30 Days of Risk Taking



Artist: Ageta Oleksiask “Olek”, stretching out.

For those of you who want to move something forward, get “unstuck” or better yet start something you didn’t think possible for fear of failing.  I’ve got a challenge for you.  I’ve worked through my own questions around this area, which can include things that scare me or are holding me back, and as I coach my own clients, we know the best way to tackle anything is go out and start doing something in an area that matters to you.  It sounds simple but when you’ve been stuck or aren’t sure of what the start looks like, it can be harder than it looks and always best to ask some simple questions to frame things and then take the first steps. Questions such as, what matters most to me and what do I need more of or less of in my life?

In the past few weeks I was fortunate enough to listen to an amazing discussion with thought leader and humanistic marketer Seth Godin on fear of failure and what he suggested to do in order to move past it, including setting yourself up for lots of small failures.  This idea sparked my 30 Days of Risk Taking, which is the personal challenge I hope you’ll take part in now. Determining one risky thing every day and then taking action, small, big and in between whatever feels uncomfortable to you. We’re not talking about actually doing something risky, like jumping off a building, that would be bad, but the perceived feeling of being risky.  It can be as small as saying hello to a stranger or as big as saying you’re writing a book or standing on a super tall ladder.

My theory is that with every stretch out we’re able to build the muscles needed to take on the big thing we really have wanted to do, but were too afraid to tackle, whether it’s starting a new job or learning how to make jewelry.  What is it that we really were meant to do, but kept putting road blocks in the way?  So here’s where the rubber hits the road with myself as the guinea pig, and I have to tell you  that with the 30 days under my belt now, things felt at times exciting, nerve racking,  and most importantly created an anticipation of what’s going to happen next.

The reality is that finding that one thing a day is as much of a challenge as doing it, you have to be present, looking for opportunities and then willing to jump when they come up, the ultimate risk taker. If you get stuck one day don’t give up, take that day to figure out what you need to do next but keep it going no matter what.  If you want to see what one person’s journey looked like, mine is below.

A quick note that what feels risky for one person might be really easy for another, it doesn’t matter what it is but more importantly how it feels.  I know whatever happens I’ve learned a lot, met some nice people along the way, so what else could you ask for.  I hope you find this interesting, but more importantly inspiring enough to get you to join the challenge, like others have done already.

Let me know what you’ve done, how it felt and what you want to do now because of it.  In the end it’s all about doing the great work we set out to do.  Have a super adventurous day, whatever that looks like for you.


Stay Curious,




1. Saying Yes to a Podcast on a Topic I’m Passionate about but Not an Expert On.

I’m excited but nervous, should be interesting to see how I do, although I know a fair amount about fear of failure and risk taking since I’ve been wrapped in it personally and professionally for over 18 years, there is nothing like putting yourself out there for everyone to listen to what you think.

2. Told a Writer that I’m Writing a Book.

I’ve started a book and while I don’t consider myself a “writer” I knew it was time to put together my thoughts in order to help others looking for the same information. The real opportunity to came when a travel writer asked what I was doing, it was at the moment I told her which I felt both nauseous and committed and I realized saying it made me all in. I’m now thankful that I know a few writers who will be honest with me when it comes time to look at what I’ve got.

3. Stood on a Very Tall Ladder.

Here is where you might find that what’s scary for you isn’t necessarily scary for me.  I don’t like heights but on a recent volunteer day there weren’t any other jobs left, plus I knew what the outcome should look like, who better to get up there and make it right than me.  It made me sweat for sure but the final product was lovely and I didn’t fall off , so all was good.

4. Wore a Dolphin Hat to Welcome new Kindergarten Parent Breakfast.

While this isn’t the first time I’ve donned a dolphin hat, it was a bit nerve racking to wear something in front of strangers/ peers who met me for the first time are now going to base their understanding of me on a foam hat.  On the flip side it says I’m serious about school spirit and their children’s whole development, so I think it was a win all around.

5. Introduced myself to a Big Wig, Just Because.

I can be weird about cold introductions to strangers on the phone with no connection.  I’m great in person, I love finding out about people, thanks dad. Put me in front of a room full of strangers to speak/facilitate and I’m all good to build a bridge so we can make something bigger happen, but do a cold connect, yikes.  I followed my intuition the other day and sent a note, then did a phone call with the head of a company who I now am having some really interesting talks with on how we help more children stretch further.  Well worth the jump.

6. Sent a note to acknowledge  my lack of gratitude

This one was hard and it’s just the start.  I consider myself a generally strong self aware person, who believes being grateful for what I have is a key to living a good life.  There is one situation in which I didn’t do the follow up deserved for someone 2 years ago. The person went out of her way to help me in a big time of need and I didn’t reach out, again totally not my usual MO.  When I look back I think some of it was me being steeped in insecurity and wanting to stay hidden at the time.  Whatever held me back it’s haunted me not saying a proper thank you but as time went by it seemed weird/awkward to contact her, until this week.  I sent her a note yesterday explaining how I felt and hoping we could meet for coffee so we could catch up.  I’m not sure what will happen but for myself it was an important step in tying up loose ends that can weigh you down, no matter what the outcome is.

7. Put together a new educational offering on a dime.

The recent teacher’s strike in our area could be seen as a tragic situation or an opportunity.  I’ve chosen to look at it as an opening to try some new work ideas out I’ve been rolling around.  So with shorter than comfortable prep time I sent out a note to my closest circle to see who was ready to try out something new for their tweens.  Can hardly wait to see what happens, but a little nervous as well.

