1. • Cushion Restructuring the individual project page

   • Cushion Project blocks

   • Cushion Redesigning the homepage

   • Cushion Multiple timelines

   • Cushion Archiving and estimate differences

   • Cushion Multiple financial goals

   • Cushion Zooming in on the timeline

   • Cushion Currency

   • Cushion Preferences, accounts, and typeface change

   • Cushion Sending out the first email

   • Cushion Currency inputs, notifications, and invoice nets

   • Cushion Dots and lines

   • Cushion Calculating in the database and revealing tendencies

   • Cushion Improved form UX

   • Cushion Cushion is online

   • Cushion Schedule timeline patterns

   • Cushion A slimmer schedule timeline

   • Cushion The schedule timeline

   • Cushion Plugging in real data for the first time

   • Cushion Transitions and project lists

   • Cushion Death to modals

   • Cushion The individual project page

   • Cushion Estimated incomes and talks with other freelancers

   • Cushion Statuses to lists and the paid beta

   • Cushion The timeline

   • Cushion Invoice terminology

   • Cushion Modal forms

   • Cushion Wiring the backend to the frontend

   • Cushion Balancing design and dev

   • Cushion Timecop, Monocle, and Vagrant

   • Cushion Going with Ruby and Sinatra

   • Cushion Ditching local-first and trying out Node.js

   • Cushion Switching to AngularJS

   • Cushion Building the Table with Vue.js

   • Cushion Clients, Projects, and Invoices

   • Cushion Introduction (to the Cushion journal)

   • Cushion Cushion

   2014

2. • Cushion Retention through useful features

   • Cushion The onboarding checklist

   • Cushion Spreading the word

   • Cushion From beta to launch - the subdomain

   • Cushion From beta to launch - sign up

   • Cushion From beta to launch - messaging

   • Cushion Launch

   • Cushion Authenticating with 3rd party services

   • Cushion Intro to integrations

   • Cushion Inspiration vs imitation

   • Cushion The emotional rollercoaster

   • Cushion Designing project blocks

   • Cushion Everything in increments

   • Cushion Deleting your account

   • Cushion Designing the subscription page

   • Cushion Rewriting the timeline

   2015

3. • Cushion Funding Cushion

   • Cushion Hiring a team of freelancers

   • Cushion Taking a real break from work

   • Cushion Slack as a notification center

   • Cushion Document your features

   • Cushion 300

   • Cushion Vacations

   • Cushion Offering discounts

   • Cushion Waves of traffic

   • Cushion Less blogging, more journaling

   2016

4. • Cushion My typical week as a founder

   • Cushion Building components in a sandbox

   • Cushion Reactive time with Vue.js

   • Cushion Visualizing daylight saving time

   • Cushion Recording screencast GIFs

   • Cushion Writing a job listing

   • Cushion Using feature flags to run betas

   • Cushion Our first company lunch

   • Cushion How to embed Vue.js & Vuex inside an AngularJS app... wait what?

   2017

5. • Cushion The “Update Available” alert

   • Cushion Improving readability with bigger fonts and higher contrast

   • Cushion My design workflow

   • Cushion Simplifying our build process and SSL with Cloudfront

   • Cushion Restructuring an evolving app

   2018

6. • Cushion The new invoice page is live

     With only days before the SCA deadline, I launch the new invoice page with to be SCA-ready while also paving the way for more improvements.

   • Cushion Integration testing the invoice page with Cypress

     Wrapping up my work on the invoice page, I set up integration testing using Cypress to make sure that everything continues to work end-to-end.

   • Cushion Tidying up as you go

     Continuing to make progress on the invoice page, I talk about some of the ways I’m improving the codebase along the way.

   • Cushion A subsidized plan for 2021

     A chat with a user leads me to consider a subsidized plan for the New Year to help folks through the pandemic.

   • Cushion Redesigning the invoice page for SCA with Stripe Elements

     I pause work on the account page to make sure Cushion’s invoice payment integration is ready for the SCA deadline.

   • Cushion Rethinking the pricing page

     In needing to redesign the pricing page for the new account section, I decide to rethink the structure of Cushion’s existing plans.

   • Cushion A dev’s troubleshooting journey

     An innocent bug report unfolds into a roller coaster ride of a troubleshooting journey.

   • Cushion Scaffolding the account page

     As I begin building Cushion’s new account page, I start by scaffolding a static version of it and building the components it requires.

   • Cushion Redesigning the account section for SCA with Stripe Billing customer portal

     With SCA regulation going into effect at the end of the year, I prioritize migrating to the Stripe customer portal, which means redesigning the account section.

   • Cushion Designing a new layout system

     After years and years of incrementally tweaking the design of Cushion, I take a holistic look at the layout system.

