Earn better.

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This is for anyone who feels like they can’t show up as their full, messy self.

My wife was not thrilled that I shared our debt number to the entire internet a few months ago. Some family members also raised their eyebrows at my “oversharing”…and they’re not wrong.
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But I’m conflicted.

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On one hand, I understand their desire to keep “things private.” On the other hand, the topics I cover (money, negative self-talk, being a woman in the workforce, heck, being a woman), are so often mired in shame. And the antidote to shame – I believe, and Brené Brown would concur – is to take it out of the shadows.
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I just happen to do that in front of hundreds of thousands of people.
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In full transparency though, it’s doesn’t quite “feel real” when I write these newsletters since I’m usually in my pajamas in the dark. It’s only when I meet one of you in person that that it actually dawns on me how much you know about me.
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So why do I keep sharing and why does that matter for you?
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In my opinion, it’s about emotional honesty. Something I’ve struggled with for years (heck, I didn’t come out till I was 30 and married to a man!), which I know I’m not alone in.

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It’s a dangerous path to disassociation that tells your inner self that you can’t handle difficult emotions. That you’re too much.
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And so certain feelings and behaviors become unacceptable, like being messy or making “wrong” choices. Or oversharing.

I’ve found that experimentation is the only way through this. Trying things again. Trying things differently. I’m in the midst of writing a memoir about my son’s medical crisis; I’ve gone through so many drafts as each one strips away another layer of performance to get to the “real stuff”—which, as I define it, means emotional honesty, truth, dull transparency, the whole damn human experience.

Which usually means complexity. And often, in that complexity, I don’t look “good.” I’m complicated and messy, and while yes, I’m the protagonist of my own story, I don’t always make choices my ideal self or higher being would be proud of.

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It just doesn’t stay in my diary. Instead, it goes in a newsletter to 50,000 people. A post on social to 168,000.
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Then I refresh my inbox compulsively to see if anyone’s emailed me back, driven by that very human desire to be recognized.
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Because that’s the ultimate reason I do any of this work: to make you feel seen. But also, me. Responses like this help:

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Of course, it’s not so straightforward.
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What happens after you’ve been “exposed”? Whether it’s a family member’s discomfort, or someone recognizing me IRL —sitting with being seen comes with its own complex emotions.
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In short: I’m still grappling with it. I know transparency in the name of truth, in service of being seen, is my North Star.
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But how to navigate it? I’m figuring it out as I go.

Your Turn

I want to invite you to sit with these questions—not to answer them perfectly, but to explore them with the same messy honesty I’m trying to practice:
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1. Where are you performing instead of being present? Think about a recent conversation, email, or social media post. Were you crafting an image of yourself, or were you showing up as you actually are—complicated, uncertain, in-process?
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2. What are you not admitting to yourself? Is there something you’ve been skirting around? A feeling you’ve labeled as “shouldn’t feel this way”? A truth that feels too inconvenient or uncomfortable to face?
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3. When do you jump to the silver lining? Notice the next time you rush past something painful or difficult. What are you trying to avoid feeling? What would happen if you sat with it for just a few minutes longer?
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4. What’s the cost of not being seen? Think about a part of yourself you keep hidden—from others, from yourself. What does it cost you to keep it tucked away? What might shift if you brought it into the light?
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5. Who in your life knows the real you? Not the performed version, not the “ideal self”—the actual, messy, contradictory you. If your answer is “no one” or “not many,” what’s one small step you could take toward letting someone in?

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Take what resonates. Leave what doesn’t. And if you want to share what comes up, hit reply. As you know, I read every single one 😉

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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.
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• 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.
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• 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.
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• 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.
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Start with a 30 Minute Session

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You know you need to change something. You can feel the patterns—the internal conflict, the exhaustion, the loop that keeps you stuck. But knowing isn’t the same as transforming.

You’ve done the therapy. Read the books. Had the breakthroughs. And still, the same parts show up: the one that pushes you to work harder, the one that shames you for resting, the one that keeps you feeling perpetually behind.

Here’s what’s actually happening: Your parts aren’t the problem. They’re trying to protect you. But they’ve forgotten how to work together.

When I spent a week self-coaching through my own stuck moments, I didn’t just get clarity—I got humbled. The patterns were so clear, so repetitive, that I couldn’t believe I hadn’t seen them before.
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​In this week’s Substack, I break down:

• The 6 patterns that showed up in every single coaching session with myself (and why you probably have versions of them too)
• Why “should” is your alarm system—and what to ask instead
• The exact moment shame rushes in to distract you from the real wound (and how to catch it)
• A 7-day self-coaching plan to identify your patterns, integrate your parts, and finally break the loop
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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.​ ​