Hi there,
So far this week, you’ve looked at what surprised you in a good way, and what quietly drained your energy without paying you back.
Today, we’re staying in observation mode, but shifting the lens again.
Note: I’m still reading all of your replies (I’m loving them!) but I’ll be a bit slower over the coming days as I’m getting surgery this morning. Can’t wait to see what you share for the remainder of the week!
Week 1: Looking back
This week is about spotting patterns before we try to change anything. Not judging past decisions. Not fixing. Just noticing.
Week 1, Day 3: Where leadership felt easier or harder than you expected
Looking back over the past year, where did leadership feel lighter than you thought it would? And where did it feel heavier than you expected?
This might show up as:
work that felt easier once you started doing it
responsibilities you assumed would energize you but didn’t
situations that consistently felt more draining than they “should”
moments where you were more effective than you gave yourself credit for
You’re not trying to explain why yet. Just name where things felt smoother or stickier than expected.
Often, ease and friction are signals about how you actually work best, not how you think you should.
My example
Heavier: Finding my confidence in a new role. Despite writing and teaching about leadership confidence, I struggled more than I expected to find my footing. I second-guessed decisions and caught myself seeking validation from my manager more often than I’d like, which was both surprising and humbling.
Lighter: Stepping into interim roles wherever the business needed me. At both my previous and current company, I was able to flex quickly, whether that meant temporarily EM-ing an additional team or putting on a large product leadership hat. Adapting in the moment came more naturally than I expected. (I do, however, have a small head.)
How to complete today’s prompt
If replying to the email helps with accountability, hit reply and jot down your answer.
If you’d rather keep this private, write it down somewhere just for you.
There’s no perfect answer here. A rough sentence is enough.
Tomorrow, we’ll examine what “worked” but may have taken more out of you than it gave back.
Onward,
Kelly
Missed a day or starting late? You can find all challenge prompts here.