It’s 47 browser tabs. All playing different music at once.
But somehow, it all makes sense to me.

Here’s what the internal monologue actually sounds like:

I opened my laptop to send one email.
Why am I now researching summer camps - acting camp, fencing camp, church camp, AI camp? Am I signing up for too much? But the other option is the kids will stay home. And that’s not an option.

If I don’t write this down immediately it will disappear forever.
Where is a pen.
Why are there no pens in this house.
We have 4,000 pens. Oh here’s that special mechanical pencil I’ve been looking for forever. Shit what did I need to write down?

Where is my phone?
It’s in my back pocket.

I need 12 uninterrupted minutes to solve my entire life.
During these 12 minutes, I have to call AT&T, schedule my hair appointment, oh yes can’t forget botox and the laser appointments, order the cabinet hardware, return the Amazon packages, buy my son’s friend’s birthday present, go grocery shopping, get gas, can I squeeze in a massage?

Did I respond to that email in my head, my dream, or in real life?

I deserve a Haagen-Dazs mini coffee almond toffee crunch for surviving this morning. My diet can start tomorrow, right?

Oh speaking of food. Lunch. It’s 3pm.
I forgot I also eat.

I cannot possibly take on one more thing.
Immediately takes on one more thing. Because I can handle it obvi (ugh why do I do this to myself).

Why is planning for spirit days just as stressful as planning events for work? Neon day? Look like a grandparent day? Wild west? Favorite decade? Twin day? No. No more.

I was just doing something very important.
What was it?

Oh can’t forget to send the meeting invites, but need Comms Team’s greenlight.
Need to also book flight, hotel, car. Reconfirm conference speaking slot.

CEO left ipad on the plane. Ok don’t freak out…
Investor meetings last minute for today? But the day is full of back to back meetings, all of which are, of course, important and hi-pri. Ok no big deal… breathe.

I thrive under pressure.
Creates the pressure.

I need a system.
Spends 45 minutes building a new Notion dashboard instead of doing the task.

I need to learn AI. Let me ask Claude Cowork to help me with something.
Spends next hour prompting and re-prompting and yelling at and apologizing to Claude. I should call her Claudette. Since I call ChatGPT Chad, he’s my homie.

I should be more present.
Brain: Let’s replay that mildly awkward thing from 2014.

Everyone needs something from me.
I also need something from me. Omg look at these white hairs, when’s my next hair appointment?

________________________________

The wild part?

Most working moms with ADHD are high-functioning.

We hit deadlines. Piece of cake.
We show up to meetings prepared. No brainer.
We remember everyone’s snack preferences and dietary restrictions. Easy peasy lemon squeezy.
We manage homes like COO-level operators. I could moonlight as a property manager.

But internally it’s:

“Please do not talk to me while I’m thinking because the thought is fragile and will evaporate.”

It’s loving your career.
It’s loving your partner and your kids.
And also wanting to sit in your car in silence doom scrolling Instagram for 30 minutes before walking inside.
Or hiding in the house somewhere catching up on a Korean drama because I absolutely cannot function and do anything else in that moment (this is where you’ll find me late Friday evenings).

It’s brilliance and exhaustion living in the same body.

And here’s what I’ve learned:

The chaos isn’t a character flaw.
It’s a brain that’s fast. Pattern-seeing. Hyper-creative. High-output.

It just doesn’t always run in a straight line. And that’s ok.

You’re not broken. I’m not broken.

We’re probably just running a very powerful operating system… without a pause button.

And honestly?

We’re still kind of crushing it.

After school in junior high and high school, and even on the weekends, I had to head over there and man the register, peel pounds and pounds of boiled potatoes, scrub and clean sticky, crusty ketchup bottles that never felt clean enough, and refill salt shakers with grains stuck to my hands.

I didn’t understand. Where was my freedom? I was a teen! I wanted to have fun, hang with friends, have sleepovers, talk about boys. I rarely got to watch movies at a movie theater back when that was a cool and fun thing to do with friends. I knew zero pop-culture references (including the ones about Friends!!!). And I basically had the social life of an excel spreadsheet. I was always working (and studying) while everyone was just being a kid.

But you know what? Sometimes, I wish I ran a coffee shop or small restaurant right now where I could have my kids work there a few hours a day. Why? Because the experience at my mom’s restaurant is where I learned the skills no one teaches you in school.

I hated it at the time, but in retrospect, I’m so glad I went through that experience. It built me. So much of who I am now is because of the things I’ve done and experienced in the past, and this was a huge part.

Cleaning ketchup bottles and salt shakers and refilling them seemed tedious and dumb at the time, but the devil is in the details. Everything about the customer experience at a restaurant comes down to the details. Imagine eating your meal, grabbing for the ketchup, the bottle is oily, and there’s old ketchup crust around the rim. You’d lose your appetite. You’d think, if a restaurant can’t keep little things like these clean, what else are they not keeping clean?

Interacting with so many different types of customers (nice, mean, generous, funny) at the register helped me learn about people. It taught me how to anticipate needs, remember names and orders, make people feel seen, and solve problems before they even asked. It also made me realize that everyone is so very different from each other. And even the same person can be different on a day to day basis!

Peeling potatoes taught me about patience and prepping properly before executing. The end result for anything and everything we do requires preparation and setting up the scene and carefully thought out methods.

Plating the food and making it “pretty” helped me learn about presentation. My mom always said people eat with their eyes first, and we must always have red, green, and yellow/orange on the plate to make it look appetizing.

And funny enough, these are all things I still do now as an EA.

When making a salad for Condoleezza Rice for our board meeting, I had to think about colors, variety, presentation, flavor combinations.

When dealing with frustrated or angry executives, I know how to keep my cool and know when to talk, when to stay quiet, and how to read the room. I also know how to listen first, de-escalate, and solve the problem without adding fuel to the fire. The customer is always right, so how do you deal with it and have them leaving happy?

When putting together an event, I know that the little details and preparation are what matter. So depending on the type of event and purpose, I focus on florals, food choices, lighting, colors of linen, types of chairs, ambience, room, views, etc. No one really notices the details when they’re there, they think that’s just how the room came or that’s just how the tables look, but they do notice when they’re not there.

At the time, it felt like I was stuck in a restaurant.

Turns out… I was in training.

Training for reading people.
Training for anticipating needs.
Training for handling chaos with a smile.
Training for a career built entirely on details.

I didn’t know it then, but my first EA job started behind a cash register at the ripe old age of 12… 32 years ago today! :)

If my calendar was packed, my inbox was overflowing, a few different events were in progress, and I was triple-tasking while eating lunch at my desk (spoiler: skipping lunch entirely), I thought this meant I was crushing it. I equated being in constant motion with being a high performer. The more I did, and the more I could handle, the better I must be… right?

Wrong.

The more I did, and the more I could handle, the better equipped I must be to handle a C-level executive, right?

Also wrong.

Over time - and through many hard lessons - I learned that being busy isn't a badge of honor. It's often just a sign that something’s broken. Maybe it’s a lack of delegation. Maybe it’s poor boundaries. Maybe it’s just that I was doing too much of the wrong work.

The better I got at my job, the more intentional my work became. It’s not that I cared less or did less - it’s that I got smarter about where to focus my energy. I learned to say “no” (professionally, of course), and to prioritize the tasks that truly move the needle versus the ones that just fill up time. I also got really good at anticipating my exec’s needs before they even said a word, so my efforts were sharper, faster, and way more impactful.

Here’s the secret no one really tells you: A seasoned EA doesn’t just execute. We observe. We pattern-match. We notice the little things. We anticipate. And that’s where the real magic happens.

Early in my career, I’d jump the second my exec handed me a task. No questions, no hesitation - I was on it. Now? I pause. I give it a beat. Why? Because I’ve learned that nine times out of ten, they’re going to change their mind.

That email draft I just spent 20 minutes perfecting? Useless, because now they want to go in a different direction. The calendar we just finalized? Nope, now they want to meet in person, not virtual, which means we have to buffer in travel time, which means we have to move the other meetings that now conflict. That “urgent” deck? They don’t need it anymore. That flight they said they wanted you to book? It’s going to change.

With experience, you realize that not everything requires instant action or any action at all. Sometimes, the smartest move is to wait. To observe. To anticipate the pivot before it happens. It’s also important to understand the “why’s” so you know how to execute and plan in the future and get into your exec’s mind.

EAs also need to be “on” 24/7, but that doesn’t mean we should be working 24/7. There’s a huge difference. Being available doesn’t mean being busy. It means we’ve set up systems. We’ve planned ahead. We’ve created breathing room, both for our execs and for ourselves.

