You’re reading The Messy Middle: weekly deep dives on leadership, startups, identity, politics, and how to make high stakes decisions that are intentional and in-line with your values.
⚡ The Jolt
The other day I jolted awake at 2 am and couldn't fall back to sleep. My mind was racing with open loops and irrational fears: what if I don't close the client tomorrow? Why didn't I negotiate this differently? Did I respond to that email? My credit card payment is due and I still need to get paid for that contract. I need to book that flight. Should I have said yes to this? Oo, I should make this video for IG. Oh shit, I didn't post that one thing on LinkedIn yesterday.
THE LIST WENT ON AND ON. And I started to wonder, is it just me? Does anyone else wake up at 2 am and have an anxiety spiral?
So I posted in a bunch of group chats what are the work-related fears that keep you up at 2 am?
And people had A LOT to say.
🫣 Top Ten 2 AM Scaries
1️⃣ AI Obsolescence: “That I’m going to be replaced by AI and I’m missing the AI gravy train by not adapting quick enough.” This one came up A LOT. “Technological advances and lack of up-skilling/training/coaching to keep up or risk becoming obsolete/replaceable.” “My job will be taken over by AI.”
2️⃣ Never Being Able to Retire: “THAT I WILL NEVER BE ABLE TO RETIRE AND HAVE TO WORK TILL IM 99.” “How tf am I supposed to stay motivated to work for 15+ more years im already ready to retire 😭😭😭.”
3️⃣ Never Having Enough Money: “Monthly revenue not meeting monthly expenses!” “Compensation not rising with cost of living.” And one founder told me she was so anxious about “having enough money and health insurance” that she's been working multiple part-time jobs alongside her business.
4️⃣ Being Exposed: “I get nervous I don’t know enough and that will be made obvious to everyone.”
5️⃣ Being Passed Over: “Being nice and easy to work with will lead to being passed over for opportunities. I believe in leading with humility, teamwork, & kindness. But it feels like the corporate world doesn’t reward that.”
6️⃣ A Terrible Boss: “Having to keep working for my incompetent boss who takes credit for all of my work.”
7️⃣ Falling Behind: “It is hard to always stay up to date on the industry and know what’s going on.” She described watching coworkers who are “inherently really curious about AI and want to dive deeper in their free time,” while “I am curious about AI, I don’t spend my free time thinking about it that much.”
8️⃣ Missing a Deadline: “Deadlines for deliverables.”
9️⃣ Failing Publicly: “I mostly don't sleep if i have to give a presentation because I still hate public speaking. I get nervous I don't know enough and that will be made obvious to everyone, either through what I present or when people ask me questions."
🔟 Compromising Your Values: “As my clients are getting bigger they are engaging in more meaningful partnerships with zio entities - so communicating how I’m no longer interested in working with them has been taking up space.”
📌 The Takeaway
What struck me as I was reading through the texts coming back was that almost none of these fears were about not knowing how to do the work, but everything everything surrounding it.
Will AI make my skills irrelevant? Will I ever make enough money? Will people recognize what I bring to the table? Can I walk into a room and communicate what I know with confidence? Can I be ambitious without becoming the loudest person in the meeting? What happens when a great opportunity conflicts with something I believe in?
Some of those questions don't have satisfying answers. I can't tell someone whether AI will eventually replace their job, what the cost of living will look like in ten years, or whether they'll have enough money to retire. The thing that stands out to me as a coach is that a lot of our 2 am thoughts are pointing to skills we haven't learned how to navigate yet.
How do I communicate what I know without second-guessing myself every time someone asks a question? How do I make my work visible and have presence without giving up the humility and kindness that are important to me? How do I evaluate an opportunity when it's great on paper but doesn't sit right with my values?
Those are learnable skills. And they're exactly the kinds of things I work on with my coaching clients.
The transformation isn't becoming the person who never has a 2 am spiral again, it's about becoming the person who pays attention to that and does something about it. It's becoming someone who can walk into the presentation, the difficult conversation, or the career decision with a much clearer sense of what you want to say, how you want to show up, and what you're willing to stand for.
If that's the kind of 2 am thought keeping you awake, let's work on it.
🥨 Snacks
💼 Work In Progress: How I'm career maxxing right now.
🫠 Off-Switch: What it feels like to 'relax' while the world feels like it's crumbling.
⌚ On Time-ish: For my group fitness girlies who should have just left 2 minutes earlier.
📚 Currently Reading: Speaking of 2 am thoughts, I'm currently tuning into Don't Believe Everything You Think by Joseph Nguyen.
See you in next week's mess,
Arshiya
