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:

1. Choose a check-in date (3–6 months out)

2. Assess progress toward affordability and readiness

3. Identify barriers if progress isn't happening

4. Choose an exit date — even if it's a year or more away

5. 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:

1. Validate the feeling — moment or season?

2. Get specific about what it would take to afford leaving

3. 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 [email protected]

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.