Jillian's Real Life
Aspen

A Dysfunctional Aspen Thanksgiving

Sisters, cousins, Grandma, Winternational ski races, a Cowboy Mouth concert at the base of Aspen Mountain and all the birth-order dysfunction that comes with them.
By
Jillian Livingston
Jillian Livingston with her sisters and their kids at Thanksgiving in Aspen

A Dysfunctional Aspen Thanksgiving

“His voice sucks!” Thumper announced, breaking the spell I was under as we drove up to Aspen for the Aspen Valley Ski & Snowboard Club’s annual fundraiser, when the community gets to ski Aspen Mountain the day before it officially opens. Spoiled? Us? Nahhh!

Daring to scan the radio for something other than Nicki Minaj, I landed on Jim Morrison singing “Riders on the Storm.” I was transported back (as I’m known to be) to my college dorm room, procrastinating on my studies while staring up at my poster of Morrison in his aviator sunglasses, wishing I were the cigarette dangling from his beautiful, slightly parted lips. My twelve-year-old, with his inexperienced ear, zoomed me back to the planet I took off from by reaching his toes to the dial and changing the station back to the same old 100.5 Radio Free Aspen.

With my two older sisters, their five kids and my mother all in town for Thanksgiving and Winternationals in Aspen, I had been reverting to my youth quite a bit since they arrived.

The second my oldest sister, Melanie, walked through my door, I wanted to stick my thumb back in my mouth and follow her around like I did when we were little. That’s the thing about family: as soon as everyone reconvenes, we all slip back into behavior patterns based on our birth order. According to the birth-order profiles I read, as the youngest child I tend to behave like an only child, feel like everyone else is bigger and more capable, expect others to make decisions and take responsibility, and either remain “the baby” forever or become the speeder who overtakes her older siblings.

Wow. That’s tough to accept, but oh so true. On the lighter side, growing up I always accepted my sisters’ dares, which usually meant doing extremely stupid things for entertainment, like eating cookies that looked like dog food (which actually were dog food) or overflowing the kitty litter in the back of the Wagoneer when a sister (Michele) refused to pull over for a pit stop. I did whatever they challenged me to do, just for a good laugh, and nothing has changed. When we’re all together, especially with my mother here, we go back to being the tight-knit family we were as kids: impenetrable, ready for any adventure and prepared to laugh.

Jillian Livingston with her sisters and their kids at Thanksgiving in Aspen
Cousins together in Aspen over Thanksgiving
Family Thanksgiving gathering

But family holidays bring dysfunctional dips that threaten to turn happy holiday highs into maniacal, melancholy lows. We didn’t anticipate that Michele would be taken down hard by back pain, that one of the children would throw up her Thanksgiving dinner from a nut allergy, or that Baddy would find his forty-something wife running up the country road in a rage over harsh words hurled somewhere between the mashed potatoes and the Brussels sprouts.

It’s all good in the end, right? We wouldn’t be who we are without a little family dysfunction and brutal honesty to keep our feet on the ground. So we got over it, and when Melanie, who has been invited to be on a reality TV show, found out Cowboy Mouth was playing a free show at the base of Aspen Mountain before the fireworks, she was all over it. The Aspen Daily News had raved about the band’s Tasmanian Devil of a lead singer and drummer and his talent for whipping a crowd into a frenzy. How could we miss it?

Before the concert, we got a pain prescription for Michele and raced our kids down the mountain on fresh corduroy between watching the world’s fastest women compete on the World Cup course.

Skiing Aspen Mountain on opening weekend
Watching the World Cup ski races in Aspen
Family on the slopes of Aspen Mountain

Then we drank hot cider and layered up for the evening festivities. Arriving slightly late for Cowboy Mouth, Melanie, who loves fur (with the live animal still in it), beautiful clothes (without fur), dysfunctional men and rock stars, ran straight to the front of the crowd. I was going to hang back with my mother, but when I turned around to find her, she too had left me to meander to the front for a better view. Soon we were all up there, kids, husbands and sisters, bopping up and down as Cowboy Mouth belted out magnificent tunes under the stars, steam pouring from our nostrils in the cold night air.

Cowboy Mouth concert at the base of Aspen Mountain

That night, with Wade banished to the bed in the basement, Melanie and I cuddled up in bed together and revisited the funny stories of the day, like Tucker singing “Hey Jew” at the top of his lungs and refusing to believe the Beatles song is called “Hey Jude.”

We looked back sadly on all the changes in our lives lately and sighed big sighs. Then we looked at each other, rubbed noses and realized it was all good, because we had each other and our families, and we would always have our youth, as long as we kept playing together!

Sisters together at Thanksgiving
The family dog
The dog looks sweet, right? She just tried to bite my nose, but I got away, and Melanie captured it!
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Testimonials

Corneliu Fagaraşan
Architect

Aspen Business Connect completely exceeded my expectations. From the moment I showed up I felt welcomed into a community of open, curious, and genuinely supportive people. It’s not just networking—it’s real connection. I’ve built friendships, found opportunities, and gained invaluable insight simply by being part of the group. The environment Jillian has created makes it easy to show up, be yourself, and grow both personally and professionally.

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Hudson McNamee Osprey Design Studio
Owner

I came along and was immediately connected with a lot of entrepreneurs from all backgrounds. A year and a half later I have gained a plethora of connections and advice from people from all walks of the entrepreneurial journey. This valley works by word of mouth. That is the most effective way, and being a part of this has gained me the most high quality clientele that respect what I do, compensate me fairly and I don't have to go through the entire vetting process every time. I learned so much from so many different types of people. It's been invaluable to my growth as an entrepreneur and a small business owner.

