From the military to tech, sales to social media, and now teaching, my career path has been anything but conventional. Along the way, I’ve learned invaluable lessons that have shaped my ability to reinvent myself time and time again. Here are 10 key lessons I’ve learned throughout my journey—from Navy cryptologist to sales leader to educator—and how each experience contributed to my ongoing reinvention.
Lesson 1: Sometimes the Most Unlikely Beginnings Lead to the Most Rewarding Careers
I started my career in the Navy in 1992, where my job as a cryptologist and delivering messages by hand might not have seemed like the perfect foundation for the corporate world. But it taught me how to handle responsibility, work under pressure, and solve problems—all skills that would serve me throughout my career. From living on a Coast Guard base in the San Francisco Bay area to spending a year in Korea teaching English to a young Korean boy, I learned early on that diverse experiences can provide the foundation for something much bigger.
The lesson here? Don’t underestimate the value of seemingly unrelated experiences. Every chapter adds a layer to your skills, resilience, and perspective, even if it doesn’t immediately seem relevant to where you want to go.
Lesson 2: Be Open to Opportunities and Embrace the Learning Process
After moving to Milwaukee in 1996, I started college to become a teacher, but I didn’t stop there. I also delivered pizzas and became a peer trainer teaching faculty and students about new technology. Those experiences taught me that no matter your role, you can always learn and grow.
What I realized is that even early in your career, the opportunities you take can be just as valuable as the degree or job you’re aiming for. The key is to be open, ask questions, and be curious about everything around you.
Lesson 3: Don't Be Afraid to Take Risks—Even When It Means Leaving College
In 1998, I made a bold decision. I dropped out of college to pursue a “real job” in tech support, which eventually led to my first sales job selling high-speed internet. At the time, the internet wasn’t nearly as fast as we now think of it, and there was a lot of skepticism around the promises we made to customers. But I learned that taking risks and stepping outside my comfort zone would be necessary to continue growing.
The lesson here? Calculated risk-taking is vital to career growth. Sometimes, leaving the traditional path can open doors to opportunities that might not be on your radar otherwise.
Lesson 4: Show Up and Be Ready to Learn—Even When It’s Hard
By 2000, I had transitioned into a stockbroker role and was working on a trading team. I was also responsible for teaching others how to use our online trading platform. After 9/11, I realized that technology was my true calling, so I transitioned into IT. Within two years, I earned my first management role, and eventually worked my way up to a VP of IT position.
The key takeaway? Show up fully, be ready to learn, and always look for ways to add value. This is how you rise through the ranks and start shaping your own career trajectory.
Lesson 5: Leadership is About Stepping Up—Even When You’re Not Fully Ready
In 2003, I finished my degree in computer science and took on a leadership role. About a year later, my manager decided to leave, and I was given the opportunity to lead the team. Even though I wasn’t entirely prepared, I stepped up and said yes. That decision was pivotal in my career. It taught me that leadership often comes when you least expect it—and when it does, you need to be willing to take that leap of faith.
Sometimes, leadership isn’t about having all the answers; it’s about being willing to step up and figure it out.
Lesson 6: Your Experience and Knowledge Are Valuable—Don’t Be Afraid to Share Them
In 2005, I started my blog, sharing lessons I had learned along the way. I was reading books and consuming other blogs, and I wanted to contribute to the broader conversation. It was a humbling experience, but it also taught me that sharing your expertise—even when you're not a household name yet—can make a huge impact.
In 2007, I joined David Zinger to write the Slacker Manager blog, co-authoring content on employee engagement and leadership. This experience taught me the power of collaboration and how sharing knowledge publicly can boost your credibility and open doors.
Lesson 7: Self-Belief Is the First Step to Reinvention—Everything Else Follows
In 2010, I decided to leave my corporate job, something I had been contemplating for years. People doubted I was really going to leave, and many thought I would fail. But I printed business cards, started networking as a consultant, and landed several consulting gigs with small businesses.
The key lesson? Self-belief is the foundation of reinvention. When you believe in your ability to solve problems and create value, you can step into new opportunities, even if others doubt you or question your decisions. Your belief in yourself is what will propel you forward.
Lesson 8: Clarity of Offer is Key to Digital Leadership and Sales Success
In 2013, I worked for a Silicon Valley software company and led the social media strategy. We made three major changes to our product’s strategy within 18 months, and as a result, our product didn’t sell well. Meanwhile, a more established product with a clear, defined space in the market continued to do well.
This taught me that clarity is essential. If your audience doesn’t understand what you’re offering or why they need it, they won’t buy. A clear, consistent message is key to success in sales and leadership.
Lesson 9: Tenacity and Simplicity Are Keys to Teaching the Unbelievable
In 2015, I returned to the world of speaking and training, teaching salespeople how to leverage social media. At the time, many people were skeptical about social media as a business tool, and it was up to me to show them its value. I had to simplify complex ideas and be persistent in explaining them until others understood.
This experience reinforced the lesson that teaching something new or controversial takes tenacity, courage, and the ability to break down complex ideas into simple, actionable steps. Persistence pays off when you're teaching others to see what they can’t yet fully grasp.
Lesson 10: Flexibility and Hustle Are Essential for Navigating Life’s Unexpected Turns
In 2022, I joined Bamboo HR in Sales Enablement, but by mid-2023, we moved to Ohio, and I had to give up that role. I pivoted again, working as a substitute teacher while I looked for a full-time position in education.
What this taught me was that you have to be flexible when life throws curveballs, and you have to be willing to do whatever it takes to stay true to your goals. Whether it’s working a second job to keep things afloat or stepping into a completely different field, staying adaptable and persistent is key to navigating life’s unexpected changes.
Throughout my career, these 10 lessons have been my guiding principles. From learning to step up as a leader before I felt ready, to teaching and simplifying complex ideas, to staying adaptable and flexible, each lesson has helped me reinvent myself at different stages of my career.
The road to reinvention is rarely straight, but if you’re willing to embrace these lessons and keep moving forward, you can build a career that’s uniquely yours, no matter where you start or where life takes you next.
Share this post