Recovering Workaholic’s Staycation Gone Wrong:  My Story & What You Can Learn from It.

Staycation Gone Wrong_Maiko Sakai.jpg

There were many things my father taught me back in a day.  One lesson that stuck with me was, “When (notice: not ‘if’) you fall, grab something, anything, on your way up.”

Recently, I attempted to take some time off in a lazy way by making it a ‘staycation.’

The description of “staycation gone wrong” may be a little exaggerated.  In hindsight, it was not as terrible as it seemed at the time, but the experience was not great.  This was one of those moments where my father’s advice seemed quite fitting.

In this post, you will see 3 simple sections: Before, during, and after.

If you consider yourself a “recovering workaholic entrepreneur,” this post can help you plan your time-off effectively, mainly by not doing the things I have done.  So, read on!


The Back Story

Despite my skillful mindset practice involving meditation, continuous education, and other energy preserving strategies, I was burned out.

The reason was obvious.  I had not taken a vacation since late 2015.

Unfortunately, this is pretty normal for entrepreneurs like myself.

Because we can't rely on paid vacations or time-off like regular employees, we end up burning out.  The most challenging part of this predicament is giving ourselves permission to take time off. Sounds simple, but it’s a hurdle that is extremely hard for some (myself included) to jump over.

This process could be made easier if we could just ask someone else to give us an OK.  In some cases, family intervention plays a role in this type of situation (if you are lucky).

I was driven to take 10 days off when I noticed the decline in my level of output.  There were also a number of occasions where I didn't want to complete an easy task.

This was a clear sign of burnout.

Something had to be done. Quick.

I realized that the biggest mistake I've made the past few years led to this moment (and it was embarrassingly amateurish.).

I did not block my time-off in the beginning of the year.  Doing so is key to actually go on vacation.  Without a plan in place, it's so easy to let it slide.  I knew this all too well, yet I still went without a plan.  Guilty as charged.

Now, at the tail end of this year, I had no choice but to get creative and quickly manufacture a break for myself.


Why Staycation?

I opted for a staycation because I was too burned out to plan anything, and managing the logistics involved with a traditional, out-of-town vacation seemed too much to handle.

For some, this may sound strange.  People LOVE to plan their vacations.  So why the dread?

To me, vacations aren’t something I look forward to as a form of an ‘escape’ from my life.  If I am not burned out, I actually do enjoy my work, and I live it.

Another important fact to note is, because I am a New York transplant from another country, even when I was working a corporate job, my vacation days were used to go back to my home country, thousands of miles away.  As you can imagine, these trips are costly, both mentally and financially.

I’ve done some travels in the past, cleverly combining business (i.e. conferences) and pleasure so that I reserve my vacation days to go back home while I traveled at my employer’s expense.  

This is why I have never been to the Bahamas or Costa Rica.  If conferences aren’t taking place there, I am not going.

In a nutshell, my past vacations had to be carefully planned in advance for me to make them work.  In this instance, unfortunately, I did not have the luxury of prep time. Naturally, the next best thing would be… a staycation.

Admiring nature is one way to relax in the city.

Admiring nature is one way to relax in the city.



Downside of Staycation

By far, the main downside is that there's no 10-hour plus flight to yank yourself out of your work environment.  This usually does the trick, and I ‘give up’ on thinking about my work, as I know there isn’t much I can do during the flight.

Then, once I land, I am in a completely different environment where I need to behave differently and speak another language. All this helps to keep my mind away from work.

If you choose a staycation, even if you don't go to your office or co-working space, you still have your phone and Wi-Fi, and you are surrounded by familiar views (of your home, neighborhood, etc.)  

This is dangerous, particularly for recovering workaholic entrepreneurs (and potentially for those who might have a touch of Stockholm syndrome for their overly demanding work schedule and environment.)

That's why creating a clear set of rules is absolutely critical for the success of staycation.  I had to remind myself of this constantly throughout my staycation, and it still went downhill. Let’s just say that I did my best with these rules.  



Out of all that happened, I can say that I am glad to have created these rules.  I came up with three to keep it very simple:

1. Create a theme & evaluation questions,

2. Set boundaries,

3. Forgive yourself if you screw up.


Create a Theme

I've covered the topic of why creating themes are more important than creating goals extensively in this post.  It's the same idea. 

Themes help you to question yourself anytime you need to make a decision. 

At this time, my theme was "healing."  I needed to heal more than ever.  I felt like I was physically & mentally bruised from my core business operations.

For you, the theme can be:

Fresh Perspective
Back to Basics

These are just a few examples. Come up with one that resonates with you deeply.  This shouldn’t be too challenging.

Once again, having a theme for your staycation makes your decision-making process easy.

"Is this going to help me heal?"

This would be the question I would ask myself.  Obviously, if the answer is no, then I won't do it.

