How I Accidentally Built a Career in Title Insurance
How did I go from backpacking through Europe and Asia to becoming a title insurance representative with Chicago Title in Colorado?
I did not grow up dreaming about working in title insurance. I stumbled into the industry after returning home from a year of traveling, spending nearly all my money, and realizing I needed to find a real job. What started as an unexpected career move eventually became an opportunity to build relationships, support real estate professionals, and help agents grow their businesses.
Nobody Grows Up Wanting to Be a Title Rep
Nobody grows up saying, “I want to be a title rep.”
At least I didn’t.
When you ask children what they want to be when they grow up, you hear answers like a firefighter, professional athlete, doctor, teacher, pilot, or maybe an entrepreneur. I do not think many people have ever heard a child confidently announce that they want to work in title insurance.
The truth is that many people working in the title industry did not originally plan to be here. They discovered the business through a family member, friend, job opportunity, real estate connection, or completely unexpected series of events.
That was certainly true for me.
My path to becoming a title insurance representative was not carefully planned. I did not study title insurance in school, map out a ten-year career strategy, or spend my early twenties preparing to become the Mile High Title Guy.
Before I joined Chicago Title, I was much more interested in seeing the world.
The Adventure Before My Real Estate Career
Before entering the title industry, my wife and I spent about a year backpacking through Europe and Asia.
It was an incredible experience. We traveled to new places, learned about different cultures, met interesting people, and collected the kinds of memories that stay with you for the rest of your life.
Travel has a way of changing your perspective. It forces you to become more adaptable, solve problems quickly, communicate with people from different backgrounds, and become comfortable with uncertainty.
You learn how to navigate unfamiliar cities, adjust when plans fall apart, and figure things out as you go. You also learn that some of the best experiences happen when your original plan changes.
At the time, however, I was not thinking about how any of those lessons might eventually help me in sales or real estate. I was simply enjoying the experience and trying to make the most of the opportunity.
We traveled for about a year and spent just about every dollar we had.
Eventually, reality caught up with us.
Coming Home and Starting Over
When my wife and I returned home, we were living in our parents’ basement.
I had experienced an incredible year of traveling, but I did not have a clear career waiting for me. I was also in a little bit of denial about the fact that I needed to find a real job.
After spending so much time traveling and experiencing new places, returning to reality was an adjustment. I had to figure out what came next.
I did not have the perfect plan.
I did not have a carefully designed career path.
I just knew I needed to start moving forward.
Looking back, I think this is a place many people experience at some point in their lives. You may have an idea of where you want to go, but the next step is not always obvious. Sometimes you have to take an opportunity, learn as you go, and allow the path to become clearer over time.
That is ultimately how I found the title industry.
Stumbling Into the Title Insurance Industry
I stumbled into title insurance.
There was no childhood dream or dramatic moment when I realized title was my calling. It was simply an opportunity that appeared when I needed one.
At first, I had to learn what title insurance was, why it mattered, and how the title company fit into a real estate transaction.
For people outside the real estate industry, title insurance can feel invisible. Buyers and sellers may see the title company on an email, receive documents before closing, and show up to sign paperwork without fully understanding everything happening behind the scenes.
A title company helps research the history of a property, identify potential ownership or lien issues, coordinate important parts of the transaction, facilitate closing, and issue title insurance policies that help protect against certain covered risks.
There is a tremendous amount of detail involved. Real estate transactions include deadlines, legal documents, financial interests, ownership records, communication among multiple parties, and unexpected challenges.
I quickly learned that title insurance is not just another box to check during a transaction. It is an important part of helping buyers, sellers, real estate agents, lenders, and other professionals move toward a successful closing.
I also discovered that my role could be much bigger than simply asking agents to send their title orders to Chicago Title.
