14 Complicated Situations I Can Guide You Through (as your Financial Sherpa)

We often think of finances as a calculative and dry subject. We believe that the cold numbers will lead us to an objectively correct way to spend our money. However, life is full of unexpected and difficult choices and sometimes there isn’t a purely data-driven answer available.

In these times you need to examine factors like your mental state, your money story, future goals, and personal relationships to figure out what is right for you. I’ve covered 14 situations of times that disrupt our emotions and make it the most challenging to make a smart decision.

Table of Contents:

1. Managing Finances After the Death of a Spouse
2. Dealing with Financial Imbalances Between Partners
3. Getting Your Bearings after a Divorce
4. Unexpected Financial Windfalls
5. Windfall Falling Through
6. Economic Shifts Outside Personal Control
7. The Money Side of Having Children
8. Caring for Elderly Family Members
9. Being Responsible for Extended Family
10. What to Leave my Kids
11. Engaging in Meaningful and Personal Philanthropy
12. Harnessing Our Inner Bag Lady
13. How to Understand My Money Story
14. Healthily Reflecting on Our Financial Habits

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Managing Finances After the Death of a Spouse

The death of a loved one starts you on an emotional rollercoaster. Everything happens abruptly and your surroundings can blur together. There are no places to get off and you’re forced to ride it out until the end.

For most people in this situation, collecting and organizing financial information is far from the front of their mind. However, certain financial decisions can’t be put on the back burner for long. Important payments like your mortgage require action even in times of grief.

So, if you’re feeling overwhelmed, then it might be a good idea to bring in a professional to help you prioritize. They’ll take care of everything that needs immediate attention so that you can have the time you need to grieve.  

This process allows you to approach your finances from a healthy, stable perspective. After all, grief can convince us to make rash and improper decisions.

In the meantime, take the time to get your emotions in order and seek out help if you need it. Visit support groups and speak to people in similar circumstances. Get as close to normalcy as possible with your children, friends, and family.  When you’ve settled down, then you’ll be able to make financial decisions that take care of your future and honor your partner’s wishes. 

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Dealing with Financial Imbalances Between Partners

There are many reasons why one partner may earn less than the other. Perhaps one of you left your job to take care of the house and children. Maybe one of your chosen professions is more lucrative. Regardless of the reason, power imbalances can take a toll on even the most loving and supportive relationships.

When one person is less financially stable as an individual, it can feel like they have a smaller voice in related decisions. Feelings of inadequacy or loss of personal power will inevitably lead to an increasing number of arguments.

This could also appear in the form of guilt from both sides. While the lower-earning partner can feel like they’re not contributing enough to the relationship. That they’re being one-sidedly cared for. On the other hand, the higher-earner can pick up on these feelings and develop guilt over harming their loved ones. Inadvertently or not. 

Combating this requires understanding what each person values in the relationship. Maybe their Money Story led them to place a lower value on financial contributions. Maybe they grew up truly believing that all money is shared in a partnership. Through understanding each other’s money stories, you can truly understand what you bring (or don’t bring) to your partner’s life. 

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Getting Your Bearings after a Divorce

Divorce is an emotional death. It’s the symbolic representation of taking your relationship and burying it 10 feet deep. However, unlike the ancient Egyptians, our assets and wealth aren’t buried with the body.

Emotions of fear and anxiety can crop up when you go through a divorce. There’s the obvious fear of ceding your involvement in your children’s lives to your ex-partner. But there are also fears of losing your lifestyle and your future security.

Getting over this fear is necessary to have a fair and clean divorce. If you don’t, then you’ll be approaching conversations under a combative cloud. The importance of an asset to each partner isn’t necessarily 1:1 with its financial value.

Understanding your ex-partner’s money story will greatly help in divvying everything up so that you each get an equal share of what’s important to you.

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Unexpected Financial Windfalls

So, you’ve had a stroke of good fortune and money has unexpectedly fallen into your life. You probably have a laundry list of things you’ve always wanted if only you had the money to buy them. But there’s a difference between a list of things you dream about and what you need.

Scrap that list. It’s time to make a new one.

Keep in mind that a financial windfall has innate value even if you don’t spend it on anything at all. However, if you’re adamant about a “use it or lose it” mindset, then try to incorporate your values into the purchasing decisions. Learn what types of things bring you the most emotional satisfaction or freedom.

By understanding what’s most important to you, you’re able to better align your spending with your value system. Rather than seek instant gratification, it’s better to use it on long-term investments that fulfill yourself in a myriad of ways.

