Hi, I’m Ryan. I help high performers become founders by using LinkedIn to build real, profitable businesses.

My career didn’t fall apart. I didn’t burn out. I finished every role cleanly - Director, VP - leading hundreds of engineers across the world and helping build multiple billion‑dollar companies.

And still, I knew I wanted to build on my own.

I’ve founded 5 companies and earned multiple exits while scaling teams behind $1B+ in outcomes. I loved the work, but I wanted a life where I could build big things and be present for my family. I wanted ownership. I wanted flexibility. I wanted proof I could do it on my terms.

LinkedIn became the path. I grew from 1,200 to 100,000+ followers in nine months, built a brand that opened doors I didn’t know existed, and stepped fully into my own business.

Since then, I’ve coached 50+ founders to design careers, income streams, and opportunities that match the life they actually want - not the life their company dictates.

Here’s how we work:

- Identify the opportunities you can’t see in your past experience.
- Build a clear, practical brand that attracts the right people.
- Turn your skills into simple offers, real customers, and predictable income.

Today, I own my time. I build, coach, and spend my days with my family - and help others do the same.

If you’re a high performer who wants a business that fits your life, DM me.
Partnerships, speaking, press: ryan@ryanyockey.com

Professional highlights:
• 5× Founder | Multiple exits
• Scaled teams responsible for $1B+ outcomes
• Grew to 100,000+ followers in 9 months
• Coached 50+ founders
• Trusted by leaders at Google, Adobe, Meta

Ryan Yockey

I’ve been watching people for years. The patterns are wild.

The loudest person in the room? Usually compensating.

The flashiest? Probably broke or close to it.

The one who won’t shut up about how smart they are? Not that smart.

Here’s what I’ve noticed about people who actually have it:

The strongest are gentle.
They don’t need to intimidate. Their presence does the work.

The smartest are quiet.
They listen more than they talk. They know they don’t know everything.

The wealthiest are simple.
No logos. No flex. Just compound interest and time freedom.

The happiest are private.
They’re not performing for an audience. They’re living for themselves.

Real power doesn’t need to prove itself.

It just exists.

The person who’s actually built something doesn’t need to tell you about it every five minutes.
Their results speak.

The person who’s actually confident doesn’t need external validation.
They’ve done the internal work.

If you find yourself constantly trying to prove your worth, your intelligence, your success—pause.

Ask yourself who you’re trying to convince.

Because the people who’ve made it?
They stopped performing a long time ago.

They just started building in silence.

That’s what I write about every Saturday. One short note to 135,000+ entrepreneurs who care more about real progress than public applause.

It takes 4 minutes.

And its free: https://lnkd.in/gfyweeTM

No noise.
Just the work.

Actionable strategies to grow your audience, monetize your skills, and build leverage online. | Trusted by leaders at Google, Adobe, Meta

The real luxury isn’t making millions.

And it’s definitely not your internet dream.

It’s easy to confuse money with freedom.

Fast cars.
Big houses.
Screenshots and timelines.

But watch closely.

The people who actually "made it"
optimize for something much quieter.

I control my time.
I can choose when to workout.
I dont have nearly the level of stress I once did.

Slow mornings without guilt.
Rested afternoons whenever I want.
Sleep that isn’t borrowed from tomorrow.

And most importantly:

People you love.
Who love you back.

Money can certainly help create these things and more, theres no denying that.

But chasing money at the expense of them usually destroys the very life you’re trying to build.

I learned this the hard way.

The goal isn’t more.
It’s enough — designed intentionally.

That’s what I write about every Saturday.

One short email to 135,000+ entrepreneurs on building work and lives that don’t collapse under success.

It takes 4 minutes to read.

It’s free. Join here: https://lnkd.in/gfyweeTM

Slow down.
You’re closer than you think.

I waited longer than I should have.

Not because I didn’t have ideas.
Not because I wasn’t capable.

Because I kept telling myself I needed:
More clarity.
More confidence.
More proof it would work.

I thought I needed a better plan.

I didn’t.

I thought I needed permission to try new things.

I didn't

I thought I needed someone to tell me it was okay to start.

I didn’t.

What I actually needed was to stop questioning myself.

Every meaningful thing I’ve built started the same way:
Messy.
Incomplete.
Uncomfortable.


The people I know who’ve built real businesses didn’t wait for the right time.
They started before it made sense.
They figured it out while delivering.
They gave themselves permission to start.

Most people do the opposite.

They plan.
They ask.
They wait.

Your competition isn’t other people.

It’s your own hesitation.

Stop asking if you’re ready.
Start doing the thing you keep thinking about.

That’s what I write about every Saturday.

One short note to 135,000+ entrepreneurs who stopped waiting and started building.

It takes 4 minutes.

It’s free: https://lnkd.in/gfyweeTM

Start sooner than you feel comfortable.

The most valuable skill isn’t productivity.

It’s knowing what matters.

Anyone can work harder.
Anyone can move faster.
Anyone can optimize their calendar.

