How to Create a Workcation (And Get a Free Trip)

This is a guest post from Noah Kagan. He runs AppSumo.com, How to Make your first $1,000 Business course and a new, free marketing tool called SumoMe.com.

Not only does he want you to read about how to take a workcation, he wants to help you take one.

Leave a comment at the end of this post about why you need a workcation, and he’ll be buying a plane ticket to Austin and hooking up lodging for one lucky reader who gets to go down and work with the Appsumo team for a few days.

Seriously, all you have to do is leave a comment.

With that, Take it away Noah!

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A few weeks ago, I went to Thailand and ran AppSumo (a seven-figure business) from there.

In no way am I trying to brag. We’re fortunate to be in the position we are. But I want to show you how to create your own workcation — regardless of the budget.

Over the past few years, I’ve been extremely fortunate to travel + work = workcation from Costa Rica, Argentina, Maui, Nicaragua, Thailand, an SUV traveling Southwestern United States and more places.

Workcation

My buddy David who writes about “mini-lives” and Ariel in his sexy shorts while we are workcationing in Nicaragua!

Workcations are an AMAZING way to see a nice place while building your business without interruptions. If you’re like me, I enjoy my work — and the fact I can work and travel is an extreme blessing.

(As an aside: If you want help starting your own business so you can also travel, I show people via Monthly1k.com how I’ve created this lifestyle.)

Ten Steps to Creating Your Own Workcation

1) Location

I recommend staying in a place no more than 10 days. I’ve found this to be a great balance of enough time to see a place and also to get your work done without interrupting your routine. This includes trying to find a place that’s within eight hours of flying. Long distance trips make me want to stay longer since it’s such a hassle to fly that far.

The way I choose where to travel is based on places I’ve always wanted to go. Next up for me: Spain, S. Africa and possibly a beach-town in Mexico.

2) Housing

You can travel around trying to find hostels, but I’ve found it most effective to get a condo or house via AirBnB, Homeaway, Craigslist sublets / temporary, friend’s houses or VRBO. This ensures you’ll have a comfortable place, reduces distractions of a hostel and increases security in new places.

Stay put. It will be tempting to travel but you are adding more variables to potentially interfere with your trip. When I did my Thailand workcation we moved around too much so some meetings were missed and other locations had no wireless. Plus, the travel time on buses wore me out when we got to new places.

This is where we worked in Thailand:

Workcation 2

Note: Generally try to book at least three months in advance. This’ll give you something to look forward to and be enough time in advance to get a good price.

3) Wi-Fi

Before you book a place, ask to get a screenshot from speedtest.net. Trust me. In Nicaragua, we had horrible internet, so I didn’t get as much done. This sucks when you expect to be online. If you’re unsure about the Wi-Fi, expect it to suck.

Speedtest.net

4) Expectations

It’s very easy to get to a new place and just party your ass off or spend your time exploring all the tourist sites. Pre-commit to which days and activities you want to do. Also, know what specific things you want to work on while you are traveling. You are likely to accomplish 80% of what you would do if you were in your home setting.

When in Nicaragua I thought I’d get a ton of work done but without internet access, lots of alcohol and tons of activities planned, very little was accomplished.

Counter that to my more recent trip of Thailand, we had dedicated days to working, gorgeous settings which invigorated me to work and I knew the projects I wanted to accomplish and did.

5) Death List

Before you leave on your workcation, create a list of all the dependencies your business will have with you being gone or potentially being offline. Then see if you can do that work yourself or find someone to delegate that work too before you leave.

Here’s a few specific examples:

  • Management of advertising campaigns
  • Handling support tickets
  • New features on website / blog
  • Creating new partnerships for marketing

As well, I’ve found traveling helps me identify where I need to delegate better or focus on activities to keep the business growing (not just going) when I’m not around.

For AppSumo, I took a trip and realized there’d be no new products to promote if I wasn’t emailing partners to feature. That was a huge bottleneck to free-up so I hired a biz-dev Sumo to help us find products to promote in our free newsletter for entrepreneurs.

6) Time Zones

With the AppSumo team we’ve had challenges where I’m awake and they are asleep. Set your schedule with your team before you leave for when they can expect you to be online.

Many times I was up from 12-4am in Thailand when the team back in Austin wanted to talk to me. This was really inconvenient. Also, the guys weren’t sure when I’d be online. Agree to the meetings ahead of time and make it clear how many hours ahead you are.

