1001 Leadership Challenges

“Life is either a daring adventure, or nothing at all.” – Helen Keller

I recently had a conversation with someone about how the world is changing so much; and how, in the place I live – Vancouver, BC – the real estate prices are such that a family with double the average household income can no longer afford a single, family home – even in the suburbs.

My friend’s comment was that if they knew then, what they knew now, they may not have chosen to have kids because they’re concerned about how much those kids will struggle.

Opposite Thinking

As I heard the comment, I was thinking almost the opposite: that this is a great time to be alive, and there are many great opportunities – if you are up for the challenge, willing to do the work, and to stretch your capabilities. Although things may be more expensive and more challenging – as in many cities around the world – the point is that you are either in one camp, or the other. I’m in the ‘it forces you to get stronger’ camp, and he’s in the ‘it slowly destroys you’ camp.

A lot of this links back to Keep Going for It (Chapter 16) in my book Your Oxygen Mask First. If you keep learning, growing and stretching, the next leadership challenges that comes along are no big deal.

By default, I’m wired to think that almost anything is totally doable – and that challenges are kind of fun. You can come across an obstacle and learn through it.

I’ve been exploring getting my pilot’s and helicopter pilot’s license – both incredibly hard to do. While I’m not sure I can find the time, I’m intrigued with the challenge – and I know I can do either, if I set my mind to it.

The hard truth about leadership? It either forces you to get stronger, or slowly destroys you.”

On reflection, that quote is a great summary of everything I’ve learned about leadership over the past twenty plus years. Leadership – whether in business or the attempt to be great at anything – is an incredible catalyst for your own growth and development as a person. I’ve seen that, no matter what the challenge, if you commit to learn and grow through it, you can do anything. I probably have thousands of examples of people who have done so.

Because the truth is, if you want to be one of the snake charmers in India who catches and works with cobras, you need to be darn good – or you’re dead. The same thing holds true of a leader in a growing organization.

(BTW, I was thrilled to hear that well-known supermodel/author/entrepreneur Kathy Ireland shared that quote from my book on Twitter, a few weeks ago.)

Old Habits Die Hard

If you’re still going with old skill sets, chances are you also have outdated ways of thinking.  It just isn’t the same as when our parents grew up, when they were buying a house. But if you continue to come from that place, to use that as a comparison for success, you’ll continue to be limited.

For those who embrace leadership challenges, who continually learn and improve skills sets and operating systems, it is a wonderful rewarding journey that forces you to learn and grow – and to thrive.

The biggest gift of all is that you get increasingly confident and capable.

Once you have conquered 1000 notable, different challenges, 1001 is nothing.


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Straight-talking, passionate and energetic, Kevin is known for his invigorating presentations, packed with practical knowledge for leadership and life – and a lot of laughs.

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