Maya Grossman 💪 Career Success Coach

I will make you VP | Executive Coach and Corporate Rebel | 2x VP Marketing | Ex Google, Microsoft | Best-Selling Author

Hey, I'm Maya 👋
At the age of 27 I hit rock bottom - I completely burnt out trying to overwork my way into a promotion. 
Fast forward 15 years and I gained 10 promotions, worked for companies like Microsoft and Google, landed two VP roles at hyper growth startups, earned high six figures and actually enjoyed my 9-5.

What changed?
I stopped letting my career happen to me, and instead started managing it like a business.
I learned what it really takes to break through to executive roles, stopped making the mistakes that were holding me back, and developed the executive skills that got me noticed.

Today I am an executive career coach and my goal is to help you demystify what it takes to break through to executive roles, and build the bridge between where you are today, and where you want to be in your wildest dreams.

I want to save you the time, effort, and headache of figuring it out on your own and give you the playbook for achieving anything you want in your career.

My mission? To empower 1,000,000 high achievers to build the career of their dreams.


My brag list:

→ International best-selling author. Ranked  #1 new release for career books on Amazon.

→ 150,000+ followers across platforms, 70M views for my daily career advice
 
→ LinkedIn instructor (34,000 + learners, 4.7/5)

→ Named top 50 rising experts (US) and top 12 in Austin in 2023

→ Coached hundreds of high achievers to success on their terms​


If you are ready to level up in your career:

JOIN MY WEEKLY NEWSLETTER: Become VP Ready in 10 Minutes Per Week

Win the corporate game in 2025. Join 50,000+ high achievers receiving weekly actionable guides and proven strategies to level up into executive roles in months not years. 

www.mayagrossman.com/email


SUCCESS BUILDERS: BECOME THE OBVIOUS VP - 3-MONTHS GROUP COACHING PROGRAM

The exact steps to level up from Director to VP in months not years, without an MBA or working 80/h weeks

www.mayagrossman.com/SB


PRIVATE 1:1 COACHING

For senior executives who want to become first time VPs, or crush their first VP role.
I only offer 5 spots quarterly, and they require a 6-months commitment.

DM me for details.

Founder, Maya Grossman Consulting

Maya Grossman

You’re not too quiet.
You’re just being careful and it’s costing you visibility.

If you’ve ever held back in a meeting because you didn’t want to come off as “too much,” this is for you.

You don’t need to be louder. You need to be clearer.

Try this line next time you have a strong POV:
“I see it a little differently, can I walk you through my thinking?”

It signals confidence, respect, and strategic thinking, all without raising your voice.

You don’t get promoted for being agreeable.
You get promoted for leading conversations, not tiptoeing around them.

What’s one phrase you use to speak up with authority? Drop it below.

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Here is the link to the episode:
https://open.spotify.com/episode/6ebCBzi8Hi0uem5UHtzfcZ

This conversation is what happens when two former executives spill the best kept secrets about what it really takes to level up. 

I stopped getting more stuff done at work.
And that’s when my career finally started to move.

For a long time, I thought growth came from being helpful.

Saying yes.
Fixing problems.
Taking on work outside my role.

I was a marketer.
But I was also helping IT, managing company events, and responding to every “can you help with this?” request that came my way.

I was busy all the time.
Exhausted.
And still not getting pulled into bigger conversations.

What I didn’t understand at the time was why all that effort wasn’t translating into bigger opportunities.

The moment everything changed wasn’t burnout.

It was watching other people get promoted.

They weren’t working longer hours.
They weren’t saying yes to everything.

So I started paying attention.

They didn’t jump in to fix everything.
They talked about their thinking, not just what they delivered.
They were selective and intentional with their time.

So I tried it.

I stopped rescuing.
I stopped saying yes by default.
I stopped proving my value through output alone.

And it felt uncomfortable.
It went against everything that had worked for me before.

But here’s what surprised me.

No one thought I was less committed.
No one questioned my value.

Instead, people asked for my opinion.
They pulled me into conversations earlier.
They treated me differently.

That’s when it clicked.

At senior levels, doing more doesn’t help you stand out.
It just keeps you busy.

If you’re delivering results and still not moving up, the answer probably isn’t more effort.
It’s a different way of showing up.

What’s one thing you’ll stop doing to break the cycle?

I stopped getting more stuff done at work

Why Directors in tech get stuck before VP ⬇️

Directors who want a VP role often make the same quiet mistake:
They give updates instead of opinions.

That signals one thing to leadership:
“I execute well but I don’t own decisions.”

You can be sharp.
You can be polished.
You can be delivering real results.

And still disqualify yourself from the room where direction is set.

Because if leadership only hears what happened and never what you think should happen next, they won’t see you as VP-ready.

They’ll see you as dependable execution.

The shift isn’t louder communication.
It’s higher-altitude thinking.

Comment VP and I’ll send you a free masterclass where I break down how to move from reporting work → being trusted with decisions.

Watch how quickly the conversations around you change.

Most people getting passed over for VP are not underperforming.
They're over-performing at the wrong level.

These are the doer habits that look impressive on paper but quietly stall your promotion:

- Saying yes to everything (a.k.a people pleasing)
- Waiting for permission
- Presenting options instead of making calls
- Over-explaining to prove credibility
- Solving problems only inside your lane
- Only offering insights when asked

The truth is none of these are "bad habits."

They're rewarded early in your career.

But at senior levels, they send a very clear signal:
"You're reliable execution. Not leadership judgment."

VPs are not promoted because they do more.
They're promoted because they decide better.

