A Total Career Change at 50 with Jennifer Dillan (Ep 19)
Making a major career change is never easy, but that’s especially true for someone who's worked their way up to a well-paid position in their current industry. But as you’ll hear from Jennifer, sometimes your mental and emotional wellbeing is more important than a fancy title or huge paycheck.
In this episode, I’m chatting with creative director turned real estate developer Jennifer Dillan on her decision to make a career change at 50. She’s sharing how she decided to change industries and how she transferred her skills into her new position. Plus, we’re talking about making a career change for your mental and emotional wellbeing, even when your pay and title seem too good to give up.
In this episode, you’ll learn...
Where Jennifer is on her journey and how she got here [2:03]
How Jennifer shifted her skills as a creative director into her current role in real estate investing [4:52]
Finding the courage to make your leap when you’re burnt out from your current position [7:34]
How Jennifer found a community of women in real estate who want to see her succeed [14:09]
How to start networking before your leap, even if you’ve never done it before [14:57]
Finding your confidence and direction as you transition into a new position or industry [18:42]
How Jennifer’s stage in life influenced her decision to make a career change [21:04]
How Jennifer developed her exit strategy and finally quit her job [25:50]
Finding yourself in a new career when your identity feels connected to your work [28:00]
How networking helped Jennifer land her first position after her big leap [32:18]
Deciding between a minor industry shift and a total career change [36:01]
Why your wellbeing should come before your pay and benefits [38:19]
Jennifer’s advice for anyone who wants to make a late-stage career change [45:52]
If you’re considering your own courageous career leap, be sure to tune into this episode.
About Jennifer Dillan
After over 25 years in advertising, sales, and marketing, it was time for a change. Jeinnfer quit her job as a Creative Director -- without having another lined up -- after 13 years at a global humanitarian aid organization to get her Master of Real Estate Development (MRED) degree when she was 50 years old.
Jennifer subsequently landed a job at a small firm that is leading the movement in the US of sustainable engineered wood construction called mass timber. She worked full time and went to school at night for 3 years to make the transition. Her passion is 'missing middle' housing; smaller homes that fit naturally into neighborhoods and are affordable for the community's workforce (nurses, teachers, shopkeepers, etc).
She recently transitioned to focusing exclusively on her own projects, and some consulting work. Currently, she is working on an affordable, public transportation-oriented apartment building, as well as 36 net zero townhomes clustered around a communal green space, called a pocket neighborhood.
Connect with Jennifer
Connect with Jennifer on LinkedIn
Standing at your own crossroads and ready to get clear on your direction? Apply for my Catalyst Coaching Program today!
Transcript of Episode 19: A Total Career Change at 50 with Jennifer Dillan
[00:00:05] Lisa Welcome to Leap Like Me, if you can't shake the feeling that you're not on the right path. If you feel called to change things up but don't know how to begin, you're in the right place. I'm your host, Lisa Hoashi, and my specialty is coaching people at those crossroads moments in life when you feel called to take a new direction. Sometimes that means taking a leap. I want to share practical advice and inspiration for your lips and how to keep going after your dreams in a challenging world. This season, we're talking all about career leaps. Come along for the conversation.
[00:00:50] Lisa Hoashi Jennifer Dillan had worked in advertising, sales and marketing for 25 years. She was a creative director who had built her team of 10 from the ground up over 13 years at the same organization. And then she quit her job without another one lined up to get her master a real estate development degree. A total pivot at age 50. In today's episode, we hear about what prompted Jennifer's Leap, how she discovered the right path for her and how honing her networking skills helped her navigate the change at 50. Jennifer and I worked for the same global humanitarian aid organization in Portland, Oregon, where she was creative director, and we often work together closely. She was phenomenal at her job. Yeah, as she shares today, it was taking its toll. I was so inspired to learn how she regrouped and made this leap to a totally new career that's fulfilling, healthier and happier. Listen in to hear the story. Hello, Jennifer. Welcome to weep like me and thank you so much for being on this show to share your story.
[00:02:00] Jennifer Dillan It's been a pleasure to be invited. Thank you.
[00:02:03] Lisa Hoashi All right, so let's get started with first of all, just where are you and what are you doing for work right now?
