Ep. 125: 3 Milestones That Rewrote My Life

In this heartfelt episode, I reflect on three significant anniversaries in my life: the 30th anniversary of my insurance agency, the 2nd anniversary of my 'Maybe I Can' podcast, and what would have been my 31st wedding anniversary with Gary. I share the struggles and self-doubt I faced when starting my podcast and how I overcame them with persistence and coaching. I recount the tough early days of my insurance agency, highlighting the perseverance it took to succeed and the personal growth I experienced. Lastly, I reminisce about meeting Gary, our whirlwind romance, and the beautiful life we built together. Join me as I share these intimate milestones and the invaluable lessons I've learned along the way.

TIMESTAMPS:

00:00 Celebrating Milestones: Podcast and Wedding Anniversaries

01:08 Starting the Podcast: Overcoming Self-Doubt

04:22 Reflecting on Two Years of Podcasting

06:16 30 Years in Insurance: A Journey of Perseverance

08:37 The Early Struggles: Building the Insurance Agency

13:41 Personal Growth and Professional Success

17:12 Remembering Gary: A Love Story

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Chapters

• 0:00 Celebrating Podcast's Second Anniversary
• 6:13 The Self-Doubt and Comparison Trap
• 12:58 Thirty Years as an Insurance Agent
• 14:40 Starting from Scratch: Early Agency Struggles
• 17:12 Perseverance Through Overwhelming Obstacles
• 22:03 Reflecting on My 31-Year Marriage
• 26:01 Moving Forward After Loss

Transcript

Speaker 1: 0:00

Hi and welcome back to the Maybe I Can podcast. I'm your host, debbie Weiss, and thanks so much for joining me today. Today for me is a special episode, and so I hope that you will glean something from it as well. It is May, the beginning of May as I'm recording this, and for me, I have three pretty much concurrent anniversaries happening at the same time. So May 1st was 30 years since I opened my insurance agency. I am actually I should have looked it up before I pressed record but I'm not sure if it was May 1st or May 8th that I chose to start the podcast, but let's just say that it was two years ago now. So I'm celebrating my second anniversary with the Maybe I Can podcast, and May 8th would have been my 31st wedding anniversary. So let's start with the podcast, the most recent thing, and I want to give you a little bit of history and why I'm super proud that I've made it here for two years.

Speaker 1: 1:22

When I started, I really was very apprehensive. I didn't know how I would do it. I didn't know if anyone would listen, if I had anything of value to share. I had a lot of self-doubt and it just seemed overwhelming. And at the time Shana, my business coach, really pushed me and she said you are a natural to be a podcaster, I think, because talking, or rambling, as my family would say, is my superpower. And she was right. But in the beginning I had so much self-doubt and I was doing too much comparing myself to others, right? So I would listen to other podcasts and kind of forget that maybe they'd been doing it for four or five, 10 years and that looks a lot different than a beginner. A beginner, they have the really nice oh gosh, you know intro music and the intro, you know that they say, and the outro, and they just sound so clean and polished and just like the words are just flowing out of them so easily, without any hesitation. And then I look at myself and think, oh gosh, I lose track of and I have these big breaks and I ramble and I tried to have music, but then that's a pain to edit because I don't have this big professional team behind me. And what am I even doing this for team behind me? And what am I even doing this for? And it's just like anything when you do that whole comparison thing, whether it's for your podcast, for your business, for your relationship, for your social life. You know, we all know, what it's like when we look at everybody else's what seems to be perfect lives and ours don't, you know, hold up. But you know, we all know nobody's life is perfect.

Speaker 1: 3:30

And I think with the podcast I am trying to compare myself as a beginner which I still feel like I'm relatively a beginner to someone who is more seasoned, who has the money. You know those podcasts that have ads. They have ads because they've been able to create an audience and have that professional feel to it. That doesn't happen overnight, sure, to big name people. When Oprah started her podcast, yeah, she didn't need to learn, she already knew. You know other name, brand, quote unquote people, celebrities they start their podcast. You know they're already a household name. It's very different for someone like myself you know an unknown to be able to do it.

Speaker 1: 4:22

And many times in this past two years I felt like giving up. I felt like what I said really doesn't add value. Not enough people are listening. It's hard. It's hard to come up with something that I feel would be helpful to you guys every time that I hit record. And it's another quote-unquote job. Right, it's something else that I need to concentrate on during the week in you know my list of what feels like endless responsibilities. And boy, I mean just about two months ago. And boy, I mean just about two months ago. I was going to quit.

