Your Mistakes Are Not Fatal
I was recently reminded by some other fellow coaches that we all make mistakes with money and that, frankly, our mistakes are nothing to be ashamed of. Indeed, they are part of the reason we are better coaches than we would otherwise be if we had done everything right in the past. Someone had asked for specific stories, so here's what I told them:

My husband and I are living proof that you can make several major "oopsies" and still
succeed. Back in the 80s, as twenty-somethings with more money than brains, we got into tax-shelter investments that took about $800/month from us and we never saw any return other than some minor tax deductions. We're lucky we never got slammed with tax penalties after the fact. (Lesson: Don't invest in things you don't understand.) Then we got into nothing-down real estate and spent years chasing bad tenants who didn't pay, evicting them, or replacing copper plumbing after they disappeared in the dead of night. (Lesson: if you buy rentals, do it with cash and screen your tenants carefully.) We didn't budget, but we made decent money (though never more than 180K combined at our peak) and thankfully lived below our means somehow and stayed out of debt other than our mortgage and those stupid rental properties. (Lesson: Living below your means gives you the margin to save and invest for the future.) We also had whole life insurance policies -- cashed them in after finding Dave Ramsey, and got almost exactly the same amount back that we had paid in premiums over the previous 20 years. (Lesson: Buy only term life insurance .) But we still managed to pay off our 30 year mortgage in 12 years, then had sufficient savings and cashflow to send our 2 daughters to private Christian colleges and one to vet school with no debt. We also during that period sold some investments at the bottom due to panic. (Lesson: Get a professional to keep you from jumping off the ledge.) Now at age 60 and 62 we are retired with just shy of a 2 million dollar net worth. I still have frequent pangs of regret knowing that could have been 5 million or more had we not made those stupid mistakes. I guess that's my motivation for coaching, kind of like Dave Ramsey says.....God saved us from our own stupidity, so now He makes me teach this stuff.