Our jobs are high-stakes, high-speed, high-pressure. But the goal isn’t to burn out or be in a constant state of motion. Busy doesn’t mean better. The goal is to be effective, strategic, and calm in the chaos. To be the eye of the storm. And that doesn’t happen when you’re running yourself ragged trying to do everything for everyone all the time.

So to the newer EAs out there: I see you. I’ve been you. I used to think supporting 3-4 execs and having a 200-tab Chrome window meant I was killing it. Turns out, the real flex is knowing what not to do. Knowing when to pause, when to wait, when to pivot, when to speak up.

As you grow in this career, you don’t stop working hard - you just stop wasting time and energy. You still show up, stay sharp, and stay on. But now you learn when to act, when to wait, and when to let your exec change their mind before you’ve built the deck, booked the travel, ordered the sushi that they no longer want, and printed agendas or taken meeting notes that no one will read.

Now your time is spent on the things that actually matter. Not performative productivity. Not frantic scrambling. Real work. Thoughtful work. Work that moves the needle.

So yes, you should still work hard. But also work smart. And work with intention.

Master the pause. Own your boundaries (after you’ve built trust). Lead with strategy, not chaos. That’s how you level up. And remember: just because you can do everything, doesn’t mean you should.

And please, no more “quick favors” for people that turn into three hour detours.

Recently, I came across a reel from a Division 1 coach sharing her secret to recruiting top-tier athletes. Her approach, I realized, is exactly how executives should think about recruiting their EAs—and it’s also a perspective every EA should keep in mind, since we are the athlete in this scenario.

Here’s the gist: when scouting highly ranked athletes, she doesn’t just watch how they play—if they’re ranked, their skills are already proven. Instead, she focuses on who they are as individuals. She observes where they sit on the bench, how they interact with their coach, whether they cheer for their teammates, how seriously they take warm-ups, and how they treat their family after the game.

If you’re an Executive or EA hiring manager, don’t forget to ask questions that will help you learn more about who the candidate is as a person and how they’ll connect with you, your team, and your company. Also, backchannel where you can—ask your network about them so you can learn more. You’d be surprised at how connected we all are.

Ask thoughtful questions to uncover their character and mindset, and think about some of these things as you’re interviewing:

• Are they someone you’ll genuinely enjoy working with? Are they someone who could be well liked?

• Can they represent you, your values, and your company effectively? Do you trust them to?

• How will they treat the team? How will they show up for their team?

• What do they value as an EA, and why have they chosen this career?

If you’re an Executive Assistant reading this, keep these pointers in mind:

• The world is small. Someone knows someone who knows you or has worked with you. If backchanneling is done on you, will people or past co-workers have good things to say about you?

• Be kind. Treat everyone well, not just the people above you or the people you think will benefit you.

• Everyone is watching. Your work ethic, personality, character, work output, and how you treat others are being noticed by more people than you realize.

• Your reputation is everything. How you make people feel, and what you do and say will either build or tarnish your reputation. And your reputation follows you.

• Act with integrity. Do the right thing, even when no one is watching.

Like the D1 coach in the reel, people are paying attention to more than just your skills and your ability to do the job. They’re observing how you show up in every situation.

A D1 athlete is the best of the best. They have exceptional talent and incredible work ethic. They are resilient, can handle pressure, and have high expectations for themselves. They understand the importance of supporting their teammates on and off the field. They are coachable, take feedback seriously, and always strive to improve. They know how to stay disciplined and manage their time. And they serve as leaders who have influence and set the tone for their team. All while being extremely good at their sport.

These are also the qualities that make exceptional EA candidates stand out from the rest of the crowd.

Are you a D1 Executive Assistant?

If the shape of my nails were off or I wanted my nails shorter, I would think, “should I tell them, should I not”, and by the time I mustered the courage to say something, it was too late to even bring it up because the time had passed. I would end up telling myself “it’s fine, I’ll fix it when I get home”.

Last week, I took my 9-year-old daughter for a mommy-daughter nail date. And despite my own inability to speak up at a nail salon, every time we walk into one, I emphasize how important it is that she learn to speak up for herself if her nails are not to her liking.

I sat in the massage chair, while my daughter sat across the way at the manicure table. I watched her chat with the manicurist, even making her laugh (thank goodness she didn’t inherit my social anxiety gene). When she was done, she came to me and showed me her nails and told me that she spoke up and asked the manicurist to change the color and adjust the placement of the stickers because they weren’t to her liking.

As a mom, I was so proud, and then it made me reflect on my own struggles.

Voicing my opinion growing up was considered “talking back”. I would get scolded for it at home. I also remember speaking up in class and feeling stupid or embarrassed because people with stronger opinions would disagree or I wouldn’t know how to back my opinions if questioned.

Eventually, any thoughts and opinions I had were locked in a box and stored away. It allowed me to just put my head down and stay quiet. I learned not to bother others, not to be rude, and not to be an inconvenience. And the only way I felt I could truly show my value was by studying hard, getting straight A’s and a higher than 4.0 GPA, executing really well, and keeping to myself.

It makes sense why I was a very good Administrative Assistant and Office Manager early on. Those roles require hustle, hard work, and execution… and not necessarily my opinions.

Early on in my career, I was an excellent do-er - an executive or team member would ask me to get something done, and I would do it (of course within reason). I still execute very well today and do many of the things execs and teammates ask of me, but now I speak up, I set boundaries, I let someone know if I don’t think the task is a good use of my time, and I say no if I don’t have time (or don’t want to do it). :)

But back then, I didn’t speak up if I was burning out. I didn’t tell my manager that 5 executives was too many. I never told anyone I needed help. I never gave my opinion about work related requests and tasks. I felt it was my job to put my head down and work harder than anyone else, pushing my own feelings and thoughts and opinions aside.

It wasn’t until I supported this one executive who had a habit of asking me for my thoughts, which made me very uncomfortable at the start. I distinctly remember one conversation (during a time when back to back meetings were unfortunately the norm and he was probably burning out) where he said “You know my calendar better than anyone in this company, what should I change about it? It’s not sustainable.”

I realized, at some point, I had worked hard enough and proven my worth enough to become someone he valued and someone he recognized as being really good at their job. I really was the only person in the company who knew his calendar best. So he was genuinely asking me for my thoughts - whether it was about meeting cadences, whom to meet with, what conferences, events or dinners he should attend, etc.

Learning to voice my opinions and share my thoughts taught me how to handle rejection and push back, how to be tactful, and how to be concise. It taught me that sometimes I was right and sometimes I was wrong, but it wasn’t always about being right and wrong. Sometimes, people just wanted to hear other people’s thoughts to make better decisions.

It also taught me to play devil’s advocate, see things from different sides, and empathize. And it also taught me to start asking other people for their thoughts.

But I also had to work really hard to get to that point. No one will ask you for your opinion if you don’t add value in some way.

I am forever grateful to him, for pushing me out of my comfort zone, for showing me that I actually had something to offer other than hard work, and for teaching me that if you become really great at what you do, your opinions will be valued and considered (even if not always right). This was the beginning of me becoming a much more efficient EA for him and everyone thereafter.

Thank you DW :)

There is no skill called “business.”

Avoid business magazines and business classes. Study microeconomics, game theory, psychology, persuasion, ethics, mathematics, and computers.

- Naval Ravikant

This concept, in relation to our work, is something that I try to relay to Executive Assistants almost every chance I get.

The path to becoming an EA is not a straight, obvious path. There are no two EAs who have had the exact same experience or trajectory. And that’s because we support human beings, and every single human being on earth is different.

Sure, the concept of what we all do is similar. We schedule and calendar, email with others, book travel, do expenses, plan events, deal with board meetings, etc. But beyond that, the experiences we have and everything else we do for our executives are deeply personal and therefore unique.

Because of this, the best way to grow in your role as an EA is simply by doing the job. And by putting in the years. You’re not going to become a rockstar EA overnight, or through certifications and formal trainings, or going to school for it. The only way to really level up is to do the job.

By doing the job, you learn how to build relationships, become adaptable, gain and earn trust from others, become quicker in your problem solving abilities, and make better executive decisions.

By doing the job, you get better at observing and listening to patterns and behaviors. You start to understand human behavior, you can read your executive’s body language, you know how to provide enough context or prep your executive where it matters, and you learn about human psychology by watching the interactions of everyone around you.

