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.

Isn't there a website that picks your clothes out for you and you send back what you don't like? If you're not actively paying attention to fashion maybe outsource this one.

With clothes, make it cheap so if you make the wrong decision it's not a big deal.

Also recognize you're engaging in the sunk cost fallacy by keeping clothes you don't actually want, and you're making the world better by allowing it to go to an owner who would better appreciate it.

Some more concrete ideas:

1. thrift stores

2. clothes rentals

3. clothing swaps

4. Buy the cheap version of what you think you might like (if it exists) first before buying the expensive version

5. Don't make your entire wardrobe trendy clothes. Make most of it relatively classic / basic and limit "trendy" to a subset of items.

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

Not for all of us, though. For some, socializing is considerable pressure.

Right, trying and failing at socializing is not fun at all.

> 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.

For the same reason, if it weren't for digital cameras, I never would have taken enough pictures to become competent enough to enjoy photography.

I am also all ears about anyone chiming in with an effective way to deal with shopping problems. Sometimes, I've found that what it takes is Gemini to restate what I already knew to be the conclusion but without my mental processing of trying to falsify it (Gemini, unlike real humans, doesn’t get overloaded and shut down when I ask rapid-fire advice questions).

Writing that comment got me to try Zalando, instead of slowly mapping out and visiting every store in my city. Maybe I wasn’t trying correctly.

My friend also taught me to slowly gather an inspiration folder with things I like. I have one for clothing, home decor and art. It made my job much easier.

I have filled a shopping cart with clothes I have seen on others in the last few months. It wasn’t that hard. I was just set in my ways.

It is for me too, but in the end, practice made it so much easier. It took years and some guidance from a therapist, but it worked. “I want to meet more people” was one of those problems that took me year to properly work on.

I think that the core problem was similar: I was willing to make an effort, but did not have a clear idea of how to do it.

Well, happy it worked for you.

For me, I've taught myself to socialize, but it takes lots of masking to do so, which means lots of energy, and failures are pretty hard on me.

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.

Assuming you earn enough, throw money at your problems. Many problems can be solved, or made significantly easier by money.

Don't do the research yourself, pay a specialist instead. Missing a winter wardrobe? Find a personal stylist (okay, requires some research to find, but much less than finding fitting wardrobe yourself). They will guide the shopping process, the outcome is most likely better than what you can come up with even with weeks of research. Costs a pretty penny, might feel funny, but it's effective.

Not happy with your art? Get a personal tutor for drawing. Learning a language, but struggling with it? Tutor it is. Learning is so much faster with personalized feedback and accountability, a good tutor provides both.

But then don't I need to find the specialist?

I had unexpected amounts of fun at long multi-day raves. You get into altered mental states (even without substances) and don't have to talk to people but also you can.

What is Zalando, besides an island in Denmark?

One thing that helped me a lot was practicing in low-stakes situations. I started chatting up Uber drivers pretty consistently and learned a lot about just letting go in the moment. I was using rideshare for all my travel at the time, before the pan made me realize how vulnerable I was without a car. I don't get that practice anymore because taking Uber is much less frequent and I let the habit ossify.