Thirty-one thousand!!!
That’s bigger than the hometown where I grew up.

For years, I’ve been calling that my network.
Except I realized something recently.

It’s not my network. It’s 31,000 people who at some point in their life clicked a button.

And that’s it.

For most of them, our entire relationship consists of about an eighth of a second of effort on their part to click the button, and an automated email reply on my part.

And then I sit around wondering why more people aren’t reading my articles, commenting on my posts, or engaging with my newsletter.

We’re Rewarded for Collecting People

If you’re the same as me with this, let me tell you the same thing I told myself.

You’ve barely engaged with the people. So why the hell would you expect them to engage with you?

And that’s when I realized you and I have been thinking about networking completely wrong.

Think about all the networking advice you’ve heard over the years. Grow your network. Make more connections. Meet people. Collect business cards. Follow up on LinkedIn.

We’re literally rewarded for collecting people.

Until you get 500 connections, it’s not even mentioned.
5,000 connections is a little better.
But if you have 30,000 people following you, holy cow, you must be really well connected.

But that’s bullshit.

I mean, what are you connected to?

I can have 31,000 people in my contacts and still have absolutely nobody to call when I need help with something. Because having someone’s name in a database doesn’t mean I have a relationship with them.

It means I have their name in a database.

And somewhere along the way, we kind of started confusing the two of those things.

The Part I Love

Here’s what bothers me the most about this.

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The worst part about being rejected isn’t getting rejected.
It’s what you do after.

You replay the conversation in your head and think about all the things you could have said differently.

You wonder whether you asked for too much money, whether you came across as too timid, or whether you just sounded like a complete asshat.

And then, based on those pesky voices who just won’t shut it, you start changing the way you do things.

Maybe you lower your price or rewrite your pitch or work with less confidence than you used to have. Whatever it is, you change your entire approach.

All based solely on the reason they gave you when they said “no.”

Here’s the problem: That might not be the real reason.

Maybe they turned you down because of a limited budget, but in reality, they didn’t think you were worth the money.

Maybe they said you weren’t the right fit, but actually, they just don’t like you.

Or maybe they told you the truth.

You don’t know the reason for the no. And that’s why it’s so hard to learn the right lesson from rejections.

Most people don’t enjoy telling someone why they really rejected them. Because it’s usually uncomfortable. And embarrassing.

It’s so much easier to give an answer that doesn’t hurt anyone’s feelings.

I’ve been on both sides of these conversations. I’ve been rejected a lot of times, and I’ve had to reject a lot of people a lot of times.

And I can say, for a fact, that what is being thought isn’t always what gets said.

Which got me thinking.

What if you could go back and have that conversation again?
Except this time, the person who rejected you had absolutely nothing to lose by telling you what they really thought.

That’s why I built this AI prompt.

It asks you 6 questions about what happened. Then it pretends to be the person who rejected you.

You get to question them. Push back. Find out where things might went wrong.

And when you’re ready, you can ask the AI to stop playing that person and tell you what you maybe want to learn from the experience.

Will it know exactly what the other person was thinking? Of course not. Don’t be silly. But I use it, and every single time it gets me to think in ways I didn’t think before.

This prompt will help you recognize something you haven’t already recognized.

And maybe, just maybe, it can quiet some of those pesky voices in your head.

Run the prompt. Find out why they said no. 👇🏽👇🏽

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I stumbled on Kondo and I’m in love.
LinkedIn really needs to buy this company and use it for it’s DM-ing.

They aren’t paying me to say this. I’m just telling you.

If you’re frustrated with LinkedIn DM, get a free month of Kondo on me.

Some of the largest companies in the world pay me to be a part of their brainstorms.

Kraft brought me into a room with their executives to figure out their next sandwich idea.

eBay had me help shape their youth marketing strategy.

Nestle had me help with ideas on how to make some of their candy more relevant.

I’ve done similar things with Sony, Citi, Nike, USA Today, Universal. And the list goes on.

I’m telling you, I kill it in a brainstorm.

Executives have referred to me as one of the most creative people they know.
But here’s my secret:

I’m not.

I’m rarely the smartest person in the room.
I’m often the least creative.
And I’m almost always the one who knows the least about the product.

So why do they keep inviting me back?

Because I'm not in the room to come up with ideas.
I'm in the room to fix the room.

Why Brainstorms Don’t Work

The multi-billion dollar ad agency BBDO was born when four guys got together. Three had last names that started with B, B and D. The fourth was Alex Osborn.

But Osborn’s most popular achievement isn’t as co-founder of BBDO. Because was the person who invented the brainstorm.

His premise seems obvious now: Put a group of people in a room, ban criticism, and they’ll come up with better ideas - and more of them - than if they tried to do it alone.

Everyone loved it.
It seemed to work.
He even wrote a book about it

Now here we are, 80 years later, and the brainstorm is still going strong.

There’s only one minor problem.

Research continues to prove that group brainstorming doesn’t work.

It produces fewer ideas, and lower-quality ones, than if the same people worked alone and then pooled their results.123

So what the heck is going wrong with the brainstorm?

As it turns out, there are a few things. And it starts with something called Production Blocking.

What The Hell Is Production Blocking?

The nice thing about brainstorming in a group of respectful people is that when somebody talks, everybody else listens, and waits their turn to speak.

As it turns out, that’s not just nice - it’s also not helpful.

Because as you’re listening to others speak, your idea just sits there. Maybe you forget what it is before you even say it. Or the conversation moves on and it just doesn’t feel right to share anymore.

This is called production blocking, and it’s why some of the best ideas in most brainstorms never get shared.

But that’s not the only problem.
There’s also a problem with hierarchy.

In the 1970s, sociologists found that the people in the room with the most status do the most talking. Fifty years later, it still happens. They’re still talking.

But it’s not just about the amount of time they speak. It’s about their ideas.

Because of their status, their ideas get weighted more heavily than other people’s ideas. It doesn’t even matter whether or not they’re better.

Pay attention to these two things in your next brainstorm. You’ll see both of them happen.

The good news is that there’s a way around it.

And that’s my secret.

How To Fix The Room

As I said earlier, I’m not invited into the room to be the person with the best ideas.

I’m in the room to fix the room.

The ideas aren’t broken. The room is.

And there are two things I do that make the difference between an amazing strategy session and a grand waste of time.

Antidote #1: Ask the right questions to get the best ideas

Most brainstorming sessions start with someone asking, “What ideas do you have?”

And then there’s that awkward silence until everyone starts talking.
Well, not everyone.

Usually a few people start (we all know who they are), while everybody else listens, waits their turn and tries to remember that brilliant thought they had three minutes ago.

But that’s the wrong way to start, and the wrong question to do it with.

I do something different.

I get people thinking about the same problem before anyone starts sharing their answers. And it starts with better questions than “what ideas do you have?”

The goal is to get people to think differently right out of the gate. I do that by challenging them with questions like:

If we could do anything, what could we do that would scare the shit out of our competitors?

or

What would have to be true for us to completely own this market?

Then I give everyone a few minutes to quietly think, and write down their answers.
Individually.

No talking. No interruptions. No waiting for the loudest person to finish their brilliant monologue.

Everyone gets to develop their own ideas before the group starts influencing them.

Because the best way to get more ideas out of a room is to stop making everyone compete for the opportunity to share them.