By doing the job, you’ll inevitably make mistakes, but be thankful for them. Mistakes are what help you get better at what you do and help you understand yourself better. By making mistakes, you (hopefully) learn from them, you do your best not to make them again, you start to understand why your executive wants things done a particular way, you know what to expect, and you become great at anticipating needs and being proactive.

By doing the job, you also feel all the emotions. Anger, frustration, pride, embarrassment - it’s all part of the job. You’ll reflect on what you could’ve done differently, feel great about the wins, and laugh at how petty you can get (not proud of it, but I’ve been there!). Through it all, you’ll learn more about yourself - what pushes your buttons, what you’re capable of, and how to handle situations with grace.

There is no skill called “Executive Assistance”.

Avoid spending time and money getting certifications and trainings. Or at least don’t put them at the forefront of your priorities.

No amount of hours studying or taking courses that imply that they can teach you “how to be a great Executive Assistant” will make you a great EA.

Instead (and on top of simply doing the job)…

…Read books (fun NYT bestseller books) about human psychology, organizational psychology (Adam Grant is awesome), human behavior, negotiation, stoicism (Ryan Holiday makes this easy to understand), self-awareness, and communication. You are in the people business, so take time to learn about people.

…Watch and study the people around you - how they operate, what gets them energized, what makes them tick, how they interact with others. What’s the difference between people you want to be like and people you don’t? Why do you trust some people or rely on some folks, but not others? Why does someone have a great reputation, but not others?

…And most importantly, look inward. Learn your limits, your bandwidth, how to say no, and how to let things go. Learn what motivates you, what rubs you the wrong way, what pushes you to do well. Learn about the environment that you thrive in and the one that drains your soul. And figure out how to get what you need to do your job well. You’ll only be able to learn these things if you are in the thick of the role.

Everyday is a learning opportunity. Become more self-aware. Exercise empathy. And watch how far basic values like kindness, trustworthiness, and hard work can take you.

The next time you ask yourself “how can I grow in this role?” remember that it takes a lot more than taking courses and getting certifications. Our role is unique. You can’t be taught how to be an EA. You have to be an EA.

Understanding this and how it can and should affect the way you work could be the difference in your ability to grow and be a great or mediocre EA.

I have an EA friend, Shelley Trask, who told a story once about how she was helping her executive prepare for their company’s conference. He was scheduled to be demoing their product soon in front of a live audience, but the product went down! She was running up and down the aisles, making phone calls to people who could help bring their product back up. And amidst the chaos, another EA stopped her, and said “Shelley… don’t run”. She reminded her that her running was making people anxious.

I also heard another story from Chynna Clayton at the most recent eaRISE conference I was at. She was the Special Assistant to the First Lady Michelle Obama. She emphasized how important it was to watch, observe, listen, and learn, and also carry yourself with a presence that represents your executive well. She shared several fun stories where things went wrong in the White House, all of them last minute of course, and she had to handle them with grace and composure because she knew everyone around her was watching her.

Even in our day to day life, if you are a parent, and your child falls and gets hurt, typically depending on how you react, that’s how your child will react. Or when you’re on a plane and there’s bad turbulence, as long as the flight attendants seem to be calm and collected, it keeps your omg-I’m-freaking-the-f-out-right-now emotions at bay.

I remember early on in my career (in hospitality, but also as an EA), all I knew how to do was walk extremely fast, be short and quick on email and chat responses, and freak out. Things always went wrong. We were always busy. So the obvious thing for me to do, and let’s be real, the only thing I actually knew how to do in these situations, was panic lol :)

And naturally, because of the executives I supported, people associated my behavior with what was happening with my executive and in the company. They would look at my calendar to search for clues. They would watch how I operated. They would be curious as to why I was frantically walking to and from one place to another. They would pick up on my nervousness.

I eventually even had to cancel all my 1:1s because I didn’t want to get caught revealing any sort of emotion or reaction on my face when people would ask me questions. Sometimes, as EAs, we know things months before the rest of the company finds out. I’d be damned if a slight facial twitch revealed to others that I knew some shit was about to go down.

I remember needing to be careful of how I said things because they could easily be misinterpreted. I also had to be mindful of what I wrote on chat and email, as well, and I had to be conscious of what I put on my calendar.

Our quick-to-react actions and emotions during chaos is a sign of lacking experience - this is not a bad thing, just a tenure thing. This is why someone who has been an EA for one year will react much differently than someone who has been an EA for ten years.

More experienced EAs have already been put through the ringer :) We have more years under our belt, we’ve been there done that, we’ve seen so many things go wrong that nothing phases us anymore, and we can now solve problems with our eyes closed.

We also know that things work out in the end, or it’s not really AS big of a deal as we thought it was, or that sometimes laughing about the situation is better than panicking. And we also know how to take a breather. I should add that we also have resources, a network, and people we know we can go to who can help us (this is why building relationships is so important).

Eventually, knowing how to solve problems, responding and reacting with kindness, and walking gracefully, with class, amongst the chaos and the fires that surround you becomes second nature.

Know the role you play as an Executive Assistant whether you work at a small company or a large one. Know that even when it doesn’t seem like it because you’re just a mere employee in a sea of 3,000+ people, everyone is watching you because of your role and because of who you support.

They see what you do, they watch how you act, they interpret what you write, and they judge you and your executive and the company based on all that.

Represent yourself and your executive well.

“Wisdom is knowing the long-term consequences of your actions.”

I got out of my comfort zone the other day and went to dinner with 4 people I didn’t know, but who all knew each other. I was invited by one of them, but even her, I only met irl once, so I didn’t really know her well.

This was a big deal for me because I never go out, let alone with people I don’t know.

But that’s beside the point. Story about my social anxiety and ADHD for another day :)

This dinner was very interesting because it turns out, the number of people I had in common with each of them (found out through checking social media, of course) was surprising. I even went to UCLA with one of them during the same years, and we found out, she was my close friend’s roommate for a little while. I was literally two degrees of separation away from each of the 4 “strangers” I had dinner with.

I cannot count the number of times in my life (like at this dinner) where I’ve said to myself “wow, what a small fucking world”. Like thank goodness I was nice to someone or thank goodness I helped this person or thank goodness I worked hard at XYZ company.

One time I helped someone at work who was in a bind, someone I did not support and who wasn’t even my executive’s direct report or on their team. Long story short, they later left the company, started their own company, and asked me to be their EA.

Another time, I worked with a vendor who was just starting to build out his business. I took a chance on him even though he was new because I saw his passion and drive, and I knew the product would be good. 10 years later, his business became huge, and when I needed a last minute vendor for a holiday party because I had someone back out, he came to my rescue and hooked it up because he remembered how I took a chance on him 10 years back (his words, not mine).

Or sorry one more story - essentially a story of how I became an EA. I worked at Nihon Whiskey Lounge in San Francisco, and I got to know so many of my regular customers pretty well. When I applied to interview at Dropbox, I mentioned this to one of my customers, and he happened to be the best friend (from childhood) of the executive I would be supporting. He put in a good word for me because he knew I worked hard, and he was willing to vouch for me.

It’s important to remember that how you behave/act/work/talk/treat others/etc. will affect what people think of you and what they remember you for, even years and decades later. It’s also important to note that people are always watching and noticing what you do, too.

People also tend to remember how you make them feel. They will remember when you helped them when they needed help. They will remember when you were kind. They will remember your work ethic and your drive. And they will remember when you had their back.

It may not seem like it matters now in the moment, but you will reap the benefits from it in the future (or it will work against you if you don’t understand or you disagree about why it matters now, which I’ve also seen happen with other people). Like the quote at the beginning of this post says, “wisdom is knowing the long-term consequences of your actions”.

I’ve found that even as an Executive Assistant, this holds very true. It’s not about networking and getting to know as many people as you can, because that’s all about one’s ability to talk. You can be a great talker and know 100 people, but if your work doesn’t speak highly of you, it doesn’t matter that you know all those people. It’s about letting your actions speak louder than your words.

How hard working you are, how much you help others, how much value you add to your executive, how well you work with other EAs, how trustworthy you are, all of that will matter even 10+ years from now.

It’s what will help you get a job in the future, what will make it easy to schedule a difficult meeting, what will determine whether a vendor will bend over backwards for you or not, and what will make an executive or other EAs and past coworkers give glowing backchannel references about you.

As an EA, it’s important to build positive relationships with not only your executive, but the people around you. And even if you’re not actively building a relationship (because we certainly can’t build relationships with everyone we work with), it’s important to build your reputation. Your reputation, assuming it is a positive one, will speak for itself and is what will help you move forward in life.

