The Gray Divorce Podcast: Episode 103 Gray Divorce Survivor Attorney David Fein Talks Mediation

David Fein didn't begin his career intending to become a divorce mediator.

His professional background involved bringing together diverse groups in the energy industry and finding solutions that allowed people with competing interests to reach workable agreements. After experiencing the power of mediation during his own gray divorce, David recognized how naturally those same skills translated into helping divorcing couples.

Today, he uses that experience to help couples identify their priorities, understand their options, and create agreements that allow both people to move forward with their lives.

From Building Coalitions to Mediating Divorce

For decades, David's work required bringing together groups that didn't necessarily agree—organized labor, environmental organizations, energy companies, and others—and finding areas where everyone could gain something.

Divorce mediation presents a similar challenge.

Two people may enter the process in conflict, with very different priorities and interests. The mediator's job isn't to decide who's right or impose a solution.

It's to help both people find enough common ground to create a workable agreement.

David's background taught him an important lesson that now shapes his mediation practice:

Successful negotiation doesn't require everyone to want the same thing.

It requires understanding what matters to each person and finding a path forward.

David's Own Experience With Gray Divorce

David's introduction to mediation wasn't professional—it was personal.

After approximately 18 months of separation, his former spouse suggested mediation. Both were attorneys, but neither wanted to spend significant money on lengthy and uncertain litigation.

They decided to try mediation.

The process began around August or September and was largely completed by November, with the legal completion delayed until the following year for tax reasons.

That experience showed David firsthand that divorce could be approached differently and eventually inspired him to become certified in divorce mediation.

Mediation Doesn't Have to Happen in One Marathon Session

Many people picture mediation as an exhausting five- to eight-hour day with spouses, attorneys, and a mediator trying to resolve everything at once.

David takes a different approach.

His sessions typically last about 90 minutes, allowing couples to address issues in manageable pieces over several weeks or months.

Rather than overwhelming clients, he wants them to have enough time to:

• Understand the issue being discussed
• Consider their options
• Process information
• Ask questions
• Prepare for the next conversation

When younger children are involved, David often begins with parenting matters because they're important and can sometimes create early agreements that build momentum for the rest of the mediation.

Preparing for Mediation Without Becoming Overwhelmed

David doesn't believe clients should arrive at mediation buried under mountains of homework.

Instead, he gives them enough information to understand what will be discussed at the next session.

That might include:

• A preview of upcoming topics
• Sample parenting schedules
• Relevant reference materials
• Issues they should begin considering
• Opportunities to discuss certain matters with one another beforehand when appropriate

The objective isn't to have everything figured out before mediation begins.

It's to arrive informed enough to participate thoughtfully in the conversation.

Andrew and David also discuss the growing role of pre-mediation divorce coaches, who can help clients prepare emotionally and practically before negotiations begin.

What Do You Need to Feel Secure After Divorce?

Gray divorce creates a different set of priorities because people may have far less time to recover financially.

When adult children mean parenting schedules are no longer the obvious starting point, David begins by asking clients to identify their:

Needs, wants, and desires.

What do you need when you walk out of mediation to feel comfortable and secure about your future?

For one spouse, it may be remaining in the marital home.

For another, it could be receiving enough support to maintain financial stability.

Someone approaching retirement may be particularly concerned about protecting retirement assets because there simply isn't enough time left in their career to rebuild them.

Understanding those priorities helps determine where the mediation should begin and may reveal areas where the spouses already agree.

The Mediator Is a Guide, Not the Decision-Maker

Andrew and David share a similar philosophy about mediation:

The professional is there to facilitate, educate, and guide—not dictate the outcome.

David makes it clear to clients that, as a mediator, he has no power to force either spouse to agree to anything.

Instead, he asks questions, helps couples explore alternatives, and provides examples of how other people have addressed similar issues when clients become stuck.

That ownership matters.

David believes an agreement is more likely to be sustainable and durable when the couple reaches it themselves rather than having a solution imposed upon them.

Financial Knowledge Can Create a Power Imbalance

One of the most important issues in gray divorce mediation is the financial knowledge gap that may exist between spouses.

In many marriages, one person has historically handled most of the financial decisions.

That can create an inherent imbalance when divorce begins.

David believes mediators must recognize that imbalance and make sure the less financially experienced spouse has enough education and access to trusted professionals to participate meaningfully in negotiations.

The goal isn't to turn someone into a financial expert overnight.

It's to make sure they understand enough to make informed decisions about the rest of their life.

Build the Post-Divorce Budget Before Making the Deal

One advantage of mediation is the ability to slow down and test whether a proposed settlement will actually work.

