MMP: To Win At Life You Have to Risk Loss

by Rebecca A. Watson on July 21, 2014

in change, comfort, Monday Morning Pages

I remember years ago, maybe in junior high, learning the definition of an entrepreneur. There was the traditional definition — one that starts his/her own business — but my teacher would always insist the real definition was this: A Risk Taker.

I never considered myself one of these risk takers. My dad owned his own business and he worked hard, long hours. He worried about money and stressed about jobs. It seemed he never took a day off.

But somehow I found myself gravitating toward that role several summers ago. Actually it was around this time in 2011 that I started my own marketing business.

And gradually it has dawned on me that I am exactly that. I am a risk taker. And this time of year happens to be my habitual risk-taking time.

mark calendar

Yep, it’s about time for another adventure.

In 2009, I moved to California without a job or contacts. In 2011, I gave up a ridiculously well-paying (albeit soul-sucking) gig to work part-time and start my own marketing biz. And in 2012 I wrote this:

“I guess things are really coming to a place where I realize that I need to take some risks. I’ve definitely spent some time being comfortable.

Now it’s a matter of pushing a bit more — not looking at junior level contract jobs. I deserve a higher level of pay and respect. I dunno. I feel like right now is such a weird time. I’m getting to a settled point and I want to push for something new.”

It was around that time that I signed a new client and ended my part-time gig, working full-time on my business.

And then came 2013, writing in a hotel room in Connecticut, halfway to Germany:

“Failure is a part of success. The only real failure is not to try. Isn’t that the truth? I so often wouldn’t write something because I’m afraid it’s not good and will make me feel bad. But really, it’s the people that take risks who live life. I mean that’s what we’re doing now, taking a risk.”

sante n rebecca germany

A calculated risk, being that I married an engineer. But a risk, nonetheless.

And this week I’m taking another risk, pursuing a dream I’ve been wanting to try for more than a year now. I’m finally becoming a life coach!

And I’ve tied it in to my life’s mission, which is to help people through my writing. If you’re interested, you can read more about it here.

Taking risks is what evolving on this planet is all about. If we really want to win life, we’ve got to get used to being outside our comfort zone some of the time.

And it’s also how we learn. Because even if we’ve failed, it’s not a mistake if we’ve learned from it. And failure can teach us (and others, if we’re open to public failure) more sometimes than success can.

Not that I want to fail, of course. This endeavor really fulfills part of my life’s purpose, I believe. After being a sober pen pal for many months, I think I’m going to like this line of work. I’ve been told by many job aptitude tests that I’d be a great therapist. So we’ll see how it goes.

Risk isn’t always quitting your job, or starting a new project or moving across the globe. There is risk in everyday changes as well. I took a risk when I quit drinking. Heck, you can take a risk by wearing a skirt instead of shorts.  It’s more about getting outside your comfort zone.

What are you doing in your life to take risks? Are you getting too comfortable or do you challenge yourself in different ways?

Wondering what this Monday Morning Pages thing is all about? Read how it started. Or check out all the archives. Also, special thanks to Jean-Claude Killy for the title. Alpine skiers really do have a way with words — at least the ones I know.

{ 4 comments… read them below or add one }

Maryn July 21, 2014 at 10:54 pm

You go girl! I very much agree with this. Life is constantly changing, I think it’s just a natural part of living, but we so often resist it in order to stay “comfortable.” My friend and I are embarking on a new project We’ll be traveling to LA/SF this month to start filming a documentary on redefining the American Dream. I’m feeling quite raw – nervous and excited – which I think are good signs!


Rebecca A. Watson July 22, 2014 at 8:33 am

Oh this is so cool Maryn! I’m super excited for you 🙂 I have some friends in the SF area, so let me know if you’re looking for anything/need help. i will ask around. And you’re right, that raw feeling mixed with nervousness and excitement? That is a good sign 😉 Woooohoooo!


Gabby July 24, 2014 at 2:43 am

I admire all of this so much! I hope it feels as good as I imagine it does to be in business for yourself and be rewarded by all of those taken risks. Also, can’t wait to hear more about your life coach pursuits. You are pretty much living out all of the plans I’ve never said out loud. Love reading such great updates 🙂


Rebecca A. Watson July 24, 2014 at 1:18 pm

Thank you so much for your kind words Gabby 🙂 You are so sweet! And it does feel pretty good actually. Raw and real and open, but very good 🙂


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