Speaker 1: 5:12

When I left Transformation Talk Radio in April, I thought, okay, this is just the perfect ending. But there was something inside of me that's it was nagging and I listened because that nag, you know, is that little voice inside that said it knows, it knows that I want to and I need to continue, and as I continue I'll get better. Right, I'm better than I was two years ago, and two years from now I'll be better than I am today. And it's a journey and my only hope is that, you know, each episode you get a little something from it or I make you think a little bit differently about something. So I am super grateful to be celebrating my two-year anniversary. I appreciate you listening more than words can say. So, okay, that's anniversary number one. Let's go to anniversary number two my insurance agency.

Speaker 1: 6:18

As I said, 30 years. And I got to take you back to the beginning because it's so hard for me to believe that it is 30 years, because when I started, oh boy, I didn't think it was going to last 30 days, let alone 30 years, and it took so much perseverance and grit and struggle and all of the things. And you know again, if someone looks today and says, wow, look at what she has. She has this great team, she has these wonderful customers and clients and I have freedom and I have a decent income and just all the things. But yet let me just take you back 30 years ago. I was given this opportunity, which was amazing, but I had to give up security. I was a CPA and I had been working at the same firm for 10 years and I could still be there today if I continued to work and didn't leave. I had to move.

Speaker 1: 7:38

I grown up on Long Island, you know, I think I was well, I guess not. I think it was 30 years ago. So that meant that I was almost 32 when I made the decision and I shouldn't say I, because it was we, it was Gary and I, it was my husband and I. He had the sales background. I had been a CPA, but he had always been a salesman. Even though it had nothing to do with insurance and neither one of us knew the first thing about insurance, he at least had sold building supplies, plywood, all different things, and he was, you know, a very successful salesman. He had the gift. He had the gift of Gabby. He could talk to anyone he could, I don't know. He was very comfortable in his own skin and I wasn't. And so, anyway, we moved from Long Island to New Jersey.

Speaker 1: 8:37

The first year and a half we actually lived in my friend's basement because we did not have the money. We had never worked together before. We did not really have any training on what we were supposed to do day to day in the insurance agency. We had training over certain products, mostly life insurance products, and so we knew that, but yet there was no training on what we were supposed to be doing 99% of the time. And when we opened, we were actually given clients from a retired agent that they reassigned to me, a retired agent that they reassigned to me. Problem was is that the clients that were reassigned had no idea it was going to happen, and the agent that retired, his son also opened the agency. And Yogi, what are you barking about? Stop and long story. It doesn't matter how it all works, but those clients felt like I stole them from the son, even though that's not what happened.

Speaker 1: 9:51

And so we were living in a basement apartment, not apartment, a base with a bed shoved in it. We were commuting about an hour each way. We would get there. We didn't know what we were doing. People would come in and say I got a new car and we'd be like that's nice. We didn't know what we were supposed to do, the questions we were supposed to ask, what we were supposed to do on the computer, what forms they were supposed to sign, like the whole thing. And then, when that wasn't happening, people were calling and screaming at me saying who the heck are you and why did you steal my business? And I want to go back to the sun. And so in the first three weeks I probably lost 500 customers.

Speaker 1: 10:42

And while this was happening, let me just say that the company we were kind of like in a probationary period for the first two years, and so each month we had sales quotas that we had to hit and who was I selling to? People were screaming at me, they were leaving. I didn't even know how to talk to people about, you know, getting a new car, which obviously in the insurance industry happens, you know, a million times every day. It's bread and butter kind of thing. We weren't actually getting paid, even though I was making money. We were only getting paid half of what the normal agent would get, because we were on probation, but yet we still had to pay for the staff that I had, which was, I think, only one person at the time, and that one person didn't know what she was doing either. She was looking for, you know, to us to train her, but we didn't know what we were doing. So we were all learning together and I had to pay the rent and you know the utilities, you know all the things by the supplies, all of that kind of stuff. So we never had money. People were screaming at us. I was going to be fired if I didn't make the quotas. My husband and I had never worked together. Neither one of us knew what we were doing. We were together 24-7, living in this little basement.