Instead of simply dividing assets on paper, David can help someone look at:

• Income
• Alimony or maintenance
• Child support, when applicable
• Housing costs
• Monthly expenses
• Available financial cushion

Then comes the important question:

Will you actually be okay?

If the numbers show someone will be financially underwater, that information may influence how other assets are divided.

Creating a realistic budget also helps reduce one of the biggest emotional drivers in gray divorce:

Fear of the unknown.

Build the Right Divorce Team

Mediation doesn't mean doing everything yourself.

In fact, David strongly supports bringing in specialized professionals when needed.

Depending on the circumstances, that team might include:

• Consulting attorneys
• Certified Divorce Financial Analysts (CDFAs)
• Certified Divorce Lending Professionals (CDLPs)
• Divorce coaches
• Real estate professionals
• Appraisers
• Other financial experts

David also encourages clients to have legal counsel available even when attorneys aren't participating directly in every mediation session.

In Illinois, for example, mediators cannot draft the marital settlement agreement—even when the mediator is also an attorney. State laws and ethics rules vary, making it important to understand the requirements in your own jurisdiction.

Don't Confuse Mediation With a DIY Divorce

Andrew emphasizes an important distinction:

Choosing mediation doesn't mean eliminating attorneys altogether.

Eventually, a divorce decree becomes a legal document with potentially decades-long consequences.

A mistake today could mean reopening or relitigating an issue three, four, or five years later.

A consulting attorney may be able to provide targeted legal advice and review documents without necessarily requiring the much larger financial commitment associated with full-scale litigation.

When David serves as mediator, he is a neutral third party. Even though he's an attorney, he cannot provide legal advice to either spouse while serving in that role.

The Deceptiveness of Spreadsheets

One of the most important financial lessons in the episode is deceptively simple:

Every dollar isn't equal in divorce.

Imagine a spreadsheet showing:

• $1 million marital home
• $1 million pre-tax IRA

On paper, they both say $1 million.

But economically, they're not the same asset.

The IRA may eventually be subject to income taxes when distributions are taken. The house has its own costs, tax considerations, liquidity issues, and emotional significance.

A settlement can appear perfectly equal on a spreadsheet while producing very different financial outcomes for the two spouses.

Understanding the type of asset matters just as much as understanding its stated value.

Businesses Make the Financial Picture Even More Complicated

Business interests can create another layer of complexity.

A business may appear to be worth $1 million on a spreadsheet—but valuation isn't always straightforward.

Experts may disagree.

Personal goodwill may be involved.

One spouse may have contributed differently than the other.

And selling the business may dramatically change its actual economic value.

David explains that mediation can provide more room for creative solutions when complicated assets are involved. Traditional litigation may leave a court with fewer practical options, including potentially forcing a sale or leaving former spouses as joint business owners.

Neither may be the outcome the couple actually wants.

Key Takeaways

• Mediation can provide a more flexible and collaborative alternative to traditional divorce litigation.
• Gray divorce requires particular attention to retirement security and long-term financial sustainability.
• Mediation doesn't have to be completed during one exhausting all-day session.
• Identifying each spouse's needs, wants, desires, and goals can help establish priorities early.
• A mediator facilitates agreement but doesn't make decisions for the couple.
• Financial knowledge gaps between spouses need to be recognized and addressed.
• Building a realistic post-divorce budget can reduce fear and improve settlement decisions.
• A strong mediation team may include attorneys, CDFAs, coaches, lending professionals, appraisers, and real estate experts.
• Assets with identical values on a spreadsheet may have dramatically different real-world values.
• Mediation isn't right for every divorce—but couples should understand their options before choosing a process.

Final Thoughts

David's closing advice is an important reminder for anyone beginning the divorce process:

Don't assume there's only one way to get divorced.

Calling an attorney may be an appropriate first step, but it doesn't necessarily need to be the last step in deciding which process is right for you.

Research mediation.

Talk to professionals who work in different areas of divorce.

Understand the advantages and limitations of each approach.

And don't rely solely on internet searches or AI to make those decisions.

Taking time at the beginning to understand your options may save money, reduce conflict, and help create a divorce agreement that better supports both people as they begin the next chapter of their lives.

Resources

David Fein 

• Attorney & Certified Divorce Mediator 
• Fein Legal Solutions 
• Website: feinlegalsolutions.com 
• Phone: 312-446-2882 
• Based in Illinois

Andrew Hatherley 

• The Gray Divorce Podcast 
• Transcend Retirement

Professionals Discussed in This Episode

• Divorce mediators
• Consulting family law attorneys
• Certified Divorce Financial Analysts (CDFAs)
• Certified Divorce Lending Professionals (CDLPs)
• Divorce coaches
• Real estate professionals and appraisers