Never fail twice–develop trusted systems to solve problems forever.

Reject the notion that forgetting or failing is just a part of the frenetic digital chaos in which we live. Learn how to create simple and trusted systems to solve any challenge.

Before I jump right into explaining how anyone of any skill level can easily create simple, trusted systems, to solve almost any problem, let’s take a moment to establish some common terminology.

What is a trusted system?

A trusted system is simply a planned way of doing things that can be relied upon. And doing things in a planned way just means that we paused to think about our solution rather than defaulting to the easiest method—in the moment—which is often our first choice, but is rarely the most effective in the long run.

Can be relied upon simply means that the pieces of the system can be counted on to work together to produce an expected outcome. Said another way, a foolproof solution.

The two building blocks to any trusted system (or foolproof solution) that involves humans are:

  1. Tools
  2. Habits (not just behaviors or routines)

Although every system is different, the tools and habits in our trusted systems rely upon each other to keep the system functioning normally. As I build a trusted system using the example below, this important interdependence should become very clear.

Finally, since humans are by their nature imperfect, the third and final component that must be baked into any system to ensure that it is foolproof is redundancy or a backstop. These are the pieces that keep the trusted system working when all else fails.

So have you ever forgotten an important birthday?

Assuming you have, I am going to use this shared experience as an example of a problem that we can solve by developing a trusted system. And although the problem I have chosen to tackle might seem like a relatively simple one—remembering someone’s birthday, reliably—the tools and principles used to solve this challenge with a trusted system can be applied to any problem, no matter how simple or complex.

Other problems that this particular trusted system could help us solve:

  • forgetting anniversaries
  • forgetting important tasks
  • forgetting unimportant tasks
  • forgetting anything that we would prefer to remember, without fail

Now, back to the problem at hand—the missed birthday.

Although I cannot help anyone with their guilt over missed birthdays from the past, I can help to implement a trusted system, such that, we never fail to remember an important birthday a second time. 

As we discussed, trusted systems are merely planned and reliable ways of solving problems. So as we attack this problem, our goal is simple—develop a trusted system that:

  1. Provides birthday reminders
  2. Is 100% reliable (aka foolproof)

Based on our objective above, if our system reminds us of the birthday, the system works. If the system reminds us of the birthday without fail, it’s reliable, and therefore it is now a trusted system.

Said a little bit differently, our root problem is remembering birthdays, reliably. Most, or all of us, can remember birthdays on our own quite well—sometimes. The without fail part where humans inevitably come up short, hence the need for the trusted or foolproof system.

So, with foolproof simplicity as our goal, let’s piece together our trusted system for remembering birthdays.

Earlier I explained that trusted systems require two key components: 

  1. Tools
  2. Habits (not just behaviors or routines)

In this step, the calendar will be our tool. Before we download just any random calendar app, let’s spend a hot minute considering the type of app to download.

If you already have an online work or personal calendar that you use, the app you download should be able to access that calendar’s information. If you have both a work and a personal calendar that cannot be merged (a problem that I solve in a separate post), use the calendar that is most applicable. For example, for a life-long friend’s birthday, your personal calendar would be the most appropriate calendar to use, not the work calendar.

If you do not already have a calendar in use, consider one that is bundled with a system (or email address) that you already use. For example, Google provides a great suite of free productivity tools that are integrated with Gmail—which of course, includes a calendar.

Assuming your tool (the calendar app) is all set up, let’s move on to the second key piece of this system—those habits that are necessary for this system to work in a trusted manner.

The first habit we need to cultivate is entering important birthdays into our tool, the calendar app. It is not currently in our nature to enter birthdates into our new tool, so becoming aware of this shortfall and determining a method to overcome it is important. If we’re successful cultivating this habit it should become second nature to us when someone mentions their birthday that we either write it down with the intent to capture it later, or to pause and immediately put it into our tool.