And once everyone has their ideas down, that’s when the real discussion begins.

Antidote #2: Find the ideas that are hiding scared

Here’s something I’ve learned after sitting in hundreds of these meetings.

The person doing the most talking is rarely the person I’m most interested in hearing.

I’m looking at the people who aren’t talking.
Especially the ones who’s eyes look like they have something to say.

I led a strategic brainstorming session a few months ago with the leadership team of a $300 million company.

We were having a pretty good discussion about growth strategies.
But while everyone was talking, I noticed something.

The CTO was silent.

We weren’t discussing technology, so nobody really expected him to contribute much. But I kept watching him.

His eyes were doing a hell of a lot more talking than his mouth.
So I stopped the conversation and asked his opinion.

He said six words.

“Why don’t we just acquire [partner company]?”

The room went silent.

Not because it was a bad idea.
Because nobody else had even considered it.

And the more we talked about it, the more obvious it became that this was a great idea - and something worth exploring.

Six months later, they finalized the acquisition. They now expect it to increase revenue by 40%.

All because of six words that almost never got spoken.

And here’s the part that nags at me.

That idea was already in the room ready to be said.
It didn’t need to be invented. It just needed to be heard.

That’s what happens in brainstorms. It convinces some people their ideas are more important and makes others believe that their ideas aren’t worth sharing.

Most people don’t even realize it’s happening. Which is why I spend so much time watching the people who aren’t talking.

Most of the best ideas I’ve “had” in brainstorms weren’t mine at all. I just find the corner they’re cowering behind and encourage them out.

Some days it feels like the greatest con I’ve ever pulled.

It isn’t.
It’s the whole job.

The Single Worst Way To Kill A Room

Now, you might be thinking you don't have the luxury of hiring a business consultant like me to facilitate every meeting. Fair enough.

But there's one thing you can do yourself that’ll make an enormous difference. And it's probably the opposite of what you normally do.

Think of the brainstorming meetings you’ve been a part of. I’m sure this one exists:

The energy is good. The ideas are flowing.

Somebody says something really interesting and, before it’s discussed further, the most senior person in the room opens their mouth and says, “What if we...”

And everything changes.

The energy of the room shifts and everybody knows it but the leader.
Heads nod.
Mouths close.
Every new idea is suddenly a version of the boss’s.

Nobody decided to change the dynamic. It’s just what happens when hierarchy gets in the way.

If you’re a leader, you probably think your job in a brainstorm is to come up with the best idea.

You’re wrong.

The moment you share your ideas, it becomes a magnet. Suddenly the entire room is brainstorming ways to make your idea work

In a brainstorm, being the smartest person in the room isn’t an asset. It’s the most dangerous person in the room.

What To Do Instead

So here’s what I want you to try in your next brainstorm.

Don’t ask, “What ideas do you have?” Ask a question that makes the whole room think deeper.

Watch the people who aren’t talking. Especially the ones whose eyes are.

And if you’re the most senior person in the room, talk last. Or get the hell out of the room.

Six words from a quiet CTO changed an entire company. Now think about how many six-word ideas have died in your meetings because someone more important spoke first.

The best brainstormers aren’t the ones with the best ideas.
They’re the ones who make sure the best idea gets said.

So don’t try to fix the brainstorm.
Fix the room.

P.S. The CTO who said those six words? He almost didn’t say them. The first time I asked, he said “it’s nothing.” I actually had to ask him twice. Think about that the next time you skip around the table.

He says things like, “I just tell it like it is,” and “people always know what I think about them.”

He says these things like they’re describing one of his greatest strengths.
And maybe it is.

Or maybe he’s just an asshole.

Okay, that’s a little harsh.

But I’ve worked with a lot of leaders who pride themselves on being direct, and I’ve noticed something kind of interesting about them.

They’re often so focused on telling the truth that they don’t pay much attention to whether anybody’s actually listening to them.

The Other End of the Spectrum

And then there are the people at the complete other end of the spectrum.

They’re the ones who will do just about anything to avoid an uncomfortable conversation.

I bet you know your fair share of those people too.

They soften their feedback so much it sounds more like praise than constructive feedback. They’re the ones who tell you everything’s fine when it’s clearly not.

The building’s burning, but they call it being nice.
Wrong.

So what I’m saying here is that there’s one group of people that confuses honesty with effectiveness, and another group that confuses kindness with avoidance, and both of them are really screwing up communication.

The Problem with Being Direct

Here’s the problem with being direct.

Have you ever had someone come to you with a problem and you immediately know what they’re doing wrong?

Of course you have, because it happens all the time.

Think of the person who is complaining about their colleague, or about how they screwed up a project.

You can see pretty clearly the role the person played in making that problem happen.
So you tell them.

You explain exactly what they’re doing wrong, why it’s happening, and what they need to change about themselves.

And you’re absolutely, positively, a hundred percent right.
Congratulations.
You just accomplished absolutely nothing.

Because the person wasn’t coming to you for an explanation of all their behavioral failures and personality quirks. They just needed to vent.

They needed someone to understand why they were upset before they could start thinking about what they should do differently.

But you didn’t bother figuring that out, did you?

You just started talking. And then when they got defensive or shut down, you convinced yourself that they just aren’t able to hear the truth.

You know what?
Maybe you’re just not very good at delivering it.

The Problem with Avoiding Conflict

Now before all the conflict avoiders out there start feeling like you’re doing it better than the direct people — you are not off the hook yet.

I know leaders who’ll spend 45 minutes practicing what they’ll say to tell someone they’re not doing a good job. And after all that rehearsal, they’ll just end up saying something like, “I think there might be an opportunity for you to be a little more proactive sometimes.”

What the f**k does that mean?!

You’ve got an employee who’s consistently missing deadlines and you’re talking about opportunities to be more proactive. Just tell them they’re missing the f***ing deadline!

Because when you’re afraid to be direct, the other person is just going to walk away thinking everything is fine while you walk away thinking you’ve addressed the problem.

And then three weeks later, when nothing has changed at all, you’re going to be frustrated that they didn’t listen.

They didn’t listen because you didn’t actually say anything!

Avoiding the truth doesn’t protect people. It actually just takes away the opportunity for them to do something about it. And if you’re their leader, you failed at your job.

I’ve worked with leaders at both ends of the spectrum — both direct people and non-direct people — and I’ve realized that there’s a solution for both types. They’re both actually missing the same thing.

It’s this.

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You can’t practice for a tug-of-war without somebody on the other side pulling back.

But that’s exactly how most of us prepare for difficult conversations.
We rehearse what we’re going to say.
We work through our arguments.
We imagine all the brilliant responses we’re going to give when the other person pushes back.

And, of course, we always win.
Because we’re playing both sides.

We think we’re preparing for a conversation. We’re actually preparing to deliver a speech.

And there’s a big difference between the two.

But I figured out a solution.
I figured out how to have the entire conversation before actually having the conversation.

And it’s already saved me from making a fool of myself.
Here’s what happened.

I’ve got a meeting this week with a publisher about my upcoming book.

I’ve been thinking about this conversation for weeks. I know what I want. I know why it makes sense. I’ve got my arguments all worked out in my head.

So I built an AI prompt to play the publisher.
And I had the conversation three days before the actual conversation.

It sucked.
She asked questions I hadn’t thought about at all.
She challenged my assumptions that I fully believed were reasonable.

