Why I’m Terrible At Spending Money And How I’m Going To (Try) Fix It

Lately, I’ve realized that I’m terrible at spending money.

It sounds like a weird issue (and I’m lucky to have it) but in some aspects, it is an issue. I’ve spent the last 10 years programming myself to save and be frugal. Make the smart decision now of delayed gratification so in the future I can enjoy the fruits of my labor. But when is the future? 20, 40, 60 years?

I may very well not be here when the time is right.

It’s made me realize that the time will never be right and I need to adjust my mindset toward money. Over the last couple of weeks, I have read articles that hit on this topic. Some argue you should die with zero and give you a blueprint to do that. While other studies show that people that have saved and invested over the years never actually draw down on the principal of their investments and instead live off the interest.

Their lifestyles adjust to the cost of living and they make it work.

I want to be in neither of these camps.

On the one hand, I want to leave a lasting legacy. Selfishly, I want to give a huge chunk of money away when I pass that goes towards making society better. I don’t know if selfishly is the right word but long story short I want it to be known that it came from my family. On the other hand, I want to enjoy anything and everything I can because when I’m gone I’m gone.

And not to be dramatic but that could very well be tomorrow, none of us know when our name will get called and that’s scary.

Back to being cheap and not talking about my death… I personally have 10 shirts that I rotate through most of these are 5+ years old. When my wife takes me shopping I just can’t stand the idea of spending money on clothes. This example isn’t about clothing because the same thought process encompasses anything that involves me spending money. I feel like I need to keep investing and continue to be frugal because “it will pay off”. In reality, it’s just not healthy.

So how can I fix this?

Well, my first thought is to just go spend some money on some random things that I’ve been thinking about or wanting for months. To be honest, I did this with a large purchase last week and it felt good but I also know this isn’t a long-term solution because there was still a sense of guilt as I paid. Again, that’s just not healthy.

What I think I’m going to do is resort back to breaking down my finances. I already do this once per month with Tiller Money but that just gives me a check-up on my spending and net worth. I need something more that says, “Hey, you have this much money you can go spend however you want guilt-free”. It sounds weird but having the validation from the math will ease my mind and make purchasing things that I normally wouldn’t feel okay.

I’ll put this together and share it but I thinking of breaking it down into 3 buckets.

The money we use to live life every day and long-term investments so we can retire.
Long-term investments that can be used for retirement but the ultimate goal is to leave a legacy with.
Guilt-free spending money

I know I can break all of this down in Tiller and forecast it out with some conservative growth rates to see where we’ll end up.

This will be a work in progress and I don’t want it to be something that gauges my happiness but I just need to find a way that makes me feel okay spending money. Life is meant to be enjoyed and while I’m having a great time if I can get rid of that small sense of guilt when handing over the credit card I think things we’ll improve just a bit more.

What do you think? Do you struggle with spending money as well?