Earn better.

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This is for anyone who feels the gap between where they are and where they want to be.

This was the year I lost my ambition. Or so I thought.

When I started Ladies Get Paid, I dreamed of building an empire. Millions of people, millions of dollars. But then too many hiccups happened: misplaced bets, bad luck, bad timing, and I went from big dreams to just wanting to provide for my family.​

Now I’m the primary parent for our 21-month old twins, having lost breadwinning privileges to my wife who out earns me (though not enough to put our kids in daycare. You might relate.)
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I started asking myself a lot of hard questions: Should I be more realistic with my dreams? Did they require more talent than I have?

Fortunately, I’m a good coach and sometimes remember to coach myself. I noticed that I’d fallen into the common trap of seeing things in a binary lens:

I’m either ambitious or I’m not.

Ambition is only allowed when you’ve proved you can achieve it.

Limited time means limited dreams.

Turns out, I was looking at it all wrong. Limited time shouldn’t limit ambition. It’s a lens for focus. And focus starts with clarity.

To see things clearly, I needed to ask more open-ended questions, like what lifestyle do I actually want? What legacy do I want to leave? And underneath those answers—why does this matter to me?
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Different questions begat new awakenings. I realized – with more certainty that before – that I am even more committed.

However, my resources are limited. I simply don’t have the luxury of high-intensity output like I used to. But that’s okay. In fact, that’s even better. Because less time requires more commitment. Commitment to focus.

Also, I’ve learned that retreating is not failure or surrender. You need seasons of coasting just as much as you need seasons of building. One foot in front of the other. Slow and steady.

Here’s why I believe in big dreams: they can be a lifeline out of whatever situation you’re in. It’s about learning to be okay with not having fulfilled it. It’s about learning to fall in love with – again and again – the pursuit. Because that’s where most of life exists anyway. In the trying.

That’s why the AOC story always makes me cry. Yes, that AOC.

It was at Ladies Get Paid event on a random Thursday night years ago. When I asked the audience what they were reinventing (the theme of the evening), she declared she wanted to run for office and I burst into tears. Why? There was absolutely zero proof she could do it. It was her public declaration of unmitigated ambition that was stunningly powerful. She didn’t need to win to inspire us.

The dreaming matters. The pursuit matters. You matter.

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Your Turn

1. What ambition have you been shrinking because it feels unrealistic? Write it down without editing.
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2. What lifestyle and legacy do you actually want? Ask yourself “why does this matter?” three times to get past the easy answer.
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3. Complete this sentence: “I would pursue this even if I never achieved [specific outcome] because…”
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4. Does that sentence feel true? If yes, what’s one action you can take this week that honors both your ambition and your current constraints? If no, can you give yourself permission to let it go for now?
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5. Are you in a season of building or coasting? What does your body tell you about what you need right now?
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Now go get paid.

x Claire

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PS Loved this email? Share it with someone who could benefit 🤗

Resources ​

Looking for a job? ​LLC of Me​ Dreaming of a new career? ​Pivot Pathfinder​ Preparing to negotiate? ​Earn Better​ Seeking guidance? ​Explore Coaching​

I work with high-achieving women who are successful on paper but struggling beneath the surface…and I’d love to work with you 🤗

You might be:

• The Golden Handcuffs Client: Well-compensated but soul-starved. You want meaningful work but can’t afford to sacrifice financial security—especially with a family depending on you. The thought of starting over feels paralyzing.
• The Ambitious Achiever Who Hit a Wall: You do everything “right”—stellar performance, great relationships, impressive results—but you’re not advancing as expected. You get to final rounds but don’t close the deal, and you can’t figure out why.
• The Brave Leaper in Analysis Paralysis: You’re already mid-transition but frozen by overthinking. You have courage but lack clarity, strategy, or confidence. Every option feels like it could be the “wrong” choice.
• The Expert Stuck in Your Expertise: You have deep knowledge and experience but struggle to translate it into something marketable. You’re caught between your established identity and who you’re becoming.

If any of these resonate, you’re not broken. You’re at a critical inflection point that requires both strategic clarity AND the internal tools to execute with confidence.

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Why Choose Me

Most coaches give you either strategy OR mindset work. I seamlessly weave together:

1. Practical next steps with the internal alignment work needed to execute them
2. Strategic roadmapping with tools to manage your present so you have bandwidth for your future
3. Market positioning with the confidence to own your worth and negotiate from strength

I don’t push you to quit your job tomorrow or take dramatic leaps. Instead, I help you see your current paycheck as “a venture capitalist funding your transition” so you can shift to a more empowered position.
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I provide gentle support when you’re struggling with fear and self-doubt—and firm accountability when you’re making excuses or avoiding necessary action. I won’t let you stay stuck in planning mode or let perfectionism sabotage your progress.

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The Real Reason My Coaching Works

Here’s what I’ve learned after working with thousands of women: When you say you want a “career change,” what you really need is alignment between who you’ve become and how you show up professionally.

The surface problem is job dissatisfaction. The real problem is identity evolution.

I’ve lived through the messy, complicated reality of major life transitions. I know what it feels like to be successful on paper but lost inside. I understand the fear of making the “wrong” choice when everything feels high-stakes.

My approach is to turn my life inside out—taking what I’ve learned (mostly through struggle) and breaking it down in a way that’s accessible and actionable for you.

Start with a 30 Minute Session

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​Listen instead​

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Years of solid experience, a clear skill set, and still… you have no idea what you actually want to do next?

You watch your friends hit traditional milestones—promotions, career pivots that seem to “make sense”—while you’re stuck in analysis paralysis. You know you’re ready for something different, but every path forward feels either too risky or too boring.

Here’s the frustrating part: You’re capable. You’re qualified. But somewhere between “I’m ready for a change” and “I know exactly what I want,” you’ve become frozen.

My client Ali had this exact problem. She was a skilled content writer, six years of experience, but completely unclear on what her “something new” should be. The job market felt impossible, and the uncertainty was eating away at her confidence.

But here’s what we uncovered—and why it matters if you’re tired of feeling stuck:
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​In this week’s Substack, I break down:

• Why the thing you do “for fun” might be your actual superpower—and how to leverage it
• The exact reframe that opens up opportunities you couldn’t see before (hint: it’s not about job titles)
• A 7-day plan that moves you from paralysis to experimentation, so you can finally take action instead of spinning your wheels

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Read the full post

Hi, I’m Claire Wasserman and I help you expand your worth, wealth, and wellbeing.​ ​ I’d love to support you – learn more here.​ ​