That’s not the edge.

The edge is knowing what not to do.

Because efficiency on the wrong things is still wasted energy.

I see this constantly.

People obsess over:
• Morning routines
• Task managers
• AI workflows
• Productivity hacks

But they’re applying them to work that doesn’t matter.

So they feel busy.
They feel exhausted.
And they wonder why nothing compounds.

Real leverage comes from clarity.

Knowing:
• Which decisions actually move the needle
• Which problems are worth solving
• Which work creates momentum instead of maintenance

Most professionals don’t need better systems.

They need better filters.

Once you know what matters, productivity becomes obvious.
Until then, it’s just motion.

That’s what I write about every Saturday.

One short email to 135,000+ entrepreneurs on building conviction, making clearer decisions, and designing work you’re proud to stand behind.

It takes 4 minutes to read.

It’s free. Join here: https://lnkd.in/gfyweeTM

Keep building.
The right people notice.

Deloitte Partner | Keynote Speaker & Executive Coach | Guiding leaders out of The Success Trap

I’m Clif Mathews, a Partner at Deloitte with 25 years of experience advising senior executives through major transitions and defining leadership moments. 

Over the years I’ve seen how even the most accomplished leaders can reach a point where their own success starts to feel limiting, when what once worked no longer moves them forward.

I call this The Success Trap:

👉 When the very habits that built your career become the ones that keep you from moving forward.

Leaders find themselves here:

- Delaying big decisions out of fear of being wrong
- Struggling to hold influence in the rooms that matter most
- Achieving more and more, yet feeling less fulfilled

They have done everything right and now wonder, “Is this all there is?”

That is where I focus my work. I help senior executives break free from The Success Trap and move from optimization to integration. The goal is to reconnect achievement with authenticity, values, and well-being.

This is not performance coaching, stress management, or job search prep. It is about helping leaders build clarity, courage, and alignment before they make their next big move.

My clients learn to:

✅ Make courageous calls when the stakes are highest
✅ Rebuild confidence in their judgment and influence
✅ Lead in ways that feel both successful and sustainable

At the heart of my approach are four values:

- Exploration: asking better questions instead of clinging to old answers
- Empowerment: helping leaders back themselves when certainty is not possible
- Authenticity: showing up with integrity, playfulness, and courage
- Prosperity: building growth that feels healthy, aligned, and worth celebrating

Every day, I share ideas and experiences on leadership and how to break free from: The Success Trap. 

♻️ Follow for fresh perspectives, or DM me to explore a collaboration or speaking opportunities.

📧 Sign up for my newsletter: Second Summit Brief — a weekly read for executives who climbed the “right” mountain, only to realize it wasn’t their own. Every week, I share insights on finding YOUR summit. Integration over optimization, alignment over altitude, different terrain instead of higher ground. Subscribe here: https://www.clifmathews.com/newsletter

Clif Mathews

The most powerful pivot in your career...

Can feel like a failure at first.

Image credits go to Alvin Huang!

There's a pattern that can appear with successful leaders at times.

They've checked every box, built a great career, and earned impressive titles.
And yet, there's a quiet feeling that something's still not right.

On paper, they're incredibly successful, but it still feels like they're behind.

If you've ever felt this, you're not alone. And there's a good reason why it happens.

For our whole lives, our brains do what they're built to do.
Dopamine hits us whenever we achieve something new.

New title? Dopamine.
Promotion? Dopamine.
Closing a big deal? Dopamine.

As you keep going, the dopamine hits keep coming,
until somewhere along the way, you stop checking whether you're on the path that's right for you.

That creates the feeling that something's not quite right.

And in some cases, it starts a negative spiral where you believe your achievements are failures.

But choosing a new path isn't a failure.

In fact, it's often the first step to achieving more success.

You hit a low point and realize something's off.
↓
You acknowledge how you're feeling and wonder what you can do.
↓
You find the root cause of the strange feeling.
↓
You learn what you actually care about in your work.
↓
You start to connect the dots between your current path and what you want.
↓
You adjust your direction based on what truly matters to you.
↓
You move forward feeling clearer and more aligned than before.

If you've ever felt like you need to pivot, that's not a failure.

It's a signal that your external success and internal alignment aren't completely in sync.

But once you realize that, you can start taking steps to close that gap.
And that's one of the bravest things you can do.

Have you been through this before? How did you define your success?

I created a worksheet to help with this exact problem.

It'll help you realize whethr your following your own goals,
or someone else's definition of success.

You can get it for free here: bit.ly/before-you-climb

---

➕ For more posts on defining success on your own terms, follow Clif Mathews.
🔁 Repost to help another leader reflect on whether they're still on the right path.

Wanting something new isn't selfish.

You're allowed to change direction.

There's something that happens when you achieve success and it stops feeling right.

You've built your career, earned respect, and proven you're capable of anything.

For some people, there's a pull to pivot and try something new.
And instead of feeling like progress, it might feel like failure.

When you've spent years building toward an idea of success, it's natural that change can feel scary.

