From Teacher to Real Estate Agent

EP 18 Caley Preyss: From Teacher to Real Estate Agent


In this episode of the Teacher Career Coach podcast I’m excited to welcome Caley Preyss, a former-teacher who found success (and personal and professional freedom) in a new career as a real estate agent. Follow along as we talk about everything from soul searching to starting a successful career in real estate. Whether you are interested in pursuing real-estate or not, this is a great episode for anyone looking for inspiration in establishing a healthier work-life balance. 

Listen to the episode in the podcast player below, or find it on Apple Podcast or Spotify.

Recap and BIG Ideas:

  • Keeping your lifestyle goals in mind, determine if the career and lifestyle you are living are sustainable long term.
  • Your career doesn’t define who you are as a person. 
  • Don’t get too caught up in titles. There are ways to continue bringing your love and passion for helping others into a new industry. 
  • Don’t let career stereotypes deter you from trying. You’re likely to have far more transferable skills than you realize
  • You can have more work-life balance (and still go on vacation) with careers outside of the classroom. 
  • There’s going to be different company cultures wherever you go in any industry. It’s about finding the right fit for you. 
  • Learning the real estate industry: licensing, commissions, mentors and getting started in your community. 
  • The best day at a job that makes you miserable is worse than the worst day at a job that you enjoy. 

How the desire for more personal and professional freedom led Caley to leave the classroom. 

Daphne: Hey, Caley, thank you so much for joining us here today. I wanted to start off hearing about your role as a teacher, including your experience and history in education. 

Caley: I wanted to be a teacher for as long as I can remember and was so excited to graduate from college with my degree. I started off substitute teaching for a year before getting what I considered my absolute dream job at the time. I taught first grade at a small private school in downtown Chicago for four years before deciding to leave and look for something else. 

Daphne: What ultimately made you want to start exploring other options?

Caley: There were so many things like I’m sure there are for most people. I absolutely loved teaching while I was doing it. I loved being with the kids and having relationships with them. I loved seeing them change and grow. That’s what kept me in it for as long as it did.

My experiences in my fourth year were kind of the straw that broke the camel’s back. There were so many things, both big and small, that were leading me to feel like I might need to change. 

After I got married I realized how much time I was spending at school and how much of my energy was going into this job, even on the weekends. I didn’t realize that as much when I was single, but after getting married, I realized it was also affecting my husband and I knew we wanted to have a family one day. It wasn’t a lifestyle I wanted to or could sustain long term. 

That was kind of the biggest push for me. There were other things along the way that helped me to get to this realization, but ultimately, I just realized I needed a lifestyle change. 

At the time, I wasn’t sure if I needed a break from teaching altogether or if I just needed a new environment and new school. I ended up leaving in the summer to substitute teach for a few months at a couple of other private schools in the city. 

Eventually, I realized that I did need a lifestyle change because the things that were stressing me out about teaching and just leading me to feel overwhelmed and be physically and mentally unhealthy were going to be the same no matter where I went. They were part of the job and that wasn’t what I wanted long term. 

Taking back the control in your life.

I was in a long-term substitute teaching position in March of 2020 when all the schools shut down and suddenly I had all this time in my hands to reevaluate my future and what I wanted to. I thought, “Do I want to go back when schools open up again? Or do I want to look for something else?”

My dad has been in real estate for 20 years, and I’ve helped him with some administrative work over the years. When I thought about my lifestyle concerns, I looked at his life for the last 20 years. He was able to provide for the family financially and be very much in control of his work schedule. With teaching, I had no control over my life. Sometimes I didn’t even have control over the decisions in my own classroom. 

Looking at the flip side, with a career like real estate you can run your own business, make your own decisions, and be in charge of your scheduling. Of course, you can still burn yourself out by working 24/7, but you are in control. That’s the realization that led me into real estate. 

Daphne: Yeah, so many teachers struggle with those familial relationships.  It’s a theme with so many former-teachers that I’ve interviewed for the podcast.

For me, I felt very much like if I stayed in the environment for another year, my relationship would seriously suffer, and I might not be with my fiance today because I wasn’t able to make any time for him then. 

You were talking a little bit about the autonomy of not feeling like you have control over your own decisions that you’re making inside the classroom. I agree and I really struggled with that. 

Once I had a taste of more autonomy, I knew it was exactly what I needed and wanted, inside or outside of the classroom. I became very clear on what was making me unhappy in non-autonomous positions, including teaching, and was able to figure out what direction I needed to take to find happiness. 