   • Cushion Redesigning the blog

     After redesigning Cushion’s homepage, I take the next step in migrating to Contentful by rethinking the blog.

   • Cushion Animating the new homepage hero

     To keep my mind busy while dealing with a tough time, I distract myself with Cushion’s new homepage animation.

   • Cushion Responsive images for different layouts

     While building Cushion’s new homepage, I go the extra mile to swap out better-fitting images for different breakpoints.

   • Cushion A flexible way of using Nuxt.js with Contentful CMS

     After migrating Cushion’s changelog to Contentful, I move onto the homepage, where I narrow in on an approach to compose pages entirely in the CMS.

   • Cushion Migrating the changelog to the Contentful CMS

     In my initial step towards migrating Cushion’s marketing site to Contentful, I start with the changelog.

   • Cushion Promoting invoicing to the main nav

     I reworked the main nav to include invoicing, which was met with a wave of thanks from users.

   • Cushion The next big rocks

     After launching Cushion’s new onboarding, I detail the next few items on my to-do list, which for once are not new features.

   • Cushion Onboarding is live

     A weekend turned into a month, but Cushion’s new onboarding is finally live. Instead of focusing on the launch itself, I talk through my favorite part.

   • Cushion Composable onboarding

     To provide a more pleasant codebase for Future Jonnie to inherit, I restructure the onboarding to be composable and easily testable.

   • Cushion Writing my own utility methods

     I decide to write a few utility methods myself, rather than relying on 3rd party library, and I’m glad I do.

   • Cushion Using a utility library vs building my own

     Torn between adding a dependency for a utility method or writing it myself, I talk through the pros and cons of both approaches.

   • Cushion A reminder to write

     Determined to launch thew onboarding flow, I forgot to write for a week and it shows.

   • Cushion The date picker component

     Continuing my work on Cushion’s onboarding flow, I build a new and improved date picker component.

   • Cushion Building components for the long run

     With my recent work on Cushion’s new onboarding flow, I take a meandering walk through the new components I built for it that are all typed and tested.

   • Cushion Investigating inflection points

     Stepping back to look at Cushion’s growth over its entire lifetime reveals a crystal clear moment when everything went south.

   • Cushion Recalibrating my estimates

     I start working on the new onboarding flow, but quickly realize it won’t be a weekend project.

   • Cushion A friendly onboarding flow

     As a first stab at onboarding, I design a flow that includes myself asking questions, which hopefully provides a friendly intro to the app.

   • Cushion Bringing back onboarding

     In an attempt to ease people into the app rather than pushing them out of the airplane, I decide to bring back a proper onboarding flow.

   • Cushion Rough sketches

     After feeling reluctant to reveal any design progress, I decide to bite the bullet and share a few rough sketches—no matter how uncomfortable it feels.

   • Cushion Flattening the nav

     Continuing the idea of the single click, I talk through a potential path to flattening the nav from multiple layers down to one.

   • Cushion Well, this is embarrassing

     Browsing through Cushion, I realize something strange. As I troubleshoot the anomaly, I discover an embarrassing truth.

   • Cushion Sending newsletters again

     I sent my first Cushion newsletter in over a year and a half, which sounds crazy, but nonetheless, it feels great to send them again.

   • Cushion Validating assumptions

     Before diving into analytics, I decide to spend time writing database queries that could validate some of my assumptions using existing data.

   • Cushion Intentional analytics

     After building Cushion so far based purely on assumptions and intuition, I finally start to think about using analytics to help guide me.

   • Cushion This app has good bones

     A thought-provoking conversation leads me to realize that Cushion is still solid and worth iterating on, instead of restarting from scratch.

   • Cushion Keeping API requests simple

     After establishing a new guiding principle to keep API requests simple, I describe how I could refactor a complex view that relies on a heavy API request.

   • Cushion A single click

     I discuss a pain point in the current Cushion involving the number of clicks it takes to get to where you need to go. What if it only took one?

   • Cushion Shaping Vuex through testing

   • Cushion Excluding a folder from VSCode’s search (and disabling Jest’s generated coverage reports)

   • Cushion Retaining state with the router in a single page application

   • Cushion Custom focus rings using :focus-within

   • Cushion Testing v-on="$listeners" in Vue.js

   • Cushion Vue + ESLint + Prettier conflicts

   • Cushion Speeding up Jest tests with --runInBand

   • Cushion Moving the Cushion Journal to my blog

   • Cushion Updating Sentry

   • Cushion Updating Skylight and dealing with ActiveSupport

   • Cushion Reducing Heroku CI time by 35% for an extra penny

   • Cushion The build failed, but I swear it wasn’t me

   • Cushion A hiccup with subdomain routing

   • Cushion Upgrading to Ruby 2.7.1

   • Cushion QA’ing pull requests using Heroku Review Apps

   • Cushion Subdomain routing in Sinatra

   • Cushion Redirecting the Heroku “Open app” button to a custom domain

   • Cushion Reloading Ruby with Sinatra::Reloader

   • Cushion Exploring a modern Cushion

   • Cushion Migrating the Cushion website to S3 to avoid dealing with SSL

   2020

7. • Cushion Quick launches after a big launch

     After launching the Schedule timeline beta, I’m able to easily launch a handful of smaller releases to keep progress going.

