Why Successful People Feel Guilty About Spending Money
My client had just finished telling me about their dream to trace their family tree in Sweden and experience the Northern Lights there. I asked when they planned to go. “Oh, I don’t know, down the track”, they responded. When I mentioned that he had the money and time to go now, they smiled awkwardly. “It just feels very indulgent, spending that much on myself.”
It was a response I’ve heard numerous times from successful business owners. They’ve worked hard and reached a level of financial success and security they perhaps never imagined. But they struggle to enjoy that success because spending money on themselves feels wrong somehow.
Whether it’s a once-in-a-lifetime experience they’ve been postponing, splashing out on the car they’ve always wanted, or investing in a holiday home the entire family can use, they all come with guilt in the background.
Where does your discomfort come from?
The psychology of wealth is complex. We’ve been culturally conditioned to link spending with indulgence, frivolity, or worse – appearing ostentatious. There's an unspoken fear of judgment from others, or perhaps a nagging voice asking whether you've truly "earned" the right to enjoy what you've built.
For many people, wealth has always meant security and future planning. It’s superannuation, investment properties, and leaving something behind. The idea that wealth could also be about present-day freedom, experience, and joy doesn't always feature in the equation.
Responsible enjoyment doesn’t equal reckless spending
There's an important distinction here. Enjoying your wealth responsibly is fundamentally different from reckless spending. One enhances your well-being and reflects your values; the other creates financial instability and purchase regret.
When you have the right structures in place – when your financial foundations are solid, your future is planned for, and your business is sustainable – you’re free to make a spending choice. One that doesn’t come with risks.
What might responsible enjoyment look like for you? It could be:
Meaningful travel that creates lasting memories,
Quality purchases that enhance your daily life,
Philanthropic giving that reflects your values, or
Moving to semi-retirement or retirement earlier than planned.
The benefits of a balanced approach
Allowing yourself to enjoy wealth responsibly can actually improve your relationship with money. It reduces the guilt and anxiety that often accompany financial success. It helps you make decisions that align with who you are as a person and how you live your life. And it reminds you why you worked so hard in the first place.
Multiple studies have found that experiential purchases such as travel, dining experiences, and events consistently lead to greater happiness than material purchases, regardless of cost. When you view wealth as a tool for creating the life you want, not just as a number to protect, your decisions become clearer and more purposeful.
How Accounting Heart supports confident decision-making
Our role isn't to tell you how to spend your money. Instead, we help you feel confident that your financial foundations support the life you want to live.
We provide structure, clarity, and guidance so you can make informed decisions that feel right. When you know your business is structured efficiently, your wealth is protected appropriately, and your future planning is on track, you can make choices about your enjoyment today without second-guessing yourself.
Building a healthier relationship with money
If you've been holding back from enjoying what you've built, it might be time to examine why. Understanding the psychology of your own relationship with money helps you make mindful decisions that serve both your present and future self.
With the right financial structures and trusted guidance, you can move forward with confidence, balance, and purpose – using your wealth in ways that genuinely enhance your life. After all, financial success isn't just about what you accumulate. It's about what you create with it.
Disclaimer: This is general information only and is not advice of any sort. No warranty or representation is provided by Accounting Heart Pty Ltd as to the accuracy, currency or completeness of the information contained in this blog. Readers of this blog should not act or refrain from acting in reliance upon any information contained herein and must always obtain appropriate taxation and/or other advice as may be appropriate, having regard to their particular circumstances.