Diving into her skills and passions to find her new path in real estate. 

I’m so excited to talk to you a little bit more about real estate, I know it’s one that many teachers are interested in learning more about. 

Did you struggle with that being the path you chose as your pivot? Or did you know you were going to go from teaching to real estate because you already had that connection with your family? 

Caley: No, I didn’t know I was going to jump into real estate. I talked and prayed about it a lot before making the decision. I really struggled with thinking my career had to be my passion. I thought your career became your identity and had to be what got you to wake up each morning. 

So many teachers do get into the profession for the love of it right for the love of kids and to try and make a difference in their lives. It can be really easy to think that something that you love and you’re passionate about has to be your career. 

So, when I didn’t feel passionate about houses, I had to work through that mindset and realize my career will never make me who I am. I’m an individual person apart from the job that I wake up and do. 

On the other hand, I thought about the skills and passions that made me love teaching and how they could transfer over into so many different careers, including real estate. The skills that helped me excel in teaching would make me a good real estate agent. Exploring those thoughts helped me to make the transition into my new career in real estate. 

I realized there was some overlap with real estate and teaching. Both are people-centric and I’m very relational. It’s one of the things I loved about teaching. Real estate is all about relationships and building connections. 

There’s also an education piece to buying a home, especially for first-time homebuyers. The process can be very overwhelming. So, I’ve actually loved getting to work with first-time homebuyers because I get to pull in that education piece as I make a complex topic more approachable and easier to understand. 

From Teacher to Real Estate Agent

Leveraging your teaching experience in a new position. 

Daphne: Understanding how to balance skills and passions is such a common roadblock for teachers in the process of deciding what their next career move is. We’re intrinsically motivated and just want to continue helping people. We want to find a role that’s basically called “œexecutive helper” or else, we feel like we’re not doing something that’s going to continue to motivate us every day. 

But every former teacher I’ve talked to has found a way to continue to bring their love and passion to their new industry. For example, there’s a software engineer that I interviewed who helps with onboarding new employees through different training and she loves it. 

Even people who have taken my Teacher Career Coach Course have said that even looking at the titles of roles in education companies have them wondering if they’re going to feel that motivation and passion. I remind them that job titles don’t paint the picture of what you can do. The title might not say “executive helper,” but you can still utilize those skills.

Caley: I remember feeling that education is such a specific degree and I didn’t know what else I could do. Before I left, I literally googled “jobs for former teachers.” I felt like there were some skills that would transfer over to another career. 

So, like you said, even if the job title doesn’t necessarily infer that you’re going to be helping or working with people, there are so many jobs out there where your strong teaching skills will easily transfer over. 

Daphne: Actually, there is one role that’s been on my radar since I’ve left education and is called Implementation Specialist or Implementation Manager. Implementation is just another word for teaching. It’s walking someone through whatever the product or whatever the onboarding process is. 

So, people don’t realize there are so many roles out there that are so similar to teaching, just in different industries.It might feel completely different, like real estate, but you’re going to be intrinsically motivated because you are helping first time buyers through a stressful process, or whatever it is. You are going to be able to see their success at the other end, just like you were able to see your students succeed.

I think a lot of times when we see job titles, we naturally feel like we’re not supposed to want those types of positions because they feel like they’re motivated by financial gains, not helping others. But honestly, there’s an empathy piece with basically any position out there. There’s always going to be those personal connections and you’ll always be able to build off of your good heart and bring that to whatever you do. 

Overcoming the stereotypes associated with job titles. 

Caley: Absolutely.  And another thing I wrestled with were the stereotypes we have for certain job titles and what the job entails on a day to day basis. I had this perception of real estate and the sales industry. Now, I don’t have a sales background and I’m not a salesy person. But from talking to other realtors, including my dad, I realized that strengths that made someone a good teacher would also help them become a great anything. It’s okay if you don’t fit a certain stereotype of what you think a certain career is. 

Daphne: I feel like any role with sales brings immediate imposter syndrome to teachers who don’t see themselves as a “salesperson.” So, that’s a role that I always have to explain a little bit more because with sales in an education company, you’re basically explaining to a school district how they could use a product, how it works with their specific demographic, and how teachers would benefit from using said product. 

Yes, there are some skills that are acquired and that can help you be better in that position, but that doesn’t mean you need them to get started and be good in the position. People get nervous when sales is a component, thinning it might change their heart, or it might make them feel bad about their job. At the end of the day, when it comes to ethics, you can be the one deciding how you handle those types of positions. 

