Self sabotage is the number one thing that stops people from really having the financial success they desire.
How do one break free from this mental demon that's bent on making us less than our true potential?
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I think the answer to this is highly dependant upon the person and how the demon affects them. Some general tips are to develop healthy attitudes to money but encouraging good record keeping and reviewing ROI, spending, regular expenses, subscriptions, income and time usage.
When I played poker, I would walk in with a set amount of money in my pocket and I either left when that money ran out or I was done for the evening (up). The one time I found myself breaking that rule - and yes, I did bust due to bad beats and yes, I could afford to "borrow" the buy-in from my budget for the next night - but that wasn't the point. Ten minutes into sitting down at a new table with my buy in, I cashed out then benched myself for 3 months. When the stakes of going degen are high then you have to be extremely harsh on breaches of discipline.