They choose where to focus.
They make calls with incomplete data.
They connect dots across the business.
They influence outcomes without owning every task.

That's why burnout is so common right before the VP leap.

You're carrying Director-level work with doer-level habits.
Not good.

If you want to learn how to retire doer habits and start showing up as an executive decision-maker, I'm breaking it down step by step in my free masterclass.

Comment VP and I'll send you the details.

And yes, this is the work that actually changes how leaders see you.

P.S. How many of these are you still doing without realizing it?

6 Doer Habits That Kill Promotions

If you feel overlooked, there’s a good chance you’re selling yourself short.

Right now, there are people getting noticed, pulled into bigger conversations, and promoted
while doing a fraction of the work you’re doing.

They’re not smarter.
They’re not working harder.
They’re not delivering better results.

They’re just better at communicating their impact.

Meanwhile, many high performers talk themselves out of visibility with thoughts like:
“It’s just my day job.”
“It’s not that impressive.”
“I didn’t 10x anything.”
“I was just doing what I was supposed to do.”

That mindset is quietly killing your leverage.

Here’s the shift I want you to make:

Stop evaluating your work based on effort.
Start evaluating it based on impact.

Two questions to ask yourself about anything you’re working on:

1. What did this make easier, faster, cheaper, or better for the business?
2. And what would have happened if I hadn’t stepped in?

If you’re thinking, “But my work isn’t quantifiable,” let me give you a real example.

One of my clients, we’ll call her Natalie, works in finance.
Part of her role was producing a monthly report for leadership.

When she inherited the process, it required:
three people
working three full days
every single month.

It drove her crazy.

So she redesigned the process.

The result?
The same report now takes one person two hours.

At first, she described this as:
“Oh, I improved the process.”

No one cared.

Then she learned to quantify it.

This new system will save us roughly three full months of work this year,
which frees up budget for an additional headcount
and allows the team to focus on higher-impact work.”

Same work.
Different framing.
Completely different perception.

If you’re not being recognized, don’t assume your work isn’t valuable.
Ask whether you’re underselling it.

Because the people getting ahead aren’t always doing more.
They’re just making the value of what they already do impossible to ignore.

♻️ Share with someone who needs to stop underselling themselves

Let me normalize something about senior leadership.

I didn’t get to VP by being perfect.

In fact, I’ve made mistakes that cost companies hundreds of thousands of dollars.

I’ve backed the wrong campaigns.
Missed targets.
Made bets that set teams back months.

I’ve walked into senior leadership meetings confident... and then completely frozen.

Once I literally couldn’t get a single word out.

I’ve missed deadlines I owned.
I’ve mishandled people.

Not because I didn’t care, but because I didn’t yet know how to lead at the level the role required.

I’ve lost my temper.
I’ve gotten into real fights with my CEO.

None of that looks great on a highlight reel.

But these screw-ups taught me the most.

But here’s what people don’t tell you early in your career.

Executives are not the people who never mess up.

They’re the people who learn how to recover, take ownership, and make better calls next time.

Those mistakes taught me:

- How to make decisions with incomplete information
- How to stand back up after public failure
- How to repair trust when you’ve damaged it
- How to lead people when you don’t have all the answers yet

Perfection never made anyone VP.

Judgment did. Accountability did. Growth did.

If you’re waiting to feel flawless before you aim higher, you’re playing the wrong game.

I break down how senior leaders actually develop this judgment, without burning themselves out or pretending they’ve never failed, in a short, pre-recorded masterclass: https://lnkd.in/gG8GnY4Y

The difference between a Director and a VP isn’t strategy.
It’s where they spend their energy.

A Director puts their energy into getting things done.
A VP puts their energy into shaping what gets done and how.

That took me a long time to learn.

Early in my career, I genuinely believed my value came from output.

From doing more.
From being indispensable in execution.

Spending time thinking, networking, or stepping back to shape direction felt irresponsible.

Almost lazy.

If I wasn’t doing, how was I adding value?

I see the same belief with a lot of high achievers.

They assume that if they stop being the one who carries everything, they’ll matter less.

The opposite is true.

The Director:

→ Jumps in to solve problems
→ Personally drives key initiatives
→ Fixes issues when things go sideways
→ Is deeply involved in execution
→ Becomes the person everyone relies on

They’re effective.
They’re trusted.
They’re also at the center of everything.

The VP:

→ Decides what deserves attention and what doesn’t
→ Sets direction before problems show up
→ Builds leaders who can make calls without escalation
→ Creates clarity so execution happens without them
→ Is comfortable not being in the middle

Here’s the shift that changes how you’re seen:

Directors add value by doing.
VPs add value by deciding.

What to prioritize.
What to deprioritize.
What tradeoffs to accept.
What problems not to solve.

Letting go of “doing” doesn’t make you less valuable.

It makes room for the kind of value senior leaders are actually looking for.

That’s when the conversation changes.

And if you’re not sure what they’re looking for in a VP, I break it down here: https://lnkd.in/gG8GnY4Y

Never take a promotion without a raise sounds smart. 
It isn’t

On the surface, it feels like a strong boundary.
It sounds fair.

But it also ignores how leverage actually work.

Of course, in a perfect world, more responsibility comes with more pay.

And long term, I don’t want anyone doing expanded work without compensation.

But...
If you’re offered a promotion without an immediate raise, the real question isn’t:

“Is this fair?”

It’s:
“What does this unlock?”

Because a few things matter here.

First, momentum.
When leaders offer you a promotion, they’re moving forward.

If you say no, the odds of them coming back later are low. 
They don’t sit around waiting.

