Why freelancers even need a task tracker
I didn’t actually use a task manager consistently until a client ghosted me halfway through a design sprint. I was juggling copy docs, feedback threads, invoicing, and two contract renewals — all in four different apps, none of them talking to each other. It was chaos. That’s when I realized I wasn’t just doing work… I was managing *work about work*.
If you’re freelancing, you probably already know this vibe — hopping across tabs trying to remember if you sent the final version or just uploaded it to Drive and forgot to email it 🙃. A proper task manager can stop that spiral. But ClickUp and Asana come with so much going on by default that setting them up feels like customizing an airplane cockpit when you just wanted to fly to Denver.
So which one’s better if you’re trying to track actual deliverables and not drown in subtasks and notification settings? Let’s get into what using each one really feels like when you’re a one-person show.
Setting up a new project from scratch
ClickUp gives you that Swiss Army knife vibe. Templates! Views! Custom statuses! But it’s overwhelming if you just wanted something basic like “Client: Brett — due in 3 days.”
I remember the first time I made a space in ClickUp — I accidentally created a dropdown with nothing in it, then couldn’t delete it. You literally can’t delete custom fields once they’re applied to a list without deleting the list itself 😂. That’s… not okay.
Meanwhile, Asana is boring but clean. You open it up, you get the list layout by default. You click “Add Task,” give it a name, set a due date, assign it to yourself (or no one), and boom, it’s there. Done. That’s legit all you need when you’re just trying to ship work for money and not burn 45 minutes on pastel label schemes.
If your setups are always evolving, ClickUp lets you tinker endlessly — which I love-slash-hate. But if you want something that loads fast and doesn’t make you think, Asana wins this round.
Tracking deadlines without losing your mind
Here’s the deal. Embedding deadlines with flexibility is super important when you’re a freelancer juggling projects that start and stop at random. ClickUp lets you create multiple due dates within the same task — like a start and end date, review checkpoints, or even nested due dates for subtasks. That somehow broke a recurring task for me where I only updated the start date… and then the task disappeared from Today. Totally gone. Had to find it by manually opening the entire list 😑.
Asana, by contrast, skips most of the fancy logic and gives you a timeline view that’s way easier to adjust. It’s like a simplified Gantt chart but snappy. You drag a bar, it shifts the date. Done. And when you change a due date, it doesn’t de-sync anything quietly in the background — which, yes, has happened in ClickUp more than once when task dependencies were toggled on without me realizing.
If you’re treating your tasks more like a checklist with shifting timelines, Asana’s approach is more beginner-proof. But if you’re building workflows with interlinked steps (e.g. “send draft → wait for feedback → revise → deliver”), ClickUp can actually help you see the knock-on effects. If it doesn’t glitch out.
Client collaboration with minimal tech teaching
One of the biggest tests for me: can a random client jump into my task manager and actually understand what’s going on?
In Asana, yes. You can add a guest, assign them a task, and they just get a notification with a super plain interface. They click it, they can see the details, maybe leave a comment. No setup needed. I’ve sent Asana tasks to clients who literally still forward spam thinking it’s real, and even they didn’t mess it up 😛
But ClickUp? Oh boy. I had a client straight-up think I’d sent them an internal admin dashboard. There are too many options visible by default — docs, goals, time tracking, custom views. Everything’s labeled with jargon-y terms like “workspace,” “dashboard,” and “spaces.” It looks like a productivity expert’s Notion template had a baby with Jira.
Unless you’re paying for a workspace where you can restrict views and tweak who sees what, ClickUp isn’t the best first impression for most clients. And that definitely matters when they’re already picky about where things are stored.
Automating repetitive freelance work
Okay, this is where it gets messy but juicy. I’m big on using automation to cut down on small stuff — like when a project kicks off and I want a pre-built list of tasks to drop in, or when I mark a draft as done and want it to ping the client.
ClickUp has native automations, and they’re surprisingly powerful. Probably too powerful. I once made two automations that triggered on the same condition (status changes to ‘Done’), and they both pinged the client AND moved the task *back* to ‘To Review’ because one copied from another list. Chaos. I had to use task IDs and filter logic just to untangle it.
Asana’s automation builder is less ambitious but way safer. It’s mostly “When this happens → do that.” No looping, no overlap. That means less power, but also fewer landmines. In some cases, I’ve had to pair it with Zapier or Make to do real triggers like “When a new client task is created, copy onboarding tasks.” But I can trust it won’t suddenly fire twice because I renamed a field.
If you’re not ready to diagnose why a webhook fired twice in the middle of your vacation, Asana’s more predictable. If you’re okay with spending an hour making sure a custom automation won’t break everything when field names change, ClickUp gives you way more options.
Mobile app experience when you’re on the go
Heads up: ClickUp’s mobile app has made me rage-quit more than once. It’s gotten better over time, but it still loads slow, scrolls weird, and UI elements are tiny. Trying to mark a subtask as done while walking through a grocery store feels like doing surgery with mittens on.
Asana’s mobile app, on the other hand, is nothing fancy but it works. You open it, you see your tasks. You mark something done, it updates right away. Subtasks are visible in a tap or two. It’s not perfect, but it behaves like a normal app should.
If you’re someone who uses your phone as your second brain (like I do — adding ideas while brushing my teeth), the Asana app is less likely to derail you. ClickUp’s app still feels like it’s trying to be the desktop version, and it’s just not built for fast tapping.
Dealing with notifications and email overload
I once missed a deadline because ClickUp literally did not notify me. It was a task that had no due date, but had a reminder set to one day before. Turns out, changing the list view to “group by status” had some weird interaction that hid the overdue flag. I didn’t see it for four days.
Asana’s notification system is tighter. You get fewer pings, but they actually land in your inbox at the right time. The digest email that says “Tasks due today” has saved me more than once when my brain was fried.
BUT — Asana also has this bizarre behavior where if you assign a task to someone else and remove yourself, you stop getting notifications. Even if you’re still listed as a collaborator. Found that out the hard way.
Both systems have hard-to-find settings related to notifications. ClickUp hides email setting toggles inside your personal profile, not at the task or workspace level. Asana buries collaborator options, so you might be watching a task and not realize you unsubscribed just by leaving a comment.
Neither is perfect. But I’ve spent less time tweaking Asana’s notification rules, and that’s usually a good sign.
How much does it cost to do the basics
Price seems simple at first… until you realize what’s actually locked behind paywalls. Asana’s free plan looks generous, but there’s no timeline view unless you pay. That’s fine if you’re a list-lover, but bad if you want visual context.
ClickUp, weirdly, gives you timeline, board, and Gantt charts for free — but limits automations and guests unless you upgrade. It’s almost like the opposite tradeoff. You can customize the heck out of it, but if you want to share stuff with clients cleanly, that’s gonna cost you.
For me? I used ClickUp for free with hacky workarounds, then eventually caved and paid for Asana once I had two clients asking for timeline access. At about $5 per month on a solo seat, that wasn’t a hard decision. But if I were doing internal ops or multi-project pipelines with lots of dependencies, I’d probably still be using ClickUp… and just babying the automations constantly.
¯\_(ツ)_/¯