Wow, what a great thread. Love all the advice. This topic really resonates with me. I totally empathize with you in your compulsion to shop for clothes. Your shopping habits mimic mine from a few years back. Most of the advice read here I had to implement to overcome this horrible habit. I've spent three years working on spending. I make north of your income by quite a bit, I am married and we have rentals that DH handles so we have another big chunk of income there. THEN to top it all off, I also run multiple side gigs earning good money from those. I have NO debt but 4 mortgages. I did not have a hair on fire emergency as in your situation but the wastefulness of my spending was just so out of control.
So, in a nutshell, this horrible habit of mine had to stop. I had to get into my head, like really, really understand that by spending oh 2k a month on "stuff", it could be clothing, horse equipment whatever was NOT helping me meet my FI goal at all! If I really thought I was ever going to be able to retire on a conservative fixed income I needed to cut the spending cord. (I realize that is not your goal, but for each of us the reason to STOP is our own)
Each year after finding MMM I would join the "Buy no new clothes in xxxx year" - I want you to STRONGLY consider making a serious go at that. You can set your exclusions to things like undergarments etc. I FINALLY after three years am going to (just about) make this goal.
I have SOOOO many nice clothes, there is absolutely no reason for me to have more. I did not need to cut up my CCs, but did unsubscribe to EVERY SINGLE horse, clothing, jewelry, newsletter, sales emails etc. I just cannot see them at all, I cannot go to the websites or I will fail. I know it.
So, as part of my process to throttle back, and perhaps in your case you can use it to ramp back up, slowly. In 2013 I shopped at ebay. As a seller, I needed to get my ranking high, as high as possible to encourage buyers to choose my products over others. I used this as my logic to continue to buy vast amounts of things. Because I am a seller, I did allow spending what money i'd earned (akin to your idea of dog walking) I would buy a name brand sweater for $8 total and it would be a $60 value surprise in the mail. I still felt like I was over spending, even doing that - that was two years ago. I did finally get my ebay account to my goal. Whew. I am very goal oriented, money has never been an issue, it is still a matter of when is too much, too much! At that point I was able to buckle down and halt all of that.
Another curse I had to deal with is 30 years worth of clothes. I cannot imagine your closet! I don't typically wear my clothes out and I haven't gained much weight over the years so our entire walk-in closet was FILLED with my clothes. As phase 2 of no clothing shopping. I purged that closet and boy did that feel awesome. How can one person even think that they can wear 60 pairs of jeans? Really? I donated 12 hefty bags of perfectly good clothes that I could easily have listed on ebay (just thinking of the work that would have been gives me a headache). Instead I donated to a local horse club who got credit for the clothing to get cash back for a year end saddle. All that clothing was then in turn donated to local charities, so it was a double win.
So, How have I done this year on my "almost" buying NO clothing for the entire year? I have bought only one single clothing item. period. It was a Columbia fleece jacket at a company sponsored baseball game and I had $20 in reward tickets. I could not bring myself to buy food, what a waste that would have been. so I bought a $60 jacket for $40. It was something missing from my wardrobe and I don't regret it.
I've given up alot the last few years, but not because of money, I suffered a major back injury so I need to pop that in here. It was serious and very scary and that injury helped propel me to dive into finances. At one point I wondered if I would be forced to go on Disability and that terrified me.
As a result of all the changes in my life in the last three years as well as me and my DH diligently focusing on becoming FI. We are now looking at my RE date in January 2017. January 2016 (yes less than a month from now) We will begin to LIVE on our rental income. My income is going to be socked away for one last rental, and a couple of other life changing purchases that will propel us in to RE.
Without overcoming a severe spending habit, FI would not have been so close on my horizon. The strange thing is to non-MMM folks my spending is/was the norm.
I hope you do start a journal, and join the "buy no new clothes in 2016" thread when it starts.
You CAN AND WILL do this! I cannot wait to see your CC debt at 0!