10 Tips on Taking a Vacation (and Derek DelGaudio)

Hi New and Returning Readers,

As you know I always wish I was blogging constantly, but it takes a lot of inspiration and something meaningful to impart for me to blog.  This is partly because I’ve been writing this blog for so long.  I’m also juggling work/life, and I want to be really passionate about what I write and share.  

Every day I feel very blessed in the life I lead.  Whether it’s because it was the 4th of July and I’ve heard too many freedom/USA/patriotic type songs or perhaps it’s because I know I should always be grateful for what I have, the reason is so not important.  I’ve been extremely busy both at work and in my social life and it’s all great and exciting stuff.  Each year gets better than the last and I am astonished how lucky I’ve been.  The high-octane lifestyle had me feeling tired and worn out; one can only operate at a break-neck speed for so long until you need to go on vacation or really unplug and do nothing.  After the long July 4th weekend, I do feel much better and every week, if not every day, I make time for non-work activities too, to get away from it all.  

A week or two ago, it was one of those weeks where my brain just felt tired.  I was stressed out from the pace of work and also the length of a couple of special projects with a long lead time.  I hadn’t gone to the gym and lunch for about a month or two and it was starting to have an affect on me in the tiniest of ways.  In the span of about 48 hours, I made about 5-6 minor mistakes, which is unheard of for me.  While I don’t have 100% accuracy, I’d say it’s pretty high up there as I am such a worrywart and have a fear of failure that I quadruple check stuff, don’t assume anything, also get others to help me proofread, and usually take a stance to over-communicate.  The mistakes were along the lines of typos, not explaining a request so it was 100% dummy-proof, and not catching a detail buried on a multi-page group email that had been forwarded to so many people by the time it got to me that I had to hunt and peck for the bits of information like I was looking for Waldo.  So my mistakes were generally understandable, but I was HORRIFIED and EMBARRASSED because it’s not my work ethic nor how I operate, and it was too many in such a short period of time.  More on this later -- how I bounced back.  Which brings me to today’s post...

Jessica, a reader asked:

“Hi, I love your blog and I find it so helpful for advice, as an admin assistant. I have a dumb question, in your many years of experience, how much vacation have you usually taken in an average year? I imagine that with all that you do, everyone would be completely lost if you went on vacation. What would happen if you worked at a small company where there was no one to cover for you? At your high level, do you always feel pressured to never go anywhere because so many people are depending on you? Thank you :)”

This is such a great question and an important one and I really want to thank Jessica for asking it.  I mentioned to her in the comments section that it came at such a great time!  Let's call it kismet!  I had started a blog post on a partially related subject [this one] and her question gave me new direction and focus when writing it.  So, no question is dumb and I love all questions!

Jessica asked, “How much vacation have you usually taken in an average year?”  

Let me start answering first by saying what typical PTO benefits are.  Anywhere I worked I would usually get a minimum of 2 weeks and the longer I was employed there, I would get a few more days on top of that.  We also got 2 floating/personal holidays, about 3-10 sick days, and also working in the entertainment industry, most places shut down for the last 10-14 days of the year.  We also get most bank holidays, half day or early closure before a long weekend, and some companies close early on Fridays during the summer at 2pm or 3pm.  We also get a mini break when our boss is traveling as the stress level is generally lower and we can catch up on our workload.  

