Episode 1 - Julie Sheppard

How an unexpected reduction in force turned into the opportunity of a lifetime for Julie Sheppard, regional vice president of sales for a Fortune 1000 company.  Listen to how she shifted to Friday night lights + cowbell ringer!  

Transcript

SPEAKER_00 0:14

Welcome to the next chapter Conversations, a podcast about real life stories from people designing a meaningful second act or retirement. My guests will talk about inflection points and the paths they took to their next chapters in life. The goal for the podcast is to create more dialogue and build community around the R word. A word that was really hard for me to wrap my head around when my own journey into my next chapter began. My first guest is my friend and previous co-worker, the wonderful, funny, dynamic Julie Shepard. We met about 10 years ago at an employee orientation in Silicon Valley. We both came from the large tech giant SAP. When you leave a large company and take a job at a small unknown startup, you feel a kinship. It wasn't long before Julie started making an impact at work. Her tenacity, heart, and collaboration are three of the leadership attributes I would use to describe Julie. Over the years, Julie and I continue to talk about our careers, family, health, and our shared experience of caring for our mothers in the last stages of their lives. I've asked Julie to join me on the podcast to share her story about her path to retirement, how it started, and why. She'll share things she thought about and things that surprised her. I'm curious to hear what she's learned and can share with our listeners. Welcome to the podcast, Julie. Thank you for being with us today. Let's begin with you telling us about yourself.

SPEAKER_01 1:51

Well, that was very nice, Lisa. Thank you for asking me to do this. I have to tell you my age. So I'm 61 years old and I live in the Woodlands, Texas. The last company that I worked for was a company called DocuScience, and I was brought in to lead a group in the battle. So it was a brand new region, hiring all new people, developing sales strategies, marketing plans, aligning with the ecosystem of people that surrounded that region. And when I first started, the region was sub $5 million. And by the time I left seven years later, it was generating an annual business of close to 60 million, but total contract value of around 130 million. And we called ourselves the dream team. You know, Lisa, as far as you and I go, you coached me through a great time and also a challenging time. And you always push me to learn more. You always push me to be self-reflective. And I always appreciated that. And even our friendship today, Lisa, we continue to push on one another and make each other better.

SPEAKER_00 3:00

Yeah. I think that might be one of the nuggets as you go into the next chapter, is that learning mindset. What was the typical day like pre-retirement?

SPEAKER_01 3:11

The world prior to 2020 was very different. I was on the road, constantly in front of customers, in meetings all the time with our teams. It was running to airports, having meetings with executives face to face. It was following up at night. So we spent a lot of time working. So post-COVID era, the sales environment changed. I went from being out of the home and traveling all the time to being in the home and being more present for family and for friends. That's really important because when you asked me what was the transition to retirement, it wasn't as difficult because I didn't go from being out of the home all the time. I was actually transitioning into the home. So what's a typical day for you now? In the last year and a half, I've spent a lot of time helping to coach people through career transitions, helping them with their resumes, helping them solve problems. I'm a big workout person. So I probably spend two and a half hours a day working out and improve overall health. And that's something I'm super passionate about. I was a big time athlete when I was younger. And so this is something that's super fun. Most people think that I'm crazy when I do these hit sessions, but I absolutely love it. If I turn that sales passion into working out, it's working out great.

SPEAKER_00 4:33

Tell me about creating the new routine. What was your process for figuring that out?

SPEAKER_01 4:37

Well, some things have come up, for example, challenging myself. So my mother was a master gardener. She was a floral designer. And that was not something that I was very good at. So I thought, well, I'm gonna try it. That's one thing that I've gotten myself into um doing all the flowers for a baby shower. And I've done flowers for weddings. That's something that I feel close to my mom when I do it because she was so good at it. I thought I would never be able to do, and it's something that I've taken a hobby on. And I go to Trader Joe's every week and I buy flowers, I make flower arrangements. That's something that is new. Am I great at it? Yeah, I have have I have my moments. I've had some good arrangements, and I've had some that I'm like, I think I need a little bit more work here. That's something I didn't think that would ever do.

SPEAKER_00 5:25

Did you do that with your mom or did you just pick this up later on?

SPEAKER_01 5:29

I would watch my mom and she was so good at it. I would get frustrated because I wasn't as good as she was. My mom had late-stage dementia for the last four years, so she really couldn't do a lot of that. But when I would work on the flowers in the home while she was there, she would smile.

SPEAKER_00 5:45

Do you feel comfortable touching on the last couple years of your mom's life and the role that you and your family took?

