Sanity Notes #002 : What if you could not fail?

How might you be free to lead and create if your own sense of self was not on the line?

Matt Munson
2 min readDec 1, 2022

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Many leaders I sit with are carrying big questions about whether or not they are enough.

This question is a part of my internal programming as well; I have wrestled with it since childhood.

While I have heard it argued it benefits entrepreneurs and leaders to have a chip on their shoulder, I take serious issue with this stance. In my own experience, during the most challenging times of my journey as a founder, this internal question was an obstacle, not an ally.

I see the same dynamic in many of the people I coach.

The setup goes something like this:

  1. My business is going through a hard time
  2. This feels like evidence of what I fear I have known for decades: that I am not enough
  3. Now, I am dealing emotionally with both my business challenges and this sizable fear about my value

When I ask the question above, ‘What if I cannot fail?’ I am less interested in exploring what if your business could not fail and more interested in asking, “What if you could not fail to be enough?” What if your value is cemented already?

How would you be able to show up as a leader if you already knew in your bones you were enough?

How would you show up in relationships if you had an immutable sense of your value?

How would you be free to show up in pitch meetings? Or other business-critical conversations?

When leaders come to me looking to improve the efficacy of their leadership skills, we often find ourselves backtracking to these childhood fears. We then begin to explore more direct paths to enough-ness. Time and again, I have watched the benefits of this work transform the client’s experience of life and leadership.

The same transformation is available to anyone willing to begin the journey. What might be available to you on the other side?

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Please feel free to reach out to me if I can be helpful to you in any way. Email me or DM me on Twitter. Thoughts on improving this newsletter are also always welcome!

With love from LA,


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Matt Munson

CEO coach @ Angel investor. Startup founder. Committed to helping leaders feel less alone in the journey.