Second, signal.
The title, scope, and visibility change how you’re seen.

Internally and externally.

That signal is powerful.
Especially if you want to get a new job that pays your worth instead of moving latterly. 

Third, leverage.
Once you’ve operated at the higher level for a few months,
you’re no longer negotiating as who you were.

You’re negotiating as the leader you’ve already proven yourself to be.

That’s going to unlock 5 and 6 figure raises.

This is how senior leaders think.

Not, “Is this fair today?”
But, “What does this position me for next?”

The mistake isn’t taking a promotion without a raise.
The mistake is taking it without a plan.

“Never take a promotion without a raise” sounds smart on the internet.
In real careers, it’s incomplete advice from people who don’t think past the next paycheck.

Senior leaders don’t win by waiting for fair.
They win by being strategic.

P.S.
The people who use this strategy don’t stay underpaid for long.

“I want to move from Director to VP, so I’m focusing on job search.”

Every time I hear this, my heart sinks.
Because I know what usually follows.

Resume updates.
Applying on LinkedIn.
Waiting to be picked.
Hoping a new company will change how you’re seen.

That’s the lie we tell ourselves to stay comfortable.

Calling it “job search” makes it feel familiar.

Like there’s a clear process.

But moving from Director to VP is rarely a job search problem.

It’s an identity shift.

VP roles aren’t won by resumes.
They’re won by positioning, credibility, and presence.

The people making the decision have to see you as ready.
And no amount of keywords can replace that.

Last year we’ve had 15 client promotions.

More than half were leaders leveling up while changing companies and getting new jobs.

None of them applied online.
None of them updated their resume 23 times.

They followed a different strategy:

They got clear on their VP-level value.
They learned how to talk about it strategically.
They pressure-tested it with successful VPs.
They built real relationships with senior leaders.
They showed up as peers, not candidates.

And got the job even though their resume said “Director”.

One client reached out after 8 months of “job search.”

No traction. No momentum.

She was ready to give up and move latterly.
But instead we changed the strategy.

We worked on her positioning.

Her story.
Her network.
Her presence.

A few months later, she landed her first VP role.

Because it was never about job search.

It was about becoming ready.

I talk about this all the time and yet...

So many high achievers still choose the same “job search” approach
and stay stuck.

That’s the part that breaks my heart.

Because their effort isn’t the issue.
Their talent isn’t the issue.

The strategy is.

If you’re a Director aiming for VP and all you’re doing is applying
you’re playing the wrong game.

There are 3 shifts that position you as VP-Ready and you can learn all of them in the next 25 minutes.

Start here: https://lnkd.in/gG8GnY4Y

"She can handle anything" is not a compliment.

It feels flattering.
It also keeps people stuck.

Let me tell you about a client - I'll call her Lina.

Every big, messy initiative eventually landed on her plate.

New product launch that slipped three times?
Lina will fix it.

Cross-functional project with fifteen stakeholders and no owner?
Lina will take it.

Leader going on parental leave, team in chaos?
Lina can step in.

Her reputation was simple:
"She can handle anything."

Then promotion season came.

Her VP said the words that cut the deepest:
"You're incredible. I don't know what we'd do without you. Let's revisit promotion next cycle."

She was everywhere, doing everything...
and still not seen as "ready for more."

When we unpacked it, the pattern was obvious:

She was solving everyone’s problems, not driving her own charter
Her impact stories were about rescue missions, not business outcomes
Leaders were afraid to move her because she was too useful where she was

Sound familiar?

If the story people tell about you is "we would fall apart without them,"
it feels like praise.

But it's actually a trap.

Here's the reframing exercise I gave Lina.
Do it yourself this week:

Write down three major projects you led in the last 12 - 18 months.

For each one, answer:

1. If I vanished tomorrow, what measurable result would disappear with me?
2. How did this project change the business in ways leaders actually care about?

Now rewrite your story of the project using only those answers.
Not the chaos you survived.
Not the hours.
Not the crisis management.

Your goal is to shift from:
"I held everything together"
to
"I moved this metric and this outcome."

That is the language of VP decisions.

If you want to learn how to take the work you're already doing and turn it into a real promotion case, I cover it in my free masterclass: https://lnkd.in/gG8GnY4Y

Becoming a VP wasn’t about confidence first.
It was about action first.

Every career-changing move I made felt uncomfortable when I made it.
Asking for feedback I wasn’t sure I could handle.
Being explicit about my ambition.
Letting go of work I was good at so I could take on work I wasn’t.

None of that felt “ready.”
All of it changed my trajectory.

If you are doing excellent work but still waiting to be seen as VP material, this is your sign to stop waiting.

I teach exactly how to make these moves without burning bridges or blowing up your reputation inside my free masterclass: https://lnkd.in/gG8GnY4Y

Rating the hard things I did to become a VP

When I first started working on my executive presence
I made the same mistake most high achievers make:

I thought it meant becoming someone else.
I tried sounding more polished.
Rehearsed every sentence.
Softened my personality so I could “fit” the leadership mold.

And it was miserable.

I kept thinking,
“If I can just act like a typical exec, maybe they’ll finally take me seriously.”

But all it did was make me frustrated, disconnected, and tired.
Because executive presence isn’t about faking polish.

It’s about learning to lead as yourself.
With clarity, conviction, and impact.

My turning point wasn’t some glamorous leadership epiphany.

It was burnout.

The kind where you’re lying on the floor wondering why you’re trying so hard to be someone you’re not.

That’s when I made a decision:
If the only path to leadership required pretending, I didn’t want it.

