St. Francis, Dante, Michelangelo, Luther, and Kierkegaard were willing to challenge existing norms of their time. How was this helpful to them, and how is it now helpful to you in considering the meaning of life? Do you see any potential problems with their approaches in terms of finding meaning?
Saint Francis of Assisi
Saint Francis of Assisi, who might be said to have given into physiological complications from fevered illness, starvation, beating and imprisonment, might be said to have challenged the existing norms of his time by dishonoring his father, acting out in rage and isolating himself after hearing and harkening to a voice heard in dreams, sprung from fevered illness, which instructed him to do certain things, like return to his home and rebuild the abandoned chapel of St. Damian's below the town of Assisi. Francis more reasonably challenged the norms of his time by giving all the contents of purse, first, to a leper whom, after initially being repulsed, Francis embraced then provided for, and, second, at the tomb of St. Peter in Rome, where, dismayed at the pitiful offerings left by pilgrims to Saint Peter's tomb, Francis gave all he had with him. These experiences, some right and some wrong, knitted together to turn Francis into an evangelist bearing the message of Jesus Christ and into an inspiration for a handful of similarly zealous ascetics.
This was--eventually--helpful to Francis because he did give hope, charity and physical comfort to those who were in more need than he was while also taking the message of the truth of Jesus's Gospel to those he encountered while aided in the task by his disciple followers. This example may be helpful to you in considering the meaning of life in that it reveals and underscores that, for a consistently meaningful life, there is a right way and a wrong way to honor the call of God, a way that does not involve unthinking impetuosity that initiates irrational actions in the wake of illness and fever and that does not dishonor parents through theft of their goods while being a way that does honor Jesus's commands to love and to preach the Gospel and to give the metaphoric "widow's mite" and "cup of water" in Christ's name.
Dante Alighieri challenged the existing norms of his time by extending the prevailing into new currents of understanding. A good example of this is how he re-envisioned the concepts of love expressed by Guido--briefly, a “fierce accident” of passion--as a heavenly challenge to excellence: pursuing a lady's love is a test of virtue since her beauty, which reveals God's creative love, heralds true light and transcendent love.
Pursuit of the lady's favor has become a test, not just of nobility, but of virtue. Her beauty is perfect, the fullest possible exampling of nature's power to reveal God's creative love. ... Giovanna's beauty, [is] heralding the “true light” of Beatrice, just as Guido's poetry of earthly love is finally a foil to [Dante's] own celebration of the transcendent love revealed to him in Beatrice. ("Dante Alighieri," Stanford Encyclopedia of Philosophy)
This may have been helpful to Dante because it allowed to deeply understand the attributes of God, especially the attribute of love, and to discover how the previously separated disciplines of poetry, philosophy and religion meet together to enlighten a meaningful life without the previous subordination of one discipline to the other, without religion being given primacy over philosophy. It may be helpful to you in considering the meaning of life because, like Dante, you can think freely about possibly disparate subjects and find how they enlighten and inform each other while enlightening your conceptions of how to live a meaningful life.
Søren Kierkegaard challenged the existing norms of his time by devoting himself to critiquing Hegel and proving a broader basis for religious truths, which he thought Hegel had reduced to philosophy, thereby denying religious validity for the concepts of experience and faith.
This may have been helpful to Kierkegaard because it provide a means to re-emphasize the individual in opposition to Hegel's collective whole that subsumed the individual to restricted worth solely in terms of social value. This may be helpful to you in considering the meaning of life by encouraging you to critique the prevailing thoughts and paradigms of your times--for example the paradigm built on the concept that what is heard and seen, e.g., music, TV, movies, advertisements, do not do detriment to maturing minds and to groping adult minds--and participate in advocating a more rational concept and paradigm that, like Kierkegaard's notions, nurtures the value of the individual while reducing the power--subsuming the power--of the social unit.