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The Career Clinic Podcast

The Career Clinic Podcast

Von: Ronnie Dickerson Stewart
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I'm so excited to introduce The Career Clinic, powered by OhHeyCoach, with your host, me, Ronnie Dickerson Stewart! I've coached & consulted with countless individuals from interns to C-suite leaders on how to navigate their stickiest career moments. In this clinic and in the time we get to share, I hope to do the same with you! Whether you're in the "staying, growing or going" stage, on this podcast, no career topic is off the table. Truth Moment: Everyone does not have equal access to executive coaching and career advancement resources. I believe everyone should be able to access tools to chart a successful career path that uniquely serves them. So YOU can think of me as a coach, consultant, or mentor who is one click and download away. Welcome to The Career Clinic Podcast (powered by OhHeyCoach), I can't wait to see how we learn and grow together! Erfolg im Beruf Ökonomie
  • 96. Stop Waiting to Be Ready
    Feb 12 2026
    Episode 96: Stop Waiting to Be Ready The Career Clinic Podcast Host: Ronnie Dickerson Stewart Episode Overview Welcome back to The Career Clinic Podcast 🤎. In Episode 96, Ronnie addresses something that quietly stalls more careers and ideas than lack of talent ever does: the habit of waiting to feel ready. This episode explores why readiness is often a moving target, how over-preparation can become avoidance, and why clarity rarely arrives before action. Whether you're considering a pivot, launching something new, raising your hand, or finally starting the thing you've been thinking about for years, this conversation is about moving forward without the illusion of perfect timing. What You'll Learn in This Episode ✔️ Why readiness is more of a decision than a feeling ✔️ The hidden cost of waiting too long ✔️ How over-preparation can delay execution ✔️ Why waiting for permission slows momentum ✔️ The myth of perfect timing ✔️ Three practical ways to move before you feel fully ready The Readiness Trap When people say, "I'm not ready," it's rarely about actual capability. More often, it's about exposure, uncertainty, or fear of being seen before everything feels polished. Ronnie reflects on launching this podcast without a 100-episode plan, stepping away from a C-suite role without a fully mapped five-year blueprint, and beginning the process of writing a book without knowing every detail of how it would unfold. In each case, clarity followed movement. It did not precede it. The idea that you will feel completely prepared before taking action is one of the most convincing myths in professional life. The Cost of Waiting 🤎 We often overestimate the risk of starting and underestimate the cost of delaying. Waiting can erode confidence. It can shrink momentum. It can quietly chip away at self-trust. The longer you sit with something you know you want to pursue, the louder doubt becomes and the smaller your original conviction feels. At some point, the cost of waiting outweighs the discomfort of beginning. Three Common Disguises of "I'm Not Ready" Over-preparation. Taking another course, reading another book, asking five more people for input. Preparation is wise. Endless preparation that never converts to execution is avoidance. Waiting for permission. There is rarely a formal invitation to step into your next chapter. No one is coming to certify you as ready. Authority is often assumed, not granted. Perfect timing. There will always be a reorg, a busy season, a market shift, or a personal responsibility that makes now feel inconvenient. Timing matters, but perfection is not a prerequisite for progress. How to Move Before You Feel Ready ✍🏾 First, shrink the ask. Instead of taking the full leap, take the next step. Send the email. Outline the idea. Have the conversation. Test the concept. Small action builds real clarity. Second, set a decision date. If something has been circulating in your mind for months, give yourself a deadline to decide your next move. Not the entire plan — just the next move. Third, borrow belief. If your fear is louder than your confidence, talk to someone who can hold perspective with you. A trusted friend, mentor, or coach can help steady the narrative long enough for you to move. Listener Invitation 🤎 If something has been tugging at you — an idea, a pivot, a conversation, an application — consider whether you're truly unprepared or simply uncomfortable. You may not feel ready. That doesn't mean you aren't capable. What's Next We are approaching Episode 100 in March, and something special is coming 🤎. New episodes of The Career Clinic Podcast drop every Wednesday. Make sure you follow or subscribe so you don't miss what's next. If this episode resonated, share it with someone who may be waiting on themselves. Stay Connected 🤎 📩 Join the OhHeyMonday Newsletter Weekly reflections and grounded leadership tools 👉🏾 www.ohheyjoin.com 🤝 Work With Ronnie / OhHeyCoach Executive coaching and leadership development 👉🏾 www.ohheycoach.com Final Thought 🤎 Readiness often arrives after you begin, not before. If you've been waiting for a feeling to confirm what you already know, it may be time to trust your judgment and take the next step. See you next Wednesday.