For example, do you feel weighed down by credit card or student debt? Wouldn’t it be liberating to finally be rid of it (or at least a chunk of it?)

Do you value time spent with your family? Then buy something that you all can do together and build memories with. Learn to direct your purchases in this manner, and you’ll gain much more satisfaction from your good fortune.

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Windfall Falling Through

We structure our lives around certain certainties or what we believe are certainties. Things like being paid on time this week. Getting at least ‘X’ amount of money in our Christmas bonus.  You may even be counting on receiving money left in someone’s will.

We sometimes forget that nothing is ever certain. Bonuses can be canceled, paychecks can be late, and wills can be revised without anyone knowing. Even if you’re holding onto an investment or an asset, until you’ve taken steps to cash out on it, then it’s not 100 percent reliable. Stocks can plummet and property can drop in value. Nothing is certain. Maintain the mindset that money you can’t hold in your own two hands isn’t yours.

However, if you’ve already made the mistake of spending money you don’t have, then you need to get on damage control. Get the money back if possible or find ways to cut down your spending until you make up the difference. The slower you move, the bigger the problem becomes.

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Economic Shifts Outside Personal Control

It sucks to say, but life isn’t fair. Our finances will be pressured at times regardless of how responsible and fiscal we are. Global events like pandemics, wars, and political schemes can ruin economies and wrench our jobs away from us.

This unfairness unleashes anger and pity for ourselves. An understandable response for when the world gives us the bird. But just as there was nothing you could do to stop it from happening, there’s also nothing you can do to change it.

So, we should learn how to ride the waves as gracefully as we can. Figure out where you can cut costs in your daily life and look for temporary (possibly lower-paying) jobs to tide you over. Do whatever you can to get yourself stable enough to stand tall once more.

Above all, never convince yourself that, “Things can’t get any worse.” There’s no guarantee that whatever caused your problem won’t continue. Because it can. But adapting quickly is the key to minimizing damages and preserving the key parts of your lifestyle.

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The Money Side of Having Children

One of the biggest choices we ever have to make in life is the decision to bring children into it. It’s not a simple shower idea that you’re rolling with on a whim. There are hundreds of things to consider, like your maturity, available time, and financial state.

It requires you to partially look into the future. To predict what your life will look like, and how it will transform after you have a child.

Even if you think you’re well off, the costs of a child can be painfully surprising. Things like insurance, medical bills, specialized food, toys, and sleeping equipment will strain your budget. Not to mention the diapers. More diapers than you can imagine.

You need to consider what you and your partner are willing to give up and what you’re not. Things like personal training and fancy restaurants may need to be put aside for a while if you want to give your child the life you imagined. What’s removable from your life while still allowing enough resources to fulfill yourself? After you know that, ask yourself, “will giving those up let me save enough money to raise a child?”

This doesn’t only apply when your children are chubby and cute. It extends to the moodier phases as well. There are two life events that many parents dread having to pay for.

College and marriage.

Both are ridiculously expensive events in your child’s life. You need to decide early on a reasonable target you want to hit and how much you want to help your child. Like with all goals, setting a target greatly increases your odds of reaching it.

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Caring for Elderly Family Members

As we get older and gain more life experience, we get a better perspective of what our parents went through to raise us. So, when it’s our turn to take care of them, it’s hard to say no, even if it’s not what we imagined for ourselves.

If you assume the role of a primary caregiver, then you’re over 10 percent more likely to report financial difficulty than secondary caregivers. After all, you’re taking on an adult who likely has a variety of medical needs.

Look for the early signs. If you know that illness runs in your family or your parents may struggle in their later years, then you’ll want to start preparing early. If possible, put aside some money to cover their future living and medical expenses.

Do your research and be honest with yourself about how much their care will cost you. It might not be enough to save whatever just happens to be left over. You might have to give up certain luxuries if you want to save enough for their future.

To get a good estimate of your parent’s future expenses, discuss what THEY expect from their future. You might not be able to provide everything, but it’s a good starting point to find some common ground. There’s likely to be a large number of concessions, but remember that it should be a 2-way street. It’s vital that you both find ways to stay happy without trampling on the other’s lifestyle.

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Being Responsible for Extended Family Members

One of the less desirable consequences of success is the barrage of expectations you get from those around you. They expect you to help them out because “you can afford it” and they turn you into the villain for not doing enough to share your success.

