The Stack
Tools that survive contact with a real week.
This is not a ranking, and it is not a list of things that look good in a screenshot. Every entry below was paid for and used on live work — kept, or dropped for a reason we can name. Each one is written against a specific job, and each one says the situation where it will let you down.
No paid placements. No affiliate links, no “featured” slots, no brand paying for a better sentence. If a tool ever pays us, the line goes at the top of the entry in the same size as the name — not in a footnote nobody reads.
Seven shelves, ordered by where the work happens
Free costs nothing, no card. Freemium has a free tier that holds up for a while. Paid asks for money before it does anything. Open source you can run yourself, which is a different kind of bill.
Shelf 01 · 8 tools
Writing & thinking
The work before the work. Nothing on this shelf should make a sound.
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Obsidian
Plain-text notes in a folder you own, linked into a graph that gets more useful the longer you keep it.
Skip if you want sync to just work between a Windows laptop and an iPhone without paying for Obsidian Sync or babysitting a Git repo.
Freemium -
Notion
Docs, wikis and light databases on one shared surface, so the plan and the writing can live together.
Skip if you open the same page forty times a day — every keystroke waits on a network round trip, and you will feel it by Thursday.
Freemium -
iA Writer
One file, one cursor, no sidebar. Markdown with typography that was clearly argued about.
Skip if you need to manage a 60,000-word manuscript with footnotes and cross-references — it is a writing surface, not a document system.
Paid -
Ulysses
Long-form writing broken into sheets, with goals and one-click publishing to WordPress and Medium.
Skip if a subscription for a text editor bothers you on principle — it never converts to a licence you keep.
Paid -
Bear
Fast markdown notes with tags instead of folders, and the best typography of any notes app on Apple hardware.
Skip if anyone on the project uses Windows or Android — it is Apple-first, and the web version is a companion rather than a replacement.
Freemium -
Lex
An AI editor built around the paragraph rather than the chat window, with suggestions you accept or ignore in place.
Skip if you write in anything but English — the suggestions drift quickly once the draft leaves the model’s comfortable register.
Freemium -
Claude
A drafting and editing partner that can hold an entire brief, three old drafts and a style note in view at once.
Skip if the sentence needs a citation you can defend — it will produce a confident claim and a source that does not exist.
Freemium -
Hemingway Editor
Paste a draft and it marks the sentences doing too much work, in colours you cannot ignore.
Skip if the voice is deliberately dense — it will sand off the only interesting sentence on the page and call it a fix.
Free
Shelf 02 · 8 tools
Planning & tasks
A plan you cannot see on one screen is not a plan. It is a filing cabinet.
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Linear
Issues, cycles and a keyboard-first interface that makes triage something you do in four minutes, not forty.
Skip if you are tracking three unrelated client projects — Linear assumes one product, one backlog, one rhythm, and it fights you otherwise.
Freemium -
Things 3
A personal task list that respects the difference between today, this evening and someday.
Skip if you need to share a list with a client or a collaborator — there is no shared workspace, by design.
Paid -
Todoist
Tasks on every platform you own, with filters that keep working when the backlog gets ugly.
Skip if you want structure imposed on you — it will happily hold four hundred loose tasks and never once tell you to delete one.
Freemium -
Sunsama
A daily planning ritual that pulls from your calendar and task apps, then asks you to commit to an actual day.
Skip if you plan weekly rather than daily — the whole product is built on a morning review you will skip by week three.
Paid -
Motion
Auto-schedules tasks into your calendar by deadline and priority, and reshuffles when the week goes sideways.
Skip if your week is mostly meetings you do not control — it keeps re-planning a calendar that was never yours to plan.
Paid -
Basecamp
One place per project — messages, files, schedule, no feed — so a client can find the thing without a tour.
Skip if you need dependencies or burndown charts — there is no Gantt view, deliberately, and you will spend a month fighting that.
Paid -
Trello
Boards and cards that a client understands in ten seconds, with no onboarding call required.
Skip if a board goes past roughly two hundred cards — it stops being a plan and becomes a wall you scroll past.
Freemium -
Notion Calendar
Your calendars overlaid in one grid, with Notion pages attached to the meetings that need a doc.
