Risk-Taking and Decision-Making

(That’s me and Sean.  I posted this picture for two reasons: one – he’s a part of this post; two - it’s a long post with lots of storytelling, so I thought “with pictures!” might be fun.  This picture was taken at our friends Steph and Allan’s rehearsal dinner the night before their beautiful wedding back in September.)

Ok, so.

The travel bug bit back.  As this posts, I’ll be in Chicago at the Hands On Small Business Workshop on Thursday morning, and then at the 20sb Blogger Hang (open to everyone, not just 20′s and not just bloggers!) organized by @ChicagoTweetups (thanks, Brandon!) on Thursday night.

If you’re in Chicago tomorrow, come find me!

Friday – Sunday, I’ll be debaucherizing the Denver area with Chelsea and Matt at champagne bars and comedy shows.  I’m CAPS LOCK EXCITED to see Matt again, to finally meet and play Champagne Bar Socialites with Chelsea (we have sparkly dresses!), and meet and pick the brains of one of my mindcrushes Sharalyn Hartwell.

While I’m gone, I’ve got these things in store for you:

• Today’s post shares some really great insight from my friends and blog heroes on risks taken and big decisions made.
• Tomorrow’s post shares some Really Exciting News about risks I’m taking and decisions I’ve made.  Seriously, you won’t want to miss that one.  I strongly considered waiting until Monday to post this since this week looks like I’m trying to NaBlahBlahBlahPo and I’m not, butI just have a lot to say this week, ok?
• On Saturday, I’ll point you in the direction of a project that Sharalyn put together for her Gen Y Examiner column.  She grabbed a bunch of bloggers (including me!) to talk about gratitude and giving thanks, and my two cents worth goes up on Saturday.

For today, I asked a few people (ok, 12 people) to answer this question:

What’s the biggest risk you’ve ever taken or craziest decision you’ve ever made?  How did it work out?

Here are their stories.

M left a path she felt was more chosen for her than by her and hasn’t looked back:

What I consider to be the biggest risk I’ve ever taken was composed of a number of decisions, all made in a relatively short period of time for pretty much the same reason. When I was at the end of my junior year of college, I looked around at my life: my boyfriend, my career path and the way I made decisions, and had an absolute meltdown.

I hated it. All of it. I realized that I had been making decisions for over 20 years based on what I thought everyone else wanted from me, and it turned out that I didn’t actually want any of it for myself. So I broke up with the boyfriend, changed my major and looked my parents in the eye and said “I’m done.” And it was scary and everyone around me freaked out. But ultimately? It was the greatest thing I have ever done for myself, to step off the path of the known and venture out into the unknown.

Sean Brown, long time close friend, inspiration, and adventure-seeker, was causing trouble even 14 years ago (and probably before that).  Right now, he’s writing about The American Dream from his post out in Portland.  Fourteen years ago, he risked detention to be a hero – and won:

With a seething rage and blind fury, I was escorted from the 8th grade extra credit end of term science lab.  Unfairly, I might add.  Thoughts of stabbings and arsons danced through my young mop top, when I saw It.  It being Mrs. Williams’ grade book.  Just sitting there, unguarded, in all its green canvas glory.  With the quickness of a rabid mongoose on speed, I snatched, I grabbed, and I ran.  I Got Away.  I dropped the bitch in the storm sewer on my walk home from school.  Mind you, this was in the days before there were computer grades; I had effectively erased a marking period’s worth of grades from existence.  For every student in six sections of 8th grade science at Jefferson Junior High School.

Being 13, I told all of my friends, who told all of their friends.  I was a hero for about three weeks.  I was a Legend.  And then came The Boom.  A week’s suspension from school, a semester’s grounding from my parents, a third of the season’s suspension from the 8th grade Jefferson Huskies baseball team.  And yet there were still No Grades.  What I did, could not be undone.  Looking back on it fourteen years later, I would absolutely do it again.