Speaker 1: 12:05

It was horrible. It was horrible. Every day I was crying Every day. Every day I wanted to retreat. I wanted to turn around, put my tail between my legs. Put my tail between my legs, run back to Long Island, go back, get my accounting job. But I didn't do it. I would like to think it was all me, but I know that it wasn't. My friend had given me this opportunity, so I took it very seriously and I know that she would have felt she would have she stuck her neck out right and if I was not successful it would not be a good reflection for her. So that was the main thing that I said. I got to get through this.

Speaker 1: 12:54

And then there was Gary who was, you know, trying to build me up and he just had a better attitude about it because I was so stressed about every little thing. I can't stand someone asking me a question and I'm not confident in the answer. I don't like that. Where he could I don't want to say BS the answer, but he could. And then you know he had no problem saying making it feel like he was confident, he knew what he was doing, but maybe making it sound like oh gee, that's a really good question. I have to get back to you. And then we would kind of like recoup in the back, regroup and kind of be like where do we find the answer to this and figure all of that out. We made it. We made it through the two years. I don't know how. In there.

Speaker 1: 13:46

My father also went into congestive heart failure. He was still living in Long Island because I hadn't yet been able, with the move and everything that was going on, I hadn't yet been able to find him a place in New Jersey because there weren't that many places to be found. And so in the first couple of months of me becoming an agent he went into congestive heart failure. Nobody else was in Long Island, you know, it's only my brother and I, and my brother at that time was living in Kansas City, so I was the closest, so I was the closest, and so for a week in, I started it May 1st and in June he needed triple bypass, which was not the quote unquote, you know standard procedure that it is today. It was a major deal. He was in the hospital for at least 10 days. It was a whole thing and I had a leaf.

Speaker 1: 14:39

So I had so much stress, so much adversity and somehow I made it through. And it was. You know I hate to single something out, so I'll just say it is the top in the top, top five things that changed my life. It changed my life for the better. It gave me so much, so much freedom, freedom to be there for my dad, for my kids, to actually have my kids to go through all the infertility treatment that was necessary, to be there for Gary through his illness, you know, through his last six months of his life today to give me the freedom to still be here for my son and to be here talking to you. It's been amazing. It's been amazing but, man, it was one of the toughest periods of my life.

Speaker 1: 15:51

Those first two years, completely a different person, completely confident, even if I don't know the answer. When someone asks me a question, which happens, I don't know every answer. There's a lot to know. I have no problem, you know, telling them hey, you know, I'm not sure, let me check it out and get back to you. Today I have, you know, I'm a different boss. I have learned how to manage people better than I did 30 years ago. You know, I was afraid to have the hard conversations with people. I oh just so much. I've grown right. Isn't that what happens to all of us? Isn't that what happens to all of us? This is a perfect example of stepping completely out of my comfort zone in every which way, and now, 30 years later, I'm telling you that it was a pivotal time in my life, which is just a reminder that this is what we need to do. We need to continually face our fear and step out of our comfort zone, because when we do, it can literally change our lives. Okay, third anniversary Coming up. I'm recording this actually on the 6th. It's hopefully coming out on the 7th. On May 8th it would have been my 31st wedding anniversary. Yep, Got a little emotional behind that.

Speaker 1: 17:35

I think back to when I met Gary and I met him. I was, as I said, I was a CPA. I would travel monthly to my different accounting clients. He worked at one of those places. It was a plywood company. I had nothing to do with him. He was an inside salesman and it was really the controller there kind of hooked us up and I would go in every time and he and I would chat and we'd have these wonderful conversations. He would never ask me out and then I kept making excuses to go back there and I couldn't understand and I really like pursued him. I played a lot of little games, stopping in at the company other times than my scheduled visit, making up an excuse why I was there. I would show up like close to five o'clock so that I would start talking to him at like five to five and then it would be time to leave and we would go out into the parking lot and we'd continue to talk.

Speaker 1: 18:41

And our first date was actually meeting at a driving range because he was a golfer and just coincidentally, my mom and I had started taking lessons, I don't know months or so beforehand. So we met at a driving range and that was all fine and went well. And then when we were in the parking lot after we were done hitting, we're talking, we're talking, we're talking Like we're standing there talking in the parking lot. I don't know, it could have been an hour and he never said want to go to the diner and get something to eat? You know, wanna, I don't know whatever. He nothing. He said nothing Until finally I was like okay, what do I? I said so, what are you doing now? Because it was like a Saturday afternoon, maybe it was like four o'clock. He said nothing. What about? What about you? I said well, actually I'm going to my mother's. She's right down the road. I'm going over there for dinner. Do you want to come? Never thinking, he says yes. But he said yes. I mean, who says yes, he doesn't even know me.

