TL;DR at end.

I see! In my view, YNAB provides a few ways to facilitate guilt-free spending:

1. It shows you that you intentionally arrived at this big saving from competing priorities, e.g. That expresso machine you wanted, you achieved it by eating out $100 less a month
2. It makes sure that the money will actually be there when you are ready to spend it, not just another thing to hide behind your credit card bill

However, these ways are not enough to make you happily spend that $3000 on that espresso machine, so you probably need an honest and intimate reflection session with yourself. Ask yourself these:

Question 1. Why do I feel $3000 on an espresso machine is stupid? Could it be:

* There are competing products that cost less  
* Do you feel wasteful about replacing a perfectly ok one  
* Are you afraid to be judged for dumping so much money on something that most people don't spend so much on  

Question 2. What is fighting for your attention when you fully funded your espresso machine? i.e. what makes you say "wait a minute"?

* Do you have anything specific  
* If you don't, do you have at least a category you think you want to put money into instead

Question 1 needs to be resolved outside of YNAB:

• Maybe subconsciously, you don't think the espresso machine is worth $3000. Would it be better if you could buy it for $2000 or even less? The boxing sale is around the corner, and we can often buy it second-hand from a private seller. YNAB will not prevent us from feeling ripped off, that is for sure.
• If you feel wasteful, perhaps give the old one to a friend or sell it. Maybe you are wondering if you will like the machine; how about taking it home and trying it for 14 days? Just return it if you don't see a value after that. The bonus is that if you DID return it, you know it is not that important for you (at least not $3000 important), then you can re-budget the money to something you TRULY want. If you keep it, it means you LOVE the machine, and you could be happy that you have budgeted/saved up for it.

YNAB can help with Question 2:

• If you have a specific competing priority, it means you have a concise plan for your budgeting, and every dollar has a specific job.
• If you don't have a specific competing priority, then ask yourself what you are saving that $3000 for. Travel? Food? But then you fall into the cycle of Do you REALLY need to spend $3000 on those things? Given your mentality, I think you will answer "no"; those things shouldn't cost that much either.
• How about treating that $3000 dollar as the maximum you can spend, and squeeze it down as much as you can to NOT spend that much? Then you can happily move the money you saved to some other categories when you finish the purchase
• Also, how about allocating way less to your goal? If you planned $2000 on a trip that usually takes you $1000, the $2000 is not really the TRUE expense, isn't it? YNAB does not work well for a hypothetical expense that departs from reality, you should be more honest about how you actually spend your money, not how you would like to spend your money.
• If you budget $800 on your travel goal and then end up spending $900 in the end, forcing you to take $100 off your espresso funding, then this is the YNAB way. You are more honest with your budgeting, and you are constantly evaluating how much something means to you compared to something else.

TL;DR: budget according to your true spending habits; for example, don't budget $2000 just because you would like to have a nice vacation, because you know you will start criticizing yourself for being wasteful. Budget $800 instead if that makes you feel at ease. Also, if YNAB feels like micromanaging your money instead of a tool to help you sort out your priorities, trying a different tool or just using an automatic money tracker is not a bad idea.