Without learning this habit the value of our new tool is never realized and our system never truly becomes a trusted one. This is an example of the interdependence of tools and habits within trusted systems. There a multitude of ways to go about creating and cultivating this habit, but that isn’t something I’m going to tackle here. However, please feel free to email me with questions.

In addition to remembering to add birthdays to our calendar, as they surface—in the moment—there are also two technical steps we need to consider for this particular example, and for this particular tool to work. Both of these steps must be completed when creating the calendar event in our calendar app.

The first technical step we must complete is to make this birthday an annually recurring event on our calendar. We do this by checking the “recurring event” dialogue box on our calendar (typical functionality for most calendars). This will automagically populate the event on our calendar from now until the end of time. This instant replication of recurring events is one of many reasons why digital calendars beat old school paper calendars, hands down, every time.

Now let’s discuss the second technical step.

The key piece of this technical step is creating automated context prompts—as BJ Fogg refers to them in his book, Tiny Habits. These automated alerts will prompt us in the future, such that, when the birthday that we added to our calendar comes due, we’ll be reminded with an alert. Most importantly, this removes our unreliable human memory from the equation.

Depending on what calendar app you decide to use, most will give you the option to set alerts (if yours doesn’t, pick another one). These alerts will remind you using a notification on your phone or by sending you an email, or both. Most calendar settings will also allow you to set default reminders. These are reminders that are automatically added, or baked into any future event, by default. By baking in alerts automagically, we are completely removing any reliance on human memory and thereby foolproofing the alert function of this tool.

Leveraging the automation capabilities of our tool is key—as these alerts (reminders and notifications) add additional foolproofing elements to our trusted system.

The second habit required for this system to work is for us to now begin doing one of two things (or both!). The first of these two options is to actually begin using our calendar. This is both the most effective and most positively life-changing habit that I can recommend—coming in neck-and-neck with the use of a task manager.

Although we have intelligently leveraged the automated alerts of our tool (the calendar), the habit of actually reviewing our calendar (regularly) will be our most reliable prompt to remind us about upcoming birthdays. The simple truth here is that if we review our calendar regularly, when important events show up, we’ll already be prepared for them and therefore, unsurprised. 

In this particular example, when we choose the habit of regularly reviewing our calendar, the alerts become our redundancy or backstop. That is, if we were to stop reviewing our calendar, the alerts would be the remaining foolproofing element of this system.

Finally, while I’m addressing the value of regular calendar use, a strategic truth worth mentioning here is that in order for our calendar to become a part of our trusted time management system we must use it regularly.

Simply put: 

  • Use your calendar and it will be accurate (and trusted).
  • Review your calendar and it will remain accurate (and trusted). 

Our alerts and reminders will work to remind us, but we will never realize the benefits of a bona fide (aka trusted) time management system without regular use and review of our calendar. 

The second and less preferable option is to rely upon our reminders. If you have ever accidentally swiped away an annoyingly timed reminder, you understand the danger of relying upon reminders. They work, but they should not be our go-to. This is also why I recommend setting more than one default reminder—because in this scenario (where we rely upon the alerts instead of reviewing our calendar) the only redundancy we have is the additional alerts beyond the first alert.

This is also why I have highlighted the importance of not becoming dismissive of reminders (aka alerts and notifications).

How do we become dismissive of notifications?

We begin to ignore notifications when they become meaningless. Notifications become meaningless when there are no negative consequences for ignoring them. This is particularly true with notifications associated with social media or similar, trivial apps that so many of us leave turned on, on our phones. When the notifications crescendo and become constant, they become meaningless.

Ultimately, when our phone is so riddled with notifications that we routinely and haphazardly dismiss them, we eventually become numb to them all. So if we choose to rely on our phone notifications we must be judicious about all the notifications that we allow to operate on our phone.

Similarly, if we aren’t able to stay on top of our inbox, email reminders become just as ineffective.

In summary, if regularly reviewing your calendar is not a viable option, carefully setting and relying on your reminders is a less-than-perfect, second option.

