Quote from Lucio Buffalmano on July 6, 2020, 11:24 am

One of the 48 Laws of Power says:

Despise the free lunch

And later Greene adds to always pay everything in full, and let your money circulate around.

He is right, in many ways.

Yet, it's also undeniable that money is a huge power tool.
Having money makes you freer, provides you a far greater degree of control over life and others, and also works as a powerful insurance policy against many possible unpredictable scenarios.

So, what's best?

Pay in full, and show your power by throwing money around, or ask for discounts and conserve power?

From a Machiavellian Perspective

From a purely amoral, power-maximizing perspective, this is the best approach:

Ask for discounts / haggle, when:

• You won't see the seller again (he is not part of your social circle / not in the same city / cannot spread rumors)
• The seller's goodwill is not important to the product's quality (he is selling ready-made items that need no future servicing)
• You're discussing bigger items purchases (the haggling makes the risk of looking cheap worth it)
• You can make up for that value with different currency-exchanges (here's something nobody acknowledges: if you're high-value and a high-power at a personal level, you're far more likely to get discounts simply for the pleasure of interacting with you)

Depending on the culture and whether or not haggling is expected, haggling -and almost always haggling too much- can make the seller dislike you, and makes you come across as a cheapo who is devaluing the product and the seller himself.

Haggling too hard also reduces the seller's margin, which impacts the seller's ability to live and provide for the people around him.
That can antagonize the seller, and is a relationship-risk that can carry future costs.

Outside of street sellers where you're suppoesd to spend some time, my policy is that I choose great professionals and only ask for discounts once or maximum twice.
More than that, you are offending a professional and you risk antagonizing them.
And I make sure to maintain goodwill and win-win frames.

For example:

Seller: So, the suit is going to be 2.000
Me: OK, could you make a little discount? (notice the use of "could", which makes him feel I am still assessing and he must will win my business)
Seller: Ehehe... Hmmm, I can make 10% off

I might stop here if the seller's goodwill is important to me, or if I'm liking what I see.
Otherwise, I might add:

Me: (smiling) OK, thank you. (pause, reflecting) Could you maybe make 20% if I like the product, become a good customer and talk well about you? (I add something more to the exchange to make it easier for him to give something more)

At that point, I usually stop.

Pay in full or add tips when:

•  The seller is part of your social circle / you will see him again
• You will need the seller again for support, questions, other favors
• The seller's goodwill can come in handy (you will go back there and his friendliness can get you served earlier, or provide you with social proof if you bring a date or business contacts)
• It's uncommon to negotiate (no matter what personal-finance authors say, negotiating meals at a restaurant yells "cheapo")

Negotiating too much can also have mindset consequences.
For example, you might internalize that you don't have enough, or that you must "fight" in life (and yes, sometimes you have to fight, but not always).

Pro Tip: Combine the two with long-term discounts

Another technique I like to use is to propose long-term discounts for repeat-transactions.

For example, you love a restaurant, or if you always to the same barber shops and they're both quite upscale, chances are they have high enough margins that they'd be happy to keep a long-term customers in exchange for a discount.

The trick then is to frame it as win-win, so you come across as value-adding instead of value-subtracting.

For example, after your first haircut at a barbershop you enjoyed:

You: hey man, I really liked your work you know. I just discovered this place and I think I might like to come back here more often (same persuasion as above: make it sound like you're still a customer to be won).
Would you be interested in making some kind of repeat-customer deal. Something like I always come here, talk to my friends about it, and we decide on a long-term pricing

You avoid calling it a "discount" since it's the first time you make the move, so you want to test the waters without exposing yourself too much.
See if he bites. If he does, great. If not, you tried -and without coming across as a cheapo-.

From an ethical point of view

From an ethical point of view, you wouldn't negotiate the price of an item that is already delivering great value to you.

Ethics is also not just about ethics, but also about effectiveness when you are dealing with people who value other people with similar ethics and values.

For example, if someone is trying to negotiate ThePowerMoves' products without valid reasons, then I usually don't reply because I see it as unethical behavior to offer discounts when someone else is paying the quoted price.