I even gave a long monologue that had sounded brilliant in my head, and like complete buffoonery when it came out of my mouth.

Which is exactly what I needed.

Because now I can change what I plan to say.
And I can try it again.
And again.

And here’s my favorite part.

Whenever the conversation starts going sideways, I just type three words:

I LOVE PIZZA.

AI immediately drops the character and tells me what I did well, what I screwed up, and what I should do differently.

Then I can jump right back into the conversation.
Or start over.
Or make the person even more difficult to talk to.

I dare you to try doing that with your boss.

So what’s your next big conversation?

Maybe you’re asking your boss for a raise.
Maybe you’re confronting an employee who’s not performing.
Maybe you’re pitching an idea to someone who has already told you no.

You can keep rehearsing both sides of the conversation in your head.
Or you can finally find out what happens when someone pushes back.

Here’s the prompt. 👇🏽

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You’re always practicing something.
You usually just don’t know what it is.

Let me explain.
And we’re going to start with my knee.

After decades of long distance athletics, my knee finally quit on me earlier this year.

It’s all fucked up.
ACL tear. Deteriorated cartilage.
I could barely haul myself up a small set of stairs.

I had to stop running.
Stop cycling.
And basically stop doing all the things that would keep my wife from wanting to punch me in the face.

The thing is, none of this should have surprised me.

But it did.

25 years ago I learned I have a double tarsal coalition in my right foot. That’s the technical term for “bones stuck together”, because I know you like your technical terms.

Basically, my right foot flares out when I run.
The doctors told me, “We’re amazed you can run. Keep running.”

So I did.

The foot issue wasn’t causing me any problems, so I barely paid attention to it. Eventually, I forgot about it altogether.

Then came the injuries.

One year, I hurt my calf and couldn’t run for two weeks.
The next time, four weeks.
Then six. Eight. Twelve.

Each injury took a little longer to heal. And each one seemed to happen a little sooner than the last.

But eventually I’d recover and go right back to my long-distance malarkey.

I told myself I was overtraining.
Or I had bad luck.
Or injury was simply the price you pay for doing hard things.

Regardless, I believed every workout was making me a better runner.

I was wrong.

I thought I was practicing running.
I was actually practicing running wrong.

Every step reinforced the same bad movement.
My foot flared out.
My leg compensated.
My knee twisted in a way knees aren’t particularly fond of twisting.

And I did it over and over again. Through millions of steps. For decades.

Until eventually my knee waved the white flag and said, Fuck this. I’m done.

You’re Confusing Experience With Expertise

Most people believe that if you do something enough times, you’ll get great at it. Log enough hours and eventually you’ll be a master.

Turns out that’s not true.

In 2005, researchers at Harvard Medical School1 reviewed a bunch of studies that measured the level of care doctors give to their patients. You’d assume the more experienced a doctor was, the better care they gave.

Nope.

More than half of the studies found that the more years a doctor practiced, the worse their quality of care.

Crazy, right?
I know.

Experience alone doesn’t make you better.
It only makes you better at whatever you were practicing.

Think of it as the difference between 20 years of experience, and one year of experience that you’ve repeated 20 times.

Practice Doesn’t Make Perfect

I know what’s going on in your mind. You’re thinking of that 10,000-hour rule, aren’t you?

I see you.

In case you don’t know the rule, it is based on research from Anders Ericsson, and claims that if you put 10,000 hours of practice into something, you’ll become world-class at it.

Unfortunately it’s wrong.
Even Anders spent years pushing back against it.

The hours were never the point of his work. What matters most is not the amount of time you practice, but how you do it.

10,000 hours of doing something wrong doesn’t make it right.
Just ask my knee.

You’ve heard the saying, “Practice makes perfect.”

It doesn’t.

Practice makes permanent.

What Are You Practicing?

You’ve probably got a lot of experience. Five years of doing your job. Ten years of leading people. Twenty years in your industry. Whatever.

Let’s look at the things you’ve actually been practicing during that time.

Every time you avoid a hard conversation, you’re practicing avoidance.
Every time you check your phone in a meeting, you’re practicing distraction.
Every time you let someone miss a commitment without addressing it, you’re practicing a lack of accountability.

None of those things feel like practice.
They just feel like…. any old Tuesday.

You stop noticing it because it’s just how you do things. Just like how I stopped noticing that my foot flares out and twists my knee.

But every time you repeat one of those things, its a rep.
And the reps add up.

That’s why you can have twenty years of leadership experience and still be a crappy leader.

That’s the bad news.
But, don’t worry, it gets worse.

Your Warning Signs Are Already There

Your warning signs have probably already been there.
Mine definitely were.

First, I was injured for two weeks.
Then four.
Then six.

And each time, I came up with a perfectly reasonable explanation for it.

Overtraining. Bad luck. Getting older.
Anything other than admitting that the way I was practicing running might be the problem.

You do the exact same thing.
But your warning signs are a little different.

Maybe your team gets a little quieter.
People stop challenging your ideas.
Maybe a good employee leaves. Then another one does.

You tell yourself it’s the job market. Or a bad hire. Or a rough quarter.
And maybe it is.
Or maybe it’s your version of my foot flaring out.

The problem isn’t that you don’t see the consequences. It’s that you’ve gotten really good at explaining them away.

And every time you do, you go back to practicing the exact behavior that’s causing them.

But I’m telling you, when you’re really good at doing things wrong, something is eventually going to break.

So Here’s The Question

Forget how much experience you have. Let’s pretend that doesn’t matter.

Just tell me, what did you practice today?

Not what you meant to practice. What you actually did. Over and over. Without thinking about it.

Because that’s the thing you’re getting better at.

And if you keep practicing it, don’t be surprised when you get really fucking good at doing it wrong.

Because that’s when everything breaks.

What I’ve learned is that there are a bunch of people out there building really interesting businesses these days.

Some days I’m spending seven hours on calls, back to back, with people I didn’t even know a month ago.

And I’ve noticed something that’s driving me absolutely bonkers. Almost every conversation ends the same way.

I ask, “So how can I help you?”

And they respond with some version of, “Promote my business and send me your clients.”

Seriously?!
We met 30 minutes ago, and you want me to promote your business and send you my clients?

I don’t even know if you’re any good at what you do.
Heck, I don’t even know what you do.

The Advice Everyone Gives

I know where this ask comes from, because every sales coach, sales book, and sales podcast, they all tell you the same thing.

Be direct.
Be specific.
Tell people exactly what you need.
If you want a referral, ask for the referral.
If you want business, ask for business.

And I think that’s bullshit advice.
At least it is when you’re talking to someone you just met.

Because asking someone you just met to promote your business and send you clients is like the business equivalent of proposing after the first date.

We just had a cup of coffee.
I don’t even know if I like you yet, and you’re asking me to marry you?
What the fuck?!?!

What You’re Really Asking For

So here’s what I think people completely misunderstand.

When you ask someone you just met to promote your business and send you clients, you think you’re asking them for help.

You’re not.

You’re asking them to take a risk, and it’s a much bigger risk than you probably realize. Because what you’re really asking them for is something you haven’t earned yet.

You’re asking for…

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It’s time to tell the world how great it is.

But Jeff Bezos figured out something interesting a long time ago.

We’re doing it backwards.

