The Learning Pit & Leveling Up
Many of us have career – or better yet – life defining periods of time. I don’t want to say “moments” because that’s misleading. There aren’t many singular moments that change everything in a flash. Most of them build slowly and steadily until there’s a long-last peak “aha.” And in my career, one of those many moments was learning about the Learning Pit.
Ivy Kusinga of Career Vines first taught me about about James Nottingham’s Learning Pit about 15 years ago in a leadership offsite. It’s one of those key learning moments that’s become so cemented in me, it’s an invisible cornerstone of my growth mindset and career growth. I can still flash back and see the doodle on the flip chart that looked something like this:

Paraphrased, the idea is: as fallible, optimistic humans we assume that growth is linear. We accept that yes, one must begin at the base of the “mountain” and work hard to climb their way to the top. But we neglect one important, life-altering detail: on the way up, there will be many dips and pits along the way. We’ll go up and drop down again. Gain a little more altitude and then fall. Over and over again.
And here’s the kicker: I’ve learned (the hard way, through many pits!) that especially when working with high achievers, the Learning Pit is harder for them. Many quit. Right before they actually get the benefit of the growth.
We (all of us!) try to skip over the Learning Pit. And why wouldn’t we? It hurts. Badly. It requires trusting the process. Having your eye on the long game. I’d even go so far as to say: it requires taking a Buddhist approach to business.
A few years ago, Ivy presented this teaching in our Client Appreciation Event. At the day’s closing, we round-robined highs, lows, and (a)has. I was pleased that the Learning Pit was so many clients’ ahas and (to my surprise): their high of the day. They loved that there was finally an explanation – an image even! – to describe one’s perpetual state and feelings of both elation and frustration as an entrepreneur. We’re nearly always (myself included) in the f****** learning pit!
After that teaching, a client recapped their takeaway for me:
The people who learn to work through the pits (over and over again) are the ones who achieve true mastery. If you’re a quick learner and are always on to the next thing, you’re not deeply a master. Learning how to learn and how to trust the process of learning is one of the greatest life skills one can have.
Clients and students come to Ellevated Outcomes because they want to level up their business. Heck: colleagues join our team because they want to level up their career.
But the thing they don’t tell you in school (or life) is: to level up – to reach new heights – requires going through, falling back, into the Learning Pit. Over and over and over again. Or as Ivy concluded:
High performance in business demands an ability to go in the pit.
Exist in the pit.
Sit in the pit.
Then, deal with the pit and get out of it.


