The Courage Tax: What It Really Costs Women Lawyers to Break Away from Traditional Success Paths

The legal profession loves to talk about price tags:

• The cost of law school
• The value of billable hours
• The ROI of making partner

But there's one cost they never put in the brochures: The Courage Tax.

It's what you pay when you decide that the traditional path isn't working for you anymore. When you look at the corner office and realize—I don't actually want that.

And for women in law? This tax runs especially high.

What Exactly Is the Courage Tax?

The Courage Tax is everything you invest—emotionally, financially, and professionally—when you choose to redefine success on your own terms.

It's the raised eyebrows when you:

• Leave Big Law to start your own practice
• Reduce your hours to prioritize family
• Pivot to an entirely different area of law
• Say "no" to a path that's killing your spirit

It's the price of admission to a life that actually feels like yours.

Why Women Pay a Higher Rate

When I walked away from the law, the whispers started immediately.

"She couldn't handle the pressure." "Another woman who couldn't commit to the partner track." "She had so much potential."

What they didn't say? That I was building something I believed in. That my wellbeing mattered as much as my output.

The Courage Tax for women often comes with a gender surcharge:

• We're questioned more harshly about our choices
• We face assumptions about our commitment
• We battle the nagging feeling that we're "letting down the team"
• We worry about reinforcing stereotypes about women "not being tough enough"

What's In Your Tax Bill?

The Courage Tax doesn't arrive in a neat envelope. It shows up in a thousand small moments:

🔸 Financial Investments

• Potential income sacrificed during transition
• Startup costs for a new practice
• Investment in retraining or new certifications
• Safety nets and runway funds

🔸 Relationship Capital

• Explaining your choices to confused colleagues
• Risking professional relationships tied to old structures
• Finding new networks that align with your vision
• Rebuilding credibility in new spaces

🔸 Emotional Labor

• Managing doubt (yours and everyone else's)
• Navigating identity shifts
• Building resilience against setbacks
• Finding confidence without institutional backing

Is It Worth Paying?

When I look back at my own Courage Tax—walking away from the path I had spent years working toward—I sometimes still feel the weight of that decision.

But here's what I've learned from both my journey and the journeys of hundreds of women lawyers I've worked with:

The return on investment is almost always worth it.

Not because it was easy. But because on the other side was something priceless: a career that actually reflected who we are.

How to Make the Investment Worth It

If you're considering paying your own Courage Tax, here's how to ensure the highest return:

1. Calculate Your TRUE Costs Don't just focus on immediate financial impacts. Consider long-term wellbeing, purpose, and potential. What's the cost of staying where you are?

2. Build a Support Network BEFORE You Need It Find your people—other women who've made bold moves. They'll be your emotional tax shelter when things get tough.

3. Create Transition Bridges Rarely does change happen overnight. Can you build a bridge between where you are and where you want to be? Part-time arrangements, side projects, and strategic moves can reduce the immediate tax burden.

4. Remember Why You're Paying Keep your "why" front and center. The tax feels heavier when you lose sight of what's on the other side.

The Return on Investment

I've watched women transform their legal careers in ways that seemed impossible:

• The Big Law attorney who now runs a thriving boutique practice focused on causes she believes in
• The burnt-out Big Law attorney who took back her career and transitioned to a position that actually aligned with her values and priorities. 
• The firm owner that started working smarter not harder, reduced her hours and kept her income. 

Their Courage Tax? Paid in full. Their returns? Immeasurable.

Your Tax Bill Is Waiting

Here's what I know for sure: There's no avoiding the Courage Tax. You either pay it upfront by making bold choices aligned with your values, or you pay it in installments—through years of quiet resignation, wondering "what if?"

But here's the thing about taxes: they fund something bigger. Your Courage Tax doesn't just change your life—it helps build a new landscape for women in law.

Every woman who pays her Courage Tax makes it a little easier for the next one. Every new path carved makes the forest a little less dense for those who follow.

💬 I want to know: What's one small Courage Tax you've paid in your career that turned out to be worth every penny?

Here's to investments that matter,

xo, Erin