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Andrea Michalek

@thatandream.com
3.1K followers 864 following 1.2K posts

🎯 I am a: serial entrepreneur, mom, leadership coach, community builder and diy-er. 🔥 passions: product management, women in tech, startups, AI, leadership 🚀 my path: developer → CTO → startup CEO → exit → VP PM → brain injury → consultant/coach

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Andrea Michalek @thatandream.com · 21/09/2026
I write about leadership, building things, and the questions I’m figuring out along the way in Leadership Advantage. Subscribe here: www.leadershipadvantage.xyz/newsletter
leadershipadvantage.xyz
One Insight. Pressure-Tested in Real Life. | Leadership Advantage Newsletter
Join leaders who want to move beyond incremental thinking. Practical leadership ideas from Andrea Michalek, tested in real life before she asks you to try them.
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Andrea Michalek @thatandream.com · 21/09/2026
The higher you go, the more people expect you to have answers. Sometimes what you need is someone you trust enough to admit you don’t have one yet. I wrote more about that here: www.topularstrategy.com/blog/someti...
topularstrategy.com
Sometimes leaders don’t need advice
As you become more established in your career, your network gets bigger. But the number of people you can comfortably say, “I have no idea what I’m doing here” to gets smaller. That’s why leaders don’t always need advice. Sometimes they need peers they can trust with an unfinished thought.
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Andrea Michalek @thatandream.com · 21/09/2026
Your network gets bigger as your career grows. But the number of people you trust with an unfinished thought gets smaller. A network and a peer group aren’t the same thing. I wrote about why that matters. 👇
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Andrea Michalek @thatandream.com · 17/09/2026
I’ve been rethinking what a “personal brand” is. Not a more polished version of your resume. A more complete picture of the person behind it. So I rebuilt ThatAndreaM.com around an idea that feels much more like me: Figuring it out in public.
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Andrea Michalek @thatandream.com · 03/09/2026
Full Moon Forum started with a table in Philadelphia. Last week, the Sturgeon Moon taught me the table was never the point. The women, and what happens when you give them space for real conversation, are. Next up: Harvest Moon, virtually + in Philly. fullmoonforum.org/gatherings
Sturgeon Moon participants during the first gathering over Zoom for Full Moon Forum.
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Andrea Michalek @thatandream.com · 25/08/2026
Sturgeon survive by navigating deep, changing water, then rising to the surface. This Thursday, that's our theme for Full Moon Forum's first virtual gathering. What's been taking shape beneath the surface for you? fullmoonforum.org/gatherings
Full Moon Forum event graphic. Text reads "What's been taking shape beneath the surface that deserves your attention now?" Photo of Andrea Michalek smiling. Details: Sturgeon Moon, virtual gathering, August 27, 12:00 PM ET on Zoom. "Request your seat" with link to fullmoonforum.org.
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Andrea Michalek @thatandream.com · 23/08/2026
I spent my career learning how to succeed as the outlier. This year I decided to build a different room instead. That's how Full Moon Forum started, a peer group for innovative women who are done adapting to the room. New post + upcoming gatherings: www.topularstrategy.com/blog/the-adv...
topularstrategy.com
The advice I stopped giving women
After a career spent learning how to succeed as one of the only women in the room, I started asking a different question: What if we built a different room?
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Andrea Michalek @thatandream.com · 23/08/2026
For women founders, executives, and innovators: I’m hosting Full Moon Forum, a private gathering space for women leaders to connect openly and off the record. If you’d like an invitation to our next virtual gathering this Thurs, Aug. 27, request one at fullmoonforum.org.
fullmoonforum.org
Full Moon Forum | The Peer Group You’ve Been Missing
An invitation-only community for women founders, executives, and innovators to build the peer relationships that get harder to find as you become more senior.
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Andrea Michalek @thatandream.com · 07/08/2026
Trying to find a lightweight CRM solution I came to the realization that AI product-bloat is real. This might be the REAL reasons SaaS products are dying. Product managers need to show some restraint in what features make it into their products, ESPECIALLY with AI.
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Andrea Michalek @thatandream.com · 02/07/2026
Details and the invite request for Harvest Moon: fullmoonforum.org
fullmoonforum.org
Full Moon Forum
An invitation-only gathering for women innovators who build, lead, and create. September 25, 2026 · Philadelphia. Space is limited by design.
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Andrea Michalek @thatandream.com · 02/07/2026
Under Monday’s Strawberry Moon, a room of women founders, executives, and innovators talked about the things they can’t say anywhere else. That was the first Full Moon Forum. Next one: September 25 during the Harvest Moon.
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Reposted by Andrea Michalek
May Likes Product @productnerd.bsky.social · 15/04/2026
Toronto Product Conference - May 28 - speaker announcement! Hype! Some of my favourite product people are speaking! @johncutle.fish @thatandream.com @focusedchaos.co Tickets: www.tpma.ca/conference/t... #Toronto #TorontoProductCon #productmgmt
Poster for the Toronto Product Con, Conference + Unconference on May 28, 2026 at the Ted Rogers School of Management.