At Amazon, they started writing the press release before building the product. Which sounds a little ridiculous at first blush.

I mean, how the hell are you supposed to announce something that doesn’t even exist yet?
Turns out, that’s exactly the point.

Because if you can’t explain what you’re building, who it’s for, and why anyone should give a shit about it, you probably shouldn’t be building it in the first place.

And if you can’t come up with a compelling headline, Well, maybe your big idea isn’t quite as big as you think (a devil’s advocate may help)

I love this approach. Because I have a tendency to get excited about new ideas. Lots of them. All the time. And sometimes I get so caught up in the excitement of creating something, that I forget to ask whether it’s actually worth creating.

And that’s why I built this AI prompt.

It asks you five simple questions about the thing you think you’re building. Then it writes the press release announcing it’s successful launch.

You can use this for a new product, a service, a workshop, a book, a career move. Anything where you want to figure out what success looks like.

We both know you don’t have time to write the press release any more than I do.

I gotchoo.

Write the ending first. Then go build it. 👇🏽 👇🏽

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There are only three problems in life.
That’s it, just three.

I don’t care how complex or unique you think your difficulties are - what I’m telling you is that they can all be boiled down to one of three problems:

1. Your head

2. Your heart, or

3. Your bank account.

Let me explain.

We’ll start with the problems in your head.

The Problem Is In Your Head

We all have problems in our heads.

The question isn’t whether you have this type of problem - the question is how much the problems in your head are limiting you from being the person you want to be and doing the things you want to do.

Here’s what I mean:

• Do you ever doubt yourself or identify with imposter syndrome?

• Do you wish you were spending your life doing something else?

• Have you ever struggled with decision-making - or avoided tough conversations?

Yeah, I thought so.

These are all problems in your head.
See, I told you have head problems.

Head problems are challenges with your intellectual reasoning. They manifest themselves as things like confusion, decision paralysis, and/or a desperate need to be right.

Your ego? That’s a head problem.
Your tendency to take on too many things? That’s also a head problem.

When people get stuck in their heads, they end up creating more confusion than clarity.

That’s the primary symptom to look for when diagnosing head problems: increased confusion.

As an example, think of that entrepreneurial leader you know. The one who can use some founder coaching because they change their priorities every few days.

Or how about that person who thinks it’s more important to over-analyze than to just make a gosh darn decision.

For both of them, the problems are in their heads.
And, in the end, they just create confusion which destroys productivity and progress.

If you are a person who is dragged down by problems in your head, here’s my advice:

• Stop waiting for certainty - it’s not coming.

• You’ve got to practice being okay with the grey zone. Acknowledge your discomfort, even though it feels uncomfortable. You’re going to get over the discomfort, I guarantee it.

• Do the thing you really know deep inside that you’re supposed to do. You’ll be a better person on the other side.

And that brings us right to the second problem: the problems of your heart.

The Problem Is In Your Heart

People who struggle with problems of the heart are often stuck in a place of resentment, fear, sadness, or some other similar emotion.

Whereas the problems of the head are intellectual challenges, the problems of the heart are emotional burdens that feel like the weight of the world in the pit of your stomach.

• Do you feel out of sorts when somebody doesn’t like you?

• Do you feel like you aren’t appreciated when you’re left out of a meeting or get-together?

• When you get constructive feedback, does it feel like the world is collapsing in on you?

If any of these things resonate, you’ve got some problems of the heart.

People who have problems with the heart don’t hold their team accountable because they don’t want to hurt their feelings.

They take things personally when it’s not about them at all.

They make rash decisions driven by emotions. Like that passionate email you sent that you regretted the next day.

Heart is important, but it can’t lead a team on its own. You can care deeply, that’s ok, but you also have to lead firmly. You have to set boundaries.

You have to separate the emotional from the intellectual. Because emotion sucks at making decisions on its own. And emotion really sucks at building out a strategy.

So if you are plagued by problems of the heart:

• Remind yourself that it’s important to make decisions from the intellectual brain, not the emotional one.

• Talk to someone, get a leadership coach, journal it out - get the support you need to help you understand when you’re about to make rash emotional decisions.

And that leaves one more problem: your bank account.

The Problem Is Your Bank Account

Bank account problems are resource issues.

Keep in mind, I’m not just referring to money problems. Even people with more than enough money have bank account problems.

Instead, bank account problems are about time constraints, lack of tools, capacity problems, or, yes, finances.

• Do you wonder why you’re spending your time working late every day?

• Are you not hiring more people so you can maintain your current profit margin?

• Do you feel like you’re too busy to fix the things that are making you too busy?

Those are all bank account problems.

When you create an excuse and pretend it’s reality - that’s usually a bank account problem.

When you tell people to work harder because you believe they can get it done on their own - that’s a bank account problem too.

When you haven’t taken more than a week’s vacation in 5 years because you can’t possibly understand how the world can keep revolving without you. Yup, bank account problem.

Sometimes the bank account is actually an issue, but oftentimes it’s just a convenient scapegoat.

So here’s what I’m suggesting you do.

• The challenge isn’t that you have constraints - the challenge is that you need to get creative with them.

• Think of how you can trade the resources you have for the ones you don’t.

• Dig deep inside and ask yourself if you really have a resource issue, or if you are simply avoiding making a harder decision.

The Diagnosis You’ve Been Skipping

We all have problems. That’s not the problem.

The challenge is figuring out which problems are of your own making and which are actual obstacles standing in your way.

That’s why I boil all issues down to these 3 problems in life: your Head, your Heart, your Bank Account.

The faster you diagnose which category your issue falls into, the faster you can move forward in resolving it.

Most leaders waste months solving the wrong problem.

They throw money at what’s really an ego issue.

They read leadership books when they should be setting boundaries.

They call it “lack of resources” when it’s actually “lack of courage.”

Head. Heart. Bank account.

Which one are you actually dealing with right now?

PS — Which of the three nags at you the most? Tell me in the comments.

There are a bunch of things I’ve done in my life that have absolutely no business being on my resume.

I worked at the concession stand at a movie theater.
I was the worst employee at the Gap in my hometown.
And I was even a gift wrapper during the holidays when I didn’t know how to do gift wrapping and didn’t even have the patience to learn it.

I’ve had jobs I completely sucked at.
I started businesses that went nowhere.
I’ve been fired.
I’ve made decisions that, when I look back on them, really make me question whether my brain was actually fully developed at the time.

None of those things are particularly impressive.

But I started to realize something.

Some of the least impressive things I’ve done in my life may be responsible for some of the things that I’m actually the best at today.

Which is kind of f***ed up when you think about it.

Because we spend our entire careers doing just the opposite of that.

The LinkedIn Version of Your Life

We look backward on our life and we decide which experiences count.

Were you a CEO? Yeah, that counts.
Did you sell a company? That definitely counts.
Did you work with some giant brand that everyone recognizes? Yeah. Put that shit in bold on your resume.

But did you work as the popcorn guy behind the counter in a movie theater?
Maybe that doesn’t go there.

As I thought about this, I actually noticed that I do this all the time, and very blatantly.

I tell people that I’ve started 3 companies and each was acquired by a large public conglomerate. What I don’t say is that there was a fourth company. And that fourth company was doing well. Until it went out of business and I had to fire 35 people in one day.

I think we treat our lives like LinkedIn profiles. We keep the impressive stuff and kind of omit everything else from the conversation.