[00:02:11] Jennifer Dillan Well, I am a real estate developer now. I build neighborhood workforce housing in Portland, Oregon, with mass timber, which is an engineered wood product that is very sustainable.
[00:02:23] Lisa Hoashi And so what you know, obviously you are on the show today because you have made some sort of leap. So can you tell us about what were you doing before? And a little bit about that leap to kind of get us, get us started?
[00:02:36] Jennifer Dillan Sure. I was a creative director at a nonprofit organization, a global nonprofit for 13 years and had been in marketing and branding for twenty five years. And I knew that I needed to make a change. There were a lot of forces at work at that organization, and my burnout was pretty acute and I knew I needed to make a change and I didn't feel passionate about marketing anymore. So I chose something totally different that I'd always wanted to do and started putting plans in place to make that happen.
[00:03:11] Lisa Hoashi And so, I mean, that's such that such a big way. So you I mean, you had dedicated like 13 years in this field and in this role. And so to just kind of like, stop suddenly. Will you tell us a little bit about just like, how did you feel like leading up into that moment? Like what were some of the signs like, really needed to happen and kind of like walk us through like that process?
[00:03:39] Jennifer Dillan Sure. Well, I was very much at a low I the organization when I started was very scrappy, was on an exponential growth trajectory. I found that really exhilarating. I was thriving. I was empowered to be autonomous and build my own team. I had a seat at the table. Things were moving quickly. And as the organization grew, that ceased to be true and those opportunities started to kind of evaporate. And it became much more bureaucratic, much more bogged down in process and politics, and therefore a lot less enriching. It just wasn't feeding my soul. And more than that, I was taking a huge toll on my mental and physical health. The stress was just so chronic for so long, and I, I had gotten used to that. It was kind of like being the frog in the pot of boiling water and just bringing it to a slow simmer. I just had normalized it and I didn't see a way out for myself. But once I started having health problems, I knew I needed to make a change in that it was really important to do it soon. So I started to look for other opportunities. Real estate is something that goes way back in my history. My father bought and sold real estate when I was a child, so it didn't seem so intimidating and scary to me. I can now look back and see a lot of points in my life where I was pursuing various forms of real estate investment in my life and just hadn't done anything with it yet. So people often ask me, you know, gosh, there's nothing similar between creative director and real estate developer. And it's a good point on the surface, but actually, there's a lot in common. I love to build things. I love to build teams. I love to build, to see a problem and find a solution to it. I love making things happen. I like finite projects where it has a beginning, middle and an end. And then you then you get to start a new project. It would be terrible at iterating like just small iterations endlessly for years, that would not be my strength. So actually, real estate development is very much like creative direction. And if you're if you're making a product, a real estate developer is like an orchestra conductor. You have a vision, you decide what piece you want to play or building you want to build in this case. And you start to collect your team and it needs to be a really well-balanced team to make it sing just to keep it. The analogy to make it really work well and that's the role of a real estate developer is to bring a project from concept all the way to fruition successfully, profitably, beautifully, sustainably and in my case, and really have a contribution. Make a contribution to your community in the way in which I was very much doing as a creative director as well. I had a team of 10 people at the organization, and I was just conducting that team all the time to deliver something that would be of value. So.
[00:06:53] Lisa Hoashi Mhm. So what you're kind of seeing now that you are like in this new field is that essentially like the elements of your role are very similar to and like play to your strengths and you've kind of transplanted them into like a totally different field.
[00:07:11] Jennifer Dillan Yeah. And I think that's what made me good at building that team at the organization, the creative team, and I think it's what drew me to being a developer is because it's what I love to do, and it's what started to be kind of, you know, death by a thousand cuts when I wasn't able to do it and when I recognized that that I wasn't doing what I loved, that I wasn't driving and I needed to leave.
[00:07:34] Lisa Hoashi So the I mean, it sounds like that the real life assigned to you was like, you're experiencing burnout and like really feeling those like, how like you a spiritual and physical, you know, like signs that it was time. And so I, you know, when I think about like my only observed, you know, realizing that I was, I needed to, like, make a big switch. And at the moment, but like, I took my sabbatical year, I just remember, like coming home to my apartment in the evening and just like sitting down and just being like, I know this has to change, but I'm so tired. I don't even know how I'm going to make a change. And so it sounds like that that resonates with you. I mean, I hear that from other people, and I feel like that's like one of the harshest parts of like making a big change like this is often you feel like so low confidence, so low energy, just terrible from burnout. And it's like the moment when you actually yeah. And it's the moment that you actually need to feel confident and you need to feel full of energy to make good decisions for yourself. So how did you tackle that problem?
