Diana Telfer

After helping hundreds of individuals and couples navigate divorce, I have become convinced of one thing: very few conflicts are actually about money.

They are about what money means.

Over the years, I have sat across the table from couples arguing about retirement accounts, businesses, homes, credit cards, inheritances, and monthly budgets. On the surface, the disagreements appear to be about dollars and cents. But when we slow the conversation down, something deeper almost always emerges.

One spouse is seeking security, the other values freedom.

One sees saving as responsible, the other sees spending as enjoying the life they worked hard to build.

Neither person is necessarily wrong; they have different “money personalities.”

We all have a money story

Long before we marry, we begin developing beliefs about money. Maybe your parents lived paycheck to paycheck, making you determined to save every dollar.

Perhaps you watched a parent lose a business during a recession and learned that financial security should never be taken for granted.

Or maybe your family celebrated life’s milestones through travel, experiences, and generosity, teaching you that money is meant to be enjoyed.

Those early experiences quietly shape our financial habits for decades. Most of us do not even realize we have a money personality until someone close to us approaches money very differently.

I’ve seen this more times than I can count

One of the advantages of practicing collaborative divorce and mediation is that I have the opportunity to hear not only what people are arguing about, but why. I remember early in my career thinking, “If I can just explain the math, this issue will be resolved.”

Ha, let me tell you – it rarely worked. The numbers were rarely the real issue.

Once we started talking about what each person feared, valued, or hoped for, entirely different conversations began to unfold.

A disagreement over selling the family home might actually be about stability for the children.

An argument about retirement accounts might really be about fear of growing older alone.

A dispute over a closely held business may reflect years of sacrifice, identity, and pride rather than simply its appraised value.

Those conversations are far more meaningful—and far more productive—than debating numbers alone.

Common money personalities

While everyone is unique, I often see certain financial tendencies emerge.

The Security Seeker

Security Seekers find comfort in savings, predictable income, and financial stability. During divorce, they may worry about whether there will be “enough,” even when the numbers suggest they will be financially secure.

The Planner

Planners like budgets, spreadsheets, and well-thought-out decisions. Uncertainty can be particularly stressful, making divorce feel overwhelming because so many future decisions remain unknown.

The Entrepreneur

Entrepreneurs often view money as a tool rather than something to preserve. They are comfortable with calculated risk, reinvesting in their business, and focusing on long-term growth instead of short-term security.

This perspective can be difficult for a spouse who places a higher value on certainty.

The Caregiver

Caregivers frequently prioritize everyone else’s needs before their own. During divorce, they may agree to financial arrangements that are less favorable simply to reduce conflict or protect their children.

The Avoider

Some people dislike dealing with financial matters altogether. They may have allowed their spouse to manage household finances throughout the marriage or simply postponed difficult financial conversations.

Unfortunately, avoidance during divorce often increases stress and can lead to costly mistakes.

None of these personalities are “wrong”

One of the most important things I tell clients is this:

Your money personality is not a character flaw.

Every personality has strengths AND blind spots.

Problems arise when we assume our approach is the only reasonable one. When couples begin to understand that they are bringing different financial values into the conversation—not necessarily bad intentions—the tone often changes. Curiosity begins to replace blame.

Divorce doesn’t create these differences

Divorce has a way of shining a bright light on financial habits that may have existed throughout the marriage.

Sometimes couples have successfully balanced one another for years. Sometimes they avoided talking about money altogether. When the marriage ends, however, every financial decision suddenly feels more significant.

That is why understanding your own money personality can be one of the most valuable investments you make during the divorce process.

A few questions for you to consider

As you think about your own relationship with money, ask yourself:

• What messages about money did I learn growing up?
• Does financial security bring me peace, or do I value flexibility and opportunity?
• What financial decisions cause me the greatest anxiety?
• What am I truly trying to protect?
• Am I reacting to today’s circumstances, or to experiences from years ago?

There are no right or wrong answers. The goal is simply greater self-awareness.

Some final thoughts

One of the reasons I enjoy practicing collaborative divorce and mediation is that they create space for these deeper conversations. Instead of focusing solely on dividing assets, we have the opportunity to understand the values, fears, and priorities driving each person’s decisions.

Money is important.

But understanding the story behind the money is often what helps people move forward with greater confidence, clarity, and peace.

Next in this month’s series

Next week, I’ll explore why many highly successful women—including business owners, physicians, executives, and other professionals—often find financial decisions during divorce surprisingly difficult, even though they confidently make high-stakes decisions every day in their careers.

If this article resonated with you, follow along as we continue exploring the many ways our relationship with money influences divorce decisions—and how greater awareness can lead to better outcomes for you and your family.” That consistency helps build anticipation for the next installment.

With care,

Diana

Holidays can feel especially stressful after divorce, when extended family members still hold ideas about how things “should” look. Their intentions are often loving, but their expectations may no longer fit your family’s reality. The good news: clear boundaries and thoughtful communication can help the season feel calmer, more intentional, and even more meaningful.

