One debate that you hear if you're listening to different sex therapy or coaching professionals is whether you should be goal-oriented with your orgasms to have bigger and better ones, or not care about whether you have one and just enjoy the ride whether you have an orgasm or not. You get people who are divided in their opinions and stay that way. My position is they both have their place.
Let's take the first one. Goal-orientation toward having orgasms as the first step and then having more of them in the same sex session, having bigger orgasms, different kinds of orgasms, and combining orgasms that erupt from two different epicenters. You can't attain these abilities consistently without goal orientation. Nothing gets done by human beings without having a goal and drive. If you want to quench your thirst, you have to set a goal to find water and another goal to get it into your body. When someone tells you to not be goal oriented, not worry about coming, and just enjoy the ride, then they just set a goal. That goal is to enjoy the ride. savor it all the way, which for many people is something they have to practice before they get good at it.
Let's say you can already orgasm and you hear about other forms of orgasm that are possible for your body and/or enhancements to what you can already do. If you don't understand how setting a goal in sex gets you what you want, you won't get it, or have to wish and dream till maybe you have sex with someone who can coincidentally get you there... but who has time and patience for that? I've heard some sex experts claim that if it's in the least bit more complex than the simplest forms of bringing about orgasm, then you shouldn't spend time pursuing those things and instead put that time to connecting with your partner. That statement reveals a weak understanding of what's possible in sexual pleasure.
Instead of putting yourself in a box, imagine what it would be like if you committed to improve your sexual skills and also spent time before or after connecting with your partner.
Then imagine what your sex life would be like after you and your partner mastered a method for a bigger orgasm for her/him because you devoted time and effort to that, then after bringing that big, hot orgasm into being, you get the strong connection and appreciation feelings toward each other because that big O (and the devotion it took to make it) was so amazing. That's when connection time or bonding time, also known as "intimacy" to a lot of sex ed professionals, spontaneously occurs because you're so appreciative to each other. Yes, there are exceptions where people have blocks to feeling appreciation and/or connecting/snuggling too-- which is another goal to work on. Appreciation-driven intimacy very often happens naturally after great sex. Not only the sex that just gets the juices flowing and the clothes off. I'm talking about all that plus the big O's and other big events leading to them for her and him.
So much sex happens where one person has those wow feelings and the other person is not so wowed. Many of my women clients say they enjoyed the closeness, how much they desired each other, and basic vaginal sexual pleasure, but had no orgasm or almost got there. There's nothing wrong with that, but that's bare minimum compared to what she could be getting. These clients say they feel something is missing and want more. That change doesn't happen without goals, without vision for what's possible, and then action to produce those results. You want development, not stagnation, because the brain gets bored with the same thing on its plate every time.
Now, let's look at when being too goal-oriented in sex is counterproductive. The most common one is the woman who has never had an orgasm and throughout her trip toward one, her mind is spinning with angst: "Will it happen this time? How do I know I'm on the right track? How long will this take? Will (my partner) get bored before I get there?" On and on. When the goal isn't reached, the failure angst sets in which makes sex look like work. That thinking is what sexperts are trying to stop when they say, "Don't be goal-oriented. It's about the trip, not the destination." They're absolutely right within that context. The problem is when some of them go too far and extend that directive to almost everything you approach in sex, or listeners to the advice logically decide to take that principle and apply it everywhere.
Set a goal and then enjoy the ride toward it no matter where the end point is. If you don't get your desired goal, look back on what you did create. Did something new happen that was better than the last time you drove toward the larger goal? That is a sign you're getting closer to it. In that case, you made progress and you had erotic fun doing it. When small successes aren't appearing, it's time to make some shifts and changes to what you're doing or having done to your body and mind. It's like adding a pinch of salt or a dash of spice to a dish to perfect it. Even if the first attempt isn't the ideal, don't give up. Don't allow the get-it-the-first-time conditioning enforced by our culture to mess with your head. There are times in sex where first-time success happens and others where you might as well expect to fly to the moon without a space shuttle.
We're living in a time that is better than it has been with regards to sex understanding. However, it is also a time that still has flawed sex beliefs firmly in place. One of the biggest is that you can't develop great sex. That you have to wait for it based on some romantic perfect person and it will auto-happen. Don't waste anymore of your life believing that. Instead, find a partner who wants to take the erotic journey with you. Set goals, get the skill sets you need to achieve it, and enjoy the ride. It gives you a good reason to be in love with the person who committed with you to creating incredible sex and orgasm.