The Career Clinic Podcast

Ronnie Dickerson Stewart
  • 5.0 (42)
  • CAREERS
  • UPDATED WEEKLY

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!

  1. 97. This Is the Year That Will Completely Change Your Relationship With Work

    8H AGO

    97. This Is the Year That Will Completely Change Your Relationship With Work

    Episode 97: This Is the Year That Will Completely Change Your Relationship With Work The Career Clinic Podcast Host: Ronnie Dickerson Stewart Episode Overview In Episode 97, Ronnie shifts the tone of the podcast to address something urgent and real: the reality that job security, as many of us once understood it, has fundamentally changed. This episode is less about tactics and more about a mindset shift. If you've felt like you're one restructure away from disruption, or you've watched talented people around you recalibrate unexpectedly, this conversation is for you. What You'll Hear in This Episode ✔️ Why job security has shifted — even at strong companies ✔️ Why this moment requires a new blueprint ✔️ How generational advice still makes sense — but needs updating ✔️ The danger of building provision in only one place ✔️ What it means to adopt a portfolio career mindset ✔️ Why this year may need to be the year you rethink your relationship with work The Mindset Shift: From Employee to "You Inc." Rather than offering a checklist of tips, Ronnie invites listeners into a deeper recalibration. What if you thought of yourself as "You Inc."? What if your primary employer was You Inc., and your job was simply one client of many possible revenue sources, identity anchors, or professional expressions? This is not just about side hustles. It's not a hustle culture pitch. It's about strategic optionality. It's about understanding that your time, skills, relationships, and brand have value beyond one organizational structure. A portfolio career mindset does not require you to quit your job. It requires you to think differently about permanence, agency, and alignment. Why This Year Matters 🤎 This episode is a call to stop pretending permanence still operates the way it once did. It is an invitation to rethink your relationship with work before something forces you to. We deserve better. And when we cannot immediately get better systems, we build better strategies for ourselves. Stay Connected 🤎 📩 Join the OhHeyMonday Newsletter Weekly reflections and leadership insight 👉🏾 www.ohheyjoin.com 🤝 Work With Ronnie / OhHeyCoach Executive coaching and leadership development 👉🏾 www.ohheycoach.com Final Thought 🤎 This may be the year that completely changes your relationship with work — not because something collapses, but because you finally choose to design it differently. See you next week!

    16 min
  2. 96. Stop Waiting to Be Ready

    FEB 12

    96. Stop Waiting to Be Ready

    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.

    26 min
  3. 95. When You Can't Afford to Leave

    FEB 5

    95. When You Can't Afford to Leave

    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 not failing. You're in a season that requires strategy, patience, and self-trust. And every aligned step you take brings you closer to the exit you deserve. See you next Wednesday.

    29 min
  4. 94. Side-Hustling, New Roles, Motivation | Ask OhHeyCoach

    JAN 31

    94. Side-Hustling, New Roles, Motivation | Ask OhHeyCoach

    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.