That’s it! The trusted system we just put in place will now ensure that we are always reminded of important birthdays and that we never forget an important birthday ever again, reliably.

To create your own trusted systems to permanently solve your own simple or complex problems, use the same formula I detailed here.

As a review, in this simple trusted system we deployed the two key building blocks inherent in any trusted system:

  1. A tool (in this case, the calendar)
  2. A habit (reviewing the calendar and/or not dismissing reminders)

We also highlighted how adding default reminders in our calendar app helped us to foolproof our tool by eliminating the possibility of human error.

Finally, we further foolproofed our system by implementing redundancy in two different ways:

  1. We created reminders to serve as a backstop, should we forget to review our calendar.
  2. We created multiple reminders to serve as a backstop, should we miss the first reminder.

Tools, habits, and redundancy.

These are all you need to put simple, trusted systems in place to help you to remember anything that is important to you, and to get things done, reliably.

I publish these cartoon tutorials once a week on Instagram under the @productivitywonk handle, on twitter as @evilsizor (#EvilTips) and on LinkedIn as myself. I then endeavor to explain some of these in greater detail here.

If there are any tutorials that you would like to see expanded upon here, please drop me an email: josh [at] and let me know!

Click the sign-up button above or here if you’re interested in updates, personal coaching, or attending my next online class.

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The #1 Rule to Reach Inbox Zero: Embrace the Archive

If you use more than one folder to manually file away all your emails, not only will you never reach inbox zero, but email will always be a challenge and your mind will never be clear.

If you’re interested in clearing your mind and your inbox, check out the video below, or simply continue reading.

Here is the executive summary (or the BLUF or tl;dr version) of the article and video that follows:

Complete or capture the action associated with an email, then move that completed email to your one and only “done” or “completed” folder.

That’s it. If you can do that, it becomes much more likely that you’ll see the bottom of your inbox.

If that sounds too simple, watch the quick 7-minute video below and/or read my explanation that follows.

Ultimately, if you use more than one folder, you will either never reach inbox zero, or you will struggle maintaining it, and your life will remain chaotic—at least as it pertains to email (which unfortunately, is a significant driver of what we do or do not accomplish personally and professionally).

Additionally, if your system is complex, you will also fail.

So where does that leave us?

It should be clear that what we as humans require to wrangle our inboxes are just two things: (1) a simple system that (2) relies on only one folder.

I have previously explained some of the basics and technical how-to of this simple, one folder concept in my post, Inbox Zero: The Key to Less Email is No Email (Step 3).

However, the benefits and the why behind this one folder system were not the focus of that previous article, but will be in this discussion.

Here’s what I’ll be explaining:

  • Using any number of email folders that exceed one is a really, really, bad idea.
  • A complete rundown of how to operate using only one folder.
  • When it comes to finding an email, the search function is guaranteed to beat the antiquated, find-it-by-scrolling-squinting-and-reading technique, every time.
  • Because this method makes it functionally impossible to overlook important emails or tasks, you will become a trusted taskmaster.
  • This technique does not involve deleting emails; only moving (or removing) them.

And here we go…

Using any number of email folders that exceed one is a really, really, bad idea.

  • Multiple folders cause decision fatigue. If the human brain has a finite capacity for making good decisions each day, then consider that filing (and finding) emails in a multiple folder environment requires the user to make a decision as to where to put (or find) an email every time a new email is completed (or needed). Multiply these micro-decisions by the total amount of emails processed in a given day and you can begin to see how simply filing (and finding) emails becomes an enormous and unnecessary brain drain. Especially given that—in my proposed single folder environment—zero decisions have to be made, ever.
  • Folders are so 1990s. Filing emails is an anachronism that, perhaps surprisingly, makes finding emails unnecessarily difficult. In the past, people filed emails in folders for two reasons: (1) that’s what you did with important electronic documents on your computer and (2) search sucked, so it was the only way. However, with the advent of Gmail, smart searching your inbox for the exact email you seek should have supplanted the folders system of the pre-Google era. If you are still holding on to this dinosaur methodology, fear not, for you are not alone. Allow me today to be the first to formally invite you, and all those like you, into the 21st century. 😃

How to operate using only one folder.

