Andrea Michalek
@thatandream.com
🎯 I am a: serial entrepreneur, mom, leadership coach, indie 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
🔥 passions: product management, women in tech, startups, AI, leadership
🚀 my path: developer → CTO → startup CEO → exit → VP PM → brain injury → consultant/coach
Pinned
Andrea Michalek
@thatandream.com
· Jul 24
This year, I've been working on a new book about Breakthrough Leadership.
I've decided to share more as it progresses to get feedback as I write.
Time to #buildinpublic !!!
I've decided to share more as it progresses to get feedback as I write.
Time to #buildinpublic !!!
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
Or you can chase money.
Or you can do what most high-performers forget: Balance the equation.
thatandream.gumroad.com/l/3p
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
thatandream.gumroad.com
November 10, 2025 at 9:26 PM
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
Or you can chase money.
Or you can do what most high-performers forget: Balance the equation.
thatandream.gumroad.com/l/3p
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.
✨ 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.
November 8, 2025 at 7:56 PM
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.
✨ 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.
🚀 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.
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.
November 8, 2025 at 7:50 PM
🚀 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.
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.
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
I'm not.
It seems like it might invite IP issues that I don't need.
Are others doing the same?
#buildinpublic #vibecoding
November 3, 2025 at 10:45 PM
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
I'm not.
It seems like it might invite IP issues that I don't need.
Are others doing the same?
#buildinpublic #vibecoding
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?
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?
October 24, 2025 at 12:50 AM
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?
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?
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.
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.
October 18, 2025 at 8:57 PM
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.
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.
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-...
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-...
October 18, 2025 at 2:46 PM
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-...
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-...
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
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
October 12, 2025 at 3:28 AM
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
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
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.
Chasing the bigger title or salary while ignoring what it actually costs.
Money looks like freedom.
It often buys the opposite.
October 11, 2025 at 5:13 PM
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.
Chasing the bigger title or salary while ignoring what it actually costs.
Money looks like freedom.
It often buys the opposite.
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.
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.
September 30, 2025 at 12:03 PM
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.
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.
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:
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:
September 27, 2025 at 12:00 PM
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:
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:
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):
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):
September 26, 2025 at 12:03 PM
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):
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):
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.
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.
September 25, 2025 at 8:13 PM
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.
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.
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):
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):
September 25, 2025 at 12:02 PM
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):
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):
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)
You spend months writing the "perfect" requirements document, only to watch it become obsolete the moment customers touch the product.
A 🧵: (1/4)
September 24, 2025 at 12:27 PM
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)
You spend months writing the "perfect" requirements document, only to watch it become obsolete the moment customers touch the product.
A 🧵: (1/4)
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/
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/
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.
leadershipadvantage.xyz
September 23, 2025 at 7:53 PM
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/
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/
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?
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?
September 23, 2025 at 12:20 PM
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?
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?
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.
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.
September 22, 2025 at 9:30 PM
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.
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.
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.
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.
September 20, 2025 at 12:02 PM
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.
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.
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?
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?
September 17, 2025 at 12:00 PM
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?
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?
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 🧵
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 🧵
September 15, 2025 at 8:13 PM
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 🧵
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 🧵
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.
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.
September 15, 2025 at 2:27 PM
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.
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.
🔥 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)
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)
September 14, 2025 at 12:04 PM
🔥 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)
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)
Are starter packs still a thing?
I am getting new followers, but engagement seems way down for me here.
Is it just me?
I am getting new followers, but engagement seems way down for me here.
Is it just me?
September 13, 2025 at 2:25 PM
Are starter packs still a thing?
I am getting new followers, but engagement seems way down for me here.
Is it just me?
I am getting new followers, but engagement seems way down for me here.
Is it just me?
“What went right?” feels safe. Safe is why most teams never break through.
Feature factories stop there.
Breakthrough teams go deeper.
They ask:
Feature factories stop there.
Breakthrough teams go deeper.
They ask:
September 13, 2025 at 11:57 AM
“What went right?” feels safe. Safe is why most teams never break through.
Feature factories stop there.
Breakthrough teams go deeper.
They ask:
Feature factories stop there.
Breakthrough teams go deeper.
They ask: