Choice overload

I don’t seem to have issues finding flow. I guess I’m lucky like that. I don’t have any problems delving into a problem for hours on end and really disappearing into it. I seem to have a different kind of problem. Focus. It’s a situation where I find myself with too many options and I’m not sure what to do next. I guess it borders on feeling overwhelmed, but I don’t really feel that stress. The only thing that stresses me is the feeling of the immediate, the reacting. As one that works in support, I call it firefighting, those situations where something is broken, a server down, or some other critical application or service that brings me out of flow and forces me to go from what I want to do to what I have to do. Sometimes these situations are self inflicted, but other times they’re just disasters. A virus on a client server that brings them to a standstill, and requires my full undivided attention until the issue is resolved. These are the only moments in my life when I’m truly stressed.

The other problem I struggle with is deciding what to do next. It’s probably a prioritization issue, and I’m either ignoring my list of todos or otherwise procrastinating. I pulled out my copy of David Allen’s Getting Things Done and skimmed through the first third. I read it years ago and tried to implement some of it as a best practice, but I’ve struggled to really find something that works. I started using index cards for the wife and I to keep track of things. We’ve tried Trello in the past, but she didn’t really stick with it. I personally found Nirvana to be the most pleasant for me, but I quickly ran up against the limits of the free plan. Of course when I do pay for something, I quickly forget about it, and once I’m reminded about the bill and cancel the service, I start using it again.

The golden age of apps that we currently live in presents more and more of a choice paralysis for me. My various clients have their own stack, but it seems like every new startup has their own, and I seem to get bogged down in figuring out what works, what’s new, how to manage it, and most importantly, how to get buy in from the team. I could think of dozens of examples, the choices are everywhere. As someone who makes their professional calling as the ‘trusted advisor’, I get lost in a sea of possibilities. It’s hardest when you’re planning a new organization, or one that is using a lot of manual and paper processes.

In the past, it’s been trivial to take a few simple steps to get an organization moving along. A few examples: creating mailing lists where the organizer was using personal email; Setting up Google Apps for email and file sharing; registering a domain and setting up a basic website. But the longer I go on with this, the harder it’s proving to nail my preferences down to a few apps. And depending on the organization, it’s proving almost impossible to get buy in from everyone. I have one volunteer group I’m part of where they still insist on massive group chats. I recommend Signal, and things go nowhere. Trello, or Asana for task management, and everything falls off after a few weeks. The more involved I get with an org, the more convoluted things get. Having different apps for time tracking, billing, CRM, issue logs, and so on and on just gets cumbersome. Having these apps talk to each other is nice, but trying to design a solution over and over again is just sapping the energy out of me.

Which is how I found myself playing around with Basecamp last night. I need a system that I can use for my freelance work, that will allow me to add clients as needed and allow me to collaborate with them and their clients. I’m not saying that it’s the answer, but it does seem to do a lot of what I think is needed within a team. It doesn’t do it all, and I’m not sure that it’s best at all of these things, but I’ll settle for simplicity right now. What I need is less options, so that I can get back to work, and stay in flow. I need something with which I can track tasks, assignments, time entries, billing, documentation, source code if need be. There’s just too many solutions out there, and at some level it seems like some sort of entrepreneurial masterbation to be messing around with all of this crap.

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