This past month has taught me a lot about believing in myself and about knowing the difference between a mentor and a mentor in disguise. That mentor in disguise, by the way, should be more aptly named the Gatekeeper. These realizations probably wouldn’t have happened without a little tears and confusion, but here we are.
The first person to underestimate me is me.
I have been doing it my whole life. Beating other people to the punch. Assuming I do not know enough, have not done enough, am not experienced enough, am not the right person to trust on the thing I actually know how to do. I do this so preemptively and so reliably that by the time anyone else gets around to underestimating me, I have already done the work for them.
I had a realization about this in therapy once. My therapist was asking me guiding questions, the kind of questions where she clearly already knew the answer and was waiting for me to figure it out. And I did, mid-question: I underestimate myself first so it hurts less when someone else does it second. If I have already decided I cannot, someone else deciding I cannot does not land the same way. It is a protective reflex. It is also, if we are being honest, another cage.
This self-doubt has been happening most of my life.
I had a photo on a Jones Soda bottle about twenty years ago. I used the photo for an assignment in my photography class once. I was in high school, at an art school, where the whole point was that your teachers were supposed to be helping you get better. Mine told me I would never amount to anything as a photographer with photos like the one I submitted. She was very confident about it. I believed her for a while, because that is what you do when a teacher tells you something in a room where the teacher is supposed to know more than you.
Then I graduated. And at some point after, without much fanfare or belief in myself, I submitted the same photo to Jones Soda. The exact one she had told me was worthless. Jones picked it, and my photo ended up on a bottle that got distributed to grocery stores across the country.
The bottle stays tucked away in the back of my closet. A quiet reminder that I am good enough and that I need to believe in myself. A reminder that there is a version of me who submits the photo anyway. She has always been in there. I just forget about her until I remember.
I did not know how much of my life I had spent inside the cage until this year, on a listing that went sideways.
I was co-brokering with a more experienced agent. The sellers hired her specifically because she was supposed to mentor me through the transaction. That was the deal, spelled out in writing. She would be my mentor. I would be the co-broker. The sellers are my family. They felt more comfortable with her guiding me than with me doing it alone, which I understood and respected.
That almost cost them 10k.
I pulled comps right before we listed. Standard prep. I was not confident in what I found, but not because the market had shifted much. I just was not confident, because I was not confident. I asked her to double check my work, because that is what you do when you are the newer agent and you have a mentor. You ask.
She did not double check my work. She took a section of my text, out of context, and used it to justify a list price well below what the sellers wanted, and the screenshot made it look like I had suggested the low number. I had not. The sellers, seeing what looked like agreement between their two agents, reluctantly said okay. Then she made another push, this time for a number even lower than that, framed as a psychological price point. They agreed again, this time more visibly frustrated than resigned.
Something felt wrong in the way that something feels wrong when your body knows before your brain does, and within a few hours I was not able to sit with it anymore.
Then I did something I would not have done a year ago. It made me uncomfortable to go around my co-broker, the woman who was supposed to be mentoring me. I hate confrontation. I hate when people get upset. As a people pleaser in recovery, I have had to get comfortable with being uncomfortable, because being an effective agent for my sellers sometimes requires making someone else unhappy.
I called the sellers. I explained what had happened. I told them our fiduciary duty is to represent their wishes, not to override them. We are here for guidance and advice, but the decision about how much to sell their home for is theirs. Not ours.
The seller called the other agent. A few minutes later, a text from the other agent came through on our group thread. She had told them we would list at the number they wanted, but with a caveat: we would need to have a conversation about lowering the price when the market did not respond within a month. That was her caveat, not theirs. She had been negative and apprehensive about listing at their number, and she was not being quiet about it. I still think she was trying to force a quick sale, which, ironically, we got anyway.
The first weekend after our listing went live, I hosted the busiest open house of my career. Within two weeks we were pending.
The offer came in at asking.
At. Asking.
I want to be clear about what that moment felt like. It was not vindication in the “look who was wrong” sense. It was quieter and more significant than that. It was the moment I realized I had been right the whole time, that my instincts were not new, that the number I privately thought was correct was, in fact, correct. It was the moment I realized I need to be believing in myself a lot more than I have been.
I had known the whole time, I just did not trust myself enough to know that I knew.
That was the same version of me who submitted the photo to Jones Soda.
Which brings me to the second lesson. Mentor versus gatekeeper.
A mentor is invested in you. They are excited when you win. They stay steady when you lose. They answer your questions and then make sure you understood the answer. They know your success is not a threat to theirs, and they act like there is enough success in the world for everyone.
A gatekeeper opens the same way. They see something in you, they offer to guide you, and they are warm at first. Then, slowly, they position themselves as the reason you are getting anywhere. They keep information close. They take credit that should be shared. They omit your name from the marketing you were supposed to be included on as a co-broker. They add you as a referring agent instead of a co-broker. They negotiate behind your back and act surprised when you notice.
A gatekeeper operates from lack. They believe there is only so much success in the world, and yours will cost them theirs.
The trick is that from the outside, in the early days, a mentor and a gatekeeper look the same. Both are people who know more than you. Both are people offering guidance. The difference only shows up over time, in the pattern of behavior, in who benefits when things go well.
I did not know the difference for a long time because I had never had a real mentor. When I finally did, the pattern became loud. Once you have had someone in your corner who cheers for you even on their bad days, you cannot unsee what it looks like when someone is only cheering when it benefits them.
I am going to keep meeting gatekeepers, and that is not the part I can change. I know what to look for now. Same person, different pantsuit. Real estate is one industry where the pattern shows up loudly, but the pattern is not exclusive to real estate. It is everywhere in sales. It is everywhere in life, honestly. It is anywhere commission structures exist, and anywhere people are being asked to make room for someone newer, and some of them do it well and some of them do it terribly. It shows up wherever anyone is trying to build something that would require another person to open a door.
The part I can change is whether I agree to be gated.
I do not have to shrink to fit the size someone else has decided I am. I do not have to defer to authority when the authority is wrong. I do not have to hand over my instincts because someone with a longer resume told me I was reading the situation incorrectly. I can pull comps and trust them. I can call the sellers. I can submit the photo.
The version of me who submits the photo anyway, who calls when something is not sitting right, is not visiting. She is finally getting some airtime, and I plan on giving her as much space as she needs.
Homebody & Heart 
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