When I started Northlight Advisory Services, I already knew which project management tool I was going to use.
I’d spent months evaluating the options four years earlier. I’d done the research, run the trials, sat through the vendor calls. By the time Northlight existed, that work was already done.
The evaluation is worth documenting: a real decision, made twice, in very different contexts, with genuinely different requirements each time.
Here’s the full story.
I’ve been here before
My first real experience with project management software was Trello.
Before that, I worked in retail — for more years than I want to admit — and project management software simply wasn’t part of the work. You had a notebook. You wrote things down.
Then I joined Accredible, working in marketing across time zones, and suddenly I needed people in different countries to see what was happening without having to ask me. Trello made the work visible. That shift — from information held in my head to information available to the people who needed it — changed how I thought about work.
I also discovered that I really like Kanban boards.
I still use Trello for one of my favourite annual projects: Christmas. I create a column for each person on my list and add every gift individually. Tags tell me whether it’s a stocking item, whether I bought it locally or online, whether it has arrived, whether it’s wrapped, and whether I have a tracking number. I can see exactly where everything stands at a glance.
It works brilliantly.
I have a lot of affection for Trello. But eventually I needed more than it could give me.
The real evaluation: 2022
The formal PM tool evaluation happened while I was at Divine Renovation Ministry. It wasn’t a casual comparison. We spent months researching, running trials, talking to vendors, and working through what a large, distributed organisation actually needed: process management, task management, calendars, scheduling, collaboration, reporting, dashboards, and visibility across increasingly complex work.
Over that process, I evaluated or used Basecamp, Microsoft Planner, Microsoft To Do, Microsoft Project, Monday.com, Asana, Notion, Airtable, Todoist, Smartsheet, Wrike, and ClickUp.
ClickUp won.
What I learned from the alternatives
Several of them were strong products — the right fit for different teams or different problems. The table below captures my actual evaluation — not a benchmark, just what I found.
| Tool | What I liked | What didn’t fit | My verdict | 2026 price (USD/mo) |
|---|---|---|---|---|
| Trello | Excellent visual Kanban; simple; great for async collaboration | Not enough for broader operational complexity | Still excellent for bounded, visual projects | Free / $5 per user |
| Basecamp | Worked for some teams and a lot of individuals | Awkward for me; less customisable; I lost the clarity I had with Trello | Not for me | $15 per user or $299 flat |
| Microsoft Planner | Already included in the Microsoft ecosystem; useful for shared work | Weak hierarchy; no useful subtasks at the time; became unwieldy across multiple projects | Good enough for simpler teams; not enough for complex work | Included with M365 / $10 add-on |
| Microsoft To Do | Excellent for individual tasks and lists | Not project management | Use it for what it is | Free with M365 |
| Microsoft Project | Extremely deep; excellent for highly structured project work | Overpowered, expensive, wrong fit for our work | Better suited to specialised environments | From $10 per user (Plan 1) |
| Monday.com | Strong views, reporting, and project functionality | Cost per seat | Good product; didn’t win on value | From $9 per user |
| Asana | Strong project functionality, views, and reporting | Cost per seat | Good product; didn’t win on value | From $10.99 per user |
| Notion | Flexible; useful as a knowledge and database environment | Never clicked for me as a PM tool | Interesting, but not my tool | Free / $10 per user |
| Airtable | Powerful, flexible database structure | A three-dimensional Excel spreadsheet — excellent for data work, not for PM | Great tool, wrong job | Free (limited) / $20 per user |
| Todoist | Simple task management | Too individual-task-oriented for this use case | Use a to-do tool if that’s what you need | Free / $5 per user |
| Smartsheet | Considered | Never gave me confidence it would deliver, particularly around dashboards | Didn’t make the cut | From $9 per user (no free tier) |
| Wrike | Considered | Didn’t give me the right fit or confidence | Didn’t make the cut | Free (5 users) / $10 per user |
| ClickUp | Flexible, hierarchical, multiple views, workflows, dashboards, forms, documents, goals, integrations | Can be complex; interface changes frequently; free tier has meaningful limitations | Best fit for me | Free / $7 per user |
Prices as of August 10, 2026 (USD), billed annually. Prices may change. Tool assessments reflect my 2022 evaluation; product capabilities have evolved since.
A few are worth addressing individually.
Monday.com and Asana were genuine contenders. They had the right views, reporting, and project functionality. The deciding factor was economics. ClickUp’s guest access model also mattered — not everyone needed to create and manage work. Some people only needed to see something, comment, or mark it complete. On ClickUp paid plans, guests don’t consume paid seats; on Asana and Monday.com, external access is more restricted.
Microsoft Planner had one argument in its favour: we were already in the Microsoft ecosystem. For a while, it was good enough. But once projects got complicated, the limitations became obvious. A project with five major tasks and several subtasks each could turn into 30 flat items on the board. That didn’t make the work simpler. It made the board harder to understand. (Subtask support has since improved in Planner, but it arrived later and requires a premium plan.)
Microsoft Project went the opposite direction. It can go very deep. I can see why an engineering, architecture, or construction firm would want that level of detail. But we didn’t.
I needed a bike. Project felt like someone had given me a very large vehicle. Technically, it would get me where I was going. It just wasn’t the right tool for the journey.
Airtable is worth a separate note. I like Airtable. I’ve used it. I think of it as a three-dimensional Excel spreadsheet — powerful when the work is fundamentally about data and databases. Some people do use it successfully as a PM tool; it’s flexible enough to support that, and if you’re drawn to it, a proper trial is worth your time. It just never clicked for me as a task and project tool — the data-first logic is a different way of thinking about work, and I didn’t find it a natural fit.
