Maybe you’re not trying

Great post!

I find that this happens when I want to do something The Right Way, but don’t have a clear path, nor the energy to figure one out.

For example I want a nice winter wardrobe, but first I have to figure out what I like, what is trendy, where to buy it, what will suit the weather. I am wholly unprepared for it. Suddenly it’s a whole ordeal, so I just wait.

In another category - art - I had to learn to be okay with suboptimal outcomes. Each attempt teaches you something, so to make good art, you have to make a lot of bad art first. Paper is cheap and making bad art is fun once you move past perfectionism.

Socialising is the same. You get better at it through practice. Practice is fun, it makes you do fun things and meet fun people.

With “shopping problems”, you are stuck with your bad purchases, your suboptimal wardrobe. Each iteration is expensive in time and money. So you try to get it right the first time. Cue weeks of research for something that is ultimately not that important. The worst is shopping problems that have an element of taste.

If someone knows a way to deal with this, I am listening.

I've found that thinking about complex problems as finding a way to enable iteration helps a lot. First off, anxiety-wise, it's much easier to think about the iteration rather than the bigger problem. And while working your way towards iteration, you also begin to tackle the bigger problem from different angles. That itself is valuable, but you also get a bit of much needed desensitization as well as some small victories which yield the mental resources to ultimately help you get yourself together.

I recently had a similar issue with the wardrobe. I've been bedridden for an extended period of time and lost a lot of weight in the process. As a result, I had to replace every basic piece of clothing, both indoors and outdoors - things either didn't fit or were too worn. I still didn't feel too good to go shopping around town so I had to order online. On top of that, I was short on money. With little room for error, the task felt daunting, to say the least. Couldn't get around it for a while.

Long story short, I solved the shopping problem by figuring out how to sell the old things first. That helped me with both getting the old pile of crap off my mind as well as moving forward with the new purchases without the fear of unrecoverable losses. Now purchasing clothes feels less like gambling and more like something I can be in control of. The stars don’t have to align the first time, but eventually, they will.