Jenn – makes me jealous with stories of overseas travel:

The biggest risk I’ve ever taken was definitely studying abroad in Madrid. I was living in a foreign country that I had never been to, surrounded by a language that I barely spoke. I was forced to adapt to the culture, the customs, and the world around me. The food was different, the transportation was different, and the television was different. On top of the fact that I was thrown into a whole new world, I was doing it by myself.

I chose to go on a study abroad program through a different school, and I was the only one from my university to go. I didn’t know a single person in a group of 90, and they all knew each other. It was hard to go from a place where people knew me, they got me, knew I was quirky and spunky and weird and loud. I felt misunderstood for the first couple days which, for the record, feels like an eternity when you’re traveling on a bus through Europe. It was a challenge to find my place among new people in a new place, but I did it. I had the time of my life, exploring a new city and reflecting on myself and my life. It was an amazing opportunity, and I wouldn’t have done it any other way.

I think Art is the first Twitter friend I met offline.  I think.  Anyway, here are some of his risks and how they worked out:

In life, I opt for the risk over the safe path. This has not always worked out, but I do not have one regret. The following are the biggest risks I’ve taken and their subsequent results:

Transferring High Schools. In 11th grade I transferred to an arts high school to study writing. I left all of my friends and the guarantee of sports, a world-class education, and general comfort of situation to do what I love. Result: WIN.

Engagement. When I was 19 I proposed to my 17 year old girlfriend of a year and a half. Long story short: Result: FAIL.

Adopting a cat. WIN. WIN WIN WIN.

Moving to Boston. After a year at Iowa State, I transferred to Northeastern University in Boston. I had wanted to go to school on the east coast for years, but the most immediate driving factor was the girl. We ended up breaking up within 6 months, but I spent three years out there having countless life experiences. Result: WIN.

Bearing my darkest secret to my entire church. While I won’t share it with you here, let it suffice that I shared my darkest time with my entire congregation one Sunday in support of raising funds for the Asturias Academy in Guatemala. It was one of the hardest things I’ve ever had to do and I wasn’t even sure it was the right idea or if it would have the desired impact. It did. Result: WIN.

I also like to try new food and drink (almost always a WIN), new places (WIN), and new people (WIN). Win win win.

Real life friend, personal recipe vault, and all-around mentor, Kate shares her love story, which I could happily hear over and over and over.  (She also writes a wonderful food blog – Kate in the Kitchen):

I was so not a risk-taker. I had a 7 year old son, I was a single mom and I had no social life. Just the idea of using an online dating service was risky to me. Our life, for my son’s sake was routine and regular. It was great for him but not so exciting for me. I just wanted to sit across from a guy with a need to shave and have something to talk about other than Pokemon and Nintendo64. I wanted to drink something other than juice and I wanted to eat seafood. I wanted someone else to drive me around. I wanted to take a walk without always keeping my eye out for a little person darting around. But online dating?

Mostly reserved for losers and those who can’t get a date, I jumped in just because I was looking for someone to hang out with and break up the monotony of being a single parent. And dating as a single parent? Talk about risky. You don’t want to bring someone into your life, your life with a small and vulnerable child unless you really know what you’re doing. The potential for being hurt becomes two-fold then. It isn’t just your heart that’s on the line.

There were two nice things about Match dot com; one was that you could browse without paying a fee, and second was their Venus Matches. Based on how you filled out your profile, the Venus Matches were a list of names that were deemed compatible with you, and gave you a percentage of their perceived compatibility. No matter how many times I logged on to the site, at the top of my Venus Matches, with a whopping 97% was a very good looking guy. I bit, finally, and took another risk, investing the fee to Match to be able to contact him and see if he was really worth that 97%.

This past August, we celebrated our 7th wedding anniversary. I’d say he was well worth the chance I took, for both me and for my son who got an amazing Dad out of the whole deal. For all of us, it was the best $25 I ever spent.

Another favorite local foodie, Crystal Grobe‘s taking a career risk. For people like us, I’m betting on it working out for her!

