Learn Hardcore Portuguese (Portugal): Eu fico chateado comigo próprio quando não cumpro o meu plano. - I get annoyed with myself when I don’t follow my plan.

ficar chateado = to get / become upset, or to end up upset (focus on the change of state).
estar chateado = to be upset (focus on the current state, not on how you got there).

In this sentence, the idea is: I get upset with myself when I don’t stick to my plan (a reaction each time it happens), so ficar is the natural choice.

If you said Eu estou chateado comigo próprio quando não cumpro o meu plano, it would sound odd, as if you are describing a permanent state that exists specifically when you don’t keep to your plan, instead of a reaction that happens at that moment.

What exactly does chateado mean in European Portuguese? Is it more like upset, annoyed, or angry?

In European Portuguese:

chateado usually means annoyed, irritated, or a bit upset.
It can be emotional (disappointed, bothered) or practical (inconvenienced).

It is generally weaker than being properly angry (zangado):

estou chateado → I’m annoyed / I’m a bit upset.
estou zangado → I’m angry.

In this sentence, fico chateado comigo próprio suggests a mild–to–moderate self-directed frustration, not full-on rage at yourself.

How would the sentence change if the speaker is female, or if it’s plural?

The adjective chateado must agree in gender and number with the subject:

Male speaker (singular):
Eu fico chateado comigo próprio quando não cumpro o meu plano.
Female speaker (singular):
Eu fico chateada comigo própria quando não cumpro o meu plano.
Mixed or all-male group (plural we):
Nós ficamos chateados connosco próprios quando não cumprimos o nosso plano.
All-female group (plural we):
Nós ficamos chateadas connosco próprias quando não cumprimos o nosso plano.

Notice how chateado / chateada / chateados / chateadas and próprio / própria / próprios / próprias change to match the subject.

What does comigo próprio literally mean, and why use it instead of just comigo?

Literally:

comigo = with me
próprio = own / oneself
comigo próprio ≈ with myself

You can say fico chateado comigo and it’s understandable, but:

comigo próprio makes it explicit that the annoyance is directed at yourself, not just involving yourself.
It’s the natural, idiomatic way in Portuguese to say with myself in this kind of sentence.

So:

fico chateado comigo → I’m annoyed with me (a bit vague, less usual).
fico chateado comigo próprio → I’m annoyed with myself (clear and idiomatic).

What’s the difference between comigo próprio, comigo mesmo, and a mim próprio?

All three can refer to myself, but with slightly different flavours:

comigo próprio – very standard and common.
- Fico chateado comigo próprio.
comigo mesmo – also common, often a bit more emphatic or colloquial.
- Fico mesmo chateado comigo mesmo. (I’m really annoyed with myself.)
a mim próprio – more formal or emphatic, and often used with verbs that take a:
- Culpo-me a mim próprio. (I blame myself.)

In this exact sentence, comigo próprio or comigo mesmo would both be natural in European Portuguese. A mim próprio would be unusual after fico chateado.

Why don’t we use a reflexive pronoun like me with fico, as in fico-me chateado?

In Portuguese, ficar here is not reflexive; it’s just linking subject + state:

Eu fico chateado = I become / get upset.

You only use a reflexive pronoun when the subject performs an action on itself:

Eu magoo-me. = I hurt myself.
Eu culpo-me. = I blame myself.

Here you’re not doing an action to yourself; you’re ending up in a state (upset). The self-directed part is expressed with the prepositional phrase comigo próprio (with myself), so:

Correct: Eu fico chateado comigo próprio.
Incorrect: *Eu fico-me chateado comigo próprio. (ungrammatical in this meaning)

Why is the negative placed as não cumpro? Could I say eu não cumpro? Is não eu cumpro possible?

The normal negative pattern is:

não + verb

So:

não cumpro = I do not keep / follow.
eu não cumpro is also fine and very common; it just explicitly states the subject (eu).

What you cannot say is *não eu cumpro. The Portuguese negative não comes directly before the conjugated verb, not before the subject pronoun.

What does cumprir mean with plano here, and how is it different from verbs like fazer or seguir?

In this sentence:

cumprir um plano ≈ to stick to / keep / follow a plan, in the sense of doing what you had planned, fulfilling the commitment.

Comparison:

cumprir o meu plano → to honour / keep / carry out my plan.
seguir o meu plano → to follow my plan (more about following steps).
fazer o meu plano → usually means to make / create my plan, not to stick to it.

So não cumpro o meu plano is specifically about not living up to what you had decided, not about failing to write a plan or physically follow someone.

Why is it o meu plano instead of just meu plano?

In European Portuguese, it is very common and natural to use a definite article with possessives:

o meu plano
a minha casa
os meus livros

You can sometimes omit the article (meu plano), but in Portugal that often sounds more formal, stylised, or influenced by Brazilian usage.

So:

não cumpro o meu plano is the default, everyday choice in European Portuguese.
não cumpro meu plano is grammatically possible, but less natural in most casual contexts in Portugal.

Why is the present tense used in quando não cumpro o meu plano to talk about a repeated situation?

Portuguese uses the simple present for:

general truths / habits / repeated situations, and
future situations introduced by words like quando.

Here, quando não cumpro o meu plano means:

Whenever I don’t stick to my plan (every time that happens).

You don’t need a special tense like “I will get upset when I don’t stick to my plan”; the simple present (fico / cumpro) already carries that habitual or conditional sense in Portuguese.

Can I drop the eu and just say Fico chateado comigo próprio quando não cumpro o meu plano?

Yes. In Portuguese, subject pronouns are often omitted because the verb ending already shows the person:

Fico chateado comigo próprio quando não cumpro o meu plano.

This is perfectly natural and maybe even more common in speech than including eu.

You’d keep eu when you want to:

emphasise I (contrast with others):
- Eu fico chateado, mas eles não.
or when the context is ambiguous and you want to be extra clear.

Are there more informal or alternative ways to express the same idea in European Portuguese?

Yes, for example:

Fico lixado comigo próprio quando não sigo o meu plano.
- fico lixado is slangier, stronger: something like I get really pissed off with myself.
Fico mesmo chateado comigo quando não cumpro o que planeei.
- mesmo adds emphasis: I get really upset with myself when I don’t do what I planned.

The original sentence is neutral and natural; these variants change the register (more informal) or the strength of the emotion.