Speaker 1: 19:58

And our first date was literally then going over to my mother's house. My mother and Joe, my stepfather, were there very surprised, you know, they knew that I was meeting him, so very surprised when I walked in with him and we wind up like sitting outside playing cards, having dinner and you know, it just felt right I don't know how else to explain. It just felt so easy, so comfortable and I think I just knew right then this is the person that I'm supposed to be with Soon, after I mean our relationship and I was 29, he was 35. And you know he at that point had kind of resigned himself that he was good being by himself and he didn't want to complicate his life. He liked his life very simple the way it was. He didn't want to complicate his life. And so even after we had a good time, it took, you know, I had to really pursue him more and it took about another month of this hot pursuit until he finally gave up and said, okay, I'm all in. And we quickly from there.

Speaker 1: 21:27

Everything went very fast and I I literally, I think two months later he moved into my apartment. A month later we were engaged right before my birthday, so that was the beginning of October, and the following May we got married and my friends were like, oh my gosh, she's turning 30. She's panicking. My friends were like, oh my gosh, she's turning 30. She's panicking. You know, she's just meet this guy and what the hell is she doing? And I remember I was second guessing myself Yogi, do you see? I'm recording a podcast right now. You have to wait.

Speaker 1: 22:02

I was second guessing myself and I asked my mother do you think I'm crazy? And my mother would certainly tell me. And she said no, he's the one for you. And the fact that she said that really gave me peace because I knew if you knew my mother, if you know my mother, you'd know she's not BSing you. Mother, if you know my mother, you'd know she's not BSing you. If she felt it and I felt it, then I knew it was right and it was right.

Speaker 1: 22:41

And even almost two and a half years later that he's gone, I don't regret a minute. I don't regret a minute. I miss him every second. You know, two and a half years later, it's still hard to believe that I'm never going to see him or talk to him again. But over time, the grief has shifted and what I've realized is that I don't have a choice but to close the door on that chapter of my life.

Speaker 1: 23:13

And you know we use these words, chapters, and you know I'm in my act three and all of these lovely expressions, but do we really mean it? Like, do we really get it? Do we really get it? And I don't think so. I think, when I look back, right, we know, okay, it's a natural progression that these, this is my childhood, and then I moved into young adulthood and and then I'm a full-fledged, functioning adult and we expect those changes, but we don't. It's funny, because why don't we expect that, that, that we continue to change and that the way our lives look, what do they say? I mean, the only thing that we know is true is that things are always changing, is that things are always changing and we expect to move from childhood to young adulthood, to adulthood, but we don't expect to move from, you know, full-fledged adulthood or middle-aged into this chapter, in this case for me.

Speaker 1: 24:25

You know, going from being together with someone for 30 years to now living my life again alone, as a widow, as a single person. But let's face it, of course it's going to happen right when you're part of a couple, I mean, it's life. One of you is going to die first, but we? Why would we think about it? It's too painful and it's too scary.

Speaker 1: 24:48

But two and a half years later, I'm proud of how I have moved forward. It's not my choice. I wouldn't have chosen this life. I wouldn't have chosen. I would have wanted my husband to be here, but that's not the reality. And so I am proud of the way that I'm evolving, continuing to evolve and excited to figure out on my own what I want this next chapter, this next act of my life to look at, look like.

Speaker 1: 25:22

And so, when I look back on all these three anniversaries, I have so many wonderful memories.

Speaker 1: 25:31

I'm proud of myself, on how I've persevered, not just the fact that you know 30 years, 31 years, not just the time, but the growth in myself over that time.

Speaker 1: 25:51

Time, but the growth in myself over that time. And I'm sure if you do the same for you, even if you're not celebrating any type of anniversary right now, just look back at pivotal moments of your life, times when you didn't think that you would get through, times that you thought would never change and you didn't have a choice and look at the evolution and I can look back very with so much love and fondness and, yes, I wish I could just jump myself you know time travel right back there, but I can't. But I have those memories and they fill my heart and they'll always fill my heart. But I know now that I'm a different person because of everything that I've lived through, and I'm excited to see what the next 30 years brings. You know, we don't get to choose every chapter that life gives us, but we do get to choose what we do with them. I hope something in today's episode inspired you in some small way. Thanks for listening and until next time.