So I stopped performing and started aligning.

I leaned into the strengths that were already there:

→ Direct communication
→ Real, trusting relationships
→ Calm when things went sideways
→ Clear strategic thinking instead of jargon

I wasn’t the “typical” executive and that’s exactly why things started working.

Once I showed up as myself with presence, not pretense, everything shifted:

→ Two VP roles
→ A high six-figure salary
→ Teams who trusted me
→ Leaders who backed me

Because when I communicated with clarity instead of corporate-speak,
and led with authenticity instead of acting...

People finally saw what I actually brought to the table.

Here’s the real lesson:
Executive presence isn’t a costume.
It’s embodied leadership.

And the moment you stop trying to fit in?

You finally stand out.

If you’re wondering: Am I making this mistake? Watch this 25 min breakdown to get your answer: https://lnkd.in/gG8GnY4Y

My nervous system used to run my career. Now, I run it.
Because I started doing these 3 things (and you can too):

For years I thought I needed more skills to get promoted.

More training. More experience. More credentials.

But the truth was surprising:
I didn't rise just because my capability expanded.

I rose because my capacity did.

I could lead a team.
I could deliver results.

But in the moments that mattered most, my body shut me down.

My voice shook when I needed it steady.
My mind blanked in front of senior leaders.

I stayed quiet in rooms where I should have owned the conversation.

Not because I wasn't ready.
But because my nervous system was in overdrive.

Once I understood that, everything changed.

Here are the 3 practices that helped me step into real executive presence:

1. I trained myself to sit in discomfort instead of escaping it
I used to avoid anything that made my chest tighten or my stomach drop.

Now I sit with it for 60 seconds.

No fixing. No distracting. Just noticing.

This built more emotional strength than any leadership course I ever took.

Try this:

Next time discomfort shows up, pause for 60 seconds.
Name it.

"This is activation."
"This is freeze."

Naming reduces intensity instantly.

2. I rewrote the story my body was telling me
Same physical signals. New interpretation.

Old thought: my heart is racing so something is wrong.
New thought: my heart is racing because my body is preparing me.

Same sensation. 

Completely different outcome.

Try this:
Before a high stakes moment, tell yourself:
"I am not nervous. I am preparing."

Elite performers do this for a reason. It works.

3. I asked one question before every brave action
Fear used to make every decision for me.

Until I started asking:
"What would the leader I am becoming do right now?"

Not the stressed version of me.
Not the overthinking version.

The future version.

That question changed how I spoke, how I led, and the risks I was willing to take.
It changed my career trajectory more than any skill I ever mastered.

Try this:
Use that question once a day.
Let future you lead the moment.

Skills matter.

But capacity decides whether you can use them when it counts.

If this hit you in the gut, save this post and use it.
If you are ready to lead at a higher level, follow me. I teach this every week.

You already have the skills.
If you want help building the capacity to use them when it counts, I put everything I teach my clients into a 25-minute session you can watch on demand. No fluff, just the framework: https://lnkd.in/gG8GnY4Y

She came to me saying she wanted to get to VP.

Her plan sounded familiar:
Take on more projects.
Say yes more often.
Be the person who always delivers.

On paper, it looked like ambition.

So I asked her a question most high performers never stop to ask:

“What do you want to feel differently once you’re a VP?”

She didn’t say “busier.”

She said:
“I want my opinion to matter.”
“I want to influence decisions, not just execute them.”
“I want my work to actually move the business, not just keep it running.”

Then I asked the uncomfortable follow-up:

“Will doing more work get you that?”

She already knew the answer.

No.
It would make her reliable.
Not influential.

We scrapped the ‘more work’ strategy and rebuilt around what VPs are actually paid for:

• Fewer initiatives, bigger stakes
• Clear points of view, not endless updates
• Ownership of outcomes, not tasks

What changed?

She wasn’t working less hours.
She wasn’t coasting.

But she was:
• Asked for recommendations instead of status
• Brought into decisions earlier
• Trusted to shape direction, not just deliver

She told me:
”This is the first time my work feels like it matters at the top”

That’s what happens when you follow the right strategy.

Not more work.
More impact.
More influence.
More fulfillment.

If your promotion strategy is still “do more,” you’re optimizing for the wrong outcome.

Before you take on one more project, ask yourself:

“Will this actually increase my impact?”

Then build your promotion strategy around it.

If you’re not sure where to start, I’ve got you.
Start here: https://lnkd.in/gG8GnY4Y

“My wife says I’m a different man.”
That’s what one of my clients told me last week.

Not because he got a shoutout from the CEO.
Not because the executive team finally sees him as executive material.
Not even because, after three years of waiting, the promotion is finally on the books.

Those things matter.

But that’s not the real transformation.

The real shift was this:

He stopped showing up like someone hoping for a chance.
He started showing up like someone who creates his own.

More confident.
More positive.
More strategic.
More grounded.

A different man.

And here’s what I want people to understand:

My program doesn’t give you a short-term confidence bump.

It doesn’t hype you up for 13 weeks and then drop you back where you started.

It rewires how you think.

How you lead.
How you see yourself.

Because career growth isn’t about learning tactics.

It’s about becoming the person who naturally gets the opportunities everyone else waits for.

This client walked in believing his next decade would look just like the last.

He walked out with executive recognition, a promotion in motion, and a completely different identity.

And that doesn’t fade.

That stays.

If you want external change, you need internal transformation.

That’s the work we do.

Want to take the first steps? Start here: https://lnkd.in/gG8GnY4Y

My client just added $216K to her OTE with one conversation.