  • Follow these steps. (1) create a done or completed folder (2) open the email at the top of your inbox (LIFO) (3) complete or capture the action required with that email (4) move the email to your done or completed folder. That’s it! Rinse and repeat steps 2-4 until your inbox is empty.
  • Locate email intelligently. Use smart searches to find your emails instead of tediously, manually combing your inbox. There are just a few simple search terms (aka Boolean search “operators”) that if committed to memory, 100% obviate the need for folders. I also have a video that explains how to search your inbox hyper-effectively.

You become a taskmaster because it is functionally impossible to overlook important emails or tasks.

  • As the video above most clearly depicts, if your MO is to move only completed emails to your completed folder, the only way to miss an email… doesn’t exist.
  • This is because you are (1) eyeballing each email, (2) confirming that any and all associated actions are complete, and then (3) physically moving the email from your inbox to your completed folder, it is literally impossible to miss any emails. Ever. It therefore follows that you never miss emails, you will then never miss any tasks, requests or information sent to you over email (follow through and execution are of course, dependent on the strength of your personal organization and/or trusted systems). Finally, assuming a high task execution and follow through rate, you become a “fire and forget” employee, co-worker, boss friend, relative, or spouse. And ultimately, when any of these individuals know that they can send you a task, request, or anything of any level of importance, and that you will respond or action it, you become a highly trusted agent.

This technique does not involve deleting emails; only moving (or removing) them.

  • The completed folder is an actual place where emails remain to be retrieved in the future as required, it is not the trash.
  • When processing your inbox and your only perceived options are to delete the email or leave it in your inbox, of course it’ll never leave your inbox—archive instead!

I explain all of this in detail in the video I posted above.

Please watch the video and ask questions here or on my YouTube channel and I’ll be sure to answer!

Happy better emailing!
(you’ve been Evilsized!)

Capitalizing on Unexpected Free Time Using Your Read Later System: A Hastily Written Case Study

Read Later on Tap Today!

What is a read later system and why should you care about one?

A read later system is an app (or large suitcase) in which you store anything you want to read later, offline. It’s trusted because it is:

  1. Available and,

  2. It’s it.

That is, it’s always available because it’s on your phone, which is always on you, and it’s the only read later app you use (eliminating the familiar “in what internet repository or phone app did I put this thing?” dilemma we all encounter when we use too many apps).

Why should you care about having a read later trusted system?

You should care for two reasons:

  1. It’s part of a larger ecosystem of trusted systems (more to follow on that topic) that allow you to clear your inbox, use your brain for thinking (instead of remembering), and keep you organized.
  2. It allows you to be OK waiting in line at the DMV, offline for three hours on a plane, or otherwise very productive when you find yourself with or without internet, planned or not.

My read later system is Pocket.

My Go To

No affiliate links or paid advertising here, I just use the crap out of it, and love it. There are of course others.

How does it work?

You share web articles to it and it downloads them to your phone. Typically text-only, and readable in dark mode (easier on the eyes). You can also share pocket articles to your kindle if you want even less lightbulb screen time. Read all about it elsewhere, the purpose of this article is the use case that follows…

So the wife and I were thirty minutes from boarding a plane to Fuerteventura for some warm sunshine and epic waves last January. Unfortunately, our Huawei 6P phones were both crapping out and in dire need of replacement. Not wanting to buy a Pixel 2 XL because of the screen issues, it struck me that I might get a good deal on the original Pixel XL. All of this occurred to me as we’re sitting in the airport, about to spend the next couple of hours on a plane.

If you don’t know me, I’m a “let’s solve this problem now” kind of person. Having this thought, but not having the time to execute a full “research and execute” plan initially seemed understandably worrisome (to me at least). That is, until I remembered my trusty pal pocket, and sprang into action.