The biggest risk I am taking is not returning to my recruiting/human resources career after being laid off.  I’m going against my own advice to candidates and instead of going back to what I have known for the last eight years, I’m venturing into something new.

Am I crazy?  Sometimes I say yes.  Other times I am convinced that I should be following my passion.  Isn’t that what people always say?  “Do what you love and the money will follow.”  Let’s hope so.

I knew Kyla Roma was a good friend, and the proof is in the risks she takes for them:

One of the biggest risks I’ve taken was reconnecting with an old friend. We’d had a big falling out over something trivial a year before, there was screaming into phones and terrible things said that only people who are very much alike could say to each other. She was now engaged to a wonderful guy until very suddenly it all unraveled. She started posting messages on facebook about how he had moved out, how he had been lying about having a job & she was broke from supporting him. She was terrified and alone, and no one seemed to be there for her.

After a lot of thinking I sent her a quick facebook message & said something to the effect of “I know we have a lot of history, but I know your heart and how much this must be hurting you. If you don’t have anyone to talk to I can literally be at your apartment in 10 minutes” and she asked me to come over. I showed up at her house, apologized for our falling out and we talked for hours. I started seeing her every few days just to make sure someone was there for her, we would have tea, talk, watch movies & I hugged her a lot. It makes me teary thinking about it now, because she was always shaking, from crying and from the hurt. Her plates & teacups would jangle the whole time we talked. I’ve never seen someone more fragile.

That was two years ago and we’ve never been out of touch for more than a few days since. Her whole life is changed now, it’s a beautiful & safe place for her, and I can’t express how grateful I am for that. Without question she’s my best friend, and the experience ingrained in me that reaching out to people is always worthwhile, even if most of the time people don’t need you, because once and a while someone will need you more than you can understand.

Nora‘s risk ended up giving her a great growth experience with an unlikely roommate:

Looking back at all the decisions I’ve made in the last few years, I’d have to say the craziest and potentially riskiest decision I made was to ask a guy who I hardly knew (but admittedly found very attractive) to live with me. Little old me who’d only lived with people shereally knew, asking a strange man to live with her in a part of town she didn’t know at all. Me, the girl who plays everything cautiously and gets anxious over anything uncertain.  We’d met all of two times before I told him I was interested in having a roommate and then asked him if he was interested (in living with me, nothing else).  He said yes. And what embarked was a two-year learning experience on how to live with a boy you aren’t dating. I did have a momentary panic  attack when I realized I was inviting a complete stranger to share my living quarters. I didn’t know his habits, his family, his past, his likes or dislikes, which were all things I knew about my previous roommates. My friends were shocked that I randomly decided to live with a dude but in my defense, I’d had girl roommates and some of them were downright crazy and I knew them so living with a guy I didn’t know? Had the same chances of working as the situations where I knew everything about them.

The end-result of my brash decision (I literally met him and he moved in within a two week time period)? Amazing. Seriously. We didn’t move in and fall in love as I quickly realized he wasn’t the kind of guy I’d want to date but instead, the kind of guy I wanted to be my best friend. We had a great symbiotic relationship: I cooked/cleaned. He took out the trash, hung things, walked the dog. He’d introduce me to guys. I’d provide dating advice. I learned how to live with a man who wasn’t my brother or father. I learned how to have more patience. I learned how to talk to a guy about things that were bothering me without getting emotional. It was a period of growth and if I could do it again, I would.

beccawik took a career risk, and even if she didn’t think it was such at the time – it takes balls to leave comfortable for new!

I think I’d have to say that the biggest risk I’ve taken in my life so far … is not having taken any risks yet. (Not sure if this is something that will make a good addition to your post, so feel free to not use). I’m not a risk-taker. I’ve never even really thought about how much of a risk-taker I am not. And although it is contradictory and a complete oxymoron, the biggest risk I’ve taken is not yet having felt the thrill of taking a risk. The only kind of fear that could be considered enjoyable (in my mind, that is).