Caley: People respond to you being yourself and that will carry over into any kind of position you take on. Especially with any position in sales, people can tell when you are or aren’t being genuine.  Just be yourself. You don’t have to have a stereotypical salesperson personality to go into a role like that. 

In fact, I think the more diversity that there is in those kinds of positions, the more that enriches that environment because people have more choices of who to work with.

Finding a work-life balance outside of the classroom. 

Let’s pivot a little bit and start talking about what your work life balance is like now in your new position. 

My husband has been so happy for me because like I said, our first year of marriage, he lived through my struggles with me and witnessed how much I was getting sick from all of the stress and just how overwhelmed I was. 

And in this past year it’s been a complete 180 in terms of quality of life. That work-life balance that was never there before is finally there and I’m so thankful for that. It has been 1000 times better. 

I love routine and structure and now, with real estate, I’m able to implement that in my daily life. Not every day is the same. For example, some days I’m up and right out the door first thing in the morning for a showing. Other days, I have the morning to myself, and I’m doing showings into the evening. Having that flexibility has allowed me to implement so many healthier routines into my life. I’m physically, mentally, and emotionally healthier than I was a year ago. 

It’s been wonderful having that flexibility and that control over just how much I’m working. With a flexible career like real estate, you still have the potential to burn yourself out working all day and night. But you have the control to choose when to stop working for the day and say, “I’m saving this until the morning when I can get a good night’s rest and start fresh tomorrow.” 

Having the ability to decide my own schedule and to run my own business has been wonderful. 

Daphne: So, one of the things that a lot of people considering leaving teaching struggle with is the idea of losing all that paid vacation time. 

I totally get it, especially if you have children at home over the summer, it would be a financial burden if you ended up having to pay for childcare. 

However, one point a former teacher made is that she’s able to still take paid vacations and, even better, she says she’s able to take paid vacations during times when it’s less expensive or less crowded to do so. When she was teaching, her vacations were spent decompressing from all the stress of her position that she never felt like she really enjoyed it. 

For me, I had maybe two weeks of carefree summer before I decompressed only to then stress out about returning another year to a job that I secretly knew wasn’t a great fit for me.

Dealing with imposter syndrome in the real estate industry. 

One thing that I know a lot of people are probably struggling with when thinking real estate as a potential career path is imposter syndrome and the fear of not being good at it and then not making enough money in commissions to support themselves. 

Caley: It’s a big adjustment from getting that paycheck every two weeks to suddenly being completely commission-based. That was probably one of the biggest adjustments for me. I had to really go out there and work hard and put the time into learning the ropes. 

So, my advice would be choose your brokerage with care. For me, I like how my brokerage offered a lot of flexibility. I can take my meetings from anywhere I can go into our state brokers meetings from anywhere. 

I also chose my brokerage knowing there would be passive income there.  Even if I’m not necessarily hitting all of my sales goals, I am still able to have a source of income and that sense of stability was really important for me. 

Diving into the specifics about making the pivot to the real estate industry. 

Daphne: Okay, so for anybody who’s completely new to this world, brokerage is a term they’re probably a little bit unfamiliar with. What specifically is a brokerage? Is that your managers as the company that you specifically work for? How does that work? 

Caley: Great question. Yes, your brokerage is essentially your company and the company that you work for. It would be the same as teaching at a school and then having someone that you answer to, like the administrator or principal.  In real estate, you have a managing broker, and that is essentially the person that says yes, you can hang your license in this building. They take on some of the liability that comes with practicing real estate. Besides that, you really are your own boss. 

So, you choose your brokerage, which is like your company, and then you submit your license to your designated managing broker. Other than that, you work for yourself and you control your schedule and what your day looks like. Your managing broker is more there for when you have questions about things. 

Of course, every brokerage runs differently. So, if you decide to get into real estate, do your research and learn about the different brokerages that are out there and the different benefits that they offer. It’s not a one size fits all. 

Daphne: There’s going to be different company cultures wherever you go in any industry. It’s about finding the right fit for you. 

Now, if somebody was exploring becoming a real estate agent, what types of certifications would they need? 

Caley: Like with education, you have to take a test based on the state you are working from. Because I made the transition during COVID, I found an online real estate school that I could take at my own pace.

Once you finish your real estate course then you sit for your state test. Once you pass that, then you are a licensed real estate agent, just like with education. Once you pass your licensure exam, you have to choose a brokerage that can claim responsibility of you and allow you to hang your license on their wall. You can’t just do it on your own because you have a license. So, do your research and look into the different brokerages that are out there. Once you choose your brokerage, they will walk you through the next steps. 