Headliners: April Dunford, Ben Erez & Marc Baselga, Ben Yosovitz, Colin Matthews, John Culter, Radhika Dutt.

Speakers: Abinandhini Raju, Andrew Shaw, Amber Foucault, Andrea Michalek, Andrew Williams, Angeli Mehta, Balaji Gopalan, Daniel de Repentigny, Emily Reid, Jenya Farris, Joan Milway, John Stetic, May Wong, Mike Ho, Iris Guo, Ross Saunders, Rowan Noronha, Scott Miller, Vlad Vanzha + more TBA.

Sponsors: Lodestone, Bizby, Toronto TechWeek, Toronto Metropolitan University, The Product Recruiter.

Event hosted by the Toronto Product Management Association.
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Andrea Michalek @thatandream.com · 18/04/2026
I saw this quote today and it kept echoing in my head. Love the life you live. It doesn't have to be a fancy destination or an amazing view. Today, for me, it meant choosing to work from my patio. Birds chirping, little bit of traffic, laptop open. This is enough.
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Andrea Michalek @thatandream.com · 17/04/2026
I'm speaking at Toronto Product Con on May 28. The session: three leadership traps that keep high output teams stuck and what it takes to break the pattern. Are you going? Let me know. I'd love to connect while I'm in town.
Toronto Product Conference listing speakers and details for a session on leadership challenges, scheduled for May 28, 2026.
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Andrea Michalek @thatandream.com · 16/04/2026
Which team are you on right now: shipping features or making markets? Talking about the difference at Toronto Product Con on May 28.
Text highlights the importance of leadership in differentiating teams focused on features versus those creating markets.
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Andrea Michalek @thatandream.com · 22/12/2025
Stop "shoulding" yourself this holiday season. My word for 2026: Adventure. What's yours?
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Andrea Michalek @thatandream.com · 21/12/2025
Three questions for the end of year: → What to START doing? → What to KEEP doing? → What to STOP doing? Be brutally honest.
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Andrea Michalek @thatandream.com · 20/12/2025
This is from my Saturday newsletter. If it resonated, you can subscribe → www.leadershipadvantage.xyz/newsletter
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Andrea Michalek @thatandream.com · 20/12/2025
Your permission slip to NOT do everything between now and January 1st. It's ok for it to be business not as usual.
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Andrea Michalek @thatandream.com · 15/12/2025
Up and to the right is a simplification of what success looks like, but it never plays out that cleanly in reality. I learned, very early on, that the path to your ultimate goal is often the "silly path." It has missteps, turnarounds, and in hindsight, was the harder way to go.
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Andrea Michalek @thatandream.com · 14/12/2025
www.topularstrategy.com/blog/when-t...
topularstrategy.com
When the idea finally clicks
My book didn’t start with an outline. It started with fear. A talk I over-prepared for. And one drawing I couldn’t stop thinking about. That was the moment it became a book I had to write.
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Andrea Michalek @thatandream.com · 14/12/2025
But someone gave me better advice: wait until you have a book burning inside you that you can't not write. I finally found mine. This week's newsletter is the origin story behind Beyond Incremental, and a question for anyone circling something that hasn't clicked yet.
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Andrea Michalek @thatandream.com · 14/12/2025
My book didn't start with an outline. It started with fear. A talk I over-prepared for. And one drawing I couldn't stop thinking about. When I ask other authors if I should write a book, they usually say, "Don't do it."
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Andrea Michalek @thatandream.com · 29/11/2025
If your team can’t move without you… That’s not leadership. That’s dependency. Time to shift.
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Andrea Michalek @thatandream.com · 29/11/2025
