Step One: Pick a partner in crime. You definitely want to pick someone who you love doing things with and who (like you) wants to try new things.


For this adventure my big sister Sarah and I went into Chicago.  We got dressed up and prepared ourselves to have a fun night.  We realized that having fun meant doing whatever we wanted in the moment, that would be what we did.  When you set out to have an adventure you need someone who is willing to try new things, let you be you, and someone you can have a blast with no matter what you’re doing.


Step Two: Be ready for anything! I’m not suggesting that to have a fun adventure you will always be pushed outside your comfort zone, but it a good possibility that if you challenge yourself to do something new, silly, or even just different you will find things to do you wouldn’t normally have done. Which is by definition an adventure.

  1. an unusual and exciting, typically hazardous, experience or activity.
    “her recent adventures in Italy”

One of the best gifts given to me by another one of my adventure partners were these ANYWHERE cards. It is just one way to challenge myself to make an adventure out of going “anywhere.”anywhere


On this adventure I had to climb things, which may seem silly, but it really did make a difference, just giving me a new perspective, and something to do that I honestly wouldn’t have done normally.

Step Three: Try new foods.  I would have never discovered that I love Oysters had I not been willing to try new foods.  In this adventure, both Sarah and I had the same desire to try a food that both of us had previously disliked, but wanted to give it another go.  We both had poor experiences with this food, it was not well prepared and truthfully just was not good. Lately, however, both without realizing the other was feeling the same way, we each were feeling curious again about this food, so we ordered it.


This Octopus was well prepared and perfectly seasoned… but we both had the same feeling about it… tasty, but not necessary to try again.

Step Four:  Always sit at the bar.  I find the source of most my chance encounters are at restaurants or coffee shops whenever there is close proximity to strangers.  More often than not, we need to get over our childhood conditioning of stranger danger.  Meeting new people is one of the best ways to open yourself up to new experiences, and it all starts with not being afraid to say, “hello.”

IMG_1954 Meet Emily.  She introduced Sarah and myself to a new wine we would never have been able to try without meeting her.  She has had a very interesting life, that led to her ordering this bottle of wine while sitting next to us at the bar.  The passion and excitement she had about this wine was like a child on Christmas morning staring at the pile of wrapped gifts under the tree.  I recognized this excitement because it is so often present in myself whenever discussing food or wine or travel, and is especially present when all three of these things intersect for me. This is a quality that I believe most humans share, but it is always fun to see how it expresses itself in someone else, as it did in Emily at this moment.  Thanks to this chance meeting with Emily, I got to taste a wine that I will never again get to try unless I travel to the island on which it was made. (more about this in another post)

Step Five: (and perhaps the most important step) Wear comfortable shoes.

IMG_2015 The reason this is so important is because you can’t truly complete step two without comfortable shoes.  Half way through your adventure all you’ll be thinking about is your aching feet, and that will put a complete damper on the whole experience.  Your feel will take you so many awesome places, but you have to be ready, which means not killing them two hours into the adventure.

It also is the most important step because it allows you to keep your eyes open to the adventures that may present themselves.  You can’t see anything fun in front of you if you can’t find the will to make your feet walk there, and without comfortable shoes, you’ll never will your feet to take you toward the experiences that are going to take a simple night out on the town and turn it into an adventure.

There is one more step to the secret of my success. It’s a bonus step to making your own adventures anywhere you go: Surround yourself with generous awesome family and friends.  It is what I would call a bonus step because I don’t think I have much choice in the matter.  I just have awesome people in my life, and to be honest this night would have never happened with out my partner in crime choosing me and making the plan.  She bought us tickets to an amazing concert, (something I would never have done).  She treated me to the entire evening out of the goodness of her generous heart.  It’s when you have fantastic people in your life that you are bound to have fun adventures together.  Thanks to my sister Sarah, I had one of the most fun nights of my life, and we didn’t even do anything illegal!  That’s why surrounding yourself with awesome people is so important to great experiences, without someone to share these experiences with, they’re not nearly as fun.