The weather is getting warmer. Flowers are blooming. You start talking about trips and vacations.

It always seems to happen — you are talking with a good friend about an incredible travel opportunity. It might be a fun getaway with close friends or an awesome family vacation.

You get really excited about this opportunity. But then reality hits… and you start thinking about your job.

  • Can you take the time off?
  • Is it possible to be gone for the length of time of the trip?
  • Do you have enough vacation days?
  • If not, will you need to buy from the company vacation bank?
  • If you do need to by vacation days, can you afford to buy them?
  • And the big whooper – will you even be given permission to take vacation?

As a full-time employee, your schedule isn’t your own. Even in highly flexible work environments, there are still rules and expectations of employees when it comes to taking time off.


My realization of not owning my schedule


It has happened to all of us – we plan a trip and then are told we can’t take the time off. Many of us believe this is normal and the way it must be. I, myself, once believed this.

During most of my adult life I have lived several hundreds of miles away from my immediate family. As an employee, this always meant visiting family was relegated to twice a year. The year-end holidays were always one of the times I visited family.

At one job, I had transferred into a new department within my organization. Towards the year-end holidays, I informed my boss that I would be taking vacation. His reply to me was that as the newest staff member of the department I wasn’t allowed to take time off during that time.

I pleaded with him – ‘It is to go visit family. I only see them twice a year.’ He just shrugged his shoulders and wasn’t willing to change his mind.

In my previous department, while still needing to ask permission to take vacation, I had enjoyed a very flexible schedule. This change in practice surprised and startled me.

Visiting my family was important. I didn’t want an entire year to pass by before seeing them again.

Being young and naive, I reminded my boss that as a transfer I had a certain level of seniority within the organization. I also stated that it was my understanding my previous vacation schedule transferred with me. I told him I would be taking vacation at the end of the year.

I was proud I stood my ground but it cost me dearly. I made an enemy of my boss. And in the end, this cost me my job.

No one should be put in a position to choose family over work. Yet, thousands of people are forced to do it every single day.

I made a promise to myself to never have make that choice again.


You Own Your Schedule as a Digital Entrepreneur


I still live far away from my family but I see them more now than I have ever before.

One of the biggest benefits of being a digital entrepreneur is having the flexibility to run your business from almost anywhere.

Trips no longer need to be designated to specific times of the year and only when you’ve gotten permission.

You choose the when and where of your schedule. Advances in technologies allow for automation of many tasks.


What is the one trip you’ve been dreaming about taking?


We all have that one trip we dream of taking. Maybe it is hiking the Pacific Trail or taking the family to Disney World.

Now imagine not having to ask permission to take that dream trip. Imagine the freedom of choosing the exact time of year you want to take the trip and having the flexibility to decide the exact length of time you will take for the trip.

Sounds awesome, doesn’t it?

The catch is of course, you have to decide to take the path of digital entrepreneurship. There is some effort involved but the rewards far out way that effort.

In the comments below, share your thoughts on the disadvantages of being an employee or a dream trip you would want to take.

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