   • Cushion The new Schedule timeline is in beta!

     To get folks to start testing the new Schedule timeline early, I released the initial beta this weekend.

   • Cushion Zooming into the schedule timeline

     With the schedule timeline nearing a beta launch, I take a couple more weeks to sneak zooming into the feature set.

   • Cushion Flipping the schedule timeline

     In an unexpected moment, I decide to try vertically flipping the new schedule timeline, so projects stack from the top.

   • Cushion Handling timeline labels

     Determined to always display labels on the new schedule timeline, I detail all the edge cases I’ve gotten myself into.

   • Cushion Visualizing projects in the new schedule timeline

     Now that I have a canvas for the new schedule timeline, I need to fill it with projects.

   • Cushion A freeform scrolling timeline

     After thinking through a modern schedule timeline, I start by enlarging the timeline to full-page and adding freeform scrolling.

   • Cushion Exploring a modern schedule timeline

     Taking a break from the Clients section, I get a burst of inspiration thinking about scheduling.

   • Cushion Revisiting the UX for client notes

     Continuing work on the new Clients section, I revisit client notes, but with a few UX improvements.

   • Cushion Overflow shadows using the Intersection Observer API

     Improving a upon the overflow shadows in Cushion, I replace scroll events with the Intersection Observer API.

   • Cushion Addressing beta feedback for the new Clients section

     After rolling out the new Client section to a few dozen beta users, I start applying their feedback.

   • Cushion Upgrading to Vue 3

     While making forward progress with the new Clients section, I take a break to upgrade the new codebase to Vue 3.

   • Cushion A Safari performance issue and other stresses

     An already stressful time is made even more stressful by a Safari performance issue with nested grids.

   • Cushion Time period filter and totals for the Clients section

     With the Clients section beta up and running, I launch my first incremental update.

   • Cushion A video call with a friend about marking projects as paid

     A video call with a friend provides some interesting insight into a potential direction for restructuring the app.

   • Cushion The new Clients section is now in private beta

     After a heads-down week, I managed to reach the first milestone in releasing the new Clients section—private beta.

   • Cushion Stabilizing PostgreSQL memory issues with pgbouncer

     In an update of the database memory saga, I discover pgbouncer, which puts a stop to the constantly climbing memory woes.

   • Cushion A top-level “Clients” section

     With the sidebar navigation ready to deploy this weekend, I get an early start on the top-level “Clients” section.

   • Cushion Improving the sidebar nav

     After regretting, but living with, the skinny sidebar nav of obscure icons, I finally set a course to improve its UX.

   • Cushion Sending blog posts as emails - Part 2

     Following up on the initial proof of concept, I build the complete system to send journal posts as emails.

   • Cushion Sending blog posts as emails

     In an effort to grow readership, while also prototyping an idea, I start building a system to email my posts.

   • Cushion Sticky line item totals

     Putting the final touches on the invoice form, I apply a sticky behavior to the line item totals.

   • Cushion Little details: Overflow shadows

     I spend extra time getting a little detail right by tying shadows to whether the underlying content has overflow.

   • Cushion Redesigning the flow for importing tracked time into invoices

     With the last remaining to-do on my list for the new invoice form, I tackle the flow for importing tracked time.

   • Cushion A week of cleanup

     With the inline forms behind me, I spend a week cleaning up the codebase with a focus on Cushion’s form states.

   • Cushion Building the inline form system

     After detailing how I planned to build inline forms in Cushion, I went ahead and built the first one for creating clients inline.

   • Cushion Inline forms and the weight of the next big task

     In between big tasks, I distract myself with smaller tasks until I’m ready to finally face it—inline forms.

   • Cushion Designing a breadcrumbs component

     Chopping away at the new invoice form, I designed and built a new component for breadcrumbs.

   • Cushion Thinking about a “test mode”

     Aggravated by people signing up with no real intention to use Cushion leads me to consider a “test mode” where they can try the app without signing up.

   • Cushion Redesigning the invoice line item footer

     While redesigning the invoice form, I share the decision-making behind the design of the new line item footer.

   • Cushion Migrating CI to GitHub Actions

     Frustrated with Heroku, I start migrating away from it, beginning with continuous integration.

   • Cushion Troubleshooting the database upgrade

     Upgrading Cushion’s database leads to a week of troubleshooting performance issues.