I immediately began smart searching every permutation of “Pixel XL phone reviews” I could think of:

“Pixel XL” review
“Pixel XL” review 2018
“Pixel XL” camera review
“Pixel XL” battery review

Etc. etc.

After garnering about twenty solid search results from reputable reviewers, and opening articles in the same amount of chrome browsers, I then shared each of the articles to pocket using the share function, followed of course, by closing each of the browsers (because Chrome is unfortunately, a memory hog).

Rinse and repeat for all twenty articles.

Right about this time the Europeans were getting restless and it was becoming obvious we needed to merge into the gate-waiting mob (they don’t do lines in Europe, for whatever reason), or we would be getting on last.

No problem.

I closed out my last browser, fired up pocket, and validated all twenty of the articles I’d just shared were confidently stored on the app in my phone, ready and waiting for me to pour through them, offline, with all the time in the world as we zipped through the air to our vacation destination.

Three days later I bought two refurbished Pixel XLs from a trusted Amazon vendor (for less than the price of one iPhone) and they arrived at our home in Germany a day after we got home. All thanks to the hours of research I was able to do from the “comfort” of my airline seat with absolutely no internet connection.

If you don’t have one, you need a read later trusted system (supposing you read, I guess).

Go go get one, enjoy, and thank me later.

Oh, and for those that are curious, some pics. 🙂


How to Batch Process Email and Manage Co-Worker Expectations

Which do you think is more productive?

The decision should be easy.

This will be the simplest how to you’ll read today.

I’m also not going to explain why you should be batch processing email (or batch-processing any other low-value, low-payoff tasks). If you need an explanation, see above. Or, check out either of these two articles (the second one also addresses canned responses, which are also incredibly useful and discussed in my other posts here).

If you work at an organization that, for almost no good reason, operates on the “did you get my email” or “why didn’t you respond to the email I sent 30 seconds ago” M.O., not checking email for greater than five minutes may feel like an occupational safety hazard.

It is absolutely not though. 

And when people understand that you’re not responding to their emails right away for good reason, they just might join you.

Here’s all you need to do:

  1. Determine when you’ll be checking your email (one, two, three times a day?)
  2. Create an out of office reply like the one below:


    If the email that you just sent me is urgent, please call me and let me know how I may help you (as I’m quite happy to do so). My number: 614-XXX-XXXX.

    Some background if you’re curious…

    In an effort to be more productive at work I have recently decided to batch process emails, as numerous studies have shown that productivity is severely hampered by continuously monitoring email.

    As such, I now read and respond to all emails between 3-4pm each day. If you need to reach me before or after this time period, feel free to call: 614-XXX-XXXX.


  3.  Check email only at carefully chosen intervals.

That’s it! Now get out there and stop answering email… so often.

Your boss will thank you (eventually).

How to Post Horizontal Videos to Instagram Stories (No Cropping Required)

Just a tiny micropost here to help add some information that was missing from the internet.

I was trying to find a video or tutorial that would show me how to upload horizontal videos to Instagram stories. I could not find a solution that did not require downloading apps or editing things on my computer. After watching one lengthy tutorial, I realised* this can be done very simply on your phone in a matter of seconds.

Here is how you do it:

  1. Shoot an amazing video holding your phone properly (horizontal)
  2. Open the video using Google photos
  3. Click the edit icon
  4. Rotate the video left or right 90 degrees (your choice)
  5. Save
  6. Upload to Instagram


*Apparently the voice-to-text dictation app on my phone is British.

How to Actually Relax on Your Next Vacation (and Return to an Empty Inbox)

If you’re interested four incredibly simple actions that can exponentially increase the quality of all your future vacations, read on.

Before we start however, a quick acknowledgement for those not yet aware of the importance of a relaxing and restful time away from work.

Bottom line: If you don’t disengage from work while you’re on vacation, you’re missing the point. There is a good reason that some of the smartest companies (with lauded culture) now require that you take vacation. Further, people that don’t take breaks from work can even become a liability. For crying out loud, Henry Ford started figuring all of this out almost one hundred years ago.

