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This could be a long list. Firstly, I mistakes are just part of the learning process. The person who makes no mistakes, and takes no chances, is making a huge mistake!
You see that with some bitter and twisted people who have been let down by others in life (haven't we all been), and then they just give up taking risks and therefore making as many mistakes.
The key thing is to learn from mistakes, rather than to always assume that it is "better to be safe than sorry".
Some of the things I would do differently would be:
1. Learn more languages when I was young
2. Not wasted time. We all don't value time as much when we are university students and get 3 months break. Time is the most important asset though.
3. Read more about personal finances from a younger age. In fact, read as much as possible outside my core subjects studied at university.
4. Learned more about the online world when I started my working career. When I started working, the world was at a crossroads. We were moving quickly to an online world in the 1990s and 2000s, yet most of the people making decisions were from the older generation. Most of the younger generation were being trained by the old guard. So, even as recently as 2010, 2013 or 2019 would you believe, some people honestly believed things like "business is best done face-to-face".
5. Linked to the last point, I wouldn't have taken, on face-value, the tips and suggestions of many of the old guard when I started out.
6. I would have started my own business sooner than I did.
7. Be more selective about who I associate myself with, to avoid toxic people.
8. Broken as many industry norms as possible. Normal actions lead to normal results. Extraordinary actions leads to extraordinary results. Almost all my best results have came from doing the opposite of what the majority do in my industry.
9. Taken even more calculated risks and doubled down on my choices.
But having said all of that, I am pretty satisfied with most of my choices. A rational person can only deal with the information they have at the time of making the decision.