I wasn't sure I was worthy of connection

Earn better.


This is for anyone who has ever wondered who they'd be without their job title.

I vomited on the bus.

Not the grand entrance I'd imagined for a wellness retreat designed to "heal, restore, and revive" me for the next season of my life. But there I was, winding through the Tennessee hills, coffee sloshing in my empty stomach, losing it completely before we'd even arrived.

If I'd known what was coming, I might have taken it as a warning. But looking back now, I wonder if it was something else entirely—a clearing out. An emptying to receive what I didn't yet know I needed.


The retreat had two main rules.

The first was easy: no phones. I handed mine over without hesitation, almost relieved to have permission to disconnect.

The second rule nearly broke me: no talking about what you do for work.

My immediate response was to argue. But it's so much of who I am, I wanted to say. How am I supposed to introduce myself? How will people know...

Know what, exactly?

Know that I matter? Know that I'm worth talking to? Know that I deserve to be here?

That's when I realized: my work wasn't just part of my identity. It was a shield. A carefully constructed barricade I'd been building for years, achievement by achievement, accolade by accolade, hiding something I didn't want to look at.

The belief that I must earn my worthiness.

At dinner that first evening, I found myself telling my tablemates all about what my brothers do for work. Since I couldn't talk about me, I'd apparently decided to lead with their resumes instead. Even in the retelling, I could hear myself doing it—reaching for accomplishment, any accomplishment, as a way to establish... what? Connection? Credibility?

A reason to be worth their time?

Here's what made it worse: this was a specially curated group of people, each influential in their respective communities. I was honored to be included. I was also completely intimidated.

Walking into the dining hall felt like being transported back to high school—scanning for where to sit, who looked safe, who might let me join them. Except this time, I didn't have my usual crutches. No elevator pitch. No impressive title to drop. No recent win to casually mention.

I watched the other participants move through the space with ease, walking up to complete strangers and falling into conversation like it was the most natural thing in the world. Meanwhile, I stood frozen, genuinely unsure of what to say or, honestly, who to be.


Because it was a wellness retreat, I tried a different opening line: "How are you feeling?"

And because it was a wellness retreat, it worked. People answered honestly. Conversations went deep fast—much deeper than "What do you do?" ever goes.

But I noticed something. Even when the conversation flowed, even when I felt genuinely interested in the person across from me, there was a hum of anxiety underneath. A voice asking: Do they find me interesting? Am I giving them enough? Do they know I'm someone worth knowing?

Without my professional identity to lean on, I felt exposed. Uncertain. Like I was showing up to the conversation empty-handed.

The main focus of the retreat was to choose a "piece of work"—a blocker present in our lives that we wanted to examine with the group. We didn't know this coming in, and had about 24 to 48 hours to decide.

I made a list of six potential blockers. All legitimate. All things I genuinely wanted to work through.

But when it came time to go before the group, it hit me: what I was feeling right now, at this retreat, might be the most profound blocker of all.

Without the ability to talk about work, I had no conversational fall-back. I felt extremely uncomfortable, like I had no clue how to establish connection. Or perhaps more telling: I wasn't sure I was worthy of it.

And here's the thing—I haven't had a big professional win since I published my book. (Big, according to my admittedly ridiculously high standards.) Which means I've been operating this way for a while now: the belief that my worthiness of connection is predicated on my happiness with my work. When my career feels stalled, I feel invisible. Uninteresting. Not enough.

I'd been using my profession as an identity crutch.


The mortification settled in slowly, then all at once. I'm a coach. I teach women to expand their worth, inside and out. I specialize in salary negotiation—helping women see and claim their value. And here I was, confronted with the fact that I still had some serious work to do on the "inside" part.

But then another layer revealed itself, and this one was even more uncomfortable:

The real crutch wasn't just using work to prove my worth. The real crutch was using the narrative "I'm not worthy of connection" to avoid connecting at all.

Because I'm scared of it.


If I'm being really, truly, and brutally honest, so much of my life has been constructed around proving my worth.

Earning attention, love, and affection through accomplishments and accolades. Build the resume. Get the degrees. Publish the book. Rack up the testimonials. Create an identity so impressive that people have to pay attention.

It's a strategy that works, to a point. People do pay attention. They hire me, follow me, listen to me.

But it's also transactional. It's safe. It lets me control the narrative and keep actual intimacy at arm's length.

Real connection—the kind where you show up without your credentials, without your highlight reel, without proof that you're worth the time—that's terrifying. Because what if you show up as just you and it's not enough? What if they look at you and find nothing interesting there?

The irony isn't lost on me. I teach women to negotiate their salaries by knowing their worth independent of external validation. I tell them that their value isn't determined by their last performance review or their title or whether their boss notices them.

Turns out, I was teaching what I most needed to learn.


So what do we do with this?

I'm not going to pretend I've solved this. I'm still in it. But I am learning to recognize my shields, and recognition is the first action.