SPEAKER_01 5:55

As the generation of people gets older, I think this is a real issue that a lot of folks don't understand or they don't realize it's coming. One thing I haven't mentioned is I have a husband, Phil, and then my son, Cole. My son is 20 and he's in college. Phil was very supportive of my mother. And my son learned a lot by having my mother in our home and having us take care of her. My father passed away eight years ago from dementia, so I had had a lot of experience up to the point where my mom needed more care. We brought her into our home and we had several caregivers that would take care of my mom. I was responsible not only for running a region, but also responsible for managing the logistics around four caregivers that came in 7 by 12 and then 7x24 towards the end. I didn't really talk a lot about it at work and it really didn't affect my work, but it's emotionally draining for people who have to go through that process. So my advice to you all is get as much help as you can and develop a really good circle of friends of people that you can talk to because it's hard, it's very difficult. But in the end, it was the most rewarding thing for me and my family. And for my son, who he was there with my mom until the last minute. You're going to see the evolution. A lot of people who are listening to this are going to see their parents age, and it's a responsibility that is going to fall in your lap, and you should embrace it, and you should make sure that they live their life as comfortably as they can. It takes a village for sure.

SPEAKER_00 7:48

It does. I was just at a dinner, and there was nine of us, and we were all going around the room. Everyone is faced with different levels of this scenario in their lives. Be it one parent or two parents. Some of us have already been through it, some are still going through it, but the love and understanding and support. Everybody's aging. What works for one family doesn't necessarily work for another. And I remember going through it with my mom and being able to pick up the phone and call you and talk to you about it. Aging and memory care, it's a completely new world. People might not ever have to deal with it or have any experience with it. So they can't understand, they can't empathize. So you can tend to keep it to yourself. I'm actually, like you, Lisa, helping provide that emotional support because you've been there. It's really meaningful to have somebody not theoretically talk to you about it, but somebody that's actually been through it. So who knows, maybe as the podcast evolves, we might have a session on this and bring some women to talk about it. So thank you for sharing that because I think it's an important part of your journey. That's going to be a nice segue in kind of the next phase. Tell us about the preamble to retirement and what was going on for you.

SPEAKER_01 9:10

I had not really been thinking about it, nor had I had expected to not be in the workforce. There was a riff and I was on that list. It was fairly shocking when my name was on that list. So I wasn't even thinking about it. But it was interesting because with my husband, I would say, okay, when we get to this financial level, I'll consider retiring. Well, of course, we get to that financial level like five years ago or five years prior to it. And he's like, Well, what do you think about that? And I'm like, Yeah, no, I'm not gonna retire.

SPEAKER_00 9:44

Let's pause right there. Why did you why did you say that? What were you feeling? Because a lot of people are in this dilemma too. This is one of those forks in the road. So why did you say no? What was going on?

SPEAKER_01 9:57

Well, I loved what I did.

SPEAKER_00 9:58

Yeah.

SPEAKER_01 9:59

And I loved all the people that I worked with. It was challenging, it was fun, it was hard, but it was rewarding. There's three stages, I believe, to everybody's career. You start off by being a learner, then you move into your earning phase, and then you transition to your serving phase. And serving is really all about you know, transitioning succession. I had moved into that serving phase and I loved it. I really did. Why would I step away from something that I loved? I also had to consider my son, you know, as he was moving into his teen years, he said something to me one day that made me take a pause. And he said, Mom, you're known as the invisible mother. And I was like, oof. Even though I went to every single one of his football games, I would change my schedule to make sure that I was there for his Thursday night games when he was in JV and Friday night lights. I was there when I wasn't present for the committees and the moms that were super involved. And you know, it's Texas football. That made me take a pause. And I said, you know what? I need to take some time away from work, go develop these relationships and become more of an integral part of his life because football and sports was very important to him. And it was important to me. And I was there all that. I just wasn't visible because I wasn't engaged and involved. So that is something that started to make me think about okay, well, when he leaves high school, he's gonna go play football. And I want to go see him play football, and I want to be that mom that's ringing the cowbell. Things like that started to tug on me. As I started to look at the financial piece of it, I started looking at the calculation of saying, Do I really need to work? And if I work, 40% of it goes to the government anyhow. And when I look at what it means over the next 20 years relative to our overall net worth, it was not worth it. It was not worth not having that time to be able to spend with the family, with my mom. And ultimately, when my son's at school, we go every weekend and see him. So those are some of the things that started to make me think about moving into a different part of my life outside of work.