The EA world in general is small. Be kind to other EAs. Help each other out. Make things (like scheduling and communicating) easier for each other. Be empathetic. Put yourself in each other’s shoes. And if you have a big EA team, represent and lead your EA team well, especially if you support the CEO.

You’ve worked with EAs in the past who you appreciate and will do favors for, and you’ve worked with EAs who make you roll your eyes or who you’d never provide a good backchannel reference for.

We need to work hard not to be the latter.

Anyway, then a few moments later, she says “I needed WiFi so I’m working from Chanel this morning”. And this made me chuckle. (Also, look at how cute this Chanel store in the Hamptons looks… so demure… is that how I’m supposed to use that word? ugh TikTok)

How often do we, Executive Assistants, find ourselves doing what we can, wherever we are, to make sure we’re able to log online and get shit done?

I wonder if our executives even know that. I wonder if they know what we do behind the scenes to make things appear so seamless, to make ourselves seem so responsive, and how much we stress when we don’t have wifi connection.

Do they know that we pull over on the street or get off the freeway so we could respond to their text right away? Do they know we take our eyes off our kids competing in a soccer game while we respond to their email? Do they know we burned dinner because we got distracted by an urgent question they sent us on Slack at 7pm?

I mean, don’t get me wrong, none of my executives have ever expected me to be responsive at all hours of the day everyday with no breaks. So I’m not mad that they (or anyone else who has never been an EA) don’t know what we do to make their lives easier.

It’s clear that the problem is me :)

I want to be responsive. This is my job after all, I am grateful for it, I enjoy my work, I want to be available and reliable, and I want to stay on top of it. I also want to show them what I am capable of and to prove that they made a good decision in hiring me (holy mother of goodness, this childhood trauma thing keeps popping up in all my writing lol).

Anyway, I don’t know what the point of me bringing this up was. I just thought it was so typical and funny of my EA friend, and EAs in general, to say she was working from Chanel in the Hamptons because that was the only place she could get good wifi, and she needed to work at that moment. When someone says they’re at Chanel, you’re not picturing an EA with her laptop, hunched over, borrowing wifi, typing away, trying to work.

We really do do whatever we can to get shit done, don’t we? Finding wifi so we can work is just the tip of the iceberg. The rest of the iceberg is loaded with innumerable stories that will blow people’s minds when they hear them.

Like has your executive ever flown from San Francisco to New York to spend a few days for work, and then planned on leaving for London from New York for a slew of business and customer meetings, only to realize, very late the night before they were supposed to leave for an evening flight to London, that they had forgotten their passport?

And then did you have to drive an hour to their house in SF at 5am, let yourself in because you know the code obviously, search for this passport that was in a nightstand drawer in their room where their brother happened to be sleeping because he was house sitting, and quietly without waking him, grab the passport and secretly leave the house like you’re some sort of stealth ninja thief in the night sky leaving no traces behind?

And then, did you have to drive to the San Francisco Airport, get to the United desk so you could purchase whatever flight left for New York the soonest (this was before it was very easy to purchase flights online) so that you could get on it yourself with his passport and hand deliver it to him upon landing in New York? And then plan to fly back on the next available flight?

Yes, it would have been an absolutely ridiculous story if I ended up on that plane. Actually, it’s still a pretty memorable story for me. I was ready and prepped to get on that first flight out, but lucky for me, the United attendant at the desk let me know (after I vented about my predicament) that they actually had a courier plane that could take the passport with them and deliver it to the United desk at JFK within a couple hours of landing.

I filled out all the forms and crossed my fingers and prayed to God that all would go well. And long story short, it did. My exec got to go to London on his 8pm flight that evening. And I went to the office before it even hit 8am.

Our execs (and again, anyone who has never been an EA) will never know the hoops we jump through or the things we are willing to do in order to make their lives easier. But that’s ok. We don’t need to tell the world about it. It’s just what we do. It’s what makes us good at what we do. It’s what separates us from the rest of the company. It’s why they trust us and rely on us.

Hopefully, they feel it and see it and appreciate it. I do think they may not always see or know the details, but deep down they know we take care of them and do what we can to help make them successful.

If you’re an executive reading this, remember that when things are going very smoothly, the event is going off without a hitch, everyone with their 20,000 dietary restrictions is happy with the food and drink options, your calendar looks fabulous, everyone comes to your meetings prepared, you’re able to make it to your kids’ sports games, etc. it’s because a ton of work, thought, collaboration, creative problem solving, and favor pulling went into it in the background. It’s never just smooth by accident.

Aaaanddd… if you’re an EA reading this, I see you :) Go on with your bad self!

The ironic thing is, “what should we eat for dinner?” is my absolute least favorite question in the world.

It’s not that I don’t know how to cook. I think I cook my signature dishes pretty well, thank you very much. And it’s not that I don’t enjoy cooking because when I cook, I get in the zone. It’s just that I don’t know what to cook.

If I was living by myself, I could live off of rice, over easy eggs, soy sauce, and sesame oil with a side of kimchi everyday. But I have 3 other humans to feed, all 3 have different tastebuds, what they want to eat in that moment will depend on their moods, and all 3 are picky in their own way lol. (Shoutout to my husband who will also cook and save me from meltdowns on days my brain simply cannot function.)

What does make it very easy for me though is when they tell me what they want to eat.

“Can we have salmon and rice tonight?” Absolutely!

“What about donkatsu curry for dinner?” Gladly!

“Oh I feel like an Italian sandwich for lunch.” Coming right the f up!

There’s something about being given a direction, a nudge towards the right path, if you will. You don’t have to tell me how to make the sandwich or what you want in it. I can figure all that out. You just have to tell me what you feel like eating or what type of cuisine you feel like eating. And then, I can execute.

I realized that this translates very seamlessly into my work life.

I am not good with a blank slate. My strengths are in execution. They are not in coming up with a plan, starting with a blank piece of paper, or putting together processes. Some people are great at those skills, and I need them in my work life. But me? I’m no bueno when it comes to those things.

Let’s take events, for example. I’ve done plenty of events in my lifetime to know what I’m good at and what I’m not. If my executive were to say “can you plan a team event for next quarter?” that would give me anxiety. Mostly because my mind can come up with over a hundred different ways we could have a “team event”, not because I don’t know how to plan one.

Over time though, I’ve learned to ask the right questions to narrow down my executive’s expectations. Give me some sort of direction, and I can run with it.

What is the purpose of the event? The “why” matters, so tell me why you want to have this event.

What outcome are you hoping for? Are we trying to build morale? Is this just team building? Do you want everyone to feel energized? Are we celebrating?

When were you thinking of having this? After the product launch? Combined with a hackweek? After performance reviews? Before or after the summer when people go on vacation? Is there a RIF (i.e. layoff) or some sort of secret thing that’s going to happen that I don’t know about that would affect the event date and type of event I put on?

Just give me a little bit of direction, and then you won’t have to worry about it at all. You’ll just have to show up.

It’s a blessing and a curse to be able to come up with hundreds of ideas to someone’s one request (it’s not just with events for me, it’s with gifting, meeting cadences, travel planning, etc.). It shouldn’t be that hard, but for some reason (anxiety?) I make it hard (not on purpose, it’s just the way my brain operates, wahhhh helpppp!).

But I think this is also what makes me good at what I do. I want to make sure that whatever I am tasked with is executed to the best of my ability because I care (maybe too much?).

I want the best possible options and outcomes. I want people to leave an event with positive memories. I want my executive to reflect back to the time when the weeklong Japan office visit was executed flawlessly. I want coworkers to look at their company swag and not want to donate or throw it out. I want my executives and their direct reports to feel like the meeting cadences make sense, and meetings are effective, helpful, and a good use of their time.

I’m not going to always get it right because all executives are different, their expectations are different, and what they mean when they use certain adjectives to describe their vision is different. But as long as I had some direction and tried my best, that’s really all that matters. (I’ve come a long way since needing to make sure everything was always perfect. Yay me for growing! Lol!)

Here’s a picture of what my mind looks like at any given moment (in case not obvious, I’m on the right). If you’ve been following me for awhile, you know this is my favorite meme because it so perfectly depicts the life of an Executive Assistant.

They wanted to go see it, and while I typically may say “no” to “can we please do X?” because I always have so much to do, for the movie, I gladly agreed.

Why? Because I am essentially paying $14 for me ($36 total including the kiddos) to go into a large, dark, air conditioned room where I can close my eyes and semi-sleep (because moms never actually really sleep) for 2 hours while my kids get to watch the movie they wanted to watch. It is a win-win-kill-two-birds-with-one-stone kind of situation.

