OwnTrail | Blog

Talking money feels, authentic relationships and tattoos with Aileen McGraw

Aileen McGraw is a Chicago-born, Seattle-based story, brand and business builder. Her why is a world with financial and creative confidence for all. Her words to live by? “There’s no such thing as too spicy.” Naturally, we couldn’t wait to chat with her about her journey.


Your trail begins with a milestone that seems both formative in timing but also in how you experience the world. Why was it important for you to start here in sharing your story?

My trail begins with my type-1 diabetes diagnosis at age four. Why start here? The short answer: It’s one of my first distinct memories. The longer answer: Diabetes is something that is even more enduring than my tattoos. My diabetes is chronic, expensive, hard and sometimes scary to manage, and something that helped me understand who we center in “solutions.” 

My diabetes is chronic, expensive, hard and sometimes scary to manage, and something that helped me understand who we center in “solutions.” 

Think about who is centered in diabetes care: Is it someone who was just laid off? No. The freelance artist? No. The person who wears jumpsuits or dresses? No. Is it the insurance provider, pharmaceutical company, or the insured and employed person who can pay to access the latest technology? Yes.

I mentioned jumpsuits and dresses—they’re a small example of how inclusive design creates better products and experiences. Without, we exclude. Some 350,000 diabetics in the U.S. use insulin pumps (a small, rectangular, and often clip-on device that can help you manage your diabetes). If I want to wear a dress or anything without a waistband, I enter diabetic hacker mode, hunting for underwear to carry the weight of my pump (sturdy thong works best for me!). While not life threatening, the hoops I jump through make me doubt folks wearing dresses were included or even considered at the design table. I am grateful for and privileged to have an insulin pump, and healthcare is a human right, and every diabetic should have free access to quality drugs and medical equipment, and healthcare and insurance providers should include, employ, respect, and love on the diversity of the people they serve.Patient voices matter. Check out the work of Patient Orator CEO Kistein Monkhouse to learn how she and her digital health startup are helping underserved patients document their medical symptoms to empower their voices in their healthcare experience.

The financial milestones on your trail are such a reminder of how helpful it can be to talk about money! Was this an easy decision to include these and what prompted you to share them?

Like diabetes, money problems are part of my life. With lots of friends and therapy, I felt safe and compelled to include my money trail.

Money is part of my story. It’s also part of my anxiety. I literally bite my tongue when thinking about budgeting, negotiating, saving (#IAmMyParents401K), spending, or any number of things I “should” be doing with my money. My #MoneyFeels determine which financial services I trust (very few) and feel confident enough to use (very few).

Money is part of my story. It’s also part of my anxiety.

This is why financial educator Berna Anat and therapist Shani Tran’s Money Please podcast conversations, “Unpacking Your Financial Feels” and “How Do I Address My Financial Trauma?,” felt like a balm for my soul. ✨😌 TL;DR financial trauma and money anxiety are common, they can manifest in our bodies (ouch, my tongue!), and we can care for and heal our traumas with the right support. 

My healing includes storytelling. I love what Tiffany Aliche, The Budgetnista, shared in a recent podcast: “The antidote for shame is voice … shame thrives in silence.” As you’ll read below, I believe learning in the open can create collective hope, skills, knowledge, opportunities, and therefore power.

Thank you to the folks who’ve joined me in some of these stories: Tori Dunlap, Lorena Soriano, Huong Haley, Alberto Covarrubias, Lori Knapp, Jameela Roland, Jenna Rodrigues, Shawon Jackson. You’ve made a real difference in my life. 

A thread in your trail is equity, and it shows up in both personal and professional milestones. Has this always been a central part of your journey? 

Every day I renew a promise to do my own (un)learning, work towards justice, and center those closest to harm in the process. Hint: Words alone don’t do it. (Don’t give me credit just because I wrote something like this.) We gotta live into it: hearts, wallets, bodies, minds, relationships.