SPEAKER_00 12:26

Yeah. On the tools and resources that you used or relied on for your retirement planning. Were you using them along the way? Tell us of your planning for that. And did you have a number? Yes. Okay.

SPEAKER_01 12:42

I got a number and I exceeded that number.

SPEAKER_00 12:44

And I still come up with that number. So let's take maybe a couple minutes and talk about the financial aspects because it's probably worth more than a couple minutes. That's one thing that I understand we are privileged to be in the position to where we get to retire. And there's a lot of people out there that aren't in that position. So I just want to just state that right now. We've also worked really hard. I've been super lucky, been in the right place at the right time, a lot of things, and been paranoid about money at an early age to where I started saving really early. And all that was kind of created the perfect storm for me. And I understand that that set of circumstances isn't out there for everybody. But to be in this position now, to be able to think about what we want to do with our time, I understand it's a luxury for a lot of people.

SPEAKER_01 13:28

Privilege of being able to retire, yes. However, the evolution of getting us to this point was really, really hard work. My recommendation is I don't care if you can only put $5 a month away, $100 a month away, and only put $2 a month away. You need to focus on having a fiscal discipline from a very early age. It doesn't mean that you have to give up your Starbucks coffee, but no matter how much you make, you can accrete value and financial wealth over a period of time. And that was my philosophy. The other thing, too, for retirement, which was something that was extremely stressful on me, was healthcare. Having a 19-year-old who plays football and knowing that I really needed to look at healthcare options, that was very stressful. It took me six months to finally find the right healthcare that satisfied family needs. It can be very costly, and it's something that prevents people from going to retirement. You really need to start planning for well in advance of retirement. And 65 Medicare people don't necessarily retire at 65, and not everybody has a pension where they have some level of healthcare that is available to them.

SPEAKER_00 14:52

How did you go about the healthcare process? Were there any tools? How did you unlock that?

SPEAKER_01 14:58

Well, I used a lot of the LLMs. I used Groc, I used ChatGBT, I used Gemini. So I started by doing a lot of research on all the various options. Okay. In addition, for those of you who have children in college, they offer a lucrative healthcare program for not a lot of cost, which I did not know until his second year. I wish I had known his first year. And then through research, ended up finding a great PPO program here in Texas. It was through private insurance. I don't believe that the ACA insurance options are very good in Texas. And now I'm on a really great plan. My son's on a great plan, and my husband is he's over 65, so he's well taken care of. With all of that, it literally took six months of complete research. Jumping in all the various websites, the government websites are difficult to understand. You have to look at what the options are, you have to look at whether your doctors are in the network. It was quite an extensive process.

SPEAKER_00 15:58

Thank you because healthcare is huge. On retirement planning, it doesn't sound like you really used any tools. You started early, you dabbled in some tech things here and there. Anything else to share with people? Obviously, we're not giving any investment advice or suggesting anyone do anything. This is more thought-provoking and conversational.

SPEAKER_01 16:20

You determine what are your debts, what's your income coming in, and what does that look like? And then also what's the legacy you want to leave for your family? All of that comes into consideration. And that's something that I've been doing for years. This is not something that I started in the last five years. This is something that I've been doing since I was 21. The one thing that I would recommend to everybody is don't get involved in assets or industries that you don't understand. That is where we've ended up not having financial success. I learned my lesson there, which is why we are more focused on areas where we have experience, both in the asset class as well as the industry.

SPEAKER_00 17:06

Sounds like your finance background is serving you well. Congratulations. When you closed your eyes before retirement, what did you envision and how's that working out?

SPEAKER_01 17:16

What's really interesting is my husband said to me, I'm shocked on how well you're doing. I'm not kidding. He said, You just loved what you did. He's like, I thought for sure that you were gonna have a really hard time transitioning into not working. And I said, So did I. I really did. It was really hard for me the first month because you go from having a super heavy schedule. I mean, you are literally on calls all day long. You you've got all kinds of responsibilities to all of a sudden you have nothing. Literally, it doesn't feel like anything. It was a little bit of a shock. Now keep in mind my mom was still here, so I, you know, I spent the next five months with my mom. So I I refocused my energy on that. It was football season and my son was going to college, so I had a lot of things that I could turn my attention to. And then I had the freedom that I really never had before. I had full control of my schedule.

SPEAKER_00 18:24

She has the biggest smile on her face right now.

