A roadmap for the future of Prosebox in Site Updates

  • Sept. 12, 2018, 4:56 p.m.
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  • Public

Hey everyone,

I’ve been wanting to write this entry for a few months now, but between the server issues and starting an intense new job, it’s been hard to find the time.

But! I need a break, so today’s the day. Let’s talk about the roadmap I’ve put together for the next few years. Warning: this is a long one.

Prosebox users
First, in order to understand my thinking, I think it’s helpful to touch on site traffic.

Here’s a graph of PB traffic since the beginning:

(That gap in the middle is the redesign last year, unfortunately that turned off the data tracking for a bit)

Ok, let’s break this down. Today the number of users visiting the site monthly hovers around 11k. At our peak in September of 2014, we were twice that at 21k. Why the big drop? It’s hard to say. OD coming back didn’t help, but the drop seems very consistent over time. According to the numbers, we’ve been shedding about 500 users a month since the peak.

There’s some good news here though. With the disclaimer that I only have a few months of data for this year, that 11k number seems to be holding steady. On top of that, it’s important to touch on those of you using the site. Around twelve hundred of you are posting or commenting every month. That sounds low, but it’s actually really impressive! Based on my experience with other communities, the usual number hovers around 4% of the total user base. Prosebox users, unsurprisingly, are very passionate.

Now, let’s talk financials
Also factoring into my long-term thinking, of course, is our revenue streams. Keeping the lights on is great, and we’re there, but I want to build out new features (and fix some old ones) to make this site better for all of you. That, as I’ve touched on before, costs money because I have to hire developers.

First up, ad revenue.
I posted a site update back in May about the declining ad revenue on the site and the steps I’ve been taking to improve that. I have a few months of data now, so let’s take a look.

The graph back then looked like this:
back den

And here’s how it looks today:
two dey

Not too shabby! Placing an ad unit on the sidebar and the front page has grown things considerably. We’re still at around a third of where things were at the peak in 2015, but considering the number of users we have has been cut in half I feel pretty good about where things are.

The Fundraiser
As I mentioned back when we ran the fundraiser, the money raised has gone into a “rainy day fund” to take care of any server and stability issues. Despite the ongoing problems we’ve been seeing over the last few months, the developers I’ve brought on board to fix things have been generously flexible in terms of what they’re billing. On top of that, I’ve been calling in favors all over the place with coworkers past and present to pitch in on things. It really does take a village. All that said, the PB rainy day fund is looking good for now, and I think we’ll be solid through the end of the year. Maybe we do a yearly rainy day fundraiser? Not sure just yet, we’ll see how things look next year and go from there.

Before I dig in, I want to say once again: There will always be a free and ad-supported version of Prosebox. No functionality that you have today will later be locked behind a paywall.

That being said, my current thinking is that there are two types of features I’d like to work on once we have the subscription infrastructure built and are generating revenue: paid features, and features that are available to everyone. Paid features will be things that are incredibly complex and time consuming to build or that cost money to operate. Unpaid features will be simple and convenient things or things that research shows will drive engagement (more about that below).

As for pricing, my current thinking (and as always this is up for discussion) is $4.99/month or $49.99/year. Yes, OD is a dollar cheaper. We’re better. The two features I’d like to roll out with subscriptions are entry search and image uploading (both very complex to build, and both suggested by all of you – great ideas guys!). I also want to build in the ability to “gift” a year or month of PB to another user.

Hate this idea? Let’s talk about it. None of it is set in stone, and it’ll be early next year before this rolls out. We have time.

How does building a new feature work?
Before I go into what direction I’d like to take the site, let’s talk about what that process actually looks like. It’s a lot more complicated than it seems. My dayjob is in product and user experience design, and while what that means can change almost daily, the process typically looks a bit like:

  • Propose a new feature based on detailed research about how users are using the site, and what will improve that experience
  • Identify the parts of the site that will be affected and need to be changed for this feature to be built
  • Design the feature (also based on research). This usually includes wireframes (mockups) and flow charts of every single variation
  • Help developers build the feature by writing out detailed specifications to supplement and explain the design
  • Make sure it’s built to specifications (it never is)
  • Keep an eye on user behavior after the feature is released to make sure the thing we built was in fact the Right Thing
  • Start the process over to make things even better

It’s a lot, and there’s a lot I’m skipping over here. If you ask anyone working in software they’ll tell you that the amount of effort for building anything is always 2-3 times more work than you originally think it’ll be. In short, new features are hard.

How do you decide what to work on?
The features that I’ll be building are based on a balance of feedback from all of you and research that I’ve done on the needs of the community. Sometimes a feature sounds like a great idea, but the usage numbers just don’t support that. A balance of the two helps point things in the right direction.

Based on my research, there are two things that could increase revenue: growth and engagement.

