Oct 02


Do the people in your life stress you out when they bring up the word “vacation”? If yes, then welcome to the club my friend, here’s a jacket and a cigar, have a seat. For those of you whose idea of a vacation is to squeeze in as many activities as possible within an agenda, let me explain to you why many of us “workaholics” opt out of your plans if possible.

Some (not all) of us are so pressured by our jobs that time away becomes time punished due to the backlash that occurs on our return. For the outsider who isn’t in a position like this privilege makes them say “you need to get away! You work too much.” This makes a lot of sense when you’re on the outside look in but it will not compute in the mind of the painfully ambitious.

I want you to think about the most affluent people you know, the ones who got there through blood, sweat and tears. How often do they vacation? I’m not talking about Terry the young lady that has a good job, I’m talking about Lacy, the girl with a job, a business, and investment options. Ponder this for a second.

People like Lacy can relax, they probably love to relax, but when it comes to vacationing they want to actually relax. Relaxing for someone who works all of the time is not running about, trying to catch up with every alumnus from college, childhood friend and family within an area during the small amount of time that they’re visiting. What they call relaxing is the picture accompanying this article, but there’s more…

In order for a workaholic to truly relax, there needs to be coverage of the business, absolutely no plans pending, and people that are willing to understand this. Many single men and women will opt to do a Staycation (staying at home or within one’s town) in order to get chores done, watch some movies, and wind all the way down.  Others have an aversion to this but for the hustler it’s 100% understandable.

Do you know why your vacation planning is not met with much enthusiasm from the busy woman or man in your life?

What You Propose Is Not Really A Vacation To Them

One of the biggest obstacles I have found in vacationing is that the person planning wants to run about, do a ton of things, and mark them off of a checklist. This does not translate to vacation for me; as much as I work and deal with a nasty commute 5 days a week, the thought of pushing through crowds, meeting deadlines, and hearing someone freak out when we’re cutting it close sounds scarily familiar to a job.

Believe it or not they might actually like what they do

In a typical beta reality, work is this sucky thing that we’re forced to do as an adult; vacations are a tiny glimpse into that other side and it is enough to keep us sane. For the hustler, a glimpse is not enough; we want to work until that other side is ours in retirement (getting out of the rat race) or… for some people–and I know this will be impossible for many to understand–work and what we do makes us feel alive, happy, and in control. For people like this a vacation becomes more of a bother than the supposed “escape to happiness” that it’s made out to be. It is the reason why many will fight you back on taking a break; it’s because they’re wired very differently from you.

Personally my best vacation seems to come with the Christmas breaks I spend at my mother’s house. It is 2 weeks of absolutely nothing that I allow myself to have every year. All I do is write articles, play pool, do martial arts, and veg out with movies and video games. It’s something that people with a job mentality would not understand – but I wouldn’t expect them to. I just wish that they’d respect it to let me have it (I hear a lot of bellyaching on my vacation).

So the next time you plan a 5-day escape to Greece and you invite your entrepreneur buddy along. I hope this article gives you a little insight into why he refused to go with you, and why your idea of relaxation is such a foreign concept to him.

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