Want to start before you're ready? Plan to not feel ready

If you want to "start before you're ready," plan for the you that doesn't feel ready. If you want to "do it scared," design a system for the you that feels scared.

This is what we talked about for the last 20 minutes or so of Big Paper Planning Day last Sunday. After spending the day together dreaming and planning and studying the science of motivation, a question appeared: How do I know if I'm ready to pursue this goal?

At Big Paper Planning Day, we employ a version of the 12 week year—a concept coined by Brian P. Moran and Michael Lennington that essentially boils down to "What if you get a new year (and all of the rituals and excitement that come along with it) every 12 weeks, instead of just once a year in January?

The 12 week year offers us a constraint. Constraints are good for creativity, provided we have space first to think divergently, without naysaying or judgement on the basis of "practicality." 

When we're in the divergent thinking stage, we don't want the hole-poker in the room yet. Once we've got a whole bunch of ideas on the board, however, limiting the scope of the problem and being realistic about our resourcing empowers us to be more creative with our solutions. (My personal theory is that this is why we're often so innovative when broke as shit.)

Here's a classic example from Odyssey of the Mind, a creative problem-solving program I participated in as a child.

Your challenge is to come up with a way to transport a small, shoebox sized container from one side of a river to another.

You'll likely begin with divergent thinking: How might this be possible? Chance are, your answers will include lots of solutions that look and sound like "build a boat."

But what happens when I add a constraint?

What if, for example, I tell you that your solution cannot use wood? Or maybe even that it cannot resemble a "boat" at all?

 Give this problem to a group of elementary school children, as they do in Odyssey of the Mind club meetings, and you will see true uninhibited creative thinking at work. Suddenly, we're getting this container across the river by inflating a giant rubber ducky or creating a pulley system with the tree branches overhead.

This creative, innovative thinking is also what happens when we add a constraint to our life planning—when, after divergently exploring all of our options and desires, we ask the question "What might be possible in the next 12 weeks?"

Condensing the scope of the problem prompts us to think more creatively about what actions are currently within reach. It's a practice in convergent thinking.

At the same time, adding this constraint can bring up some doubt and insecurity—particularly if we have a goal that feels intimidating or far away.

One solution is to abstract the goal, which is the primary skill we practice at Big Paper Planning Day. I do not intend to start a family in the next 12 weeks, but there are countless other ways I can "foster connection with my family" or "help steward the next generation." 

If I'm able to recognize that these abstract desires are ultimately what's underneath my specific and concrete goal, I can then come up with all sorts of ways to get what I want—even within a constrained period of time.

Which brings me back to "starting before you're ready" or "doing it scared." It may be true that you feel far away from one of your concrete goals or not quite ready to pursue it. Maybe you don't have the resources yet to buy that house with a backyard garden library, or you feel afraid to leave your stable paycheck and start working on your business full time.

What I want you to see is that these, too, are constraints. Not feeling ready or feeling scared to try are opportunities to be significantly more creative when planning your life. Recognizing these feelings is not only a step toward self-compassion, it's also an essential part of innovation.

What does it look like to create an action plan for the you that exists in the here and now, with the resources and skills and messy human feelings you currently have—instead of planning for an idealized version of you that "has it all figured out"?

How might we bridge the gap between where you are and where you want to be while also accommodating your needs in this moment?

These are, fundamentally, design questions. They are easier to answer if you're already a divergent thinker who is constantly full of good ideas. Lucky you!

If you want a step by step process for practicing these skills, abstracting your goals and creating action plans that actually make sense for YOU, I'm excited to share that you can now host yourself a Big Paper Planning Day thanks to the brand new DIY version of our beloved quarterly planning retreat! 

After buying, your least complicated next step is to go school supply shopping. How fun is that?

Bored on the Internet?

✷ Check out TIME's 200 best inventions of 2023! If you're extra bored, analyze them: What problem does each of these inventions solve? What story are they telling about why it matters?

✷ Residencies for writers! Residencies for writers for days!

✷ I'm curious about this tool for collecting feedback and testimonials via voice notes and short videos.

⚛ Mini Lab: Tools, Trends & Experimental Ideas ⚛

What are you selling?

Who is it for?

Why does it matter?

How does it work?

How do people pay for it?

If you can't clearly and confidently answer these questions, you have what I would identify as an Offer Design problem. Luckily, this is a creative problem—one with an infinite number of possible answers and solutions.

By taking the time to solve it, you open up the door to true innovation in both your product/service offerings AND your marketing strategy.

You can experiment on your own and try to find the answer: Sit down sometime today with a sheet of paper or a blank Notion page and practice responding to each question.

If you get stuck or want an extra hand, you can now officially book a 1:1 Offer Design session with me. In this 2 hour collaborative workshop, we'll brainstorm together on a digital whiteboard (or a real one if you meet me in D.C.)

By the end of your Offer Design consulting session, you'll have a renewed sense of conviction when talking about the value of your work and a whole lot of new ideas about how you might support and delight your people.