But that’s a mistake.

Because sometimes the stuff you omit is exactly where your advantage comes from.

Ben Langner’s Post

I came across a post recently on LinkedIn from Ben Langner, who is a VP of HR at Wilson. He wrote: “That job you leave off your resume might be why you’re so damn good at HR.”

I read that and thought, holy shit, Ben’s right.

And that’s what led to this little rant here. Because I think the idea goes way beyond HR.

There are probably things you’re unusually good at today because of experiences in your past that you’ve completely disregarded. You just haven’t connected the dots yet.

So let’s do it right now together.

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You see, I’ve been working on a new business idea lately. I like the idea.

A lot.

Which is exactly the problem.

Once you fall in love with an idea, you become the worst person to assess how good it is. You just start looking for evidence that it’ll work instead of evidence that it won’t.

And AI can make this worse.

Tell ChatGPT about your brilliant new idea and it will treat you like the smartest person in the universe.

“That’s the best idea I’ve ever heard from you!”
“Brilliant! Here are 5 ways to make it even better!”

But I don’t need my butt kissed.

What I need is someone who is trustworthy trying to kill the idea before I waste six months learning the hard way that I should have killed it myself.

So I created a prompt that does that.

It asks AI to figure out who the right person would be to challenge your idea. Then it becomes that person.

This isn’t a generic devil’s advocate.

It’s an actual subject-matter expert with the experience to know how ideas like yours tend to fail.

Then you debate them.

They push.
You defend.

They challenge your assumptions.
You push back.

And if you give them a bullshit answer, they will not politely move on. They will tell you it’s bullshit.

And here’s the part I really like.

The AI isn’t allowed to tell you whether it thinks your idea is good.
Not yet.

You have to respond thoughtfully to it’s feedback. After all, it’s the same feedback you’re going to get from potential users and customers.

The difference is, your users won’t be direct with you. The devil’s advocate will.

Then, when you’re done with the debate, you type one word:

Watermelon.

That ends the debate.

AI steps out of character, looks at everything you’ve argued, and tells you what it actually thinks.

It analyzes the strongest cases for and against your idea. How it could succeed and how it would fail.

And it tells you what you have to do to make it work.

I used it yesterday.
It’s amazing.
It changed the entire way I’m thinking about the business I’m building.

If you have an idea - any idea - you shouldn’t move forward without this.

Create your own devil’s advocate 👇🏽

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After college, I knew exactly what I wanted to do.

I wanted to be in the music business.

Through a series of events that are better told over a bourbon, I got connected with Jimmy Iovine when I was 27.

If you don’t know the name, Jimmy Iovine is one of the most influential people in the history of the music industry. He’s produced and advanced the careers of more superstars than you can imagine, including John Lennon, Bruce Springsteen and Tom Petty. On top of that, he co-founded Interscope Records, and started Beats with Dr. Dre, which Apple acquired for $3 Billion.

Jimmy and I sat down and talked for awhile.

It was a great conversation. He actually told me I reminded him of himself when he was younger.

To this day, that may still be the greatest compliment anyone has ever given me.

The next week, Jimmy invited me to a get together at his house.

I never went.

Yep. You read that right.
I didn’t go.

One of the most successful people in the business I desperately wanted be known for, basically said, I really like you. I want to help you. Come on over and I’ll introduce you to some other people who can catapult your career

And I said no.

Well, technically, I didn’t say no.
I just never went.

Which may actually be worse.

The Lie I Told Myself

At the time, I had all sorts of reasons for not going.

I was busy. I already had plans. The timing wasn’t great. Whatever.

In the end, that reasoning was all a truckload of crap.
Because the harsh reality hurts too much.

I was scared.

I was scared I’d walk into Jimmy Iovine’s house, sit across from him, and in a few minutes he’d realize he’d made a huge mistake.

Maybe I didn’t remind him of his younger self after all. Maybe he’d find out I was a fraud. An idiot.

What’s an even harder peach pit for me to swallow is my belief that accepting his help meant admitting that I needed help.

And I thought needing help meant I wasn’t good enough to do it myself.

So instead I did what I became exceptionally good at doing whenever I was scared.

Nothing.

I let the opportunity disappear.
And I never got to speak with Jimmy Iovine again.

I Did This For 15 Years

I hope you’re angry at me about that Jimmy Iovine story. You should be. I’m angry with myself.

And the worst part is that it wasn’t an isolated incident.

I spent the first 15 years of my career believing I was supposed to be an expert at everything, without anybody else’s help.

If I didn’t know something, I’d figure it out myself.
If I was struggling, I’d work harder.
If I was stuck, I’d keep digging until I somehow, hopefully, got myself unstuck.

Asking for help felt like revealing to the world that I wasn’t smart enough. Which, in retrospect, is fucking absurd.

Nobody is an expert at everything. Nobody builds anything meaningful by themselves.

I know that now.
I didn’t believe it then.

Or maybe I did.
I just didn’t believe it applied to me.

Then I Got To Be On The Other Side

Last week I sat on a panel for students at Hamilton College, my alma mater. I was honored to be asked, and shared the panel with a couple of really impressive people.

We talked about careers, opportunities and taking risks. All the stuff you’d expect a panel of execs to talk about to current college students.

But the three of us kept coming back to essentially the same message:

Ask for help.

We kept telling the students to put themselves out there.
Talk to people. Tell them what you’re trying to do. Ask for advice.

Because here’s the thing I didn’t understand when I was younger:

People actually want to help you.

Seriously.

I’ve said some version of that hundreds of times now. I just haven’t found the time machine that would allow me to say it to my younger self, and Lord knows, nobody else convinced me of it back then either.

And I Got A Message

The day after the panel, one of the students sent me a LinkedIn connection request.

He told me that it is difficult for him to put himself out there, but he’d heard what I’d said, so he wanted to push himself and reach out.

I read his message a few times. Because he sounded like somebody I used to know.

Me.
I was that kid.

I was the same one standing at the same door, wondering whether I should knock. And if I did, wondering whether I had the guts to stand there and talk to the person on the other side.

This time, I got to be the person on the other side.

Which Is Basically My Entire Job Now

There’s an irony to all of this that didn’t occur to me until I started writing this piece.

I spent the first part of my career refusing to ask people for help.
Now I’ve built an entire business completely focused on helping people.

I’m a coach. A mentor. My clients call me their leadership therapist.

High performing people call me when they feel stuck. When they’re struggling with something they can’t quite figure out. Or when they keep having the same problem with their team, and all the other attempts to fix it haven’t worked.

I help give them a new perspective on the problem.

I’m doing for people what I really wish somebody had done for me.

And I have to admit, I’m really good at it. Because I’ve been in your shoes. I’ve lived with your problems and I know the way out.

I can help you see the thing you can’t see because you’re standing too close to it. Which is exactly what I needed way back when.

Yeah, maybe I still would’ve made the same mistakes. Who knows.

But maybe, just maybe, I wouldn’t have spent 15 years of my life making some of those mistakes over and over again.

The Part I Still Haven’t Forgiven

I’ve had a great career. Don’t get me wrong. I’m grateful for all of it.

I’ve built three companies. Sold all three. I’ve worked with some amazing people, had some incredible experiences and somehow ended up with a life I’m pretty damn happy about.

