Oh-Sht Moments Career Calibration
Measure growth by counting the moments you felt underqualified and stretched.
- Difficulty
- Easy
- Time to result
- ~ongoing to results
- Steps
- 3
- Confidence
- 90%
A sharp reframe of the vague question 'am I growing?' into a countable one: how many moments in the last six months / year / two years made you feel underqualified and stretched, and what were they? A long dry spell of no such moments signals stalled growth worth digging into.
Origin
Shackleton picked this up from author Seth Godin and it stuck with him as a way to calibrate whether someone is genuinely growing in their career.
Core principles
- 01'Do you feel like you're growing?' is too ambiguous to answer honestly
- 02Discomfort and feeling underqualified are the signal of real stretch
- 03Growth can be counted as discrete stretch moments over a time window
- 04A long gap since the last stretch is a flag to investigate
How to run it
- 1
Reframe the growth question quantitatively
Replace 'am I growing?' with 'how many oh-sht moments have I had in the last six months, year, or two years — and what were they?'
Pro tip Naming the specific moments forces honesty the vague version can't.
Watch out Don't accept a hand-wavy 'yeah I'm growing'; demand the concrete instances.
- 2
Actively seek the stretch moments
Deliberately opt into situations where you feel underqualified or uncomfortable — they give you a new foundation. Throw yourself in the deep end, especially early in your career.
Pro tip Seek roles or tasks (public speaking, owning strategy) that force you to operate above your comfort.
Watch out Comfort for too long is the actual risk, not the discomfort.
- 3
Dig in when the well runs dry
If the honest answer is that it's been a long time since you were meaningfully stretched, treat that as a flag and investigate what needs to change.
Pro tip Use it as a periodic self-check or a one-on-one prompt with reports.
Watch out A comfortable stretch-free stretch of months is easy to rationalize; don't.
In the wild
Lenny recounts never wanting to do podcasts — he preferred typing newsletters — but did it precisely because it was hard and uncomfortable, an oh-sht moment he sought out.
→ He's glad he pushed into the discomfort, illustrating the framework's 'seek the stretch' principle.
Common mistakes
Asking 'do you feel like you're growing?'
The question is too ambiguous to answer usefully; people say yes reflexively and no real signal emerges. Counting concrete stretch moments is far sharper.
Avoiding discomfort to protect competence
Staying only in situations where you're fully qualified feels safe but means no new foundation is being built — the absence of oh-sht moments is the warning sign.
Is it for you?
Best for
Individuals and managers wanting a concrete gauge of career growth instead of a vague feeling
Not ideal for
Someone already overwhelmed or burned out who needs stability rather than more stretch
From the transcript
“I picked this up originally from Seth Goden”
“those are the moments you should be seeking out right like those are the moments that stretch you”
From the episode
What sets great teams apart
Lane Shackleton (CPO of Coda)