Finding the Part of the Career That Fit Me
The title industry gave me an opportunity to combine several things I genuinely enjoy:
Building relationships
Connecting people
Teaching and sharing information
Exploring new technology
Developing marketing strategies
Hosting classes and community events
Helping real estate professionals solve problems
Creating resources that save people time
That combination is what eventually made this career feel like the right fit.
I am an account executive with Chicago Title, but I have never wanted my value to begin and end with a request for title business.
My goal is to become a genuine resource for real estate professionals.
I want agents to know they can contact me when they need help with a title question, but I also want them to think of me when they are looking for a new marketing strategy, technology tool, educational opportunity, industry connection, or idea for growing their business.
That is the part of the career I did not see coming.
I may have accidentally entered the title industry, but I became intentional about how I wanted to serve the people within it.
Becoming More Than a Traditional Title Rep
Real estate agents receive a lot of sales calls.
They hear from title representatives, lenders, insurance agents, photographers, transaction coordinators, home warranty companies, inspectors, marketers, and countless technology providers.
Everyone wants a few minutes of their time. Everyone claims to offer great service.
I realized that if I wanted to build meaningful relationships with agents, I needed to provide meaningful value.
Good service is essential, but saying that you provide good service is not enough. You have to demonstrate how you can make someone’s business or transaction better.
That shifted the way I approached my role.
Instead of focusing only on what I wanted from an agent, I started thinking more carefully about what agents actually needed.
Real estate professionals are often trying to balance:
Lead generation
Client communication
Listing preparation
Buyer consultations
Contract deadlines
Social media
Video marketing
Database follow-up
Market research
Technology
Continuing education
Transaction management
Many agents are also running their businesses almost entirely by themselves.
They do not necessarily need another salesperson asking for something. They need trusted partners who can help them work through challenges, find useful resources, and create new opportunities.
That is where I saw an opportunity to build a different kind of title insurance sales career.
Helping Real Estate Agents Grow Their Businesses
Today, a large part of what I do involves helping real estate agents grow.
That may include teaching a class about artificial intelligence, sharing a social media strategy, explaining a title issue, helping an agent think through a marketing campaign, or connecting two people who could benefit from knowing each other.
I spend a lot of time testing tools and strategies before recommending them.
Technology changes quickly, especially with the rapid growth of artificial intelligence. There is always another platform, feature, automation, or marketing system promising to transform a real estate business.
I do not believe agents need to use every new tool.
I do believe they benefit from having someone willing to test those tools, understand the practical use cases, and explain what may actually be worth their time.
For example, I explore ways real estate professionals can use AI to:
Create and repurpose marketing content
Analyze MLS data
Develop market reports
Organize contact information
Prepare educational materials
Build landing pages
Improve follow-up systems
Automate repetitive administrative tasks
Turn video transcripts into blogs, emails, and social posts
The goal is not to remove the personal side of real estate. Relationships, judgment, local knowledge, and trust remain incredibly important.
The goal is to help agents spend less time on repetitive work so they have more time for their clients and relationships.
Building Community in Colorado Real Estate
Another part of my career that I value is the opportunity to bring people together.
Real estate can be a lonely business.
Agents may work independently, spend much of the day driving between appointments, and carry the pressure of generating their own business. Even agents who work within a brokerage can sometimes feel like they are building everything on their own.
That is one reason I enjoy hosting classes, workshops, panels, networking opportunities, and community events.
These events are not only about learning a new strategy. They give real estate professionals a chance to meet other people who understand the challenges of the business.
Someone might attend a class to learn about AI or marketing and leave with a new referral partner, collaborator, vendor relationship, or friend.
That sense of community matters to me.
My work with Chicago Title allows me to support agents throughout Denver and across Colorado, but it also gives me a platform to create spaces where people can exchange ideas and help one another succeed.
What Travel Taught Me About Relationship Building
Although backpacking did not directly prepare me to explain title commitments or help coordinate a real estate closing, the experience taught me lessons I still use today.
Travel taught me how to connect with different personalities.