    55 min
  5. 93. How to Know When to Go

    JAN 30

    93. How to Know When to Go

    Episode 93: How to Know When to Go The Career Clinic Podcast Host: Ronnie Dickerson Stewart Episode Overview Welcome to Week Four — the final week — of The Career Clinic Podcast January Intensive Series. In Episode 93, Ronnie tackles one of the most consequential career questions many people face: How do you know when it's time to go? Not quitting reactively. Not staying out of fear, loyalty, or inertia. Not confusing a hard season with a finished one. This episode offers a grounded, practical approach to discerning when a chapter is complete — and when what's actually required is a pause, reset, or renegotiation instead of an exit. What You'll Learn in This Episode: ✔️ Why "stay or go" is rarely a simple yes/no decision ✔️ How to distinguish misalignment from normal discomfort ✔️ A practical framework to assess your current season ✔️ The difference between a Going Season and a Woahing Season ✔️ Why staying too long can quietly erode health and momentum ✔️ How to prepare for transitions without panic or urgency ✔️ What aligned leaving actually looks like The Core Framework: Earning, Learning, Leveraging ✍🏾 Ronnie introduces a decision-making framework she uses frequently with coaching clients navigating inflection points. Ask yourself three questions: 1. Am I earning? Not just salary — but fair compensation, resources, respect, and support relative to the value you're creating. 2. Am I learning? Are you still growing, stretching, or building skills that matter for your future? 3. Am I leveraging? Is this role, leader, or organization creating momentum, credibility, or access for what's next? If the answer is no to two or more, it's time to pause and evaluate — not panic, but pay attention. When It May Be Time to Go If earning, learning, or leveraging cannot be improved — even after conversations, negotiation, or boundary-setting — that's often a signal the season may be ending. Going doesn't require immediate action. It requires clarity. Key questions include: What would need to change for this to work? Is that change realistically possible here? If not, what provision and timeline would I need to exit well? Leaving well is a process, not a reaction. An Important Signal: Languishing 🤎 Ronnie names a signal that deserves serious attention: languishing. This isn't a bad week or temporary fatigue. It's the slow loss of energy, clarity, and connection to yourself. Languishing often costs: Physical and mental health Personal relationships Confidence and self-trust Long-term career momentum No role is worth sustained erosion. Going Season vs. Woahing Season This episode adds nuance using Ronnie's Five Seasons Framework, with a clear distinction between Going Season and Woahing Season. Going Season A season of intentional preparation to leave — a role, organization, identity, or chapter that no longer fits. The clarity here is steady and persistent, not emotional or reactive. Woahing Season A pause season. Not leaving — but slowing down, repacing, restoring energy, resetting boundaries, or addressing overextension. Woahing is about saying "Hold on", not "I'm done." Leaving during a Woahing Season often means carrying the same patterns into the next chapter. When Going Isn't Your Choice Ronnie also addresses involuntary transitions — layoffs, restructures, and role eliminations. Key reminders: These are business decisions, not reflections of your worth You still get to shape your narrative Preparation protects you, even if nothing changes Preparation can include: Maintaining relationships inside and outside your organization Staying visible without becoming performative Creating financial runway when possible Paying attention without spiraling What Going Well Requires If you're clear that it's time to go, this episode emphasizes three essentials: Clarity Know what you're moving toward — even if it's rest, recovery, or space. Planning Timeline, provision, and next steps matter. Grace Leaving is emotionally complex, even when it's right. Aligned exits are thoughtful, not dramatic. Listener Reflection 🤎 This week, complete an Earning, Learning, Leveraging audit. Then ask: Am I in a Going Season or a Woahing Season? What one step would bring clarity right now? Discernment is part of leadership. There's no rush. Links & Resources 🤎 📩 Join the OhHeyMonday Newsletter Weekly reflections, tools, and leadership guidance 👉🏾 www.ohheyjoin.com 📝 Ask OhHeyCoach Submit a question for a future episode 👉🏾 https://form.typeform.com/to/ja89DHpT 🤝 Work With OhHeyCoach Executive coaching, leadership development, and career design 👉🏾 www.ohheycoach.com 📬 Contact info@ohheycoach.com

    28 min
  6. 92. Managing Your Stakeholders (Without Losing Yourself)