   • Cushion Upgrading the production database

     After receiving an email from Heroku to upgrade Cushion’s database, I upgrade Cushion’s database.

   • Cushion 7 years old

     With Cushion reaching the 7-year mark, I reflect on its life and plot a course for its future.

   • Cushion Thinking through a new invoice form

     At the fork in the road, I choose the invoice form as the next step in renovating Cushion, including a long-awaited list of improvements.

   • Cushion The calm after the sprint

     With a couple big launches behind me, I think about what to tackle next or whether I need to pick a direction just yet.

   • Cushion The new account page is live

     After launching Cushion’s new invoice page last week, I launch the new account page this week with a ton of other goodies.

   2021

8. • Cushion “Software” with a capital “S”

     I hit a roadblock designing a UI that didn’t excite me, so I decide to take a step back and rethink a more personalized design.

   • Cushion Adding hotkey labels to the UI

     After taking a short break to collect myself, I eased back into work with a low-priority feature that I’ve been itching to add for a while.

   • Cushion Moving & resizing workloads in the timeline

     While building the drag & drop interaction for workloads, I accidentally created the coolest interaction I’ve ever made.

   • Cushion Editing workloads in the timeline

     After taking a couple weeks off to move into our new home, I’m back in the saddle with creating and editing workloads.

   • Cushion Vacations in the timeline

     To continue reaching feature parity with the existing schedule view, I added vacations to the new timeline.

   • Cushion Nested modal drawers with parallax

     Over the weekend, I ate the broccoli and built a nested drawer system, but ended up with a delightful parallax effect.

   • Cushion The evolution of a tooltip design

     The full circle journey of designing a tooltip that’s both simple and useful.

   • Cushion Estimated workloads in the schedule timeline

     After visualizing tracked time, I jumped from the past and into the future to visualize estimated workloads.

   • Cushion Total tracked time in the schedule timeline

     Now that Cushion can visualize tracked time, the next step is to combine tracked time and highlight when you overworked yourself.

   • Cushion Lazy loading tracked time in the schedule timeline

     After being close to launching tracked time in the schedule timeline beta, I decide to spend an extra week adding lazy loading.

   • Cushion Visualizing tracked time in the schedule timeline

     Straying from the plan to bring the timeline to 1:1 feature parity with the existing timeline, I visualize tracked time.

   • Cushion Duplicating an invoice

     I take a short break from the timeline beta to launch the ability to duplicate an invoice. No big deal.

   • Cushion Grouping and archiving projects in the schedule timeline

     On the new path of pursuing a list-based layout, I group the projects by list and add an archive filter.

   • Cushion One step back, two steps forward

     Foreseeing a problematic future with the stacking layout, I rethink the direction and end up down a better path.

   • Cushion Project actions in the Schedule timeline beta

     After adding the ability to add and edit projects in the Schedule timeline, I implement more detailed interactions with project actions.

   • Cushion Creating a project via form in the schedule timeline

     Back to working on the app, I take the leap into creating projects, but via form first instead of click & drag.

   • Cushion New year, new homepage

     I spend my holiday break bringing more fun to the Cushion homepage with a new design, full of illustrations and animations.

   2022

9. • Cushion Building a table for the nth time

     Now that I have data to wire up, I set out to build a table component, but first I revisit past attempts.

   • Cushion A return to tabbed navigation

     With a focus on navigation, I return to the early days when Cushion had a simple tabbed nav.

   • Cushion End-to-end testing with Playwright

     With the stack picked out, I set up end-to-end testing from the start, so I can get in the habit of testing user flows without any excuses.

   • Cushion Vercel, Supabase, Vue, and Vite

     As I rethink Cushion in the modern age, I detail my choices for platform, stack, and database.

   • Cushion Imagining Cushion circa 2016 in 2024

     With Cushion’s 10-year anniversary approaching, a theory leads to an attempt at a modern upgrade, but with 2016’s feature set.

   • Cushion A weekend marathon of an infrastructure upgrade

     I spent a weekend upgrading Cushion’s Heroku stack and Ruby version, which sent me down a path of fixing hundreds of failing tests and removing a feature.

   2023

10. • Cushion Cleaning up the cobwebs

      After years of side-eyeing an unreleased feature that has been nagging me while slowing down the app, I finally take the time to remove it from the app.

    • Cushion Building a table for the nth time - Part 2

      Following up on the initial post about building a table in Cushion, I actually detail my approach this time.

    • Cushion How to use Playwright with GitHub Actions for e2e testing of Vercel preview deployments

      I spent way too long trying to find out how to set up e2e testing with Vercel preview deploys, so I wrote a quick post to save others.

    2024

11. • Cushion Eating my own dogfood again

      Now that I’m freelancing full-time, and using Cushion again, I’ve fallen in love with it all over again, but I also feel every rough spot.

    2026