8. Dance to Pharell William’s “Happy” in front to the school.

With the school year coming to an end I hosted a walk to school day.  I noticed a few younger students grooving in the crowds and then some older ones clearly wanting to but not wanting to appear silly.  It was at this point that I realized I was going to have to help them with this and broke into full dance mode, despite the horrified look on my son’s face.  I’m not sure what was better his look or the that of laughter on every parents face.  Here’s to jumping right in.

9. Placed promotional materials on the cars of people in my middle circle.

Today I declared myself and my passion to a group of people I consider aquaintences.  That group of people who have seen you around but don’t really know who are what you do.  I figured it was a perfect opportunity to introduce them and their children into the area of youth coaching that I help with under 30′s by the good old fashioned method of leaving material on their car.  I have to say it was definitely outside my comfort zone as I like nice controlled environments that still show my professionalism.  Today I let it go for good old fashioned information exchange.  I feel like I bridged a mental gap.

10. Came armed with a totally different birthday present than the norm.

I decided that at a no birthday present party I would come armed with a non traditional present, and while everyone else still brought things like flowers, baskets and wine, I brought lemony potatoes, a fan favourite for many of my friends and a decided item that I love to make. I determined that it would be better to share a part of myself that is a strength and says something about me leaving something of myself I want them to share in, than doing something standard.  Rave reviews from the birthday girl and all those at the party.

11. Ate something different from a menu we love.

Ok, this might seem small and especially if you’re adventurous food lovers like ourselves, but taking an opportunity to shake up our menu picks even left the long time owner of our local Indian restaurant saying.  Way to try something new, clearly it was time.  Ooo how we love good south east asian cuisine, it makes you feel warm all over just thinking about it, and it opened the door for making me wonder what else we haven’t tried that we really need to.

12. Admitted a politcal bent at a party.

It’s not that I don’t have a strong point of view, most who know me know that I’m not afraid to share but I have an unwritten rule that parties shouldn’t be taken over with political views as sometimes it has a reverse party outcome.  This time I made an exception and while the conversations went fine, coming away and doing the analysis I’ve decided I’m going back to my original theory.  I would call this a smaller failure, that I learned from and will use to gauge, not stifle, my political views moving forward.  Lesson learned.

13. Started an Interesting Conversation.

While in to see my doctor.  I decided to stretch out on a topic around youth, normally I wouldn’t bring my business into my doctor but I thought if I really care about what I’m doing, I’m going to see if there is another way to connect the dots.  The conversation ended up giving me a whole new set of insights and possible ways to assist under 30 and possibly the overwhelm facing doctors on topics as well.  Win/Win.

14. Took on Facebook

So for many this is an every day thing.  Using Facebook to share parts of who they are and what they’re doing.  For me it wasn’t so much that I didn’t want to share as much as what  and technically how.  I built a big ugly wall around this that even a grandma would have thought impressive.  I signed up for a small class where I started by announcing my biase and that I was behind and then proceeded to ask lots of questions.  I feel much better now and am starting to stretch out to the world in a new way.  Feels just fine.

15. Made Technology my Friend.

This week technology is the key.  I faced yet another technological question around e transfers. Sending money in different ways feels like it’s going to help my relationship with money grow.  A good thing for sure.

16. Agreeing to Present to a Group on a new topic

Something strange happened today when I decided on a whim to say yes to a group who asked to have a presentation done on a topic I love but am not a specialist in.  I’m only slightly nervous.  Talk about weird.

17. Made friends With a Stranger at The Cafe

I saw this person sitting at the cafe and decided to start up a conversation.  It turned out that they knew other people I did in town, a totally small world.

18. Agreed to a Horror Movie

I hate horror movies but I finally agreed to sit with the family through one.  Ok we agreed to an oldie, Carrie, so I made it through most of it and yes then had some nightmares.

19.  Did my first HugDug

Did my first book review online which then gave back to charity.  I have to say it felt pretty good to promote something I love and do good.

20.  Tried something new

Went into the local veggie market and tried yellow tomatoes.  It turns out they aren’t half as good as the red ones, just my opinion but I’m glad we tried them

21. Did my first podcast, on risktaking

How funny was this.  Finally doing my first podcast on  Risk Taking and then finding out that the equipment failed.  Take 2.

25.  Learned how to take out a trailer toilet

Ok, so while youtube did show us how to fix it.  It didn’t tell us about all of the other problems we would create.

26. Yup day 2 of the great toilet caper

We now have chanelled our inner Macgyver and any other handyman we could think of ,then had to admit defeat and the need for a new toilet.  Learned lots in the process.

27. Was Honest With a Family Member

Got up the nerve to tell a family member something I’d been thinking with my inside voice.  I think it went fairly well, and I don’t feel like I’m carrying it around with me anymore.

28. Tried to Kickstart a Teen Volunteer Group

Had this great idea for a teen volunteer group.  It didn’t quite work out the way I’d imagined but I’m going to try again.

29. Cooked a Meal I’d Never Tried For Company

I don’t usually take risks with dinner on out of town guests but did it this time.  I have to say it was  quite good and started to get over the fear of being perfect, so that’s good.

30. Giving a speech on 50 Years of Marriage

How do you sum up 50 years of marriage in minutes in front of the people you love most.  As it turns out it’s a lot easier than it looks.



  1. Hey there! Do you use Twitter? I’d like to follow you if that would be okay.
    I’m undoubtedly enjoying your blog and look forward to new posts.

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