    JAN 28

    92. Managing Your Stakeholders (Without Losing Yourself)

    Episode 92: Managing Your Stakeholders (Without Losing Yourself) The Career Clinic Podcast Host: Ronnie Dickerson Stewart Episode Overview Welcome to Week Four — the final week — of The Career Clinic Podcast January Intensive Series. This week is focused on designing your career on purpose, with practical tactics you can apply immediately. In Episode 92, Ronnie tackles a topic that consistently trips up capable, thoughtful professionals: managing your stakeholders — without burning out, people-pleasing, or losing yourself in the process. This conversation reframes stakeholder management away from "corporate politics" and toward self-advocacy, stewardship, and clarity. The goal isn't to perform or overextend. It's to ensure the people who influence your progress and provision actually understand your value, priorities, and boundaries. What You'll Learn in This Episode: ✔️ What "stakeholders" really means — beyond your direct manager ✔️ Why stakeholder complexity increases as you become more senior ✔️ How mismanaged relationships lead to burnout, resentment, and missed opportunity ✔️ The shift from passive to participatory career management ✔️ A practical framework for managing stakeholder relationships intentionally ✔️ How to advocate for yourself without shrinking or over-explaining ✔️ When it's time to adjust — or exit — a stakeholder relationship Who Are Your Stakeholders, Really? In this episode, Ronnie defines stakeholders as anyone who influences your progress or your provision. That can include: Your manager and leadership team Skip-level leaders Clients and vendors Cross-functional partners Board members Collaborators on key initiatives As careers advance, stakeholder webs become more complex — not simpler. Managing up, down, and across requires intention, not assumption. The Core Shift: Passive → Participatory A common mistake many people make is waiting to be understood. They assume: Stakeholders know what they're working on Stakeholders understand what they need Past performance will speak for itself But assumption is not a strategy. Ronnie emphasizes that stakeholder management means actively participating in shaping how your work, value, and priorities are understood — rather than leaving it to chance. The Four Pillars of Stakeholder Management ✍🏾 Ronnie introduces a practical framework built on four elements: Anticipation Understanding what your stakeholders care about before they have to say it. Communication Sharing information in ways that are useful to them, not just you. Translation Framing your work in language that resonates with their priorities. Consistency Showing up in predictable, reliable ways over time. These four elements create clarity, trust, and momentum. Not All Stakeholders Care About the Same Things A key insight from the episode: stakeholders optimize for different outcomes. For example: A manager may care about execution and morale A skip-level leader may care about risk and alignment One client may prioritize speed, another results One partner may value collaboration, another optics Treating every stakeholder the same often creates friction. Managing relationships well requires understanding what each person is measured on and worried about. How to Understand What Your Stakeholders Care About Ronnie offers seven diagnostic questions to help you gain clarity: What pressure are they under? What are they being measured on? What keeps them up at night? What do they need to feel successful? What does success look like from their perspective? How does your work help solve their problem? How does your contribution make their job easier or their goals more achievable? When you can answer these, you can manage relationships strategically — not transactionally. Say vs. Show: Managing Perception Stakeholders don't experience your intentions — they experience patterns. This episode revisits the idea of closing the gap between: What you say you are What stakeholders actually experience from you Visibility here isn't about noise. It's about intentional surfacing of: Wins Progress Challenges Context that needs translation What gets shown consistently is what gets trusted. When Stakeholders Are Misaligned or Difficult Ronnie addresses a reality many listeners face: Conflicting priorities between stakeholders Unclear or inconsistent leadership Relationships that create ongoing friction The guidance: Name what's true without dramatizing it Focus on what you can influence (communication, framing, boundaries) Adjust strategy without abandoning yourself Recognize when a relationship may no longer be worth the energy it requires Not every stakeholder relationship is meant to be preserved at all costs. A Practical Stakeholder Audit 🤎 Ronnie closes the episode with a clear, actionable exercise: 1. Identify Your Stakeholders List anyone who influences your progress or provision. 2. Clarify What They Care About Note their priorities, pressures, and success metrics. 3. Identify Gaps Where are you unclear, inconsistent, or silent? 4. Choose One Small Shift One conversation, one update, one boundary — not an overhaul. Small adjustments compound. What This Episode Reinforces Stakeholder management is about protection, not performance Clarity reduces friction Advocacy builds provision Relationships compound over time You don't need to manage everyone — just the relationships that matter most What's Coming Next Tomorrow's episode tackles one of the hardest career decisions many people face: when to stay — and when to go. Links & Resources 🤎 📩 Join the OhHeyMonday Newsletter Weekly reflections, tools, and leadership guidance 👉🏾 www.ohheyjoin.com 📝 Ask OhHeyCoach Submit a question for a future episode 👉🏾 https://form.typeform.com/to/ja89DHpT 🤝 Work With OhHeyCoach Executive coaching, leadership development, and career design 👉🏾 www.ohheycoach.com 📬 Contact info@ohheycoach.com Final Thought 🤎 This is grown-folks career stewardship. I'll see you tomorrow.