Why Expectations feel so heavy

Holiday traditions are deeply rooted in memory and identity. After divorce, extended family members may want to preserve what feels familiar, which can create pressure around:

• Longstanding gatherings that no longer fit
• Competing invitations
• Guilt or disappointment when plans change
• Difficulty accepting new roles or routines

These reactions are normal, but you are not responsible for recreating a past that no longer exists.

Giving yourself Permission to set Boundaries

Divorce changes logistics and emotional capacity. Boundaries help protect everyone’s well-being, including your children’s.

Healthy boundaries may include:

• Declining events that complicate schedules
• Limiting how many gatherings your children attend
• Asking relatives to celebrate on a different day
• Keeping parts of the holiday simple or private

You do not need to please everyone. You need to care for your family.

Communicating with Compassion

Clear, kind communication helps extended family understand why things are shifting. Helpful phrases include:

• “We are adjusting to new routines this year and appreciate your flexibility.”
• “We are keeping things simple for the kids.”
• “That tradition meant a lot, but it may not work the same way now.”

Share what your children truly need without over-explaining or apologizing.

Helping Family understand your Children’s Needs

Kids do best with:

• Predictable routines
• Low-pressure celebrations
• Time to relax rather than rushing
• Emotional breathing room

Quality of connection matters more than sticking to a specific tradition or date.

Creating new Ways to connect

Change also allows creativity. Encourage extended family to explore traditions that better fit your new rhythm:

• A pre-holiday breakfast
• A New Year’s cocoa night
• A simple gift-opening ritual on another day
• A calm January outing

Sometimes spreading out celebrations makes them more enjoyable.

Releasing Guilt and embracing what works

Guilt is common, but it is not a useful guide. You can prioritize your children and your well-being, even if others need time to adjust.

Remember:

• You cannot recreate the past.
• Extended family will adapt.
• Calm, connected, authentic holidays matter most.

Moving forward TOGETHER

Extended families are resilient. With boundaries and open-hearted communication, relationships can strengthen rather than strain.

Holidays after divorce may look different, but they can still be rich with warmth and connection, because they’re built around what truly works for your family now.

Happy Holidays to you and yours!

With deep care,

Diana

The holidays often arrive carrying a bundle of expectations. Some joyful, some heavy, and many shaped by the past. After divorce, families may find that old traditions no longer fit the way they once did. Kids grow, family systems shift, and what once felt warm can suddenly feel complicated or even painful.

Yet this moment of change also holds an extraordinary invitation:

the chance to create new tradition

Traditions, that feel authentic, joyful, and aligned with who your family is becoming.

When holding onto old Traditions becomes a Struggle

It is completely understandable that some parents feel a deep pull to preserve “how we’ve always done it.” Longstanding holiday traditions can carry meaning, nostalgia, and a sense of identity. But after divorce, trying to maintain historic traditions exactly as they were may not be realistic (or healthy!) for anyone involved.

Schedules shift, families blend, logistics change, and the emotional landscape is different. What was once simple may now create tension, conflict, or disappointment. Parents can sometimes become entrenched in positions, insisting on honoring the past to avoid the grief of change. But rigidity often makes the holidays harder, not easier.

And here is the hopeful truth: Children are far more resilient than we often realize.

They do not require perfect replication of past traditions to feel secure or joyful. In fact, many kids appreciate the chance to create new rituals that reflect their current lives and relationships. New traditions can feel exciting, empowering, and freeing.

Letting go of the insistence on “how it used to be” opens space for “what could be” and that shift can bring genuine relief and connection.

Why reinventing Traditions matters

Traditions do more than mark holidays; they help shape a family’s identity. After divorce, children and parents alike may feel unmoored from what once felt familiar. Building new rituals offers stability and belonging. These traditions do not have to be grand; they simply need to feel like you.

When families consciously choose how they celebrate rather than defaulting to “what we’ve always done” they send a powerful message:

We are still a family.

We still celebrate.

We get to define what that looks like.

Seeing Change as an Opening, not a Loss

It is natural to grieve the loss of old traditions. But change does not have to mean emptiness. It can mean creativity, connection, and possibility.

Divorce makes room for:

• New voices in the planning process
• New activities that better fit the family now
• New meaning in how you choose to gather, rest, and celebrate

Parents often discover that releasing unrealistic expectations creates space for genuine ease and joy.

Ideas for new, low-pressure Traditions

New traditions work best when they feel small, doable, and enjoyable not like another item on the holiday to-do list.

Here are a few “bite-sized” ideas some of my clients came up with:

1. A Five-Minute Tradition

Light a candle together and each person shares one thing they are grateful for.

2. The Cozy Tradition

Declare one night “Pajama Holiday,” where everyone wears PJs, eats something simple, and watches a favorite movie or reads aloud.