That said, I still haven’t forgiven that younger me for not showing up to Jimmy Iovine’s house when the opportunity arose. I probably will never forgive myself. But I didn’t tell you that story because I want sympathy.

After all, maybe nothing would’ve happened.
Maybe Jimmy and I would’ve talked for 30 minutes, I’d have left and my life would’ve gone on exactly the same as it did.

Or maybe one conversation would’ve changed everything.

Unfortunately I’ll never know.
And that’s the shitty part of this whole thing.

It’s not just the opportunity I missed.
It’s the life I never got to find out about.

I don’t want you to make the same mistake.

Now It’s Your Turn

So let me ask you the question I wish somebody had asked me.

Where do you need help right now?

And are you actually asking somebody for help? Or are you doing what I did and trying to just figure it all out on your own?

Because asking for help doesn’t mean you’re incapable of doing it yourself. It doesn’t mean you’re an idiot.

Sometimes it just means you’re smart enough to realize that you don’t have all the answers.

And you don’t. Nobody does.
So do me a favor - when someone opens the door for you…

Walk in and start talking.

Speaking of which - I’ve got something new that I know you’ll love.

It’s called The Best Leadership Problem Lab. You show up with a real problem and a group of experts helps you solve it.

That’s the whole thing. You walk in with problems and walk out with solutions.

There are curated groups for founders, VPs, coaches, and working mothers. Sessions cap at 10-12 people.

If you’ve been trying to figure something out on your own for too long, this is your door. It’s time to walk in.

I talk to both Siri and Wispr Flow pretty much every day.

Siri hears the words I say. And that’s about all she does.

If I say something wrong, Siri transcribes it wrong. If I correct myself halfway through a sentence, Siri types the mistake, the correction and all the gobbledygook in between.

Every time I dictate something to Siri, I have to go back, reread it and fix half of what she wrote.

Sure, I could tell Siri to “try again.” But let’s not kid ourselves. We both know it’s only going to end with more work for me. At some point it’s just easier to do the damn thing myself.

Siri is basically the most annoying employee I’ve ever had.
Wispr Flow is different.

What Wispr Flow Actually Does

The first few times I used Wispr, it made mistakes too.

But I kept talking to it and a funny thing happened.
It started figuring me out.

It learned how I talk. It remembered the terms I use. It even learned how to correct my mistakes.

If I say, “Let’s meet Tuesday, actually wait, I mean Wednesday,” Wispr writes:

“Let’s meet Wednesday”

I don’t even have to tell it to delete Tuesday or explain what I meant.
It just knows.

And when it can’t quite figure what I’m saying, it usually understands my intention well enough to fill in the blanks.

I trust Wispr so much that I barely reread what it transcribes anymore.

Think about that. I’m trusting software to decide what I meant instead of what I said. And it does a great job.

Siri transcribes the words that come out of my mouth.
But Wispr understands who I am and what I mean.

That’s not just a technology difference.
That’s an employee difference.

And you’ve got both kinds working for you right now.

The Two Kinds Of People

Most employees operate like Siri.

You give them instructions and they translate your literal words into a literal task. It’s literally annoying.

Sometimes it works perfectly. But a lot of times it doesn’t. They either do the wrong thing, or they do the right thing wrong.

Either way, you end up reviewing what they did, correcting it and explaining what you wanted.

Again.
And again.

That’s the relationship with Siri employees.
You talk.
They transcribe.
You fix what they did wrong.

Siri employees aren’t the ones who get promoted first. They’re the ones people stop trusting with complicated work.

The best employees are more like Wispr Flow.

They don’t just listen to what you say. They learn you.

They figure out how you think and what matters to you. They pay attention to how you make decisions and what you mean when you say something that probably made a heckuva lot of sense inside your head but not so much when it came out of your mouth.

And most of the time, they get it right.

The Real Reason They Get Promoted

Every time you give an instruction to a Siri employee, you’re doing twice the work.

First you explain what you want. Then you check it, correct it or redo it.
And it never really gets better.

You could work with a Siri employee for three years and still have to explain things in gruesome detail because they never figured out how to understand the parts you didn’t say.

A Wispr employee is different.

Every correction you make is understood. Every mistake teaches them something. Every conversation you have gives them more context into who you are.

You don’t promote someone because they follow instructions well.
You promote them because they make your life easier.

That’s the difference.

The Flip Side

Of course there’s another side to this (isn’t there always?).

You’re somebody’s employee too.

Maybe it’s your boss. Your board. Or your biggest client.
I guarantee that there’s somebody giving you instructions.

And I guarantee those instructions aren’t always great.
Sometimes they’re incomplete. Some of them are confusing. Some are even said in a half-hearted hurry because they assume you’ll fill in the missing parts.

So what do you do?

Do you do exactly what they said and act surprised when what you did isn’t what they wanted? Or do you try to understand what they actually mean?

Because if you need everything spelled out perfectly before you can do great work, you’re not being careful.

You’re being Siri.

The difference between good and great isn’t how well you listen.
It’s how much you learn about the person you’re listening to.

P.S. I dictated most of this article using Wispr. It fixed my mistakes and somehow figured out what I meant. I didn't reread a single sentence until I pasted it here. That's kinda the point.

Picture, if you will, a zebra on the Serengeti.

In fact, let’s not say it’s a zebra. I’d rather use the British way. So instead of zebra, I’m gonna say zebra. Because I feel like the zebra pronunciation is somehow, for some reason, more appropriate for what we’re about to dis…

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It wasn’t because I couldn’t find one. It was because I was too scared to ask.

I thought asking for help would be proof that I didn’t know what I was doing.

Which, to be fair, I didn’t.
I just didn’t want anybody elseto know that.

It took me a lot of years and a lot of mistakes to understand the importance of a good mentor. They don’t just give you answers. They ask the hard questions you’ve been avoiding, and they see the patterns you can’t see because you’re standing too close to them.

And every once in awhile they’ll tell you the truth that everyone else is being way too polite to mention.

One of my leadership coaching clients said it perfectly last week:

“I don’t need more advice. I need someone to call me on my shit.”

Exactly.
That’s a good mentor.

The problem is that good mentors are hard to find.

They’re busy. They may not have time for you. And even if you find the right person, you’re not going to call them at 11:37pm because you’re having an existential crisis about a meeting tomorrow morning and really need to talk to someone.

So I started wondering:

What if you could build the exact mentor you need?

Not some generic AI both that tells you to believe in yourself and then gives you seven bullet points you don’t really care about.

I’m talking about an actual mentor.

Someone with the background you need. The personality that works with you. Someone who knows when to encourage you and when to call you on your shit.

So I created a prompt that does exactly that.

It asks you a few simple questions and then builds a mentor specifically for you.

And then you talk to them. Whenever you want.

No calendly link to schedule three weeks out. No awkwardness when you ask an awkward question. And no worrying that you’re wasting their time.

You’re not.

So you’ve got a pretty simple choice.
You can keep trying to figure everything out on your own.
Or you can put someone in your corner.

Both are options.
One is lonely.
The other is faster.

Meet your mentor. 👇🏽

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The world’s largest human resources organization just lost an $11.5 million lawsuit over its own human resource.

Go fucking figure.

SHRM, pronounced “SHERM”, is the Society for Human Resources Management. With ~340,000 members, it’s the largest association for HR professionals in the world.