This can be particularly frustrating when these expectations are coming from your spouse’s side of things. The over-reliant family is a classic hook seen in dozens of family comedies. Common cast members include the hateful mother-in-law, the overbearing father-in-law, and the deadbeat brother. 

It’s hard to find the line between helping out family and being taken advantage of. But you must strike the right balance if you want your spouse to maintain close ties with her blood. Many couples try to reach an agreement with the extended family, but that isn’t the correct approach.

In the end, you’re doing this for your spouse. So, they need to have the biggest voice in what’s acceptable. It’s their money story and emotions that will decide if you’re helping too much or too little. Before you hand over a cent, make sure that you create guidelines for the generosity that you’re both happy with.

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What to Leave my Kids

Raise your hand if you enjoy speaking to spoiled and entitled children. Anyone? I didn’t think so.

Everyone wants to raise their kids to be upstanding and successful people. Leaving them too much money after you pass might give them the agency to learn lessons that go against that goal. Alternatively, leaving them nothing may hurt their feelings.

You want to leave them enough so that they can feel secure and that they know you cared for them. Finding this sweet spot is like performing advanced calculus without a trusty “TI” calculator.

It starts with dissecting what each child wants to achieve in their life. What kind of lifestyle do they want to lead and what dreams do they want to pursue. Their money story, both past and present. Considering all of this show them, on an emotional level, that you understand them and want what’s best for them.

As their parent, you play an ENORMOUS role in developing their money stories Become a model of the financial credo that you want your children to adopt and let them know what’s important to you. Do you value taking financial risks or playing it safe? Is frugality important to you? Teaching your children these things about you tells them what to expect when you pass.

So, as long as you practice what you preach, then your children are more likely to be understanding and respectful of what you leave them.

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Engaging in Meaningful and Personal Philanthropy

There are literally thousands of charitable efforts out there. Choosing which ones to dedicate your time, emotion, and money toward is going to come down to your money story. People tend to engage more deeply in philanthropy when they’re both knowledgeable and connected to the cause.

So, it stands to reason that you’ll be most helpful to organizations that meet those requirements. You’ll need to understand how different organizations operate to achieve this. Find ways to engage with them and come to each conversation curious.

Ask their representatives and volunteers questions to see if they align with your desire for change. This includes queries about their current and future plans. If the cause doesn’t ignite your passion then keep searching for one that does. This will enable you to throw yourself into it more completely.

Understand that meaningful philanthropy isn’t about how big of a check you can write. If you’re not engaging on an emotional level, then whatever you do will feel empty and unfulfilling.

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Harnessing Our Inner Bag Lady

Bag lady syndrome refers to a woman’s fear that, at any point, she’ll be thrown to the streets and have to carry her possessions in a shopping bag. These uncertainties manifest in men as well, however, the trend is more prevalent in women given our lower pay and the pressure on us to leave the workforce.

There are times when this concern comes over me and takes a place in my decision-making. This isn’t all bad. While you shouldn’t let your bag lady syndrome take full control; there are benefits to listening to it every once in a while.

Rather than giving in to the fear, channel it to develop responsible habits in managing and reviewing budgets. Use your concern to motivate you into taking a more active role in your investments and build up reliable safety nets. It can even add a sense of fulfillment when you take it into account.

After all, your bag lady syndrome is part of your money story too. And like with all parts of that story, you gain positive feedback by aligning your financial habits with it. Every time you come under budget will feel that much better.

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How to Understand My Money Story

Our money story is defined by all the lessons we’ve learned in our life. Financial or otherwise. It’s the reason that some of us are frugal while others derive joy from frequent spending.

Money stories are a form of emotional expression and understanding them is crucial to making fulfilling money decisions. I work with clients to uncover their money stories and learn how to set goals with their value systems in mind.

Through my workshops and seminars, we hone in on the explicit and implicit messages you’ve been exposed to. Obvious examples include whether you grew up in luxury or watched a family member ruin their life through irresponsible spending. We take these messages and figure out how they have shaped your current habits. This helps you create plans that remove negative feelings about your money and start to use it in a uniquely meaningful manner.  

My own money story stems from the tumultuous marriage between my refugee father and depression-era mother. After which my mother was forced to drastically alter her lifestyle. It made me develop a hyper-awareness of any risks a venture might have.

Taking an objective viewpoint is vital in uncovering your money story. We all know how easy it is to lie to ourselves about our past. Discussing your background with a professional or [the right] friend will help you immensely.