Anyhow, assuming we can all agree on these three basic things:

  1. Most supervisors are generally reasonable
  2. The tremendous value of an unplugged, stress-free vacation (i.e. not the one where you’re still working, but from the beach instead of a desk)
  3. Emails can be re-sent.

I will show you how simple it is to effectively disengage from work with a simple conversation, out of office message, and some personal courage.


Have a conversation with your boss before you leave. During this conversation, explain how much you’re looking forward to this time away to recharge and think on the business (instead of in it) from a relaxed vantage point. Carefully convey how not stressing about the work that you will be missing will be a major contributor to the stress-free nature of this vacation. Politely ask your boss if it’s OK for you to count on her to either (1) delegate to your co-worker (whom you have conducted a careful hand-off with) or (2) for her to handle all the minor “crises of the day” that come up while you’re away. Or, worst case, come to an agreement with your boss that if you are absolutely needed, that she will call you and not rely on email.


Use the following out of office message:

Regretfully, I did not receive the email you just sent to me, nor will I read it upon my return.

I am currently on vacation and will not be reading any emails received from 5-15 February. If your email requires action or contains important information, I respectfully request you pursue one of the following options:

  • Contact me upon my return on 16 February.
  • Contact Lukas Skarsgård at (XXX) XXX-XXXX or lukas.skarsgå
  • Forward your original email to me and include in the Cc line (how this works:

Thank you very much for your consideration and understanding as I spend this limited but important time away from work.


While on vacation, do one of three things:

  1. Pause your inbox.
  2. Turn off the email sync option on your work phone.
  3. Leave your work phone at home (but be sure to leave a personal mobile number with your boss if he expects to call you for emergencies)


This is the personal courage part I mentioned earlier.

When you return to work and you open your email inbox, do exactly the following (these steps assume that you left work with zero emails in your inbox):

  1. Carefully avoid eye contact
  2. Select all emails (Ctrl+a)
  3. Archive all emails (or move to your completed folder)

And breathe a deep, satisfying sigh of relief as the world continues to turn, just as it always has, and always will.

Finally, if what you read is 100% antithetical to your current company culture, you may need to seek employment elsewhere. Why? Because your boss won’t sneak into the cemetery and scribble, “He was a great man who diligently checked emails whilst on vacation” on your tombstone.

Do it. Do it for you. Do it for your health. Do it for your family.

Here’s to your next enjoyable vacation!

How to Avoid a Terrible Airbnb (and Pick the Perfect One) for Your Next Budget Vacation


If you still aren’t already sold on the cost saving awesomeness that are Airbnbs, before I explain how to avoid a terrible Airbnb, I’ve taken a moment to list just a few of the reasons my wife and I have made the permanent switch.

However, if you’re already sold on an Airbnb and just need the scoop on reserving the best Airbnb for your next trip, feel free to skip ahead to the enumerated steps located just a quick scroll below.


The obvious reason for booking an Airbnb instead of a standard hotel is certainly the potential for large cost savings. Depending on your source, the savings may not always be worth some of the downsides (but I disagree). It’s also important to note that although hotels generally have a few options that affect price, when searching for the right Airbnb, there are a very wide variety of options that can greatly affect the final cost of your stay. I can say this definitively from my own personal experience – having used Airbnb to save up to 50% or more while exploring Europe these last two years.

Other key benefits to picking an Airbnb:

  • Options – Pay for only the space you need (i.e. Do you need a week of luxury or just a room with a bed to crash for a night?)
  • Proximity – How close to the action do you need to be? While there aren’t always hotels close to an event or location you may be interested in, there’s generally always an Airbnb close by.
  • Concierge services – Many hosts are known for their friendliness and are more than willing to assist you navigating the city or neighborhood.


