85. Crews, Calendars, and Self-Commitment | Ask OhHeyCoach

Episode 85: Crews, Calendars, and Self-Commitment | Ask OhHeyCoach

The Career Clinic Podcast

Host: Ronnie Dickerson Stewart

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Episode Overview

Welcome to Ask OhHeyCoach Friday and the close of Week Two of The Career Clinic January Intensive.

In Episode 85, Ronnie responds to listener-submitted questions that bring this week’s themes together in real, lived ways — your calendar, your capacity, your crew, and your ability to keep commitments to yourself without guilt, perfectionism, or burnout.

This conversation reinforces a central idea from the week: improving your say vs. do ratio isn’t about doing more. It’s about designing systems, supports, and commitments that reflect your actual reality — and then honoring them with integrity.

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This Week’s Coaching Focus

Throughout this episode, Ronnie addresses how to:

• Close the gap between what you say matters and what your calendar reflects

• Move forward without certainty through testing and learning

• Assemble support without over-engineering or awkwardness

• Rebuild self-trust through small, kept commitments

• Release guilt and self-judgment in favor of honest design

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Listener Questions Answered in This Episode

1. “My calendar is telling on me.”
A listener shares that while they say health, rest, and boundaries matter, none of those priorities show up on their calendar — leading to guilt and self-doubt. Ronnie reframes this as a design issue, not a character flaw, and offers a grounded approach to rebuilding self-trust through evidence, not intention.

2. “I overthink everything — even small tests.”
This question explores perfectionism and analysis paralysis. Ronnie names overthinking as a form of self-protection and introduces a gentler reframe: moving from “Is this the right decision?” to “Is this safe enough to test?” Action becomes possible when learning, not certainty, is the goal.

3. “I know I need a crew, but asking for help feels awkward.”
A listener asks how to build support without it feeling transactional or forced. Ronnie normalizes the discomfort of vulnerability and emphasizes that most meaningful support starts awkward — and honest. A human ask, not a polished one, is often all that’s needed.

4. “Where do I even start with assembling a crew?”
This question names the overwhelm of coordinating people and securing buy-in. Ronnie reminds listeners that a crew is not built all at once. Support grows incrementally, starting with identifying one gap and inviting in one person or resource that can help lighten the load.

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Key Coaching Takeaways ✍🏾

✔️ Your calendar provides feedback — not judgment
✔️ Self-trust is built through small promises kept
✔️ Testing replaces perfection as the path to progress
✔️ A crew carries you and carries things with you
✔️ Support does not need to be perfectly coordinated to be effective
✔️ Alignment grows through honest, incremental change

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What This Episode Reinforces

• You don’t need a new planner to change your life — you need an honest one

• You don’t need certainty to move — you need permission to learn

• You don’t need a massive support system — you need intentional support

• You don’t need to do this alone

This episode ties together the practical and emotional realities of designing a year that reflects what actually matters.

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Looking Ahead

Next week, we begin Week Three of the January Intensive, focused on provision through visibility, voice, community, and connection — and how showing up with clarity (not performance) creates opportunity.

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Links & Resources 🤎

📝 Ask OhHeyCoach:
Submit your questions for a future Ask OhHeyCoach episode.
👉🏾 https://form.typeform.com/to/ja89DHpT

📩 Join the OhHeyMonday Newsletter:
Weekly reflections, tools, and grounded leadership guidance.
👉🏾 www.ohheyjoin.com

🤝 Work With Ronnie / OhHeyCoach:
Executive coaching, leadership development, and career design.
👉🏾 www.ohheycoach.com

📬 Contact:
[e-mail]

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Final Thought ✨

Alignment doesn’t come from big declarations.
It comes from honest design, supportive systems, and small promises kept.

Thank you for your questions, your trust, and for showing up for yourself this week.
I’ll see you next week. 🤎