PM Advice – ClickUp, Evernote, Trello, Monday…we’ve tried everything!


Further details: I would like PM software to help manage my small business. We have 2 full time employees and hire on freelancers/independent contractors frequently for one-off projects or long term project. We currently have 2 teams that we have on retainer that we work with. One team is for video production (primarily youtube, but also short video ads, promos etc), the other team is for social media management (write, schedule and post instagram posts, design instagram story slides, writes a weekly email to subscribers, manages our facebook ads). Outside of those two teams, we hire people for short one-off projects here and there.

What we do is provide educational products and programs to teach individuals how to get into virtual assisting and virtual work.

Our big overarching projects currently include:

  1. Building a College-accredited course in conjunction with a local non-profit organization
  2. Digital Education: provide products directly to consumers. Online courses, ebooks, pdfs, templates, 1:1 coaching calls, consulting work
  3. Content Production: Instagram, YouTube, Email, Facebook group
  4. Client Work: Although our primary purpose is to provide education, we also have 3-4 recurring clients from our old digital marketing agency that we still perform work for.

These are currently the spaces we have set up in ClickUp. We have used a few different softwares: trello, monday, base camp, evernote, ticktick and currently trying ClickUp.

Outside of our business projects, we would also like to be able to use it for personal tasks/to do lists as well.

What we want is a robust software similiar to ClickUp or Monday. But have the ease of being able to just make a simple to do list on the fly, and then be able to sit down and organize that to do list by project/due dates/priority/assignee’s. We also love integrations. I love ClickUp having a chrome extension and an app and all of that. We use slack primarily for communication so a slack integration would be awesome, and we do have zapier for any other integrations.

Our thoughts on softwares we tried and why they failed:
Trello – Was hard to check and view the data without feeling overwhelmed and for things to start getting lost in the cracks.
Monday – Loved the options but building one from scratch was very difficult as we don’t have a lot of PM experience. The other thing was we couldn’t find a good way or place to just write a simple todo list, that we could reference throughout the day.
Basecamp – Base camp was really cool but the limited hierarchy forced us to create a ton of projects and things started getting lost.
TickTick – This was great but not amazing for long term projects/working with others
Evernote – This for some reason has been our goto for a while for a to do list. But the lack of features is pretty evident. Its useless for collaborations as you can’t edit notes at the same time. Also having to create a note for every individual task if you want automatic reminders is not ideal. And the options to view your tasks is not great.
ClickUp – There is a lot that I absolutely LOVE about this software, but what I’m not in love with is: its not simple enough to just throw down some tasks and have them work together. There’s a ton of options and it can almost feel overwhelming, if I just want to jot down some tasks. I don’t want my to do list to take 5 min per task to add. Maybe if I were to hire someone to set it all up for me, because I think the setup is making it very difficult to go in and load it up with tasks.

Maybe we even need to use a todo list software that integrates with a PM software to meet all of our needs.


Answer: Firstly, I love your persistence in wanting to nail your processes! You’ve tried many of the top project management tools and I can see how the limitations of these programs (in relation to your projects) have held you back:

  • Trello is great for planning but for managing more complex team projects, it can get out-of-hand quickly
  • Monday is a top choice for people looking for project management software that is easy for a team to learn but the structure does need to be set up properly for your team to benefit from using it
  • Basecamp is a great business management tool but can have limitations when you’re setting up a larger volume of projects and needing to handle varied permissions
  • TickTick is too simple for what you’re wanting to do
  • Evernote is a great tool for managing files for projects and I can see how you’ve turned it into a simple project management system but using Evernote tasks within their Notes Templates feature
  • ClickUp is an all-rounder but the amount of options and the UI does mean that people get overwhelmed by it for larger projects and teams

My advice would be to look at:

Option 1

  • Looking into using Asana and their reusable checklist feature for standard processes for video production and social media management
  • Set up Asana with teams being your 2 main divisions and have each project created using a reusable template under these teams
  • Combining the use of Asana with design proofing tools for video production (Dropbox also has a simple option for design proofing) and social media post scheduling tools like CoSchedule or Buffer.

Option 2

  • Look into using Pipedrive for sales management from your website (using their webform feature) through to onboarding and customer retention
  • Set up a social media pipeline, a video management pipeline and then set up pipelines for the complete process of production
  • Activities on each client project can be setup using Activities that are triggered upon each stage. You can also have emails triggered to notify clients of progress or ask for feedback
  • If you prefer not to use Activities or need to limit team access via permissions, perhaps have the project manager run the project through Pipedrive and have the production staff use a tool like Process St so that processes are followed each time (without needing access to the deal flow within Pipedrive)

I hope these options help.

About the author

Rich Peterson

I've spent the last 10 years planning, mapping & reimagining the processes of hundreds of SMBs. Whether the goal is more money, more time, more clarity or more customer smiles, my insightful process is worth every minute for my successful clients.
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