I built a course to help you do exactly that. ✅ Communicate vision clearly ✅ Build leadership systems ✅ Lead without being the bottleneck Today’s the last day for Black Friday offers: www.leadershipadvantage.xyz/offers/blac...
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Andrea Michalek @thatandream.com · 29/11/2025
The fix isn’t “better time management.” It’s not blocking out more deep work. It’s shifting from being the keeper of clarity to building shared clarity your team can own.
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Andrea Michalek @thatandream.com · 29/11/2025
Your calendar is full. Your head is foggy. And the irony? Your impact is shrinking even as your responsibilities grow. Especially in December, when planning pressure hits max volume.
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Andrea Michalek @thatandream.com · 29/11/2025
That’s the Context Keeper Trap. You rose fast by bridging gaps and thinking strategically. Now your team leans on you to keep everything coherent. Every update runs through you. Every decision waits for you.
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Andrea Michalek @thatandream.com · 29/11/2025
Burnout isn’t just about working long hours. It’s about carrying all the mental load for your team. You’re not just leading. You’re translating. Explaining. Clarifying. Constantly.
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Andrea Michalek @thatandream.com · 29/11/2025
I thought being the “glue” made me indispensable. Turns out, it made me the bottleneck. A thread for burned-out tech leads stuck in the Context Keeper Trap 🧵
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Andrea Michalek @thatandream.com · 29/11/2025
I'm rebuilding my technical leaders advantage course directly on my website, rather than hosting it separately. Every time I need to set up secret keys for authentication in APIs I feel like I am practicing dark magic. Is that just me? #buildinpublic
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Andrea Michalek @thatandream.com · 28/11/2025
Technical leaders: want to start 2026 with a breakthrough plan? Course + live workshop with me on Dec 10. Black Friday pricing ends Saturday midnight. → beyondincremental.com/offers/blac...
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Andrea Michalek @thatandream.com · 24/11/2025
📌 Enroll in the Technical Leader's Advantage course here: beyondincremental.com/offers/blac...
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Andrea Michalek @thatandream.com · 24/11/2025
Go Beyond Incremental in 2026. Enrollment is now open for my course + live workshop designed for product and engineering leaders who want to break out of reactive mode and lead with clarity. Details below.👇
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Andrea Michalek @thatandream.com · 22/11/2025
Stop drifting into another year. If you’re a technical product leader ready to lead 2026 with clarity, confidence, and momentum: This is your reset. Black Friday access now open. 🕓 Ends Nov 29 🔗 beyondincremental.com/offers/blac...
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Andrea Michalek @thatandream.com · 16/11/2025
I haven’t had that experience. What is your project?
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Andrea Michalek @thatandream.com · 16/11/2025
Clarity Curiosity Customers Camaraderie Coordination Unlock the 5 keys to team success: topularstrategy.com/2022/06/08/...
topularstrategy.com
5 Keys to Product Team Success - Topular Strategy
1. Work that Matters Is your team mission-driven? Can your team answer what the company is trying to achieve and how they get there? At my first startup, I had an offsite where I wrote questions about the company on index cards. I had my developers each pull an index card and respond as if
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Andrea Michalek @thatandream.com · 15/11/2025
The biggest leadership breakthroughs rarely come from adding more tactics. They come from seeing the blind spot you’ve ignored for years, and finally naming it. Take the 5-minute breakthrough leadership assessment, and see where you rank: beyondincremental.com/assessment
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Andrea Michalek @thatandream.com · 10/11/2025
You can chase meaning. Or you can chase money. Or you can do what most high-performers forget: Balance the equation. thatandream.gumroad.com/l/3p
thatandream.gumroad.com
Career Planning Framework