[00:08:46] Jennifer Dillan Oh, so hard. It's so hard, right? Because, you know, I was sitting on quote my dream job making good money, great benefits, working for global humanitarian organizations. So I felt like I had my angel wings whenever I walked in the room, which is a 180 from being a real estate developer, right? Because they don't really have that. And I did, like you said, it's really interesting. You say that your my confidence was so low, I just felt so depleted. And as is the case in life, so often hitting that low is the thing that often motivates us to make something happen, right? We've now reached a point where we are unhappy enough, desperate enough to take that risk and do something about it because it's just we just know we can't go on that way. And that's what happened. So, yeah, I summoned all of my energy. I started networking about four to six months before I left my job. I just frantically networking not to get a job, but to understand if this really was going to be the thing that worked for me.
[00:09:59] Lisa Hoashi So you already had the hunch that it would be into real estate that you would go into?
[00:10:05] Jennifer Dillan It was an idea. I had this idea that I would really like to do it. It was an unfulfilled dream. I had discovered that the college here, Portland State University, had a very reputable master program master degree program in real estate development right here in town. And so I went to an orientation for that program that ignited some interest and passion and kind of like, Ooh, this might be something I could actually do. And it gave it shape and form and color, right? Like, Oh, I could plug it into this program, jumpstart my knowledge. It has the it would give me the structure. To do that, to make this change. And I started networking like, who do you know in real estate? And then I just started at work at at the organization. I like trusted friends, and I just started to build this understanding of the local real estate development community. And I actually had even a chart up on my wall with all the connections names like little cards with the names and the projects they built and who they worked with. So I could create this kind of spider web of who's who in the community and what buildings they built and who they built them with. So I could understand the ecosystem a little bit. And my head was going to explode like it, working full time, 50 plus hours a week. At my very stressful job networking, I was probably doing two to three copies a week and entertaining and then eventually applying for a master program master's program at 50 years old was a lot. And at the same time, all those coffees and the application process started to energize me. It started to give me hope that there was something else out there for me that would be better and exciting and new, and it started to build a momentum in me that just created more and more clarity.
[00:12:14] Lisa Hoashi Mm-Hm. So, yeah, I mean, that sounds like a theme that I often hear and where I'm often late trying to get my clients as to like that switchover point. So like we said, like, there's that like a very low point, right, where you're just like, how am I even going to master? I mean, maybe even the energy for like one networking coffee, right? Yeah. But then it's like, you do that coffee and you hear something kind of interesting and or that, you know you and then that curiosity or the interest starts to get piqued and starts to lead to like this greater motivation and momentum and returned on energy like we're starting to get excited.
[00:12:54] Jennifer Dillan Exactly. And not to be too trite about it, but I hadn't worked for 20 years and it was kind of like dating, you know, like the first, the first few coffees, I was just like, Oh, what are we going to talk about? And this is awkward, and I got to put on my lip gloss and, you know, like the whole thing and be on, you know? And after, you know, I got one two three coffees under my belt and I kind of could speak more articulately about what I wanted with someone and and then practiced asking them if they wouldn't mind introducing me to a few of the context we had discussed in bring the coffee. I mean, those were gold. It was gold to have someone in the industry write an introductory email saying, Hey, I'd like to introduce you to Jennifer Dillon. She's really excited about getting into the industry and your name came up that that that resulted in more momentum than anything. So once I started to understand how to do it and how to be genuine and authentic in those meetings and ask be be specific in my ask about it would be so great if you'd be willing to X or Y. People almost always said yes, and I'll just add this. One thing is the women in a real estate is not known for its representation of women. The vast majority are white men in real estate, and women are few and far between. So the women that I met with, who are in the industry were very passionate and dedicated to advancing other women within the industry, and that also inspired me. It was a little unexpected. If I'd thought about it for a hot minute, that would have made a lot of sense, but I just was kind of caught up in the occupation of it. And there are a lot of really amazing women who who went the extra mile for me, mentored me, returned my emails, my phone calls and my texts. And they're busy people. But I think that they understood the mountains that there was to climb.
