
How to balance generosity, guilt, and expectations with money
with Sarah
Money is never just about numbers. It’s layered with emotion, shaped by past experiences, and often tangled with family dynamics, guilt, and expectations. When Sarah received a substantial financial settlement after her divorce, it gave her control over her financial future but also brought new challenges. How much should she give to help loved ones? How could she protect her long-term security while being generous? And how could she spend on herself without feeling guilty?
Introducing Sarah
Sarah has always been cautious with money, shaped by childhood memories of watching her parents work hard to provide stability. But now, managing her financial future alone while feeling a deep responsibility for her family, who are facing their own struggles, has created emotional tension. Not earning as much as she used to has only added to the pressure. Sarah is now navigating the tricky balance between generosity and self-care, questioning how to set boundaries, when to give, and how to feel good about enjoying her money.
Sarah’s childhood money memories
Sarah’s early memories of money were marked by gratitude and generosity. Her parents worked hard to provide a private school education while quietly helping less fortunate children. It was only later that she learned about the sacrifices her parents made. Her father had taken a financial risk by signing surety for a friend, which eventually led to liquidation. Yet, somehow, they managed to keep their home and give their family stability.
Sarah’s mom returned to work, something her parents felt guilty about, but in hindsight, Sarah believes it was a gift. “My mom did incredibly well, and I think it shaped my work ethic. Both my sister and I learned to work hard and be entrepreneurial.” Those early lessons left their mark. They taught Sarah the value of resilience, hard work, and helping others – values that still shape her relationship with money today.
When financial freedom feels heavy
Receiving a large financial settlement after her divorce gave Sarah a sense of control over her future and brought new pressures. “In some ways, having control over my destiny was a relief. But I also became more anxious about money. I have to make all the decisions for my future now, and I feel a deep sense of responsibility to care for everyone around me.”
Sarah is cautious about managing her money, especially when it comes to spending on herself. She avoids major luxuries and feels guilty about indulging when others around her are struggling. “I think about my retirement a lot. I don’t want to overspend now and be uncomfortable later.”
Money and family relationships
Helping family has been so rewarding, but it has also been one of Sarah’s deepest challenges. At first, Sarah gave freely, often offering more than was asked and stepping in even when no one had asked. But over time, she quietly questioned how that money was being used.
That tension made her rethink her approach. Now, she waits until she’s asked for help and focuses on small, meaningful gestures, like paying for sports kits or extra lessons as gifts – often linking them to birthdays or special occasions.
“I’ve learned that I can’t help and save everyone. I’m trying to practice ‘Let Them’ and only give what I’m comfortable giving. I want to focus my support where it makes a real change.”
Expectations, regrets and boundaries
For Sarah, the challenge hasn’t been about the act of giving – it’s been about the conversations that didn’t happen. When you gift money to loved ones, and they make choices you disagree with, it can be deeply frustrating. For Sarah, this led to avoidance, misunderstandings, and the unsettling question of whether her help had truly made a difference or simply delayed a deeper issue.
Learning to give without expectation is still a work in progress. “I’ve realised that it’s about giving what I can, knowing my limits, and focusing where I can make an impact.” For Sarah, it’s also about finding peace with giving. Knowing she has done what feels right without carrying the weight of how others choose to respond.
Balancing giving and embracing joy
For Sarah, spending on herself doesn’t come easily. She worries about the future, whether she’s saving enough, and whether spending on herself will compromise her security later. And then there’s the guilt: spending on herself when others are struggling feels uncomfortable.
But Sarah is learning that money isn’t just for saving or giving. It’s also meant to be enjoyed. It’s meant to enable a full and meaningful life. “I’m making a list of things I love doing, small and big, and committing to making them happen.” She also sets clear spending plans for personal spending and giving to others.
Working with her financial planner has been an important part of that process.
“Trusting myself more, recognising the good decisions I’ve made, and knowing I can revise my plan when needed has built my confidence.”
Money Lessons to Take Forward
- Boundaries are healthy. Helping others should never come at the cost of your own financial well-being.
- Communication matters. Honest conversations can ease tension and clarify expectations.
- It’s okay to enjoy your money. Guilt doesn’t have to shape every spending decision.
- Plan with intention. Knowing what you want to spend, save, and give creates peace of mind.
Money is emotional, but it doesn’t have to be overwhelming. It’s about finding the balance between being generous, planning wisely, and allowing yourself to embrace the joy that money brings.
Always remember, when it comes to your money, be inspired, be brave, and be on purpose.
Kim.

