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Finding Your Direction: Lessons Learned from Cassie's Entrepreneurial Journey

Updated: May 17, 2023

Approaching Her Sorority Journey's third anniversary, Cassie reflects on her career trajectory and lessons she's learned from three years of entrepreneurship on her 27th birthday:

Three photos. From left to right, Cassie Little sitting on the floor of a closet with her laptop starting her business. Cassie Little speaking in front of a group. Cassie Little speaking on stage in front of a crowd for sorority recruitment.

young Cassie Little with a park ranger and a young boy posing for a photo

Growing up, I wanted to be a park ranger. I was obsessed with National Parks. One summer, I helped my mom plan a 30 day road trip in an optimum route for hitting as many National Parks as we could. From Portland, OR, we drove as east as Mount Rushmore and as south as the north rim of the Grand Canyon. We hit 25 National Parks that summer.

In college, I thought I would be a lawyer. I double majored in Business: Law & Business: Spanish Language & Culture. I even took the LSAT a month after running primary recruitment on the Panhellenic team. lessons learned from entrepreneurial journey

Today, I run an interactive and engaging sorority educational platform that reaches 100,000 of sorority members where they’re at: on social media and college campuses to give them the support they need to find healthy confidence, true belonging, and authentic community in college. Founding, building, and growing Her Sorority Journey these past three years is a career path I never would have dreamed for myself, but reflecting on who it has impacted & who I have become because of it, I can’t imagine ever having invested in any other profession.

When I turned 24 on March 2, 2020, I had already spent two months creating a business plan, casting vision, and writing curriculum for a business that would support sorority women. When I turned 24, I did not feel the “girl-boss,” entrepreneurial energy. I felt scared. I felt pressure to make this work given all the sacrifices I had made to commit to this up until that point. And that was all before the country shut down for COVID-19 precautions.

Sometimes I regret that I didn’t do more when there was nothing else to do besides work from home, go on walks, and make whipped coffee. But then I remember, thats when this started. When we were learning the latest TikTok dance together, we were also creating community around how to run a fully virtual recruitment. After logging out of class via zoom, our clients were meeting with us for zoom chapter meetings.

When I’m traveling to a different state every week to work with a new chapter or community, it’s hard to remember that this is where we started. The seasons in between the extremes of how we began and where we are today are what gradually shaped the business owner, speaker, and content creator I get to be for our sorority communities today.

While there have been countless lessons learned professional & person, here are a few I’m reflecting on as I turn 27 today:

Your people aren’t abandoning you - don’t abandon them.

It is vulnerable to start a business based on a pain point you have felt in your own life. It’s risky to start a new thing and hope it works out. Early on, I found it was hard to share what I was working on and how it was going honestly with those who cared the most. But since my life mostly consisted of building this company that I was figuring out day by day, I started to withdraw from a lot of friendships. Looking back, it feels like I was hiding until I had something to be proud of to share with people. I often hear entrepreneurs lament that their friends are unsupportive of their new ventures. But I have to ask myself, were my people not supportive or was I too embarrassed to let them in? Working for yourself more than ever have I found it important to invest in my friends more than they invest in me. Ask them more questions than they ask me. To prevent hiding from my support system or being self-absorbed, I learned the importance of diving into my friends and families lives and stories with a genuine care for our relationships.

Three photos. From left to right, Cassie Little in the middle with two girls on each side hugging. Cassie Little with her Executive Assistant Lindsey. Cassie Little with six friends on a snowy mountain.

You’re allowed to relieve the pressure.

I have gone through seasons over the past few years where the pressure I felt to prove something to myself on top of the pressure to sustain myself financially was too much to bear. Through a lot of humility, I learned that it is okay to relieve that pressure to protect the purpose and vision of what you are building. Since I started creating content for Her Sorority Journey, I have also worked the front desk of a gym, taught fitness classes, dog sat, been the events director for a church, and the social media director for a political campaign. None of these roles brough the joy, confidence, and alignment of vision that Her Sorority Journey does but they served a purpose. In some roles, I needed to be a part of a team to work collaboratively on a collective goal. In others, I just needed the security of a paycheck. But I learned that there is no shame in taking on additional streams of income to relieve the pressure of your passion project. And truthfully, when I put my pride aside and worked on Her Sorority Journey part time was when it grew beyond my ability to let it only be part time. It’s amazing how something can grow when we give it air to breathe.

Three photos. From left to right, Cassie Little standing with a woman outside of a church, Cassie Little encouraging a woman during a workout class at Barr3, Cassie Little taking a mirror selfie with her dog

Every season has a purpose.

Her Sorority Journey & I have gone through extreme seasons together in the past 3 years. We’ve gone through months of multiple podcast episodes a week and monthly live workshops (early COVID) to a singular TikTok post a week while traveling to speak to chapters multiple times a month. We have spent seasons focused intently on social media and others trying a variety of different marketing strategies to reach sorority members. Looking back I see how much we learned from trying so many different things in certain seasons and focusing narrowly in others to strive for consistency now.

While some of the seasons in between the extremes I wished would have gone faster than others, the lessons I’ve learned will stick with me forever. I would not have the opportunity to be the person I am today without the long trying seasons of patience and Her Sorority Journey would not serve sorority members the way she does without the trial & error.

We end most of our keynote programs with the challenge for our attendees to “embrace their journey.” Recognizing that each season of their sorority journey only better equips them for the one to come. No season of your journey is ever wasted.

Three photos. From left to right, Cassie Little overlooking a lake at the bottom of a mountain. Cassie Little handing out PR baskets at a Colorado university to sororities. Cassie Little working at her laptop outside of a coffee shop.

My hope for all of you is not that you go on to be sorority content creators or even entrepreneurs. It’s just that you give yourself a lot more grace with the mistakes you make, what you learn, and to validate when your heart aligns with a profession! So early in our life we discount our childhood dream job because it’s unrealistic but rarely do we go back to reevaluate what made us excited about that path at a young age.

When I think about why I wanted to be a park ranger, I think about how I wanted future generations to get to gasp in awe at the beauty of nature and appreciate the preservation of land just as I got to. I wanted to live differently to make an impact in creative ways for generations to come.

I basically get to do that now without green pants or wildlife.

Empowering sorority members to see the beauty in their community, relish in the rich tradition & sacrifice of those who came before, and be mobilized to restore their chapters & communities for its preservation for generations to come is a childlike dream I had.

So here’s to you reclaiming your childlike creativity, ambition, and unapologetic enthusiasm for what sets your heart on fire. Your passion for contributing to your sisterhood or your society can be found in what you wanted to do when you had nothing to prove.


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