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A stream enterer loses the first three fetters: personality view/belief in a personal entity, belief in rites and rituals, and doubt in the Buddha's teachings.
Yes. And it's possible to go further than stream entry in this lifetime.
You can become a stream enterer while being married, having a job, and living as a lay person. You don't need to become a monk. However, you do need to live differently than a regular lay person. You need to keep at least the five precepts and practice the Noble Eightfold Path. Observing uposatha was highly praised by the Buddha.
Yes. You can work a job and become a stream enterer.
This is tricky. It's very easy to think you're a stream winner when you aren't. A sotapanna is a person with Right View. They understand Dependent Origination and The Four Noble Truths. Stream entry is not a "black out" or some funky druglike experience. MN 48 goes into some of the behaviors of stream winners. The suttas in SN 25.* and MN 9 go into Right View, which is the specific knowledge of stream winners.
The instructions is the Noble Eightfold Path. Also read MN 117
On Teachers:
Someone telling you they're enlightened probably means they aren't, especially if the teacher is a monk as that violates the Vinaya (monastic code).
It's safest to only learn from monastics. Since they are bound by the Vinaya (monastic code) it's easier to avoid bad teachers. Make sure your teacher(s) has/have good ethics. The Vinaya (monastic laws) can be a bit tricky to understand, but it's easy to know if someone follows the five precepts. You want to learn from someone with perfect or near perfect following of the five precepts.
I suggest learning from monks, not lay people. Monks are a safer choice. Good monks have committed their life to the Dhamma and have no financial conflicts. Good monks are not paid; they do not have an income. Financial donations should be handled by lay people on the monasteries behalf. Both cash and a credit cards are money. Money is the ability to buy whatever the monk wants, instead of accepting what the lay community gives. If you ever run across someone who teaches something obviously wrong like "arahants have sex" or "I can drink alcohol because I'm enlightened" run away.
Be safe. Trust yourself. Bad teachers are dangerous. If you notice something is harming you, stop! It is possible to have serious and long lasting problems from practicing too hard or in the wrong way, such as damaged knees or a mental breakdown. It's better to be cautious than risk having an injury.
What to know about the suttas:
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What fetters must be destroyed in order to reach the state of stream entry?
Sakkayaditthi (self view), Vicikiccha (doubt), Silabbataparamasa (wrongly grasped rites and rituals)
Is it possible to reach the state of stream entry in this very life? It is said possible, if one possess the relevant causes. (past merit, born wisdom, correct view, ardent practice etc.)
Do I need to renounce worldly life in order to reach stream entry? Can I keep functioning in society by earning bread, and paying my EMI and still reach stream entry?
Even after ordaining, it is not guaranteed. Being in a modern lay life it is considered unlikely by many people. (but nothing can be said surely about these matters)
Either way, the beginning of the practice is possible as a layman for sure.
How will I know that I have reached stream entry once I am there?
There are a series of wisdoms(nyanas) mentioned to be arisen before and after the stream entry. He is considered highly aware of it.
Is there a list of instructions that, once followed, will surely take me to the state of stream entry?
The classical path is extensively described in Visuddhimagga's chapter on Satta-visuddhi.
Are there any finer details that I need to be aware of start on the journey towards stream entry?
Visuddhimagga (the standard compendium of Tipitaka) elaborates finer details from the beginning of it. (details about required virtue, ascetic practices, required meditations, required analysis of mind and matter, gradual path of seven purifications)
I have been a Buddhist learner since almost a decade, I frequently visit the Buddhist monastery close by, worship the relics of the Buddha, profess my desire to cultivate mindfulness. I am asking the above questions as I have no clue on how to start the journey, how to sustain and how to share the same with my loved ones so that they too can enjoy the fruit and bliss?
I guess it is because you have not read Visuddhimagga which is the classically recommended book for meditators.
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Q: What fetters must be destroyed in order to reach the state of stream entry?
The fetters are self view or identity view, doubt and grasping at precepts and practices.
And which are the five lower fetters? Self-identity views, uncertainty, grasping at precepts & practices, sensual desire, & ill will.
AN 10.13
"In this community of monks there are monks who, with the wasting away of [the first] three fetters, are stream-winners, steadfast, never again destined for states of woe, headed for self-awakening: such are the monks in this community of monks.
MN 118
Q: Is it possible to reach the state of stream entry in this very life?
Yes, if one meets certain prerequisites.
Someone with five qualities is able to enter the sure path with regards to skillful qualities when listening to the true teaching. What five? They don’t disparage the talk, the speaker, or themselves. They’re wise, bright, and clever. They don’t think they know what they don’t know. Someone with these five qualities is able to enter the sure path with regards to skillful qualities when listening to the true teaching.”
AN 5.152
Someone with five qualities is able to enter the sure path with regards to skillful qualities when listening to the true teaching. What five? They don’t listen to the teaching bent only on putting it down. They don’t listen to the teaching with a hostile, fault-finding mind. They’re not antagonistic to the teacher, and not planning to attack them. They’re wise, bright, and clever. And they don’t think they know what they don’t know. Someone with these five qualities is able to enter the sure path with regards to skillful qualities when listening to the true teaching.”
AN 5.153
Also, one must not have committed the five incurable actions (AN 5.129).
"There are these five inhabitants of the states of deprivation, inhabitants of hell, who are in agony & incurable. Which five? One who has killed his/her mother, one who has killed his/her father, one who has killed an arahant, one who — with a corrupted mind — has caused the blood of a Tathagata to flow, and one who has caused a split in the Sangha. These are the five inhabitants of the states of deprivation, inhabitants of hell, who are in agony & incurable."
AN 5.129
Q: Do I need to renounce worldly life in order to reach stream entry?
No.
Lay followers can attain stream entry and higher levels of jhana. An example is Citta, the householder. You can read about him in SN 41.
“But how is a wise lay follower defined?”
“It’s when a lay follower is wise. They have the wisdom of arising and passing away which is noble, penetrative, and leads to the complete ending of suffering. Then they’re considered to be a wise lay follower.”
SN 55.37
But it's unlikely to go beyond stream entry as a lay person, except at their deathbed (see SN 55.54).
Q: Can I keep functioning in society by earning bread, and paying my EMI and still reach stream entry?
Yes, if one takes the right effort.
Q: How will I know that I have reached stream entry once I am there?
Please read "Is stream entry an unmistakeable experience?".
Q: Is there a list of instructions that, once followed, will surely take me to the state of stream entry?
AN 10.92 lists out the criteria for stream entry:
And also:
“Sāriputta, they speak of a ‘factor of stream-entry’. What is a factor of stream-entry?”
“Sir, the factors of stream-entry are associating with good people, listening to the true teaching, proper attention, and practicing in line with the teaching.”
SN 55.5
Please read "Into the Stream" by Ven. Thanissaro and also watch the YouTube video talk "Characteristics of a Sotapanna" (by Ven. Dhammavuddho).
The video talk discusses SN 55.5 in detail.