Project management tricks for a fulfilling life

Do less of what you dislike, alright? You don’t have to do those things.

A preview of practical advice:

A preview of opinions:


What is a fulfilling life?

I don’t know. It’s one in which we have holiday house parties and birthday parties and wedding parties and go on vacation together and rent a car or a house, or go canoeing. Or maybe we write plays and create a theatre and build an earthship or run an art gallery and have shows in our basement or make a band together and anonymously publish a zine and run a bike shop that also shows local art.

A fulfilling life can happen in many ways, and not just through the ideas that I’ll talk about. But I know that a lot of these tasks require a large amount of logistics for the promised payoff, and if it’s too large, we become less likely to do the things we want.

Communicating effectively and efficiently are the uninteresting words that help get the interesting things done. But, they make room for us to do the beautiful things.

Bad Habits

Depending on how you’ve spent your adult life, you are accustomed to the idea that creating forms and paperwork and emails is how you Get Things Done. Some big event coming up? Start emailing all involved over travel details first, then event details, then after-event details once the day is happening. Easy peasy! All in one place!

First, I’ll identify the negatives of email.

  1. An email chain is a document that becomes outdated the moment someone responds to it.
  2. An email chain requires each reader to visualize the status of the project, the responsibilities, the sequence of events, etc.
  3. Participants must start with the first (now-outdated) document to recreate the sequence of decisions, quickly committing to memory and forgetting many states of the task.
  4. Email writing fatigue. How’s your grammar? How’s your tone?

Second, I’ll identify the positives of email.

  1. You can contact someone you don’t know, or know only in a professional setting, in a professional way.
  2. You can alert someone that something has changed, if you have not connected in some other chatting mechanism.

You get the idea. It’s hard to change workplace culture, but you don’t have to bring those habits with you into your own life.

Good Habits and a Shift of Mindset

Imagine standing in the front of a room. Twenty of your closest friends stand in a line because they have all come to tell you something. There are 4 different things going on this month, and they are telling you in a sequence what the decisions of the group are. By the end, you remember everything you were told but slightly out of order. Where did we end up deciding to go? What was I supposed to bring? Is someone waiting on me to do something? Do I have to get groceries tonight?

Now imagine entering a room with 4 tables in it, each labeled with a banner above it according to their subject matter. You stroll up to one table, and you see the name of the location and the time. Someone comes up and switches out the time for something else, and gets rid of the old time.

Maybe it’s just me, but one of those seems easier to keep track of.

The first is email. The second is, oh, let’s say a Facebook event.

This shift in mindset is what it means to gather around the Thing Being Done. It’s kept up to date with only the relevant information. A newcomer can come around to see, straightforwardly, what’s left to be done.

It allows for us to think about the things that actually matter.

Finding Tools for the Job

Need to talk? If possible, chat in some way that has less overhead than email. No one needs the Dears and Thank yous. Facebook messenger, Slack, Whatsapp, IRC, I don’t care. Use what feels easy.

Need to track to-dos? There are several tools. I’ve used Google Sheets (good for small events, one-offs). I’ve used Trello (good for a one-time semi-complex project). I’ve used LeanKit (a previous employer; very sophisticated; good for continuous projects).

Need to plan a time for many people to meet? Use something like WhenIsGood to get rid of the headache of figuring out who is and isn’t available when. Need to poll lots of people quickly? Find one that does it for you.

You get the idea.

Figure out what it is you’re trying to do, really, and use something that makes it easy. Most of these companies operate on the freemium business model, which is great for individuals or small groups. Some of them (like, WhenIsGood) don’t even require you to create an account.

Do the Work Along the Way

First, separate whether to do something from how we’ll do something. I’ve seen conversations get mired in details like Where and When and How before everyone in the party even agreed to doing the thing to begin with, which made any decisions arrived at hypothetical in nature (and every decision to be renegotiated in the face of reality).

Set quick deadlines for small tasks. Set a deadline for considering whether to do the thing. Set a deadline for considering how to do the thing. Set a deadline for people claiming responsibility for something. Meet the deadlines and move on.

Keep chatter to a minimum. There’s such a thing as “analysis paralysis,” something I personally suffer from. Chatter long enough to lay the cards on the table, but arrive at a decision.

Have Feelings Along the Way

These tools help communicate to everyone involved what’s going on and Who needs to contribute What to the end goal. However, there’s usually still a boss-person, even between friends, who will feel the responsibility for poking the thing along.

To those who do not take this role, be grateful for the willingness of the boss-person. Do your best not to require reminders. Trade off and take the job sometimes, if you notice it’s always the same person.

To those who take this role, it will be painful if you have any kind of sensitivity to not wanting to bother others, or to seem intrusive or demanding. Be aware of this when you’re telling yourself to hold off on talking to someone about something because you want to respect their space. They probably needed the reminder. We all live complicated lives.

Keep Going

Finish the thing, and plan toward the next thing. The better you get at this, the more fun the planning process gets. Work with your friends, and work with good people. Just remember not to waste your time on the brain-numbing stuff.