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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
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
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
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
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
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
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
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
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
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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Andrea Michalek @thatandream.com · 30/09/2025
Inner Circle starts Oct 1. A small group of leaders will learn how to fuel grit and strategy with joy so their teams do not just deliver, they love the climb. Only a couple seats left. If you have been on the fence, this is your moment. DM me to join.
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Andrea Michalek @thatandream.com · 27/09/2025
I learned poker before I was 10. Sitting next to my dad, uncles around the table, watching them bet, bluff, fold. It looked like luck. It wasn’t. Poker is discipline. It’s knowing when to play small, when to fold fast, and when to raise big on a strong hand. I learned:
I learned poker before I was 10.  Sitting next to my dad, uncles around the table, watching them bet, bluff, fold.  It looked like luck. It wasn’t.  Poker is discipline.  It’s knowing when to play small, when to fold fast, and when to raise big on a strong hand.  That lesson shows up in product building every day.  • Fold bad bets fast. Every time you don’t, you’re stealing chips from your breakthrough.  • Decisions aren’t all-in moments. They’re hands to play, fold, or raise.  • Momentum comes from taking shots, not waiting on the perfect hand. Most teams burn out because they treat every decision like an all-in moment.  The pros stay alive long enough to catch the right hand.  Product is the same game.
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Andrea Michalek @thatandream.com · 26/09/2025
The Execution Trap: When Activity Masquerades as Progress You lock teams into rigid, long-term plans that collapse the moment the market shifts. You chase the "perfect launch" instead of shipping small, learning fast, and adapting. A 🧵 (1/4):
**The Execution Trap: When Activity Masquerades as Progress**  You lock teams into rigid, long-term plans that collapse the moment the market shifts.  You chase the "perfect launch" instead of shipping small, learning fast, and adapting.  It feels productive. Everyone's busy.  But while you're marching toward a grand reveal, the market has already moved.  **The antidote:** Operating Rhythm → Design cycles that force rapid testing of new ideas → Ship small experiments before competitors ship full products  Make learning your habit, not your afterthought.  What will you experiment with this quarter instead of over-planning?
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Andrea Michalek @thatandream.com · 25/09/2025
46% of workers sit through 3+ meetings a day. That is 11+ hours a week lost. It kills energy. It kills joy. In Inner Circle I show leaders how to reclaim that time with PACE: async updates, focused meetings, more joy. We start Oct 1. Seats almost gone. Reply if you want in.
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Andrea Michalek @thatandream.com · 25/09/2025
The Measurement Trap: When Data Lies You celebrate downloads, signups, and dashboards full of green arrows while ignoring whether customers actually get value. You spend 6-12 months building, then discover the market doesn't care. A 🧵 (1/4):
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Andrea Michalek @thatandream.com · 24/09/2025
The Analysis Trap: When Perfect Planning Kills Progress You spend months writing the "perfect" requirements document, only to watch it become obsolete the moment customers touch the product. A 🧵: (1/4)
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Andrea Michalek @thatandream.com · 23/09/2025
Most product leaders are trapped. You battle bottlenecks instead of building acceleration. You manage stakeholder resistance instead of building momentum. Start building breakthrough systems instead. Subscribe to the Beyond Incremental Newsletter: leadershipadvantage.xyz/
leadershipadvantage.xyz
Beyond Incremental Newsletter
Weekly frameworks to build team acceleration, natural authority, and category creation. For product leaders ready to become breakthrough leaders, not just better ones.
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Andrea Michalek @thatandream.com · 23/09/2025
The Performance Paradox: Your best intentions are sabotaging breakthrough results. You need to innovate faster, but you're trapped in systems that demand certainty for breakthrough decisions. What performance trap is quietly killing your breakthroughs?
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Andrea Michalek @thatandream.com · 22/09/2025
7 Subtle Ways High-Performing Teams Accidentally Kill Breakthroughs 1. The longer you plan, the less relevant your plan becomes. 2. The more stakeholders you add, the less bold your ideas get. 3. Vanity metrics give the illusion of progress.
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Andrea Michalek @thatandream.com · 20/09/2025
I built my career on grit and strategy. But real breakthroughs came when joy was in the room and my team enjoyed the climb. That is why I created Inner Circle: coaching for leaders who want teams that thrive while they deliver. We kick off Oct 1. Limited spots. DM me to join.
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Andrea Michalek @thatandream.com · 17/09/2025
If you can win Zoom Bingo before lunch, imagine what your team could do with half those hours back. Most meetings should be an email. But the real fix is finding the right operating rhythm. If Zoom Bingo feels too easy, your rhythm needs work. Where would you start fixing it?
If you can win Zoom Bingo before lunch, imagine what your team could do with half those hours back.  **Most meetings should be an email.**  But the real fix is finding the right **operating rhythm.**  That’s where **PACE** comes in:  - **P**urposeful outcomes - **A**sync-first - **C**ustomer connected - **E**scalation boundaries  Cutting meetings gives you hours back.  PACE gives you momentum forward.  **If Zoom Bingo feels too easy, your rhythm needs work. Where would you start fixing it?
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Andrea Michalek @thatandream.com · 15/09/2025
I built my career on grit and strategy. But the biggest breakthroughs came when joy was in the room, and my team actually enjoyed the climb. Early in my leadership journey, I championed 3 principles: • Improve Effort to Effect Ratio • Bring Ideas to Reality • Have Fun A 🧵
I built my career on grit and strategy.  But the biggest breakthroughs came when joy was in the room, and my team actually enjoyed the climb.  Early in my leadership journey, I championed 3 principles:  - Improve Effort to Effect Ratio - Bring Ideas to Reality - Have Fun  That third one? I'd completely lost sight of it.  This weekend, reconnecting with old friends reminded me of something powerful.  The best conversations happened when we were laughing.  The deepest connections formed when joy was in the air.  Yet as I've been building my practice coaching product leaders, I realized I wasn't practicing what I preached.  I was so focused on delivering results that I forgot to make my own journey enjoyable too.  Here's what I know: optimists consistently outperform pessimists. Data backs this up.  And my proudest career moments happened when I approached challenges with genuine joy.  The best product teams I've worked with don’t just deliver great outcomes.  They enjoyed the journey.
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Andrea Michalek @thatandream.com · 15/09/2025
The metrics that matter for competitive advantage: Leading • Costly behavior shifts • Exclusive partnerships • Compounding data Lagging • Market share • Win rates • User growth The strongest companies measure what competitors can’t copy, not what they can count.
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Andrea Michalek @thatandream.com · 14/09/2025
🔥 Hot take: Being the go-to person is overrated. If you’re indispensable, you’re not promotable. Leaders don’t get noticed for doing everything. They get noticed for setting direction. I had to learn this the hard way. A 🧵 (1/8)
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Andrea Michalek @thatandream.com · 13/09/2025
Are starter packs still a thing? I am getting new followers, but engagement seems way down for me here. Is it just me?
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Andrea Michalek @thatandream.com · 13/09/2025
“What went right?” feels safe. Safe is why most teams never break through. Feature factories stop there. Breakthrough teams go deeper. They ask:
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Andrea Michalek @thatandream.com · 12/09/2025
Being indispensable feels flattering. But when every decision runs through you, you have not scaled leadership. You have scaled dependency. The Context Keeper Trap looks like value, but it creates fragility. This week, I share the three shifts to escape it.
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