I set up widgets on my Mac to make it easier to see time zones of people I work with.

Screenshot 2014-03-26 16.14.33

7) Block Out Work Times

I totally sucked on this in my recent SUV road trip. I scheduled meetings during the middle of the day which really interfered with an activity I wanted to do in Big Bend.

A better solution is to set blocks of time out when you are going to be doing your meetings and work. This makes it easier you can do things in your new city and get your work done.

Me working while in gorgeous Big Bend.

8) Housing

Get a nice place to work. When I’ve had a place where I had a nice view of the beach or mountain range, it was so much more enjoyable than just a wall. You may think you want to go to the beach more often and you will, but looking at that versus the same cubicle wall makes work all the more enjoyable.

Workcation

9) Activities

Schedule no more than 1 thing to see in a city each day. When I’ve tried to do more I spend the whole time sight seeing and not working. Allocate your time during the week for work so you can not feel guilty and explore on the weekends.

A recent good friend of mine went to work from France. She felt guilty for traveling and spent all her time working. Try to book tickets during the week for weekend so you have something to look forward to and it forces you to get out and have fun.

10) Find a local

When I went to Argentina I asked all my friends (via email, Facebook, Twitter, LinkedIn) who they knew in Buenos Aires. Someone introduced me to Morgan Friedman (the Jewish version) and it was a life saver.

With Facebook you can search friends that live in X country or friends of friends who live in X country. This makes it easy to find people. You can also search geographies in LinkedIn. Ask people that used to live there for referrals too.

Locals know restaurants, bars, coffee shops, where to buy things and more you won’t find on review sites. It’s also nice to have at least one other person welcoming you to the city versus if you go alone.

Screenshot 2014-03-26 16.18.46

Workcations are an amazing experience and blessing for people who are able to do them.

Traveling is a great way to learn about yourself, new food (my fav!) and see just how diverse / unique the world really is.

We’ve helped over 3,000+ people with Monthly1k.com start their own businesses. I won’t say it’s easy but it is possible.

Workcations allow you to merge doing work you really want to do, provide you a great way to pay for your travels and balance not just traveling cause you hate your job.

Instead of trying to create a passive-income business to travel the world which inevitably gets boring. I highly encourage you to start a business you really want to work on, invest at least 6-12 months in working on it and then create your first workcation.

Instead of just reading about workcations whether you work in a cubicle or run your own thing, I want to help 1 reader go on one!

For 1 person who comments about why they need a workcation, I’ll pay for their plane ticket and provide lodging in Austin, TX with the AppSumo team.

UPDATE: We’ll be taking comments until Sunday night at 11:59pm. Then we’ll announce the winner on Monday :)

Ps. Get Noah’s free marketing newsletter here.

Michael Good April 6, 2014 at 5:48 pm

I need a workcation because I know how creativity blossoms as you get farther away from home. I need a surge of creativity for the business breakthrough I’m looking for!

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Tess April 6, 2014 at 6:15 pm

Helpful stuff – thanks. I need a workcation because it’s definitely time to hit the reset button! I dream of supporting myself as a writer and wilderness/wildlife/travel photographer, both my “hobbies” for over 25 years, but I keep falling back to a 40+ hour work week job. Am currently considering an offer to work for a new vacation rentals company, which sounds alright, but am frustrated not to be *really* going after my dream. And I love where I live – Portland is pretty close to perfect – but wish I could make it into more of a home base from which I traveled multiple times a year, instead of feeling (all too often) like a cage. I need to fly!

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Sophia April 6, 2014 at 6:16 pm

I would love a workation because I launch my own virtual financial planning company last year and I’ve been working so hard that I haven’t been traveling as much as I want to. Now that my biz is up and running, I would love some time away to recharge and write more. I feel like my creative energy has been lacking but getting a chance to explore a new place always energizes me. Love to balance work and play!

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Trevor April 6, 2014 at 7:15 pm

I need a workcation because I’ve fallen into the habit of equating vacations with zero work — not exactly a productive habit for somehow trying to create a sustainable lifestyle of travel. I’ve identified which streams of income I want to build (spoiler: they’re travel-related), I know which steps must be taken and in what order, I know, I know, I know. In short, less ‘vac’ more ‘work.’ My very un-entrepreneurial environment in the oil fields of North Dakota also is not helping me achieve my goals. It’d be inspiring to learn good habits from a real live entrepreneur for a few days. See you soon in Austin, Noah? Thank you for this opportunity.