SHRM positions itself as the central authority on HR best practices. They certify HR professionals and teach companies how to manage employees. They create standards that everyone else is supposed to follow.

Which is downright absurd when you consider my next sentence.

In December 2025, a federal jury found SHRM liable for racial discrimination and retaliation against a former employee.

Wait whaaaat?!

SHRM asked the judge to overturn or reduce the verdict. The judge declined.

SHRM asserts that the claim has no merit, but that’s not the reason we’re talking about this right now.

The reason I brought up the SHRM case is because of what allegedly happened before the lawsuit.

Because that part may have something to do with you.

When Being Different Makes You More Visible

Rehab Mohamed joined SHRM in 2016.

She is a woman of Egyptian decent. Her skin color, background and, heck, even her name made her different from many of the people around her.

According to Rehab, her supervisor began treating her differently from her white colleagues. She was cut out of meetings she had previously attended. Her work was more closely watched and got stricter scrutiny. And whenever she got close to meeting the standards for good performance, the standards would suddenly change.

When she complained, she says the treatment got worse. There was more isolation and stricter scrutiny.

So she escalated her concerns to the HR company’s HR department. She had five meetings with the VP.

Five.

But still, nothing got resolved.

So she went over everyone’s head and went directly to SHRM’s CEO, Johnny C. Taylor Jr.

Three months later, she submitted a formal retaliation complaint.

She was fired that same day.

Whoa, right?

The Pattern, Not The People

I’m sure SHRM has a different side of the story. The thing is, at least as it relates to our discussion, it doesn’t matter.

Let’s forget SHRM for a minute. In fact, forget Rehab too. Let’s just consider the situation.

Have you ever been part of a team where one employee looks, sounds, or appears differently than their manager and most of the people around them?

That employee is more noticeable.

And being more noticeable means being more closely watched.

That is called tokenism.

Research on tokenism has found that people who are underrepresented within a group can become hyper visible. Their behavior attracts more attention, their differences are more exaggerated and their performance can get greater scrutiny.

It’s not uncommon for the supervisor to start micromanaging that one person a little more than everyone else.

That doesn’t mean the manager is consciously racist, sexist, ageist or any other -ist. Heck, that manager may not even be doing any of it consciously. They just naturally pay a little more attention to the one person who is different.

And that little difference in attention can turn into a big difference in evidence.

Let me explain.

Everyone Makes Small Mistakes

Everyone makes mistakes. We’re human, after all.

Maybe someone sent a presentation with a typo. Or someone else was ten minutes late to an important call. And who among us hasn’t forgotten to copy the right person on an email.

You’ve done it. I’ve done it. We all have.

Most of those mistakes aren’t performance problems. They’re proof that humans are involved.

When you pay attention to everyone equally, you’ll notice some of everyone’s mistakes. Most are corrected and quickly forgotten. They don’t matter in the long scope of things.

But what about the person you watch twice as closely?

You’ll notice more of their mistakes.

Not necessarily because they make more mistakes, but because you’re paying closer attention for when they come around.

Since you notice more mistakes, you start to get concerned.
So you pay even closer attention to them.

Maybe you start following up more often. Or you ask for more explanations. Maybe you start making notes about their mistakes, even though the same mistakes would’ve been forgotten if somebody else did them.

Somewhere in here, confirmation bias joins the party. Because once you suspect that someone isn’t meeting your expectations, your brain is really good at finding the evidence to prove you’re right.

Six months later, that one person has a file filled with missed details, questionable decisions and minor incidents. Everyone else has a clean record.

From the outside, their failure to perform looks objective. After all, look at all the documentation.

But in reality, it may not prove one person performed worse than others. It’s only proof that one person was watched more closely than everyone else.

This is a real thing.

It’s called Prove-It-Again Bias.

Prove-It-Again Bias

Prove-It-Again Bias was coined by Joan C. Williams, a professor at UC Law, San Francisco.

Williams’ research found that women and people of color are often required to provide more evidence of their competence than their colleagues. Other employees are more likely to receive the benefit of the doubt, or to be judged on their potential rather than their actions.⁠

Some people are assumed to be capable until proven otherwise. Others are required to prove they are capable.

Then prove it again.

And again.

The same idea applies to mistakes.

When someone “looks the part,” a mistake is often assumed to be a fluke.
When someone looks different, the same mistake can be treated as evidence to a larger pattern.

And one success is never enough to change the manager’s opinion, because the whole thing becomes a self-fulfilling prophecy.

That’s how unequal scrutiny can eventually create what looks like an objective performance problem.

The evidence is fair.
The way it was collected isn’t.

The Part That’s Actually About You

You’re probably reading this thinking that you don’t do that. You’ve never watched someone more closely because of their race, gender, accent, age, background, personality, or anything else.

I doubt it, but let’s assume that’s right.
So here’s my question.

Think about everyone on your team. If you aren’t part of a team now, think of a previous one.

Can you name, off the top of your head, the last small mistake each person made? Not the catastrophic ones. I’m talking about the small, forgettable ones. The typos. Missed deadlines. Showing up late. That type of thing.

If you can quickly name multiple mistakes from one person and nothing about anyone else, you may want to take a breath and think about why.

Maybe that person is actually struggling. Or maybe you’ve just been watching them differently.

I’m not saying you’re a bad person. I’ve seen no evidence to make me think otherwise. Well, aside from those photos. But you said it was just a phase in college.

This whole thing isn’t about intent. It’s about where your attention goes when you’re not paying attention to your attention.

Because whoever you pay more attention to will usually have a longer list of mistakes. Not always because they’re worse at the job.

Sometimes it’s because of you.

Nobody Outside That Room Knows

Only a handful of people really know what happened with Rehab at SHRM.

A jury found in her favor. SHRM’s response was succinct: “This claim has no merit. None.”

Maybe SHRM will eventually win an appeal. But that’s not my point.

My point is that somewhere in your work life right now, evidence might be getting built against one person while everyone else’s files stay conveniently empty.

But documentation is only objective if the observation behind it was done fairly.

So the question isn’t simply whether you’re biased.
It’s whether you’re watching everyone the same way.

P.S. SHRM certifies HR professionals and sets the HR standards companies follow. Their own HR department had five meetings about this situation and resolved nothing. If that doesn't make you think about your own HR processes, I'm not sure what will.

The patterns shaping how you distribute your attention — and who ends up with the most documentation — are exactly what the free Leadership Diagnostic Workshop uncovers. Learn more here.

We spend an awful lot of time and energy trying to get rid of it. We all do. There are books about overcoming fear. Therapists who help us manage our fear. Coaches who tell us to push through fear.

And I get it. Some fear really sucks. Like if you’re so scared that you can’t make a decision, you can’t take a risk, you can’t even get yourself to move — that’s a big problem and you need to get that taken care of.

The Fear I Don’t Want to Lose

But there’s another kind of fear that I’m a lot more worried about losing. And I honestly think you should be too.

It’s that little voice inside your head that says: “Oh shit, what if I screw this up?”

I know that voice. I know it really well. All too well.

Every company I’ve ever started, I was scared. Every time I’ve made a big career decision, I was scared. In fact, every time I take on something where I’m not completely sure I know what the hell I’m doing, I’m scared. It still happens.

There’s probably a little fear in me right now that I’m going to screw up talking to you here.

