Forgive me, but it’s only been a month and a week since I decided to sell my place and work remotely––so if you’re finding out about this news from this letter, know that it’s 100% nothing personal, I’ve been running around like a racoon the morning of trash day. I love you, I promise!

Commence Clothing Confidence 365+ Tour 

I pride myself on rational thought. It’s long been a cornerstone of my personality and written on me like a nametag. Maddison DATA McKinley.

So it may come as a surprise to many that I have officially sold my first home and am trading in my comfortable (rational) lifestyle for a nomadic, unpredictable one. I’m following my heart (wait, did I just write that?).

In a couple of weeks, I’ll begin traveling across the country in my Nissan Versa with 36 pieces of clothing and my electronic gadgets––all in search of experiences and people to fuel the Clothing Confidence movement. I’ve sold everything I own and am turning the keys over to Americana to show me to my destiny.

So now I turn to you because this adventure is a “crowd-sourced” one. I want your help in figuring out where to go, what to do, and who to meet. Tell me about your favorite coffee shop in [insert town here], or that stylish friend you know in [insert town here] who has great style. 

This is the number one way you can support me. Fill out the Google Form >>>

If you want to stay in the know about the Clothing Confidence 365+ Tour, bookmark this page (it’s the “homepage” for the tour) and follow me on Instagram, @DailyInspirato. This is where you can ride shotgun with me on my journey. Also, subscribe to emails. I cannot wait to share my experiences with y’all!

Frequently Asked Questions

• Where are you going first? I don’t know yet. I need your help deciding!

• Are you still going to have a job? Yes, I will. Praise be to God my 9-5 has allowed me the opportunity to be zipcode flexible.

• Are you going to be driving in that tiny a** chickpea/Campbell’s-soup-can-with-wheels car of yours? Yes, I will be taking Ver[s]a. She just got new brakes, tires, and and an alignment (+ all new filters). I will be driving her to 150k, and we’re only at 88k now.

• Where are you going to be staying? AirBnBs with high speed internet access. I will be staying with family and friends as they allow.

• Are you really doing this in the middle of a pandemic? Yes, I am. 

• Why 36 pieces of clothing? I have stripped down my wardrobe to 36 pieces because I want to illustrate how a Dynamic Personal Style and the 4Cs look within different style genres. Check out the Styled Series to see how the looks come together. I will only have 36 pieces of clothing at one time, and the rest I’ll sell on Collection36.

Any other questions? Leave them in the comments :) 

Departing 295 South

On an even deeper personal note, I want to communicate that coming to this conclusion hasn’t been an easy one. Leaving behind something you’ve built yourself and that you’re proud of is really hard. I’ve never experienced this kind of twisted, bittersweet, happy and sad at the same time, kind of pain. I’ve usually left situations ready to leave them. Leaving Portland is different. Saying goodbye (for now) to great people, places, and things is so much harder to do when you’re happy. But, alas, I’m scratching the invisible itch of “something more” and doing it. The deeper I get into this journey, the better it feels.

Portland has been a place of firsts for me: first apartment, first professional job, first boyfriend & subsequent breakup, first time discovering something I’m passionate about (Clothing Confidence), and so on. I came to Portland seeking refuge and I got so much more… I got a beautiful life

So it feels poetic that I’ll be hitting the road in the same Nissan Versa that brought me liberty and freedom 5 and a half years ago (the first time “Nissan” and “poetic” have been in a sentence together). I remember the feeling crossing into Maine state lines, it was like I could take a deep breath. I didn’t know what was in store and I certainly didn’t know how fantastic my time here would be.

As I cross out of Maine, my heart will be heavy to leave it behind, but something tells me I’ll be back soon, and maybe with a new name––Maddison ADVENTURE McKinley? 

🥂🍻 Feels unlikely but here’s to looking forward to the unexpected. 🥂🍻