SPEAKER_01 18:27

You know, if I want to get up at seven and have a cup of coffee and water out of my robe, great, I could do it. Before, I'd have to throw a sweatshirt on or a nice shirt and jump on a Zoom call, make sure my hair was like in condition. I can spend my time where I really love spending my time. Going back to the working out, that was something that I really wanted to get back to. So I had started working out about six months before I retired. We travel for football season. I have that freedom of being able to go if we want to go on a Thursday versus a Friday, if we want to stay over and travel somewhere on the East Coast, we could do that. So these are all the things that I really didn't have before and now I do. Now, with that said, there are times that I have downtime that I get a little bored. Last night I think I spent three hours rolling up bingo cards for I'm seeing joy on your face though. I know it's fine. So sometimes I'm like, do I want to do that right now, or do I want to just sit down and know I gotta get those bags done? It's rare that I have free time.

SPEAKER_00 19:34

Was retirement what you thought it was gonna be?

SPEAKER_01 19:36

Yeah, I think everybody's definition of retirement is different. What was yours? Yeah. I mean, my definition of retirement was just not working, and how am I gonna fill my time? That was really my definition of retirement before I actually got into retirement. Now that I'm into it, now you have that freedom of being able to do whatever you want to do. But also part of it is you have to keep yourself healthy. I see a lot of people who retire who have health-related problems, they're very sedentary, they don't challenge themselves mentally. Those are things that you cannot let happen because you will slow down. I get energy from being around people. So going to the gym, my trainer was like, you know, you're gonna know everybody's name in the gym. And I was like, okay, that sounds like a challenge. So I knew all their backgrounds and history, and he's like, How do you get this information? I was like, because I was in sales for 40 years. So that's fun though. I get energy from it. It's fun.

SPEAKER_00 20:40

What three things would you tell your pre-retirement self?

SPEAKER_01 20:44

Hmm. I wish that I had gotten into a leader role earlier because I enjoyed being part of a team and learning about individuals. I really liked that part. I really loved growing the business. I think it would have helped my career advance from a title perspective to like a CRO, but I chose to delay that. I would have challenged myself earlier. Probably would have spent more time cultivating relationships with parents of Coles friends, spent more time getting more involved in that because when I did, it was fantastic. I went to a football game this past weekend, and it was so fun to see everybody. I wouldn't have changed anything else. We moved to Texas to take care of my parents. That was probably one of the best things we ever did. That's really shaped our family. We're very service-oriented. I recognize that I get fulfilled by helping others. It's about what helps me feel better. And I really get energy out of helping other people.

SPEAKER_00 21:58

How do you explore an unpack? What those meaningful volunteer opportunities are for you. Because when I first retired, I had friends that said, I've got this opportunity or that opportunity. If you want to help fill your time, I'd listen to them. And I came away feeling I'm not looking to fill my time. I had to sit down with myself and decide what are the activities that are meaningful to me. I'll notice my neighbors are away and I'll take their trash cans in and they do the same thing for me. And it sounds funny taking your neighbors' trash cans in. It's something my mom used to do.

SPEAKER_01 22:37

Oh yeah.

SPEAKER_00 22:39

Yeah. That is meaningful for me. Those little things. Some of the committees and the events just don't appeal to me. And part of me feels like, oh gosh, it's a nice event, it's a nice activity. I should want to do that. I've had this conversation with people, they will have spent a couple of years doing something and they'll tell me, Oh, I'm not doing that anymore. And I said, Why? And they're like, I never really liked it. I don't want to spend two or three years doing something I really don't like, or that's not meaningful for me. How do you find things that are meaningful to you? And have you passed up on anything?

SPEAKER_01 23:12

Oh, yes. So, for example, I was on a board. It wasn't fulfilling, it wasn't my passion. So that's the one thing I'm happy to say no in a very nice way.

SPEAKER_00 23:25

I have a journal, and sometimes in the middle of the night, something will cycle in my head. I need to write this down so that I can let it go and go to sleep. To me, it was writing down and thinking about what those things were. Then, if an opportunity comes around, I take a look at my journal that keeps getting revised as I spend more time with it. What are those things that create meaning for me? It's a process.

SPEAKER_01 23:50

It definitely is. There will be things that I hadn't even thought about that will come about. I have a whole new circle of friends, moms. It's fun. That I'm sure will open up a whole new set of friends that I hadn't even thought about a year ago.

SPEAKER_00 24:07

Yeah. I think you touched on an interesting thing. I'm gonna call it a challenge of making new friends later on in life. If you have a common aspect like your children, working out at the gym, that makes it easier. Do you have any wisdom or insight on that?