But that desire to try something new isn't failure.

It's a signal telling you that your version of success doesn't fully align with who you are now.

And that's okay.

The more you grow, the more you learn about yourself.
And that self-awareness can push you toward success that feels like yours.

But if it still feels difficult, it's worth asking yourself why:

❓ Am I afraid of what other people might think?
❓ Does staying really feel safer than admitting I want something different?
❓ Who am I outside of my achievements at work? 

They're tough to answer, 
but they reveal the beliefs that keep you stuck.

Outgrowing old ideas of success doesn't make you ungrateful.

And as you get clear on what you actually want,
it becomes easier to let go of what doesn't serve you anymore.

So before you dismiss the idea of change, ask yourself:

→ If I stripped away what impresses people, what would I actually pursue?
→ What version of success makes my energy expand instead of contract?
→ What would I regret not trying?

You don't need to have everything figured out right away.

Be honest with yourself. That's the first step.

I'm covering exactly how to start turning your ideas into action in my newsletter tomorrow.

For anyone who's trying to build something new for themselves,
this one's for you.

👉 Click here to sign up: bit.ly/SecondSummitBrief

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For more posts on redefining success on your own terms, follow Clif Mathews.
🔁 Repost to remind another leader that growth isn't failure.

Emotional intelligence doesn't come down to a single skill.

Every moment calls for a different hat.

Many execs know that emotional intelligence means being open and listening to different perspectives.

What trips them up is applying the right kind of EQ to the right situation.

That's why they have to become familiar with the different hats they should wear.

Here are 9 that matter most:

1️⃣ The Visionary
↳ Helps the team understand what success looks like and see the road to get them there.

2️⃣ The Coach
↳ Develops their team through questions, feedback, and work that stretches them.

3️⃣ The Teacher
↳ Steps in to teach a certain skill when the team needs a shared baseline.

4️⃣ The Translator
↳ Turns messy complexity into clear language, owners, and next steps.

5️⃣ The Problem Solver
↳ Steps in to address urgent problems, and sets long-term solutions to prevent repeats.

6️⃣ The Connector
↳ Builds trust and creates real collaboration across the team.

7️⃣ The Advocate
↳ Reduces unnecessary stress while defending the team’s time, energy, and priorities.

8️⃣ The Role Model
↳ Sets the tone for the entire team through their behavior, values, and habits.

9️⃣ The Service Leader
↳ Removes any blockers and makes sure the team has what they need to do great work.

The mistake most leaders make is picking one hat and wearing it all the time.

They default to problem-solving when people need guidance.
Or stay focused on the vision when the team needs to build more trust.

But the more you recognize which situation needs which hat,
the faster you can create a great culture for your team.

Which hat do you wear most often?

For more posts on emotional intelligence in leadership, follow Clif Mathews.

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📨 Every week, 12,000+ execs learn how to define their own success in my newsletter, The Second Summit Brief.
Sign up here so you don't miss out: bit.ly/SecondSummitBrief

🔁 Repost to help other leaders recognize when they need to switch hats.

20 Lessons from Atomic Habits

(Every leader should read these. Twice.)

Thanks to Gareth Lloyd for putting this together!

When it comes to achieving goals, a lot of execs only rely on motivation.

It can work for a while, but eventually, motivation runs out.

Instead of relying on willpower, it's more effective to build habits into your day.

Over time, those small, consistent actions build up.
You're able to create routines that protect your energy instead of burning through it.

Here are some of the lessons that resonate with me most:

1️⃣ Identity drives your habits.
2️⃣ What you repeat, you become.
3️⃣ Your habits show your priorities.
4️⃣ Your systems determine your success.
5️⃣ Better environments create better decisions.
6️⃣ Tiny steps, done daily, create lasting change.
7️⃣ Make good habits obvious and bad habits difficult.

When you build a consistent routine, your leadership improves in all areas.

You're better at protecting your energy.
Your goals become measurable rather than staying vague.
Your confidence improves because you see the results stack up.

And most of all, your team starts following the example you set.

If you're aiming to be the best leader you can,
think about the habits you need to become that person.

Putting them in place makes achieving your goal much easier.

Pursuing the right goal is just as important as building the right habits.

That's why I created a worksheet to help.

It walks you through five key questions to figure out your version of success,
and create goals that truly feel right for you.

You can get it for free here:
https://lnkd.in/gtWPrWa9

Have you read Atomic Habits? What are your thoughts on it?

For more posts on building sustainable leadership, follow Clif Mathews.
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📨 Every week, 14,000+ execs learn how to define their own success in my newsletter, The Second Summit Brief.
Sign up here so you don't miss out: bit.ly/SecondSummitBrief

🔁 Repost to remind another leader that their habits shape their impact.

Running on autopilot will keep you efficient.

But rest lets you lead with real impact.

When you're constantly stressed or disconnected from what recharges you,
your brain becomes wired for survival mode.

It can get you through tough periods, but over time you become more and more drained.

Sometimes it looks like the only solution is to keep pushing forward.