Skip if you live in Outlook — it syncs Google and iCloud accounts, and a corporate tenant is not going to bend for it.
Free
Shelf 03 · 7 tools
Design & assets
Files, assets, and the forty minutes before anything is real.
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Figma
Multiplayer design files with comments, prototypes and a component system that survives a handoff.
Skip if you are laying out a two-hundred-page print book — the file will crawl and the colour management is wrong for ink.
Freemium -
Penpot
Open-source design files in the browser, self-hostable, with CSS-ready output instead of a wall of exported PNGs.
Skip if the work depends on plugins and community files — Figma’s ecosystem is half the reason people stay, and Penpot has not rebuilt it.
Open source -
Canva
Templates that get a decent-looking asset out in fifteen minutes, which is often exactly the brief.
Skip if your brand has actual rules — Canva lets anyone on the team drift off-palette, and nobody notices until the print proof arrives.
Freemium -
Framer
Design and publish a marketing site in the same canvas, with real breakpoints instead of guesses.
Skip if the site needs four hundred blog posts and real content modelling — the CMS is fine at twenty entries and painful at two hundred.
Freemium -
Excalidraw
Hand-drawn diagrams that look like thinking rather than a pitch deck, with a shared link in one click.
Skip if the diagram has to be accurate enough to hand to an engineer — there is no grid, no constraints and no source of truth behind it.
Open source -
Unsplash
Free photography that does not look like stock photography, licensed for commercial use without a call.
Skip if the image is load-bearing on a product page — the same photograph is already on four thousand other sites, including your competitor’s.
Free -
Squoosh
Drag an image in, get a WebP or AVIF out, and see the file size before you commit to it.
Skip if you are converting three hundred images — it is one file at a time in a browser tab, and the tab will die before you finish.
Free
Shelf 04 · 7 tools
Money & admin
The part nobody puts on the homepage, and the part that decides whether the month worked.
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Stripe
Card payments, invoices and a dashboard your accountant can read without a phone call.
Skip if you sell to consumers in a country where Stripe has not launched — the workaround costs more in fees and support than a local processor.
Paid -
Wise
Hold and get paid in multiple currencies without losing three percent to a conversion spread.
Skip if you need credit terms or an overdraft — it is a money transmitter, not a bank, and it will not lend you a month’s runway.
Free -
Lemon Squeezy
Merchant of record for digital products: they handle VAT, sales tax and the receipts you would rather not think about.
Skip if you sell physical goods with returns — the merchant-of-record model gets awkward the moment a parcel and a refund address are involved.
Paid -
Wave
Free invoicing and bookkeeping for a one-person business, with a decent accountant export.
Skip if you are outside the US or Canada — tax handling and bank-feed coverage drop off fast past those borders.
Free -
Xero
Double-entry accounting with a real bank feed, multi-currency and an export any bookkeeper accepts.
Skip if you are pre-revenue — twenty-odd a month to reconcile four transactions is a hobby wearing a business hat.
Paid -
QuickBooks
The US default: payroll, 1099s, inventory and an accountant who already knows where everything is.
Skip if you are a solo freelancer outside the US — the localisation is thin, the price is not, and the upsells never stop.
Paid -
Deel
Contractor agreements, payments and compliance across more than a hundred countries, with the paperwork attached.
Skip if you pay two people in your own country — the per-seat fee and the KYC flow cost more time than a bank transfer and a signed PDF.
Paid
Shelf 05 · 8 tools
Publishing & distribution
Getting the thing out of the folder and into somebody else’s Tuesday.
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Kit
Email lists, sequences and forms that stay out of the way of the writing, with automation that is boring on purpose.
Skip if you plan to sell courses and paid subscriptions in the same checkout — you will be stitching three products together with two integrations.
Freemium -
Ghost
A publishing platform with memberships and email built in — self-host it, or pay them to keep the server alive.
Skip if you do not want to own a server image and a backup policy — the managed plan is the honest choice, and it is not cheap.
Open source -
Buttondown
A small, text-first newsletter tool with a clean API and none of the growth theatre.
Skip if you need a twelve-step automation funnel — the automation is deliberately basic and it will not pretend otherwise.
Freemium -
Beehiiv
Newsletter publishing with referrals, an ad network and analytics that assume you want to grow.