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Healthily Reflecting on Our Financial Habits

It’s always a good time to look back and evaluate how you’re using your money. It gives you more relevant insight for determining what goals to set moving forward and if your recent choices reflect your money story.

I’ve worked with clients who beat themselves up over failing to stick to their budgets. They restrict themselves in January about how much they’re allowed to spend in December. That’s a little crazy if you think about it. Our circumstances and values can shift dramatically in brief periods of time.

Think about why you went over budget. Did you travel to spend more time with close family or friends? Were you investing more into hobbies that bring you long-term joy? Was there a charity or local project that you contributed to? If your choice of exceeding your budget brings you comparable fulfillment, then maybe it’s your budget that needs to be reevaluated.

Reconstruct your budget with your money story as the central theme. Think about your value hierarchy and make reasonable trade-offs to better match it. This process by itself can help reconcile the nervousness you feel about going over budget since it justifies how you’re directing your funds. Within reason.

If you need help navigating your thoughts and emotions around an important financial decision, you can contact me here or check out some of my online resources.

Preparing Your Relationship for Healthy Financial Discussions

Money is a hard thing to talk about. It fits right in between being honest with your doctor and discussing a “newly renovated” nursing home with your mother-in-law. 

In fact, we’re taught from an early age to avoid talking about money. Even straightforward subjects like salary and savings are hindered by a layer of taboo. So, imagine the herculean difficulty of trying to talk about any emotional aspects of the subject.

You’d think that communication gets easier the closer we are with someone, but we all know that isn’t always the case. Disagreements and differences in ideology can spell the end of a relationship if they’re put through enough stress. Most couples don’t want to invite that themselves and choose to steer clear of hot button subjects.

Avoidance only works for so long. Some unforeseen problem will shake your life from its axis and force you to talk about more than just current events. Due to the ubiquity of finance, at least part of that conversation will almost certainly be about money.

And it will test your relationship.

Now, it’s easy to believe the couples that fail this test just weren’t strong enough. That they hadn’t cultivated the openness and honesty of their counterparts.

Rather than a lack of honesty, I’ve observed that many individuals lack the necessary insight into their money story to explain themselves properly. A “money story” is the culmination of all the implicit and explicit financial lessons you’ve learned throughout your life. Our money stories are individually unique. As a result, we’re approaching the conversation from different perspectives which is a big factor in the difficulty in communicating about finances.

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Why We Struggle to Communicate

Knowing your financial habits and having insight into them are separate matters. Many people have no trouble explaining their general money philosophy. They describe themselves with simple terms like saver, spender, or investor among other things.

However, such broad definitions don’t cut it in a serious financial discussion, whether it’s with a personal or professional connection. Certainly, the spender will be looser with money while the saver will tighten their grip. They’ll continue to clash as each one struggles to understand why their partner won’t accept their point of view.

This will go on until the relationship breaks or someone thinks to ask, “why do you feel that way?”

• Why do you value a safety net so much?

• Why do you want to spend money on something like this?

• Why are you so keen on following the stock market?

Questions like these probe into a financial habit's emotional or historical reasoning. Instead of playing an argumentative numbers game of “cost v. benefit,” a couple with insight into the reasons behind their habits will form a deeper understanding.

This understanding helps them realize why it’s important that their partner act on their ideology to a certain degree. It’s not just about blindly spending, saving, and investing. Instead, the act of using money in a particular way provides feelings of acknowledgment, safety, validation, or other positive emotional responses. Values that both partners want for the other.

While the questions to ask are relatively straightforward, their answers will be more complicated to sort out. After all, our behaviors are like an emotional puzzle box built by a lifetime of expectations and experiences.

There are thousands upon thousands of pieces that cling together and shape our overall ideology. Little factors like opening a lemonade stand as a kid or your father’s rule of squirreling away 20 percent of every paycheck play a role. Locating the most impactful factors among them takes time and precision.

This becomes even more complex when we introduce an intimate partner into the mix. Having to integrate their feelings and viewpoints is akin to throwing in a handful of new pieces that we can’t find a place for in our puzzle.

It’s only when we share our money stories and present how we think and feel that we can create space for our partners. We rarely discuss this need in our day-to-day, so when it’s time to get serious, it’s hard to land on common ground. 

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Excavating the Money Story and Finding Common Ground

A few years ago, a couple came to me and detailed a situation that I can only describe as an intermittent war. The prize? Control over a hefty inheritance.

It was one of the classic scenarios between a spender and saver.