And it was the one she really didn’t want to have.

There was no bidding war.
No dramatic standoff.
No leverage from multiple offers.

Just one clear, uncomfortable conversation negotiating the first offer.

Here’s what actually made it work:
This wasn’t about negotiation tactics.
It was about executive confidence.

At the VP level, avoiding hard conversations is a liability.

You’re expected to ask for what you want, hold boundaries, and stay grounded under pressure.

She walked in clear on three things:

1. What she wanted.
Not what sounded reasonable. What she actually wanted.

2. Her red lines.
Knowing exactly where she would and wouldn’t compromise removed the emotional noise.

3. Her proof.
When confidence wobbles, facts don’t. Scope, results, impact.

This is the part most people miss.

If you can’t advocate for yourself and ask for what you want you’re not signaling executive readiness yet.

Negotiation isn’t a special event.
It’s part of the job.

This is what executive confidence looks like in real life.
Not louder. Not aggressive.
Clear, grounded, and willing to have the conversation most people avoid.


P.S.
Not knowing how to advocate for yourself is a leadership skill gap that eventually shows up in your title, scope, and pay. But... anyone, and I mean anyone, can learn it.

I break it down in a free 25-minute training: https://lnkd.in/gG8GnY4Y

No one tells you how your life actually changes when you become a VP.

Everyone talks about the title.
The salary.
The scope.

The biggest shifts are the ones no one sees on LinkedIn.

One client, Shawna, told me she had never been more confident in herself.
Not in a loud way. In a grounded way.

She said it felt like she rediscovered who she really was.

That confidence didn’t just change how she showed up at work.
It opened doors everywhere in her life.
(Including with her daughter)

Another client, Vincent, said something that warmed my heart.
He told me his wife said he is “a completely different person”.

Not because his job changed overnight, but because he stopped doubting what he was capable of.

He learned how to trust himself under pressure.
How to stand behind his decisions.
How to stop shrinking in moments that mattered.

And then there’s the client who negotiated a six-figure increase to her total compensation and told me,
“I will never sell myself short again.”

That sentence matters more than the number.

These are the changes people don’t talk about.
They don’t show up in announcements or job updates.

But this is how real change happens.

Becoming an executive isn’t just about getting the role.
It’s about who you become in the process.

It’s about stepping into the most capable, grounded, confident version of yourself.

That version changes your career.
And it changes your life.

That’s the business I’m in.

I recorded a short masterclass on what actually changes when you step into senior leadership, beyond the role itself: https://lnkd.in/gG8GnY4Y

Meet Ryan. Not his real name, but his story is very real.
He joined my program with one clear plan: get promoted.

Six weeks later there were layoffs.

Suddenly the question wasn’t “How do I get promoted?”

It was “What the hell do I want next?”

And “How do I get it before my family spirals into panic?”

Here’s the part most people won’t admit out loud:

Ryan had spent years as a Director... quietly hoping the VP job would just find him.

He had a great reputation.
A strong network.
A track record that could go toe-to-toe with any VP.

But he never actually declared what he wanted.

Not to himself.
Not to other people.
Not even in his networking conversations.

So guess what his network sent him?

Director roles.
Mid-level roles.
“Safe” roles.

Nothing he actually wanted.

Months passed. His family got anxious. He got anxious.

He started interviewing for Director positions just to make the stress stop.

And then something interesting happened.

Multiple interviewers told him

“You’re overqualified. You should be going for VP.”

That was the moment.

He had to admit to himself what everyone else already saw.

He was ready.

He was just scared.

So he made a decision.

Not “I hope something happens.”
Not “Maybe someone will pick me.”

But: I’m done compromising. I’m going after the job I actually want.

And then he backed it up with action.

- He put himself into real rooms
Community events. Industry meetups. Conferences.

- He built social proof
One thoughtful LinkedIn post a week. Nothing fancy. Just credibility in public.

- He doubled down on strategic networking
Not “catching up with old contacts.”

Actual conversations with leaders doing interesting work.

Peers. Founders. CEOs.

People who open doors that don’t exist yet.

But the biggest shift?

He stopped panicking about not having a job.
He stopped trying to force the next step.
He finally relaxed into the identity he’d been avoiding.

And then something happened that still makes me smile.

On his way to a short vacation, he got a call.
From someone he’d met six months earlier.

“Are you free to meet our CEO? We think you’re the person we need.”

There was no job posting.

No hiring plan.
No formal search.

One meeting later: VP offer.

At a company on the verge of doing groundbreaking work in his field.

When I asked him if the wait was worth it, he laughed.

“Hell yes. I’d do it again. I’d just take action faster next time.”

Here’s the truth his story teaches:
Even in a brutal job market, opportunity shows up fast when you show up first.

He didn’t manifest it.

He created it.
He positioned himself for VP.
He built visibility.
He expanded his network beyond comfort.
He took action when it felt terrifying.

And he landed his dream role.

If you’re a Director sitting on VP-level experience but waiting for permission

2026 is not the year to play small.

Stop hoping. Start positioning. Opportunities follow visibility.

There’s a very specific version of “executive” we’re all taught to copy.

Formal.
Distant.
Buttoned-up.

Careful with words.
Careful with people.
Careful with opinions.

I tried that version early in my career.

And it never felt like me.

So I did the opposite.

I wore jeans and a t-shirt.
I knew my team deeply, personally, humanly.
I said what I actually thought instead of dressing it up in jargon.
I moved fast when things felt slow and political.

I didn’t wait to be “ready” before deciding what I wanted next.