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Josh Heenan April 6, 2014 at 8:09 pm

Noah,

Great post. I could use a workcation to travel around the country and see my professional and college athletes compete. Watching them progress all of season is great, but having the opportunity to see them in action and set aside time to get some deep work accomplished.

Thanks guys!

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Josh Heenan April 6, 2014 at 8:11 pm

Noah,

Great post. I could use a workcation to travel around the country and see my professional and college athletes compete. Watching them progress all of season is great, but having the opportunity to see them in action and set aside time to get some deep work accomplished would be outstanding.

Thanks guys!

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Ben Hancock April 6, 2014 at 8:13 pm

Hey Sean and Noah -

First, I’m pumped to see you on Location 180, Noah! Like cake and ice cream, it’s a perfect fit.

Anyway, why would I love to have a workcation with AppSumo? How would I make the most of the opportunity and make it totally worth it for everyone involved? How would I come back from it as rockstar? Well, since you asked… four things:

People: We can do more together than apart. I don’t just want to work on my business – I also want to help others with theirs. I’m a big picture guy, so I could use help with some details. On the other hand, I’m big on processes and habits, so I can help someone else identify weak links in their workflow or understand their customers’ habits, for example.

Progress: getting a temporary reprieve from the demands of home life would give me more time and energy to focus on leveling up. Knowing I only have a week or so to spend on the workcation, I’d make the most of every moment.

Plans: I’d come into a workcation with an ultra-clear idea of what I want to accomplish. I’d spend the days leading up to it creating a plan for how I could best use the focused time to 10x my business. The specifics, of course, would depend upon when it happens. If it were, say, next week, I know right now that my #1 priority is finding and booking my next 5 clients, looking for product ideas from those clients’ problems, and finally setting up a website to start building a list. That way, I could eventually transform the service into a products-based business.

Productivity: Regardless of the specifics, my goal would be to come back having *created something*. Maybe a workbook or guide, perhaps a ghetto “version 0.01″ of a webapp to help my clients do X. Maybe a physical product like Neville’s “NevBox”. Having created something useful in less than a week would make it all worth it.

An AppSumo workcation (Sumocation!) would be a terrific opportunity, one that I’d take full advantage of. If I’m there, I’m there 120%.

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Jennifer Underwood April 6, 2014 at 10:20 pm

I’ve been working on building a new business, but all my time commitments at home make it difficult to get as much done as I’ve wanted to. I’m a single mom, working on a degree, and balancing a currently paying self-employment job with building this new business which could make me financially secure. A workcation would allow me to dedicate that time to only building my business, while also allowing for some much needed stress reduction.

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Lyn April 7, 2014 at 1:32 am

Want to explore ‘workation’, need to observe/understand your technical know how…Austin, I’ve heard, is the new rising star, sounds like a dream and a what a life experience. Thanks for the opportunity.

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James April 7, 2014 at 10:14 pm

I need one! I have an audiobook publishing company and would love to go to Austin – to connect in person with our newest author Charlie Hoehn. Hydro Jetpacking Included?

In a digital business, I have never actually met one of our authors in person. This is sad.
Thanks for the resources in the post Noah!
James

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Genevieve April 8, 2014 at 7:09 am

I am already building towards my workcation! I’m at the beginning, as in last week I got the pitch accepted for my blog, “The Rogue Road”, on ChicagoNow.com, and today I created my first post. Like you suggested, I’m now starting that 6-12 month build towards a real workcation and in general a location-independent lifestyle. As for why I’d love to participate in THIS workcation?? Well, I have to say, it’s a creative pool I’m dying to jump into….I can’t think of anything more motivating then spending some time throwing ideas around with this team. Personally, I have a ton of energy, even more ideas, and an infectious joie de vivre, so despite my newbie status perhaps I can bring something to the table too. What do you think boys?? Let’s do this!

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The Wallet Doctor April 8, 2014 at 11:15 am

Workcations sound ideal. Seeing new places and getting needed work done sounds awesome. It sounds like making it successful requires balancing the schedule carefully and being very aware of resources like Wifi. Thanks for the post!

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Christina April 8, 2014 at 7:59 pm

1 to explore an otherwise unknown destination
2 to meet new people and engage
3 to set up my camera and film a local person and I creating food and talking customs and food in a cultural sense. No common language necessary because food is the international language
4 to then upload and share our experience with other lovers of food and culture
5 to bring home a breadth of knowledge and skills I didn’t have before and then share them here

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Jan Herremans April 9, 2014 at 10:35 am

I need a workation because most of life has been work and little vacation !

