27 Jun 2025

Thinking: Can you change your life – just by asking the right questions?

Someone recently asked me who has been a role model to me in my industry. And my immediate answer is George Kinder, who is the godfather of Financial Life Planning. At a time when financial advice was largely a sales arm of large insurance and pensions companies, Kinder was one of the pioneers of taking the time to engage in much broader discussions around life and meaning. Including thinking about deep fulfilment, and the role of money as a means to those ends.

Kinder starts with three potentially seismic questions.

1. “Imagine that you are financially secure, that you have enough money to take care of your needs, now and in the future… How would you live your life? What would you do with the money? Would you change anything? Let yourself go. Don’t hold back on your dreams. Describe a life that is complete, that is richly yours.”

Thinking this question through can, in itself, be quite a revolutionary act. Many will start with a rest from their normal grind. Or believe that they’ll simply retire. But you have to dig into what that actually means. What you’ll then do with your time and energies. It’s not nearly as simple a question as it might first seem, because a fulfilling life isn’t necessarily un-challenging, or just one long holiday (that gets boring pretty quickly). But a fulfilling life also doesn’t have to be one that costs millions, in fact, many people make the mistake of thinking they have to keep doing things they don’t enjoy because they haven’t taken a careful look at what they really need for their life (not what their neighbours need, or what society tells them they want) and whether they might already be able to afford this.

2. “[Now imagine…] you visit the doctor who tells you that you have five to ten years left to live. The good part is that you won’t ever feel sick. The bad news is that you will have no notice of the moment of your death. What will you do in the time you have remaining to live? Will you change your life, and how would you do it?”

This question creates urgency, speeding up the clock. We realise that waiting to live the good life ‘some day’ isn’t viable when your timeline is shortened. This can help you with creating a ‘bucket list’ of things you really want to do, or be, before the end comes. This can also help you to clarify your most deeply held values – the things you give greatest priority to.

3. “This time, your doctor shocks you with the news that you have only one day left to live. Notice what feelings arise as you confront your very real mortality. Ask yourself: What dreams will be left unfulfilled? What do I wish I had finished or had been? What do I wish I had done?”

This question probes whether your plan for your life actually reflects your priorities. Do you spend your time in a way that reflects what you care about? What do your financial habits say that you value? Which things on your bucket list are you most regretting missing?

Conversations with people on their death-beds find they wish they had:

• lived the life that was truly theirs instead of what was expected of them
• the courage to express their feelings
• spent more time with their friends and family
• worked a bit less and let themselves be happier instead of worrying what others thought of them.

These are not straightforward conversations, and Kinder’s Life Planning outline is very much a higher-order domain when it comes to our hierarchy of human and financial needs. But when last did you have a meaningful conversation around what you can do, what you want to do, and how you might achieve those things?

If you would like to discuss any of this further – book a free initial chat together.
https://calendly.com/duncan-bw-hoebridgewealth/30min

None of the above is financial or investment advice and you should speak to me or someone else professionally qualified to give you advice specifically tailored to your circumstances.