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How to not fail at retirement ?

Posted By Sean Westcott  
08/06/2026
11:08 AM

Last year I decided retire from corporate life and return to Australia. I was talking to a good friend who had made the same move a few years before me and he asked me if I had a plan to avoid being a failed retiree ?

What's a failed retiree, I asked ? There are two types - the first who thinks they've made a terrible mistake and returns to corporate life - and often finds that was not the answer either. The second who realises that their work was a big part of their identity and without it they find themselves lost.

The obvious question is how to avoid this, and my friend had a simple but powerful way forward.

Think about what is important in your life and create 5 'buckets'. For example, it could be Family, Community, Art/Music, Health/Sport, Business and so on. Once you've defined these 5 'buckets', you plan some experiments to see what resonates and gives you purpose and meaning. It's like trying on clothes to see what fits and suits you, but instead of clothing, it is activities and experiences. Maybe it's taking an art class, working with a NGO, or getting involved with Rotary.

The key thing is to remember these are experiments, and not commitments. It's important to reflect and to keep what is working and let go of what is not. It's not what others think you should do, but what works for you.

I've taken this advice to heart, and it's really working for me. For example, I've taken up paddling an ocean ski, met a great group of people, and I spend time on the water enjoying nature and looking after my health.

If you're thinking about retirement or pivoting to a different career and lifestyle, I really recommend this approach and hope it can help you succeed at retirement.