The wife earmarked the inheritance as a safety measure. Something to provide for their family if an emergency arose. A “break glass in case of hard times” fund. Her husband considered it an extension of their savings. Something to be used in the present to improve their lives.

Every purchase or expense eclipsing a standard grocery run would spark a contentious debate. Previously agreeable decisions like vacation destinations and home improvements became the backdrop for arguments that slowly eroded their marriage.

Despite the ever-growing conflicts, they continued to treasure each other and wanted the marriage to survive. They felt that it wouldn’t if this game of inheritance tug-of-war wasn’t somehow put to rest.

After hearing both sides’ opening statements, it became clear that the problem had only been approached from a fact-based vantage point. They repeated rationales like saving up for their children or the logistics of adding a third bathroom but didn’t understand why they valued their plans over their partner’s.

They had both grown up in less than favorable circumstances that dramatically influenced their perspectives. Just in different ways. They’d learned harsh lessons and, the harsher the lesson, the more its teachings are adhered to.  This is the emotional side of money that often drives our decision-making actions and behaviors.

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Her Anxiety

A depression-era home struggling to survive. She learned early on about the pain of living without a safety net. Doing everything to succeed but still surrounded by a family endlessly worried about the next morning.

Two siblings turned to substance abuse and she had the role of the “good and responsible child” hoisted upon her.. Her lesson was to always have a backup so her family could live with a light heart even when times got hard.

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His Reward

A father that was incapable of holding down a job. He learned how inconsistent providers hurt everyone around them. Rather than rely on employers, he founded his own company and created a high level of security for himself.

Everything he earned went toward his family because they needed it all. And he was happy to give it to them.

However, when a large sum of unexpected money came in, he wanted to reward himself for his work. He had succeeded where his father had failed and wanted to feel the benefits of that. This was the motivation behind his hyperfocus on using the inheritance money.

While his money always went to supporting his family, this extra money could be used as a reward and make him feel like his efforts had paid off.

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Give Some Ground for the Benefit of Both

Understanding your partner’s emotional reasoning is a way to initiate the discussion with common ground to jump off. In the end, you both want the other to feel satisfied and happy about how you’re using the joint money. However, chasing after emotional payoffs isn’t an excuse to be reckless with your finances.

The point is to pin down a way to fulfill both of your needs rather than prioritizing whoever has the more compelling backstory. We’re not in the business of emotionally blackmailing our partners. If only one of you compromises their needs at every turn, then discord will form and cause future conversations to become even harder.

In the inheritance case, the goal was to find a way to let the husband feel rewarded for his success while maintaining the sense of security it brought to the wife. You’ll notice that this is a completely different puzzle than arguing about who’s financial ideology should be applied wholesale to the inheritance.

One of the measures I suggested was creating a stipend. This was a pre-agreed amount of money that the husband had complete autonomy over. So, rather than feeling like nothing he earned went to himself, he could reward himself with an amount that didn’t threaten his wife’s comfort.

Of course, other conflicts arose from their unique experiences, but this was just one way that a little insight completely changed their conversation.  

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Keys to Having a Balanced and Safe Financial Discussion

While grasping your partner’s ideology is a huge help, it’s still possible for serious discussions to become unnecessarily heated. Setting up a few guidelines ahead of time can mitigate problems and keep the conversation flowing in productive ways.

1. Remember it’s a Conversation Not a Confrontation: Just as you’re not trying to antagonize your partner, they’re not trying to hurt you either. Keep the dialogue friendly and, if needed, gently address statements that make you feel attacked.

2. Appreciate Your Partner’s Values: You’re not in a relationship with a carbon copy of yourself. Each person brings unique values and perspectives to the table and it’s the collective’s responsibility to at least hear them out. Keeping an open mind can often keep disputes from turning into full-blown arguments.

3. Relationship “Shorthand” is Dangerous: It’s easy to assume you know everything about your partner, particularly in lengthy marriages. This leads us to continue discussions under certain assumptions which is a dangerous practice. If you take the time to confirm your partner’s thoughts, it could keep you from creating pointless static. One of my favorite expressions is to “come to the conversation curious.”

4. Take Time to Reaffirm the Relationship: Things can get passionate (and personal), but take a breath. Remind your partner, or be open to reminders, that the purpose of the discussion is to help you both. Come from a loving place and be obvious about it.

If a financial issue is disrupting your relationship and you want to communicate more effectively with your partner, then you can contact me here or reference our online resources.