A Day in the Life of an Introverted EdTech CEO

Peek-a-boo.

An itinerary that proves you can run a company and still avoid small talk at the coffee machine.

This is Jordan’s story.

6:30 AM - The Perfect Start, for a Tuesday

My fiancé takes Jackie out for his morning constitutional, while I enjoy "perfect happiness" – sleeping in for exactly 23 more minutes. This is strategic leadership, people. A well-rested CEO makes better decisions than one who has been dragged out of bed by a snorting, wheezing furball at dawn. Let that furball take the dog for a walk.

This coffee will take you places.

8:30 AM - Fuel for Methodical Minds

Coffee time. Foamy. Very foamy. Every Monday through Thursday morning, Birdie at the coffee shop around the corner insists that "foamy" is simply a preference, not a personality requirement. As someone who's passionate, methodical, and engaged (according to my own character assessment), I need my caffeine delivery system to match my energy. Plus, Birdie’s foam art gives me something to look at instead of making eye contact during her inevitable "How was your weekend?" inquisitions.

8:40 AM - Commute Contemplation

During my short drive to our small office, I mentally prepare for the day ahead. Today's big challenge at Comebackademics? Our new product launch presentation is in 48 hours, and our CMO Kendall just started family leave with newborn twins. Guess who gets to step up? This introvert with stage fright. 

My motto is "Do the best you can with the power you have," and with the slide deck Kendall left me. But right now I'm questioning if my power includes not throwing up on stage. I have done it before–the not throwing up part–but can I do it again?

9:00 AM - Strategic Avoidance

First order of business: Sit down in my ergonomic desk chair for my morning meditation. In reality, I zone out and stare at the wall until the power of whomever compels me to turn on my computer, but labeling it meditation in my calendar gives the time block a little razzle dazzle.

“You’re muted. No, not you.”

10:00 AM - The Mask of Dauntless Leadership

Check in time with my team. Most members join the virtual meeting from different time zones and continents. I tell them how excited I am to work with such an amazing group, as we remain the industry leader in our niche of education technology: helping college and university students age 25 and older complete their bachelor's degrees. I do not tell them that I am panicking internally about Thursday's presentation. 

My face excels in the art of looking calm while my brain runs worst-case scenarios. It's like playing Settlers of Catan – you need strategy, resource management, and the ability to look innocent while plotting everyone's demise.

10:40 AM - Productive Procrastination 

Instead of asking my team for presentation help (because that would be admitting weakness, and for some reason, I can't have that, even though they would gladly jump in), I decide to tackle our wedding reception seating chart. Yes, this Saturday night activity has somehow migrated to Tuesday morning. Arranging people strategically around tables feels easier than arranging words strategically for a stage. At least Aunt Araceli can’t heckle me about quarterly projections if I seat her at a table near the back. But she will try.

11:45 AM - Reality Check

“Strategic Planning Time” is scheduled on my calendar, but Nerd Words is being played on my phone. By me. This is what happens when you try and fail at guitar (finger pain), then consider knitting (too many dropped stitches), and finally contemplate quilting (who has time for that level of precision?). My hands need something productive to do on a regular basis, but apparently "productive" is relative when you're stress-managing.

12:30 PM - Lunch and Wisdom from the 2000s

Eating the last of the fried plantains, peas and rice, and oxtail at my desk, while rewatching clips from Legally Blonde on YouTube. Elle Woods didn't let anyone underestimate her, and she certainly didn't hide her strengths. Maybe my avoidance approach to this presentation is all wrong. Elle would have asked for help, worn pink, and somehow made the whole production look effortless. 

Mental note: Figure out how to channel the Elle Woods essence without the Harvard Law degree. 

Second note: Would wearing a Barbie pink blouse under my suit on Thursday make me look trendy, campy, or kitschy? 

And, do I care?

1:15 PM - The Innovation Hour

This is when I remember why I love this work. Comebackademics doesn't just guide older students on a path through academia. We are dismantling the myth that education has an expiration date. Every student who walks across that stage at graduation is proof that second chances aren't just possible, they're powerful. My team and I are changing lives, for the better. I should put that in the presentation.

“There are no bad ideas. Only bad people. Wait…” 

2:45 PM - C-Suite Huddle (aka Subtle Intelligence Gathering)

During our weekly blue sky session, I look like I am listening to each department head propose a new idea for the company. Actually, I am trying to gauge through the screen whether anyone suspects I am spiraling about the product launch. 

My angst apparently goes undetected as Jan and Barrie brainstorm their concept for AI-generated vegan cheese. Though dairy products are not a practical business model for an education platform, I put a button on the Camembert versus Limburger debate by requesting a one-page proposal within 24 hours, delighting both Barrie and Jan. As the meeting continues, I nod meaningfully, ask annoyingly specific questions, and restrain myself from blurting out, "Does anyone know how to make Kendall’s PowerPoint slides less terrifying?"

“We are friends now.” “Yes.” 

3:30 PM - The Dog Park Revelation

Post-meeting recovery on my office couch allows for daydream time. The best part about my neighborhood? The dog parks. They are perfect for introverts. Well, the introverts who have dogs. You can socialize without having to talk about yourself. Thinking about how Jackie makes friends effortlessly on the grassy knolls while sniffing other canine bums leads to a realization. Don’t worry about looking foolish. Show up authentically. That should be my presentation strategy. Without the bum sniffing.

4:30 PM - Strategic Authenticity

Finally ready to tackle this presentation head-on. Albeit thirty minutes before closing time. Instead of hiding my anxiety, what if I acknowledge it? Incorporate into my delivery. In addition to students, our audience is educators and administrators. They understand that learning stretches you beyond your comfort zone. Maybe displaying my vulnerability would not be a sign of weakness. Maybe calling other people in can be a new way for me to lead. An email from Kendall, with the subject line, “Did you ask for help yet?”, reminds me to stop reinventing the wheel.

5:10 PM - Perfect Day 

Driving home, I think about my plans for this weekend after the big launch: playing catch in the park with Jackie and my fiancé. Joyful, simple, true. That is the energy I want to bring to this presentation. Not perfection, but passion for the work.

“Please, sir. I want samo…sas.”

6:15 PM - Dinner Reflection

While my fiancé plates our samosas and salad, I tell him about the presentation situation running circles in my head. His response? "You have been running a company for years that changes the future of learning every day. You've got this." Sometimes the best leadership advice comes from the ones who see you at your most human. Jackie agrees with a, “Woof.”

7:30 PM - Tomorrow's Promise

As I review my Wednesday schedule, I write in big letters at the top, “ASK TEAM FOR HELP”. Not only because I know that great leaders surround themselves with great people, which I have, but also because if I don’t write it down, it won’t get done. 

Speaking of great people, I need to email that strategic communication consultant my friend Casey referred me to. Calls herself “Professor X for introverted edtech CEOs.” She helped Casey deliver a keynote speech at a conference with a standing ovation.

Maybe she could teach me a thing or two. 

Jordan is the CEO of Comebackademics. She believes that the best presentations happen when you stop trying to hide who you are, and start celebrating why you are.

Mahlena-Rae Johnson is the Professor X whom Jordan is referring to. She teaches you how to talk to people. Connect with Mahlena on LinkedIn here: linkedin.com/in/mahlena 

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