Are you weighing the trade-offs of a big career decision? Dan and Alison answer your questions with the help of Claudio Fernández-Aráoz, a senior adviser at the executive search firm Egon Zehnder. They talk through what to do when you want to transition from individual contributor to management, you’re mulling over a more senior role at a smaller organization, or you’re having doubts about staying on a high-pressure career track.

From Alison and Dan’s reading list:

HBR: Make Peace with Your Unlived Life by Manfred F. R. Kets de Vries— “Tina was at a crossroads. Her daughter had recently left for college, and her husband had his own pursuits. And although she’d once enjoyed banking, she now bore little interest in her work. For some time, she had been asking herself whether she should quit. But what would her colleagues and bosses think of her?”

HBR: The Key to Career Growth: Surround Yourself with People Who Will Push You by Claudio Fernández-Aráoz — “Don’t hesitate to ask the truly big questions. What shall I do with my life? What really motivates me? What am I doing that I really don’t like to do? While pondering these questions, in addition to checking my capability, connectivity and credibility, I also engage my friends in conversation about three other Cs: contemplation (Am I in touch with my inner compass?), compassion (Do I show it for myself and others?), and companions (Who else might inspire me to new growth?)”

HBR: How to Stay Stuck in the Wrong Career by Herminia Ibarra — “We like to think that the key to a successful career change is knowing what we want to do next, then using that knowledge to guide our actions. But studying people in the throes of the career change process (as opposed to afterward, when hindsight is always 20/20) led me to a startling conclusion: Change actually happens the other way around. Doing comes first, knowing second.”

HBR: How Star Women Build Portable Skills by Boris Groysberg — “After studying the fortunes of more than 1,000 star stock analysts, we found that when a star switches companies, not only does his performance plunge, but so does the market value of his new company. What’s more, these players don’t tend to stay with their new organizations for very long, despite the generous pay packages that lured them in. Everybody loses out.”