Photo credit: Nataliya Khan

My parents instilled care, community, and creativity as life anchors. This gifts so much to my relationships and work. Here’s how I think about my journey with equity:

  • To me, it’s a duh. It’s how I live into my values, the world we each deserve, and the legacies we can collectively leave for our communities.
  • Very sharp childhood experiences (money, mean kids, illness, and more) left me determined to create more care, support, and joy for and by “outsiders.” Heavy air quotes, because the reason folks are “outside” is because of historic and ongoing oppression like white supremacy and its ripple effects. But “outsiders” are “insiders” to beautiful ways of being, dreaming, building. Arlan Hamilton recently tweeted, “When I asked Mark Cuban, a billionaire, why he invested $6M into my fund when he doesn’t usually enjoy investing in other people’s funds, he said without hesitation, ‘you’re in rooms I’ll never be in.’ Think about how powerful that is. You don’t have to be rich to be powerful.”
  • Collective care, healing, accountability, and joy have existed for centuries. Work is one place where I strive to recognize and collaboratively address how equity is often missing, but caring for and creating it is not new. I owe so much to Black, Indigenous, people of color, queer, low-income, and disabled artists, activists, educators, community organizers, and entrepreneurs.

I’m unique, worthy of care, and complex, just like the rest of us. But I carry a lot of privilege as a white, cis, college-educated woman living with an “invisible” disability whose income and financial situation radically changed for the better early in my career. I’ve messed up and mess up; I overthink and overlook too much. Every day I renew a promise to do my own (un)learning, work towards justice, and center those closest to harm in the process. Hint: Words alone don’t do it. (Don’t give me credit just because I wrote something like this.) We gotta live into it: hearts, wallets, bodies, minds, relationships.

Over the last two years, the people leading the U.S. government’s TTS Diversity Guild —which I had the honor to co-lead for fiscal year 2021—have profoundly changed my life. Thank you to Jessyka Castillo, my FY21 co-lead, for showing me what true partnership, space, and grace mean. Thank you to prior co-leads who laid an incredible foundation for care, authenticity, and change: Austin Hernandez, Victoria B. Wales, Cordelia Yu, Deb Baptiste, and Ashley Wichman.

You’ve achieved one of your aspirations: getting a floral arm sleeve tattoo! What about this brings you the most joy?

🥰❤️ Being at home in my body. Defining beauty and care for myself. Witnessing and experiencing magic from my sister and other incredible artists.

The love you have for your sister and the relationship you share with them shines through in your trail. What advice do you have for people aspiring to strengthen and/or prioritize their most cherished relationships?

Find ways to celebrate and challenge each other. My twin sister Eachna and I are each other’s biggest hype-people and most trusted critics. This makes for a flexible, enduring, transformational, and affirming relationship on both sides.

My twin sister Eachna and I are each other’s biggest hype-people and most trusted critics.

Sometimes, we’re thriving and don’t give ourselves permission to relish and congratulate ourselves like, “Damn, you did that!” That’s where the other can light a fire and help you glow.

Other times, we mess up and won’t be honest with ourselves about the risks or harms we’re creating. That’s where the other can spark that reflection and repair, and help you grow.

Also—strengthening our most cherished relationships is hard! I used to tell myself that these relationships should come naturally. But that’s just not true—at least not if natural means simple or easy. Eachna and I are constantly living into the beautiful-but-complicated world of boundaries and communication. For a renowned tattoo artist like they are, that can be them telling me, “Aileen, I need you to give me a day to respond when you need thoughtful advice or feedback.” For a marketer trying to break out of toxic productivity like me, that can mean me telling them, “I don’t wanna talk about answers and solutions right now—can we talk about how I’m feeling?” This shit gets deep, but we also make plenty of time to catch up when it’s #NotThatDeep, like our weekly ritual of chatting Drag Race Season 14.

You’re working on launching a podcast! Tell us a bit about storytelling in the open and what it means to you.

People, communities, and organizations who “learn in public,” as Harold Hughes says, prove how honesty and generosity benefit us all. Learning as we go, and doing so publicly, helps our people grow. 

It’s no secret that those in power have treated building wealth and success as a secret. Competition is real, but—***record scratch***—how real is it when we’re talking about sharing what it takes to try something new, build a business, or pursue our passions?

All this to say—I love process sharing. For my passion and expertise, that means storytelling in the open. I usually do this on an annual basis by blogging about storytellers who inspire me and the tactics they use to create stories with staying power (read my 2017, 2019, and 2021 reflections). Why? Because powerful stories shouldn’t live behind shrouded clouds. They should be accessible, malleable, and open to questions and challenges. My hope is that many more storytellers can thrive as we go.

Seeking examples or inspiration? Here are some incredible open-source storytellers:


Total trailblazer, right? Check out Aileen’s trail to connect with her and follow her journey.

Share