[00:14:57] Lisa Hoashi There was really cool. OK, so there's so much here that I kind of want to dig into. So, all right, so you were turning 50. And so first of all, I hear that like there was that like when it came to networking, like you hadn't done it. I mean, really just based on how long you had been at your previous job. So it was like coming back to it kind of like, how do I do this right after 13 years? Yeah. Or what did you say, 13 years? There was a 20 that you said,
[00:15:27] Jennifer Dillan Well, I hope that that organization for 13 years, but I probably. But I got that job after one interview with no networking required, so it probably was twenty since I've had to get a job.
[00:15:40] Lisa Hoashi Uh huh.. Yeah. All right. So Jen, well, let's start with with that then. So for someone who has like you? Maybe never had to go out and network to get a job or have not have not done it like in the last 10 years. What would be kind of your top tips for how to approach it, how to kind of get over that initial bump, you know, and just start feeling a little bit of confidence? And also, I'm really interested in what you said about being really specific and asks, like if you could give some examples of that.
[00:16:13] Jennifer Dillan So the first recommendation I would make is start with your close circle, start with your friends, family, other trusted colleagues. And if you're already talking to them about entertaining a career switch, talk to them about Do you know anyone who is in that industry? Do you know anyone who's doing anything like that even now that we're all so used to zoom and phone calls? Totally normal to call someone out of town and have a conversation with them. It doesn't have to be an in-person coffee, but start. That's such a great way to warm up. You know, if you have a close friend, it's easy to call their close friends and ask them. So, yeah, I would say that that's one of the first things I would recommend. And then the second thing is just go in to the coffee with an expectation, especially your first two three five that you're warming up. You know, acknowledge that you're warming up. Come in with some questions. Understand their time is limited. Be respectful of their time, of course, but just get out of it. It's a big deal to get out of it that you're more comfortable and that you've found your voice, and that you can articulate what you want or don't want or identify a certain questions that you have about if it's the right fit for you. And then I think the last thing I would say is that do come with a specific ask of people. If you ended up talking about let me back up, I think I always asked, Do you know anyone else who you would suggest I talk to about this career transition and people 90 percent of the time came up with at least one more name. And then my next question was, would you mind connecting us? Would you be comfortable introducing me to that person through email? And again, 80, 90 percent time they said yes. And that was really so important because people will respond to someone they know. Right? I would like to introduce you to Jennifer, and they would respond. Great. Happy to meet you, Jennifer. And then I had a direct connection with this person and that made things go a lot faster. I didn't do that until probably my eighth night interview when
[00:18:30] Lisa Hoashi I like benefiting from you. Yeah, we can. We can do it quicker, thanks to do it sooner.
[00:18:38] Jennifer Dillan Say I lost a lot of contacts that way, but that those would be my tips.
[00:18:42] Lisa Hoashi How did your like through all of those meetings? How did you see this evolution? What was evolving for you as you went from session to conversation?
[00:18:54] Jennifer Dillan Well, I think two things. One is I was starting to understand how the industry worked a little bit better and literally what the titles of people meant. You know, it's not always a very intuitive industry, so understanding what role people played and where they plugged in to different projects was a big epiphany for me, and it helped me understand where I wanted to plug in to projects if I understood that that process more. And then I would say the other thing is that like I mentioned before, I was building this ecosystem of cards of those who in the industry here in Portland, Oregon, by connecting some dots on who was building what projects and with one of their partners. And that also allowed me to connect with more developers and also understand work in the projects they were building me myself. A passion is kind of in the small and mid scale development. I want to be building housing almost exclusively for multi-use projects that are urban infill projects here in Portland. That's a very specific kind of project versus I'm not so interested in industrial, I'm not so interested in huge office buildings. I'm not interested in Highrise. So it allowed me to focus and get more clear on who was doing the kind of projects that I wanted to be doing.
[00:20:20] Lisa Hoashi So you're basically learning like how how does the industry work as well as like all the like I often think of, like when you're switching from one field to another, you're having to learn like a different language, like you have to learn what the different titles and jargon and everything means and then be able to communicate about yourself in that same language. Right. So and it also sounds like you are also figuring out where you wanted to go. But then that world?
