When Good Enough Feels Off.

The Toronto Reference Library (where this morning’s keynote took place). © Jordan Nahmias.

On Tuesday morning, I asked a room of 250+ smart, caffeinated adults to make deep eye contact with a stranger. Predictably, a few of us (me included) had the same thought: This is awkward. Please stop.

This was part of a keynote that I delivered for the annual Counselwell Summit, a gathering of many of the best and brightest in-house counsel in these parts.

It was fun. It was challenging. It was interesting to see how people reacted to what I was saying, and perhaps more importantly, to hear what had come up for them as we went through the session.

The session was about the Inner Critic - certainly, a trendy topic in certain circles - but I don’t think that makes it any less valid or relevant for my audience. The work was not to mute it, but to notice it and go on anyway.

Afterwards, a dozen conversations reminded me why it’s worth it: when we show up, we connect. When we connect, we grow.

In case you missed it and want to get a sense of what we worked with, I’ve made a number of tools available here for free download.

In that spirit, here are a few pieces of writing and listening that helped me work with my own inner critic this week, not against him. They’re short, potent, and useful if you’re building a life and career on purpose.


Overcoming the Self Through Public Speaking

Entirely coincidentally, on my way to the keynote this morning, I was listening to Sam Harris’ podcast and he brought up this article he had written years ago about public speaking - The Silent Crowd.

I hadn’t read this before, or even heard of it.

Now, think what you will about Sam Harris - he can be divisive - but, this article hit the nail on the head for me.

Because, the thing he talks about - the fundamental thing he gets to in the essay (which, I can not do justice given his writing is just so much clearer than mine) - is that, we just need to do the thing that scares us.

And this was so much a part of the keynote I was delivering. That, yes - that voice in our heads is going to give us a hard time about doing certain things - it’s going to hold us back so that we stay safe. Safe from what?

What we’re afraid of doing. Specifically, of not doing that thing well.

He goes into much more detail on the topic, but I think that, for anyone who is contemplating or doing any public speaking, or for those of us who just know there is something we want or need to do, but are slightly afraid of the outcomes - it’s a great read.


Hesse’s Steppenwolf

Last week, I started reading Steppenwolf by Hermann Hesse - a book that I’d been meaning to read for a while. I read Siddartha in high school - which may be a bit cliche, but then again, totally checks out for the guy who is always looking to understand himself more. (While we’re at it, add Kafka’s Metamorphosis to this list too).

Steppenwolf feels a bit different though. It’s basically the story of a guy named Harry Haller (a not so subtle cover name for the author’s), who is battling between his civilized, orderly self and his wild, instinctual one (i.e. the wolf).

This might be another coincidence entirely, but in reading it, I see it less as a story of torment and more as an early meditation on the Inner Critic: the friction between who we think we should be and the parts of ourselves we’ve exiled. Hesse’s point, if you read between the lines, isn’t to kill off the wolf or silence the man — it’s to let them, somehow, both live. But how?


You’ve Built a Great Life. So Why does it Still Feel “off”?

This is something that I get from clients all the time. In fact, I would say it is one of the top 5 sentiments that people express to me. “Things are great on paper, but I dunno - something is just amiss, and I can’t figure out what it is or why.”

Work? Maybe.

Home? Maybe.

I think it’s something else though - it’s peoples’ way of being with the things that come up at work or at home.

Most of us have become world-class problem solvers - experts at “fixing.” That is, in fact, my biggest hangup around coaching and therapy - that it implores us to fix things, when in fact, things probably are just fine.

But then where does the urge to fix come in?

When something feels off, we immediately start poking and prodding: new job? new project? new therapist? But sometimes the itch isn’t asking to be scratched. Maybe, instead, it’s just asking to be looked at or listened to.

Now, I’m not advocating being entirely passive or nihilistic. But, it’s like when you give someone advice, and they say, “Hey - I really just wanted you to hear me out.” (At least I get this sometimes…). In other words, it’s less about changing the furniture and more about changing the way we sit in the room.

What if the “off” feeling isn’t a signal that something’s wrong, but that something simply wants some attention? Not optimization - curiosity. Maybe what’s “off” isn’t really anything at all - it’s just how you’re seeing it at the moment - and that will pass.


I work with people - teams and individuals - to figure out what’s holding them back from what they want to do, where they want to go, and who they want to be.

To get Unstuck.

Want to talk about where you’re stuck? Get in touch.

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