CLEVER OCTOPUS LLC
Clever Octopus exists for senior professional women who built something remarkable in the corporate world—then had the chapter close before they were ready. We help displaced executives move past the panic-applying phase and design what comes next on their own terms.
We're not outplacement. We're not resume optimization. We're two women who were laid off from senior roles in our fifties and built the advisory practice we wish someone had built for us. We offer structured, honest work that starts with one question: what do you actually want from the next ten years?
Our work begins with the Never Again Audit, a free 15-minute exercise that helps you write down the criteria your next chapter has to meet. From there, we offer real conversations and working sessions that turn a spinning mind into a clear direction. No corporate playbook. No follow-your-passion filler. Just the compass you need to choose your next role instead of defaulting into it.
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Our Services
The Never Again Audit
A free 15-minute structured exercise that walks you through writing down the criteria your next chapter has to meet. You'll walk away with a clear list of what you refuse to repeat, the conditions that made your last role feel wrong, and honest language for what you actually want next.
Honest Read Conversation
A real 30-minute call with Heather or Casey. We'll read what you're sitting with, name the patterns underneath, and tell you what we'd actually recommend doing in the next thirty days. No sales pitch—just an honest assessment of where you are.
The Compass Session
A 90-minute structured working session. One of us, you, your Never Again list, and one written direction in your inbox by the next morning. This is where you turn a spinning mind into a clear decision about what comes next.
Career Transition Advisory
Ongoing support for senior professional women designing their next chapter. We help you navigate displacement with intention, build careers that fit your life, and move forward without defaulting into the wrong answer.