Growth means increasing the number of users we have on the site. I’m not interested in that right now. Honestly, a much much larger community would get unwieldy quickly and also, have you noticed the rest of the internet is super mean now? Nah.

So, that leaves engagement. And that’s a fun one! I want to build features that get all of you reading, writing, and commenting more. I want to come up with features that make you excited to come back to the site. With any luck that will not only increase ad revenue, it will increase the number of subscribers so I can fund the building of better features.

So, what’s on the list already?
Here is the current list of features on my roadmap for the next few years, presented in alphabetical order without comment or timeline. I’ve been listening, and most of these ideas came from all of you. There are a few of my own fun ideas sprinkled in as well. Oh, and if your favorite feature idea isn’t on this list, that doesn’t mean it’s not on my radar!

Unpaid features

  • Ability to sort front page by “new entries” or “most active in the past week”
  • Accessibility for seniors (set text size)
  • Auto-refresh front page when a new entry is posted
  • Auto-refresh notifications (comments and bookmarks)
  • Automated testing
  • “Circles” (name tbd) – writing groups of some kind
  • Comment editing
  • Entry flagging
  • Ignore User button
  • Writing Prompts (more on this later)

Premium features

  • Optional “Smart Feed” on front page (tbd)
  • Ad-free experience
  • Comment search (received and placed)
  • Entry Search
  • Entry Calendar
  • Image hosting and upload
  • Improved WYSIWYG editor
  • Organizing bookmarks/followed users into groups
  • Share entries only with specific groups of users

More soon!

PS: Mochi’s doing much better these days!


Last updated September 12, 2018

A Pedestrian Wandering September 12, 2018

Thanks for filling us in, this sounds well planned and interesting.

Gangleri September 12, 2018

Mochi is moving up in the world, yo.

girl in recession September 12, 2018

I love your updates 💜

Truly Me September 12, 2018

This makes me feel so happy. I'm so grateful we found you.

Serin September 12, 2018

I want the backup to include my comments. I think it's a premium feature.

a girl called s Serin ⋅ September 12, 2018

Great idea!

Flame is Love September 12, 2018

*holds out firstfuls of dollars*

Serin September 12, 2018

Oh. Also, is there any option to make a "back up all my crap" or "Check the books you want to back up" ?

Did I mention I like backups?

josh Serin ⋅ September 12, 2018

You can backup on the book level today if you go to your book and click the export button. Comment backup is an interesting idea, though tough to do right without thinking about the context. Hmm..

Serin josh ⋅ September 12, 2018

I know that. But I have to do that process for each book I want to back up, which disincents me to make use of the books or disincents me to make backups. The improvements to the system that you've brought make the exercise suck less, but back-all-up or back-some-up are more valuable than back-one-up repeated. And back-all-up has less interaction than back-some-up.

I can't speak to the challenge of the comment backup without knowing the underlying database. But given the backup is asynch anyway, it's within the realm of possibility to generate the comment backup in a loop through the entries. Which is why I recognize it smells like a premium feature.


josh Serin ⋅ September 12, 2018

Interesting! I didn't realize it was so cumbersome. This is really great info. The devs are looking into moving the export functionality off of the main server right now since it's such a hit on performance. Those things are definitely the features I'd like to make premium, because the more they're used, the more expensive hosting becomes every month. Gotta find that balance. Great suggestion, thanks!

Serin josh ⋅ September 12, 2018

And to make sure I finish on this rather important point , thank you (again) for the care you're putting into this place. I'm grateful that we're at a place where I can whine about shiny new things because we don't have to worry about the lights staying on.

Firebabe josh ⋅ September 13, 2018

I will pay you money if you make this a command button titled "Back Up All My Crap."

simple mind Firebabe ⋅ September 13, 2018

Back Up ALL My Shit


Firebabe simple mind ⋅ September 14, 2018

*high fives*

Flame is Love September 12, 2018

Aaaand what would I give for comment editing right now?

a girl called s September 12, 2018

I love all these ideas! I really do miss an entry calendar too, and I know that a lot of people are interested in a search function.

$49.99 is totally reasonable for a yearly subscription, and I would gladly pay it!

I too am very grateful that we have you!

ConnieK September 12, 2018

Will welcome the image hosting. Glad your pup is better.

TellTaleHeart September 12, 2018

Yes, OD is a dollar cheaper. We’re better.

Hahaha... damn straight!

The Thirsty Oriental TellTaleHeart ⋅ September 12, 2018


gattaca September 12, 2018

You are indeed better than OD. 😀

J🌞DI September 12, 2018

I like it but I don't see customized backgrounds on the premium list. Would we be able to do that as well like we can on Blogger?

