How I Got Started in Title Insurance by Accident

Sometimes the career path you end up loving is not the one you planned at all. In my case, I did not grow up thinking I would end up in title insurance. I was not one of those people who had family in the business, followed in someone’s footsteps, or knew exactly what title or escrow even meant early on.

The running joke in title insurance is that most people either get into it because they were born into it or because they stumble into it by accident. For me, it was definitely the second one.

And honestly, I think that is one of the reasons I still appreciate this business the way I do. I did not enter it with assumptions. I entered it by discovering it in real time, asking questions, learning the industry from the ground up, and figuring out how I could create value in it.

The Year That Changed Everything

Back in 2016, my wife and I made a decision that ended up shaping a lot more than just our travel memories. With nothing but backpacks on our backs, we spent about a year backpacking through Europe and Asia.

It was one of those seasons of life that felt wide open. We wanted adventure, freedom, and experiences. We wanted to see places we had never seen before, meet people from different backgrounds, and take a break from the normal routine of life in the United States.

But beyond the fun and travel, there was another reason for that trip. We hoped it would help us figure out what we wanted the rest of our lives to look like. That was the bigger goal in the background. We thought maybe clarity would show up somewhere on a train ride, in a hostel, on a beach, or while walking through a city halfway across the world.

The funny part is that it did not exactly work out that way. We had an incredible time. We made memories we will never forget. We had conversations about life, goals, priorities, and the future. But by the time we came home, I would not say we had some polished master plan all figured out.

Coming Back to Reality

At some point, every long trip ends and reality starts knocking again. We came back from that adventure and had to start thinking more seriously about what was next.

That transition is something I think a lot of people can relate to. There are seasons in life where things feel open-ended and exciting, and then there comes a point where you need to make the next move. You need to figure out how to turn experience into direction.

I did not come back from that trip saying, “I know exactly what industry I want to be in.” I did not have title insurance on my radar. I was not researching it from hostels in Europe. I was not looking up escrow career paths while traveling through Asia. It simply was not part of the plan because there was no plan for that.

The Random Conversation That Changed Everything

The turning point came in one of the most ordinary and unexpected ways possible. I was at a party in Los Angeles, and we had a family friend there who worked in escrow sales.

She said something simple: “You should sell title insurance.”

My reaction was basically confusion. I remember hearing that and thinking, “Title insurance?”

I literally Googled “what is title insurance.”

That was the beginning.

It is funny how often major life directions start that way. Not with a grand strategy. Not with a 10-year roadmap. Not with some perfect networking event where everything falls into place. Sometimes it starts with one offhand comment from someone in the right place at the right time.

That moment opened a door I had never considered before. One conversation led to one search. One search led to curiosity. Curiosity led to opportunity. And eventually, that led me into the title insurance industry in 2017.

Getting Started in Title Insurance in 2017

Once I got into the business in 2017, I started learning very quickly that title insurance is one of those industries a lot of people do not fully understand until they are in it.

From the outside, many people in real estate know title is important, but they do not always know exactly what the role looks like day to day. They know it is part of the transaction. They know it matters at closing. But the bigger value, the relationships, the education, the problem-solving, and the support behind the scenes are not always obvious until you are in it.

That was true for me too. I started where a lot of people start in any new industry: learning the language, understanding the moving parts, meeting people, asking questions, and figuring out how to create value.

Over time, I realized this business was not just about title insurance itself. It was about helping people. It was about being useful. It was about being a resource to real estate agents, lenders, buyers, sellers, and partners throughout the transaction process.

Why This Industry Ended Up Being a Good Fit

Looking back now, I can see why this industry ended up being such a strong fit for me, even if I did not recognize it at first.

I enjoy relationship-building. I enjoy connecting people. I enjoy helping professionals grow. I enjoy being in rooms where ideas are being shared, businesses are being built, and people are trying to get to the next level.

The title world gave me a lane where I could do all of that. Yes, title insurance is a product and service. Yes, we play a critical role in real estate transactions. But for me, the bigger opportunity was always in being more than just someone tied to a closing.

I wanted to become a resource. I wanted to help agents with marketing. I wanted to help people with strategy. I wanted to create educational opportunities. I wanted to build community.

That is one of the biggest reasons I am still grateful for that random introduction. It led me into an industry where I could take my strengths and apply them in a way that feels meaningful.