But if everything feels harder than usual,
it's a sign that you actually need to take a step back.

You can rewire your brain so stress isn't your default wiring.

A few ways to do this:

🏃‍♂️‍➡️ Exercise daily.
🚶‍➡️ Take a walk in nature.
🎵 Dance to your favorite song.
📖 Finally read that book you bought.
📵 Spend a few hours without your phone.
🛏️ Get 8 hours of quality sleep each night.

A lot of leaders see switching off as a reward for hard work.

But taking a rest is a key part of hard work.

When you stop running on autopilot and rewire your brain,
you recognize which parts of your work feel meaningful.

That helps you prioritize what matters most in your professional and personal life.

Start small. Pick one thing from the list and make it your priority for the week.

Your brain will thank you.

What's one thing you do to reset?

For more posts on building rest into your leadership, follow Clif Mathews.

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📨 Every week, 12,000+ execs learn how to define their own success in my newsletter, The Second Summit Brief.
Sign up here so you don't miss out: bit.ly/SecondSummitBrief

🔁 Repost to remind another leader to step back and reset.

We teach people how to work.

We rarely teach them how to work well together.

Newer execs often start their roles thinking about the legacy they want to leave behind.

But to create a strong impact, they need the full support of their team. 

The best way to do that is to invest in their growth and build their confidence.

It's not an easy skill to master,
but these six frameworks are a great place to start:

1️⃣ The Five Stages of Team Development
↳ Understanding how high-performing teams are formed removes any worries.

Nearly every strong team goes through these stages:

• Forming → People meet, roles are unclear
• Storming → Friction shows up as styles collide
• Norming → Shared habits form and collaboration clicks
• Performing → The team operates with speed and ownership
• Adjourning → The project wraps or shifts into something new

2️⃣ The Trust Triangle
↳ Trust grows when three things are consistently true.

Authenticity → Are you genuine and consistent?
Empathy → Do people feel understood and cared for?
Logic → Do your decisions and reasoning hold up?

3️⃣ The Energy vs. Impact Matrix
↳ Map each person by their engagement and contribution.

High Energy + High Impact → Promote and empower
High Energy + Low Impact → Coach or redirect
Low Energy + High Impact → Reignite motivation
Low Energy + Low Impact → Reassess role or exit

4️⃣ The RAPID Decision-Making Framework
↳ Identifying clear ownership prevents confusion and delays.

Recommend → Propose a clear plan
Agree → Secure essential buy-in
Perform → Execute the decision
Input → Provide expertise to inform the choice
Decide → Make the final call

5️⃣ The Johari Window
↳ A simple model for feedback and self-awareness.

Open Area → Known to self and others
Blind Spot → Unknown to self, known to others
Hidden Area → Known to self, unknown to others
Unknown Area → Unknown to both

6️⃣ The 70-20-10 Learning Principle
↳ This is the most effective way for people to develop.

70% through hands-on experience
20% through mentoring or coaching
10% through formal training

Every leader will gravitate toward different frameworks.

You don't need to use all of them to create an effective team.
Choose the ones that feel most natural and see how well they go.

Have you used any of these before? What's worked for you?

For more posts on building high-performing teams, follow Clif Mathews.

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📨 Every week, 6,000+ execs learn how to define their own success in my newsletter, The Second Summit Brief.
Sign up here so you don't miss out: bit.ly/SecondSummitBrief

🔁 Repost to help other leaders strengthen their teams.

Your team can mentally check out long before resigning.

Most leaders don't notice until it's too late.

By the time it's obvious that something's wrong, the damage is already done.

There are a lot of signals in the run-up to a culture breaking down.

But leaders often miss them because they're focused on deliverables, strategy, and results.

When you know what to look out for,
you can spot the signs before things spiral out of control.

Here are the 8 signals every leader should be wary of:

1️⃣ High employee turnover
↳ This is one of the biggest pointers to deeper issues in the workspace.

2️⃣ Lack of psychological safety
↳ Team members don't feel safe speaking up, so problems go unaddressed.

3️⃣ Poor leadership accountability
↳ They deflect responsibility and fail to model desirable behaviors.

4️⃣ Chronic burnout
↳ Overwork and constant urgency are treated as normal.

5️⃣ Values that are unclear or not lived
↳ They exist on paper, but daily decisions and behaviors prove otherwise.

6️⃣ Office politics over collaboration
↳ Employees compete and compare, which leads to teamwork breaking down.

7️⃣ Low trust and transparency
↳ Decisions are made behind closed doors, fueling unhelpful rumors.

8️⃣ No clear growth or development paths
↳ Employees feel like there's no chance to learn, grow, or advance.

If you've spotted any of these signs in your workplace, 
it doesn't make you a bad leader.

What matters most is what next steps you choose to take.

Pay attention to what's not working.
Ask people what they think needs changing.
And act on the feedback you get.

Which of these signs do you think is most important to look out for?

