What a Ride! Taking Optimism for a Spin

Farley 9.8 Carbon Fiber Fat Bike. Aka “The Beast”

A while back, I wrote a post called “I Suck At Optimism.” I’m getting a little better. So I guess now the title would be “I’m So-So At Optimism.”

Going back to the concept that optimism is a skill that can be learned, I’ve gone from a solid F grade to probably a B. And that is ok. I have picked up new skills and habits that help keep me optimistic. Mainly, I bought myself a fat tire bike to help me experience flow and joy – two key emotions that can feed optimism. Spotify playlists also help.

In 2021, I have had two main opportunities to my our optimism skills:

  • First, submitting a workshop to Agile Best Self to Agile2021. Only about 1 in 11 or 12 sessions get accepted, so that was a stretch. Luckily, I had help from several people (thank you Oluf and Lisa) who helped us edit, refine and get out of our own echo chamber. Our workshop was accepted! Fast forward to our Agile Best Self workshop on July 19, and we had 180+ people participate in our Intention Canvas Workshop. That was amazing and energizing!
  • Second, after being single since the start of 2020, I decided to start dating again. As someone who has been in relationships for the last three decades this was a big move. My last relationship was 20 years long, and I was in committed relationships prior to that. My 20 year relationship taught me many useful things, but did not prepare me for online dating. I don’t want to use the Agile Best Self platform to share and document all of the hilarious and flat out odd experiences in my dating life, but there are some great opportunities in the situation to focus on optimism, and own how I choose to show up.

And, if ever there is a need for optimism, online dating is the place! To prep for this leap, I read “Daring Greatly” by Dr. Brené Brown. I also decided to track some general stats in order to share my story with others. This is what I learned: Online dating is not about the protagonist (aka: me), it is a rather transactional wasteland. I’m willing to treat this like a second job and just move through a series of distasteful tasks to find someone special.

And people play by different rules-it is hard to be optimistic in a situation filled with so many expectations that are out of alignment. I’ve heard from men I’ve talked to that this is lack of alignment is equal opportunity issue – not just limited to my experience of a woman looking for a man. I learned quickly that some people in this wasteland are looking for emotional validation, but are still in marriages. Pass. Others are looking for physical hookups. Nice abs, dude. Pass. Some think they are ready for a relationship, but aren’t. Wrong timing. Pass. Many fudge their profiles. Whether it is age, interests, severely outdated photos, marital status or anything else I have seen some pretty glaring examples. Even if the profiles are accurate, if I meet someone in real life (IRL), the person has always differed significantly from the profile. And I bet I seem different in person than on the screen also. I have met a couple of men who are much funnier in person, much kinder and much more interesting than the profiles. And I just got called out (in a funny way) for underselling myself on my own profile.

Even once a profile is set up, there are key moments that almost every online dater experiences. Great moments to dig into practicing both optimism and grit. Getting over that initial step and setting up an online profile. The first “like” or “text” or “message” to someone you find interesting. The first response (and the first lack of response to what I thought was a well crafted thoughtful inquiry). Then comes the first in person date. Aka “The job interview”. My first couple of dates flat-out freaked me out. Again, I’ve been in committed relationships for the last three decades. I’ve had to rebuild my flirting skills and get over the weirdness of having coffee with someone I don’t know. I met some nice and interesting people, but there was no chemistry. In a way, it is even harder to be online when you realize that there are so many accomplished, genuine people out there looking for a partner. And that it won’t work with any of them because of a lack of chemistry.

Then came the unexpected “ghostings”. When using an online app, it is easy to cut off communication. I had at least two perfectly nice men ask me out and then cut off the connection prior to arranging the final details. Luckily, I’ve been working on Agile Best Self principles and concepts for a while, so I realized quickly this was a good thing. If it wasn’t a Hell Yes for them, it should be a Hell No for me. Being ghosted is the clearest Hell No a dater can get. Yes, it is a bit abrupt, but in the long run, it frees up my time to find the person I want to spend time with. Who wants to be in a romantic relationship with someone who decides to click on a button instead of having the communication skills say: “I enjoyed meeting you, but I’m not feeling the chemistry.”? Hell No.

I have not found that special someone yet (and this is not a call for my like-hearted community to set me up with their friends), but I have learned from each interaction. For example, if the tone is off and creepy in the first interaction, someone does not deserve a second chance. Second, there many great people out there. I have learned so much about other professions, hobbies and lives. Third, I am more resilient than I think. Most interactions are not about me, the interactions are about where the other person is in his life. Fourth, the better I get at this process, the better I am at figuring out what I need and want. It is easier for me to identify my own “Hell Yes” moments that help determine if the process should move forward from texting, to a phone call to first date to second date. I’m optimistic it will happen.

I believe that hard work and persistence will bring results. I believe that I can find what I want. And I still believe in optimism:


1.hopefulness and confidence about the future or the successful outcome of something.”the talks had been amicable and there were grounds for optimism”

So I still spend my mornings having dance parties with dogs; riding my fat tire bike; not getting upset when I get dumped; focusing on optimism and believing that persistence, consistency and taking care of myself will lead to the outcome I’m looking for: Finding a partner who believes in being his best self to enable me to be my best self.

Where do you want to hone your 2021 intention? Work? School? Parenting? Family interactions? I’d love to hear more.

Published by MichaeleBestSelf

Connector, Catalyst.

2 thoughts on “What a Ride! Taking Optimism for a Spin

  1. It’s pretty courageous of you to put yourself out in the saying world. I did that this summer. Some hits, some misses and conversations. Trying to be creative and get attention of someone was awfully difficult, and I also live in a rural town which added to frustration. Luckily, I did end up matching with someone locally (next town over, and her kid goes to school here in my town). We can be ourselves, continue our own independent growth, have some conversations about harder subjects and still maintain out best selves.

    Between that and opportunities at work to lean in to, and some volunteer/ community things, I have a lot to think about and have impact.

    Good luck with your search.

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