Grayson Rutherford Sinclair Building Architecture Design
Director of Operations

I've been blown away by the professional connections that I've been able to make since joining Aspen Business Connect. I've even had the opportunity to make trade relationships... [and] brought multiple artists onto my company's projects that I wouldn't have otherwise found had I not been a member of ABC.

It's unmatched and unrivaled by anything else in the valley and such a special meeting and connecting place for professionals of all different backgrounds. Jillian does an incredible job making her network ours and she's the most well-connected woman in the valley, always bringing in new people from different places who have different experiences and backgrounds to share. Overall it's one of my favorite things to be part of in the valley, from our socializing events and specialized dinners to our more professional focused events , it's given me the opportunity to make great friends in the valley and even professional relationships. All of us are better off for it.

Jeremy Joseph
Jeremy Joseph Photography

I opened a gallery called Jeremy Joseph Photography, which was a place to display my fine art prints of the Colorado Wilderness and Wildlife. Shortly after opening that space, I started to realize the need for me to be more  integrated into the local community. After a short meeting with Jillian, I realized really quickly how valuable her network could be to get more integrated into the community. The amount of people and relationship building you can do is pretty impressive. Every time that I show up  I always have a bit of a vibrationally tingly inspiration because of everyone's stories and what they're doing. Just a great place to be a part of the community and get inspired for your small business.

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Derron Cloud, State Farm Agent in Basalt and Aspen.
Agent

What I have enjoyed from Jillian's group, Aspen Business Connect, is I've met lots of different people, different individuals. There's great events. I have probably not only gained clients but I’ve also been able to provide clients to those other folks that I've met. I've also made friends. Several people that I met in the first meeting that I went to, I've played golf with and our families hang out together. I have also had many, many referrals from those people. This group has been fantastic for networking and learning and just meeting lots of great and wonderful, interesting people.

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Dominic Del Signore Homestead Circus Productions
Founder

Being a member hasn't just grown my business; it has fundamentally changed my life in the Roaring Fork Valley.

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Jillian is a master at the art of connection, and her dedication to this community is nothing short of brilliant. She understands that when you connect local businesses as genuine resources for one another, you aren't just facilitating 'transactions', you are proliferating a culture of friendship, growth, and playful engagement that makes our community thrive... Great organizations only succeed with great leaders, and Jillian’s mission to foster an environment where we all succeed together is incredibly effective.

Marisa de Lempicka Tamara de Lempicka Estate Foundation
Owner

I've been a member with Aspen Business Connect for about five years now and it's been wonderful. Jillian does an amazing job at connecting people. I always leave the events inspired, empowered, with new ideas. It's really really been a great addition to my life here in Aspen, and it's a great reason to hear what other people are doing in the community, to feel part of this amazing community. The people in this group are amazing. I've /made some really lifelong friendships.

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Shari Havroud of Aetio Health
Nutritionist
I am so grateful for Jillian and Aspen Business Connect, for introducing my work to the team at Aspen Strong where we created a successful Food/Mood kids series.  From there, I have been given the opportunity to work with the Aspen Youth Center, Aspen Family Connections and the City of Aspen!” 
All of these engagements have helped me expand awareness about the benefits of medical nutrition therapy.  Just one introduction led to many more.  I would highly recommend joining the Aspen Business Connect network!"
Diane Utz, ESQ Ferguson Shindler Law Firm
Construction Litigation

Thank you once again! You’ve created something really special and have done an amazing job pulling together the movers and shakers in this Valley. I’ve lived all over the country but have never witnessed a network like the one you’ve built and are continuing to build. You are such an inspiration!

Eric Amyot Keystone Species CO
Instigator of Change | Generative Community Builder

ABC makes networking easy. More than that, the intention and energy, mood, and support for every entrepreneur and business regardless of their scale or industry, is always positive.

Harry Teague - Harry Teague Architects
Owner

Thank you Aspen Real Life and your team. Very informative and well organized panel discussion. Wonderful to network with such smart, fun crowd. Keep up the good work.

Jerome Osentowski Central Rocky Mountain Permaculture Institute
Founder & Director

Last week Jerome, Eden, and Brook melted our minds with their wisdom on the state of our food systems, what they're doing about it, and what we can all do to improve the health of ourselves and the Earth. Thanks Aspen Business Connect for organizing this great event!

Thanks so much Jillian for putting these together. We were glad to see so many people who care about their food, we got so many business cards! Amazing

Rose LeVan Sustainable Settings
Co-Founder & Office Manager

Thank you Jillian for giving us the opportunity to talk with our community via Aspen Business Connect! Your crew is amazing.

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Michele Cardamone - Michele Cardamone Photography
Owner

I just went to Jillian's Aspen Business Connect meeting at Aspen Kitchen with a panel discussing the importance of eating local and nutritious food without pesticides. There was so much positive energy in the room and such an eclectic mix of local business representatives. It was such a perfect way to connect with members of our community. Bravo, Jillian! I can't wait for more!

Molly Dodge Bosque Aspen

Such an amazing event, Jillian!! Thank you for including us and for everything that you're doing for this community and beyond. You're an inspiration and connecting people is the most satisfying thing. Xoxox

Bill Infante, Hangai Mountain Textiles, Co-Founder & President at Breakthrough Communications, Basalt Town Council Member.
Principal & Co-Founder

Great evening. Great initiative. Great connections. Thanks Jillian Livingston for bringing the business community together!

Marisa Hallsted The Mindful Vine
Founder

We thought you’d love that we all connected over a fabulous dinner. Turned into a blog post, a mastermind group, a newly designed ring from gems from my ancestors and who knows great collaborations between some of us in the future! Thanks for being our connector and for all you do!!