[00:20:46] Jennifer Dillan Yes. And steep learning curve. When you when you leap to such a dramatically different industry, it's a steep learning curve. But it doesn't last forever. Your brain, your brain starts to learn and it's kind of fabulous feeling when you start to connect the dots.
[00:21:04] Lisa Hoashi Well, and then to go back to the the like the landmark age of 50, like, did that really influence this change for you? Like what were some of the factors that came into play for you?
[00:21:18] Jennifer Dillan Yeah, huge. Huge deal that where I was in my career, where I was in my life, really informed that decision and made it scarier as well. Late career change is not normally a career pivot, not just change. Career total pivot is uncommon. I found out, and it generated a little bit of reaction among friends and family, you know, just like very compassionate concern, but concern nevertheless. I had gone through a divorce two years before that change, so that had changed in my life and my kids were growing up and they were heading out of the house that I was changing my life. And I had also kind of fallen into that career that I was in. And as many of us in the middle of our lives, do we wake up and go, Is this what I want? Is it enough? What do I want for the last trimester of my life? What if I want it to look like? How do I want to feel? And some people call that a midlife crisis. I think it's a gift. You know, we have this kind of awakening like, Wow, I can do something else and I have this opportunity to do it. I think being in the middle of your life, you have the experience, kind of the wisdom, kind of resourcefulness, usually to be have perspective about your life and and what you want. What's made you happy in the past? What what do you want to be? So that's where I was. I was like, I think I I can change this and I have seen all this other change in my life and I can change this. This too. And I saw that there were there's more potential for me than just where I was. Yeah, big moment.
[00:23:13] Lisa Hoashi Yeah, yeah. Well, you aren't alone. I mean, I often have people want to come to coach with me at like 30, 40 and 50. Yeah. And yes, I would say like 50 that there is that real question of like this potentially is like the last important era of my working career. And I really want to make some choices that are really meaningful to me and like the. So it is exciting because there's like this potential. But I do think there's also that fear of like, I can't mess up because then I can't I'm like too old to mess up. Like, there's not there's not grace room for me, you know, or like this kind of, yeah, I don't know. So I'm just curious, did you feel that?
[00:24:04] Jennifer Dillan Oh yeah, there's a lot of pressure there. I think it's really important to acknowledge that people who are, let's say, between forty five and 60 who want to make these kinds of the changes are in a wide range of financial situations. Some people have done more for themselves, and they can allow themselves a year of grace period or more because they have a safety net with some other people, not at all. And that I think it's important to know that that makes it a lot harder. Sometimes the demands when we're older are more because we have aging parents or other obligations, and sometimes they're less. I was on the side of seeing that. I was having less obligation in my life. I had my dog, you know, I didn't.
[00:24:55] Lisa Hoashi I didn't know I had.
[00:24:57] Jennifer Dillan I mean, I had my children. I have a house. I have a lot of obligations, but I didn't have toddlers. I didn't have a lot of things that would prevent me from dedicating myself to something new. I did not have a lot of savings, so that was a big. I did have some, but not a lot, and that was a big concern for me. And taking out loans to get my master's degree at 50 years old was the biggest decision I made. I don't regret it at all. It served the purpose that I had intended it to serve and that was worth it. That was definitely worth it. And it gave me the structure and networking community, my cohort, my professors, career counseling, they the network that the school provided. All of that was worth it.
[00:25:50] Lisa Hoashi Yeah, so maybe we could pick out like kind of chronologically again, so you have quit your job and then you just. Well, tell me what happened from there. Maybe we'll just start there.
[00:26:04] Jennifer Dillan Let's let's back it up even a little bit further. I would say about six months before I quit my job, I knew I needed to quit my job. So I started to plan an exit strategy six months before I quit. I didn't know when I was going to quit. I didn't know how long it would take. But I now know it was about six months before I left, so I started to explore these other alternatives. I started my networking before I quit, and I would say about three months before I quit, I realized there was this program in town the the master's degree program, and the application was due soon. So I applied not knowing if I would go. And in the meantime, my need to leave was getting more and more obvious. So I accelerated these plans and the moment that I was accepted to the program, I knew I was going to go. I accepted. I applied, was approved to go and I gave. I told the admissions office I was coming. I gave notice about a week after that and that was maybe in August, and I quit my job in September without another job in sight because I knew I couldn't look for a job and do my career at the same time I started school. And then six weeks after that, I got my first, my job in real estate in mid-October. That's the chronology. Mm-Hmm.