Feeling stuck or uncertain about your next career move?The Career Planning Framework helps you cut through uncertainty and design a career that fits your life - with the purpose, balance, and pay that makes sense for you.This guided workbook helps you clarify: the work that gives you meaning, how you like to spend your days, and the compensation that supports your life.What You'll DiscoverMost career advice focuses on climbing ladders or building skills, and even worse, we often default to what others think success should look like.But the best career decisions come from understanding what you actually need across three essential areas.This framework helps you step back and examine what you really want from your career, so that you can be confident about where you are headed and why.💡 Find Your PurposeWhat makes work meaningful to you?Move beyond generic mission statements to identify the specific impact you want to make and clarify your "why" for showing up each day.🧠 Understand How Y
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Andrea Michalek @thatandream.com · 08/11/2025
The Beyond Incremental framework helps leaders bring together: ✨ People: how you multiply impact ⚙️ Performance: how you turn clarity into results 🔥 Passion: why your work truly matters When these three align, the impossible starts to look inevitable.
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Andrea Michalek @thatandream.com · 08/11/2025
🚀 Big news: BeyondIncremental.com is live. What started as a 48-hour build turned into a two-week evolution: a real-world test of the Breakthrough Leadership Framework. It’s not just a website. It’s a living lab for how leaders create momentum.
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Andrea Michalek @thatandream.com · 03/11/2025
I went back and modified all the commits, and set up my project rules so it doesn’t do it anymore.
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Andrea Michalek @thatandream.com · 03/11/2025
Yep. It does it by default. Crazy, right?
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Andrea Michalek @thatandream.com · 03/11/2025
Do you leave "co-authored by Claude" or your AI tool of choice in your commit messages in git? I'm not. It seems like it might invite IP issues that I don't need. Are others doing the same? #buildinpublic #vibecoding
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Andrea Michalek @thatandream.com · 24/10/2025
Entrepreneurs are not afraid to hustle. There is nothing more fun than seeing a group of potential customers and figuring out how you can serve them. Does that make me an outlier or an adrenaline junkie?
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Andrea Michalek @thatandream.com · 18/10/2025
The higher you rise, the less data you have to make a decision. Being willing to take calculated risks is key. Even if the details are fuzzy, knowing with precision, how you will evaluate a bet is what can help detail-oriented people find their path through uncertainty.
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Andrea Michalek @thatandream.com · 18/10/2025
My daughter picked only a few pumpkins. Still, her wagon was almost too heavy to pull. That moment says everything about leadership. This week’s newsletter: The Pumpkin Problem. Why focus isn’t the fix, and what actually is. leadershipadvantage.xyz/posts/when-...
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Andrea Michalek @thatandream.com · 12/10/2025
Good point Ivan. I agree, looking at the larger scope of impact is appropriate. But, the first step is determining why building something matters, not just because you should check the box.
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Andrea Michalek @thatandream.com · 12/10/2025
Anchoring any technological advance with the human side of leadership is the recipe for making change. Far too many companies have AI as a must-do priority without considering how it positively impacts their customer AND how to serve customers better. AI should not simply be a checkbox to get done
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Andrea Michalek @thatandream.com · 11/10/2025
The worst career moves I've seen (and made) all follow the same pattern: Chasing the bigger title or salary while ignoring what it actually costs. Money looks like freedom. It often buys the opposite.
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