Jess.lol

Remember when you were a kid, standing at the edge of the diving board? That moment when you'd made the decision to jump, but you were still going through your mental checklist? That's exactly where I am right now, and I couldn't be more excited.

I've made my decision. I'm going to become an independent executive assistant and strategic partner. Not tomorrow - I'm too organized for that! - but soon. Very soon. The plan is coming together, and I wanted to share it with you all because, well, you've been part of this journey through these posts.

Here's what I've realized: over the years, I've developed a way of working that creates real value. I've learned how to juggle multiple priorities, manage complex schedules, handle sensitive communications, and most importantly, anticipate needs before they become urgent. And I've learned that this skill set is most valuable when it's matched with people who truly appreciate strategic partnership.

So here's the vision:

I'll be taking on a maximum of 50 clients, but with a twist. About 10 of these will be dedicated partnerships - the kind of deep, strategic relationships where I can really dive in and make a significant impact. These are the executives and entrepreneurs who need regular, hands-on support and strategic thinking.

The other 40 spots? They'll be for what I'm calling "precision support" - leaders who need specialized help with specific tasks or periodic projects. Maybe it's organizing a crucial board meeting, setting up systems for better time management, or handling particular administrative challenges. An hour here, two hours there - but always with the same attention to detail and strategic thinking that I bring to everything.

And because I understand that needs can fluctuate, I'm building a network. When clients need more support than I can provide, I'll help them find and coordinate additional resources. After all, organizing and optimizing is what I do best!

Why cap it at 50? Because I want to ensure that every client gets the best of what I have to offer. No compromises on quality, no rushing through tasks, no dropping balls. Just focused, high-quality support tailored to each client's needs.

The butterflies in my stomach? They're not from doubt - they're from excitement. And maybe a little from the sheer amount of planning I'm doing! Currently, I'm:

• Building systems to manage multiple clients efficiently
• Creating clear service packages and boundaries
• Developing protocols for handling confidential information
• Setting up secure communication channels
• Planning my transition to ensure nothing falls through the cracks at my current position

Speaking of which - yes, I'm still at my current job. I believe in finishing things properly. My team deserves a well-planned transition, and I'm committed to making that happen. There's something powerful about making a decision but taking the time to execute it thoughtfully.

In the meantime, I'm learning everything I can about running my own business. It's fascinating being on the other side of the organizational challenges I usually help solve! But that's also giving me insights that will help future clients who are building their own businesses.

The target date isn't set in stone yet, but it's coming. Soon, I'll be announcing my services formally and opening up those first client spots. If you're interested in being part of this journey - either as a dedicated partner or for precision support - feel free to reach out. Let's talk about how we might work together.

Because that's what this is really about: creating partnerships that let everyone do their best work. Finding people who value what I bring to the table as much as I value what they're building. Creating something new that benefits everyone involved.

I'm still standing on that diving board, but my checklist is getting shorter every day. And I can't wait to take that leap.

More details coming soon. Very soon.

First, I need to address my last post. I spent a long time debating whether to delete it. It felt unprofessional, perhaps too raw. But after a week of reflection, I've decided to leave it up. Not as a complaint, but as an acknowledgment of something real that many of us face in our careers - those moments when we realize we need to grow in a new direction.

The truth is, that post was a turning point for me. Not because of the situations I described, but because writing it helped me understand something crucial: it's not about what's wrong, it's about what could be right.

Let me tell you about Sarah. (Name changed, of course.) She was an executive I worked with during a three-month interim period last year when her regular assistant was on parental leave. From day one, our working relationship was different. She didn't just delegate tasks - she shared context. We didn't just manage schedules - we strategized about the best use of her time.

One morning, she called me into her office. "I noticed you rearranged my week," she said. I started to explain my reasoning - how I'd seen a pattern in her energy levels during board meeting weeks, how I'd restructured her schedule to give her recovery time between high-intensity sessions. She listened, took notes, and then said something I'll never forget: "This is exactly why I consider my assistant a strategic partner, not just a support role."

That's when it clicked.

The right working relationships aren't about hierarchy - they're about partnership. They're about finding people who understand that different types of expertise have different types of value, and that the best results come from combining them thoughtfully.

I started paying attention to these partnerships. They were rare, but they existed. The CEO who treated his assistant as his strategic right hand. The VP who made sure her assistant was included in planning meetings because "you can't optimize what you don't understand." The director who explicitly acknowledged how his assistant's people skills complemented his technical focus.

These weren't just better working relationships - they were more effective ones. Projects ran smoother. Communication was clearer. Problems got solved faster. Everyone brought their best skills to the table, and everyone's contributions were valued.

I realized I had a choice. I could either continue hoping to find more people like Sarah in my current environment, or I could actively seek them out. I could create a working life where these kinds of partnerships were the norm, not the exception.

And that's when the idea started forming. What if I could choose my working relationships? What if I could build partnerships with executives who already understand the value of true collaboration? What if I could create a practice where my skills could have their greatest impact?