And yes, that made some traditional corporate executives flinch.

But here’s what surprised me:

I didn’t lose credibility.
I gained it.

Because leadership isn’t about fitting a mold.

It’s about trust. Judgment. Clarity. Results.

I didn’t become a VP by changing who I was.
I became a VP by owning who I was and letting my leadership speak for itself.

That’s the part no one tells you.

If you think you need to become more polished, more corporate, more performative to get promoted... you don’t.

I break this down in my free masterclass:
how promotions actually work, how perception really shifts, and how to lead at the next level without selling out your personality.

https://lnkd.in/gG8GnY4Y

Things I did as a VP that will make traditional corporate executives run for the hills 

For years, I avoided self-promotion.
Because the only version I’d seen was:
Loud, ego-driven, and inauthentic.

And I didn’t want to be that person.

So I did the opposite.

I kept my head down.
Let my work speak for itself.
Assumed results would be enough.

They weren’t.

Avoiding self-advocacy didn’t make me humble.
It made me invisible.

And I learned very quickly that invisible people don’t get promoted.

The turning point was realizing there was another way.
I didn’t need to brag or sound cringe worthy.
I could frame my impact in a way leaders actually understand it.

Once I figured it out - it was like magic.
I turned everyday moments into mini self promotion opportunities.

- Meetings
- Emails
- Slack
- 1:1

And by dropping small self advocacy hints all the time...
My trajectory changed without me becoming someone else.

If self-promotion makes you uncomfortable,
the problem isn’t that you’re bad at it.

It’s that no one taught you a better way.

Let’s change that: https://lnkd.in/gG8GnY4Y

Avoiding self

Graduate corporate life for entrepreneurial freedom — without jeopardizing your income or family 💚 | Pod: UncageYourself.FM 🎧

Directors. VPs. Executives.
Ready to go Corporate → Founder in ONE Year?

This is the smart path out — without blowing up your life.

We help corporate veterans turn their employer into an investor, compress their job by 50%, and launch a 1-of-1 premium business.

Corporate becomes a short-term asset — not a lifelong trap.

The system is called Corporate Graduation™.
And it works.

You’ve built a strong corporate life. But you’re likely facing 2+ of these:

1) Your time isn’t yours.
2) Work consumes everything.
3) Family & health get leftovers.
4) You’re just going through motions.
5) You know you’re meant for more — but have no idea what.

It’s costing you — emotionally, physically, financially.
You feel stuck. Fading.

That was me.
Divorced. Burnt out.
Later — remarried, rebuilt, and free.

I made my employer my investor.
Cut hours in half.
Launched a business around my genius.
Graduated corporate life — forever.

Now I help others do the same.

Corporate Graduation™ is the system.
165+ have used it to:

✅ Compress their job into 20 hours/week
✅ Exit with runway, not regret
✅ Build a premium service business that reflects who they are
✅ Create leverage through proprietary IP, not more hours

This is how you build your founder future — without burning bridges.

This isn’t about dabbling.
It’s about reclaiming your life.
For your family. Your future self. Those you’re meant to serve.

No “passive income” BS.
Just active transformation — with revenue, clarity, and agency.

Ready to graduate?

👉 DM me “GRADUATE.”

Matt Doan

Corporate life taught me to follow the rules.

Founder life taught me this:

Create. Communicate.

That's it.

One of my coaches drilled this into me: your greatest job as a founder is to create the vision and communicate it relentlessly.

I just spent two days holed up in my studio working on Corporate Graduation marketing.

Exhausted. Back hurts. Mind hurts. Want to cry, need coffee and a giant sandwich.

But this is the work.

Creating a category out of nothing. Designing a future that doesn't exist yet. Building the language that shows people what's possible.

I live and breathe this transformation. I know it saves lives.

People desperately need the ability to move from corporate past to founder future.

And if I don't communicate it clearly, they'll stay stuck.

So every now and then you go dark.
You hole up.
You get messy.

Because messy is where breakthroughs happen.

Marketing isn't a side task for founders.

It's the job.

You create the vision. The transformation. The system.

Then you communicate it. Over and over. Until it implants in their minds.

Not when you feel inspired.

When people need to hear it.

Create. Communicate.

That's what founders do.

---

Access deep-dive Corporate Graduation strategies, stories, and tactics: https://lnkd.in/eDEkDVb2

AI can hand you a map.

But it won't climb your mountain.

You can get endless strategies in seconds now. Frameworks. Templates. Checklists.

But here's the hard truth:
Information isn't transformation.

When you're staring down a life change as big as graduating corporate life, leaving a "safe" paycheck for your own economy, you don't just need answers.

You need remarkable courage to act on them.

And that's where AI stops.

It won't sit with you through the fear.
It won't read the doubt in your eyes.
It won't push you past the moment you want to quit.
It won't connect you to people on the same journey.

Because your wiring is 100% human.

You crave deep, real connection. You need a room with energy. You need to feel seen, heard, and understood by people walking the same path.

That's why inside Corporate Graduation, we use AI as a tool to accelerate you. World-class frameworks, systems, and clarity to help you move faster than ever.

But our real focus? Our specialty?

It's what AI can't touch:

1) Human connection that makes you feel less alone
2) Belief and momentum that pulls you forward
3) Coaching that cuts through your blind spots
4) Community that won't let you play safe

That's the only way to navigate the messy, terrifying, wildly rewarding process of leaving corporate for good and building a life of meaning, money, and freedom.

AI can provide endless routes.

But only you can reach the summit.

Corporate had total control over my life.

I didn't know I had a choice.

