My unexpected adventure from a college dorm room back to speaking at that same college—and the BIG lessons I learned the hard way

Jason Dorsey speaking at UT

I wrote my first book at age 18. I remember exactly where I was sitting, the look of my dorm room, and the dim light that was shining on my notepad at the tiny wooden desk that seemed permanently attached to the wall. It was Jan 7, 1997 at 1:58 a.m. I was on the 18th floor of the dorm room directly adjacent to the University of Texas at Austin campus and right above the bustling street known informally as “the drag.” 

I had just made the decision to take a break from attending college and go all-in on my newly identified life purpose: helping others, especially those facing adversity. 

I deeply wanted to commit to this path and follow this new purpose, but I was scared. Really scared. I knew my parents would be extremely upset (that ended up being a gross understatement), I knew I would put myself in financial hardship (I soon ended up sleeping on a floor), and I knew I would be leaving my clear path that had been repeated to me over and over—go to college, get a degree, get a job, move to a big city, and build a career—and instead would be jumping feet first (maybe head first!) into the unknown. It was a feeling of being truly alive, in the moment, scared, and inspired. I knew not the journey ahead (I probably would’ve chosen something else), but only what I was leaving behind. 

 So much happened since that early morning when I committed to my purpose. 

Twists, turns, setbacks, breakthroughs, heartbreak, disappointment, sleeping on a floor, falling in love, becoming a dad, and so much more. But I persisted. And now, these many years later, I ended up directly across the street from that dorm room overlooking the now highly developed UT “drag” about  to speak to  students attending that same college I attended and who were the age I was back then! Talk about deja vu. 

I also wanted to make the most of coming full circle back to where it all started. So I took a big risk while back on campus. Right before my informal speech I decided to try something I’ve never done before as a speaker. I had ZERO idea how it would work out. That risk ended up reframing how I saw my own story, my own journey, my own decisions, and how I’ve grown. 

First, the back story…  

 For the last many years, I’ve been a guest speaker at a Leadership class taught by Bill Cunningham and John Mitchell. Dr. Cunningham was the former Chancellor of the UT System and President of UT Austin. He is an expert in corporate board governance and executive leadership—and an amazing storyteller. John is a serial entrepreneur with a passion for studying the practical application of mindset and an expert on Napoleon Hill. 

 Speaking at UT is important to me because this is where my path came to light. In fact, it was a guest speaker at UT who inspired me to find my purpose—which led to me writing my first book at age 18. What a world. Speaking to Bill and John’s class gives me the chance to come full circle, and their students are always so excited to hear an unorthodox story of discovery. 

 But this year, I wanted to do something different. Unlike corporate keynotes on big stages and fancy boardrooms, when I speak at UT, I intentionally have no slides. No case studies. No talking points. Not even an intro. Instead, I wear jeans and a short-sleeve shirt and jump right into the conversation by asking the students questions about themselves, their career goals, and life aspirations. I then share the non-Wikipedia-approved version of my story, starting at age 18 with all the twists (writing a book at age 18), turns (ending up on national TV at 20), failures (businesses going out of business), challenges (not fitting the traditional checkboxes), gut checks (too many to list), and breakthroughs (not giving up) that led to me getting to now do what I love every day. 

 This time, however, I prefaced my story by asking the students to help me uncover the lessons I learned in my journey. Sometimes when you are the story, you don’t see the lessons others see. Wow……….. I was not ready for the responses! I learned so much from the students, especially after being so vulnerable when sharing my story. 

 Here are some of the lessons the undergrads helped me to see in my journey: 

  •  It’s okay to not fit in. It may hurt or make you feel alone, but you’ll find your people. You just have to keep being who you are. 
  • There is no one-size-fits-all path for education, careers, or life. And just because people tell you to take one path, that doesn’t mean that is the right path for you.  
  • Keep learning and adapting. Every. Day. Some lessons feel much harder than others, but the key is to put the learning into action fast. Learn. Adapt. Repeat.
  • Ask for opportunity. Ask for opportunity. Ask for opportunity. In my case, I kept asking the people I met, “Well, how do I do that?” and it kept opening doors. 
  • Get mentors. Respect their time. Come prepared. Put their wisdom into action. Share with them the results.
  • Have an emergency savings account. It will buy you time and give you options. 
  • Help others. 
  • Have patience. And determination. You need both.
  • Solve a problem for someone else. That often is the seed of a business.
  • There is a big difference between knowing a skill and mastering a skill. After 1,000 standing ovations, I’m still learning and trying new things at every presentation. In fact, this year, I have all-new slides and all-new content and have changed my vocal range. 
  • Remember that people helped you along the way. Help others. 
  • It’s okay to fail— a lot. The key is to not give up. 
  • Just because something is your passion doesn’t mean it has to be your occupation. But when you can combine both, it’s awesome. 
  • Every one of us has something valuable to bring to the world.

 What a journey it has been, from UT Austin and now back to UT! I had no idea how much I would learn, how low the lows would be and how high the highs would be—such is a life adventure fully embraced. 

I’m grateful to get to learn every day on this journey, including from these ambitious undergrads who were so kind to share their candid feedback. What a journey. 

Thank YOU for being on this journey with me! I learn from you, your feedback, and your comments, too. I look forward to many more adventures together—including us coming full circle and connecting at an in-person event again.

Gen Z Generations Keynote Speaking


You may also be interested in:

You Might Be Wondering: Does Our Speaking and Research Drive Results? Video Proof: Repeat Client Shares Their Experience Solving Generational Challenges

I love working with repeat clients because I get to know their team, culture, challenges, opportunities, and strengths over a long period. Going into the details with clients and working with their teams consistently also builds momentum for action, buy-in, trust, innovation, and results across their organization.

Generations Keynote Speaking Workforce

My unexpected adventure from a college dorm room back to speaking at that same college—and the BIG lessons I learned the hard way

I wanted to make the most of coming full circle back to where it all started. So I took a big risk while back on campus. Right before my informal speech I decided to try something I’ve never done before as a speaker. I had ZERO idea how it would work out. That risk ended up reframing how I saw my own story, my own journey, my own decisions, and how I’ve grown. 

Gen Z Generations Keynote Speaking

Invite Jason to speak at your in-person or virtual event.

Request Speaking Info