For more posts on building sustainable team culture, follow Clif Mathews.
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📨 Every week, 14,000+ execs learn how to define their own success in my newsletter, The Second Summit Brief.
Sign up here so you don't miss out: bit.ly/SecondSummitBrief

🔁 Repost to help another leader spot culture breakdown before it's too late.

Your accomplishments are only part of your leadership.

Your real impact is about who you help.

A lot of execs make this mistake. 

They assume leadership means being the one who makes every call.

Because they care about their work, 
it feels easier to be involved in every detail and task.

But if you hold on too tight to what's not yours,
you burn yourself out and lose the trust of your team.

Your value isn't in being the smartest person in the room.

It's in helping others discover what they're capable of.

Real leadership looks like this:

1️⃣ Leading through influence, not control
↳ Authority gets compliance. Influence creates commitment.
↳ In your next meeting, ask for people's thoughts before sharing your view.

2️⃣ Growing through continuous learning
↳ Leadership requires evolving as the role demands more of you.
↳ Think about one skill you want to improve and work on it this quarter.

3️⃣ Serving and supporting your team
↳ You can't leave an impact without supporting your team.
↳ Ask "What do you need to succeed?" more often than "Why isn't this done?"

4️⃣ Empowering people and collaborating effectively
↳ Delegating tasks allows your team to develop their judgment.
↳ Give someone a task or decision to make, and let them own it.

5️⃣ Taking ownership and responsibility
↳ When something goes wrong, it's on you. When something works, credit the team.
↳ Practice saying "I should have..." instead of "They didn't..."

6️⃣ Developing the next generation of leaders
↳ Your legacy isn't what you accomplished. It's who you helped become great.
↳ Ask where each person wants to be in two years and help create that path.

Your leadership goes beyond your own accomplishments.

It's about how you help your team achieve their goals. 
That's how you multiply your impact and build something that lasts. 

If you've had a leader who's helped you grow, tag them in the comments to let them know!

For more posts on rethinking leadership, follow Clif Mathews.

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📨 Every week, 14,000+ execs learn how to define their own success in my newsletter, The Second Summit Brief.
Sign up here so you don't miss out: bit.ly/SecondSummitBrief

🔁 Repost to help other execs make a bigger impact in their work.

Your language can build or break your leadership.

Refine your words, and trust will follow.

Execs often think about building their influence through their actions.

They're quick to come up with strategies and are excellent at delivering outcomes.

But your impact doesn't only come from the goals you achieve.
It's built every day in how you speak to others.

The problem is that most leaders don't realize when their words can work against them.

One deflection in a meeting.
One vague comment.
One moment of defensiveness.

Those small moments might not feel like much.

But in the long term, they can cause your team to stop bringing up real problems.

The good news is that your influence can be rebuilt by making small changes in your language.

Here are 8 phrases leaders say that limit their influence:
(and what to say instead)

❌ "Here is the answer."
✅ "What am I missing here?"
→ People back leaders who listen, not ones who dominate the conversation.

❌ "I don't agree with this, but we have to do it."
✅ "Here's why this decision was made and how it affects us."
→ If you won't stand behind a decision, people stop standing behind you.

❌ "Let's move on."
✅ "I can sense hesitation. What worries are coming up?"
→ Unspoken worries won't disappear. They'll just get louder later on.

❌ "There's nothing to worry about."
✅ "I know this brings uncertainty. Let's talk through what it means."
→ People want to feel understood before having to move forward.

❌ "I will try to get to it."
✅ "I will have this done by Friday."
→ People trust what you do, not what you intend to do.

❌ "I heard something similar."
✅ "I would rather hear this directly from them."
→ Once people feel unsafe around you, they stop being honest.

❌ "You're not seeing the full picture."
✅ "Help me understand how you are seeing this."
→ Defensiveness shuts people down. Asking for their viewpoint keeps them engaged. 

❌ "I need to respond to this right now."
✅ "I want to think about this before responding."
→ Calm leaders make people feel steady. Rushed ones don't.

Communicating calmly and clearly is one of the consistent ways to build up your influence.

It's a skill that can be hard to master,
but as you practice, you'll become more confident and your team will open up to you more.

If you're ever in doubt about how to respond, pause first.
A few seconds of thinking might be the difference between a poor response and a great one.

For more posts on building influence as a leader, follow Clif Mathews.

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📨 Every week, 13,000+ execs learn how to define their own success in my newsletter, The Second Summit Brief.
Sign up here so you don't miss out: bit.ly/SecondSummitBrief
🔁 Repost to help another exec recognize how language shapes their leadership.

Disagreeing with your CEO isn't disrespectful.

Staying silent when you see a problem is.

I've worked with a lot of new execs who struggle to find their voice in their role.

One of the biggest worries is speaking up when a decision doesn't sit right with them.
If that decision was made by the CEO, they stay quiet.

It feels easier to go along than to risk being seen as difficult or disrespectful.

If you've ever felt that, I want to remind you of this:

You weren't promoted to exec level to nod along to every decision.
You were brought into the room because your judgment matters.