[00:27:35] Lisa Hoashi So it was a big moment, I'm sure, like lots of emotions of like having to kind of process leaving the job saying goodbyes. Yes, grief always is part of like leaving some financing gap and closing the chapter right? And then you're starting something new and then wondering, like, am I going to make money and pay for this?
[00:28:00] Jennifer Dillan Yes, exactly. And and the leaving process was heightened even more by the fact that I felt my identity was wrapped up in my career and specifically my identity was wrapped up in my team. This is a creative team that never existed, literally. It wasn't until this Indonesian tsunami and the Pakistan earthquake and Hurricane Katrina that the organization started to funnel money toward me because I had experience in advertising. I said, Yeah, hire a part time photo librarian, hire a part time production artist, hire. And it just grew from there. And then after 13 years, I had this beautiful team of 10 super talented people who was churning out work that was fueling hundreds of millions of dollars in fundraising. So I was very emotionally invested and my identity was wrapped up in it. So leaving it felt like I didn't know who I was anymore, and I just was praying that I would find a home in this new industry and that I could be happy. So it felt like a huge risk, and the grieving was not insignificant and the concern that I didn't know who I was going to be anymore. Mhm. And I was almost immediately happier. I was so much happier. I was so excited. I was so energized to be in the classroom. It was it was like, Oh. I just like I just felt younger, more energized. I felt excited about the possibilities I was having all these ideas. I wasn't anyone's boss anymore. I really loved my cohort, my at school and we started. I saw all the momentum and possibility and started to have very specific interests within the field. So I started to form my identity in this field and I found a home there pretty quickly. And the transition was very, very hard and especially that I didn't have another job that I was landing into and I had no skills to offer in the new industry. So not insignificant.
[00:30:22] Lisa Hoashi Mm yeah. Well, I really appreciate you sharing like the feeling of identity. So we worked for the same organization and that was like, you know, it's a very like it's a mission driven organization. It's like high stakes work, super important. People are super fired up about and close knit. But I realized that I had the same thing. Like when I left it, it was. I had this fear of like, Am I going to know who I am afterwards? And it was really weird just to admit to myself, I don't think I said aloud to anyone at the time. Like, I was just such a weird feeling to realize how much of my identity and how much fear there was of, like I wouldn't know myself afterwards. But it sounds I had to kind of a similar experience of just like once I started tapping into interests that, like were awakening parts of me that had been kind of lying dormant. It was like such a reassurance that like, I'm still me, it's all still here. I'm going to find what interests me, what I'm good at. Like, it's it's going to. It's all coming. It's natural, like it comes back fairly naturally. You know, it's just about allowing some space, which is like the really scary part, you know? Yeah.
[00:31:37] Jennifer Dillan Someone once said to me, Jennifer, you take you wherever you go. You know what? They were reassuring me, Don't worry, you know what you built there? Who you are, what you brought to it, the energy, the creativity you brought to that job taking with you. It doesn't stay there. It's who you are and you're going to take it with you and just apply it, maybe differently. But the same way, because like you said, it's they these are dormant parts of ourselves or unexpressed parts of ourselves that get to come out in a new way. But they are. They do live with you. You take them with you. They don't live at your desk with your computer.
[00:32:17] Lisa Hoashi Yeah. So how did you actually go then? How did you get that job?
[00:32:22] Jennifer Dillan Yeah. Well, it's funny because I did all like I said so many times, all this networking and then it in the end, ironically or not, ironically, I think it works this way. I got a job because one of our former colleagues, who I was close friends with as well, I had lunch with him. He was abroad. He is a country director, but he was in town. We went and had lunch and I was telling him what I was up to and he goes, Oh, you need contact. My friend is a developer here in town. He and I grew up together in Cleveland, Ohio, and I went, Yeah, he's not returning my calls or my emails. He's been recommended several times and he's like, Oh, he'll help, and he just like sends to them, right then. I got an email later that day, he said, Sounds like we better have coffee or I'm going to be trouble with my friend. And we went to coffee and we probably had a two hour coffee. We have a great coffee. Hit it off and we ended up hiring me. I got an email, maybe two weeks after the coffee, saying, Hey, do you want to want to come work for me?
