How Not To Suck At Divorce 178. How Asking ‘WHY’ Can Change Your Divorce
Making better decisions by understanding what really matters.
If you’re in the middle of a divorce and constantly asking yourself “WHY is this happening?”, this episode is about to save you money, misery, and a whole lot of emotional tailspinning.
This week, Andrea and Morgan dive deep into the question that can either move your divorce forward—or completely derail you: WHY.
When is asking why strategic?
And when is it a waste of attorney fees (or your sanity)?
To help break it all down, we’re joined by Cary J. Mogerman, one of the most respected divorce attorneys in Missouri. Cary brings decades of experience, a wise-professor vibe, and a no-nonsense approach to helping clients understand the process clearly, calmly, and strategically.
Cary J. Mogerman is one of the most highly regarded divorce lawyers in Missouri and wellknown to other top family law attorneys throughout the United States. He is a Fellow of the American Academy of Matrimonial Lawyers and in 2022, served as President of the national organization. He is a Diplomate of the American College of Family Trial Lawyers, an invitation-only assemblage limited to 100 members throughout the United States; Cary is a member of its executive committee. He is a Fellow of the International Academy of Family Lawyers.
https://carmodymacdonald.com/people/cary-j-mogerman/
In this conversation, you’ll learn:
- Why “Why is this happening to me?” is a therapist question—not a lawyer question
- How to ask WHY in a way that strengthens your strategy, saves money, and reveals leverage
- Why understanding your spouse’s emotional triggers can completely shift mediation
- The one communication mistake clients make that drives lawyers insane
- When your lawyer should break things down in plain language
- Why slowing down your responses (yes, YOU) will prevent disaster
- How to stop burning money on the wrong kind of questions
- Why the legal process feels slow, confusing, and unfair—and what to do with that
- How to advocate for yourself without apologizing
PLUS: Andrea reveals a HUGE co-parenting milestone (Shabbat dinner with the ex… yes, seriously), and Morgan talks through why listeners were so triggered by last week’s episode—and what that means for your own healing.
This is the episode you NEED if you’re negotiating, mediating, litigating, co-parenting, or just trying to get through the day without rage-texting your ex or panic-emailing your lawyer.
Key Takeaways
1. Not All “Why” Questions Are Helpful
“Why is this happening?”
“Why is he acting like this?”
“Why is she being crazy?”
These are human questions—but not legal ones.
They belong in therapy, not in your billable hours.
2. Strategic Why’s Are POWERFUL
Why are we filing this motion?
Why is this our mediation plan?
Why is my ex reacting this strongly to ONE issue?
These help your attorney build a smarter, more effective case.
3. Your Lawyer Should Explain Everything in Plain Language
Cary breaks down why attorneys NEED to simplify their communication—and why you should never feel embarrassed asking:
“Can you explain that in normal-person English?”
4. Your Spouse’s Triggers = Your Strategy
You know your spouse better than anyone.
Your insights help your attorney negotiate smarter and faster.
5. Don’t Make Split-Second Decisions During Emotional Surges
You’re not being chased by a bear.
Slow down. Breathe. Don’t respond immediately.
You can literally save thousands of dollars by pausing.
6. Your Lawyer Isn’t Your Therapist
If you use your attorney to process grief, fear, or trauma—you’ll pay for it.
A therapist handles feelings.
A lawyer handles logistics and strategy.
7. Mediation Success Depends on the Why
Understanding WHY your ex digs their heels in reveals:
- leverage
- pressure points
- opportunities for compromise
8. Don’t Waste Your Money Asking Why the Law Is Unfair
It is unfair.
But your lawyer can’t change it.
Save your dollars for actual strategy.
Timestamps
00:00 — Cary opens up about the problem with legal language
00:09 — Morgan: never feel bad asking “why”
00:19 — How WHY can transform mediation
00:46 — Show intro
01:22 — Connecting instead of isolating during divorce
01:37 — Truly Engaging partnership
02:19 — Holiday-card humor + promo code
02:26 — Being proactive vs reactive in divorce
02:44 — Why communication apps matter (Our Family Wizard plug)
03:19 — Andrea drops a HUGE co-parenting surprise
05:02 — The Shabbat dinner miracle (yes, really)
06:33 — Listener backlash from last week
07:40 — Nervous system regulation in co-parenting
08:53 — Introducing guest attorney Cary Mogerman
10:16 — Why blindsided spouses struggle with “why”
12:04 — When WHY keeps clients stuck
13:26 — The role of therapy vs legal strategy
14:44 — The cost of asking the wrong WHY
15:30 — When WHY is your best tool
17:02 — How WHY reveals leverage in mediation
17:54 — Plain language: the communication clients deserve
19:48 — Don't feel bad asking your lawyer to explain
21:22 — Email vs call: when & how to communicate
22:18 — How to prep for a paid call with your attorney
23:41 — Using WHY strategically in litigation & mediation
24:33 — When your WHY belongs in therapy
25:16 — Why divorcing people need communication guides
26:26 — Knowing your spouse’s triggers = negotiation power
27:25 — Why lawyers need your full story
28:41 — Real-life example: using money triggers in negotiation
31:34 — Why you don’t need to make immediate decisions
32:21 — Emotional reactivity and fight-or-flight
33:52 — Why your brain panics during divorce
35:14 — The WHY questions that waste money
35:45 — Why fairness doesn’t matter in court
37:36 — Action steps: when to ask WHY & when not to
38:47 — Cary’s closing wisdom
39:39 — How to know when to get curious vs when to let go
40:59 — Resources to help you save money & stress
41:28 — Why divorce is a marathon, not a sprint
42:02 — Final reassurance: you’ve got this (and we’ve got you)
Our Divorce Crash Course was designed to hold your hand through the process and help you avoid major and expensive mistakes. Learn more here: https://www.hownottosuckatdivorce.com/divorce-crash-course
We are truly engaged with Truly Engaging cards. It's THE BEST way to remain connected with your community. Use code: NOTSUCKTE to get 10% off your order and ask to have Alisiah help you!! www.trulyengaging.com
Join the private communities!
The How Not to Suck at Divorce Community
The How Not to Suck at Life AFTER DIVORCE Community
Our Family Wizard is another fantasitc resource for those who need help navigating the "fun" world of coparenting. Head to this landing page to see how we work closely with them to support our listeners! http://www.ourfamilywizard.com/notsuck20
Friends, slide into our dms, we love love love hearing from you. We are always here to listen and help in any way we can. You've got this and we've got you.
Instagram: @hownotosuckatdivorce
Follow Andrea: @theandrearappaport
Follow Morgan: @divorceattorneychicago