The Career Clinic Podcast
Host: Ronnie Dickerson Stewart
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.
✔️ 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
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.
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.
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.
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.
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.
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.
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.
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.
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
🎧 New episodes of The Career Clinic Podcast drop every Wednesday.
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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.