GypsyWynd September 12, 2018

Image hosting, yes! I'd love to be able to change background and fonts, too.
Mochi looks very dapper in his tie. Nougat sends smooches💕

Deleted user September 12, 2018

It all sounds good including the subscription price . Hugs to Moochi !

Coddiwomple September 12, 2018

Mochi could be on the cover of Doggie GQ!
Thanks for all your work. Obviously you think about us a lot! LOL

Lis September 12, 2018


Teflon Superhero September 12, 2018

I see a lot of people suggesting customization options. So I'd like to add in there if that ever ends up on the radar, for the love of baby Buddha, please have the option to be able to turn it off for some viewers. I love customization a lot, I really do. But the biggest issue is that I'm colorblind. Not SEVERELY like many, but enough that in gaming I hope the game has a colorblind setting so I can manage to be able to play. A lot of times on OD, I wouldn't realize an entry had text, or could barely make it out and would have to highlight the pages to read it and it got tiring to have to select and go back up and read, and accidentally click and have to start over or figure out where I was to re-highlight.
So, some colorblind friendliness! Or maybe have it in the "Accessibility" note. A basic scheme/contrast/night mode sort of thing that could be used.
Other than that, I'm ready to pay!
And on the working the bugs out, I'm so happy the site is running faster. The only slowdown I've noticed is when selecting "all' under the bookmark pull down, it tends to hang up. I don't hardly use it, but sometimes I start an entry and have to leave it and since it removes from the list, I use the 'all' function to try and find that entry again.

woman in the moon Teflon Superhero ⋅ September 12, 2018

I use Bookmarks Latest instead of Bookmarks All when I want to go back to an entry I've already opened.

Teflon Superhero woman in the moon ⋅ September 12, 2018

Oh sweet! Thanks for the tip! I'll use that instead :D

WeAreStarStuff Teflon Superhero ⋅ September 13, 2018

I’ll use the mark as unread option (I think then icon is an eye) when I start reading an entry and then need to come back to it later.

Teflon Superhero WeAreStarStuff ⋅ September 13, 2018

I need to remember to do that. I usually start reading on my phone at work while on my breaks, then pick back up at my computer when I get home. I squeeze in as much as I can then hit the home button, then I'm like "no wait...dang it!" haha

Naiad September 12, 2018

Yeaaaaaaahh! (If you heard that as The Who then we can be friends.) I'm so here for all this.

The Thirsty Oriental September 12, 2018

Please take my damn money

patrisha September 12, 2018

"I also want to build in the ability to “gift” a year or month of PB to another user." Yes, please!

hugadog September 12, 2018

I never got around to welcoming you, Josh: Welcome! You're doing great.

Also, Mochi looks extra spiffy in his tie. Give him a scritch for me, please.

rhizome September 12, 2018

mochi looks so dapper! <3

Deleted user September 12, 2018

For those who can't afford to pay I wish there were a third option for us like more ads or something else where we can still get the premium features while contributing.

Jlynnaz 🌸 September 12, 2018

Ooooh entry tags would be rad. Don't know how much "fun" that entails, but I do find interest in how many times I mention "hubby" and the like in various parts of my journal.

oooooooh Mochi is adorable!!! I just want to love on him!!!!!!

I need tea. September 12, 2018

Thanks for all your hard work. It truly is appreciated. X

Marg September 12, 2018

I love that we're a passionate lot! Your list of premium features gets me excited just reading it - I would gladly pay that amount a year for all of those. When it comes to OD and Prosebox there IS no comparison.
And just when I thought Mochi couldn't get any cuter you smash that thought right out of the ballpark!

history of love September 13, 2018

Suddenly that team of developers looks suspiciously like it could be Mochi since e us dressed for work...;)
(I know they are really real)

Camdengirl September 13, 2018

They have days for everything so why not International Prosebox Day? I must admit part of the downfall of diary sites is that they are dirty little secrets - I never tell anyone about mine, and I want it to stay that way!

But certainly there are enough OD Liferaft/PB groups elsewhere that we can all remind everyone to chuck some cash in the pot...

kmh. September 13, 2018

Wonderful! Thank you. Definitely a reasonable price that I will be happy to pay.
"Yes, OD is a dollar cheaper. We’re better." is the sentence of the entry 😂

SarahBeth September 13, 2018

Mochi looks very dapper! I'm glad to hear that he's feeling better!

Thank you for the involved update! <3

Oyoa September 13, 2018

This is epic - so first off, hats off to you. (You are probably amazing at your job which makes sense as to why you are so good at what you do! My goodness gracious!)

Thank you for all the effort you put in. I generally stay quite buuuuut I realized I couldn't stay silent forever. XD

A lot of this sounds interesting! I would forever be a free-er (I don't write enough to justify paying nor do I do much...) but I think you are being fair for everything. Again... applause

Comment editing... Comment editing? I can see the appeal, for sure. Thanks for the updates!

