Keep several failed attempts interesting by making each fail because of a different person's motives or assumptions.
Selected early and middle attempts to get arrested. The church scene and the ending are not described.
Winter is approaching, and Soapy sleeps on a park bench in New York. He wants three months in the prison on Blackwell's Island, where he expects food and a bed. He prefers that prospect to charitable lodging because he resents the personal questions and humiliations he associates with accepting charity. He sets out to commit a minor offence that will get him arrested.
Soapy first plans to eat at an expensive restaurant and announce that he cannot pay, but the staff see his worn trousers and shoes and turn him away before he reaches a table. Next he breaks a shop window and waits beside it. The arriving policeman assumes the culprit would have run and pursues a passing runner instead. At a cheaper restaurant, Soapy gets his meal, but the waiters throw him out rather than call the police. Later he takes a man's umbrella and invites the man to summon an officer. The man retreats, admitting that he himself picked the umbrella up in a restaurant. These are selected attempts from the story, not its full sequence.
Do not make every obstacle a coincidence or have every official ignore equally obvious evidence without a reason. The window scene gives the policeman a mistaken inference; the restaurant scenes show different ways staff control access and handle nonpayment. Soapy's opinion of charitable lodging is his perspective, not a universal fact about aid. The umbrella man's hesitant account suggests an insecure claim to the umbrella, but it does not establish its true owner.
The Cop and the Anthem, in The Four Million: the opening park-bench decision, the two restaurant scenes, the broken shop window and the umbrella encounter before the church scene. ↗
Complete English short story checked in Project Gutenberg ebook 2776. This card selects four attempts and does not summarize every incident or the ending. The account of how the failures differ is editorial analysis. The family-repair example is an original application, not a scene from O. Henry.
A character can choose an action without being able to control the response it needs. A manager may be trying to keep a business running, a witness may misunderstand what they see, or someone asked to complain may have reasons to avoid questions. Decide what each person wants before writing their response. One attempt can fail before it starts, another because an action is misread, and another because someone chooses a different solution. The constant goal gives readers a clear effort to follow, while these different causes change what the character must try next.
Write your character's goal, then the response they need from someone else. In an original example, an apprentice electrician wants his weekends free to spend with his daughter. An aunt housed him during his training, so he finds it hard to tell the family that he no longer wants their repair jobs. When he says he is busy, his aunt offers to wait until next weekend. He then gives an uncle a price quote, hoping the expense will put him off; the uncle offers to pay because he trusts him more than a stranger. One person has misunderstood his refusal, while the other has willingly met the condition he expected to end the request. He must now explain that money is not the problem and recommend another electrician. For your scene, give each unwanted response a different cause and let it expose what the character's next attempt must address.
Use in my storyMake a running joke develop: each attempt to get rid of a nuisance should inconvenience a different person in a different way.
Make another attempt more frightening by having the danger damage the very ability the character needs to escape it.
Let a threatened character infer a deadline from the preparations being made around them.