Stop Playing Small!

Issue #024 | June 20th, 2025

In partnership with

Will Here….. Welcome Back!

Ever Feel Like You're Running on Empty... Even After Your Third Cup of Coffee?

Look, I get it.

You're sitting there, staring at your screen, waiting for some magical burst of productivity to hit...

But instead? 

You find yourself clicking through seventeen different productivity apps, opening twenty-three browser tabs, and somehow convincing yourself that reorganizing your desktop icons counts as "getting stuff done."

Sound familiar?

Here's the thing nobody wants to tell you (but I will):

All those hours you're grinding away? They're not making you more successful...

They're actually KILLING your success.

I know, I know. That stings a little, right?

But stick with me here because what I'm about to share could completely transform how you work...

See, the smartest solopreneurs and most successful leaders I know have figured out something that most people never will:

It's not about working MORE hours...It's about finding your ONE BIG DOMINO.

That one thing that, when you knock it down, makes everything else either easier or completely unnecessary.

And once you find it? Everything changes.

You stop playing small. You start winning big.

You work less but accomplish more. You have more energy at the end of the day instead of feeling completely drained.

Ready to discover what that could look like for YOU?

Inside this issue: Your Escape Plan From Productivity Prison:

  • The Success Saboteur: Why Kailen's "more hours" strategy was costing her money (and her 30-day fix).

  • Messy Mind Fix: Turn your chaotic to-do list into a laser-focused action plan with this AI trick.

  • Browser Tab Detox: Why 52 open tabs are draining your brain... and the 5-minute fix for instant clarity.

  • Stop Email Novels: The 2-minute tool that explains anything faster (your clients will thank you).

  • StartSmart Challenge: Prove working smarter beats working harder. Share your wins.

➡️ Reality Check – More Hours ≠ More Wins

Picture this: It's 2:47 AM.

Kailen's sitting at her kitchen table, laptop glowing in the dark, surrounded by empty coffee cups and crumpled sticky notes.

She's been grinding for 14 hours straight... AGAIN.

Marketing campaigns, client projects, bookkeeping - you name it, she was doing it all. Because that's what "successful entrepreneurs" do, right?

Wrong.

That night, exhausted and barely coherent, she almost hit "send" on a proposal that would have cost her biggest client $50,000.

Her finger was hovering over the button when she caught the mistake.

That's when it hit her like a freight train:

All those 70-hour weeks weren't making her successful...

They were setting her up for DISASTER.

Here's What Nobody Tells You About "Hustle Culture":

After 50 hours a week, your productivity doesn't just slow down - it CRASHES.

After 55 hours? You're literally working backwards and making more mistakes and burning out your creativity.

Basically, shooting yourself in the foot while calling it "dedication."

But Here's Where Kailen's Story Gets Interesting...

Instead of grinding harder (like most people do), she asked herself ONE simple question:

"Is this actually moving my business forward... or am I just staying busy?"

That question changed EVERYTHING.

She stopped doing busy work. Started focusing on the stuff that mattered.

The result?

Better business growth. Happier clients. And for the first time in years, she felt like she was winning instead of just surviving.

Sound like something you need?

Key Insights & Practical Steps:

  • Impact over hustle: Identify and focus on your 2-3 most crucial tasks daily.

  • Delegate or automate: Recognize tasks that don't require your personal touch and automate or outsource them to streamline your business operations.

  • Protect downtime: Resting is not optional—it's essential. High-quality rest boosts creativity, decision-making, and productivity.

StartSmart™ AI Power Prompt: (copy and paste this into your favorite AI tool, I prefer ChatGPT 4.5)

“You are an expert success architect with over ten years of experience guiding high-achievers through life-changing transformations. Before you begin, please provide:

  1. Your ultimate success vision: Describe the exact outcome you want (for example, “doubling my business revenue to $500,000 in 12 months”).

  2. Your top three fears: List the fears holding you back (for example, “public speaking,” “scaling too fast,” “financial instability”).

  3. Your current starting point: Outline where you are right now (for example, “$200,000 in annual sales, team of 3, limited marketing budget”).

Once I have those details, I will craft a clear, step-by-step blueprint that looks back at my future success. Detail:

  • The specific fears I overcame and how I reframed or conquered each one.

  • The strategic moves I executed at each stage, with suggested timelines.

  • The daily habits and routines I adopted to build sustained momentum.

If anything is unclear or you need further information to improve your response, please don't hesitate to ask me.”

✅ Pro Tip: The "Tab Shame" is Real (And It's Killing Your Focus)

Go ahead... I dare you.

Count those browser tabs right now.

17? 23? Oh wow... is that 52 tabs staring back at you?

Look, we've ALL been there. No judgment here.

But here's what's happening that you probably don't realize:

Every single one of those tabs is like having someone constantly tapping you on the shoulder, saying, "Hey! Remember me? What about me?"

Your brain is literally trying to keep track of all of them at once—no wonder you feel scattered and overwhelmed.

Here's Your 2-Minute Brain Detox:

Right now - and I mean RIGHT NOW - close any tab you haven't clicked on in the past week.

That cryptocurrency article from March? Gone.

The "17 Best Productivity Hacks" you bookmarked but never read? Bye-bye.

If you haven't clicked on it by now, let's be honest... you never will.

Why This Works So Well:

When you clear those tabs, something magical happens. Your brain literally sighs with relief.

Less mental clutter = more focus. Faster browser = less frustration. Cleaner workspace = clearer thinking.

Make this your new weekly ritual, and watch what happens to your productivity.

Trust me on this one. We are all guilty of Tab Mania!

The easiest way to stay business-savvy.