My brokerage was extremely helpful with making sure all of my documents were submitted that I’m in compliance with everything. Like with any license, there’s always some legal liability with things like that. I was very thankful that the whole process was extremely smooth and very easy. 

Daphne: Did you feel pressure during the interview process to know everything about everything? Or did you feel very supported during the interview process where they understand a lot of people are coming in as brand new real estate agents? 

Caley: “Interview process” isn’t really the right word to use. It wasn’t an interview in the traditional sense because I wasn’t applying for one specific job role. It was more just than making sure I had my credentials before I could join the brokerage. 

That being said, one of the things I loved about the brokerage that I chose was that it was so easy to be a beginner. I was essentially starting over. Yes, there’s a lot that does transfer over, but you’re also learning a completely new environment and a completely new career. 

You’re starting from square one. You’re learning about this whole new market and what it means to be a real estate agent. The brokerage that I chose actually has classes to help you understand how to run your own business. That was not part of teaching at all, so that was really new to me, as was the financial side of the makerket and some general best practices for being a real estate agent. The brokerage helped me feel confident in being a new real estate agent.

Overcoming the fear of failure when entering a new industry, like real estate. 

Daphne: That makes me really happy because I know there are so many people who probably are listening that are nervous about embarrassing themselves in a new career. Fear of failure is everybody’s biggest fear when it comes to making a change like this. 

Personally, I kind of advocate for failing, because I wouldn’t be where I’m at today if I didn’t put myself in the position to fai. It’s opened up opportunities for me to keep pushing myself to levels that I never thought were possible for me. 

Caley: Yeah, I think some of the best advice that I got from my dad was that it’s okay to admit what you don’t know. Just be yourself and be genuine, because when you’re new, you’re still learning things and you’re not going to have all the answers to the questions that people ask you. It’s okay to say, “I’m not actually completely sure about that, let me look that up and get back to you.”

And just like in teaching, it’s helpful in any career to have a mentor who you can learn from. I worked with my dad, and I would go out to showings with him, I would go to listing appointments with him, I would go sit in his office and just watch how he interacts with clients. So, I recommend finding somebody that’s willing to take you under their wing and show you how it’s done. Learning from somebody who’s an expert at what they do, can be monumental when learning a completely new career. 

Can you enter the career part-time to get your toes wet before fully jumping in? 

Daphne: I know a lot of people are probably thinking this… would there be a potential to even start dipping your toes in this industry on a part time basis if they’re not fully ready to commit to transitioning from teaching into real estate full time? 

Caley: That’s a great question. It’s been a little different during COVID because everyone’s been working from home and showings have been happening all throughout the day. Normally, a lot of times people want to go look at houses are in the evenings and on the weekends. 

So, if you’re not completely sure that you want to make that big jump, you can absolutely get licensed, find a brokerage, and just kind of shadow somebody part time, take a few clients out on the weekends, and dip your toes in. The industry hours very much allow for that. 

As with anything in life, it’s hard to know if something new is a good fit right away. It’s totally okay to take your time figuring that out. Once you make the decision, go for it. 

How making money with commissions works in real estate. 

Daphne: I’m very data driven and am really motivated by numbers. And I know a lot of people over analyze every detail about this process, so could you share more about how commissions work? What do the percentages look like so people can understand how this would translate into their own salary? 

Caley: It depends on if you are the buyer’s agent or the listing agent. As a listing agent, you set your own commission. And again, I’m just speaking for Illinois, so you’d have to look up each state’s rules. But in Illinois, as a listing agent,that percentage of the sale price you get to take as commission is something that you would decide with your client and the seller. In my area, it’s usually somewhere between 5% and 7%. So if it’s a $100,000 house, that means $5,000 to $7,000 in commission. 

And then that is often split between the selling agent and the buyer’s agent. So, if I’m the listing agent, and my client is selling a $100,000 house, I’ve set my commission at 5%. I’m going to take 2.5% and the buyer’s agent will also take 2.5% and we’ll each make $2,500 from the deal. Since I work mostly with buyers right now, I’m not really setting my own commission, but it is roughly around 2.5% on average.  

How to navigate the real estate market as a new agent. 

Daphne: Now, you live in a suburb of Chicago where there are a lot of opportunities. If you lived in a smaller town, though, there’s probably less opportunities. Do you see a lot of remote real estate agents or people who commute into those larger cities for business?

Caley: One of the things I’ve loved about my brokerage is that I’ve connected through social media or through meetings with agents around the country. It’s been interesting to compare the different markets in different communities.