And there are plenty of ways to do it without damaging the relationship between you and the CEO.

Here's how:

When you're challenging a decision:
❌ Don't say: "I just don't think this is right."
✅ Try: "Here's what I'm seeing, based on the data."

When you've heard others agree:
❌ Don't say: "Everyone else feels the same way."
✅ Try: "I've heard similar concerns from finance and marketing, independently."

When you're highlighting a problem:
❌ Don't say: "This won't work."
✅ Try: "Here's another way that might solve it better."

When you're framing the issue:
❌ Don't say: "I disagree with your approach."
✅ Try: "We're both trying to achieve the same goal. Here's a path that might get us there faster."

When you're choosing the moment:
❌ Don't say: (in front of 10 people) "I don't think that's right."
✅ Try: "Can we talk through this one-on-one?"

When you're early in the conversation:
❌ Don't say: "I might be wrong, but..."
✅ Try: "Here's what I'm seeing so far."

When the CEO doubles down:
❌ Don't say: "But you said..."
✅ Try: "Can I ask how you're thinking about it now?"

The best CEOs don't want yes-people around them.
They want you to bring in your expertise and challenge things when they matter.
This is your chance to create a bigger impact.

The more you practice speaking respectfully,
the more trust you'll build in the relationship.

Have you ever had a tough conversation with a CEO? How did it go?

For more posts on building trust in leadership, follow Clif Mathews.

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📨 Every week, 12,000+ execs learn how to define their own success in my newsletter, The Second Summit Brief.
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🔁 Repost to help other new execs build confidence in their role.

Before you chase the next goal...

Make sure it's actually yours.

A lot of leaders know what success looks like on paper.

➡️ Achieve a target on a key project.
➡️ Get the next promotion.
➡️ Increase your compensation and benefits.

But what can sometimes happen is that you spend so much time chasing the next goal,
that you don't pause to think about whether it's the right goal for you.

We, as humans, inherit ideas of success.

It appears in how we work and what legacies we leave behind.

But sometimes those ideas don't align with what actually fulfills you in your role. 

Taking a moment to think about exactly what impact you want to have can be the start of achieving goals that truly matter to you.

Here's how to start on that path:

See your goal
➡️ Get specific about what you want, not just what looks impressive.

Understand the obstacles
➡️ Name what's actually in the way, whether it's external or internal.

Create a positive mental picture
➡️ Visualize what success looks like when it's aligned with who you are.

Clear your mind of self-doubt
➡️ Learn the difference between legitimate concerns and fear disguised as logic.

Embrace the challenge
➡️ Acknowledge that meaningful goals require discomfort.

Stay on track
➡️ Build sustainable systems that keep you moving toward what matters.

Show the world you can do it
➡️ Take action that reflects your commitment.

None of this means you should lower your standards or choose smaller goals.

Thinking about what matters most to you makes sure your energy goes in the right direction.

That's how you start achieving what truly lights you up.

To help with the first step, I created a free worksheet.
It walks you through five key questions that help you figure out what you actually want versus what's been handed to you.

You can download it here: bit.ly/before-you-climb

What's your goal for this year? I'd love to hear about it!

For more posts on defining your own success, follow Clif Mathews.

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📨 Every week, 13,000+ execs learn how to define their own success in my newsletter, The Second Summit Brief.
Sign up here so you don't miss out: bit.ly/SecondSummitBrief

🔁 Repost to help another leader check in on the goals they're chasing.

Not all leadership lessons come from case studies. 

Sometimes, they're found in stories.

Have you ever watched a movie and seen someone who made you think,
"I want to be just like them!"?

Maybe you liked their bravery.
Or their intelligence or kindness.

Maybe you just found them really cool.

Whatever it is, chances are it shaped you as a person.

In a lot of cases, it can also influence how you work and lead. 

We learn a lot about how to work together through stories,
and seeing yourself in your favorite character might be the key to leveling up your leadership.

Here are 9 fictional characters every leader can learn from:

1. Samwise Gamgee
✅ Traits: He's loyal, persistent, and keeps going even when things are hard.
🎓 Lesson: Quieter and consistent leadership can lead to powerful outcomes.

2. Hermione Granger
✅ Traits: Intellectual, courageous, and doesn't shrink away from a challenge.
🎓 Lesson: Be prepared and give evidence to strengthen credibility.

3. Captain America
✅ Traits: Cap doesn't hesitate to think of others before himself.
🎓 Lesson: Embody service leadership. People follow execs who put the team first.

4. Vito Corleone
✅ Traits: Vito understands that influence comes from careful planning.
🎓 Lesson: Think long-term. Foresight can shape lasting outcomes.

5. Wonder Woman
✅ Traits: Wonder Woman leads through compassion and fairness.
🎓 Lesson: Authority works best when balanced with empathy.

6. Winnie the Pooh
✅ Traits: Pooh's always kind, empathetic, and patient with his friends.
🎓 Lesson: Emotional and psychological safety boosts overall performance.