    18 min
  7. 91. Negotiation as Self-Advocacy

    JAN 28

    91. Negotiation as Self-Advocacy

    Episode 91: Negotiation as Self-Advocacy The Career Clinic Podcast Host: Ronnie Dickerson Stewart Episode Overview Welcome to Week Four — the final week — of The Career Clinic Podcast January Intensive Series. This week centers on designing your career and life on purpose, and in Episode 91, Ronnie reframes negotiation as something far bigger than salary discussions or offer letters. This episode positions negotiation as self-advocacy — a posture and practice that helps create provision and margin across your work and life. Whether you're staying put, stepping up, or preparing for what's next, negotiation is about shaping the conditions that allow you to succeed and sustain yourself over time. Negotiation isn't about winning. It's about aligning the terms of engagement with the life you're trying to live. What You'll Learn in This Episode: ✔️ Why negotiation is about more than compensation ✔️ The difference between negotiating outcomes vs. negotiating conditions ✔️ How provision and margin protect against burnout and resentment ✔️ Common negotiation moments people miss entirely ✔️ Why half-negotiating often leads to overwhelm later ✔️ How to prepare for negotiation conversations with clarity and confidence ✔️ How to frame negotiations as alignment, not demands The Core Reframe: Negotiation Creates Provision and Margin Ronnie introduces two key concepts that ground this episode: Provision The resources, support, authority, and clarity you need to do your work well and live well — including team size, budget, tools, access, decision-making power, and fair compensation. Margin The breathing room that makes work sustainable — flexibility, boundaries, time, rest, and space to think strategically instead of constantly reacting. Negotiation is how you actively shape both. Where Most People Stop Too Soon This episode names a common pattern: people negotiate the number, but not the conditions. Examples include: Negotiating salary but not team size or resources Accepting a promotion without clarifying decision authority Getting a raise without discussing the path forward Absorbing additional scope without resetting expectations Working unsustainable hours without renegotiating boundaries The result is often short-term wins followed by long-term strain. Missed Negotiation Moments to Watch For ✍🏾 Ronnie walks through several moments that are actually invitations to negotiate: Promotions or role expansions Strong performance reviews Increased scope or absorbed work Projects that fail due to structural gaps Unsustainable workloads or expectations Negotiation doesn't only happen at offer stage — it happens whenever the terms of engagement change. How to Prepare for Negotiation Conversations Ronnie offers a practical, repeatable approach: 1. Get Clear on What You're Asking For — and Why Know what success requires in real terms. 2. Invite the Conversation Use language that signals alignment and gives space to prepare. 3. Frame for Mutual Success Position the conversation around outcomes and sustainability, not demands. 4. Bring Context and Data Decision-makers don't always see what you see — help them understand. 5. Get Curious About Pushback Curiosity creates collaboration and better outcomes. 6. Offer Options, Not Just Problems Solutions invite partnership. What This Episode Is — and Isn't This episode is not about: Negotiating for sport Being adversarial Pushing without context It is about: Advocating for yourself clearly Designing conditions that support long-term success Treating negotiation as a leadership skill Understanding that the terms you accept shape the life you live This Week's Reflection 🤎 Identify one upcoming moment where a negotiation is needed — a review, role change, scope shift, or workload concern. Ask yourself: What do I need to succeed here? What conditions would make this sustainable? How can I frame this as alignment? That's the work. What's Coming Next The next episode continues this thread with a focus on stakeholder management — and how to build partnerships that support your success instead of leaving you to carry everything alone. Links & Resources 🤎 📩 Join the OhHeyMonday Newsletter Weekly reflections, tools, and leadership guidance 👉🏾 www.ohheyjoin.com 📝 Ask OhHeyCoach Submit a question for a future episode 👉🏾 https://form.typeform.com/to/ja89DHpT 🤝 Work With OhHeyCoach Executive coaching, leadership development, and career design 👉🏾 www.ohheycoach.com 📬 Contact info@ohheycoach.com Final Thought 🤎 Negotiation isn't about asking for more. It's about asking for what makes success possible. The terms you accept today shape the life you live tomorrow. I'll see you in the next episode

