How To Fckup A Workation

You think a workation is just a vacation with some work sprinkled here & there… this is how to fckup a workation

That’s exactly why you’re messing it up!

Luckily, I can highlight for you the common mistakes people make when taking workations which ultimately give them a bad rap.

Avoid these 6 mistakes when taking a workation:

1 – You cheap-out.

 

This is especially true when booking airfare to & from your destination.

Trust me on this one:

Don’t add unnecessary risk & stress to your travel just to save a few pennies. 

Gone are the days of the 36-hour itineraries with 3-4 connections just to save $100.

Instead, use your favorite airline search platform or airline site to avoid:

• Red-eye flights.
• Super early departures & late arrivals.
• Excessively long (or short) layovers.
• Terrible airports.
• More connections than necessary.

 

2 – You pick shitty accommodations.

 

When you take a workation, your accommodations can make or break your experience since you’re  living AND working from them.

The majority of accommodations out there are geared towards people on vacations, not workations.

This means they’re usually not set up well for extended stays & everyday living with parking,  fully-equipped kitchens, multiple living areas, laundry machines, accessible to groceries, etc. They’re also not typically suitable for remote working with comfortable, private workspaces & fast, reliable internet.

That’s why it’s critical you do sufficient research & don’t just pick the cheapest or prettiest accommodations you can find. 

Instead, scour the listings for: guest reviews, pictures, the location, & if you’re not sure, confirm with the hotel or host that the internet is reliable enough for your needs.

 

3 – You plan too much.

 

When taking a workation, you’re spending a good chunk of time WORKING.

It can be tempting to plan fun activities for every non-working hour but this can backfire & reduce the fun & relaxation of the whole experience.

We did a month-long group workation with pre-arranged, full day activities every Friday, Saturday, & Sunday. This turned out to be exhausting!

In fact, one member made this comment: “Man, I can’t wait for the work week to start so I can relax a little…”

Planning & arranging too many activities ahead of time also takes away the spontaneity & serendipity of living in the present. These moments are critical to incredible & memorable travel experiences.

 

4 – You move too much.

 

Slow travel is the key here.

Keep your moves to a minimum.

Recognize that every time you move to a new accommodation, city, or country, you’re creating risk and draining your valuable time.

Think about it.

Each time you move, you’re packing & unpacking, planning & taking transportation, checking out of your old accommodations & into your new ones, figuring out the new wifi situation (& hoping it’s reliable), finding easily accessible grocery stores, restaurants, & cafes, etc. 

You should ideally aim to stay in one place for at least one month & definitely don’t move more than once every 2 weeks unless you have a lot of flexibility around your work schedule. dont do this or you will for sure learn how to fckup a workation

 

5 – You pack too much.

 

This goes without saying but traveling with too much stuff is a physical, financial, & mental drain on the experience.

Consider all the movements involved when traveling for extended periods of time:

• Schlepping your luggage on/off airplanes, trains, & buses, in/out of taxis, up/down staircases, etc.
• Excess baggage fees
• Overweight luggage fees
• Rolling heavy suitcases across town on cobblestone or uneven streets & sidewalk.

 

6 – You expect too much.

 

The last common way to screw up your workation is to expect you’re going to do everything there is to do in the local destination.

Mismanaging expectations is especially when you’re first starting out. The idea of spending a month somewhere *seems* like a long time but you’ll be surprised how much “vacationing” you’ll get to do when you’re also working while you’re there.

There’s a 4 to 1 ratio of workation to vacation time. Basically, a 4-week workation is equivalent to a 1-week vacation when it comes to doing vacation-type things.   

Set realistic expectations for how much & how little you want to do while you’re living & working remotely from your destination. 

Allow yourself enough time to stop & smell the roses.

 

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If you’re looking for the EASIEST way to mitgate the risk of taking a shitty workation:

👉 Hire a workation expert to help you plan it.

With years of experience planning solo & group workations, I can ensure you have a memorable & stress-free workation.

Shoot me an email or DM if you’re ready to travel more while:

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• Keeping your steady paycheck.
• Using minimal (or no) PTO.
• Not waiting for retirement.

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