Certainly, as with any travel situation, the risks of letdowns from a bad experience always exist. Although this can usually be avoided by carefully reading user reviews, sometimes things may just go awry unexpectedly. I’ve listed some potential drawbacks that should certainly be considered before booking an Airbnb:

  • Last-minute cancellations – Airbnb hosts are humans and things happen, so last-minute cancellations are certainly a possibility (but can also be successfully avoided, please continue reading).
  • Hardware failures – Unlike hotels, there are not rooms a plenty, so if the one and only shower head breaks, you may go a day without feeling “so fresh and so clean, clean” while a technician does their thing.
  • Extra chatty hosts – Not everyone values personal interaction, feedback, or assistance in the same way.
  • Varying comfort standards – Different people are accustomed to different standards of living across the globe. In Europe, crappy beds, extremely small showers, and tiny apartments without air conditioning are absolutely a thing – even in the summer time. Hotels know better and generally cater to the lowest common denominator (i.e. needy and/or pampered westerners). This is often not true for individuals renting out some of their extra space on Airbnb.

The good news is, if you read the simple steps I’ve outlined below, you can optimize all the benefits of an Airbnb and minimize or eliminate the potential risks that I highlighted above.

Ready? Here we go…


  1. Determine your location

This one is completely up to you (google maps FTW). Immediate considerations are of course proximity to the airport or your destination, parking requirements, public transportation options, and whatever else will make your stay the most enjoyable. Using the integrated Google map provided by Airbnb makes refining your options by location very simple. Although Airbnb will not give you an exact address (for good reason), it gives you a very good idea of the location.

  1. Determine your price range

There are several ways to go about setting your own personal price limit, and to a certain extent, the market will dictate this for you. A simple rule of thumb might be to find an inexpensive hotel in the same general area using google maps (making sure to select the same dates of your stay) and setting this as your starting price ceiling, perhaps. Sometimes I adjust my price after I’ve refined all my search criteria (step 4 below) and I see what prices are populating the map, like this:

As you can see, the prices fluctuate widely based on location, but low, median, and peak prices are easy to ascertain. All you would then need to do is pick your own personal limit.

  1. Determine your requirements

Next to location, your requirements will be the second major factor determining your Airbnb options and final price. Accordingly, if your basic expectations are not met your stay will ultimately not be enjoyable. As such, use the list below as a starting point to develop your own personal search criteria.

Some of your major considerations might include the following:

  • Air conditioning – in Europe and many other non-westernized locations, this is not a given. If you’re planning summer travel and don’t thoroughly enjoy sweating in your sleep, this might be something to make sure is included.
  • Parking – paid, free, available? These options can vary widely, and of course, can also have a big impact on price. Some locations have extremely limited parking available and asking potential hosts about the situation beforehand – or reading the reviews – are key to avoiding heartbreak in this category (if you’re bringing a rental car, of course).
  • Breakfast provided – if groceries or cereal are not your thing in the morning, make sure your host is providing a breakfast. If not, and you’re on a budget, make sure shared cupboard and/or fridge space is available instead.
  • Living space – do you need an entire house or apartment to yourself, or is a single room with shared common spaces (living room, bath, etc.) good enough? The less space and privacy you need, the more broad and economical your options necessarily become.
  • Pets – obviously a very important consideration if your best traveling companion has fur, feathers, or scales.
  • Language – if you’re traveling internationally, this could be very important. However, Google translate and voice dictation are truly breaking down the language barriers. So maybe this doesn’t matter all?
  • Treehouse – in case this is really important to you, it’s an actual option Airbnb. Beat that, Hilton.
  • Superhost – by selecting this option, you are assured that your host meets certain criteria that all but guarantee a great experience with Airbnb. Most importantly, Airbnb hosts cannot obtain or maintain superhost status if they cancel any reservations (with certain exceptions). The possibility of cancellation, of course, being one of the drawbacks I mentioned above. The entire list of superhost requirements can be found on Airbnb’s website.
  1. Last Step – Apply Filters

Using the More filters option and given consideration for the items listed above—and of course, your own personal preferences—simply update the filters to pick your perfect property. Toggling between private home, shared room, and other materially cost-affecting options will ultimately help you reach the perfect balance between price and amenities. I’ve also found that booking well in advance (2-4 months out) is key to finding gems at an affordable price.