This reminded me that sometimes, it is worth paying for or paying extra for things, and often times necessary actually, in order to get a peace of mind.

As an Executive Assistant, we come across countless situations where we have to sit and wonder whether choosing to pay more and choosing to do A over B is worth it in that moment.

Is it worth paying $700 extra for a refundable fare, or is it better to save money and book the non-refundable fare and sit with anxiety praying everyday that your executive doesn’t change their mind about their flight?

Is it worth paying $20 extra per person for the highest tier catering option so that the team has more variety in food and everyone’s taste buds are satisfied (and you have less worries), or is it better to save money and go with the cheapest option?

Is it worth spending a little extra to have an on-site coordinator for your offsite in lieu of you or as additional help, or is it better to save money and have YOU act as the on-site coordinator?

Is it worth spending more to hire a reputable car service company who will take care of your executive’s ride in another country to and from the airport and hotel without a hitch, or is it better to save money and google a cheaper option?

The answer is not always clear. And the answer is not always to spend more. Sometimes, it makes sense to stay within budget (or maybe we don’t have the budget) and research different options.

But many times, it does makes sense to choose to spend more… not only for our own sanity, but for our executive’s safety and security in another country, for a memorable experience for our team, and for efficiency in our work, among many other reasons. You just have to ask yourself the right questions. And you have to figure out if the pros of spending more outweigh the cons.

With all that said, I didn’t end up sleeping during Inside Out 2. I went into the theater gung-ho about being able to nod off to sleep, but my kids talk too much and ask too many questions during movies. Also, no matter how many times I tell them to use the bathroom before the movie starts or during the previews, they never listen and always seem to have to go at the most important part of the movie.

No lie though (sorry, I mean “no cap”), the movie was pretty good and had me engaged throughout and sobbing at one point, so sleeping was just out of the picture. It was still a win-win I guess, since I got to enjoy the movie with my kids and had great conversations with them coming out of it. Still tired AF, but $14 well spent.

I get into this self-talk mode of “omg, that was so embarrassing, Janet, please don’t ever say or do that thing ever again!” And that would shape my personality over time.

I went on a date in 2006 (eek so long ago). It was a first date. Dinner was good. Osha Thai in SF when it was hot and hip. Had a couple drinks after. But, long story short, there was no chemistry, and I think it was evident for both of us, which was fine, we stayed friends-ish after.

When he dropped me off, he got out of the car to walk me to the front door. Aww how sweet. Chivalry at its finest.

But then he said something that made me feel embarrassed. “You look great tonight, but in the future, don’t wear white shoes with an all black outfit. You’re not supposed to.”

Speechless and confused and with a nervous chuckle (because I didn’t know how to respond to that, I mean how DO you?), I bid my adieu and went home. And I questioned everything about my outfit choices. I was already insecure about what I wore on the daily (this has been a thing most of my life), but his comment solidified my insecurities. I was officially fashion dumb. What other “rules” do I not know of? How did I never hear about this?

First of all (and I wish I had this thinking back then), clearly I was living in the future. Because all I see nowadays is everyone in all black outfits with white shoes. That’s like the quintessential, SF Bay Area, Tech Designer uniform. And such a classic, monochrome, covid 2020 quarantine outfit. Either way, I am convinced that I was cool back then (my kids will think otherwise), ahead of the fashion game if you will. HA!

Secondly, until recently, like in the last 5 years, I never wore an all black outfit with white shoes EVER again after that. And even today, if I happen to be wearing that (I’m actually wearing that now as I write this which is what spawned this post), I am reminded of what this person said about my fashion choice.

This personality and behavior shift is typical of me though (is it childhood trauma?). It’s not so much what he said to me, it’s more that I grew up hearing something and believing it and altering the way I behaved, like in this situation. This behavior, though, is what contributed to me being a good assistant early in my career and what made me end up loving the role lol.

Essentially, I know how to follow directions really well and do what is asked of me, and I don’t break the rules. (Yep, it’s def childhood trauma)

At the start of an Administrative Assistant career, those types of skills will help. You’re new to the role, you’re figuring things out, you’re learning your executive. If your executive says they like their calendar a certain way, you listen. If they tell you not to do something, you listen. If they tell you what hotel and airline they like, you listen.

It’s helpful to many executives to simply do as you’re asked and get shit done. Just say ok and “don’t wear those white shoes with your all black outfit next time”.

Once you get the hang of the role, you’re able to be proactive and anticipate the needs of your executives. Also, with all the mistakes you’ve made that you learned from, and your own life and work experiences, and the years that go by, you get better at being an assistant and work your way up to more responsibilities and supporting higher executives. At which point, “you end up wearing whatever you want however way you want to”.

When I think of Janet in her mid 20s, I am a little sad for her. For lacking the confidence, for letting others shape how she behaves, for allowing a comment change how she dresses, and for not having a strong backbone.

But I’m also happy for her because it is for those reasons she learned to become a better EA for so many people. It is for those reasons she learned to observe her executives’ patterns and behaviors and listen to their needs. It is for those reasons she learned how to adapt to so many different people. It is for those reasons she gained confidence over the years and learned to grow that backbone.

Perhaps the lack of confidence and insecurities were required at that moment in life. They needed to be there to shape who I would become later and to keep me humble. But I think that’s life anyway, right? We learn from our past and build on it. And because of that, who we are today ends up being very different than who we were 20 years ago.

One of the jobs I had and learned the most from was as a server at The Cheesecake Factory in Brentwood, CA. I am still so surprised I was given an opportunity to work here given zero restaurant background and considering how chaotic of a restaurant this particular Cheesecake Factory actually was.

Before working here, I didn’t understand how difficult it was to work as a server, a host, a bartender, a food runner, an expediter at an incredibly busy restaurant. I always thought, how difficult is it to seat people at a table? How hard can it be to take people’s orders and bring them their food?

God, how naive. If you’ve worked in a restaurant, you get it. Post Cheesecake Factory, I now think it is essential for everyone in the world to work in a busy restaurant at one point in their lives. It would make the world a better place. But I digress…

On one of the busiest nights (actually they were all very busy nights if I recall correctly), one of two servers for the bar area called in sick, so they put me in there to cover her.

Now, at age 42, and having had a number of drinks and work experience in my life, if I was a server again, I could run circles around that bar AND with my eyes closed. But back then, at age 21 (shit that was 21 years ago!!), when Southern Comfort shots, Smirnoff Ice, and Adios Mother F’ers (omg I’m gagging) were all I knew of alcohol, I had no business serving in the bar.

My very first customer that evening ordered a “vodka martini” among other things. So I quickly wrote down “vodka martini” on my scrap paper and took the rest of their order.

I got to the POS machine, clicked on “vodka”, then “martini”, and moved right along. Easy peasy lemon squeazy, right?

The bartender calls me over. “Janet, did they say what kind of vodka they wanted?”

Fuck, I don’t know. Regular?

“Oh and how do they want their martini?”

Omg, what does that even mean? In a triangle glass?

“Did they say what flavor?”

What? There’s flavors??

I felt dumb because I was ruining the momentum of the bartender, I had to go back multiple times to the customer, and I had other tables to tend to but it was clear I was flustered and freaking out. That was a lesson I would never forget (clearly, since I’m writing about it now).

Anyway, I swear there are 500 million different ways you can drink a martini - you can have it classic, up, shaken, stirred, extra cold, dirty, extra dirty, Gibson, dry, wet, perfect, flavored (like lychee, espresso, etc.), with whatever vodka or gin you choose, etc. And don’t even get me started with all the fancy, flavored martinis out there that use different liqueurs, juices, syrups, and rims!

When I was at a dinner recently, my husband got an Extra Dirty Goose Martini with extra olives, I got a Tito’s Lychee Martini but asked for it to be over ice with a straw (I know, blasphemy, shush), and my friend got a Lemon Drop Martini. This made me realize that for every person out there who drinks, there are certain flavors, types, and ways of drinking it that work for each of them.

Executive Assistants are like martinis - every EA is going to be unique bringing different strengths with them, and every EA will have particular execs they work better with than others. In the same vein, each executive is going to work better with an EA who has a certain personality style, working style, number of years of experience, sense of humor, way of communicating, etc. that fits them.

And you know what? That’s ok. That’s preferable actually. Because knowing this will help you, as an EA, find the right match to an executive you could potentially work well with, and it will also help the executive understand that connection might be a better hiring indicator than bullets on a resume.