7. Elizabeth Bennet
✅ Traits: Lizzy's bold, curious, and challenges what's around her.
🎓 Lesson: Question the status quo (respectfully) to make improvements in your environment.

8. Doc Brown
✅ Traits: Doc sees the possibilities others miss and is always inventing.
🎓 Lesson: Have a big imagination and take bold risks when it counts.

9. Atticus Finch
✅ Traits: Atticus stands by his beliefs despite opposition.
🎓 Lesson: Do the right thing even when it's unpopular.

Of course, there are many other characters out there you can use as a reference point. 

You don't need to fit perfectly into one specific type of leadership.

Pick out traits from people you admire the most,
and soon you'll have your own unique style that represents YOU.

Who was your favorite fictional character growing up?
What kind of traits do they have that you admire?

For more posts on leadership lessons, follow Clif Mathews.

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📨 Every week, 14,000+ execs learn how to define their own success in my newsletter, The Second Summit Brief.
Sign up here so you don't miss out: bit.ly/SecondSummitBrief

🔁 Repost to help other execs see leadership through a different lens.

Miscommunication doesn't always look like chaos.

More often, it looks like agreement.

Many leaders communicate with their teams in a way that feels right to them.
They lay out the plans, everyone nods along, and the work starts.

But somehow, the team moves in a different direction than intended.

Everyone was paying attention,
but the communication didn't land the way the leader thought it did.

Most communication breakdowns follow predictable patterns.
Once you know what to look for, you can catch them early and fix them before they create friction.

Here's what you need to look out for:

1️⃣ Shared context is missing
↳ The team has different assumptions about goals, constraints, or priorities.

2️⃣ Language lacks precision
↳ What you say might make sense to you, but could be interpreted differently by others.

3️⃣ Signals are inconsistent
↳ Messages from different people or teams don't align, causing confusion.

4️⃣ Understanding isn't verified
↳ Leaders assume everyone's clear without making sure.

5️⃣ Accountability isn't explicit
↳ Next steps and who owns what are implied, not explicitly agreed.

6️⃣ Silence is mistaken for alignment
↳ It can be a signal of hidden doubt rather than agreement.

7️⃣ Communication doesn't translate into action
↳ Even though information is shared, the outcomes don't reflect the main intent.

If you ever spot these patterns, here's what helps:

Set context before diving into details
↳ Make sure everyone understands the "why" before discussing the "what".

Create space for questions
↳ Let your team know you want to hear their opinions on things.

Connect communication to outcomes
↳ End meetings with clear goals and ownership so everyone knows their role.

Most communication problems can be solved before they turn into a huge issue.
Pay attention to the signals that show misalignment,
and don't be afraid to follow through and make things clear.

What's the biggest problem in communication you've seen? How did it get solved?

For more posts on strengthening team communication, follow Clif Mathews.

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📨 Every week, 14,000+ execs learn how to define their own success in my newsletter, The Second Summit Brief.
Sign up here so you don't miss out: bit.ly/SecondSummitBrief

🔁 Repost to help another leader spot when communication is breaking down.

"You can do anything but not everything."

Reading that changed how I prioritize.

I've seen many execs who mistake a packed calendar for meaningful work.

They're busy at all hours, responding to every request, and checking every box.
But when I ask what they're most proud of, sometimes it's a struggle to answer.

That disconnect is what Greg McKeown's book, Essentialism, talks about.

His lessons have shaped how I work and how I help leaders with their prioritization.

Here's what I'm holding onto:

1. If you don't pick your priorities, other people will.
2. Essential is a higher standard than important.
3. Every "yes" has a cost, whether you like it or not. 
4. Say no, edit commitments, and uncommit sooner.
5. Protect your execution by building buffers and removing obstacles.

McKeown also defines the essentialist cycle to help with workflow.

It looks like this:

🚶‍➡️ Explore
↳ Make space to think. Look for the highest leverage option.

🙅 Eliminate
↳ Say no. Remove what doesn't make the cut.

💪 Execute
↳ Make the essential easier to do with routines and guardrails.

Underneath it all is a simple idea:

You don't "find" time.
You create it by removing what's not essential.

If you keep trying to find time, you tend to:

❌ React fast and regret later.
❌ Say yes to be helpful or avoid discomfort.
❌ Treat everything like it's urgent.
❌ Measure value by a full schedule.

But when you focus on what's essential, you:

✅ Pause long enough to choose what's important.
✅ Use clear criteria for commitments.
✅ Build boundaries that protect your focus.
✅ Measure value by impact and meaning.

But even as you're practicing this new habit,
there are a few traps that are easy to fall into:

🚩 The "yes" habit
↳ Without a strong criteria, you say yes to whoever asks best.

🚩 The success snowball
↳ More options can pull you away from what mattered first.

🚩 The busy badge
↳ Activity can feel productive while avoiding the real work.

🚩 The no buffer calendar
↳ One surprise turns a packed week into chaos.

🚩 The willpower plan
↳ If your system depends on discipline every day, it won't survive real life.

