It is my viewpoint that there is no rush to attain one's career goals in their 20's - rather, this is the time for travel and achieving other goals which can only be done during this time period (eg sporting). I met a guy in Austria who worked at a bar on the mountain during Winters, and on boats in the Mediterranean in the Summers. I'm intrigued by living this sort of lifestyle as a temporary alternative to the white-collar path. Eligibility for most working holiday visas run out at the age of 30, so, it seems like this is the best time for it.
Who thinks it is at all possible to return to the corporate path after working abroad doing low-skill jobs with zero relevance for several years?
Thought I might flesh out a more specific/ updated game plan: continue on the 'prestige' track for several years (most likely sell-side finance), saving up as much money as possible. Testing the career on the side - eg what @mech60 suggested with doing the sort of work I intend on the weekends. Buy equity in a small business in sport tourism sector with the potential for operational improvements or a roll-up etc. If it fails, I'm only 1-3 years deep and play it as an entrepreneurship experience and return. My plan Z is continuing family property development biz. Feel free to punch holes, or add some advice on how to further mitigate the extreme potential downside.