Barack Obama remains in the public mind as a transformative President. However, not too many know that he shares his time and space with countless minds, such as Lincoln, Mandela and Gandhi, his heroes. He once said: “So, sometimes you have to sort of hop across history to find folks …”

How did he find kinship with people and events from other eras?

Through the word. Obama shared ideas and found visions reflected and refracted in other greats through a continuous habit of self-reflection and journaling.

Obama kept diaries in the White House, though not with the sort of discipline that he would have hoped for”, he once admitted. Still, reading about others and writing about his own self-reflection made him learn from as well as reach out to intellects and thinkers. His journals captured the timeline of his mental and intellectual evolution.

He once admitted to Time that he kept a diary to help clarify his thoughts.

How Barack Obama keeps his journal

The diary became an important metaphor of Obama’s life. Through the years, the highlights of his public life were a hectic series of events, policy deals, decisions and drives. However, his private one was comprised of intensive reading and writing that were self-reflections.

For instance, he once wrote: “Operation SCOTUS will take time, but I’m young. First step is a law school gig— Harvard will still love me even if I lose—then I wait for Joe or Hillary to beat Mitt. Those two owe me.”

He will be remembered as a visionary Democrat who increased the moderate tax, reduced income inequality and introduced an impressive health care system. He has also left a stamp on the future by authoring six books and by being the only sitting President to publish an academic paper on healthcare reform.

Still, it is his inner self richly reflected in the diaries that drove his vision. They record his continuous stream of consciousness and his subterranean mental and intellectual evolution through self-reflection.

How long has Obama been doing it?

Diarying began when, as a young, Chicago community organizer, Obama taught himself to write by journaling about his days as well as weaving short stories around the people he met.

Every evening after returning from work, he would sit down to self-reflect by penning down the events as well as accompanying emotions.

His writing was lucid and empathetic. Over the years, he grew the ‘story’ metaphor to understand and empathise with people, record them in his journals, and weave them into short stories.

The leaks

Hence, it went beyond being a record of events. It was about “The personal feeling, the idea, coloured his journaling…”, as Time puts it.

That is very evident when you look at some of his entries. For instance, ‘Elle’ published some “leaked” diary secrets, in which his continuous back-and-forth toggling is evident.

For instance, in the diary of 2012, “What if I lose?”, he gives raw, informal, and unabashedly self-absorbed entries:

There are voices, tones, and nuances that are rushed through the prism of the diary. They refract his multiple thoughts and emotions, standing in the present but also making him rove through other timelines, making him assess and weigh options.

How self-reflection helped Obama achieve his success?

Interestingly, Obama started life with an emotional handicap. His persona was that of an ‘outsider’ as his father was from Kenya and left him when he was just two years. His mother was from Kansas, and took him to live for a time in Indonesia. He missed his father, and that sense of loneliness and separation made him empathetic towards dislocates.

But, having a strong desire for self-awareness and self-reflection always helped him arrive at fresh solutions and find positivity in life.

What challenges has Obama faced?

When he took over the Presidency, his biggest challenges were more objective: the war, the environment, healthcare, and the economy.

Reading and writing made him “slow down and get perspective,” which gave him “the ability to get in somebody else’s shoes.” However, he admitted: “Whether they’ve made me a better president I can’t say.” Still, they let him maintain a balance during his tenure, as he looked at it as a place that “comes at you hard and fast and doesn’t let up.”.

It made him self-reflect, comprehend the everyday world and grapple with existential issues. He connected the dots to understand the continuum of life, history, and its meanings and arrive at solutions in the White House.

What does the future hold for Obama?

Tomorrow, and tomorrow, and tomorrow…

Today, having graduated into becoming the “former’ American President from the “44th one”, Barack Obama still has not let up on journaling and reflecting about his future. Though his net worth today is estimated to be $40 million, his diary entries show him ruminating through different options – golfer, actor or teacher.

Still, writing is definitely big in his plans … because it always has been. In one entry he makes it clear: Writing books; OK, this I’ll do no matter what.

How can you get started with self-reflection?

So, did journaling help Obama to become President?

Who knows – but it definitely helped him to practice self-reflection, clarify his thoughts and act.