Rushing a divorce can cost you money, leverage, and peace—especially if you’re dating, listening to family “advice,” or skipping the right experts. In this episode, Morgan Stogsdill and Andrea Rappaport break down the most common divorce regrets and the smart, strategic moves to avoid them.

In this episode of How Not to Suck at Divorce, Morgan and Andrea unpack the most common divorce regrets they see over and over again: the ones that quietly cost you money, complicate custody, drag out the process, and make you look back thinking… why did I do that?

Get real divorce advice your lawyer may be too polite to share. We break down unpopular divorce opinions and practical divorce tips that can save you thousands of dollars in legal fees, reduce stress, and help you avoid costly mistakes. How Not to Suck at Divorce is the divorce podcast for people who want clarity, strategy, and support

From rushing because you’ve moved on romantically, to letting your dad become your “legal strategist,” to skipping experts like OurFamilyWizard because you’re trying to save money—this is your highlight reel of what not to do (and what to do instead).

And yes… Billy Bob Thornton and Angelina Jolie make an appearance. Because apparently six marriages is one way to earn a PhD in divorce.

In this episode, we cover:

The #1 regret: rushing your divorce and leaving money on the table
Why “I want to be divorced by March” can backfire fast
How outdated financials and an old balance sheet can cost you thousands
Why your new partner should not be part of the divorce “mischigas”
The danger of letting family and friends influence legal decisions
How well-meaning parents can accidentally run up your legal bill
When outside experts (forensic accountants, co-parenting tools, therapists) actually save you money
Why trying to “cheap out” can lead to a future court nightmare
The difference between fighting for what matters vs. fighting over balsamic vinegar
How to decide what’s worth it (and what’s just ego, fear, or control)

Key Takeaways (Quick & Skimmable)

1) Don’t rush the process and leave money on the table

When you’re desperate to be done, you cut corners. That’s how people sign agreements with missing details, outdated account values, or unclear parenting language—then regret it later.

Do this instead: Ask your attorney if your timeline is realistic, and if it is—map the steps from A to Z.

2) Don’t bring your new relationship into your divorce chaos

Your new person may mean well, but they are not your lawyer—and emotionally, it can start poisoning the relationship fast.

Do this instead: Process the divorce with your therapist, your support system, and your attorney—not your new partner.

3) Don’t let non-lawyers steer legal decisions

Even smart, loving parents can unintentionally derail the strategy—especially when they aren’t in the day-to-day “trenches” of your case.

Do this instead: If a family member must join a call, keep it controlled: you’re present, they stay muted, and they ask questions at the end.

4) Don’t skip tools and experts just to “save money”

Skipping the right expert can create a bigger bill later—especially in co-parenting disputes, business valuations, and post-decree enforcement.

Do this instead: If your attorney recommends something like OurFamilyWizard or a valuation expert, ask why—and seriously consider it.

5) Don’t drag out your divorce fighting over small stuff

There’s a difference between protecting what matters and spending thousands to win a couch, condiment collection, or “principle.”

Do this instead: Ask your attorney: Is this worth the cost to fight over?

Action Steps (What to do today)

Write down your goals: “What do I NEED vs. what do I WANT?”
Ask your lawyer directly: “Am I rushing—and what could that cost me?”
Update your financials before signing anything (especially account balances).
Keep your support team clean: attorney + therapist + trusted friend (not your new partner).
Stop paying legal fees for emotional processing—save that for therapy.

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

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/notsuck

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

Mentioned in this episode:

Natural Cyles

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Natural Cycles