It taught me to listen.
It taught me to stay flexible when circumstances change.
It taught me that relationships can form quickly when you are curious, open, and willing to have a genuine conversation.
Those lessons apply directly to real estate.
Every agent builds a business differently. Some agents love video and social media. Others prefer networking, referrals, open houses, geographic farming, community involvement, or direct outreach.
My job is not to force every agent into the same strategy. My job is to understand what they are trying to accomplish and help them find an approach that works for their business and personality.
That same flexibility is important during a real estate transaction. Unexpected issues can arise. Communication matters. People want to know that their partners are paying attention and working toward a solution.
The ability to remain calm, communicate clearly, and adapt to changing circumstances has served me well throughout my career.
The Career You Never Planned May Fit You Best
I think there is an important lesson in career paths that do not follow a straight line.
We often assume we are supposed to know exactly what we want to do. We feel pressure to create the perfect plan, make the correct decision, and predict where every opportunity will lead.
Real life rarely works that way.
Sometimes the career you never planned becomes the one that fits you best.
You may enter an industry because you need a job, meet someone who opens an unexpected door, or accept an opportunity you initially view as temporary.
What matters is what you do after you arrive.
Do you stay curious?
Do you continue learning?
Do you look for ways to use your strengths?
Do you find opportunities to help other people?
Do you make the role your own?
I did not choose title insurance because I had a lifelong passion for property records. I stayed and grew because I discovered that the industry allowed me to work with great people, build a community, create valuable resources, and help real estate professionals succeed.
Over time, I developed a career that aligned with my personality and interests.
My Approach as the Mile High Title Guy
The Mile High Title Guy brand grew out of a simple idea: I wanted to be more than a name and phone number on a title company flyer.
I wanted to create a recognizable resource for Colorado real estate professionals.
Through MileHighTitleGuy.com, my classes, social media content, videos, emails, and events, I share ideas agents can put into action.
Some of those ideas relate directly to title insurance. Others focus on marketing, technology, branding, video, AI, lead generation, or business development.
All of them connect to the same purpose: helping real estate professionals save time, build stronger businesses, and better serve their clients.
I also want agents to feel comfortable reaching out when they have questions.
You do not need to wait until you have a transaction ready to close. If you are trying to understand a title issue, find a marketing resource, learn a new tool, or connect with someone in the Denver real estate community, I want to be someone you can call.
That is the kind of relationship I want to build.
Why I Am Grateful the Original Plan Changed
If you had told me while I was backpacking through Europe and Asia that I would eventually build a career as a title insurance representative in Colorado, I probably would not have believed you.
At that point, I was focused on seeing the world and making the adventure last as long as possible.
Eventually, the money ran out. We came home. I moved into my parents’ basement and had to figure out what to do next.
That moment did not feel like the beginning of a meaningful career, but that is exactly what it became.
Today, I get to work with real estate professionals throughout Denver and Colorado. I get to build relationships, teach classes, experiment with new technology, organize events, share marketing ideas, and help agents grow their businesses.
I also get to work alongside a team at Chicago Title that helps buyers, sellers, agents, and lenders navigate one of the most important transactions in people’s lives.
It was definitely not my original plan.
I am grateful it worked out this way.
Final Takeaway
A career does not always begin with a perfect plan. Sometimes it begins when you return home, run out of money, move into your parents’ basement, and finally admit that you need to find a job.
The opportunity may be unexpected, but what you build from it is up to you.
I stumbled into title insurance, but I found a career that allows me to build relationships, support the Colorado real estate community, and help agents become more effective in their businesses.
If you are a real estate professional, I would love to be a resource for you, whether you need support on a title transaction, a marketing idea, an educational opportunity, or a connection within the industry.
Want more real estate tools, resources, and marketing ideas? Subscribe at MileHighTitleGuy.com/subscribe for exclusive access and invitations to upcoming classes and events in Colorado.
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