[00:33:26] Lisa Hoashi Awesome. So what was the what was the initial role like out of the what did he hiring you for?
[00:33:33] Jennifer Dillan Yeah. Well, he hired me to help project manage a wrap up the construction of a project that was he was finishing up. So I was in a construction trailer with his senior project manager. Just not even full time yet. And for a very low wage, hourly wage, just it was just a brutal transition. Just in all honesty, it was just like I was and I had my down coat and my hat and my gloves on, sitting at my computer going, Oh my gosh, what have I done? This is this is not what I thought it would be, you know, I was thinking of, you know, sexy office and real estate development. Here I was in this trailer. But that's how that started, and I was doing punch listing and trying to be helpful to the to the project manager. But I also brought my other skills. I immediately knew that I. Needed to add value right away as I was training up, so I brought my marketing skills and I totally rebranded the company. I asked like, Hey, I noticed your website doesn't say anything about mass timber. You know, let's pivot to just this being all about who you really are, which is being really on the cutting edge of the mass timber movement. And to his credit. My boss was like, Go go, just do it. So that's what I did. And that, I think, added a huge amount of value while I was also learning all about being on a construction site and still being in school. And I'd say about four or five months later, I was in the office and at the table, at the meetings for the next project and just things evolved from there. Very small firm only six people at the time.
[00:35:27] Lisa Hoashi So I love that that image of you, I'm just like, you know, you're in the trailer, like in your coat and construction hat, like going from, you know, nice office where you have your whole team. And just like, Yeah,
[00:35:40] Jennifer Dillan oh yeah, I used to dress with heels and everything. And then I'm like in the construction trailer, like, Oh, it was kind of great. It was great. And also just a moment, it was
[00:35:55] Lisa Hoashi something that was like, Yeah,
[00:35:56] Jennifer Dillan yeah, where where am I
[00:35:58] Lisa Hoashi going with this? Yeah, what should I do? Yeah. Well, you bring up an interesting I guess there's kind of a wrinkle here, which is like with all of your branding and marketing experience, like I could see that there. You could have approached all of this by just saying, Oh, just take my branding and marketing and move it to a different field. Yeah, but you haven't really done that. You really like took on a different type of role. Is that correct? Or how how would you say, let's say that?
[00:36:29] Jennifer Dillan I would say that it was a hybrid. I think that given that it was such a small firm and it was all hands on deck which had tremendous upside for me, the the firm that I worked for is has all of the architecture contracting and development in-house, which is unusual. Usually there's developers and they hire architects and they hire a general contractor and those are all different companies. But this small firm did all of them in-house, and because it's such a small firm, I had visibility into all aspects of that process, which as a developer is, you know, incredible to watch the entire arc of a development like that. So that was a huge benefit, and I was learning. I mean, I just my first year in school, I was learning from the ground up, so no pun intended I was I was really trying to bring my marketing value to the company because one, they needed it and I knew kind of what to do right away. And it was self evident and I felt I had the skills to do it and that it added the value while I was in school. And I will also say that my boss was very supportive of me being in school, and that's that's important to not all employers support someone. I was going to school at night, sometimes had to leave work a little early to get to a class, that sort of thing. So it was a great hybrid of the two for the first while. And then I was able to pick up a little bit more responsibilities around project management, property management, grant writing, all that sort of thing. So trying to accumulate more skills in addition to what I was doing, but it was very handy for me to have the experience that I had.
[00:38:19] Lisa Hoashi Mhm. Now you mentioned earlier that you really were pleased with the master's program that you really felt like it served the purpose that you intended it for it to have.