There’s a reason over 4 million professionals start their day with Morning Brew. It’s business news made simple—fast, engaging, and actually enjoyable to read.

From business and tech to finance and global affairs, Morning Brew covers the headlines shaping your work and your world. No jargon. No fluff. Just the need-to-know information, delivered with personality.

It takes less than 5 minutes to read, it’s completely free, and it might just become your favorite part of the morning. Sign up now and see why millions of professionals are hooked.

➡️ Tool Spotlight: Loom – Show, Don’t Tell

Stop Writing Email Novels (Your Clients Are Begging You)

Okay, be honest...

How many times have you started typing an email and somehow ended up writing the next Great American Novel?

You know what I'm talking about. 

You start with "Hey, quick question..." and three paragraphs later, you're still explaining the backstory to your backstory.

Meet Sam - The Reformed Email Novelist

Sam used to be the king of epic emails. We're talking War and Peace-level explanations for the simplest things.

His weekly routine?

Crafting these masterpieces that nobody reads all the way through, then jumping on "quick" calls to explain what he just wrote anyway.

Sound familiar?

Then Sam Discovered His Secret Weapon: Loom

Instead of typing out another dissertation, Sam started recording quick videos.

Just him, talking like a normal human being, showing exactly what he meant on his screen.

Here's When Sam Uses Loom Instead of Email:

Explaining feedback on designs or documents - Instead of "Move the blue button 3 pixels to the left and make the font slightly bolder but not too bold..." he just shows it.

Walking through processes - No more "First click here, then scroll down, then click the thing that looks like..." Just screen record it.

Giving project updates - Instead of bullet-pointed status reports, he records a 2-minute "here's where we're at" video.

Answering complex questions - When someone asks something that would take four paragraphs to explain, he talks it through.

The results were insane:

Got back 40% of his week, way fewer confused responses, and his team started UNDERSTANDING him the first time.

Want to Join the "Reformed Email Novelists Club"?

Step 1: Grab Loom (it's free and takes literally 2 minutes to set up)

Step 2: Next time you catch yourself writing paragraph #3 of an email, stop. Hit record instead.

Step 3: Just talk like you're sitting across from your colleague. Show your screen if needed.

Rule of thumb: If it's taking you more than 2 minutes to type, it's probably a Loom moment.

Your inbox (and your sanity) will thank you.

Modernize Out Of Home with AdQuick

AdQuick unlocks the benefits of Out Of Home (OOH) advertising in a way no one else has. Approaching the problem with eyes to performance, created for marketers and creatives with the engineering excellence you’ve come to expect for the internet.

You can learn more at www.AdQuick.com

➡️ StartSmart™ Challenge

Time to STOP Reading and START WINNING

Listen up, because this is where the magic happens.

You just absorbed some serious gold about browser detoxes, Loom videos, and working like a champion instead of a hamster on a wheel...

But here's the brutal truth: ALL of that knowledge is completely WORTHLESS if you don't take ACTION.

Your StartSmart Challenge This Week:

Stop making excuses. Stop overthinking. Stop "planning to plan."

Pick ONE strategy from today. Just ONE. And CRUSH IT.

Close those browser tabs that are sucking your brain dry.

Record that first Loom video and watch your communication game level up INSTANTLY.

Start asking yourself the question that separates winners from wannabes: "Is this moving my business forward, or am I just fooling myself?"

Whatever you choose - DO IT TODAY. Not tomorrow. Not next week. TODAY.

Then Here's Where You Become UNSTOPPABLE:

Don't just do it in silence. SHARE your victory!

Did you close 47 tabs and feel your brain come alive again? TELL US!

Did your first Loom video save you 3 hours of email ping-pong? WE WANT TO HEAR IT!

Had an epic fail that taught you something huge? EVEN BETTER!

The most inspiring stories get featured in next week's newsletter - this is your chance to motivate thousands of other entrepreneurs!

And speaking of next week...

I'm dropping THE question that separates the top 1% of entrepreneurs from everyone else.

This isn't some fluffy "what's your why" nonsense.

This is the ONE question that literally rewires how you attack every single day.

But first - TAKE ACTION. Right now. No excuses.

Your breakthrough is waiting on the other side of that action.

Make it happen!

➡️ That’s a Wrap!

Thanks for joining this productivity revolution. This newsletter is your first step toward smarter decisions, bigger wins, and a better work-life balance.

Hungry for more tips and strategies? Join our dynamic StartSmart™ Community, where we dive deeper into productivity hacks, business strategies, and life optimization weekly.

Know someone trapped in an endless hustle? Please forward this newsletter and help them break free, too!

Stay smart, and let's make big things happen together!

See you next week!

Remember: While everyone plays checkers, you play a masterful game of chess.

And that's what makes the difference.

This Week's Hot Question: "What will you change to play a bigger game that will propel you to the next level? If you have no ideas, ask your reliable AI assistant for help. "

🔥 Want More Magic: Join Our StartSmart™ Exchange Community Here!

Until then, Think Big, Play Smart, and Build Strong.

To your success,

-Coach Will

Please let me know if you have any comments or require assistance. I read everything; you never know what doors might open from a simple conversation.

😭 Drowning in newsletter chaos? Yeah, me too. Then I found Meco - now ALL my newsletters live in one gorgeous app (totally free). Finally hit inbox zero → Try it Here!

DID A FRIEND FORWARD YOU THIS NEWSLETTER?

First, give them a BIG thank you!

Then, subscribe here for your free weekly dose of StartSmart™ Life Hacks! Until next week, remember: In a world of complicated choices, be the obvious one.

Reply

or to participate.