Episode 188: Top Divorce Regrets
The Biggest Divorce Regrets (and What to Do Instead)
If you’re in the middle of a divorce, there’s a good chance you’ve had this thought at least once:
“I just want this to be over.”
We get it. Divorce is exhausting. It’s emotional whiplash. It’s paperwork. It’s custody logistics. It’s spending money you never wanted to spend. And if you’ve already moved on romantically? The urge to hit “fast forward” becomes feral.
But here’s the problem: rushing is how people make expensive mistakes—the kind you don’t fully understand until months (or years) later when you’re stuck dealing with a post-decree mess you never saw coming.
In this episode of How Not to Suck at Divorce, Morgan and I break down the most common divorce regrets we see over and over again—plus exactly what to do instead, so you don’t look back and think, “Wait… why did I sign that?”
And yes, Billy Bob Thornton makes an appearance. Because if you’ve been married six times, you’ve basically earned an honorary doctorate in divorce.
Divorce Regret #1: Rushing the Process (and Leaving Money on the Table)
One of the biggest mistakes people make is putting an arbitrary deadline on divorce, like:
“I want to be divorced by March.”
Morgan’s response is basically: “Cool. We all want things.”
When you rush, you cut corners. That’s how people:
settle with outdated financial numbers
miss important details in parenting agreements
sign before they fully understand what they’re giving up
fail to update account balances and end up leaving money on the table
What to do instead:
Ask your attorney:
Is my timeline realistic?
If yes: What’s the plan to get there?
If no: What’s a realistic timeline so I don’t screw myself financially?
Divorce Regret #2: Letting Your New Partner (or Your Parents) Get in the Trenches
Listen: we love love. We want you happy. We want you dating again when you’re ready.
But your new partner does not belong inside your divorce chaos.
Andrea’s take (from experience):
Don’t bring your new partner into the mishigas. They don’t want to go through it, and legally it can create problems—especially when they start trying to solve a situation they don’t understand.
And it’s not just new partners.
Sometimes it’s your mom, your dad, your sister, your best friend, your neighbor with “opinions,” or your cousin who watched Suits once and now thinks he’s a legal strategist.
What to do instead:
Vent to your therapist and your support system
Make legal decisions with your attorney
If a family member must be involved, keep it tight:
they join the call muted
questions at the end only
no side calls with your lawyer that you aren’t on (because hello billable hours)
Divorce Regret #3: Trying to “Save Money” by Skipping Experts
We see this constantly:
People get terrified of how much divorce costs, so they decide to cut expenses wherever they can. The issue is… some of those “expenses” are actually protective tools.
Morgan tells a story about a client who didn’t want to pay for OurFamilyWizard—a court-respected co-parenting app that helps organize communication and receipts.
Fast forward: years later, that client is in court dealing with a claim that he never paid thousands of dollars in expenses… and now he has to sort through years of emails to prove it.
He tried to save money.
And it cost him way more.
What to do instead:
If your attorney recommends a tool or expert (like):
OurFamilyWizard
a forensic accountant
a business valuation expert
a therapist
Ask why… and don’t automatically assume it’s “extra.” Sometimes it’s the thing that saves you from an expensive disaster later.
Divorce Regret #4: Waiting Too Long to File Without a Plan
This one is HUGE.
A lot of people don’t file because they’re scared. They’re worried about the kids. They’re hoping things improve. They’re mentally frozen.
But if you already know divorce is likely and you’re just “waiting”… you’re exhausting yourself while the situation stays the same.
By the time you finally file, you’re already depleted—which makes the entire process harder.
What to do instead:
You don’t have to file today, but you should sit down with an attorney and ask:
Is there a strategic reason to wait?
If yes: what’s the plan and what are we waiting for?
If no: what’s the benefit of staying in hell longer?
Waiting can be smart—if there’s a strategy (bonus payout, major life event, etc.). Waiting “just because” is usually where regret lives.
Divorce Regret #5: Dragging It Out Fighting Over the Small Stuff
There’s a difference between:
protecting what matters
andfighting because you’re scared, angry, or trying to regain control.
Morgan calls this the “balsamic vinegar problem.” People will spend thousands in legal fees arguing over things they could replace for way less… just to feel like they “won.”
What to do instead:
Before you fight over something, ask:
Do I need this?
Do I want this?
How much is it worth to me in legal fees?
Would I rather be done and buy a new couch?
Sometimes the smartest move is cutting bait—so you can move on with your life.
Your “What To Do Instead” Checklist
If you take nothing else from this episode, take this:
✅ Set realistic expectations with your attorney
✅ Don’t rush the settlement just to be done
✅ Keep your divorce team clean (lawyer + therapist + trusted support)
✅ Use the right tools (especially for co-parenting + finances)
✅ Stop fighting over the balsamic
Divorce is a marathon, not a sprint. Some days it’s hour-by-hour. But you’re not alone.
And on your worst days…
You’ve got this. And we’ve got you.
Want to go deeper?
If you’re stuck in one of these regret zones right now—rushing, waiting, fighting, spiraling, or letting too many voices influence you—DM us or join our private community. We’ll help you get clear on what’s normal, what’s strategic, and what’s just making your divorce more expensive than it needs to be.