The more I thought about it, the more it made sense. Not as an escape from anything, but as a movement toward something better. Toward working relationships where everyone brings their full expertise to the table. Where different skills are seen as complementary, not hierarchical.

This isn't about running away from challenging situations or difficult people. It's about running toward opportunity. Toward growth. Toward the kind of work environment where everyone can do their best work.

Looking back at my last post, I realize it wasn't really about frustration - it was about clarity. Sometimes we need to acknowledge what isn't working to understand what could work better. The key is what we do with that understanding.

So no, I won't delete that post. Instead, I'll thank it for the clarity it brought me. And I'll use that clarity to build something new.

Something exciting is coming. Stay tuned.

There's this moment I keep coming back to. I'm sitting in our open-plan office, orchestrating a complex international product launch while simultaneously managing three different Slack channels and finalizing next quarter's travel budget. Business as usual. Then I hear it:

"Must be nice to just sit there sending emails all day."

It's said with a laugh, meant to be a joke. The kind of "joke" that's become increasingly common in our rapid-growth tech environment. The speaker - let's call him Brad - is one of our senior developers. He's walking past my desk with another dev, both clutching their fourth cold brews of the day.

I smile politely, the way I always do. The way I did when another Brad (there are so many Brads) mansplained calendar management to me last week. The way I did when yet another Brad suggested I learn to code because "that's where the real value is."

Here's what they don't see: I am coding, in a way. I'm coding in human algorithms. I'm debugging interpersonal conflicts. I'm optimizing systems that run on emotional intelligence rather than artificial intelligence.

Take last month's "simple" all-hands meeting. What the team saw: A smooth two-hour session where our global offices seamlessly connected, presentations flowed perfectly, and everyone got their questions answered.

What actually happened: Three weeks of diplomatic negotiations between competing departments about presentation order. Last-minute crisis management when our APAC team had connectivity issues. Real-time translation coordination for our Latin American office. Careful moderation of the Q&A to ensure junior team members felt comfortable speaking up while keeping certain overly-verbose seniors from dominating the conversation.

All while managing the egos of four Brads who each thought their update should have been given more time.

Don't misunderstand - I love this work. I love the complexity, the challenge, the satisfaction of making things flow. And many of our leaders are incredible to work with. Our CEO values emotional intelligence as much as technical skills. Our COO regularly acknowledges the invisible work that keeps the company running.

But there's this growing disconnect in our culture. A hierarchy of perceived value where technical skills are placed on a pedestal while soft skills are seen as... well, soft. Less than. Optional.

It's not just about the occasional condescending comment or "joke." It's about a broader culture that's emerging in tech, where certain types of work - and by extension, certain types of workers - are seen as inherently more valuable than others.

I watched it happen gradually. As we grew from a small, tight-knit team to a larger organization, the culture shifted. The collaborative spirit that marked our early days gave way to something more... stratified. Technical roles began to carry an unspoken superiority. The "bros" began to cluster, their casual dismissiveness of non-technical work becoming more overt.

There was the time I spent hours reconstructing a crucial presentation after a server crash, only to have a Brad suggest I "just use Google Docs next time" - as if I hadn't already implemented a comprehensive backup system that had saved us multiple times.

Or the time I navigated a potential crisis by noticing patterns in employee feedback and quietly implementing changes before issues became problems, only to have it dismissed as "just HR stuff" in a leadership meeting.

The irony? These same people come to me constantly for help with "small favors" that are actually complex problems requiring significant skill to solve. They rely on the systems I've built, the relationships I've nurtured, the processes I've optimized. They just don't see it.

And maybe that's the real problem. Not that the work isn't valued, but that it's become so seamless, so invisible, that its complexity has become invisible too.

I've started wondering: What if there's a different way to work? What if I could choose to work with people who inherently understand and value what I bring to the table? What if I could build something where technical and emotional intelligence are seen as equally crucial?

The thought keeps coming back, especially on days when I've just finished solving a complex problem only to have someone ask if I can "just" do something that would take hours of intricate work.

Maybe it's time for a change. Not because I don't love the work - I do, deeply. But because I'm starting to realize that loving your work and loving your environment are two different things.

And maybe, just maybe, it's possible to have both.

You know those movies where there's a perfectly orchestrated heist, and at the end, you discover the real genius was making it look like nothing happened at all? That's basically my job description. Except instead of stealing priceless artifacts, I'm stealing time back from chaos.

Let me paint you a picture of last Tuesday. (Names and details changed to protect the brilliant and the... well, let's say "challenging.")

6:43 AM: First Slack message hits my phone. Our Singapore team needs urgent sign-off on a contract, but my exec is on a flight somewhere over the Pacific. Except he's not - because I rebooked him on an earlier flight last night when I saw the weather patterns shifting. He landed 20 minutes ago. Sign-off done by 6:47 AM.

