It might be time for a career shift…here’s how to know (and what to do next)

Earn better.

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If everyone who opened my emails gave $5 to my Kickstarter, I could stop bothering you about it πŸ˜‰ πŸ™

I’ve been feeling the itch lately.

You know the oneβ€”it starts as a pebble in your shoe, barely noticeable. Then it becomes a rock. It’s not something you can name exactly. More of an absence. A wondering. A wandering.

Typically, I just work harder, trying to override it with more to-dos. But the universe has a way of staging aggressive interventions.

Mine came in the form of a Kickstarter campaign that launched with a thud. Something I’d poured my heart into for two years, thinking “this is it.” The result? Just over 100 contributors from an email list of 20,000 opens.

That gap between expectation and reality? It forced me to stop and listen to what the itch had been trying to tell me all along.

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When disappointment becomes data

When something doesn’t work as expected, it’s devastating. But it’s also an opportunity to ask yourself the hard questions you’ve been avoiding:

  1. Do I still want this?
  2. Do I still want it in this way?
  3. Divorced from outcomes, what parts of the process actually light me up?

Here’s what I’ve learned: that itch you feel isn’t just dissatisfaction. It’s your intuition telling you that you’ve outgrown where you are. You might have a slight inkling of where to orient next, but the future feels terrifyingly unknown.

That’s actually a good thing.

Having an extremely specific vision would mean you’re closed off to possibilities. I think of this process like having a block of marbleβ€”your job is to chip away at it, step back, and see what’s emerging.

You can’t force it into a predetermined shape. You have to step forward through action, and then step back through perspective. What shape is it – are you – becoming?

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Signs you’re ready for a shift

I’m deep in this process right now. More days than not, I feel frustrated. Disappointed. My work isn’t converting to money. Resentment is building. But these aren’t character flawsβ€”they’re signals.

Here’s how to know if you’re ready to move on:

  • Sunday nights fill you with dread instead of anticipation
  • You’re going through the motions but the spark is gone
  • You find yourself constantly daydreaming about “what if”
  • The work that once energized you now drains you
  • You’re jealous of people doing completely different things
  • Small setbacks feel catastrophic (because deep down, you’re looking for an exit)

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From clarity to action

While my Kickstarter’s poor launch humbled me, it made me do something simple but powerful: I analyzed what IS working.

What I found:

  • I love problem-solving (especially through writing)
  • People consistently open and respond to my newsletters
  • The moments when I help someone see their situation differently make everything worth it

What wasn’t working:

  • Trying to force a product that the market doesn’t want
  • Ignoring the signals that my energy was shifting
  • Pushing harder instead of pivoting smarter

So I picked a direction that honored what was already working: more writing. Focusing on my memoir. This newsletter. Launching a Substack. Going deeper with the medium that already resonates.

My next steps are simple: connect with people who’ve made writing and content creation their living. Learn from those who’ve walked this path. Start before I’m ready.

Your turn

If you’re feeling the itch (or the pebble!), here’s your homework:

  1. Audit your energy: List what you do in a typical week. Mark each item with a + (energizing) or – (draining). Look for patterns.
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  2. Find the thread: What do the energizing activities have in common? What skills or qualities keep showing up?
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  3. Start small: You don’t need to quit your job tomorrow. Pick one tiny experiment that moves you toward what’s working. One coffee chat. One blog post. One application.
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  4. Ask better questions: Instead of “What should I do with my life?” try “What would I try if I knew I couldn’t fail?” or “What would this look like if it were easy?”

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The season you’re in

Here’s what I’m learning: This isn’t a wrong turn. It’s a season of becoming.

Sometimes what looks like failure is just life’s way of course-correcting us toward what we actually want, not what we thought we should want. The Kickstarter that is “failing”? It succeeded in showing me what needed to shift.

The itch you’re feeling? It’s not a problem to be solved. It’s an invitation to grow into the next version of yourself.

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Please Support The Practice

​The Practice is a set of 30 cards that systemically rewires your brain away from self-doubt to self-trust.

I’m currently pre-selling through Kickstarter and we have until October 19th to raise the funds we need. It’s all-or-nothing and you’re the one who decides if this fails or succeeds. If my emails have helped you over the years, please consider supporting.

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With gratitude and vulnerability,

x Claire

Resources

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Looking for a job?

​LLC of Me​

Dreaming of a (potential) new career?

​Pivot Pathfinder​

Preparing to negotiate?

​Earn Better​

Seeking guidance?

​Explore Coaching​

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