A good tool isn’t necessarily the right tool.
And then I got genuinely into it
I took the courses. I earned certificates. I became a ClickUp power user and eventually an ambassador (a community recognition badge, not a paid relationship). I learned the administration side and figured out how to build things in it.
None of that was part of the original buying decision.
But it tells me something important about the product. Some software makes you feel like you’re fighting the system. ClickUp made me curious about what else I could make it do.
And when APIs and AI integrations became more accessible, that opened another door. The same tool I’d chosen to organise complex projects could become part of a much larger operating system.
That’s why, when I started Northlight, I didn’t reopen the spreadsheet.
I already knew what worked for me.
What my criteria looked like in 2026
My criteria changed between that original evaluation and starting Northlight.
In 2022, I was thinking about a tool for a large, distributed organisation. In 2026, I was thinking about a tool for one person.
That makes the problem both simpler and more demanding.
I don’t need a dozen people assigned to a task. It’s mostly me and Claude.
I use list view more than Kanban now. But I need a calendar — something that lets me see my content work across channels and know what’s happening when. I need subtasks. I need comments, because a task can contain the full history of the work: the brief, the research, the draft, the decisions made along the way. I need workflows.
And I now have two requirements I wouldn’t have put on a list four years ago:
The system has to connect to AI, and it has to have an API I can use with Northlight OS.
If I couldn’t connect my PM tool to Claude, I’d be hooped. If I couldn’t connect it to Northlight OS, I’d be sunk. Those aren’t nice-to-haves. They’re infrastructure.
There was one other consideration I researched carefully before committing: where the data lives. ClickUp’s servers are in the United States. I knew that and chose it anyway — but it shaped how I use the tool.
I don’t use ClickUp as a CRM. I don’t store personal information about clients in it. That’s a deliberate choice. Operational data — projects, tasks, notes, timelines — is one thing. Personal data belonging to individuals is another, and knowingly routing it outside Canada is something I take seriously under PIPEDA. ClickUp won for me. It won within limits I set.
If you’re a Canadian business looking at any of the US-based tools on this list, data residency is worth researching before you decide what you’ll actually put in the tool. Know where the data goes. Then decide what follows it there.
Why ClickUp won — both times
The first time we seriously tested ClickUp, we were using it to build the project plan for implementing ClickUp.
And we just kept finding things it could do.
It had enough depth when we needed depth. It kept things visible when we needed visibility. We could start with a simple list and build toward a sophisticated hierarchy. We could create dashboards and share them with people who didn’t even have seats. We could build different views for different audiences from the same underlying data.
We could create a form for a new event, have that information feed into a structured system, then view the same data as a calendar, filter it by region, or route it to another team entirely.
But what really won me over was workflows.
At the time, most automation meant connecting A to B through something like Zapier. ClickUp let us do something more interesting: design the work so that when one part was complete, the next thing appeared. That matters when someone doesn’t need — or want — to see the entire process at once. They just need to know what to do next.
And ClickUp didn’t require us to start with any of that complexity. You could open it and create a list. Then, when you needed more, you could add more.
That’s what won me over.
It isn’t perfect
The free version has real limitations. I’ve had to work around the lack of custom fields by using tags. There are limits on Spaces. There are things a paid account makes easier that I currently manage differently.
And ClickUp moves things around. A lot.
I’ve had more than one moment where I knew exactly where something used to live, only to find the interface had changed again.
That’s irritating.
But there’s a reason I haven’t left. Usually, if ClickUp can’t do something exactly the way I want, there’s another way to accomplish what I’m actually trying to do. If I can’t figure it out, there’s a large community who have probably already tried something similar.
The product has also continued to grow. Forms, Docs, dashboards, Goals, Whiteboards, new task types, integrations, and calendar capabilities have all expanded significantly since I first started using it. Some of those things barely existed in 2022.
That’s another reason I stayed. The fact that there’s usually a workaround is part of why I still like ClickUp.
Should you use ClickUp?
Not necessarily.
I don’t think everyone needs project management software. If you have a list of things you need to do, use a to-do list. Microsoft To Do is fine. There are plenty of simple options.
Don’t choose a project management system because you think organised businesses are supposed to have one.
If you have actual projects — something with a defined outcome, a beginning and an end, dates, dependencies, and multiple pieces that need to come together — then a PM system starts to make sense.
For a solo advisory practice or a small firm, the question is more specific: do you have concurrent projects with dates, subtasks, dependencies, and multiple moving parts that need to come together? If yes, ClickUp handles that well at a price that makes sense. If your work is primarily managing your own schedule and tracking deliverables, something lighter might be a better fit — Todoist, a well-organised calendar, or even a structured inbox.
If you primarily need a CRM, use a CRM. If you’re managing inventory, use something designed for it. If you’re in engineering or construction with structured work breakdowns and specialised project controls, I’d look at something more purpose-built.
ClickUp can do a lot of things. That doesn’t mean it should do everything.
My honest answer
If you asked me over coffee what PM tool you should use, I’d say:
If you just need a to-do list, use a to-do list. If you actually need project management, ClickUp is a good place to start. But it might not be perfect out of the box.
ClickUp’s strength isn’t that it arrives configured for you. Its strength is that you can make it fit.
The point isn’t to find the objectively best project management tool. There isn’t one.
The point is to find the tool that fits the way you actually work — and gives you enough room to grow when the work gets more complicated.
For me, that was ClickUp.
And for Northlight, I didn’t need to choose it again.
I’d already chosen it.