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    26 Min.
  • 95. When You Can't Afford to Leave
    Feb 5 2026
    Episode 95: When You Can't Afford to Leave The Career Clinic Podcast Host: Ronnie Dickerson Stewart Episode Overview Welcome back to The Career Clinic Podcast 🤎. We're officially beyond the January Intensive and settling into our regular rhythm — with new episodes dropping every Wednesday. In Episode 95, Ronnie addresses a reality that doesn't get talked about enough: what to do when you know you need to leave a role, but you can't afford to leave yet. This episode is for seasoned professionals — people who've built full lives, reputations, and responsibilities over time. When leaving isn't just about finding another job, but about untangling financial, relational, and reputational realities, courage alone isn't enough. You need strategy. What You'll Learn in This Episode: ✔️ How to tell the difference between a hard moment and a completed season ✔️ Why "I need to leave" deserves validation — not dismissal ✔️ The difference between a Going Season and a Woahing Season ✔️ What it really means to "afford" an exit ✔️ How to plan an aligned departure without rushing or burning bridges ✔️ How to reclaim agency even when you can't move yet First: Validate the Feeling If you're feeling like something needs to change, that feeling matters. But before making definitive moves, Ronnie invites you to ask: Is this a persistent knowing or a reaction to a hard week? Is this about misalignment — or overwhelm? What would need to change for me to want to stay? Is that change actually possible here? Sometimes leaving isn't the answer — redesigning your experience is. Other times, the clarity has been there for months, and it's time to pay attention. Moment or Season? This episode revisits a core distinction from the January Intensive: Going Season A season where clarity is steady and confirmed. You've tried to make it work, and it no longer fits. Woahing Season A pause season. You may need rest, renegotiation, or boundaries — not an exit. Leaving during a Woahing Season often means carrying the same patterns into the next chapter. Why Leaving Isn't Simple at This Stage For many listeners, leaving isn't just about a paycheck. It's about: Mortgages, childcare, healthcare, and family obligations Benefits, PTO, and supplemental support Access, visibility, and professional identity Reputation built over years Acknowledging these realities isn't fear — it's wisdom. The Core Question: What Would It Take to Afford Leaving? 🤎 Ronnie reframes the problem with a powerful question: What would it take for me to afford leaving — financially, reputationally, and relationally? Financially Know your real number. Not just salary — but total provision. Benefits, insurance, time off, and margin all count. Reputationally What would it take to ensure your reputation travels with you? Writing, speaking, visibility, and leadership beyond one organization matter. Relationally If your network is tied entirely to your current role, it's fragile. Building relationships beyond your employer creates optionality. Designing the Exit (Even If It's Not Today) You can't sit in "I need to leave but I can't" forever. Ronnie outlines a practical approach: Choose a check-in date (3–6 months out) Assess progress toward affordability and readiness Identify barriers if progress isn't happening Choose an exit date — even if it's a year or more away Work backward to design the transition A date turns "someday" into a plan. Write the Resignation Letter Even if you don't send it yet. Writing it: Clarifies intention Creates emotional buoyancy Helps you move with integrity Signals commitment to yourself Leaving well is something you design, not something that just happens. You Need a Crew 🤎 This is not a solo process. You need: A small, trusted, confidential crew People who can hold your truth Accountability without pressure Support without panic Be strategic about who knows — not everyone needs this information. Listener Assignment 🤎 If this episode meets you where you are: Validate the feeling — moment or season? Get specific about what it would take to afford leaving Choose two dates: a check-in date and an exit date Put them on your calendar. What This Episode Reinforces You're not stuck — you're in a strategic season Agency returns with action Planning reduces resentment Optionality creates power Leaving well takes time, and that's okay What's Next 🎧 New episodes of The Career Clinic Podcast drop every Wednesday. If you haven't already, follow or subscribe so you don't miss what's coming next. Links & Resources 🤎 📩 Join the OhHeyMonday Newsletter Weekly reflections and leadership guidance 👉🏾 www.ohheyjoin.com 🤝 Work With Ronnie / OhHeyCoach Executive coaching, leadership development, and career design 👉🏾 www.ohheycoach.com 📬 Contact info@ohheycoach.com Final Thought 🤎 If you know you need to go but can't afford to leave yet, you're ...