How much vacation I have actually taken each year depends on the company I was at, the role, my boss, and the culture.  Most of my jobs I was able to take my 2 weeks. Being able to call in sick or go to lunch when it was so busy is more of a frequent issue. One of my first jobs me and the other assistant did not go on vacation for almost 2 years, nor call in sick.  It was a demanding role.  We generally got to leave at a reasonable hour - 7pm or 730pm at the latest.  One Friday night, I was there til 930pm.  That was not fun.  Another job, I think I don’t really recall going on a vacation except for taking a couple of days off for a friend’s wedding and they happily allowed me to go.  But it caused some scheduling problems that only my immediate team knew about because they took great care to cover for me and have my back without the divulging to rest of the department why the meeting schedule had to change.  Other jobs, because they were temp to full time, I didn’t even have the benefits of paid vacation time or paid sick days for almost a year.  In that role, I had a huge quarterlife crisis, realized it was not the right job for me though I loved the role (just not the hours).  So, I gave notice, and took off an entire 3-4 months to decompress, do nothing, and return back to a normal state of existing after working 18 hour days for so long.  I’ve also had roles where I was never called outside of business hours, but for 6 months or a year I was working thru lunch until 9pm or midnight because of a special project.  I also have had such stressful jobs that one time a co-worker saw me a couple of months after I left a job and did not recognize me because I was so relaxed and carefree.  And it’s not that I wasn’t nice and pleasant to be around while I was at my stressful job, but they had never seen me outside of work so they didn’t realize it was me because my demeanor was so different that I had to say my name for it to click who I was.  And when people meet me for the first time in person after only emailing or being on the phone they remark that I smile a lot and am more “fun” because they don’t get to see that side of me; there is a disconnect of what they imagined I would be like in person.  LOL  If it wasn’t evident already, I was very much a workaholic the first 5-6 years of my career, by choice, to pay my dues and lay a strong foundation for my career.    

Jessica also wrote, “I imagine that with all that you do, everyone would be completely lost if you went on vacation.”

When I told my team I was going on vacation once, one of my colleagues wrote back and said, “You deserve the break.  We will manage, clumsily, in your absence,”  which was very sweet and made me very happy as I was only in the role for 8 months at the time.  Yay me!

Jessica also asked, “What would happen if you worked at a small company where there was no one to cover for you? At your high level, do you always feel pressured to never go anywhere because so many people are depending on you?”

It always perplexes me when small companies do not hire a temp or have in mind another staff person to fill in for the admin or EA to go on a vacation or call in sick.  It makes zero business sense and is very detrimental to the productivity and progress of the team, department, and the company’s bottom line.  While I was never in a situation where no one was able to cover for me, I have been in situations where I wish they would allow me to train my sub for a day or two so they can be better informed.  There have been other times where I called in sick for a day or two and sometimes had to answer a phone call or try to do email from home because I was literally the only one who had such intricate knowledge of something that trying to train or have someone help me would have it take 3x longer.  It just comes with the territory though and I think all jobs have an aspect of that regardless of field or role.  

I do feel pressure not to go anywhere because I “feel bad,” especially if it is an office culture where most people don’t go on vacation, call in sick, or don’t go to lunch.  There is always that fear of not looking like a “team player” and by going to lunch or vacation, you look like a slacker or are not carrying your weight though lunch and vacation are perfectly reasonable requests.  Through time I’ve learned that it’s best to draw healthy boundaries early, for example, when you are a new hire and have much more leeway.  So here are 10 tips, insights, and things to take into consideration about needing a break from work.