I’ve supported over 45 executives in my lifetime. I’ve learned to adapt quickly to all of them, and I like to think that I had a great relationship with all of them. But even with that experience, there were executives I liked working for and with better than others, and I’m 100% positive that even though I may have gotten along with and learned to adapt to them, I, and the way I did things, was not everyone’s favorite.

If you’re an EA looking for a job right now, figure out who you are as an Executive Assistant and what value you bring to the table, and find an executive who needs and prefers those qualities and characteristics in their work life.

In other words, if you’re an Espresso Martini, don’t work for an executive whose go to drink is an Extra Dirty Martini.

Good luck, and hope you (whether you’re an EA or an executive) are able to find your match.

Cheers!

It’s a day where admins across the board are celebrated for everything they do behind the scenes to bring order to chaos. And we sure as hell do a lot.

But why do I feel so undeserving of this day?

Every year since I’ve been an EA, I would get nervous on Admin Appreciation Day. For someone who thrives off of being behind the scenes, this is the one day a year I would be in the spotlight, and that made me uncomfortable.

So what would I do? I would shine that light on others.

On this day each year, I made it a point to buy boxes of donuts or chocolates or cookies for all the folks at and outside of the company who helped me do my job really well. This included the entire IT team, the Front Desk, the Security team, the Shipping & Mailing department, the Kitchen/Coffee Shop teams, the parking garage attendants, travel agents or other super helpful external vendors, restaurant managers who helped me pull resos last minute, and the like.

And I would write a note to each of them saying “Today is Admin Appreciation Day, but our team would not be able to do what we do or excel at what we do without the help of your team. Thank you for helping us shine and do our job well!”

As a representative of the Admin Team at our company, I wanted to do this. I’m sure there were folks who disagreed with that approach, but I genuinely believe that we don’t do what we do all on our own, and we should equally appreciate the folks who help us at the drop of a hat.

With that said, the more I think about it, the more I realize this is also the doing of my imposter syndrome.

“Who am I to be deserving of a whole day devoted to my role?”

“Wait, but I’m just doing my job to the best of my ability, why is there a day appreciating EAs?”

To this day, I don’t know if I could ever appreciate and accept Admin Appreciation Day for what it is - a day to celebrate people like me. Not because I don’t believe in it or don’t think admins should deserve such a day, but because under most circumstances, I don’t enjoy being in the spotlight. It’s a me issue.

And also I’m weird… and clearly confused.

I don’t like public shout outs (but, sometimes I do). I don’t like being the center of attention (I mean, sometimes I do, but mostly I don’t). And I’m just here to do my job really well (but also, ain’t nobody gon stop you if you want to give me public recognition lol).

This below is me in a nutshell! :)

All jokes aside, I acknowledge that the job we do is extremely difficult. EAs make the impossible possible. We are resourceful. We are creative problem solvers. We get shit done and make shit happen.

Am I proud of the work I do as an EA, and should admins get their own appreciation day? Yes.

Do I still feel that we should be thankful and show gratitude to all the other folks who help us do what we do? Also yes.

If you’re an EA reading this, props to you for all that you do because I know it’s a lot. And we don’t often get the recognition we deserve because so much of what we do is quietly done without our execs ever knowing.

Have a wonderful Admin Appreciation Day, and I hope you are showered with attention, flowers, gifts, and shout outs from everyone around you!

If you’re on a team that works closely with EAs, thank YOU as well. I know that I’ve had to rely on people like you to help me with emergencies, favors, fires, changes, etc. And honestly, I could not do what I do without people like you.

If you’re an executive reading this, thank you for acknowledging your admin on Admin Appreciation Day, but also don’t forget to appreciate them and show your gratitude for them throughout the year whenever opportunities arise. That’s way more impactful and valuable than celebrating on one day of the year.

To the executives I currently support (and to so many I’ve supported before), you all are the best. Thank you for always making me feel appreciated and cared for in so many different ways, not just on Admin Appreciation Day, but throughout my years working for you.

Happy Admin Appreciation Day!

When I picked her up from school, she was angry and annoyed. Turns out, her best friend, whom we just had over for a sleepover a couple weekends ago, had told her that day that my daughter was her THIRD best friend.

The audacity!! Cue *gasp*.

In comes overprotective, and now equally annoyed, mom. So naturally, I told her “well, you don’t need to be friends with her anyway, she doesn’t deserve your friendship!”

HA omg just kidding, I would never. LOLOL. Deep down inside in a corner somewhere, did a part of me want to say that? May…be. But she’s 8, she can now go repeat things I say at home, so I know better (ugh it’s so hard being a parent).

Over the next several days, we had talks about friendships, and she seemed to understand and feel better.

Fast forward to this past weekend, and that best friend came over for a playdate. I took the two girls out to dinner, and we were chatting about friends at school. My daughter brings up the best friend thing and asks “who’s your first best friend?”. And she answers “Joe, because I knew him since I was a baby”.

Then my daughter asks “what about Emily?” and the friend says “oh I don’t know, I met her in 2nd grade, so maybe like my 16th best friend or something like that”.

And then it occurred to me. The numbers that this friend is attributing to her best friends has nothing to do with how much she likes that person or enjoys hanging out with them like I and my daughter thought. It literally is the order in which she met them in her life!!

I asked her, just to make sure I was understanding it correctly, and she confirmed, and then looked at me like “duh obviously, why else would you number your best friends”.

This whole time, my daughter was upset because she thought that by being a third best friend, she was liked less than her friend’s first and second best friend. But it really meant that my daughter was the third friend she met in her life that is still her friend (they met before kindergarten).

This made me realize how common misinterpretations and misunderstandings happen even in our lives. And now that we have texts and emails, tone of voice or assumed tone of voice adds to those misunderstandings.

As an Executive Assistant, how many times have you run into situations where what you said to someone got twisted, what you typed in Slack as sarcasm got taken seriously, what you sent in an email got forwarded and the tone was misunderstood because the person it was forwarded to didn’t have context?

Or how many times has your executive asked if you have a second to chat, and you thought you were getting fired? It’s not just me, right?

In order to keep our cool, remain calm through chaos, represent our executives well, do our job well, and be a good leader, I really believe we need to be mindful of these things:

• Don’t let misunderstandings linger - go straight to the source and figure it out

• If you don’t understand, ask and clarify

• Don’t get sucked into the drama - stay out of it or put a stop to it

• Don’t assume the one side of the story you heard is all truth, no matter how believable - there are two sides to every story

• Don’t jump to conclusions

• Don’t assume you know someone’s intentions

• Don’t waste emotional and mental energy on something that might be nothing

The reason I can say all this now is because I’ve been through so many situations where I did the opposite of the above. And guess what? It backfired every time, just like how my daughter came home angry and upset that day because of how she misinterpreted what her friend said, when the reality of the situation was so innocent.

Learn from my mistakes. Change your mindset. Change how you interpret the things people say and write and do. Control how you react to situations. Have empathy and assume best intent from others. Don’t get in your own head. Don’t get in your own way. Drown out the noise.

Become a better, stronger you :)

I worked as the Front Desk / Concierge at Hotel Yountville in Napa eons ago.

This was, and still is, a fancy hotel. I helped make 10-15 weekly French Laundry reservations for guests staying with us (Napa concierge had a special number to call back then). I got guests into highly sought after wineries for private tastings, wine tours, cave dinners, and unique Napa Valley experiences. I thrived off of providing excellent customer service and helping our guests create memorable experiences. I was there early, I left late, I took on overtime work, I covered shifts last minute. And I was what I thought was an exemplary employee.

At that time, we were proud of having these amazing, famous, Oprah’s list english muffins in our restaurant, sourced by none other than Napa’s Model Bakery.

My manager raved about them mentioning that he’d had a few (for free) from our restaurant the last several weeks, and that they were incredible. So I asked him to get us some. There were only two of us on my team, and both of us worked ridiculously hard, surely we could get 2 free english muffins. He scoffed and said no and said that we could go buy our own from the restaurant during our break. Yes, buy.

As he was leaving, big, full tears dropped from my eyes uncontrollably. They didn’t even slowly roll down little by little and get absorbed into my skin as I cried. At least then I could do some sort of casual swiping maneuver with my sleeve to mask my crying. No, these tears? They were full and they dropped… onto my thighs (picture blood dripping from a blade onto the floor, low velocity impact spatter style, kudos to crime show education! lol).

He saw this and 10 minutes later showed up with the english muffin, along with clotted cream and strawberry jam in the cute little jars you’d only find at fancy hotels.

