Challenge Yourself: Keep a Dare Journal

Triple Dog Dare from A Christmas StoryI’m fascinated by risk. I’ve taken my fair share of big-time risks in my life: started two business ventures, moved from Washington DC to Austin TX without a job, got married when I was only 21 (to a wonderful, beautiful woman who I know I’ll spend the rest of my days with). And I take countless smaller risks every day (driving on Texas roads isn’t exactly an act for the faint of heart). Yet, I still find myself not tackling some tasks I know will move me further toward my professional goals…because there are risks involved.

Sound familiar?

Here’s my strategy for conquering this challenge head-on: keep a Dare Journal. Every day, I start my Dare Journal with this statement: “Chris, today I dare you to…” Some days, the dares are relatively small. For example, the dare might be to contact one individual in my network for lunch. Other days, the dares may push me toward bigger challenges outside of my comfort zone. I already know that one huge dare is to write this book by the end of 2012. If you’re not sure what the dare should be, ask someone else to pose it (extra points if they “triple dog dare” you).

The key is to just start. If you’re already feeling anxious about it, don’t be afraid to start small. The important thing is to realize that living without risk isn’t really going to get you where you want to go.

Now I dare you to keep your Dare Journal going for the rest of the year.

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About Chris Bailey

Since I was a kid, I've have been fascinated by the concept of work and how we choose our distinct career paths. My own career path has included work in nonprofit membership, customer service, career coaching, entrepreneurship, and marketing. I'm currently working on writing a book called The Alchemy of Soulful Work. Learn more.
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Sonya76 23 pts

I'm quite a risk taker - got together with my husband at 19, started my own business and moved abroad at 23. But I've always wanted to write and I've never had the courage. Perhaps a dare diary is the thing to get me started.

My latest conversation: Ski Chamonix