The first thing most people do when they’re facing a divorce is compare. They talk to friends, read articles online, and try to map their situation onto someone else’s experience. It almost never fits. And that gap between what they expected and what they’re actually facing — in either direction — is where things go wrong.
After more than two decades handling divorces in New York, I’ve learned that the single most expensive assumption a person can make is thinking they already know how complicated their case is going to be.
The assumption almost everyone makes
People tend to walk into my office in one of two states. Either they’re convinced their divorce is going to be a nightmare — emotionally, financially, logistically — and they’re bracing for the worst. Or they’re certain it’s going to be straightforward, that they and their spouse have basically agreed on everything, and they just need someone to write it up.
Both groups are frequently wrong.
Not because they’re not intelligent people. They are. But because divorce has a way of revealing complexity that wasn’t visible from the outside — and occasionally dissolving complexity that felt overwhelming. The difference between those two outcomes often comes down to whether someone is looking at the full picture clearly, and early.
When simple becomes complicated
I worked with a woman whose husband was a banker. She was sharp, informed, and had been closely involved in managing their finances throughout the marriage. She came to me feeling confident she understood what they had and what a fair division would look like.
During discovery, we found that a significant portion of her husband’s compensation was structured as restricted stock units — RSUs. She hadn’t fully understood how those units needed to be valued, what was vested versus unvested, or how the timing of the divorce would affect what she was entitled to receive. What had looked like a clear financial picture turned out to have an entire hidden dimension.
We worked through it. We brought in the right expertise and rebuilt her understanding of the full asset picture from the ground up. She came out of the process far better than she would have if we’d accepted the simple version of the story.
But here’s the lesson: it wasn’t her fault for not knowing. RSUs are genuinely complex financial instruments, and understanding how they’re treated in a divorce requires a very specific kind of knowledge. The danger wasn’t her ignorance — it was the assumption that there was nothing left to learn.
When complicated becomes manageable
The opposite happens just as often, and it’s one of the more rewarding things I get to do in this work.
Someone sits across from me who is convinced they’re trapped. Maybe their spouse controlled all the finances. Maybe they haven’t worked in years. Maybe they feel like they have no leverage, no resources, and no path forward. The situation feels impossible.
What they don’t yet see is that the process of divorce itself is designed to surface information and restore balance. Assets accumulated during the marriage belong to both parties, regardless of whose name they’re in or who managed them. Support structures exist precisely for situations where one spouse is financially dependent. Options that feel unavailable at the start of the process — refinancing, asset swaps, structured settlements — often open up as the full picture comes into view.
What looked like a locked door frequently has a key. It just takes someone who knows where to look.
What determines complexity
It’s not the size of the assets. It’s not even the level of conflict, though that certainly matters. In my experience, what truly determines how complex a divorce becomes is whether someone can see the whole picture, not just the part that’s visible right now— going beyond the obvious issues to identify the ones hiding beneath them.
A short marriage can have surprising financial entanglements. A high-asset divorce can sometimes resolve more quickly than expected when both parties are motivated and well-advised. A case that looks contentious on the surface can shift when someone identifies what each party needs, as opposed to what they think they want.
Complexity, in other words, is rarely fixed. It’s a moving target. And the earlier you get a clear-eyed read on where yours stands, the better positioned you are to navigate it.
The one thing to do before you assume anything
Talk to someone who has seen enough cases to know the difference.
Not to be told what to do, and not to be frightened into action. But to get an honest, informed read on what you’re facing — and what your real options are. Because whether your divorce turns out to be simpler than you feared or more layered than you imagined, the worst place to start is with an assumption.