1. As a new hire or during the interview process, that’s when you have the cleanest slate to establish healthy boundaries and train how people will treat you and what you find acceptable.  Always be kind, humble, reasonable, polite, and firm.  Explain that you don’t mind working hard or being in a demanding role, but you’re only looking for roles with work/life balance.  And you’re okay with overtime, but maybe 5 hours a week and not pulling 18 hour days.  During the interview process ask about the company culture.  Ask specific questions about start and end times of office hours, amount of overtime required, if you’re expected to travel, how many people go out to lunch, how many people eat at their desk, if you have to be on call 24/7, how often you will get phone calls at 3am, and what the benefits are.  You might not get all the answers you need, but it’s good to ask.
2. If you are new to the company and company policy states you can’t take vacation for the first 6 months, as soon as the 7th or 8th month hits, take a vacation.  Why?  So people have to adapt what’s it like not to have you there and they have to realize, we need to hire a temp or have someone else sub.  You can also practice by writing out a manual on what they need to do in your absence.  
3. If you have the freedom, train people how reachable you are.  For example, I might read emails after work so I know what’s going on and what’s urgent for the next day, but I don’t actually respond at night because I don’t want people to become used to being able to reach me by email at midnight.  If it’s urgent they can call or text me, but having them see me respond to emails at all hours will just encourage them to always write me.
4. No job is worth your mental health, sanity, or general happiness and well-being.  It took me a couple of years to strategically re-direct my career so that I had work/life balance.  This also means working for an @sshole boss is also not a good idea unless you are really, really, really skilled at not letting work bother you.  Luckily, I knew this lesson from the outset and have not had any nightmare bosses.
5. Always make room for me time, a social/personal life, outside interests, and have other hobbies or skills that can be a source of pride besides work.  Like many people, whether right or wrong, what we do for a living is a large part of our identity -- and a source of joy/pride/happiness (I hope).  When I have weeks at work where I don’t take the time to go to lunch, the gym, or relax, when a tiny mistake at work happens it takes on too much weight because there was nothing to offset it like having a good work out, or trying a new dish while out to lunch, etc.  So don’t put all your happiness eggs in one basket (work).
6. If for some reason you can’t take off a week or two for vacation, use the hell out of your long weekends such as Memorial Day, 4th of July, Labor Day, Thanksgiving, X’mas.  I’ve gone on trips to Ojai, San Diego, Palm Springs, and have even rented home or lofts in the Hollywood Hills or Downtown LA to have a staycation and really get away from my typical daily grind.  Change up something for those 3-4 days as if you were on vacation - stay in a hotel, eat out a lot, get a massage, be a tourist in your own city, read 3 books, take that class you always wanted to take.  You can take a nice break without hopping on an airplane.  Or just have a sleepover with all your friends to keep it low-budget, but fun.
7. Think about time in a different manner.  Often, I look at my year ahead and look at when the 3 day weekends are, when my boss will be traveling a lot, when a difficult deadline ends, and I mark time by thinking of that next break.  If I can get thru this day/this week, my reward is X or the finish line is only a couple of weeks away.  In the US, we have a lot of holidays.  There is almost a day off every month or at least a reason to celebrate and do something special.  For example, in March there is no 3-day weekend, but there is St. Patrick’s Day and green beer or food is fun.  
8. Plan and save for a vacation.  I talk about savings on this blog and I just discovered this great free app called Digit and I love it.  Look into it.  https://digit.co/r/LHt1alA8rI?ab
9. Another great free app for healthy work life boundaries is to have a 2nd phone number.  You can get one with the Sideline app and it’s better than Google voice.  
10. I’ve read a lot of books on happiness and one study says that planning an event or special occasion brings more happiness than the actual event itself.  And the reason why is making those decisions is fun (Chocolate cake for my birthday or red velvet?  Vacation in Hawaii or Japan? Oh the possibilities!), but more importantly the ANTICIPATION of the event is what brings us joy.  It’s like riding a rollercoaster.  The best part of the ride isn’t the dip and zooming down at 130mph.  It’s that slooooooooow climb to the very top, that click click click of the rails as you ascend to the peak, and then finally those last few seconds RIGHT BEFORE the big drop, when you’re in limbo, scared with anticipation when you are just a whisper away of teetering over the edge of the highest point.  And for me making plans brings me a ton of happiness. I love researching where I want to eat dinner next, where I will vacation next, and I will make plans MONTHS in advance.  It might as well be a hobby of mine - making plans, booking reservations, and sending Google calendar invites to my boyfriend.  LOL  There are some weeks where I go out 6 times a week for 2 weeks, but it is typically at least 3-4 times a week.  

And remember a couple of weeks ago when I was horrified and embarrassed I made a string of those 5-6 minor mistakes in a span of 48 hours?  Here’s the story on how I was able to shake it off…

My first answer is to usually find the message and the lesson in whatever I am having a hard time with.  If I come up with something truly meaningful to me, I will blog about it.  So in figuring out how to process how I felt, I thought about if there was something there to blog about.  

Luckily, that evening I had plans immediately after work.  I got into my boyfriend’s car, bemoaned how stressed I was and recounted my day as we made our way through LA traffic to the Geffen Playhouse.  