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Gearoid Considine April 9, 2014 at 1:03 pm

Why you need a workcation, and he’ll be buying a plane ticket to Austin and hooking up lodging for one lucky reader who gets to go down and work with the Appsumo team for a few days. !! I am a Rat Race escapee needing Appsumo to save my inner light to burn brightly again on the outside

:)

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Tammra April 9, 2014 at 2:02 pm

I’m looking forward to finding out who wins the Workation and either jumping for joy and doing a happy dance or congratulating the winner.

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Ryan Kulp April 10, 2014 at 8:09 am

I need a workcation to wrap up all my freelance clients’ demands, since one of them (out of 6!) hired me full-time last week.

Double income is great, but the recent hire has squandered my time and it’s almost impossible to do all my work now.

After a workcation in Austin, helping with the Sumo team, I’ll be fully committed to my new job and finally in a stable place again.

Cheers,

Ryan

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Chris Neal April 10, 2014 at 8:10 am

Awesome article Noah. I’d love a workation to launch into starting a new career.

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Gary Gaspar April 10, 2014 at 8:14 am

Coz I want to wear my sunnies at the office and not have to deal with my co-workers’ facepalms

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Bjorn April 10, 2014 at 8:17 am

Thank you for this inspiring post Noah,

I would use a workation to work on my own business and get inspired again. I could do it from home, of course, but here I am working different jobs and on charity activites for collagues/friends who really need me to assist them and to be available, because they are so busy themselves. It would be easier to focus if I just got away.

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Alvaro April 10, 2014 at 8:17 am

I need a workation to revolutionize my creativity miles away from home, where the juices flow and your perspective allows to think outside the box

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Nicole Roland April 10, 2014 at 8:19 am

HI NOAH!

My name is Nicole Roland, and I recently started my own internet marketing agency titled Rebound Digital! Almost a year ago, I got laid off from my job as a Digital Media Coordinator with an up and coming social network in the Detroit area. After that, I applied for digital media jobs in the area until I just got fed up and decided to do my own thing. So far, its been going GREAT. However, while money is coming in, its not coming in fast enough for me to travel or even enjoy some of the basic luxuries I had when I was working for someone else. I am very motivated to work, but a lot of my motivation does come from diversity and inspiration. I love Detroit but the city is going through some trouble now and I think that I have pulled all the inspiration that I can from it. I need a work-cation so that I can venture out to a new place, home some new ideas, and finally be able to complete some of the tasks that my everyday life has sometimes prevented me from doing. This is a great opportunity and I hope you will consider me!

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Jeremia April 10, 2014 at 8:28 am

I need a workation in Austin so I can eat the best tacos with Noah, and while eating delicious carnitas tacos with guacamole and a margarita, we can share really cool stories both of us have, like business stuff and winning at hopscotch competitions.

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Clark Bailey April 10, 2014 at 9:07 am

Because I have no idea what I am doing.

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Dalton April 10, 2014 at 3:10 pm

I am currently brainstorming ways to make enough money to be able to leave the small town I’ve lived in my entire life, travel, and quit the local pizza place I work at from the back of that exact pizza place. The last thing I was thinking was in the realm of possibility was a workcation. However reading this post has sparked a desire in me to try and work towards this goal. Being picked would definitely help accomplish this goal and get me moving in a new direction. Austin has been one of the few options I’ve been considering when trying to pick a place to move to and I think I could really help the sumo team with anything from taco runs to dog massages. I work with websites and digital content so I could also get my work done. Long story short it would be awesome to be chosen and I would be forever grateful to Noah and the sumo team for what could only be an life changing experience.

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Ben April 10, 2014 at 6:40 pm

Great article!

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Jason April 11, 2014 at 4:52 am

If I was on a workcation with the Appsumo crew, I would…

a) Go on a ‘Taco Crawl’ through Austin with Chief Sumo
b) Swap Thailand/Workcation stories over some fine Scotch
c) Bring the CreativeLive sketch for Noah’s Mom (she liked it!) ;-)
d) Try to contribute meaningfully to Appsumo (with design/motion GFX/video prod skillz) while I’m there
e) Cook up some mad phad ka prao (‘Thailand Tacos’) for everyone!

`j~

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Max April 11, 2014 at 9:38 am

Because I’ve only learned how to work, not how to party.

Cheers!

