
This is a guest post from Jesse Phillips—I think his new calendar is a really smart tool that you should think about buying.
“If you fail to plan, you plan to fail”
Planning is an after thought. It’s work we put off—so we forget stuff, we get lazy, we prioritize the urgent over the important, we often don’t think & plan something out.
So when it comes time to pay the bill, make the decision, or turn-in the report—too often many of us fall short.
Great things don’t just happen! Your house did not just appear on a whim. Your iPhone did not invent itself. Your company does not hope for a good product & customers – it plans for it. All that to say…
PLANNING IS ESSENTIAL TO SUCCESS
Look, not ALL things require planning. You don’t have to plan to eat ice cream – you want to do that. But complex or difficult things DO require planning. Things like projects, writing a book, holding an event – things with many moving parts.
Some friends and I recently put on a big networking event. We had lots of things to plan: find a venue, procure sponsors, decide on food, create and execute a marketing plan, partnerships, website, emails, etc, etc. This event never would have happened without making several, related decisions.
PLANNING IS MAKING DECISIONS
That’s all planning is, making decisions ahead of time, deciding a path, deciding a cut-off. Looking at your options & many necessary decisions, seeing how they affect one another, and deciding accordingly.
Therefore, clearly, nothing interesting is likely to happen unless it is planned-out. Your book will go unwritten, unless you make a plan to write it. Your project will go unfinished, your vacation un-enjoyed, your dream unrealized – without planning.
HOW TO PLAN
Planning is not so hard as we make it. It requires thinking, weighing options & deciding (execution is the hard work, but it’s MUCH EASIER WITH PLANNING!). The main challenge with planning is not getting overwhelmed by the size of whatever you’re trying to do. The ambiguous project will often discourage me & I’ll avoid it. But when it’s planned out, decided, I have a much easier time doing it. Here’s an easy method I used to plan my projects:
- On a piece of paper, write down the name of the project and the deadline.
- Under it, brainstorm the various components – discrete areas of tasks that must be completed to accomplish the project. Like for our event: Marketing, Venue, Invitations, Food, etc. And make buckets of tasks under those areas.
- Now having a sense of the scope of the project, get a calendar, put your deadline on there. Looking at how much time you have, make sub deadlines for each of your buckets. For example: Fliers must be printed 4 weeks out (so they must be designed 6 weeks out). The flier will say the venue, so it should also be decided 6 weeks out.
Now that you have tasks & deadlines, you can get to work! This is a whole nother subject, but your work is much easier now that it’s planned!
RIGHT TOOLS FOR THE JOB
Speaking of planning, having done much of it, I’ve found myself wanting some better tools for planning – specifically a better calendar. I’ve wanted something bigger, showing me the whole year clearly, that’s easier to plan across months, and that looks nice.
In an effort to address those problems & help fellow planners everywhere, I’ve designed a calendar to meet all of my above requirements. And I’ve launched it on Kickstarter.

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