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Ask Sherry: The books that have changed my life and why

You asked, and I am answering every Friday once I have enough questions!

You can ask any question using the form here.

What is the book (or books) you’ve given most as a gift, and why?

I don’t really give books as gifts as a general rule.

Books are so personal, I can only really recommend good books and then hope people read them and come back to me raving about it.

That said, I have personally bought these books and would happily give them again as gifts to people who enjoy fashion:

And I have given these books for money-minded folks:

But again.. I don’t give books as gifts. It is rare that I do and only if I am CERTAIN they will love it.

Or what are one to three books that have greatly influenced your life?

Money: The Millionaire Next Door

It is not necessarily the book itself, it was more that it put FACTS in my face that actual millionaires save their money, spend wisely and are careful with it; that they aren’t the ones you see driving around in flashy cars or living in big homes — more often than not, those people are heavily in debt.

It is what kickstarted me into really evaluating my money choices, my life, what I was doing and why I needed focus and direction.

From it, I created The Budgeting Tool which got me out of $60K of debt to about a decade later, now with almost at $1,000,000 in personal net worth.

How has a failure, or apparent failure, set you up for later success? Do you have a “favourite failure” of yours?

My first failure was not sticking through to become a lawyer. I started pre-law and then… felt like a failure when I didn’t get it.

My brain just wasn’t cut out for it, it wasn’t that I couldn’t do it and was not detailed or organized enough, but I felt tired having to find flaws in arguments and to argue all the time, essentially.

My second was I almost quit my industry and career (which I now love) because I thought I would never make it. I just felt like it was all never going to make sense. Like I was listening to Klingon or something.

I thought I wasn’t cut out for it. I was stressed, I was putting in 80-hour weeks, it made no sense to me… I felt completely lost.

I stuck it out though, even though I felt like a failure at the time of my first projects, and after the fourth one, I GOT IT and realized my whole life was leading up to preparing me for such a career with such odd hodgepodge skills.

It was the perfect mix of what my brain needed to stay engaged — personal skills, rationality and a lot of technical know-how.

And the rest as they say is history. I now am in a job I loved, and after I GOT IT, I quit, started freelancing and quadrupled my income after 2 years of working.

If you could have a gigantic billboard anywhere with anything on it — metaphorically speaking, getting a message out to millions or billions — what would it say and why? It could be a few words or a paragraph. (If helpful, it can be someone else’s quote: Are there any quotes you think of often or live your life by?)

This one is my favourite. Hands down. J.J. Watt is a BOSS.

I don’t even know who he is but I am guessing a freakishly successful footballer.

Still have a burning question?

You can ask any question using the form here and all of my previous Ask Sherry posts are here.


  • Mia

    JJ Watt is one of the best defensive players in the NFL. But he’s also known for his charity work. He raised over 30 million for hurricane relief in Houston, paid for the funerals of mass shooting victims, shows up at children’s hospitals and to surprise fans, etc. My friend is from his hometown and nobody has anything bad to say about him.

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