  1. Final Notes

Some final things to consider when booking…

Beware of photos that showcase the city but are unrelated to the actual property. This practice seems rather common, as we ran into this during our Airbnb stay in Barcelona. It ultimately had no lasting negative impact, but if we were banking on a particular street view, this may have been a downer.

Be sure to confirm check-in and check-out times, as they can vary widely. This matters if you’re arriving on a late flight and your host isn’t thrilled with letting you in 11:00 pm. Some also charge extra for late arrivals. Conversely, if you’re arriving early (i.e. before check-in) and would like to drop off your bags to explore the city, make sure your host provides this option (Airbnb typically makes it clear if this an option or not).

If you book a room with a host that is not a superhost (to save money or other), I recommend reaching out to them to confirm your arrival date, especially if it’s on a holiday or an otherwise special date. I say this because my wife and I booked an Airbnb in Paris for New Year’s Eve a full four months in advance, and our non-superhost cancelled on us one month before our trip. This turned out to be fortuitous, as we ended up landing a much cooler (and unfortunately pricier), alternative accommodation. Although it was helpful and appreciated that Airbnb provided a discount on the new booking, it was not an experience we would like to repeat. Communicating with your host ahead of time could certainly mitigate your chances of enjoying a similar experience.

There you have it. These are all the things we’ve picked up from traveling Europe the last two years that I thought might be helpful to others. If you have any questions or additional tips, feel free to leave a comment or drop me a note.

Happy trails!

Perhaps Email is Not The Best Medium?


And thank you for your email!

Unfortunately, due to my current workload and the complex nature of your email content, I am afraid that I am unable to effectively engage with you in a one-on-one email conversation. I would submit that a face-to-face or phone conversation might be both more effective, and a more efficient use of both of our time.

Perhaps give me a jingle at your next most convenient time? The best way to reach me is during normal work hours using my office line listed in my signature block below.

Similarly, I’m just as happy to call you as well. Simply let me know a few times that you are free and I will give you a call.

I really appreciate your understanding in this regard.


The message above is a canned response provided to you in an effort to help both of us save time, avoid unnecessary and less fruitful email activities, and execute more high leverage activities while we are at work. Feel free to copy this canned response or use this link to respond to others:

Take Back One Third of Your Work Day with Canned Responses

Just because email helps us to accomplish work objectives does not mean that processing emails is actual, meaningful work (unless of course, you perform a customer service function). In fact, the average office worker spends almost one third of their day processing email.  

If we dedicate one third of our time to something, shouldn’t it be meaningful?

One small slice of the email problem that I would like to help you resolve today is to eliminate any amount of time you might be spending writing similar responses to similar emails. Take a moment to think about the 100s of emails you respond to each week. How many of these would be more efficiently resolved by simply inserting a polite, detailed, but completely pre-written (canned) answer?

Company technical support departments long ago addressed this problem of repeated wheel generation with two simple solutions: Frequently Asked Questions (FAQs) and Canned Responses (that pre-written answer I mentioned). In fact, Gmail has incorporated the ability to very rapidly insert canned responses into the body of an email as one of its basic email functions (it was a Gmail “lab” for many years beforehand).

Here is what it looks like in Gmail:

Although this exact same function is not available with Outlook, the Signatures button on the Messages tab can be used to achieve the same result with almost the same level of convenience and efficiency.

That’s it.

So the next time you find yourself ever writing the same answer to an email that you’ve already written at least once, consider creating a canned response so that you never have to manually type out the same response ever again.

Finally, as an avid user of canned responses, I’ll be spending the next few weeks posting just a few examples of some general canned responses you could use to save time time typing out lengthy responses and also help educate others that abuse their email privileges.

To access all of these canned responses, simply click the canned responses category in the left-hand dropdown menu.