I didn’t get to enjoy it the way I should have. My pride had stepped in at that point and was like “No, Janet, excuse you, we are NOT eating this right now.” But 30 minutes later, hunger overcame pride, and I ate that god damn cold ass english muffin. It was aiite. Certainly nothing to rave about.

When I reflect back on my life, there have been multiple times where something like this has happened, and it’s usually when I hit a breaking point and burn out. I would cry these big, heavy, wet droplets of tears over someone simply asking “how are you doing?”.

I realize now though, that it is never about the actual thing or situation at hand. It wasn’t about the english muffin. It’s everything that leads up to it. All the hard work, the long hours, covering for coworkers, bending over backwards to make the impossible possible, the draining customers and guests, my executive who thought my job was easy, being the yes-man, being what I thought was a model employee, the time it took away from my family and my personal life, the regret for missing my best friend’s wedding so that I could meet a deadline my exec asked me to meet only to realize they didn’t even look at my work until a week later, etc.

Here’s what I learned:

• Expectations - Don’t expect certain things or expect things to go a certain way because you work hard. Work hard because you want to work hard. Not because you expect something to come your way. Having expectations of others can set you up for disappointment.

• Good vs. Bad - There IS a difference between a good manager and a bad one. A good manager knows how to treat you like a human being.

• Put yourself first - Go to your best friend’s wedding. Don’t miss out on important events for yourself or your friends and family. Your job and your executive won’t always be with you, but your friends and family will.

• Acknowledgement - I’m not someone who needs to be thanked all the time. I enjoy being behind the scenes. But at the end of the day, all EAs, including me, like being acknowledged and thanked every now and then, especially when we work so hard to help make our execs and their team and company successful and happy.

• Have Empathy - Understand that an exec’s or a peer’s anger or frustration almost always is NOT about the situation at hand. It’s probably stemming from other things that led up to that point.

• Model Bakery’s english muffin (which I’ve had more of since then) is actually very delicious, but only when it comes straight out of the toaster!

Up until that point, I had never “failed” an interview. And I had pretty much gotten every job I interviewed for - granted they were clerical jobs or working at a cafe or restaurant, nothing corporate. So when I had to go through interview after interview in San Francisco’s tech world, it really humbled me.

In retrospect, I’m glad I didn’t get the job at any of those places, and I’m glad I “failed” the interviews because maybe I wouldn’t be where I am today if it panned out otherwise.

Here’s what I learned from those interviews back in 2011, as well as all the hundreds of interviews I did after that where I was either the one being interviewed or the one interviewing:

Thank You Emails

• Now having been on the receiving end of “thank you” emails post-interview, I wouldn’t say these are necessary, nor make or break. Like no interviewer is sitting in front of their inbox waiting to see if you’ll send a “thank you” email, and then are like “yasss, let’s pass them on to the next round” once you send one. HOWEVER, if you do decide to write a “thank you” email to the people who interviewed you, make sure you match their tone, company culture, and vibe.

  • I wrote a “thank you” email to my interviewers at a private equity firm, but I wrote it from my phone as soon as I got in the car. I wrote it in a very casual tone (I thought I was connecting with them this way), and this private equity firm was a suit and tie and heels type of place. I got docked (said the recruiter I was working with) for being too casual and not understanding that this firm was a professional place. As you can tell by the way I write, I probably wouldn’t have fit in here anyway lol.

  • On the flip side, after having received that feedback, I wrote a more professional “thank you” email to a group of interviewers at a startup, and the feedback I got was that I was too buttoned up and not a culture fit. HA!

Think Before You Answer

• Answering interview questions is hard and nerve racking. You can study for them, google possible questions, prepare as much as you can, but sometimes, you’re going to get questions out of the blue that you’re not prepared for. Think before you answer.

  • I interviewed at Pocket Gems (and got rejected). Went through a round of interviews with 7 people, I think? I thought I had done generally well. My last interview was with the CFO. And he asked me “how would you get to know the three executives you would be supporting (CEO, co-founder, and him) within the first month you are here?” And guess what I said without thinking… not once, but twice? I said “I would be like a pimple on your face and just be right by your side understanding your preferences and observing how you work.” Needless to say, he was unamused. Can you tell, that 13 years later, it still haunts me to this day? Like who says that?

Understand What Rejection Is

• Sometimes, the reasons you get rejected in an interview are out of your control. Sometimes, you say stupid shit about being a pimple on someone’s face, and get rejected (though I’m sure there were other reasons lol). But pimple shmimple aside, you have to understand that it’s not always about you, and you have to move on. Don’t dwell. You’ll almost never receive genuine feedback, even if you ask. So there’s no point in wondering why.

  • When I was getting rejected left and right by all these companies, I genuinely thought I was the problem. I wasn’t good enough, I didn’t answer the questions well enough, I wasn’t peppy enough, I wasn’t eloquent enough, I didn’t smile enough, I was too casual, I was too professional, I wore the wrong clothes.

  • But now having interviewed hundreds of EAs, I am realizing that most of the time, it’s not even about you… or I mean, I guess it IS about you, but like it’s about things that aren’t in your control, like how many years of experience you have, what projects you worked on, who you’ve supported in the past, whether you’d be a good personality fit for the exec you’d be supporting.

It’s a Numbers Game

• Rejection is part of the interview game. And it’s ok to get rejected. Sometimes, it might even be for the better. I got rejected from interviewing to be Elizabeth Holmes’ EA at Theranos - can you imagine??? What a blessing in disguise ha. If you think of it as a game, it won’t be so disheartening. Or if you accept that there’s a bigger reason for the rejection that you don’t see at this time, but might later, then it’s less sad.

• Think of every rejection as an exploration of new roles, industries, cultures, companies. I never knew about startups. I was just looking for an EA role, and I interviewed at many different types of companies, firms, industries. Eventually, I was able to figure out where my personality could potentially fit in, what types of people I wanted to work with, and what kind of place I could thrive in because I interviewed at so many places. I sure as hell am not a heels wearing, hair done, makeup perfect everyday type of gal.

• The more interviews you do, the better you get at it, and when the right role appears for you, you’ll be ready for it, which leads me to the next point.

Think of Interviewing as Practice

• Someone once told me that even if I’m not actively looking, I should always be interviewing to keep up with the times. By practicing interviewing, I’ll know what types of questions generally get asked, I’ll know how to answer the same questions over and over again, I can perfect my story and my experiences, I can make mistakes in how I answer questions and learn from them, I can understand human behavior, I can pick up on tone of voice and see what things I say pique the interviewer’s interest, etc.

• Like with all things in life, the more you do it, the better you get at it.

It’s a Small World

• Everyone is connected some how. There have been so many instances where I’ve interviewed candidates, they did fairly well, then I did backchannel referencing on them with people we were both connected to on social media, and the references came back negative, so I passed on them.

• Same happened on the flip side, when people reached out to me asking about people I’ve worked with in the past. I’ve been honest in all my backchannel references, and if I didn’t think you were great to work with based on our work together, then I said so.

• I write about all of this a lot, but in general, just be a good person, be hard working, learn how to build relationships, get shit done, be adaptable, build a good reputation. You never know when someone will be a backchannel reference for you.

Or think about this. Have you ever been to a restaurant where your experience there makes you want to come back or makes you want to write a positive 5-star Yelp review?

The happy, positive coffee shop employee who knows your name and your drink, the supermarket employee who always seems eager to help you out or walks around smiling, the server who made your experience feel memorable… these people all have a vibe to them.

They all make you feel a certain way without them even trying, and they are genuine about it.

They enjoy the work and are happy to go the extra mile, so working hard comes naturally.

Are you that kind of EA for someone?

If you are an Executive Assistant, and you are simply in the role to make a paycheck, and you just “do”, then that energy is going to show. People will be able to see it from a mile away. Sure, you can do the job, but there won’t be anything that separates you from the next “do-er”. And if you think about it, AI can always be trained to “do”, too, right?

But as with all hard workers who stand out no matter what industry we look at, if you’re an EA who truly enjoys the work, and genuinely loves to help people/your exec, you’ll naturally want to work hard to do the best you can to make their lives easier.

You’re probably the type to thrive in challenging environments where you have to problem solve, read minds, be three steps ahead of people, and shield, protect, and know your exec(s) better than anyone else in the company.

You’re probably also the type who can be “done” at 5pm, but you choose to have work email on your phone and would prefer to check it throughout the evening, and you sometimes hop online after your kids go to bed because you wanted to get some work done, in order to get ahead of the next day. I’m not talking about work abuse here where you’re working for an exec who expects you to be available and at their beck and call 24/7 (hopefully, none of us have a Miranda from The Devil Wears Prada as our boss, oof). Instead, these are decisions that you have chosen to make in order to be prepared and a step ahead of other EAs.