Regardless, one of the strongest tools in your toolbox as a realtor is just being an expert in the area you’re working in. If you live in a really small town, that’s okay. Because you’re probably an expert in that town, especially if you’ve lived there for a number of years. 

At the end of the day, so much of this business is built on trust. And if your clients trust and believe that you know the specific market and you have their best interests at heart, and you’re going to help them to sell their house at the best price or find the house at the best price, then they will want to work with you.  

I can’t really speak to commuting. Maybe there are agents that do that, but I don’t know a whole lot that do that. I moved to where I wanted to do my business, so it was more like a reverse commute. I think most often most realtors would say to work and practice in the community that you are an expert in because you’re selling the community, as well as the houses.  

Daphne: And it can help you build your network. You can leverage your own network, even in a smaller community. Honestly, that might even be useful when you’re just getting started and are figuring out your next steps. 

Caley’s advice for teachers on the brink of pivoting careers. 

Daphne: I wanted to hear if you had any advice for any of the teachers right now who are listening. They’re excited about this possibility, but they’re still one one step away from believing that this is a real possibility from them. What kind of encouragement would you give them? 

Caley: I wish that when I was in that position a couple of years ago, I wish that there were resources like yours, like your blog. I wish I’d known I wasn’t alone and that there are other teachers feeling the same way. There are teachers that are feeling like, “Gosh, I don’t know if this is for me anymore, even though I’ve loved it,” and that’s okay. It’s okay to love something and also know that it’s time for a new season. 

You have to follow that. Fear can really cripple us, but we have to be wise and discerning. So, talk to your friends and family that know you really well and bounce things off of them. For me, praying was a huge part of that decision. 

At the end of the day, just go for it and just realize that the worst that can happen is you decide, okay, this isn’t for me either. And then you cross that one off the list and move on to the next. It’s okay to exhaust a few options, before you find something that’s a really good fit. 

Daphne: That’s such great advice. The fear of not finding the right fit on that second try holds a lot of people back. It’s that idea that I put 10 years into my educational profession so I was devastated when I realized it wasn’t right for me. What if the next one’s worse, right?  But if you are absolutely miserable, the best day at a miserable job is worse than the worst day at a job that you enjoy. 

Remember this, you get better at adapting to changes the more you put yourself in these positions. You also don’t have the pressure of a teaching contract that makes it hard for you to find the next position, right? Because you’ve already crossed that bridge of leaving a contract that feels very restrictive. 

Caley: I’ve actually said that exact same thing that you just said. Even on the hardest days in real estate, where I’m just running around like crazy and I’m exhausted, I still know this was the right decision for me. 

Daphne: Not everyone is going to feel that extreme, and that’s good. I don’t want everyone to be miserable. I want people to be able to recognize they’re in a position and actually feel happy 80% of the time, despite the quirks. I want them to realize they might need to make some adjustments to avoid burnout. 

But, if the idea of staying in your current position for 5 or 10 more years makes you feel sick to your stomach, that’s a huge indicator you should consider other options.

Caley: I felt that way too. The positive things, like working with the little kids, can keep you going for a while. It’s when you realize the negatives outweigh the positives that it’s time for a change.

Daphne: Or when you find yourself being turned into a negative person. I can tell just by meeting you today, that you are a lovely person who does not have a dark cloud above her. So I’m very, very happy that you found something that brings you joy and continues to fulfill you. I’m just so happy for you that you’ve found this position and that it’s working out well for you. 

Caley: Well, thank you so much. That means a lot to me. I’m very, very thankful.


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Where to start

If you’re just beginning to think about leaving teaching, brainstorming other options is a great place to start. But if you’re like many others, teaching was your only plan – there never was a Plan B. You might feel at a loss when it comes to figuring out what alternatives are out there.

Start with our free quiz, below, to get alternative job options for careers that really do hire teachers!

What career outside the classroom is right for YOU? Free Quiz

Taking the First Steps to a New Career

If you’ve already taken our quiz, it may be time for the next steps. I want to help you get some clarity in the options available to you. To know EXACTLY what you need to do (and not do) in order to get your foot in the door.

One of the biggest mistakes that I see teachers make is that they try to navigate this process alone. Often, they put off “researching” until the very last minute. Which sets them up for a very stressful application season – trying to juggle teaching, figuring out a resume, researching jobs, and hoping to nail down some interviews before signing next year’s contract.

You don’t have to do this on your own.

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Career Transition Guide
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