For years, my corporate role consumed everything.

It owned my mind space. My emotional state. It ran in the background like a virus controlling my entire operating system. I couldn't turn it off.

I assumed this was just how it worked. The price of playing at a high level.

Until it erupted.

Divorce.
Not seeing my kids the way I wanted.
Living on anxiety medications just to function.

I knew I had to do something.

So I did what most trapped executives do. I chased escape routes. Real estate deals. Side hustles. New sources of cash flow.

And I realized something that changed everything:

None of that was the problem. Not even close. 

Those are downstream solutions to an upstream disease. You can't side-hustle your way out of emotional captivity.

The most important problem to solve was staring me in the mirror.

Here's what actually had to change:

1) I had to own what I was allowing.

Not what my company demanded. What I chose to say yes to. The truth nobody wants to hear is that most of the chaos in your life exists because you keep agreeing to participate in it. The late-night emails. The weekend fire drills. The manufactured urgency that evaporates by Monday. You're not a victim of these systems. You're a volunteer. I had to get ruthlessly intentional about my relationship with work. What I engaged with. What I ignored. What I protected as sacred.

2) I made myself strategically unreachable.

I worked at one of the most demanding companies in the world. Management consulting. And quietly, methodically, I engineered my days down to 4-5 hours of actual work. Maximum. Mornings were mine. Nights and weekends were mine. I became hard to reach. Slow to respond. Unavailable for things that didn't matter. Here's the psychological game nobody tells you: scarcity increases perceived value. The less available I became, the more my contributions were valued when I did show up.

3) I used my best energy to become a founder.

Not for the job. For myself. Every morning before the corporate machine turned on, I was training. Building new skills. Working with coaches. Learning how to create something from nothing. My best hours went to my future, not their quarterly targets. This only worked because of the Decoupling. The emotional detachment. Seeing myself differently. New programming. New choices. I stopped letting that environment happen to me and started happening to it.

The Decoupling is where Corporate Graduation starts.

It's the only place to start.

Not the cash flow model.
Not the business plan.
Not the exit timeline.

Those come later.

First, you unhook your nervous system from systems that were never built for you to win.

Then you get to work.

---

PS - We're doing something special this month to help you build this capability. DM me DECOUPLE for early access.

Corporate secretly became my secondary environment.

I built my new "primary" in the shadows.

I was still showing up to work. Still delivering. Still getting promoted.

But everything had changed.

I joined a $10K entrepreneurial mastermind. I was the only corporate guy in the room. Everyone else was building businesses, scaling impact, living as founders.

I started messy: 
...Learning copywriting
...Funnel building
...Coaching skills
...How to build a founder-grade business from zero

I immersed myself in books, mentors, and peers who were living the future I was starving for.

And for the first time in my entire life, I felt alive.

Not in school, where everything was pre-programmed and standardized.

Not in corporate, where I was climbing someone else's mountain.

This was different.

I'd never been in an environment that felt authentically designed for me. Where I was being called and activated into a new future. Where I belonged.

Here's what I learned:

1) Environment does the work you can't do alone.

You can't think your way into a new identity. You need to be surrounded by people who already embody it. The right environment pulls you forward faster than willpower, discipline, or strategy ever could.

2) Choosing a new tribe is an act of Decoupling.

When I reprioritized who I spent time with, who I learned from, who I wanted to become like, corporate's grip on me loosened. I wasn't fighting to leave anymore. I was being pulled toward something I actually wanted.

3) No amount of information will activate you like this.

I could've read a thousand books. Taken a hundred courses solo. Studied every framework. But being IN the room with founders? Hearing their struggles, seeing their wins, feeling the energy of people carving their own path? That's what flipped the switch.

---

At any given moment over the last 10 years, I can point to multiple mentors or programs that keep me challenged, activated, pushed, inspired, and growing new skill sets and mindsets.

(This is vital.)

And I can point to that as the single most important factor in my Corporate Graduation.

Environment isn't everything.

It's the only thing.

The Decoupling starts when you choose where you belong next.

---

PS - Choosing a new environment was step one. Learning how to make corporate optional while still employed was step two. 

I break down the full framework in this new training: go.corporategraduation.com

My Double Life in Corporate

There are no big decisions.

Only choiceless ones.

"Big decisions" come from friction. Wrestling with options. Trying to force clarity that isn't there yet.

(You can't rush this.)

Choiceless decisions feel obvious. 
Aligned. Like there's no competing path.

Your head might present other options. Other voices might argue that you should "be sensible," or that the path is hard. And yes, it can be incredibly difficult.

But search inside. 
You've likely already made the decision.

That's how you know it's choiceless.

Here's what I've learned:

1. You can't force something to be choiceless.

2. You just know when you tune into your intuition.

3. When it's the right time, the decision is obvious.

4. You say to yourself: "Of course. This is my path."

5. Yes, it will be hard. Scary. It will test you.

6. But you have no choice because it feels 100% aligned.

7. This is where you're meant to go.

8. Ideas start presenting themselves. Mentors appear. Evidence shows up.

9. Sometimes the outside world intervenes. A layoff. An eruption. Validating what's been floating in your mind.

10. Something being choiceless is an inner signal. You can't rush it. You can't force it.

---

I faced this when leaving my first marriage. 3 young kids at home.

I faced it in graduating the "safety" of corporate.

I faced it when Cecilia and I decided to have our own biological child. She was a stepmom. We already had 3 kids.

I face it every time I invest in programs that scare me. Rooms that challenge me. Work that levels me up.

I faced it building a business that felt authentically me.