3. A Tradition of Giving

Choose one meaningful, age-appropriate act of generosity—donating a toy, baking cookies for a neighbor, making cards for a shelter.

4. A Nature Tradition

Take a holiday morning walk, collect leaves or pinecones, or simply breathe fresh air together before the day unfolds.

5. A Creative Ritual

Make or choose an ornament that represents something meaningful from the past year. Over time, the collection becomes a family story.

None of these require elaborate planning, perfect behavior, or an Instagram-worthy backdrop. They simply create a touchstone—a moment that says, we are here, together.

Permission to simplify & savor

The holidays can quickly become performative: perfectly wrapped gifts, elaborate meals, orchestrated schedules. But for families navigating transition, simplicity is often the greatest gift.

Give yourself permission to:

• Drop traditions that feel heavy
• Keep only the pieces that bring genuine joy
• Say no to obligations that drain you
• Choose rest over perfection

When parents lead with calm and authenticity, children feel it. What they remember years later is rarely the matching outfits or the spotless house—they remember the warmth, the laughter, and the ease of being together.

Reimagining the Holidays as a Family Story in Motion

Traditions are not relics; they are living practices that evolve as families evolve. Divorce may bring an ending, but it also offers a beginning. A chance to craft experiences that reflect who your family is now and where you are headed.

As you reimagine your holidays, trust your instincts.
Start small.
Let go of perfection.
Invite your children into the process.
And savor the moments that feel good.

In doing so, you are not just creating new traditions you are building a strong, resilient family identity rooted in love, creativity, and connection.

Happy Holidays to you and yours!

With warmth,

Diana

Holidays can bring unique challenges for divorced and separated families, as I experienced firsthand with my own children. Their father and I were separated for seven years before finalizing our divorce, and without a formal parenting plan, we relied on conversations to arrange holidays.

Birthdays, Thanksgiving, and Christmas were especially challenging holidays for our family since our ability to communicate was often strained, leading to confusion and sometimes stress around these special days. Coordinating with ex-spouses also added complexity and conflict, making holidays a time we didn’t always look forward to. Unfortunately, the challenges around these holidays left long-term scars for my children.

Because of this personal experience, I strongly advise divorced and separated parents that a clear, thoughtful holiday parenting plan can make all the difference. What is most important is not where the kids spent the holiday day but what memories were created.

Here are my five tips to create a holiday plan that truly supports your family, helping everyone enjoy the season with less conflict and more peace.

1. Take the time to establish a clear holiday schedule
   It’s easy to gloss over the holiday schedule in the parenting plan, especially when there are so many other issues to tackle. However, holiday schedules are crucial to ensuring a smooth transition for everyone involved. Skipping over these details often leads to last-minute conflicts, misunderstandings, or hurt feelings, which can put stress on the whole family. Make time to create a schedule that both parents can agree on and avoid leaving things to chance.
2. Discuss the Holidays important to each parent
   While many parents think primarily about Thanksgiving, Christmas, and New Year’s, there are other significant holidays and observances that might hold special meaning for each parent. Take time to understand which holidays or traditions are especially important and discuss how both parents would like to approach these days. This conversation helps both parents feel heard and ensures that each has the opportunity to celebrate with their children in meaningful ways.
3. Avoid putting children in the middle of Holiday decisions
   Asking children where they would like to spend a holiday can place unnecessary stress on them and create divided loyalties. Instead, parents should approach the holiday schedule with a unified message. For instance, saying, “Your mom and I have worked out that you will be spending Fall Break with her this year and Thanksgiving with me,” can provide clarity and reassurance. When parents work together to communicate this plan, it helps children feel secure and removes any burden of decision-making from them.
4. Don’t forget about adult children
   While holiday planning often focuses on younger children, adult children can also feel torn between their parents during the holiday season. Adult children, too, benefit when parents communicate openly and avoid putting pressure on them. By working together to plan holiday time, parents can help adult children avoid the guilt or stress of feeling like they have to choose between parents.
5. Consider whether spending Holidays together works for you
   For some families, spending the holidays together shortly after separation can provide a sense of familiarity and comfort for children. However, it’s essential to think about whether this arrangement will be sustainable long-term. As parents start to build their own routines, new traditions, and possibly new relationships, it might become challenging to spend holidays together. Consider what’s best for everyone in the long run and remain open to adjusting plans as time goes on.

Contrary to what you may hear, you are not required to adopt the statutory holiday schedule. It is often the cookie cutter approach that attorneys tell their clients they must follow. Very few cases ever spend time crafting a holiday parent-time plan that supports their unique family. Creating a holiday parenting plan may feel complex, but it’s a valuable investment in ensuring positive family experiences. With clear communication, flexibility, and a focus on the well-being of the children, parents can develop a plan that supports everyone through the holiday season and beyond.

For more information or if you would like support in drafting a parenting plan, feel free to reach out to me and my team at (801)464-4004 or assistant@telferfamilylaw.com.