I'm still getting into better habits myself.

Sometimes I protect my calendar well, other times I find myself reacting a lot.

But with practice, any leader can start protecting the work that's really important to them.

Have you read this book?
I'd love to hear what you all think!

For more posts on staying focused on meaningful work, follow Clif Mathews.

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📨 Every week, 12,000+ execs learn how to define their own success in my newsletter, The Second Summit Brief.
Sign up here so you don't miss out: bit.ly/SecondSummitBrief

🔁 Repost to help another leader prioritize their time.

Stop competing for awards that don't exist.

You won't get extra credit for being exhausted.

Most leaders chase invisible metrics without realizing it.

And the worst part is, most of them are disguised as dedication.
When we keep chasing them, it feels good because it "proves" you're successful.

But for most people, they reach a point where it just stops working.

The wins aren't as fulfilling.
The idea of climbing higher doesn't motivate you.

You ask yourself, "do I want to keep going down this path?"

The triggers for this realization looks different from person to person.

Here's how that misalignment often comes up:

Tried the hardest
↳ You're exhausted, but no one asked you to prove yourself this way.

Accepted the least praise
↳ You've trained people not to recognize your work.

Put in the most hours
↳ Your presence became your main metric instead of impact.

Made zero errors
↳ You stopped taking meaningful risks.

Exceeded absolutely everyone's expectations
↳ You're living for external validation, not what feels right for you.

Most leaders ignore these thoughts, and just try to push through it.

But if any of these feel familiar, it's worth pausing and taking a step back

It creates space for you to ask,
"Is this what I actually want? Or just what I've proven I can do?"

I'm going into this more in my newsletter tomorrow.

I'll be exploring what leaders can do when they're facing this hurdle.

If you're not subscribed yet, sign up here so you don't miss it:

bit.ly/SecondSummitBrief

For more posts on redefining what success means, follow Clif Mathews.

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📨 Every week, 14,000+ execs learn how to define their own success in my newsletter, The Second Summit Brief.
Sign up here so you don't miss out: bit.ly/SecondSummitBrief

🔁 Repost to remind another leader to stop competing for awards that don't exist.

Every great leader goes through high-pressure moments.

How you handle them shapes your impact.

Some leaders might freeze up. Others rush into the wrong solution. 

And your response to it can improve with practice.

The leaders who thrive even in high-pressure moments aren't necessarily smarter.

They've developed a set of skills that are crucial when things get intense.

Here's what that looks like in practice: 

1️⃣ Judgment
↳ Pause to separate important signals from noise in key moments.

2️⃣ Decision Framing
↳ Make it clear who owns what, any limitations, and potential outcomes.

3️⃣ Clarity in Communication
↳ Say what matters without overexplaining.

4️⃣ Influence
↳ Add your perspective on things respectfully and thoughtfully.

5️⃣ Presence
↳ In high-stakes moments, staying steady is a sign of confidence and calm.

6️⃣ Emotional Regulation
↳ Manage your internal reactions before they extend to everyone else.

7️⃣ Follow-Through
↳ Make sure decisions become sustained actions. That's what makes you reliable.

8️⃣ Learning Agility
↳ Always look out for opportunities to learn, even as you climb up the ladder.

If you've ever snapped under pressure,
that doesn't make you a bad leader.

It's happened to everyone at some point.

What matters most is building up the right skills so you're prepared for the future.

Focus on them one at a time, 
and you'll become the leader who stays calm in any situation.

Which one of these skills do you think is hardest to embody?

For more posts on leading in high-pressure moments, follow Clif Mathews.

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📨 Every week, 14,000+ execs learn how to define their own success in my newsletter, The Second Summit Brief.
Sign up here so you don't miss out: bit.ly/SecondSummitBrief

🔁 Repost to help another leader strengthen their response to pressure.

Keynotes look effortless.

That's how you know they took real effort.

I've been giving keynotes for decades, and the most common assumption is:

"So you just talk for an hour, right?"

Not exactly.

From an audience's perspective, yes,
you get on stage and speak for an hour.

But there's a whole lot more that goes into making it work.

Every part of the process is important:

✅ Audience research.
✅ Storytelling and structure.
✅ Energy management.
✅ Hours of practice.
✅ Travel and logistics.

Not to mention the years of experience that inform the speech in the first place.

All of that happens before, during, and after the "one hour" people see.

It's a lot of work, but I love it.

When you do it well, you give an audience clarity, 
perspective, or tools they didn't have before.

People hire keynote speakers to help talented audiences see problems in a new light.

And that's because of the work put in before even touching the mic.

So yes, speakers talk for an hour.

But the value lives in all the work that makes that hour matter.

If you've ever spoken at an event,
what's one thing people don't realize goes into it?

For more posts on public speaking (and extra techniques), follow Clif Mathews.

If you're curious to hear more about my keynotes head here 
👉🏻 https://lnkd.in/eVzVnrtK
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🔁 Repost to help other people understand what goes into creating real value on stage.

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