Color Outside the Lines – Stretch Yourself

Live on the outer edge of your reach, not on the inner edge of your security.

Marshall Goldsmith, “Learn like a Leader”

To be alive is to allow feeling in.

This post is for the “engaged” mindset. (See past post). So, if you are in an engaged mindset, read on.

I’ll repeat. To be alive is to allow feeling in.

While having a warm, sunny Saturday morning chat with a dear friend, we began playing with the concept of feeling. We recounted that when we were children, we would be curious and playful with things, people and ideas. As we now reach 50, we’ve grown cautious and pensive, and therefore, we want to push ourselves back to the “edge of courage,” and recapture that same feeling of childhood playfulness, a time of great growth.

A challenge arises as we allow the feelings of playfulness to flow in. The same neural path of good feeling also allows old memories, and their related painful jabs, to enter. We contemplated that avoidance and fear are the reasons why, as we get older, many people emotionally disengage or remain neutral in their emotional growth, in some sense, purposefully stunting their growth to avoid pain.

Imagine if we could just suspend our perception of the painful feeling, we could get to the other side of our “edge of courage” and color outside the lines. We could play in a space that we avoided exploring before. To keep us safe (our perception of safe), we create a boogey man of pain that is outside the lines – a colleague yelling at us, we become invisible, we are wrong, we fail…but at this age, there is no failing, there is only a ticking clock of time, decrementing the minutes left to be curious…curious about what is on the other side of the “edge”.

So, we reflected on methods we could practice getting near the edge, and pushing ourselves back to and over the edge when doubt creeps in.


  • Remind yourself the gain is greater than the pain – ALWAYS.
  • Remind yourself the perception of pain is NOT REAL.


  • Keep creating visions of who we want to be “the next moment”
  • Generate a gratitude list – it will generate the positive mood for creativity/curiosity
  • List your past successes and failures. (advanced: assign root cause)
  • In the moment
  • Just do it
  • Breathe. Reflect on your possibility.

Practical tips

  • Practice a small version of the dream first, then, do it. Then, go for the whole enchilada.
  • Plan your action, and others’ reactions and prepare for objections or rejections
  • Tell a trusted friend. Have them join you or force you.
  • Be around masters of whatever you want to achieve (and are afraid of). Permit them to inspire and drive you.

A client of mine just recently had an awakening. The context was negotiating equity with his “to be” CEO. The negotiation had been deferred months and months due to the fear of the conversation; that made it none the better, nor none the easier. The counterpart was somewhat bold and feeling comfortable to ask for his value. My client prepared, planned for objections and reminded themselves of the business scenarios that could emerge. My client also prepared for all consequences regardless of the outcome of the negotiation. We also prepared that the conversation may not be “one and done,” and could end up being multi-staged. In the end, my client was out of their comfort zone, having been the first time he had tried to elevate to the Board role in his own company, and give up daily operating control.

Ultimately, because of good, honest dialogue (nonetheless hard to have the conversation), this was not the right person to hand over the reigns of the company to.

I appreciate the coloring outside the lines my client tried, to the extent of even being open to handing over day-to-day control of the business he created. An unintended consequence of the negotiations was my client fell in love with his business again, and as such, my client became more engaged in his own business and made improvements over the last year to improve its cash flow by 30 percent.

A little extra credit for those who read this far…

Please reflect on what happened when you took a risk recently. What was the risk? When you leaned to the edge? What were the consequences that you imagined? After you were successful in taking the risk, did you realize the consequences were over-estimated by you? What did you learn about taking risk for your future “coloring outside the lines?”

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