When giving brings guilt and expectations

I notice this often – how easy it is to feel guilty about spending money on ourselves when those we love are struggling. And it’s not just about who we feel we should help, but also when we choose to help. Do we step in only when someone asks, or do we offer because we see them struggling? And when we do help, do we let go, or do we quietly hold expectations about how that money should be used?

I’ve seen this play out in many of my clients’ lives – and I’ve experienced it personally. For years, I felt compelled to help whenever I noticed someone I cared about was in trouble. But I’ve learned that stepping in isn’t always as straightforward as it seems.

I remember lending money to a family member, only to find out later they’d used it to go on holiday. I was irritated. How could they use the money for something I wouldn’t have chosen? That experience taught me an important lesson: while I had offered the help, I’d also attached unspoken expectations. And when those expectations weren’t met, it left me feeling frustrated and resentful.

Here’s what that experience taught me:

1. Check your expectations: Sometimes, people haven’t even asked for help – we step in because we feel we need to. But when we do, it’s important to ask: Am I giving with strings attached? Do I expect appreciation, repayment, or for the money to be used in a certain way? If so, is that fair?
2. Pause before jumping in: It’s natural to want to rescue, but offering help before someone asks can create its own tension. Sometimes, people need the dignity of making their own decisions – or even mistakes.
3. Release the guilt: It’s easy to feel guilty for enjoying what we’ve worked hard for, especially when loved ones can’t do the same. But it’s okay to honour your own financial goals and dreams. Helping others should come from a place of love, not obligation or guilt.

These lessons aren’t always easy, but they’ve helped me approach giving with more clarity and compassion – both for myself and others. I’ve come to realise that most of my joy comes from giving as a gift, without expecting anything in return. When I let go of the outcome, I also let go of the potential for disappointment. That simple shift has allowed me to truly feel the happiness that comes with giving from the heart.

Kim