Make the Awkward Ask

In a world overrun by email, there are still a few I actually enjoy reading. One of those is the Creative Groove Newsletter written by the amazing Jen Jones Donatelli. If you have no idea what I’m talking about, or who Jen is I encourage you to look her up, and then to sign up for the newsletters; they are short, punchy, and chalk full of fascinating content from roller skating options, to a grow a forest accountability app, to invitations to learn about cool events in the city such as The Full Cleveland (a 12 hour megahike across town).

One of her more recent newsletters began with the headline: “If you’re looking for five powerful words that can take you to the next level, here they are: ‘Ask, and you shall receive.’” In that letter, Jen relays her own story of pitching herself to an editor at Enslow Publishing back in 2006. She recalls what a “long shot” the ask was, and how she waited for a polite pass to her inquiry for a gig (if any response at all). She didn’t have to wait long for a response, but instead of the anticipated “thanks, but no thanks,” she was offered the job and went on to do really incredible work. She recalls, “…I can say with 100% certainty that none of it would have happened if I hadn’t summoned the courage to send that initial email.”

Speaking of courage…

Enter Scott Simon, founder of Scare Your Soul. Scare Your Soul is a movement that “inspires people to engage in repeated small acts of courage that lead to big changes.” I recommend signing up for his newsletter too! In it, you will receive weekly challenges to get you out of your comfort zone, and more fully into your life 😉 Each month has its own theme around which the challenges are centered. For instance, June’s theme was self-love while July is all about relationships.

I am lucky enough to know both of these cool cats which led me to synthesize Jen’s letter with Scott’s mission to come up with my own idea/challenge for all of you who follow.

Here it goes:
I want you to think of 10 ‘asks’ you have yet to make, but really want to – maybe that looks like asking someone on a date, maybe it looks like asking someone for a job, maybe it looks like asking someone to teach you a new skill, or maybe it looks like asking someone you want to learn from out for a cup of coffee.

My asks are all centered around people I one day hope to work/collaborate with (at this point on what and when are TBD).  I am so confident in their abilities, and their missions, and their characters that I’m okay with not knowing what these projects look like yet – just that I want to be a part of what they are birthing into the world. The list of those people are below and while it is scary to ask people you idolize to work with you, amazing things can happen if you do (see my note next to number 10).

As a nod to something I learned from Randy Pauch in his “last lecture,”  I’m hoping that by posting my asks publicly I’ll make it harder for people to say ‘no’ (wink wink). Click here to see Pauch’s speech.

1. Lisa Sands  – I am super interested and intrigued with the salary project you mentioned in the March Radness group. I would love to be a part of this in any way that I can! Sooo inspiring!
2. Caryl Church – You are everything I am not. Calm. Centered. Confident in the deep wisdom you  have to offer the world. Every time we speak I am blown away at what a great teacher you are. I consider you a mentor, and who I want to ‘grow up’ to become.
3. Rebecca Wohlever – Sing to me. Seriously. I am still haunted by your “Haiku for You” song. I feel super cool knowing you and would feel even cooler to get the chance to collaborate with you on something.
4. Jen Donatelli – I don’t think I can tell you any more how much I admire you and your work. You offer more in 20 minute trainings then most people do in entire weekends. I have learned so much from just watching you, and paying attention. One day I would love the opportunity to spend more one on one time studying with you.  You are like my ‘celebrity’ name drop lol.
5. Masha Weenink – My grown up pen-pal. Masha and I met through Insta and have developed a friendship over the course of the past year. We were initially drawn to one another’s art, and words, and stories. We have a bigger project in the works that ends with a “real world” inter-continental ending.
6. Samar Shata – You know how sometimes you just meet someone and you are instantly intrigued. Instantly smitten. That is Samar for me. She is fierce! Super smart! Super articulate! And super ready to dive into depths. My kind of person! We met at a Women Who Run with the  Wolves summit in Colorado a few years back and I have a feeling we may yet meet again.
7. Masha Shukovich – Another ‘she-pack’ member from the Wolf Summit. Basically everything that drops from this woman’s head onto paper is magic. I hope to become the writer she has already proven herself to be. I don’t think I have every explicitly expressed to her how much I would love to collaborate on something in the future – so here is me doing that now. I actually got nervous writing that because the really insecure part of me is saying, “Why would a woman of her skill and caliber work with someone like you.” And just as an aside here: Masha’s spirit is warm, and gracious, and good indicating that it’s my own negative self-talk getting in my own way, as opposed to a statement about Masha’s unapproachability.
8. Bevin – “Decide and declare.” “Every yes carries with it an implied no.” “Do the damn thing.” These are just a few of my favorite Bevinisms. I have basically been strutting around town quoting her since I attended one of her entrepreneurial classes in early Spring.  I am quite sure that I will be signing on for some more Bevin time in the foreseeable future. She gives teeth to dreaming so that one can actually see what happens in their head materialize into the 3D world.
9. Chris Bordoni – Can we get back to talking about our workshop!? Ask this guy about his ‘unpublished’ resume when you get a sec! It will have you over-sharing your own failures and smiling in the process! Feeling like you ‘suck’ has never felt so good! It takes a pretty magnetic person to have you happily anticipating your next ‘screw-up.’ 
10. Scott –  I already introduced you to Scott above. I summoned up my courage to ask him to join me in a project I was too nervous to tackle on my own and guess what – he said yes, and he did so without hesitation. You can catch us at Arabica in downtown Willoughby from 9-11 am on  Saturday, June 26 for a special something somethin.

And in case circling back to the other people on my list won’t keep me busy enough, I thought I’d take it one step further and throw out the names of some serious long shots below – because you never know who knows someone who knows someone who….

Famous People I want to work with: Lena Dunham, Liz Gilbert, Glennon Doyle, Thrity Umriger, Austin Klein, Taylor Swift…it goes on and on but those are some off the top of my head.

I would love if you are reading this if you would just post one ‘ask’ in the comments below. After all, you never know someone who…