Aside from the title of the show, I knew nothing about what we were going to see.  The show was called IN & OF ITSELF.  And before the show started, I hear the Geffen staff say to others, “Are you here for the magic show?”  And I wasn’t sure if they were referring to the show I was going to or the one in the next theatre.  (It was our show, but to call it a magic show is not entirely accurate.  It was more like a one man show with a little magical elements to it.)

Before going into the theatre, there is a lobby/reception area, and we were shown a large board with various professions / roles on them.  There were a couple hundred of them.  And if we wanted to take a card that best described us we could.  There was one for an actor, an introvert, an extrovert, a visionary, a volunteer, an iconoclast, an executive, aunt, grandma, girlfriend, etc.  I didn’t see one for executive assistant or project manager, so I chose administrative assistant.  My boyfriend chose clown.  (For whatever reason, I’m not sure why.  It’s not his profession.)  Upon entering the theatre, a staff member took our card, and put it in a big pile with everyone else’s.  The size of the audience was about 100 people so there was that many cards.

As we were sitting and waiting for the show to start, my boyfriend was curious to read the “Program Note” section of the booklet.  And, there actually wasn’t a helpful summary or description.  It’s a note from Derek DelGaudio, the star of the show, on why he hesitated to describe what we were about to see.  Without giving too much away, and if you read the reviews they explain the same thing too, so I’m not divulging much…   

I will say this show was so good, I almost want to see it again, but I fear it will spoil the experience of it all.  

As soon as the show started, I was transported to another world.  Derek is a great storyteller and performer.  I was so engrossed with the show, watching the show made it seem like it was a brand new day and I just didn’t have a mildly bad day at work.  

All those cards of the occupations and roles that we chose that got thrown into a big stack was moved by Derek from a card table to a set of old-fashioned weight scales like Lady Justice is holding.  That was the only time he touched them.  He did not look through them or anything.  He merely moved it from one location to another.  

The show continues and a lot of great things happen.  

However, at the climax of the show, is when it truly hit home for me…  If you go watch the show, you’ll better understand why the impact on me was so great.  

Derek tells us that anyone in the audience should stand if they picked a card that they felt truly represented who we were.  There were some oddball ones in there like space cowboy and the clown card my boyfriend picked.  I stood up, my boyfriend did not.  As you know, I LOVE my job.  I love writing this blog, I love being helpful, I’ve been doing admin work my entire career.  So I felt it was very fair for me to stand up because I identify strongly with being an administrative assistant.  

In all about 30 of us stood up, maybe more.  One by one, starting with my half of the room, Derek looks at each individual and without hesitation, with one shot, tells each person which card they chose.  The room is dead silent.  It’s eerie.  And he tells us if he got it right, that person should sit down.  I’m sitting in the 3rd row.  Derek goes through about 8 people from rows 1 and 2 and says, “You’re a mapmaker.  You’re a mathematician.  You’re an aunt.  You’re a grandmother.  You’re a patternmaker.”  And bam, bam, bam, each person sits down.  

My row is next, but interestingly, he does NOT make eye contact with me.  He switches to the other half of the room and same thing.  Sometimes he’ll switch it up and say, with a gleeful smile to the woman who picked the girlfriend card, “Heeeey, girlfriend!!!! Sit down...”  She sits down.  He rattles off more people’s professions and one by one they sit like falling dominoes, it goes by that quickly.  So I’m wondering why he didn’t make eye contact with me and tell me which card I chose and why he switched to the other side of the room.  And just like that, he again breaks pattern, and switches back to my side of the room -- to my row, to me.     

So now Derek’s staring at me, I am staring back at him.  And it’s still dead silent.  There has been no reaction except people staring back in wild-eyed disbelief.  And everyone is craning their necks to see who Derek is looking at next and guessing their card.  In the silence, I’m guessing he will get my occupation wrong.  I think that’s why he switched to the other side of the room.  He got stuck, blatantly skipped me, so he’ll get mine wrong, right?  And you’ll never guess what happened next…

I’m nervous -- for him, perhaps? (And mildly scared. What is HAPPENING?! And shocked, and in awe, and maybe fidgeting, as the silence seems to grow, but it’s probably all in my head).  He looks at me.  He squints as he stares into my eyes  -- as if concentrating, for the first time in this whole exercise.  Because with everyone else he breezed right through them almost in a single breath.  Is his head tilt real or imagined by me?  