You’re the type who also has a great reputation, people speak highly of you and trust you, and you genuinely love what you do.

Of course there is more to being a successful EA and standing out than simply hard work. You have to work smart, be strategic, communicate well, produce great work, build relationships, be adaptable, etc. But all of that slowly and naturally becomes a part of you, and becomes easier to do, if you have “hard work” as the baseline, as part of your foundation as an EA.

If you don’t work hard, it will be difficult to build relationships and communicate with others because you haven’t earned people’s trust. If you don’t work hard, I’m not sure you’d be able to work smart, either. If you don’t work hard, you wouldn’t be the type to want to spend the time and energy to try to be adaptable to people, situations, projects, shifting strategies, etc. If you don’t work hard, could you produce great work?

That’s what I mean by having “hard work” as your foundation. Build your reputation as an EA from that. And then, naturally, the promos, the pay raises, the opportunities will start coming.

Let people be able to see from afar that you have a vibe to you that’s different and that makes you shine.

I remember handling a dozen people’s expenses in Concur (back when receipts had to be scanned in (yes, scanned) and everything had to be added manually and expensed individually). I recall being on the phone with United and Korean Air and credit card companies for hours trying to get a refund on cancellation fees and late fees. I remember printing menu cards everyday for our incredible company cafeteria. I remember taking Ubers and running personal errands for people so they wouldn’t have to spend time away from making our company successful. Like literally, that was how I saw my role - here, let me do the menial tasks for you so that you don’t have to waste time doing it, and instead you can focus on “making our company successful”.

In retrospect, I’m grateful for all those opportunities. I think it helped me gain a reputation of being reliable, trustworthy, hard working, and ambitious. I never felt that anyone was taking advantage of me and my willingness to help them, though who knows, maybe some were. But I truly believed that my job was to take care of everyone so that they could do what they needed to do and what they were hired to do. To me at this time, being an EA was synonymous with being a glorified Generalist. That’s just what I thought I was supposed to do and who I was supposed to be.

Then the company got really busy. Suddenly, I supported 4 executives. And physically, I just couldn’t help everyone anymore. So naturally, I had to start saying no. I was never good at it - the saying no part. I actually burned out every 4 months from overworking, and it would take one instance of someone simply asking “how are you doing?” for me to immediately respond with a waterfall of tears because they caught me at the perfect time of hormone imbalance (well, they probably didn’t think it was perfect timing). I could name a few people (luckily, it’s less than 5) who were the recipient to my uncontrollable tears which truly did come out of nowhere.

But I digress. Eventually, I couldn’t be on hold for an hour with airlines and credit card companies trying to get a refund for $25 or even $150 (my executive at that time actually told me to forego all the late fees and cancellation fees, said they weren’t worth my time, which empowered me even more to just let those small things go). I didn’t have time to research and compare prices for a hotel for my exec’s future travels, I just had to go with the closest nice hotel nearest to our office in that country. I couldn’t spend time trying to negotiate the best deal for car service. I couldn’t do everyone’s expenses for them. I couldn’t print menu cards anymore.

And that’s when I realized that EAs need to operate with a cost benefit analysis system in mind.

• If a task costs less than your hourly rate, you should outsource it or ignore it.

• If a task takes up too much of your mental and emotional space and energy and takes you away from your priorities, then say no and don’t do it.

• If a task adds little to no value to your own work, your executive’s priorities, or to the company’s success, then don’t do it.

• If you’re spending a ton of time trying to save a few hundred bucks, it might not be worth it - think about what else you could be doing during that time that could be more beneficial to the company.

With all that said, I don’t think I could be where I am today if I hadn’t helped and said yes to everyone back then. It pushed me to my limit, which was great, because I could see and feel where my threshold was for stress (mentally and physically). But most importantly, it helped me build tons of relationships with people all throughout the company in different departments. It helped me build my reputation and with that reputation, I was able to start saying no to people and start focusing on being an EA, which I eventually realized there was a whole other side to.

When junior, less experienced admins now ask me how they should say no to people and tasks without coming across as rude, in my head, I say “you have to earn your right to say no” because I really believe that to be true. But out loud, I tell them about this cost benefit analysis approach and leave it in their hands to figure out the right delivery. That seems to be the most PC answer… at least for now, anyway.

I recently planned a week long vacation to Puerto Vallarta with my family. I got an insanely good deal on it - $299 for 7 nights, 8 days at a beautiful resort with resort fees waived. We have a vacation club that we are a part of, and as a bonus for signing away our vacation soul (ugh) and paychecks (*sigh* story for another time), we received 8 bonus free-weeks where we only need to pay the taxes and resort fees. 

I booked this trip 6 weeks in advance, so here I am, hand in hand with my anxiety, for the entire 6 weeks, every single day, imagining, yes you guessed it, the worst case scenarios. Like literally every scenario imaginable.

Why was this so cheap? Nothing is "free" in this world, right? This is normally a $1200/nt+ type of resort, why on earth would they include this on a list of resorts offering “free” weeks? The rooms look amazing online, but am I going to get the room that wasn't remodeled, in an older building, with a view of nothing? Will it smell? Oh, I should also tell my brother in law and my sister where our trust is… you know, just in case.

And so went by the weeks - the questions, negative thoughts (aka planning for the worst), expectation setting, wondering, worrying.

When we finally got to the resort, the room we got exceeded our expectations. It made me think, was it necessary for me to worry and wonder about all the what-ifs leading up to this point? Did I do this to myself to set myself up for low expectations so that when I got there, any kind of "normal" room would've exceeded my expectations? And if I did get a smelly room or an old, un-remodeled room, I wouldn’t have been surprised because I was expecting it anyway? Is this my way of protecting myself perhaps?

If I'm planning an event for work, I do think it's critical to have backup plans. But I realized that worrying constantly isn’t something I have to or need to do. It’s actually counterproductive, a waste of brain space, and emotionally draining. What will happen will happen. I am not actually in control of a lot, even though I’d like to think I am. Being as prepared as I can is great and necessary, but also accepting the way things will turn out is important.

Mindset is an interesting thing. So is perspective and how I choose to view the situation.

On a related note, I'm planning a Mexico company offsite in September this year. I tried hard to convince our CEO to avoid September because google says that it is the rainiest month to travel to Mexico and also is hurricane season. I sent screenshots of google searches and data to my CEO indicating these statistics. And you know what he said?

"Google says that it'll rain on average 17 days in places like Cabo or Cancun. This means that for 13 days, the weather could be great!"

What the f? What kind of positivity nonsense is this? Is he not hearing me? Did he not see the stats? What if there are hurricanes and thunderstorms while we're there? What if this September is an anomaly and it rains everyday? What if there are flight delays and our coworkers have nightmare travel stories? What if the weather ruins our company trip? What if we have to stay inside the whole time? What ifffffff????

"But what if it doesn't rain? What if there are no hurricanes while we’re there? What if September is an anomaly and this year actually has the lowest number of days of rain? What if everything will be fine?"

Wow… Touché…

And that’s when I realized, I need to shift my mentality and perspective. He could be right. Or I could be right. If he is right, fan-freaking-tastic. But if I’m right, we could still make the most of our trip indoors, create long lasting memories, and eat delicious food. Some of my biggest travel memories throughout my life are of the times when things didn’t go as planned - in the moment they sucked, but in retrospect, I’m glad it happened the way it did, and I can now laugh about it.

The point I'm trying to make here is that worrying so much and planning for worst case scenarios all the time is exhausting. It's ok for things to not be perfect. It's ok if something goes wrong. It's ok to have general backup plans. And it's ok to think positively and accept whatever comes my way. It’s even ok to think of the worst case scenarios and plan accordingly. It’s just that it’s NOT ok for me to plan for them and then worry about them the whole. entire. time. until the day of the event. It does me no good.

As an Executive Assistant, when I feel like so much of my job requires me to have everything lined up the way I want it to be, is it so bad if things get messed up here and there? (Lol, as I write that sentence out, my anxiety’s like ‘um hello, yeah, it IS bad if things get messed up, are you insane?’. But also like ‘hey anxiety and perfectionism, can you please stfu?”)

Planning is great. Being prepared is even better. But you know what my CEO taught me without teaching me? Going into planning with the mindset of looking on the bright side and making the best of whatever happens is what is truly next level planning and preparation; not planning for every possible worst case and freaking out about it until the day of the event.