Lyn September 13, 2018

Bravo! Thank you. 👍

Firebabe September 13, 2018

Okay, first, "Yes, OD is a dollar cheaper. We’re better," needs to be on a mug, or a bumper sticker or something.

Second, "Make sure it’s built to specifications (it never is)" legit made me laugh out loud. TRUTH, BROTHER.

Thirdly, my husband is really digging Mochi's tie and would like to know where he got it. LOL.

Fourthly, I cannot say enough how appreciative I am of how much work, and actual thought you've put into keeping our happy little family here afloat. I've worked in / around tech development most of my career, and as someone whose been a PM on projects with A LOT of stakeholders (i.e. the tenth circle of hell), you have my deepest gratitude for the level of effort being put in here.

Park Row Fallout September 13, 2018

Dude, your transparency in this process is so commendable! Thank you for that. It really shows that you appreciate that this is a community... it isn't a Site Master dictating the world to peons but a Community Organizer working with the community to create a better and better space. Thanks for that.

josh Park Row Fallout ⋅ September 13, 2018

My pleasure!

Astra Park Row Fallout ⋅ September 14, 2018

Third this.

summertime sadness. September 13, 2018

I don't care about anything else now that Mochi is wearing a tie. Pets in business attire is my weakness. NOTHING ELSE MATTERS, HE IS A BUSINESS EXECUTIVE.

sassafras September 13, 2018

Take my money! Dividing friends lists into groups that would have varying levels of access is my #1.

Thanks for all you do, J. :)

raeven September 13, 2018

I will happily pay. Love it. Please. Just don't go away.

Purple Dawn September 13, 2018

Image hosting! I'd happily pay!!

sparkli September 13, 2018

"Make sure it’s built to specifications (it never is)" -- truer words have never been said. :D

i missed the last fundraiser because i was on vacation but im definitely down for a yearly raid on our wallets and i'll pay you my 50$ (or whatever) as soon as you put up the subscribe button! :)

also this reminded me to turn ad block off for this website.

also again... thank youuuuuuuuu!!

simple mind September 13, 2018

We're better.

Damn straight, sir!

7puddingcups September 14, 2018

I loved reading this essay, and the comments. I actually just stayed at work twenty minutes after I could have left in order to read all the way through. I would love to see image hosting here, and would be happy to pay for it, as well as the other proposed features. Thank you for all of the thought and work that you put into this site.

josh September 14, 2018 (edited September 14, 2018)



kansasgirl josh ⋅ September 14, 2018

Are you testing comment editing?! Did I just get here at the right time?

josh kansasgirl ⋅ September 14, 2018

Haha! Guilty

Bullwinkle6 September 15, 2018

All great ideas!

LachrymoseBeauty September 16, 2018

Thank you thank you thank you! I love it! Consider me a future subscriber.

My two cents on improved WYSIWYG box: It needs a spell checker, and basic formatting options, but the feature I'd kill for would be the ability to add my own HTML formatting in the box. That would make me a lifetime PBer for sure.

Speaking of which... lifetime subscription offer? Is that a thing that might be able to happen, at least initially for some of us early to subscribe people who have stuck around through all this renovation? That'd be super awesome! I have trouble keeping up with recurring Bill's and would probably still be willing to pay for add ins and such as they come out. Anyone else feel me?

Exhumed By Scrying Eyes September 16, 2018

Mochi is looking good and awesome detailed update! Thank you.

One feature that I think should be available to all that would increase engagement (both in reading and writing) is entry formatting.

Whether you are writing new or c/p from another site or word, having your entry keep its formatting or being able to use formatting makes entries more easy to read, helps with outlines, bullet points, poetry and so forth.

The real me September 16, 2018

Thankfull for my OD lifetime subscription

Honestleigh September 18, 2018

You will get my money too.... Any reader's choice or spotlight to bring those really good writings forward?

Mooooochhhhi. Omg. A tie! Love it.

Deleted user September 20, 2018

I gotta say, I have always liked prosebox better then OD. I am excited about the updated futures to come. Keep up the good work.

Deleted user September 27, 2018

You know how there’s a little arrow that takes you back to the top of the page? Can we get one that can take you to the bottom of the page? Save us scrolling forever to get to the comments or the bottom of the comments. Or something like that at least :)

king of i October 07, 2018 (edited October 07, 2018)


So when we content creators curse y’all UX folks, we really should blame the engineers?

(I’ll stop cursing the UX folks. For this week.)

Fascinating ideas. I don’t engage for a few reasons, mainly because my attention span is 0 anymore. The biggest thing that would make me engage more is more content. At its best (which was many years ago) OD kept me coming back because new content was constant, at all hours of the day. It’s a chicken-and-egg thing, I know, just saying.

Good luck.

Caty Shark October 20, 2018

You had me at image host

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