And the reason I’m having this entire conversation is because I used to think fear was the problem. I thought that someday I’d be experienced enough, successful enough, whatever enough, that the fear would finally go away.

But I don’t think that anymore.

In fact, now I think that the moment fear goes away is the moment when you should start worrying.

Let me explain.

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You’re not going to change.

You think you are.
You think it’s all going to suddenly turn around.

You’re lying. And choosing to believe your own lie.

I’ve seen it happen a thousand times before.
You say you’re not happy in your job.
You’re not happy in your relationship.
You’re not happy with your weight or your fitness or your finances.

You’re not happy with something.

You promise to do things differently.
You’ve already had the conversation a hundred times.
In the shower.
In the car.
Lying awake in the middle of the night when your mind just won’t stop moving.

You tell yourself you’re finally going to say it.
You’re going to climb out of the hole. And you’re going to do it this year.
Maybe even this month.

But here we are and you haven’t done a damn thing about it.

You want your life to be better. But as far as I can tell, your only strategy to achieve that is hope.

Hope isn’t a strategy.
It’s an excuse.

I know this, because I used to do it too.
And trust me, hope isn’t going to get you a new job, a new partner, or a different life.

Hope is like the last life preserver on the Titanic. You can hold on to it as tightly as you want, but the ship is still going down. And you’re going down with it.

If all you have is hope, you’re not ready to change.
Life doesn’t suck enough for you to change.
Not yet.

Change only happens when the pain of changing is less than the pain of staying the same.

If you were really done with your situation, you’d already be doing something about it.

You’d have sent the resume. Had the conversation. You’d have made the call you’ve been rehearsing for six fucking months.
But you haven’t.

So either shut the hell up about it, or do something.
Do anything.

Because from where I’m standing, you’ve already decided that staying stuck is easier than changing. You’ve decided that guaranteed unhappiness is better than a chance of being happy.

And that’s absurd.

But you keep justifying it.
You say “it’s not that bad.”
You claim you’re just “being patient.”
You compare yourself to people who have more pain just so you have an excuse to deny yours.

You said this was the last time.
You said that last time too.

Now none of it feels like a crisis to you. Because if it were a crisis, the decision would happen on its own.

A job in crisis gets you fired.
A relationship in crisis ends itself.
Your health in crisis forces the diet.

You’ve been waiting for something to get bad enough to do the deciding for you, so you never have to be the one who chooses.

That’s not patience.
That’s avoidance.

Here’s the thing you need to understand: when your problem turns into a crisis, you’ll always end up with fewer choices than you have now.

All you’re doing is trading the version where you’re in control for the one where you have none.

The job you leave on your own terms is not the job you get fired from.
The relationship you end with your eyes wide open is not the one that suddenly abandons you.

Every year you wait for the pain to get big enough to force your hand. But you don’t need a bigger crisis. You need to stop lying to yourself about the one you’re already in.

So stop saying it’s fine.
It’s not.

I’m not telling you that it’s going to be easy. I’m not even telling you to make rash decisions.

I’m only telling you that you have choices right now and if you continue to wait, eventually your choices will disappear.

So do me a favor and, for just one honest minute, think of all the ways your life is being held back. The emotional cost. The professional cost. Even the financial cost.

Now compare that to the thing you’re afraid of. The hard conversation. The resignation letter. The truth you have to finally admit to yourself.

Which is worse?

You see, you’ve been focusing on the fear of making a change. Stop that.
It’s time to focus on the regret of not changing.

Change is never about becoming braver or more disciplined. It’s about seeing your life clearly enough that the status quo is no longer the safe choice.

You already know what you have to do.
You’ve just been very good at not looking.

Look.

In fact, according to a study that Forbes did, between 48% and 64% of new employees consider leaving a new job, or at least are less likely to stay at the job, after experiencing a bad onboarding process.

More than half the people consider leaving a job after a bad onboarding experience. It’s crazy.

The Six Months You Just Wasted

So you’ll spend 6 months trying to hire somebody.

You interview them 4 times, maybe 5 or 6. Check the references, negotiate the salary, and convince the person to leave a company they already know. People they already know. And a boss they may actually like. In order to take a chance on you.

Sometimes they’re even turning down another offer to do it. It’s not like it’s a small decision.

And then they show up for their first day at work and you’re like: “Welcome. Here’s your laptop and temporary password. That’s your desk. Get comfortable. The benefits orientation is at 10.”

What the hell are you doing?

You just spent months selling this person on the idea that joining your company could change their career. And your first act is to teach them how to fill out an expense report and submit for vacation time.

Come on now.

The Jane Story

I was talking with a client recently about a hire she made that she was really excited about. Let’s call the client Jane, like in The Jetsons.

This was a great hire. This was somebody Jane really wanted. It was the kind of person where the whole leadership team was excited. They thought: if we can get her on our team, that’s going to change everything.

They got her.

And her first week was filled with HR paperwork, laptop setup, benefits, org chart, a meeting about meetings. Somebody gave her a tour of Slack, which I’m sure was thrilling.

By Thursday, she pulled a colleague aside and asked if it was normally like that there.

That’s not a question you want your brand new employee asking in their first week at work.

Not surprisingly, 6 months later she was gone. Refer to the Forbes study I mentioned earlier.

It wasn’t because this woman couldn’t do the job. She could.

It was because in her first week there, she had already started wondering whether taking the job was a mistake.

The Question Nobody Answers

Most companies think onboarding is about getting someone set up. It’s not.

Getting someone set up is logistics.

Onboarding is something completely different.

Every new employee, from the second they walk through the door on their first day, is asking one question. And most companies are too busy explaining the health benefits to even consider the question, let alone answer it.

Here’s the question every new employee asks.

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Ideas I was truly excited about.
Ideas I was absolutely convinced were going to work.
In retrospect, they were ideas that probably would have been a huge success if somebody else had been in charge of them.

Unfortunately, I was.

Because when it comes to your next big goal or project, there are a thousand things that can screw it up. Bad timing. Bad assumptions. Other people. The economy. Money. Your horoscope on the day of the big meeting.

It could be anything.

But there’s one potential problem that you probably aren’t spending nearly enough time thinking about.

You.

You bring the same person, the same thinking and the same identity to every new project.

Your need for control. The way you get bored halfway through. Or how you expand one simple concept down so many different roads you’re not sure how to even get started.

Whatever your thing is, it comes with you. Always.
It’s like those leech-like sucker fish that attach to sharks. Wherever you swim, the sucker is still with you.

This is why I love the idea of a pre-mortem.

A post-mortem happens after something dies. You look back at the body and try to figure out what killed it.

A pre-mortem is much more helpful for people like you and me.

The basic idea is that you assume the thing you’re about to do has already failed. An embarrassingly spectacular failure.

Then you work backward and figure out what is going to kill it while you still have time to avoid the problem.

That’s what this week’s AI prompt does.

But wait… there’s more. Because isn’t there always?

The prompt doesn’t just ask AI to figure out what could kill your project. It asks AI to figure out how YOU are probably going to kill it.

And then it will tell you what to do before you even get the chance to screw up yet another great idea.

So don’t take one more step towards your project or goal, run this prompt first. Before you start. Otherwise, you’re just going to regret it and come back to me to tell me how you should’ve listened.

Don’t say I didn’t warn you.👇🏽

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