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5 Questions to ask yourself:
1. Where in your life or your work are you currently pursuing comfort, when what's called for is a little discomfort?
James Hollis recommends asking of every significant decision in life: “Does this choice diminish me, or enlarge me?” ... you usually know, intuitively, whether remaining in a relationship or job would present the kind of challenges that will help you grow as a person (enlargement) or the kind that will cause your soul to shrivel with every passing week (diminishment). Choose uncomfortable enlargement over comfortable diminishment whenever you can.
2. Are you holding yourself to, and judging yourself by, standards of productivity or performance that are impossible to meet?
What would you do differently with your time, today, if you knew in your bones that salvation was never coming—that your standards had been unreachable all along, and that you'll therefore never manage to make time for all you hoped you might? ... let your impossible standards crash to the ground. Then pick a few meaningful tasks from the rubble and get started on them today.
3. In what ways have you yet to accept the fact that you are who you are, not the person you think you ought to be?
The attempt to attain security by justifying your existence, it turns out, was both futile and unnecessary all along. Futile because life will always feel uncertain and out of your control. And unnecessary because, in consequence, there's no point in waiting to live until you've achieved validation from someone or something else.
4. In which areas of life are you still holding back until you feel like you know what you're doing?
It's easy to spend years treating your life as a dress rehearsal on the rationale that what you're doing, for the time being, is acquiring the skills and experience that will permit you to assume authoritative control of things later on. But I sometimes think of my journey through adulthood to date as one of incrementally discovering the truth that there is no institution, no walk of life, in which everyone isn't just winging it, all the time.
5. How would you spend your days differently if you didn't care so much about seeing your actions reach fruition?
... it's worth asking: What actions—what acts of generosity or care for the world, what ambitious schemes or investments in the distant future—might it be meaningful to undertake today, if you could come to terms with never seeing the results?
Excerpts From: Oliver Burkeman. “Four Thousand Weeks.”