What People Outside the Industry Often Miss

One thing I have learned is that title insurance is often misunderstood from the outside.

A lot of people assume the role is narrow. They think it is just paperwork, just closings, or just one step in the process. But once you are in it, you realize there is so much more to it.

There is education. There is communication. There is troubleshooting. There is helping agents stay organized and strategic. There is understanding the market, understanding timelines, and helping transactions move forward smoothly.

There is also a huge relationship component. Real estate is a people business, and title is right in the middle of that. The better you understand people, communication, follow-through, and service, the more valuable you become.

From Accident to Purpose

What started as an accident eventually turned into purpose.

That is one of the biggest lessons I have taken from my own story.

Not every meaningful career starts with certainty. Some start with curiosity. Some start with trial and error. Some start with a random conversation at a party.

And that matters, because a lot of people feel pressure to have everything figured out early. They think they need to know their forever path right away. They think successful people always had a perfectly mapped-out plan from the beginning.

That is just not true.

Sometimes you travel the world and come back with more questions than answers.

Sometimes you hear about an industry you never thought about before.

Sometimes you Google one phrase and end up on a path you never expected.

And sometimes that path ends up being exactly where you were supposed to land.

What This Means for Real Estate Professionals

If you work in real estate, there is a bigger takeaway here too.

A lot of the best opportunities in this industry come through relationships and conversations.

Real estate agents, lenders, title reps, escrow officers, inspectors, photographers, stagers, and marketing partners often end up in the right rooms simply because they kept showing up, kept building relationships, and stayed open to opportunities.

That is why I always value conversations, classes, events, and networking so much. You never know which conversation is going to open the next door. You never know who is going to introduce you to an idea, a strategy, a tool, a referral partner, or even an entirely new direction in your business.

That is one of the reasons I spend so much time creating content, hosting classes, and sharing tools and resources. I know firsthand how much one conversation can change things.

Why I Share Stories Like This

I think there is value in sharing stories that are real, simple, and honest.

Not every piece of content needs to be polished around a perfect success formula. Sometimes people connect more with the truth. They connect with the randomness of life. They connect with the fact that success is often not linear.

My story of getting into title insurance is not some overly strategic origin story. It is just honest. I traveled. I came back. I had a random conversation. I Googled title insurance. Then I started building.

And that was enough.

I think a lot of people need to hear that. You do not need a perfect beginning. You just need a beginning.

Lessons I Took From the Experience

1. Stay open to unexpected opportunities

Some of the best opportunities are not the ones you planned for. They are the ones you almost missed because they came in a form you did not expect.

2. Curiosity matters

I did not know what title insurance was. But instead of dismissing it, I got curious enough to look it up. That small step mattered.

3. One conversation can change your direction

This whole path started with someone making a simple suggestion. That is a reminder to keep having conversations and keep paying attention.

4. You do not need the whole roadmap

A lot of people freeze because they want certainty before they move. My story is proof that sometimes you just need the next step.

5. Build value wherever you land

Once you get into a room or an industry, the question becomes: how do you create value there? That mindset has shaped everything I have tried to build since 2017.

Building a Career Beyond the Job Title

The more time I spent in title insurance, the more I realized I did not want to just be known for the basic job description.

I wanted to build something bigger around education, community, and marketing support for the real estate professionals I work with.

That is what led me to teaching classes, creating video content, sharing tools, hosting events, and trying to be genuinely useful to the people around me.

I think that is one of the best ways to grow in any industry. Do your core job well, but also look for ways to be more helpful, more creative, and more valuable than what people expect.

Final Thoughts

If you had told me while I was backpacking through Europe and Asia in 2016 that I would come back, randomly hear about title insurance at a party in LA, Google what it was, and then build a career around it starting in 2017, I probably would have laughed.

But that is exactly how it happened.

And honestly, I am grateful for it.

I am grateful that a random conversation led me into an industry where I get to work with incredible real estate professionals, be part of important transactions, and help people grow their businesses.

So if your path has felt random, unclear, or unconventional, take that as encouragement. A lot of great careers begin that way.

Stay open. Stay curious. Keep showing up. You never know which conversation is going to change everything. Questions? Contact:

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Jerad Larkin Chicago Title303.630.9430Info@MileHighTitleGuy.com