Square peg, meet round hole.

Frustrated lately with project management systems, both on the web and applications on my Mac. There’s a disconnect between this cloud we keep trying to work in and our actual work. I have information scattered across too many systems, and too many places for it to be considered useful.

I am not trained as a project manager. I did not go to school for what I do now (gasp!), nor did I study business management. There may be a component of my troubles here that tie into a lack of some specific skill, but I doubt it. I have a feeling it is more about how creators of these tools see the way they think people should work.

If you look at the two major OS’s that I work on, iOS and OS X, there are some very impressive project management tools available. Impressive in their UI, impressive in their sales, and impressive in their marketing schtick selling them as PM tools. But truthfully, they are almost all just glorified task apps. Todo lists all of them.

Here is where the disconnect happens. I have work to do. Much of it involves completing tasks, many of which have to be done in certain order and in certain time-frames. They almost all involve clients, websites, emails, meeting times, phone calls, and any number of other project meta data. I do not need a task application. I need a way to see through all this, track all this, and form it all into completed project work. I need a way to archive it, and reference it again in the future.

I need an something that does the following:

• Combine a PM and CRM tool into one. My clients are not contacts, but a vital part of my workflow.
• Allow me to track my work information in many formats. Project meta data, notes, milestones, tasks, all wrapped around into project.
• Show me relevant information from current and previous other projects that may pertain to this project. Smart info.
•  Track important date-based information and remind me in time to make it happen.
•  Let’s me share files easily (for me and my clients), with simple permissions (I’m a sole proprietor, remember?).
• I need this on the web, not on my Mac.

Note: I’m posting this well after writing it. Since writing this, I’ve found some tools that have come close to what I need, but thought this would make a good starting point.