Truthfully, I don’t mind not being a risk-taker. I know what I like and I know what I don’t like and I try to stay away from stuff in that second category as much as possible. But the in between. The stuff I haven’t tried yet. Even as I think about it, it sort of terrifies me. How big of a risk does it have to be to be considered a risk? Like, skydiving? Do I have to RISK MY LIFE to feel like I’ve taken a real risk? I left a GREAT-paying job for the internship that led to my current career. I never thought of that as a risk though–the bigger (and really, really stupid) risk would have been to stay at a job that wasn’t aligned with my career goals. I’m calculated.

I know what I like and I know what I don’t like. The stuff I don’t know which category it belongs in … I guess I’d better start dipping into that in between.

L. Jonkathryn, professionally-trained-dancer-turned-aspiring-(beautiful!)-writer says:

The craziest decision I ever made was to sell my townhouse (at the peak of the housing market in Arizona) and use the money to support myself while training full time to become a professional dancer.  I trained in modern, ballet, jazz and choreography 6 hours a day, 5 days a week, and performed with a dance company.  After about 6 months, I applied to a university dance program and was accepted on scholarship.

Ultimately, dance was not the career path I chose, but pursuing it was one of the better decisions I’ve ever made.  It enabled me to open my mind, explore new avenues of creativity, and much of what I learned on the dance floor has informed my skills as a writer. Now, fours years later, I’m taking a similar risk in training to become a writer.  I’ll let you know how it works out.

Amy took a risk in a relationship; if you want the full story – she captured that here:

The biggest risk I’ve ever taken was ending my marriage.  I got married at 21 and while I thought it was a good idea, the marriage was awful, and I spiraled into depression.  I risked forever hurting my relationship with my family, disappointing those around me and leaving a relationship that was comfortable and familiar so that I could pursue the happiness and joy that I truly believed was waiting for me around the corner—the life I knew in my heart I was supposed to have.  It was ugly at first—there were tears, hurt, disappointment and sadness on all parts, though both my ex and I knew it was the right decision.

I am happy to say that it was the BEST decision I ever made.  Yes, there were moments where I wondered why I’d made such a tough choice, and what I was doing.  But it was beautiful.  I grew into myself, I spread my wings and I became more “me” than I’d ever been.  I took a break from the traditional life I’d always had, and pursued art and went to massage school and spent a lot of time alone, getting to know me.  And while I ended up the English teacher I always thought I’d be, and I’m in a long-term, committed relationship once again, I’m so grateful I took a risk that I knew was scary, but right for me.

Christina Oppold, brains and beauty behind the StackedBlog, waxes a little more metaphysical, but I really dig it (and her!):

I worry sometimes that my life is just too boring, especially as I try to think of the riskiest thing I’ve ever done. But it’s never crossed my mind that what I’ve done was risky or that I was brave for making a decision until someone else has commented upon it.  It seems to me that the concept of “risky” is a subjective judgement call and the things I do in my life are part of the adventure I get to live.  After the initial ”What the hell am I doing?” passes through my brain, I find myself just enjoying the ride not worrying about those nagging “what ifs” that build up with fear.  It’s that fear that makes us consider what we propose to do as risky but once you commit, the fear fades.

Maybe the decisions I’ve made will work out, maybe not.  I’d rather go through the short time I have on earth not being afraid to do something because of the outcome; rather, I want to go at it with no constraints. That’s not to say I don’t have fears though. Those fearful moments are opportunities to grow and become a better, stronger person. Unless risky is the equivalent of “life-threateningly dangerous” to you, there’s really no bad outcome of our actions. What’s the worse that can happen? At most you finish the day with a lesson learned. At best you have an incredible experience that has enriched your life.

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I’m ending with this one because it’s exactly what I needed to hear/read right about now.  Tomorrow, I’ll share MY big news!

In the meantime, why don’t YOU tell me what your biggest risk or craziest decision ever was?  Share your stories in the comments, I’d love to come back to them!

Tagged as: adventure, Guest Posts, risks, Travel