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    29 Min.
  • 94. Side-Hustling, New Roles, Motivation | Ask OhHeyCoach
    Jan 31 2026
    Episode 94: Side-Hustling, New Roles & Staying Motivated | Ask OhHeyCoach The Career Clinic Podcast Host: Ronnie Dickerson Stewart Episode Overview Welcome to Episode 94 — and the final episode of The Career Clinic Podcast January Intensive Series 🤎. Over the last four weeks, we've spent intentional time together resetting, recalibrating, and strengthening how you approach work, leadership, provision, and agency as you move into the year ahead. This final Ask OhHeyCoach episode brings the series home with listener questions about: Knowing when to leave a role Positioning yourself for opportunities that don't yet exist Doing more with less without burning out Building additional income streams responsibly Staying hopeful and steady in a difficult market This episode isn't about quick fixes. It's about discernment, preparation, and sustainable forward movement. What You'll Learn in This Episode: ✔️ How to make decisions when no option feels perfect ✔️ How to create opportunities instead of waiting for job postings ✔️ How to navigate "more work, fewer resources" without resentment ✔️ How to explore side income without jeopardizing your current role ✔️ Why motivation isn't enough — and what actually carries you through ✔️ How systems, community, and clarity support long-term momentum Key Themes from This Episode Decision-Making Without Certainty You won't always get clarity first. Often, clarity follows action — especially when you're honest about what you're optimizing for and the real cost of staying where you are. Creating Opportunity Many of the best roles are built, not posted. Relationships, visibility, and specificity make it easier for others to support and advocate for you. Capacity & Boundaries Doing more with less requires data, communication, prioritization, and boundaries. Silence and overextension are not sustainable strategies. Side Hustles & Additional Provision Building another stream of provision requires awareness of contracts, conflicts of interest, discretion, and timing. Protection and patience matter. Staying Steady in a Tough Market Motivation fades. Systems, inputs, community, and rest are what sustain you — especially when results take time. A Note of Gratitude 🤎 If you listened to one episode or all of them — thank you. Thank you for: Showing up for yourself Sharing this series with others Submitting thoughtful, honest questions Being part of this community This January Intensive has been one of the most meaningful projects Ronnie has created, and your presence made it what it was. What's Next for The Career Clinic Podcast 🎧 New episodes will drop weekly on Wednesdays. There's also a possibility of adding a second weekly episode on Mondays — more to come on that. The January Intensive will live here permanently, so revisit it anytime — and feel free to recommend it to someone who could use it. Stay Connected 🤎 📩 Join the OhHeyMonday Newsletter Weekly reflections, tools, and leadership guidance delivered every Monday 👉🏾 www.ohheyjoin.com 🤝 Work With Ronnie / OhHeyCoach Executive coaching, leadership development, and career design 👉🏾 www.ohheycoach.com 📸 Follow on Instagram @ronniedickersonstewart @ohheycoach 💼 Connect on LinkedIn Ronnie Dickerson Stewart 👉🏾 https://www.linkedin.com/in/ronniedickersonstewart/ 📝 Ask OhHeyCoach Submit questions for future episodes 👉🏾 https://form.typeform.com/to/ja89DHpT Support the Podcast 🤎 If this series served you, please: Follow or subscribe to The Career Clinic Podcast Rate and review the show Share it with someone who could use it These actions help the podcast reach more people who need grounded, honest career conversations. Final Thought 🤎 You don't have to have everything figured out. You just have to stay connected — to yourself, to your people, and to what matters. Thank you for starting the year here. I'll see you next Wednesday.
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    55 Min.
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