Along the line of the "healing" question, I came up with a couple of follow-up questions to help me determine what to do and what not to do.  

"Does this excite me?" (My answer needs to be 'yes.')

 "Can I do this if I were on my regular schedule?" (My answer needs to be 'no.')


Set Boundaries

There's a great podcast episode on "digital boundaries" by Being Boss.

In my daily life, I've been sticking to most of the boundaries discussed in the episode, but I knew I could take it further during my staycation.

I decided to check my email accounts (I'm like you, I have multiple active ones) just twice a day for quick scanning.  You will see how well I handled this later.

I would only check social media accounts twice a day as well for my business. Since I don't check them for leisure anyway, this was easy to do.

Also, I consciously decided to book some meetings if they were part of "healing."  If I knew they would energize me, then it was allowed.


Forgive Yourself If You Screw Up.

This is vital. It would be silly for recovering workaholic entrepreneurs to think they can perfect their staycation.

So, go easy on yourself.

Remember, we are 'recovering.'  We are exposed to numerous factors and triggers that will cause us to (air-quotes here) “relapse.”

If your staycation starts to look like another project, it defeats the whole purpose.  Also, feeling bad about failing will turn into a source of stress. As you will uncover later in this post, there were things I battled throughout.  

I know from experience that anyone who tries this for the first time will experience a bit of shakiness.  This is a process. Know that the more you practice, the better it gets.


How I Prepped for My Staycation

A week before, during the weekend, I wrote out everything I would love to do during my staycation. 

This was extremely difficult. 

It was beyond my mental capacity to think of what I wanted to do for fun.

This was the very reason I turned my break into a staycation as opposed to going on a proper vacation, to begin with.  But at the same time, I knew a little bit of planning could make an immense difference. So, I forced myself to create a plan.  

To make it easier on myself, I made the process somewhat enjoyable. 

I wrote down in a way that people would sign someone's birthday card (see below.)  If I made a list instead... it would have looked like a to-do list, which would stress me out more.

I got to do some of these. I did aim for making it to be "The Ultimate."

I got to do some of these. I did aim for making it to be "The Ultimate."


After I was done, I left my plan alone for a week only because my week turned out to be chaotic. I just couldn't get to it again to tweak or add more.

Looking back, I was almost crawling towards the end of the last work week before my staycation.  Although it wasn’t planned perfectly, knowing my staycation is coming up truly helped me to get through.  This alone shows how not to let this happen to you.

So, how did it go overall?  Here is my daily recap:  


Day 1: Dazed & Confused

It technically started from Friday. In the morning, for no apparent reason, I felt dizzy with fear. "How do I go about this?"

As a result, the morning went on as usual like no vacation.  I ended up working. At 1pm, I was finally able to snap out of it.  I left my home office.

"Baby steps," I told myself. I hopped on a local bus and head down to Brooklyn. 

Texts were still coming through.  I dealt with them. (My phone doesn't ring, and my people know to text if they need me.)

I explored a neighborhood I wanted to check out, and I snapped some photos.

In the evening, I still felt off. I realized this time-off would have been much easier if I had a flight to catch. Maybe sometimes, even staycation, needs to start in a drastic manner. (I took a mental note for the next time.)

I researched events, meditation classes, and other things I was interested in doing at night.  Then, I was totally exhausted from the choices (decision fatigue,) and just shut the laptop.

Southside Williamsburg BKLYN

Southside Williamsburg BKLYN



Day 2: Making It Special

It's Saturday, so it didn’t feel special since most people have the weekend off.

After coming back from my morning walk, I did some chores trying to figure out what to do in the afternoon. I knew that the city will be filled with weekenders and tourists, and I thought about avoiding it.

But then, I got a second wind and ventured into the city.  

I checked out Union Square Farmers Market, bought some produce, took some photos, and stopped at a Thai restaurant I had never been to just to snack.

"Would I do this on a regular workday?"  I asked that question over and over just to be sure I was on the right track.

The day went by slowly – exactly the way I wanted it to be.  And it was OK.

Union Sq Manhattan

Union Sq Manhattan


Day 3: Getting Intentional

It was relaxing to a certain degree.  A perfect day to stay at home and relax. I had been very mindful of the main reason I was doing this.  It was to heal, not to jam-pack my day with activities.

I took a longer walk in the morning to get myself situated.  Then, as I originally planned, I got rid of a ton of clothes.  This was fulfilling. One of the core things I wanted to accomplish was to declutter and reduce my belongings.  

I did some research work I had been putting off as well.  My research included looking up a class to take in the city, etc.  This fit just fine with one of the follow-up questions I had, which was, “Would I do this under my regular schedule?”  

LIC Waterfront QNS

LIC Waterfront QNS



Day 4: Slightly Thrown Off-Guard

Monday - As I expected, I was bombarded by emails in my client email account.  Some required my immediate attention, and I spent a couple hours doing so.

