And that has made all the difference.

Hi friends, 

I’m at a crossroads in my life where I have to decide between continuing to dream big or settling for practical. This fork in the road reminds me of another moment in my life when I faced a similar choice: it involved writing a letter. 

When I was in high school, I was responsible for coordinating a silent auction with some of my classmates. In the theme of dreaming big, I thought there was no better way to leave our mark than to get some items that people would be surprised to see at a high school fundraiser. As the pop culture queen that I am, I began writing letters to any and every celebrity I could think of who might be interested in donating to the cause. Keep in mind that this was in the early days of Instagram and DMs (though maybe one day I’ll tell you about how I basically invented DMing when I reached out to a reality star on Myspace…), so I spent hours researching fan mail addresses to send these petitions to.

Although I wasn't a particular fan (I know, I know, hate me later), I sent a letter to Kobe Bryant. But it never made it to him. Instead, it was returned to our high school address and put in the mailbox for the program that this fundraiser supported. 

I was sitting in the library one day when a fellow classmate, and one of the leaders of said program, came up with the letter in hand and laughed about how I had sent it to Kobe Bryant in that eye-rolly, condescending, “Nice try, sweetheart, but it’s never going to happen!” sort of way. She joked about the handwritten message I had included (probably something to the effect of, “We’re such big fans!” Sometimes you have to lie, people.) and the unlikelihood of him ever seeing it. 

At the time, I felt so embarrassed. I didn’t want other people to know that I was spending my free time writing these letters; I only wanted them to know if my efforts were successful. I felt exposed and foolish, as if a response to my outreach was so improbable that it became entirely comical. 

 

In that moment, her words shut me down just enough, and I didn’t send any more letters. 

Four years later, the wound had scabbed over, and I decided to risk writing another one. This time, to Jesse McCartney. 

If you know me at all, you know that Jesse has been the object of my affection since I was four years old. I had the opportunity to meet him for the first time in 2018, which was a surreal experience that I later detailed on this blog. Heading into this momentous occasion, I knew I would have a limited time to say what I wanted to say, so I decided to write a letter. I didn’t want to come off as too obsessive, but I did want to detail how influential his art had been in my life over the previous two decades. I drafted and drafted and eventually came up with a message that was both authentic and (relatively) concise. 

The meet and greet had two parts: a small group hang on his tour bus and a photo op as part of the larger group. I handed him my letter toward the end of our time on his bus before being ushered back to the venue to get in line for photos. I didn’t expect him to read the letter right away since the turnaround between the two parts was pretty tight. In fact, I didn’t even expect him to read the letter at all – I just hoped he would. But as I walked up for my official photo with him, he told me that he had read it and proceeded to have a full conversation with me about it, where he offered some very kind and encouraging words. He remained turned towards me, sharing what it had meant to him, even as the next person came up to take my place. Wiiiillllddd. 

That same year, I kept the momentum going by writing a letter to my biological grandfather’s family asking for a photo of him. Some of you know that my mom was estranged from her dad for pretty much her entire life for many reasons, including that he was black and the rest of her family was white. He died when she was twenty-one, and they never had the chance to reconcile. Growing up, I knew of his existence, but I didn’t know anything about him. We didn’t have photos, letters, anything. All we had was a death certificate reminding us of the missed opportunity to know him. 

Over that summer, I was on a sunset walk with my dad in Sunriver, Oregon, when I told him about my idea to write this letter. I had found one of the family member’s addresses on Google and felt like it was worth taking the shot. He was supportive, but chuckled a bit at my lofty ambitions, reminding me that my chances of hearing back were slim. This time, I didn’t let it stop me. I penned my message a few weeks later. A few days after that, I received a call from an unknown number. It was my aunt. What transpired was a series of phone calls, healing conversations, and introductions to new family members that we've now built permanent relationships with. And I got that photo I wanted (and then some!).

Two years after that, I gave letter writing another go at another meet and greet. This time for the man, the myth, the legend, Bachelor Ben Higgins. As my bestie and I got in line for a photo, I gave the handler a letter and asked her to give it to Ben. I wanted to share with him how his podcast and time on the show had impacted me, but I also wanted to share my admiration for the non-profit that he runs. I was about to graduate, so I thought, “What the heck?” and threw in my business card as well. 

Three years later, I was back working at the same institution as grad school when I got an email from, you guessed it, Ben Higgins. He said that he had found my letter and wanted to know how I was doing and how my life was (seriously, what a guy). I forwarded it to my personal email, where we sent a few messages back and forth. During which, he seemed genuinely interested in me as a human and eager to share his own insight on what my next steps could be. I’d now like to think that if I were in Denver, where he lives, I could reach out and ask to grab a friendly coffee without it being totally weird. 

These are just a few examples, but letters, in print and digital forms, have quite literally reunited my family, facilitated connections with public figures I care deeply about (those mentioned and others), allowed me to make multiple guest appearances on a NYC-based fitness show, opened doors to job opportunities, and deepened the connections I have with friends and family in my real world. They have become an essential part of how I communicate, which is why many of these posts are framed as some sort of letter to you. 

I could’ve let the laughter dictate my choices twelve years ago by resigning to a life of realism. But instead, I got up and chose the path of wonder. So, I guess the message for me and for you is to dream big. Write the letter. Do the thing. Perhaps, in my case, post the video. And, if you don’t, please don’t make fun of those who do. Try encouraging them instead. 

 xx

Abbey

Titular Reference: The Road Not Taken by Robert Frost. 

Some may consider this poem “overplayed,” but it’s always meant a lot to me. I reference it often and encourage you all to revisit it if you haven’t in a while.