Nothing to do with lettuce

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Last week I was asked if I felt I was being myself wholeheartedly.

I had to answer no, because I am often filled with doubt and hesitation, but this is something that goes against the sort of person I want to be.  I want to live wholeheartedly, to take chances, to have faith in people, and in my future.  But how does wholeheartedness manifest in real-life practical terms?

whole·heart·ed, adjective, 1836

  1. completely and sincerely devoted, determined, or enthusiastic
  2. marked by complete earnest commitment, free from all reserve or hesitation


Synonyms: complete, committed, genuine, real, true, determined, earnest, warm, devoted, dedicated, enthusiastic, emphatic, hearty, heartfelt, zealous, unqualified, unstinting, unreserved, unfeigned
[The Free Dictionary]

Sure, I can read the definition.  I think I get pangs of the feeling of wholeheartedness.  But how do I move towards being more wholehearted in my day to day life?  (Not a rhetorical question, I'm looking for feedback here folks!)  How do you practice wholeheartedness in your life?