was more of a reminder to make time for myself and do the best I can. I felt that even after playing the game and giving 200% I was crapped on. I eventually left that company and environment after 7 years.

I write this story to say don’t be like me. Don’t get burned out and make time for vacation. It can be a short stay-cation in a nearby hotel or across the world. Buy the plane ticket, make memories with friends and family. Your older self will thank you. We shouldn’t be living just to work. We should be able to enjoy the fruits of our labor.

That is one of the reason’s I created Work Hard Travel Well, to inspire people to see the world while climbing the corporate ladder or building your own business.

If my story doesn’t motivate you, consider this; according to Project Time Off, Americans universally say that vacation days are important to them, yet 54% of workers aren’t using their hard-earned vacation time. Project: Time Off research found that workers are taking nearly a full week less of vacation than we did in 2000, resulting in a stockpile of 600 million unused vacation days.

It’s January and you probably received a new bank of vacation time. Have you planned to go anywhere to go yet? “So much to do, so little time.” While the phrase may sound like it perfectly describes our lives, research shows there actually is time.

The secret to achieving your travel goals this year, while maintaining your excellent employee status, is planning. Planning is the most important step in making vacation possible and, according to Project: Time Off, a majority (52%) of workers who set aside time each year to plan for travel take all their time off, compared to just 40 percent of non-planners. Planners also tend to take longer vacations: While three-in-four (75%) planners take a week or more at a time, non-planners take significantly fewer days — zero to three — than planners at once (42% to 18%).

The benefits of planning extend beyond days spent away from the office for rest and rejuvenation. Planners report greater happiness than non-planners with their relationships, health and well-being, company, and job. Their bosses are probably happier, too, since they’re in the loop on when you’re going to be out and can prepare accordingly.

What are you waiting for? It’s time to take back your calendar and put vacation at the top of your list of priorities. Planning for a vacation can be achieved in three simple steps:

  1. Determine how much time off you earn and identify the vacation policies at your workplace.
  2. Get to dreaming! How do you want to spend your time off this year?
  3. Plan out your days with Project: Time Off’s vacation planning tool and share with your manager, your colleagues, spouse — everyone!

This year, don’t let your vacation days be part of a statistic. Put the fear of missing out behind you and turn your bucket list into a to-do list by starting to plan now.

Need some ideas? Check out these Top Destination and Event Work Hard Travel Well Guides!

A Guide to Havana, Cuba for Americans

Detroit Weekend Guide

New Orleans Weekend Guide

Essence Festival Guide

Epcot International Food and Wine Festival Review

Read more about the importance of planning at

Sign up to join our mailing list and receive access to the top travel planning tools and discounts!

First Name

Last Name

Email Address



( mm / dd )

Powered by MailChimp

A quick video on tips for planning a tip!

Like It? Pin It!




Creator of

Love podcasts or audiobooks? Learn on the go with our new app.

Recommended from Medium

Hiring Employees: Pursue Greatness, Damn the Budget

The 3 Biggest Reasons Why Remote Working Won’t Go Away

The Transformational Story of a Butterfly

Will there be an end to the meetings at work?

Highrise is back with Basecamp

6 steps to get your first job as a software developer.

From 135000 colleagues to 25, a daunting prospect — but you never find out unless you try.

My Farewell Note On The Last Day Of Work

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store
Kim H.

Kim H.

Creator of

More from Medium

How to Turn Negative Feedback Into Positive Results

3 Inevitable Obstacles to Success You Must Handle Wisely.

How to work multiple jobs legally

Make money, save time, and more with BSP workshops