| 1 | Facing and Overcoming Failure | 32.4 |
| 2 | Navigating Deep Relationships (and Heartbreak) | 17.3 |
| 3 | Getting Roasted by Users (Failure as the Best Teacher) | 16.5 |
| 4 | Experiencing Loss or Grief | 15.3 |
| 5 | Taking on Significant Responsibility | 15.2 |
| 6 | Leaving a familiar environment | 13.9 |
| 7 | The Weight of Complexity | 13.0 |
| 8 | Hard conversations and boundary-setting | 11.5 |
| 9 | illness | 10.5 |
| 10 | Find a Mentor or Peer Coach | 10.5 |