He then points his finger at me, it seems with emphasis, that’s he’s right, he finally figured me out, that what he’s about to say is without a doubt, a fact.  And that’s when Derek DelGaudio, eyes boring into mine, says those 6 magic words.

.

.

.

“YOU’RE THE BEST ASSISTANT I KNOW.”

And I exclaim, “OH. MY. GOD!” and sit down.  

He goes to the row behind me and guesses the woman is an icon and she also says, “Oh my god.”  And he goes through every person and gets it right.  He guesses all 30 of us in a span of 5 min.

Meanwhile, I’m sitting down and mildly freaking out.  All that rings in my ears is:

YOU’RE THE BEST ASSISTANT I KNOW

YOU’RE THE BEST ASSISTANT I KNOW

YOU’RE THE BEST ASSISTANT I KNOW

YOU’RE THE BEST ASSISTANT I KNOW

YOU’RE THE BEST ASSISTANT I KNOW     

It rings in my ears like a mantra, or the absolute truth, or as if I was someone Derek personally knew, so it was a given because he said it with such conviction.  And I’m trying to figure out how he could have known.  My card was so high up on the board because it was in alphabetical order I had to have my boyfriend reach it and give it to me.  And one point I had both my card and my boyfriend’s cards in my hand.  Is that why Derek hesitated?  Did he at first think I chose the clown card?  

Earlier in the day, I was tired, my brain was fried, I was stressed, I did not enjoy the minor mistakes I made, I hadn’t been to lunch or the gym in about 2 months, and I was like BLEH when I thought about work.  And that thought was replaced with a new thought that Derek spoke to me and it could not have happened on a better day.  

YOU’RE THE BEST ASSISTANT I KNOW

YOU’RE THE BEST ASSISTANT I KNOW

YOU’RE THE BEST ASSISTANT I KNOW

YOU’RE THE BEST ASSISTANT I KNOW

YOU’RE THE BEST ASSISTANT I KNOW     

After Derek guessed everyone’s job, he told us, that he only added two words to communicate the card we picked.  You and are.  Still ringing in my ears…  YOU’RE THE BEST ASSISTANT I KNOW, YOU’RE THE BEST ASSISTANT I KNOW, YOU’RE THE BEST ASSISTANT I KNOW…

Like an echo…  

Except he added a lot of flourish to mine.  Like he knew I didn’t believe in magic, and that I’m skeptical, and that I’m very much a realist.  He sprinkled on that extra oomph for me.  He knew my title wasn’t officially/just an administrative assistant.  He didn’t say, “You are an assistant,” or verbatim, “You’re an administrative assistant” like to he said to everyone else — “You are ________. You are ________. You are _______.”  He said I was THE BEST ASSISTANT.  AND he said I was the best assistant HE knew, like he knew a lot of assistants, he was an expert on assistants, but that I was hands down the best assistant ever!  :)

Sometimes when you’re having a bad day, hearing other people’s perspectives of you can restore yourself and help you see the positive aspects you tend to overlook because you’re being so hard on yourself.  And while it’s true Derek doesn’t know me from Adam, what is true is that he somehow, inexplicably knew I was an assistant.  He saw me as I saw myself.  He saw the true me, the real me, the so-very-blatantly-obvious-he-was-able-to-guess-who-I-am-me.

And at the heart of Derek’s theatre show with magical elements, that’s the message:  

Change your perspective, change your life.  

Thank you, Derek DelGaudio, for quite simply, changing mine…

***New “rule” - when you ask me a question for anonymous advice and I answer it, could you write an anonymous comment so I know you're the one who ASKED and read the post?   :)  


As always, I usually tweet any new posts I have. And anyone can email me questions and I respond only via this blog, not to your personal address. 


I also write over at Jobstr.com under Hollywood Executive Assistant. 


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