How do you try new things in your gameplay?

I look up sims challenges. They really help spice things up. Sometimes I'll even add extra rules to make it that much more interesting.

My current playthrough I've come up with a crazy apocalypse story/scenario that will limit what I am "allowed" to do. If you usually go the suburban family route, try being a bachelor/bachelorette for as long as possible or vise versa. Focus on a career that you've never done before or consider not having a career at all. If you usually play one gender and/or sexuality of sim try doing a different one. Do an alien or vampire sim if you have the stuff for it. I usually start off with just one sim, so those few times when I start off with multiple sims are a bit more interesting. Do different aspirations or traits that you usually ignore. Get into things you don't usually get into. Do you do a lot of mischief? Comedy? Have you done any music or writing careers? Have you discovered every collectible? I haven't for any of those. Find the aspect that you usually ignore and focus on it. See what happens.

I don't really do that. If the storyline pushes me into a certain direction then that's okay, but I do not go out of my way to leave my comfort zone.

The last time I deliberately tried something new was when my storyline required the main character to locate and recruit a sinner of some kind. The usual way would have been asking about career (criminal and secret agent/villain) and learning traits through conversation. But that one time I opted to put my sim into the police career instead and choose a criminal from the cells. Despite owning GT for some time I had never before played that career and ended up enjoying it quite a lot.

Or the time when I wanted a unicorn for my legacy family. I do not normally play with dogs, just cats. But user made unicorns are based on large dogs, so here I am playing a dog. It's okay while it lasts, but nowhere near the "wow, this is actually fun!" experience the police career was.

What I'm doing at the moment is (I have all aging turned off), and I am playing the whole town, and have created most of homeless in my game as well. I'm not playing rotational, but whom ever I feel like playing at the moment. My normal game play usually involves one single sim or household, doing the same thing over and over again, and this is why I'm trying something different.

I like to look at what other people are doing. It's such a big game that it's easy to forget stuff that you can do. Or not be as creative as you could be.

Someone said they were playing a character who was a nature photographer going to Selvadorada and I thought that was really creative and great.

I just like to try things off the beaten track.

I find challenges to be a great way of trying new things - The Murkland Challange really pushed some of my limits and made me appreciate the game in whole new ways.
Recently I have created my own project that requires me to do rotational play (I've never done that before) and have my Sims do stuff I would normally not try or "allow". I've always gone for "Picture Perfect" in my game - but I'm finding it a lot more fun to ruin that perfect picture these days :D

I like to have families with either generally happy lives or otherwise, to change that I've done random things with different stories either keeping with that idea or not. In order of the photos, just four.
1. A male alien under a scientist's protection fell for her and ended up pregnant when she wasn't sure about the idea he meant to ran away he was found and brought in to another holding facility a windowed room away from their child where she was allowed to visit.
2. The maid was in a sort of rags to riches sort of story but since she met Mila Munch and ended up the maid she was meant to prove she could make a living without her father's inheritance. Her evil stepmother only agreed to keep it going after he died as there was a iron clad contract protected by and old friend of her father's.
3. They were meant to have a family and only make a living off of collectibles found and things that mama dearest stole they raised six children in that little shack adding on bit by bit until they were all closed in. That legacy was a trail of bad decisions fun though.
4. The couple returning from a wedding, I cheated the blond to be related to Bjorn so the girls are his nieces he stepped in when Bjorn wouldn't be a part of their lives.
fun times.

I created my family to help me actually experience everything in this game, or I at least hope to. With every succeeding generation I try to complete a career and/or master a skill, and finish their chosen aspiration.

It’s a lot of work tho but I’ve been having fun this way.