The Singapore team thinks he's just incredibly responsive. He thinks the timing just worked out perfectly. Neither realizes there was any orchestration involved. That's the point.

9:15 AM: Three different VPs are vying for the same meeting slot with my exec. Each one thinks their issue is the most urgent. Each one is partially right. By 9:20 AM, I've reorganized the entire day's schedule like a game of 4D Tetris, somehow finding a way to give everyone what they need while making it look like that was the plan all along.

The real art? Nobody feels like they got the short end of the stick. It's about reading people, understanding the unsaid, and knowing who needs the ego stroke of a prime time slot versus who just needs 15 focused minutes.

11:30 AM: Crisis averted when I notice a crucial detail in an email thread that everyone else missed. A potential PR nightmare transformed into a non-event with two carefully worded emails and one strategic calendar invitation. Nobody will ever know there was almost a problem. Those are actually my favorite wins - the disasters that never happen.

Here's the thing about being really good at this job: when you do it perfectly, it looks like you're doing nothing at all. The meetings flow seamlessly. The right people are in the right places at the right times. Documents appear exactly when needed. Problems get solved before they become problems.

But lately, I've been thinking about this invisibility. About how being good at disappearing into the background can sometimes mean people forget you're there at all. How being the person who makes everything work can sometimes mean being the person nobody sees.

Don't get me wrong - there are executives who get it. Who understand that their seamless day is actually a carefully conducted symphony. Who recognize that their ability to focus entirely on big-picture decisions is because someone else is handling the thousand little decisions that could derail them.

But there are others who... well, let's just say they've gotten so used to things "just working" that they've forgotten things don't just work by themselves.

Like the time I overheard one of our senior engineers explaining to a new hire that "executives don't really need assistants anymore - they just have good systems." I had to laugh. Who did he think built and maintained those systems? Who adapts them constantly as needs change? Who steps in when the systems inevitably fail?

The irony? That same engineer had come to me in a panic just the day before, needing help because he'd accidentally double-booked himself for an important client meeting. I'd sorted it out in minutes, so smoothly that neither client ever knew there was a conflict.

That's the paradox of this role: the better you are at it, the more people think they don't need it.

But here's what I know: being invisible isn't about not being seen. It's about choosing when and how to be seen. It's about understanding that true power often lies in the ability to effect change without needing credit for it.

At least, that's what I used to think.

Lately, I've been wondering if maybe it's time to be a little more visible. To step out of the background and acknowledge that making things work isn't magic - it's skill, experience, and a whole lot of emotional intelligence.

But that's a story for another post.

There's something magical about making things work. Not just work - but flow. Like watching a complex machine where every gear turns precisely as it should. That's what drew me to being an executive assistant, though I didn't know it at first.

I fell into this career the way many of us do - accidentally. Fresh out of college with an English degree and a knack for organizing everything from my roommate's chaos to the local poetry society's monthly meetups, I landed a temp position at a small consulting firm. The CEO's assistant had just left for maternity leave, and they needed someone who could "keep things from falling apart" for three months.

Those three months changed my life.

It turns out I had a superpower: I could see the invisible threads that connected everything in an organization. When the CEO needed to be in Chicago but had a board meeting in San Francisco the same day, I didn't just see a scheduling conflict - I saw a puzzle to solve. When important emails were drowning in an inbox flood, I didn't just see messages - I saw priorities waiting to be orchestrated.

I remember the day I realized this was my calling. The CEO was preparing for a crucial investor presentation, and everything that could go wrong, did. The presentation file corrupted. The backup wasn't backed up. The catering order was wrong. And somehow, in the middle of all this, his daughter called from school with a fever.

Most people would have seen chaos. I saw a sequence of solutions.

By 2 PM, he was walking into that meeting with a restored presentation (thank you, Google Docs version history), appropriate refreshments (thank you, my network of local cafes), and peace of mind knowing his daughter was home safe with the backup sitter I had on speed dial.

He paused before walking into the conference room and said something I'll never forget: "I don't know how you do it, but you make the impossible look effortless."

That's when I knew. This wasn't just a job - it was a craft. A perfect blend of problem-solving, writing, communication, and the pure joy of making things work beautifully.

Fast forward five years, and I've since moved into the tech world, working with some of the most dynamic executives in the industry. The pace is faster, the stakes are higher, and the challenges are more complex. And I love it. Most days.

But that's a story for another post.

What I want to share here is simple: being an executive assistant isn't about being someone's calendar keeper or email filter. It's about being the person who sees the whole picture and knows how to paint in the missing pieces before anyone notices they're gone. It's about being the quiet force that keeps the gears turning smoothly, even when the machine is running at full speed.

And sometimes, it's about being the person who knows where to find a pediatrician at 1 PM on a Wednesday, while simultaneously recovering a corrupted PowerPoint and rerouting lunch orders.

It's not just what I do - it's who I am. And I wouldn't have it any other way.