I ended up going on site in the afternoon.  But I decided to eat at one of the favorite places nearby beforehand to lift my spirit.

It worked.  This is a “hole in the wall” place that never gets crowded and that gave me a sense of serenity.  

Opening this one particular email account was a trap.  But, even when I look back, I don’t see a way around it considering my current situation.  This did not ruin my day. You will quickly see, though, that it will become a recurring theme.

Manhattan Chinatown

Manhattan Chinatown



Day 5: Defying the Gravity

Most of my clients are quiet with an exception of one. This has been ongoing, and I ended up spending 3 hours plus dealing with it.

To refocus, I took myself out of the office in the afternoon.

I ventured out to a neighborhood I've never been - Jackson Heights, Queens. Because the place was so different from what I'm accustomed to, it turned out to be a good strategy.  Without exaggeration, it almost felt like I was in another country.

The weather was getting pretty brutal, so I had to cut the trip short. I was back by 5pm to do a call on behalf of my client.

Jackson Heights QNS

Jackson Heights QNS



Day 6: Hell Breaks Loose

I began to wonder if the idea of this staycation was stupid.  I just can't get a break from this one client. I recognized the feeling of resentment, frustration, aggravation in the morning.

With one problem after another, I was starting to feel miserable. 

But I'm a pro.  At least that is what I tell myself.  It's a choice. So, I decided to flip the script after I acknowledged all the negative emotions I was feeling.

"I'm trying something new, therefore my past environment/world will put up a fight to get me back to where I was."

I had no plan of backing down. Luckily, I had already booked a meditation session at 5:30pm - something I've never done before.  This would force me to get me out of the headspace I was in.

I spent the majority of my morning and early afternoon working, then I pulled myself out of the office.

Right before I left, I realized I booked my meditation session at a wrong location.  I meant to go to Brooklyn, but I booked at another location on the Upper West Side of Manhattan.

Because of the way my day was going, I was immediately annoyed.  I caught that quickly and told myself, "Perhaps, this was meant to be."

Since I had 1.5 hours to kill before the meditation, I searched for a coffee shop in the neighborhood. Starbucks is everywhere, but I wasn't feeling it.  Then I remembered a tea shop I've been to - Alice's Tea Shop. 

The weather was incredibly muggy and disgusting.  The shop had enough amount of AC to keep me comfortable for my wait.

I enjoyed their famous scones and Jasmine tea and worked on my creative ideas.  This was incredibly relaxing. I know what you are thinking, “But, you worked.” The work I want to do helps me heal, as this is what I live for.  Putting it simply, I wouldn’t label this ‘work’ at all.

The meditation place was fantastic.  The room was sound-proofed. The silence was incredibly comforting.  

UES Manhattan

UES Manhattan



Day 7: Making a Hard Choice

I decided to go onsite for one of my clients… again.  The decision was based on just one question, "Is this critical enough & going to save me next week?"

The answer was, sadly, yes.  Once the decision was made, though, going in felt less annoying.  To make it even better, I had a one-day free pass at a co-working space already booked for the majority of the day.

Being productive at this serene co-working space was the right way to end the day. 

NoMad Manhattan - While I sit & work on the floor, the person next to me is meditating. A normal scene at this co-working space.

NoMad Manhattan - While I sit & work on the floor, the person next to me is meditating. A normal scene at this co-working space.



Day 8: Reconciliation Day

I came to a realization that my staycation did not turn out the way I wanted.  I recognized this gap between what I wanted and what happened as the most common factor in feeling frustration and resentment.  

I had to reconcile this.

While I continued to semi-work, I was searching for ways to normalize this experience so I didn’t continue to feel miserable.

The first thing that came to my mind was, "It's normal to experience unexpected bad things when you are making changes in your life."

The point is that you don't take that as a bad sign to stop yourself from making that change.

I resonated with this statement, and I repeated it in my head over and over.  Emotions do come in waves.  It's not as simple to just flip the script and move on, though you can definitely get better at this.  That’s why I focused on sticking with the new script that this is normal.

It did help to know that I was on the right track. The mess that surfaced was a sign that I was making a needed change. Now, I had the space to ponder what needed to happen next.


Day 9: Aha Moment Shows Up

Well, what do you know? 

This did not show up while I was meditating or taking a morning walk. 

This did not happen when I was dining with friends.

I was just drinking my morning coffee. I wasn't listening to music or watching anything. It was just me, myself and I.

Out of nowhere, a solution I was looking for appeared in a very subtle manner. There was no light bulb going off or a loud noise in my head. 

Instead, the solution felt like it was being slowly being served to me, like a meal on a flight.  It was as if that's what I ordered, and that’s what was supposed to happen.