SPEAKER_01 24:24

You can pick up a game of pickleball and go meet a bunch of people. My friend plays Mejong, which I've never heard of until she talked about it. And she's like, come with me. That's really not my thing, but I'll try it. Those are the types of things that you have to put yourself out there to meet new people. Our next door neighbor has kids that are in eighth grade and they're football players. So we go to their games. We're the older couple that goes to the games. It's fun. I'm like, hey, they're like, oh, you go to the gym. Oh, what's happening? What's your name? So if you just stay in your home and you don't get out, it can get lonely.

SPEAKER_00 25:03

Yeah. Okay, last question on learning and trying new things. How are you keeping your mind sharp? How are you opening yourself up to new learnings and new things?

SPEAKER_01 25:14

So this whole AI emergence is something that is very interesting to me. Before I left DocuSign, I worked with the team on leveraging the LLMs. So whether it's Grok or Anthropic or Chat GBT, any one of the evolving ones? I spent a lot of time studying that. I do it for a couple different reasons. One is helped me writing, doing research, and learning things that I literally didn't know anything about. You can cross-reference LLMs. We did a lot of that work before I left and I loved it. Truly transformational.

SPEAKER_00 25:52

How did your relationships with your spouse, family, or friends shift after you retired?

SPEAKER_01 25:58

Getting more involved with my son, with what he cares about. With your spouse, oftentimes they suffer because you have so many priorities. When you have a mother who's sick, she becomes a priority. When you have a child who needs attention, they become a priority. When you've got a big deal you're working on, that becomes a priority. So sometimes your spouse doesn't get as much attention. So that's something I'm aware of that needs to evolve.

SPEAKER_00 26:31

Yeah. How one of the things that's crossed my mind, and I'm curious for you, how does our partner relationship change? You were on the road three and a half days a week, and now you're not. How has that changed? Bill, he's actually gone during the day.

SPEAKER_01 26:47

He's a worker. The caregivers would say to us, I've never seen a couple move and groove the way you guys do. They said, from Phil doing dishes to you doing dishes to you cleaning up over here to him doing something outside to running and get the groceries to get stuff for Cole. He did all the laundry. They said it was amazing to watch you two. So we mesh really well. I think if it hadn't been for work at home, I think it would have been a much harder transition.

SPEAKER_00 27:16

Yeah. Have you had or do you need to have any kind of conversations about, hey, this is what I need, and soliciting what he needs and recontracting the next phase in life for what's going to work for you individually and collectively? I can imagine that that might have to happen with myself, but this isn't about me. So I'm going to ask the question and get a nugget or two from you.

SPEAKER_01 27:42

I would say that this is an area of evolution. And that I actually was going to recommend putting a PowerPoint presentation together or Google Slides or whatever it is, so that I could sit down with him on Sunday and say, okay, here's how we did this week. And he's like, that's way too professional. And I was like, I know, but that would really help me stay on track with our covers. Yes. So work in progress. It's work in progress. But I mean, look, it's all about communication, right? And so we're working on that. First step to everything is knowing that you have a problem, right? So we're in step one.

SPEAKER_00 28:22

It's, hey, that could be better. We've gotten this far in life and we've gone through all these things and we're a pretty good team. And how do we optimize? I really believe that you have to challenge yourself.

SPEAKER_01 28:34

You have to continue to learn. I don't care how old you are. Look at Warren Buffett. He's in his early 90s and he's still learning. I try to self-reflect to see how I can continue to get better. I'm constantly working on and thinking about.

SPEAKER_00 28:51

What's about getting better for yourself? Because I think as women of a certain age, when you've been a mom and a daughter and all the roles we play, and I'm not even throwing work in there. For a lot of us women, it's all about making sure everybody else is taken care of. I'm finding at this phase in life, now that I'm retired, what do I want? Oh wow. I've been living my life and very happily, I'm still unpacking that and figuring that out. I'm not even ready to have the conversation yet. This podcast is about everyone figuring it out for themselves, everyone's journey, pre-retirement, in retirement, all of that is highly individualized. It's different for everybody. That was a lot of fun. I really enjoyed hearing from Julie, especially the freedom in retirement. Who doesn't want that? Challenging yourself every day was a good suggestion. On the financial aspects of retirement, saving early. That seems like a key. If you've missed the boat on saving early, just start saving and putting money away. When you get increases, increase your contributions. So financially in retirement you're set up. I never thought about her perspective on understanding your investments. I think that that's something to consider. Check us out here or online at NextCapter Conversations dot com powered by GoDaddy. Have a good one.