Very reckless finance management, so I wonder if this correlates with not finding a "managerial" job.

First, "set out to explore Europe" immediately says "expenses". Without an income, that's teenager-level mentality.

Secondly, unless the house was still on mortgage, definitely it's cheaper to live on your own property and only scrap money for bills and food than paying rent on top of those. Also, and I'm not generalizing here, but people in general have parents / relatives. If times were that tough, I would retreat to my parent's house and rent the city apartment, that definitely buys me time.

And last but not least ... there are blue-collar jobs out there as a last resort. A friend of mine who lost his QA job, couldn't find anything else so he apprenticed as an electrician and now has got a license and works as such. Says he makes about the same as previously. There's "stacking the shelves at Lidl" also, not paying much but at least you're making something. And if you're willing to put up with the hard physical work and risk of accidents, there's always decent-paying construction jobs.

I'd say 2-3 months of looking are acceptable. After 6 months, some "plan B" needs to kick in, including the very mentally difficult idea of letting go of the past. You may have been a managing director but for the moment, the only option could be Lidl employee.