The moment I acknowledged it, there was an immense feeling of relief, contentment, fulfillment, and hope.

However challenging this week had been, there was a  clear and critical takeaway. When I'm at the edge of a cliff, I always imagine a clue, or a solution would appear in a dramatic way like, clouds parting and a beaming light comes through, or dramatic music goes off in my brain and "AHA MOMENT" all in caps would show up in my head.

This was an important reminder that it never happens that way. So, paying attention is vital. Otherwise, you might miss those subtle clues.

I documented what I experienced and added some notes so that I could implement right away.  


Day 10: Reflection Day

I went through some photos I've taken to remind myself about the past 10 days to see if I missed anything. 

When I was alone, out and about, I felt I was getting what I needed - healing.  This was not a major discovery. I knew what works for me when I am burned out, and these things worked as well as I imagined.

But... Yes, there's this nagging 'but.'  I don't feel rested. I don't feel I had a break.  I don't feel I got what I wanted.

Clearly, I am still struggling with the gap between what I had hoped and what had happened.

The thought that came to my mind was, "This is one of those times where I won't know the true verdict until at a later time."

The jury is still out for the final verdict.

I settled on that idea.  It seemed like it was the best, logical explanation to help me move on.

Greenpoint BKLYN - Parks are the best places to reflect.

Greenpoint BKLYN - Parks are the best places to reflect.


6 Takeaways from this Experience

1. Cut It Short & Start Off with a Big Bang.

I didn't need total 10 days of lukewarm time-off. It ended up being slow torture.

Instead, next time I can start from Thursday. An intense 4-day break-away to shut down everything seems way more appealing after this experience.

Also, the first day probably mattered more than anything.  There are ways to kick off a staycation in a drastic way. You could book something fun in the morning that you have no choice but to get to, or you could stay at a friend’s place an hour away.  This is doable.


2. Don't Tough It Out. Plan Ahead.

When you are already burned out, there is no brain capacity to plan anything effectively. 

Especially for those who aren't good at intentionally (and enthusiastically) setting aside some time for themselves, myself included, it’s necessary to block out time in advance. 

I learned this the hard way. I planned the best I could, but it could've been much better if my head was in the right place.


3. Tell People You Are Unreachable.

Even if this is not the case, just let them know you aren't reachable. But, mind your social media posts that may reveal where you are.  

Just to hedge the risk, why not stop checking your social media if you are not using it for your business?  That way, you won’t make mistakes by posting while you meet up with your friends at a local restaurant tagging that location…


4. Don't Come up with an Activities-Based List.

It was a good idea to create my wishlist in a fun format just so that when I am having the "deer in the headlights" moment, I have something to reference.

But, even then, I felt "obligated" to do things that were listed. This isn't helpful especially when you want to recuperate.  

Instead, it should be centered around “how I want to feel by doing XYZ.”  I thought I was clear on it, but looking back, I now think I could do better.


5. You Are Either In or Out – There is No Between. 

I'm weird. There's a set of business activities that I consider therapeutic. I don't want to say that I shut that part down unless I feel the need to do so. 

However, when it comes to things that you don't normally prefer doing, there's no halfway. I made a mistake by inviting them in. 

Saw this on the street. (Not staged!) I thought, "Ah, this is me."

Saw this on the street. (Not staged!) I thought, "Ah, this is me."



6. Don't Expect an Immediate Effect.  Take a Step Back and Look at It as a Whole.

On the 10th day, I was not at all ready to go back to my regular schedule.  With the staycation behind me, I couldn’t help but to search for answers.

But the thing is, it takes time to put into perspective.  

I thought a lot about whether I had completely ‘healed’ physically and mentally.  The answer was no. Yet, looking at what I did during the first week back, I could see that my patience level was back up.  I also completed a task I was dreading, which tells me that my energy level was restored (to a certain degree.)

These things are subtle.  They don’t show up on a stage with glittering confetti flying around.  

Would I have had that ‘aha moment’ if I didn’t take this pseudo-time-off?  Who knows. Maybe not. Or, maybe much later.

The most crucial thing is to continuously ask questions such as:

  • What does this mean in my life overall?

  • What activity gave me the most energy?

  • What is the gap between where I am and where I need to be?

  • How would I go about addressing this gap?

  • Why is this important?

Regardless of how fulfilling the overall experience was, this time-off gave me a whole new perspective on what needs to change in my life and business, which I had been thinking about for a long time.  In a sense, this time served its purpose by providing a space to pay more attention to what the change entails.

I also learned that staycation is tricky to pull off.  However uninspired I was, I should have designed a drastic way to change up my environment.  What I am going to try next is a series of short getaways sprinkled over the year. Keeping it short & intense seems like a much better fit for my personality.

So, there you have it.  

It would be terrific if you share your own staycation experience in the comment section below.  Tips and tricks are welcome as well!