None of these looked small from the outside.

All of them were choiceless from the inside.

---

Decoupling from corporate wasn't a big decision for me either.

It was choiceless.

I was being called to graduate. To become a founder. To carve my own life.

So Decoupling was the necessary work in front of me. Reclaiming my precious time, energy, and attention as a first move toward my overall corporate graduation.

I had no choice in the matter.

So I got the support and resources to do the work.

On the other side of Decoupling, the choiceless path continued.

Not easier. But obvious.

The timing had become right. So I trusted the feeling.
And kept moving.

Remember:

There are no big decisions.
Only choiceless ones.

I wanted to feel confident before making the big move.
 
It never showed up.
 
Because here's the truth:
 
Confidence only comes after you move.
 
Not before you start the business. 
Not before you circle the resignation date. 
Not before you have the hard talk with your partner. 
Not before you commit to the thing sitting in your chest.
 
You move first. Then confidence follows.
 
Dan Sullivan calls it the Four Cs:
 
1) Commitment
You decide on the new future. Not "I'll try" or "maybe someday." You're 100% decided, even with the path unclear. The outcome is no longer negotiable. You cross the line mentally before you cross it physically.

2) Courage
You create the conditions for it. You put yourself in the room with the tribe. You invest. You put skin in the game. This isn't about feeling brave. It's about building the structure that won't let you back out.

3) Capability
You develop it by doing. New skills. New mindset. New ways of seeing yourself and the world. You don't learn this in theory. You learn it by being in it, making mistakes, adjusting, getting better.

4) Confidence
It arrives as the byproduct. You gain traction. Things start working. You look back and realize you're not the same person who started. That's when confidence shows up. Not before.
 
Most people get stuck waiting at the starting line for confidence to tap them on the shoulder and say, "Okay, now you're ready."
 
Guess what? It'll never arrive.
 
Because confidence doesn't just magically appear.
 
It's something you create.

Sr. Director at a multi-billion dollar company.
Done with his workday by 10 AM.
Meet Travis.

"Hangin' at a coffee shop.
Done with my workday."

Just a few weeks before, this was his reality:

✘ 12-hour days
✘ Holed up in his office, grinding
✘ Reacting to nonstop pings from global teams

In just days, Travis got his life back.

He faced his stories and fears:

Took a raw look at time and energy.
Did the audit + engineering work.
Took sweeping control of his job.

Now? He's flipping the script:

✓ Employer = investor
✓ Job = short-term asset
✓ Even improving his reputation

This isn't "quiet quitting."
This is being an adult.
Choosing Real Work. Declining Fake Work.

Corporate today is a performative nightmare.

But if you strip it to essentials, and have the guts to defend that line, you win.

Big time.

It helps everything and everyone in your life:

Your happiness.
Your health.
Your family.
Your future.

Travis is just beginning his Corporate Graduation.
But already, the foundation is settling nicely.

First SPACE: reclaiming time, energy, and attention.

Next SELF: forging a bold, "founder" identity. Someone who relishes challenges, faces fears, and pushes through, knowing the payoff is worth it.

Then SYSTEM: with the foundations in place, building a uniquely valuable business that energizes him and creates a new long-term pathway.

From there, corporate becomes optional.

Notice the framework. The sequence.
There's more underneath — it's the flow that matters. 

No rage quitting.
No emotional reactions.
Just calm, decisive moves.

This is how you build a future you haven't even let yourself dream of yet.

And you should've seen Travis when he shared this with our client group — pride, relief, possibility in his eyes.

This is a tipping point for him.

When bold little moves compound.
And suddenly explode into massive change.

---

PS: That's why I built the Corporate Compression™ GPT.

It's the exact audit and re-engineering process my Director, VP, and Executive clients use to smartly compress their workday by 50%+ while maintaining their reputation and building the space needed for their Founder future.

DM me "COMPRESSION" if you want access.

Wanna know the most dangerous word after "I quit"?

It's "consultant."

Your whole career has been defined by labels.

Analyst. Manager. Director. VP. SVP.

Each one felt like progress.
Each one was just a different-sized box.
Then you start thinking about what's next.

And what happens?

You reach for another label.

"I'll be a consultant."
"I'll be a coach."
"I'll go fractional."

You've traded one box for another. Except this one doesn't come with benefits, a team, or a paycheck.

Here's what I've seen over and over:

People leave corporate, call themselves entrepreneurs, and end up trading time for money in a lonelier, less stable version of what they left.

I call this corporate replication.

You repackage everything you know under your own name and wonder why it feels exactly like what you left.

This is not the path I advocate.
The path I advocate is that of a founder.
A founder doesn't sell time for money. Ever.

What you bring to the market is valued by outcomes, not hours.

A founder builds a machine. A system that delivers remarkable outcomes for those who desperately need it.

That machine runs on three things:

1) Vision
A new future that needs to exist. A category you see because your experience gave you eyes others don't have.

2) Voice
You communicate that future with conviction. The window won't stay open forever.

3) Velocity
You move quickly. You attract people before the moment passes.

The real work? Extracting your IP.

You pull out the frameworks living inside your head. The patterns you've been running on for twenty years but never named.

You visualize them. Test them. Trademark them. Speak about them until people associate you with this category.

Right now, my clients are building categories like:

• Career Free Agency
• FinLaw Orchestration
• Motherhood By Design

None of them are billing hourly.

They're building machines.

This is the System pillar of Corporate Graduation.

Space gave you the room.
Self gave you the identity.
System is where you build the machine.

---

Give me your take - how does that land with you?

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