    26 min
  8. 90. Stop Waiting For Permission

    JAN 27

    90. Stop Waiting For Permission

    Episode 90: Stop Waiting for Permission The Career Clinic Podcast Host: Ronnie Dickerson Stewart Episode Overview Welcome to Week Four — the final week — of The Career Clinic Podcast January Intensive Series. This week brings together the core themes of the series: agency, design, decision-making, and forward movement. In Episode 90, Ronnie names a pattern she sees repeatedly among capable, accomplished people: waiting for permission. Permission to apply. Permission to pivot. Permission to leave. Permission to want something different than what once made sense. This episode is a grounded conversation about reclaiming agency, understanding the cost of waiting, and learning how to move forward with intention — even when certainty isn't available. What You'll Learn in This Episode: ✔️ Why permission rarely arrives — especially later in your career ✔️ How "being prudent" quietly turns into self-delay ✔️ The difference between strategic patience and stalled movement ✔️ Why certainty almost never comes before action ✔️ How external validation slowly erodes leverage ✔️ What it looks like to design your next chapter on purpose Why We Wait for Permission Ronnie breaks down common reasons people get stuck waiting: Wanting certainty before moving Seeking validation from others Believing there is a "right" way to want success Fear of undoing credibility already earned Feeling bound to past decisions At a certain point, waiting stops being thoughtful — and starts limiting momentum. The Real Cost of Waiting This episode names what waiting often costs: Time Time spent waiting is time not spent building toward what matters now. Opportunity Movement creates learning. Waiting delays it. Leverage The longer you wait, the more approval starts to matter. Agency Over time, waiting teaches you to defer your own judgment — and that's hard to reverse. A Personal Story on Self-Permission Ronnie shares her own experience leaving a successful corporate career to build OhHeyCoach — not impulsively, but intentionally. She talks through: How long the decision took Why permission never came What planning actually looked like Why clarity followed action, not the other way around The takeaway is practical: permission is something you give yourself — after thought, reflection, and design. How to Stop Waiting and Start Designing ✍🏾 1. Name the Permission You're Waiting For Be specific. Vague waiting is harder to move through. 2. Ask: "What Would I Do If I Already Had Permission?" This question surfaces clarity quickly. 3. Design the Thing You're Waiting On Draft the role, the pivot, the next chapter — even if it's rough. 4. Identify the First Two Steps Not the full plan. Just the next right moves. What This Episode Is — and Isn't This is not a call to be reckless or impulsive. It is a reminder that: Thoughtful decisions don't require unanimous approval Readiness often follows movement You are allowed to evolve beyond old definitions What's Coming Next The next episode continues this theme with a focus on negotiation as self-advocacy — reframing negotiation as a life skill, not just a workplace tactic. Links & Resources 🤎 📩 Join the OhHeyMonday Newsletter Weekly reflections, tools, and leadership guidance 👉🏾 www.ohheyjoin.com 📝 Ask OhHeyCoach Submit a question for a future episode 👉🏾 https://form.typeform.com/to/ja89DHpT 🤝 Work With OhHeyCoach Executive coaching, leadership development, and career design 👉🏾 www.ohheycoach.com 📬 Contact info@ohheycoach.com Final Thought 🤎 You don't need permission to think clearly, plan thoughtfully, or move forward with intention. You are allowed to decide — and design — what's next. I'll see you in the next episode. 🤎

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About

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!

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