In July of 1726, a young Benjamin Franklin set sail from London on an 11-week voyage to make a fresh start in Philadelphia.

Up this point he had been living a "somewhat confused" life led more by impulse than thoughtful intention.

This was a man who ran away from home at 17-years old, had been duped by the Governor of Philadelphia to travel to London on a false business venture, and made the poor decision of loaning money to a financially struggling friend before seducing that same man's girlfriend.

As you probably guessed, he never got his money back.

Franklin was ready to make some changes when he got home and had plenty of time out at sea to consider what he wanted to do with his life.

He wrote out a "Plan for Future Conduct" and imagined a new story of how his life would play out on his return. He resolved himself to "be extremely frugal" so he could pay back his debts, "to endeavor to speak truth in every instance," and to "apply (himself) industriously" to his work and business. His plan would take the longterm vision into consideration as he wrote, "industry and patience are the surest means of plenty."

The 20-year old Franklin imagined himself becoming a merchant and owning his own printing business. He wanted to marry and have children. He wanted to read, write, and contribute to the public domain of a burgeoning American identity that was starting to form in the British-controlled colonies.

With his plan in hand, Franklin was ready to play out his next chapter in life.

He started his printing business, got married, and created the Junto–a club of tradesmen and artisans that held discussion about politics, philosophy, and self-development.

Soon he took his planning to the next level by creating one of the earliest instances of a habit tracker for his "13 Virtues".

The biographer Walter Isaacson writes, "On the pages of a little notebook, he made a chart with seven red columns for the days of the week and thirteen rows labeled with his virtues. Infractions were marked with a black spot." He would focus on one virtue each week and "in the course of the year, he would complete the thirteen-week cycle four times."

Every milestone achievement gave Franklin the opportunity to reimagine the life he could build for himself. Eventually his printing business came to dominate the Philadelphia market and at 42-years old he retired from printmaking. A letter to his mother explains his motive, "I would rather have it said, 'He lived usefully,' than,'He died rich.'"

He had, of course, some plans in mind.

Franklin wanted to devote himself to his intellectual curiosities such as the sciences and politics. He started planning his days using one of the earliest known examples of time-boxing to create a structure for his free time so that he could use his time wisely in pursuit of what mattered to him.

With constraints on his schedule in place, he had the clarity he needed to let his imagination run free. This led to his famous experiments with electricity and the many practical inventions of his such as the Franklin stove.

When things didn't go as planned, he would adapt and shift directions. Whenever he was stuck or at a loss at what to do, he would go back to his notebooks and write to work out his ideas.

Franklin went through a life-long cycle of imagining new futures he wanted to move toward followed by rigorous execution. Thanks to his endless imagination and dedication to "industry" his life stands as one of the most accomplished and interesting stories in American history–and it all started with a plan.

Most people equate planning with productivity. It's almost as if to be organized with your time and plan your future means that you are a hyper-optimizer obsessed with metrics and getting stuff done.

But this view of planning completely ignores the most fundamental and basic purpose of creating a plan: to imagine how to get to a possible future.

It's the creative side of planning that stands out to me when I read about people like Ben Franklin. The ability to imagine how life could be different and come up with many different ways to to reach that grand vision is the goal, not checking off an endless to-do list.

Planning is a creative act, it requires imagination and the ability to see how one action might lead to another in a sequence. In other words, it's a narrative process–it's real life story-making.

Franklin's life stands out because of his ability to reinvent himself. It was a skill that he developed and practiced by planning throughout his lifetime aided by his instinct to clarify his ideas through writing.

Every time you sit down to make a plan for your day, you are training that imagination muscle. It may not seem like it, but that's what it is. You're literally looking into the future and imagining how your life story might play out. And when you turn to writing your thoughts down in your notebook, you're tapping in to that creative side of your mind to help clarify what direction you want to go in.

Yes, you will end up becoming more productive over time because you will learn to develop more effective plans. Plans create clarity about what matters to you and how to make time for what you deem important. With clarity, action becomes instinctive. The checkboxes and to-do lists are there to help, but aren't what ultimately matters.

The point of creating plans is to imagine possible paths that will lead you to what constitutes a good life–whatever the good life means to you.

For Franklin that meant pursuing his intellectual curiosities and embracing the public life of an American citizen.

It's up to you and your imagination to decide what it means for you.

Prompt:

Schedule a planning day in your calendar and spend some time imagining. Seasonal goals are appropriate at this time of year. A new month begins tomorrow and is a good time to imagine a fresh start. But feel free to use the planning session for any future projects or endeavors on your mind.

I recently set new annual and seasonal goals and found the process of imagining how the rest of the year will go immensely beneficial.

But remember to put the planning session on your calendar or it might never happen because in the words of Franklin himself, "Failing to plan is planning to fail!"