Jillian's Real Life
Aspen
Badass Professionals

The Beginning of Aspen Real Life

How a stay-at-home mom with a film background started Aspen Real Life in 2009, from mommy blogging and travel writing to a digital magazine.
By
Jillian Livingston
View from the Livingston family's Red Mountain cabin in Aspen

Aspen Real Life began in 2009, when I decided I wanted to be a SAHWM, a stay-at-home working mom.

I had read about Heather Armstrong, the pioneer of mommy blogging, who was making more than a million dollars from her “reality” stories about life, religion and parenting. She was doing so well that her husband was able to quit his job and join her. “I can do this,” I thought. With a background in film production and publishing, I knew that while I didn’t have Dooce’s brazenly raw tone or her compelling story of growing up Mormon and leaving the church, I did have my own quirky, positive voice.

We were in financial distress, and I needed to brush off the professional dust that settles when you’re raising babies and do my best to keep our ship from going down. I had always felt that raising children was my calling, so I had to figure out how to work from home.

I was setting up a website, writing stories, juggling family life and doing my best to keep my relationship with my husband strong. Somewhere in the transition from 12- to 14-hour days in film production to being a mom of three boys, it came to me that perhaps I had been over-mothering our children. The tough love began, and they miraculously readjusted. Without me waiting on them hand and foot, they blossomed, attacking their chore list, learning to cook their own eggs, grill their own dinner and find that elusive enormous white milk jug in the refrigerator. Nevertheless, the house was a mess, the kids felt neglected and I fantasized about stealing away to Mexico with my laptop to do nothing but write in peace, wearing a large floppy hat, enormous dark sunglasses, a sarong and a skimpy bikini (yes, I’m delusional).

Instead, when Wade was home to manage the boys, I plugged away in my office. An occasional little face would peek in to check on me and be met by a Rottweiler mommy foaming at the mouth and baring sharp teeth to warn against the interruption. Then Wade would appear. I’d look up, fingers still typing, and he would smile, blow the smoke off his imaginary gun and say, “Don’t worry, Mama, I’ve got this.”

Taking Off as a Travel Writer

I applied to be an advocate for Colorado tourism and received an assignment to go to Wolf Creek, and dun, dun, dun, I began travel writing, which gave me the incentive I needed to keep going. I wasn’t making any money, but at least I was taking my family on trips we could never have afforded otherwise.

As I delved further into blogging, I kept envisioning myself and my family sitting on a plane on the runway. With each step forward, the plane would start moving and slowly creep along in preparation for takeoff.

Through my travel writing, I became a freelance luxury travel contributor for Inspirato, Quintess and the St. Regis magazine, Bespoke. I also became the Roaring Fork Examiner. But blogging is a lonely world. Like Miss Piggy visiting her mailbox every day hoping for a letter to show that somebody cares, I checked my analytics obsessively. “Is it kind of like weighing yourself every day?” my SEO consultant asked me, staring into my eyes with a subtle innocence.

It was always my readers who kept me going, but eventually that wasn’t enough. I needed to monetize everything I was doing: the podcast, the radio show, the blog. It often felt like I was swimming through cement without a soul out there to help me. I was completely on my own.

What kept me going was the mantra playing in my head from Malcolm Gladwell’s book Outliers: 10,000 hours for success, 10,000 hours for success. There were times I didn’t sleep, eat or work out, and the fur grew on my teeth, my legs and my armpits, and all the while the joke in the house was, “Guess how much money Mommy made today? Nada cent.”

Nevertheless, my plane kept moving forward on the runway with the occasional hump to get over, JetBlue style, where I’d be stuck in my own tomb for eight hours. But that only led me to reevaluate my path and make necessary changes.

Connecting with My Community

As my stats grew, mostly from out-of-town readers, I decided it was time to connect with my community, even though I preferred the anonymity that gave me more freedom to write from the heart.

Social media became my MO, and instead of treating it as a mundane requirement, I embraced it. This new paradigm was bringing back the barter system, Davy Crockett style, and it was a beautiful thing to discover that my writing and interviews could bring business to my friends, and in return they grew my audience.

Around the time parenting transitioned from wiping bottoms to jail prevention, Aspen Real Life had a midlife crisis. I was running out of time and money and kept hitting walls trying to find partners to take Aspen Real Life where it needed to go. The good life came to a screeching halt. I had teens to parent and bills to pay. I needed to do something fast and actually make some money. I hit the pavement running and left no stone unturned. It was time to get a real job, so Aspen Real Life went on the back burner and I went to work for a hot digital marketing firm in Aspen, directing all my energy toward promoting other businesses on social media.

Three years later, I’m back, returning to my passion with new gusto from my digital marketing job. I’m ready to take Aspen Real Life to the next level and monetize it, believing that if I’m passionate about what I do (taking adventures, exploring new places, connecting people and businesses), I’ll wake up every morning excited to start my day, and soon it will all finally begin to happen. It has to.

Soon we have to move yet again so the rest of our boys can be in the Aspen School District. And sooner than that, all of my creative side projects will be running smoothly, and THEN, and only then, will the nose of my airplane lift off the tarmac, and I’ll fasten my seat belt as I soar into the air.

Update: We did move, to a teardown cabin on Red Mountain, and had four glorious years with the most incredible views you’ll ever see.

Interviews Over the Years

  • Aspen Film
  • Powder Magazine
  • Kenyon Martin
  • Ramona Bruland, Plum TV Aspen
  • Pam Sweeney
  • Nick DeVore
  • Jake Sakson
  • Ken Quericone
  • Cole Tamblyn
  • Michelle Manning Kogler
  • Dr. Jefferson Roth
  • Stan Cheo
  • Cameron Scott
  • Terry Butler
  • Cosbar
  • Anton Uhl
  • Laurie Carney & William Grubb
  • Sheri Gaynor
  • Summers Moore
  • Katalin Domoszlay
  • Chris Davenport
  • The Nature Conservancy
  • The iTraveler
  • Black Shack Architects
  • Walford Williams

Product Features

  • Vizzibl Clothing
  • Columbia Sportswear
  • Two Leaves and a Bud
  • Transpack
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Sponsors

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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!!