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Stopping breastfeeding is solely a mother's decision. It is up to her to decide what's better for her baby. There can be a bundle of personal reasons to take this decision: hectic work schedule, desire to get pregnant again, social pressure, sore nipples and pain in breasts because of breastfeeding, inability to produce enough milk, etc.
However, if the mother finds it painful to breastfeed her child, and still she wants to go ahead with it, it is much advisable to consult a breastfeeding health specialist. The doctor could have some practical information on ways to overcome these challenges. You can also be part of certain social forums where mothers discuss their common problems related to child and breastfeeding, and find proper encouragement and support from their side.
How To Know If It's The Best Time To Stop Breastfeeding?
There is no solid rule and timing about when to stop breastfeeding. As long as you and your child are happy with this process, there is no harm in continuing with it. Nevertheless, we can take a look at the duration when the toddler really requires all the benefits from mother's milk.
It is important to feed your toddler with just breast milk for the first six months. After this period, you can start by giving them soft solid foods that are easily digestible, along with breast milk. For entire one year, breast milk should stay the major source to provide nutrition and calories for your toddler. 
The baby will stay protected from diseases and infection, as long as it consumes breast milk, thanks to the numerous health benefits of mother's milk. Indeed, breast milk helps the toddler to easily digest its first solid food.
Once the decision has been made to stop breastfeeding, the changes should be brought in slowly. This gives the mother required time to produce less milk gradually; it also helps the kid to get well adjusted to bottles filled with formula milk.
The process of giving up breastfeeding can be an emotional ride. Where you might be happy to see your body retracting to its original figure, you may also start feeling sad about the end of the special bond with your child.
Let us take a look at ways to manage this transition and discomfort, and make the child used to the new routine of feeding.
When And How To Stop Breastfeeding
1. Provide proper nutrition for the baby
If the baby is less than one year and the mother decides to stop breastfeeding, it is still required to feed the baby with donor breast milk that has infant formula. Babies after 6 months can start feeding on their age-appropriate solid foods, yet they need the combination of iron-fortified milk as well. 
They might need solid foods that have sufficient iron, protein, nutrients and other antioxidants that provide them immunity. It would be advisable for the parents to consult a paediatrician, if they are concerned about the proper balanced diet of their baby and their ideal requirement of daily calories.
Babies should not be fed soy milk, cow's milk or any milk that is heavier in texture, when less than a year. They may also need some supplementation of vitamin D, iron or multivitamins, in case they are not getting enough.
2. Eliminate stress
Many toddlers easily pick on weaning, while others put a lot of fight and tears. It is better to plan things beforehand before jumping into this process. Also, it is more convenient to take things slow. It will be easier for the mother to set time aside when she does not have to deal with other stressful situations like pending work, vacation planning, etc.
The mother must focus on spending quality time with her baby, so that she could handle it effectively if it gets clingy or anxious during the weaning process. It is preferable to plan this few weeks prior, if the baby needs to be accustomed to the new routine by a certain date. The earlier everything starts, the better it is.
3. Choose night for weaning
Most babies have less hunger during the night between the age of 6 months and a year. Night weaning can prove to be a boon for the mother to get some rest and make the baby comfortable with another routine. 
This procedure of minimal night time feedings also helps the mother to recover comfortably and happily sustain breastfeeding sessions during the daytime.
4. Reduce breastfeeding duration
Breastfeeding should never be stopped in one go, no matter how tempting the idea may seem. Sudden quitting can cause pain in nipples. The breasts may become engorged with milk causing a lot of pain. There are possibilities for both mother and child to become psychologically stressed out. 
Stopping this process should be done over weeks, in a planned manner. The mother should pick a session where the baby is not very concerned with what it eats; it should not give much importance to that particular food routine. Let the baby get well adjusted to this change first, before switching into another modification in the feeding routine.
The same process should be repeated multiple times until the last breastfeeding session has been eliminated and the entire routine is in control. The last change, usually related to the morning and evening sessions of feeding, is the most difficult to cope with.
It is necessary for the mother to allow herself as well as the baby ample amount of time to adjust to this last obstacle. Let it happen gradually. Some mothers let this last stage continue for a few months, so that everything normalizes over time.
5. Use a pump
A woman produces milk in her body according to the demands and needs of the baby. If the baby feeds more number of times, the mother will have to pump regularly to supply milk.
The secretion of milk starts reducing over time, when the baby consumes less. This process can cause mild discomfort, swelling and breast pain in mothers. A good solution to lessen the pain is to pump breast milk in small quantities. However, this process should not be done more than 2-3 minutes, as it can start more milk production. Just a little pump to get rid of the pain should be fine.
The pumped milk can be given to the infants later in some feeding session. This is enabling the babies to get used to the weaning process, while also helping the mothers in shrinkage of their milk supply.
6. Managing engorged breasts
If somehow pumping of milk does not reduce breast pain, there are other ways to deal with this situation.
- Application of chilled cabbage leave over breasts can lessen the swelling discomfort.
Consumption of NSAID for engorgement.
- Application of cold compression bags, or steam bath.
- Discussion about intake of birth control pills with the doctor, as they are known to reduce milk supply and ease the weaning process.
- Breast massage to relieve plugged ducts.
- Wearing a support bra for comfort, as tight bras can cause infections and increase the swelling.
7. Keep an eye on trouble
Weaning can cause a lot of stress for the mother. It cannot be termed as dangerous, however, it involves the risks of malnutrition for the baby and contraction of breast infection. Mothers can even become depressed or anxious about their bonding with the baby, while the infant can start feeling insecure without breastfeeding. 
It is important to consult a doctor if the mother gets fever. If the breasts become red from swelling and there's greenish and foul odour discharge, it should be taken seriously. Also, if the baby doesn't pee or poop frequently and has developed an erratic sleep routine, something needs to be changed about weaning. 
8. Provide necessary love to the infant
Breast milk not only provides nutrition, but also helps to provide comfort and security to the infant when they feel scared and anxious. There are certain factors that need to be kept in mind, to make the weaning process easy for baby as well.
Hold the baby close to body while feeding food. Give them a pacifier if they start crying  . Sing a lullaby, play soothing songs, rock the baby a little to cheer them up. A teething ring should be given to the teething babies. Allow others to comfort and feed the baby as well.
Suppression Of Milk Supply
The mothers would want their milk to dry up once the baby has got used to weaning. It can be an exhausting journey, as the milk can clog and cause swelling. Breast pads are effective in soaking any leakage from breasts. Painkillers can be consumed on doctor's advice and cold gel packs can be slipped inside the bra for relief.
This process to stop breastfeeding requires patience. It is challenging initially for both mother and baby, but over months the situation improves.
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-  Pacifiers (soothers): A user's guide for parents. (2003). Paediatrics & child health, 8(8), 520-530.