this is a very difficult question to answer. Because... things... are complex.
I guess the gist of it is "the reality where a good part of the tumblr community lives is not the same reality that staff experience". Mind you, I'm not saying that Staff is oblivious or uninformed. Kind of the opposite. Staff manages a big extra layer of data we the users don't get access too. Things from "how long we have to achieve X or close" to "this change had very bad feedback but didn't make the usage numbers go down and it's bringing 0.03% more revenue".
There's a hard reality we tumblr users who like tumblr as-it-is need to start accepting: We are not making tumblr make money, so we are not going to be the 'client' here.
While I was in staff, we tried. We tried hard: Post+, the merch store, blaze, ad-free ... all those were attempts to make tumblr a platform funded by its community. The results were ... not great. Like, two orders of magnitude worse than they needed to be. That let tumblr in the hands of advertising money (that even if tiny compared with other sites, it still is the main Tumblr source of money by far). And for that, if you want to make the site stop burning millions per month you need way more people than we tumblrinas are right now.
Mix that with.. a certain disdain for tumblr as a platform from part of the top management. A big bunch of staff are hard-core users of tumblr who are more or less in tune with the feelings of the community, but in the upper management layers... there's only one or two persons I can think of that actually seems to like and enjoy tumblr. The rest of them are mostly users of other platforms in their personal lives, and ... they just don't get why tumblr is so hooking for some of us. They don't understand how it works, they don't understand the popular content here, they don't understand the people who already use this place.
Earlier this year I actually had a call with the CEO to try to explain him why tumblr was a great platform for a certain type of mindsets, how I have adapted to this boiling cauldron of feral goblins so quickly and become enthralled by it when I started using it four years ago. And I think I failed completely at trying to make him excited or even interested in either the site culture or its community. Or convince him that tumblr could expand vertically (bringing more tumblr-minded people in) instead of horizontally (broad the appeal of tumblr for the masses even if it dilutes the current essence).
So for management, it's just a game of numbers: The current tumblr community doesn't cover the costs of running the site, so they need a new community that does. And if in the process, some of the old community leaves forever, :shrug:, not a big loss, since they weren't making the company any money anyway. It's more important for them to get all those people leaving twitter or other platforms to actually come here and stay, and get those key metrics up up and to the right. Of course, this is just my personal opinion and I'm sure if someone send this post to those in management who I'm vaguepostingly mentioning here, they would be all "Of course we CARE about our community and tumblr's history!". But hey, you know you really don't.
"But Javi, isn't alienating the core community who creates most of the content in this platform a stupid and terrible idea in the long term?". Why, dear anon, of course it is. Or that's what I think. And that's what I ended arguing about again and again and again and again while I was part of staff. And that's, maybe, one of the handful of recurrent points where I wasn't "aligned with the direction of the company" that made me un-staffed (take that, tiktok kids!).
Why, then why tumblr management keeps pushing for this pace of rapid and alienating changes? Because Automattic, tumblr owner, is a private funded company. And there has to be smoke and mirrors showing that tumblr is actually moving fast and making the numbers go up up up. Every. Fucking. Quarter.
Do you know what's the most stressing time of the year for your random staff member? Is it eurovision with its peaks of traffic? april's fools with all the tomfoolery? No. It's the biannual Automattic board meeting. Because in every. single. one. of. them. we didn't know if that was going to be the day where tumblr's downsizing would be greenlighted. Literally, every six months the board would look at what happened at tumblr and say "ok, this is terrible but moving in a promising way, let's see if these things you are planning work and re-evaluate in six months".
Does this mean they are in the wrong and me and the people pushing to keep tumblr more tumblr were right? Well, no. Not necessarily. Tumblr has been under a very real existential thread for ... at least a couple of years. And the reality is that 'trying to monetize tumblr as-is' didn't work at all from a purely economic point of view, and tumblr wouldn't have survived for much longer without showing clear gains. So who knows, maybe by diluting tumblr they could manage to make it profitable and keep this site live for decades. I would be VERY happy to be in the wrong here.
At the end of the day, put yourself in staff shoes. You have been trying a lot of "sensible" things to try to make Tumblr sustainable. Your boss is reminding you that tumblr keeps losing money and setting dates for "lines of no return" where the company would need to deinvest on Tumblr if there is not a clear financial improvement. You know you are burning the midnight oil and the sensible changes requested by the community you have made barely had put you closer to the goal. So it's time to try the crazy stuff and see what happens. Yeah, maybe that makes the boat explode, but maybe it changes it enough to keep it afloat. The alternative is letting it slowly sink into the darkness.
So, as I warned at the start of the post, this is a very complex issue with a lot of factors involved. And of course, this is just my particular view on it, I'm sure other ex-staff members would see it in a different way. Staff members need to keep their voices 'aligned with the direction' so they don't get un-staffed, but I can tell you that a good bunch of them are in private slack channels saying things like what I'm saying here (hello friends from #********* and #******-****!). Some of them like the X change but hate Y. Others don't really care and are just doing their job and doing what their boss told them (which is a completely valid stance... this is a job).
So yeah, it's complex. Believe me, a lot of folks in staff listen to what the community says. Deeply. But right now I don't think management thinks that catering to the current community is a valid path. And given the constraints of time and money that staff needs to operate within, I'm not even sure it matters much.