Ep. 19: Calendar Shaming, Digital Detox Struggles, and the Unexpected Challenges of Autonomy | DEEP QUESTIONS

In this episode of Deep Questions I answer reader questions on calendar shaming, digital detox struggles, and the unexpected challenges of gaining more professional autonomy, among many other topics.

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Here’s the full list of topics tackled in today’s episode along with the timestamps:

WORK QUESTIONS

* Modernizing GTD [2:18] * Calendar Shaming [7:59] * How I keep track of projects [14:15] * Staying relevant when less connected [16:29] * The inherent unpredictability of kids and facing the productivity dragon [19:21] * Quantifying career capital [25:09]

AUDIO QUESTION OF THE DAY [28:17]

TECHNOLOGY QUESTIONS

* Dealing with screen time overload [31:36] * Is a Kindle a screen? [36:32] * The relative depth of books versus podcasts [36.48] * Digital detox struggles [39:26] * Instagram struggles (hint: my suggestion starts with a ‘Q’ and rhymes with ‘bit’) [44:02]

QUESTION ROULLETE [45:49]

DEEP LIFE QUESTIONS

* Interviewing people you want to emulate [49:04] * Dealing with psychological hurdles such as negative self-talk and impostor syndrome [54:30] * Learning hard things fast [1:03:53] * Vitamin solitude [1:05:24] * The challenges of autonomy [1:07:54] * Understanding those upset by depth [1:11:05]

Thanks to listener Jay Kerstens for the intro music.