We recently had an awesome question come up on Chad’s post, Finding Success After 30 and Beyond and 6 People Who Have:

“urockmysocks,” asked:

How does having a day job not get in the way of your travels? I’d like to have a 9-5 for the income, but then I only get 2 weeks vacation per year!


That’s actually not an uncommon question we get, and although its not always black and white, I figured I’d take a crack at giving my best answer on how I’ve managed to get 4-6 weeks off per year at my “9-5” office job.

A Quick History On Why More Time Off Is A Win-Win

When it comes to either taking extra time off from work–and possibly losing your job–versus keeping your job and continuing to pay the bills, the latter usually wins (for better or worse).

One of the greatest obstacles looming over most everyone’s desire to travel, or go after dream, is the lack of time. Unfortunately, the standard restrictions of a 9 to 5 job in the US can be the greatest time/dream-crusher of them all.

I won’t beat a dead horse by spewing out all of the articles and facts that show how having more time off from work is absolutely crucial to productivity, and more importantly, happiness.

Unfortunately, though, its seems there are not enough studies in the world to change the minds of US employers. (The average time off for a US employee doesn’t even come close to the average time off of most employees who live in other developed countries around the world.)

Required Time Off – Click Image For Details

Although its not always easy, Chad and I have successfully managed to earn extra time off from our respective jobs to take more–and lengthier–trips for Stampabout. Unless time travel was a legitimate thing, there is no way that we could film enough episodes for a season with only two weeks off from work per year.

Naturally, the best way to control your time off from work is to become your own boss. However, that is clearly a more extensive process and a topic that Chad might be able to cover a little better as he recently stepped off the hamster wheel to start his own online marketing business.

I, on the other hand, know exactly the torture “urockmysocks” is speaking about. I currently work about 35-40 hours a week as an Accounts Receivable Coordinator for a dog food and treat company (so exciting!!).

It’s your standard office job, but I’ve negotiated for the ability to take time off pretty much at will. And this isn’t the first job that has given me this extremely valuable flexibility!

So what does it take?

The 2 Must-Have Attributes

Without the following two attributes, finding more time off from work can be pretty tough.

  1. You must be able to complete the same amount of work as you would if you did NOT take more time off
    This is a no-brainer. If I’m going to do less work per year, then what is my employer’s incentive to let me take more time off?
  2. You must be really freaking good at what you do
    A teacher probably doesn’t give an ‘F’ student (or ‘D’ or ‘C’ student for that matter) more leniency or responsibility or recess. Basically, if I can prove my worth daily, I can create some leverage.

And leverage is really what it’s all about. The more my employer does not want to lose me, the more negotiating power I hold.

I’m not going to say I’m a superstar kiss-ass at work, but I’d like to believe that I take pride in the work I do.

I also never try to leave my boss or co-workers hanging. If its crunch time and I don’t have anywhere to be at the end of the day, I have no problem staying late once in awhile to make sure things are done on time.


At the end of the day, it is much easier to push the limits of what I’m allowed to negotiate (benefit-wise), if the value I provide at work is extremely hard to replace.

2 More Attributes That Definitely Won’t Hurt

Although optional, I feel there are two more attributes that definitely helped me in gaining more leverage.

  1. Work for a small company
    Larger companies need to have tighter systems in place so that everything runs like a well-oiled machine. A small and/or growing company tends to have less tiers of upper management, and therefore “bosses” have a little more flexibility in what they’re allowed to do.The closer I am to the top decision-maker in a company, the less red tape I have to fight through in order to bend the rules.
  2. Enjoy where you work
    If I enjoy where I work, its likely that I’ll be a more valuable employee. If I don’t care about my work and there’s no motivation to improve, then I’ll lose that all-important leverage.


If you’re sure you’ve got the first two must-have attributes, then both of these “optional” attributes will definitely raise your odds in successfully negotiating more time off from work.

Don’t agree with something? Have another attribute to add to the mix?

Check back next Tuesday for Part 2 of “How I’m Leveraging My Value to Get More Time Off At Work (Part 1 of 2).” I’ll try to touch on the best time to negotiate and what compromises to consider. Subscribe at the top right of this page to stay updated!

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Jake is the younger, yet taller and more dashing brother between “Jake and Chad.” He’s the voice of reason behind every one of Chad’s audacious ideas, as he puts the “calculated” in “calculated risk.” He also writes songs and makes videos for the joy of the Internet. Jake is currently redeeming the millions of airline points he’s racked up through mad travel hacking techniques and is probably on a plane somewhere.


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