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Nick Kizirnis April 11, 2014 at 3:31 pm

Thanks for the great post, Noah. I had never really considered the option of taking a workcation, but after reading your explanation, I can now tell you exactly why I want to take one.

During my free time from my 50+ hour/week gig, I’ve been working on a product that I have validated with the 1kaMonth course. The AppSumo course made me realize I could go bigger if I could build a platform to support the product and other ideas potential customers have mentioned. For me that means taking some time to interview experts in the industry, and to put the product and platform together. The getaway+focus time would be a game-changer for me.

Right now I keep plowing ahead, but progress is slow (but I love it).

Thanks!
Nick

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Aaron April 11, 2014 at 4:50 pm

I could totally use a workcation! I’m a consultant and I just finished up a big project helping launch Obamacare in my state. It has taken all the energy away from my app business, where I really haven’t had time to focus and address my customers in a proper way. I have a huge backlog of bugs, enhancements, and feature requests that really need to be prioritized, wire-framed, and developed. I would use the time in Austin to focus on my business, hangout with some awesome people, and try to learn as much as I can from them so I can make my customers even bigger fans of my iphone and andriod apps. What an amazing experience, thanks for setting this up!

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David K. Whitlock April 13, 2014 at 5:37 pm

Why would I want to take a “workcation” to Austin of all places?

Sounds like a terrible place to get work done.

I mean, days filled playing disc golf with co-eds from UT and stuffing my face at Taco Deli, who has time to work?

Plus there’s so much cool shit to do in Austin there’s no way to narrow it down to one thing to see each day. Bat’s under the Congress Ave bridge, chicken poop bingo at Ginny’s, Alamo draft house, Juan in a Million, and about a billion other places to go.

But if I had to do some work, it would be cool to finally see if my small business could be run remotely. Yeah, it’s a brick and mortar store, but I’ve applied so much of what I’ve learned over at okdork.com to our marketing that sales have grown enough for me to bring on a couple employee’s who are more than capable of not burning the place down while I’m gone.

Hmm… I think this workcation thing might actually work out.

Ok, go ahead and email that plane ticket to whitlock.davidk@gmail.com and I’ll see you in Austin.

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Pablo April 13, 2014 at 6:54 pm

I don’t really NEED a workation but I would LOVE to experience a taste of my desired lifestyle. I would like to show the Appsumo team my business progress thanks to their course and receive any feedback. Finally, meet new people and take my mind out of the daily routine.

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BA April 14, 2014 at 7:50 pm

Hey Sean,

I have two side companies that are now producing revenue, but I am struggling to find the time to scale. I work my day job until 9-7PM and then focus on MY companies until about 12AM every night.

At heart, I am an entrepreneur and just like your former self, my salary and benefits have created a comfortable, but deadly complacency within. As you have stated, financial security is an illusion regardless of the size of your paycheck. Working for somebody else can never immunize you from economic downturns and market turbulence.

I genuinely believe that a workcation will allow me to take my two companies to the next level. Within the next 6-12months, I plan to move to Portugal, reclaim my freedom and surf 5 days week while scaling my businesses.

I could be become a great success story for your org.

BA

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Siera Vaughn April 15, 2014 at 3:59 pm

I REALLY need a workcation for some overdue inspiration and to begin my next creative project and traveling to another town would be a way to start it off since it will revolve around food, art, travel, and such.

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mr. sou April 15, 2014 at 5:42 pm

Workation around South East Asia, the economy is booming and I think there is a lot of good opportunities …

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Alex April 17, 2014 at 3:29 am

Killer post. Could use a workcation to so that I can get a new perspective on business and where I’m going with it

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Shannon Lagasse April 20, 2014 at 11:56 am

Love this! A workcation makes so much sense to me, because I actually really enjoy my work .But it would be great to go on a workcation for a different perspective. I learn SO much when I travel, which leads to lots of great content and inspiration for material. It keeps me inspired to grow my biz, because I’m not stuck in a rut with the same visual surroundings day in and day out.

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Emily Utter May 7, 2014 at 9:47 pm

I LOVED this post! I’m working from Bali at the moment and currently working out all of the kinks described here. I’d love to go on another workcation so I can get even better at making it work while I travel. I’m a business coach and my aim is to help my clients achieve massive time and location freedom too– the better I get at it, they better they will get at it!

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may May 10, 2014 at 5:45 pm

I need to escape the shackles of a 9-5 soul destroying life and embrace the workcation as a new way of life.

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