Skip if you have two hundred subscribers and no plan to grow — you will pay monthly for a growth machine you never switch on.
Freemium -
Substack
Publishing plus payments, with the audience living on a network that already has readers in it.
Skip if you want to own the list outright — export is real, but the discovery and the ten percent are not yours to renegotiate.
Free -
Transistor
Podcast hosting with multiple shows, per-episode analytics and an RSS feed that behaves.
Skip if you publish one episode a month — the entry plan is priced for people shipping weekly, and you will notice.
Paid -
Buffer
Queue posts across networks so you stop opening four apps to say one thing.
Skip if your whole strategy is one platform — the scheduler puts a layer between you and the reply button, and replies are the point.
Freemium -
Plausible
Cookie-free analytics in one small script, with a dashboard you can read in fifteen seconds and no consent banner.
Skip if you need funnels, cohorts or attribution — it counts pageviews well and then stops, and no amount of filters will make it a growth tool.
Paid
Shelf 06 · 6 tools
Automation & glue
The glue that stops you being the glue. Keep it boring and documented, or it becomes a second job.
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Zapier
Connects thousands of apps with triggers and actions, and is the reason you no longer copy rows between two tabs.
Skip if you are moving more than roughly ten thousand tasks a month — per-task pricing turns a glue job into a line item you have to justify.
Freemium -
Make
Visual multi-step automations with branching and error handlers, at a lower per-operation price than the obvious alternative.
Skip if a non-technical client has to maintain it — the canvas is powerful and genuinely confusing at the same time.
Freemium -
n8n
Self-hosted workflow automation with real code steps when the visual nodes run out of road.
Skip if you do not want to run a server, a database and monthly upgrades — self-hosting is a subscription you pay in Saturdays.
Open source -
Raycast
A macOS launcher that quietly replaces about nine small utilities, with extensions for the rest.
Skip if your team is mixed-platform — the Mac build gets the extensions first, and the Windows one is still catching up.
Freemium -
Espanso
Text expansion in every app you own, defined in a plain YAML file you can put in version control.
Skip if you are on a managed work laptop — a background keyboard listener is exactly the thing IT is trained to block.
Open source -
Apple Shortcuts
Automate the operating system you already have — files, photos, Focus modes, app actions — with no extra account.
Skip if the automation has to run on a schedule while the Mac is asleep — it will not, and you will find out on the morning it mattered.
Free
Shelf 07 · 6 tools
Reading & research
Input has a budget. These are the tools that help you spend it on purpose.
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Readwise Reader
One inbox for articles, PDFs, newsletters and video, with highlights that sync out to wherever you write.
Skip if you read four things a week — a monthly fee to maintain a backlog is a subscription to guilt.
Paid -
Instapaper
Save an article now, read it later as clean text on any device, offline, without the cookie wall.
Skip if you want annotation and export into your notes — highlights are basic and the export is thinner than the marketing suggests.
Freemium -
Feedly
RSS feeds plus keyword tracking, so you can follow a whole beat without opening six tabs a day.
Skip if you follow six blogs — an RSS reader is a fine idea and a worse habit than a bookmark folder you actually check.
Freemium -
Zotero
Citations, PDFs and bibliographies that stay consistent across thousands of citation styles, for free.
Skip if the piece has three links in it — the setup and the plugin dance never pays back on a two-page memo.
Open source -
Perplexity
Answers with sources attached, which is the right shape for the first twenty minutes of a question.
Skip if the answer goes into a client deliverable — some of those citations are the wrong paper, and you will not notice unless you open them.
Freemium -
Fathom
Records, transcribes and summarises calls, then drops the notes into your CRM before you have closed the tab.
Skip if the call is confidential or under NDA — you are sending audio to a third party, and you have to say that out loud before you hit record.
Freemium
The Letter
One letter a week, about the work the tools can’t do.
The directory is the reference. The letter is the part that changes your mind: one person, one thing they shipped, and what it actually cost them — including the tool they cancelled halfway through.
One or two tools a week, maximum. Never a list of twenty. If a week has nothing worth recommending, it says that instead.
Get the letterOpens Buttondown, where the list lives. One letter a week, unsubscribe anytime.