Here's what I'm starting to practice, and what I want to invite you to consider:

Notice your conversational defaults

What do you reach for when you meet someone new? Your job title? Your company? Your latest project? There's nothing wrong with talking about work—but pay attention to when you reach for it and why. Are you sharing because it's genuinely relevant, or are you using it as a shield?

Try this: Think about your last three social interactions. How quickly did work come up? Who brought it up? What were you hoping would happen when you mentioned it?

Try the "No Crutch" experiment

Go to one social event—or even one conversation—where you don't mention your job title first. See what happens. Notice the discomfort. You don't have to fix it or make it go away. Just observe it.

Try this: Before your next social gathering, write down three things about yourself that have nothing to do with your career. Practice introducing yourself with one of them. Pay attention to how it feels in your body when you resist reaching for your professional identity.


Ask different questions

Instead of "What do you do?", try asking questions that invite real connection: "How are you feeling lately?" or "What's been on your mind?" or "What are you excited about right now?" Yes, these feel vulnerable. Yes, you might get some surprised looks at first.

Try this: In your next three conversations, lead with one of these questions instead of work talk. Notice what happens—both in the other person and in yourself. Do the conversations go deeper? Do you feel more or less comfortable? There's no right answer, just information.

Do a worthiness audit

When do you feel most yourself? What's present in those moments? What's absent? Who in your life loves you for reasons that have nothing to do with what you produce?

Try this: Answer these questions on paper: What would scare you more—losing your job title, or losing your best friend's phone number? Be honest about why. Then ask: What else is there? What would I talk about if my career disappeared tomorrow? Who am I when I'm not producing anything?

Knowing your worth is quiet. It doesn't need an audience. It doesn't require validation or applause. It just is.

Needing to prove your worth is exhausting. It's a performance that never ends, because the evidence is never quite enough.

I'm learning—slowly, uncomfortably—to show up without my resume. To let conversations unfold without steering them toward my accomplishments. To sit in the terrifying space of just being a person talking to another person, with nothing to prove and nothing to hide behind.

I'm learning that connection isn't something I earn. It's something I allow.

Maybe you vomited on the bus too—metaphorically speaking. Maybe you've arrived at your own retreat, whatever form it takes, and realized that the thing you thought made you interesting is actually the thing keeping you from being known.

Maybe it's time to empty out. To receive what's waiting on the other side of the shield.

I want to hear from you: What's your version of work talk? What do you hide behind?


Reply and tell me. Let's practice the thing that scares us.

Because here's what I'm learning: the most worthwhile connections happen when we stop trying to prove we're worthwhile.

Now go get paid.

x Claire

PS Loved this email? Share it with anyone you think could benefit!

PPS Stuck in a rut? Book me for a 30 minute coaching session 🤗


Resources

Looking for a job?

LLC of Me


Dreaming of a new career?

Pivot Pathfinder


Preparing to negotiate?

Earn Better


Seeking guidance?

Explore Coaching

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There’s a moment—maybe it’s during childbirth, maybe it’s a health scare, maybe it’s just Tuesday morning and you realize you can’t do this anymore—when your entire career suddenly stops making sense.

You thought you had it figured out. Good job, decent pay, looks great on paper. But something shifted. And now you’re drowning in “what ifs” and paralyzed by self-doubt.

In my latest coaching session, I walked “Georgia” (real person, changed name) through exactly this crossroads.

After a traumatic birth where she watched doctors “casually” save her life, she couldn’t shake one question: Should I leave my 15-year marketing career to become a nurse?!

Here’s what we discovered—and why it matters for anyone questioning their career right now:

The problem isn’t that you need to make the “right” choice between two options. The problem is that you’re thinking in binaries at all.

In this week’s Substack, I break down:

  • Why trauma doesn’t give you new values—it just forces you to finally listen to the ones you’ve been ignoring
  • The “third path” framework that lets you stop choosing between your expertise and your passion
  • How to reality-test ANY career move before you blow up your life
  • The 20-minute daily practice that beats waiting until you hit rock bottom

I'm looking for brave women who...

👉 Want a free 45 minute coaching session with me in exchange for allowing me to post on the Ladies Get Paid podcast and Substack. You're off camera and can change your name. It's a beautiful way to get support while supporting others.

I specialize in helping women who want to build a better work-life, activate their potential, and achieve success without self-sacrifice.

👉 Learned to embrace their worth the hard way—through underpaid years, toxic situations, or moments of accepting far less than they deserved. If you've transformed from questioning your value to claiming it (and you're willing to share the messy middle of that journey), I'd love to feature your story in my upcoming series in this newsletter and on the Ladies Get Paid Instagram.

Hi, I'm Claire Wasserman and I help you expand your worth, wealth, and wellbeing.

I'd love to support you - learn more here.

1333 N Sweetzer Ave, Apt 3B, West Hollywood, CA 90069
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