[00:38:30] Jennifer Dillan Yeah. Again, back to where I was, where I am in my life and my career, my age. I didn't have time to just embed myself in a firm like that and spend 10 years learning as we did various projects. And that's something that's a young kids game, right? Like not having to do it. And that's how most people learn. Real estate development is they they get a job in the industry and kind of work their way through various positions and learn the field. I didn't have that luxury of time also at my previous job. I it's that's exactly what I did. I worked my way up into the position, into being a creative director, and I took a very unconventional path. I'm not traditionally an art director by experience or a copywriter. I taught myself some of those skills and my background in advertising, of course, informed a lot of that. But it's not the traditional path for creative director and as the organization was becoming much larger and the fundraising machine. Is getting so much more sophisticated. That was to my detriment. There were voices in the room that were saying, Well, you know, Jennifer doesn't really have the experience that you need at this point, which is, you know, some fancy creative director from a big agency who can take us to the next level, for example. So I was hearing that kind of reflected back to me that I didn't I didn't have the credibility, even though I had done what I had done didn't feel good. But also I had the opportunity to expedite my career trajectory by going back to school and learning in two years or three years what I could learn and seven or eight or 10. And also kind of check that bought that credibility box and say, Look, I know I'm 50 years old, but I have my master's degree in this field and I'm ready to go. And that was kind of undeniable. I think that degree has a certain amount of cachet in this town, and I wanted that calling card when I walked in the room, especially because of my age, especially because I'm a woman. You know, women in their fifties are sometimes, you know, there's some perception about that. You're not going to be a hard worker or that your best days are behind you or some other kind of unconscious bias about women who are middle aged in a career, especially that are starting a new career. And I kind of wanted to cut that off at the knees as much as I could. And it's done that. It's done that.
[00:41:10] Lisa Hoashi I'm smart and strategic like that. You really took like things that you had observed already from your previous path. And we're just like, I'm going to can have mitigate this or eliminate them the best of my ability for the next one.
[00:41:25] Jennifer Dillan Yeah, because I feel terrible because I'm like, really, no matter, no matter how hard I
[00:41:31] Lisa Hoashi work, yeah,
[00:41:33] Jennifer Dillan how much I've achieved, how much of work to even look at all the numbers and all this sort of thing. And it's still kind of like, Oh, she doesn't, you know, she didn't come from this fancy agency she didn't like, didn't work with Coca-Cola and Nike or these types of things. So there was not going to be a way to get around that. And yeah, I made a note. I made a note that I didn't want that anymore.
[00:41:54] Lisa Hoashi Mm. Well, Jen, I guess, is there any other part of your story that you really want us to cover today before you start wrapping up? Is there anything where any points that we've missed are you really wanted to?
[00:42:07] Jennifer Dillan I don't think so. I think we covered. We covered a lot of them. I think if anything, I would just say how reiterate again that it was really hard and the relief I felt was instantaneous virtually. And it's I've been healthier and happier than I had been in that whole time. Or at least I'll say at least the last five years of my my last job. And it's allowed me to discover new things about myself and have kind of a new lease on life. So that's that's I'm really grateful for that and I would do it again in a heartbeat. Yeah.
[00:42:53] Lisa Hoashi The thing that makes me. Well, I think it really feels my work a lot and as the like as seeing how we can get into those positions of just being like, so miserable and it's so hard to change. And I I guess I just feel like a lot of times the trap that we get into is that we start blaming ourselves because it's not working. But actually, we just really need someone to just like, get us out of that situation. It's just like a bad situation. Just get out of here. But we have to be like our own heroes and like, pull ourselves out, you know? And it's like at that moment when we don't have, we don't, we don't have the confidence, the energy. And so it just anyway. It is it is heroic when you are able to do that, you know?
[00:43:41] Jennifer Dillan Yeah. And when you have those people in your life, that is such a gift to have those people say, you need to get out, girl, go.
[00:43:48] Lisa Hoashi If not, you
[00:43:49] Jennifer Dillan know, it's not you. And I would meet people who had left the organization say, Yeah, that place is a pressure cooker. And you know, when I left, I'm like, Am I even doing a job? Because it's that much easier? You know, they were still working full time. They're like, but so it did. I was like, I had normalized a situation that was hurting me, and I didn't have anyone in my life right at that moment saying, You need to get out, you need to get out. Matter of fact, people were saying, Oh my gosh, you're the creative director. Wow, you must be so proud. That's amazing. And you make six figures and you have incredible benefits and you could never leave that. You know the golden handcuffs, you know? It's kind of, you know, like even when movie stars or someone like I'm out, they tap out because they're like, I don't want it and people can't believe it, because who wouldn't want fame and fortune? I'm not saying it came from fame and fortune, but I did feel lucky. I felt fortunate. Wow, am I really going to leave this or look this gift horse in the mouth? And I had to reach that low because I didn't have someone in my life telling me, You need to get out. I did. I did kind of hit bottom, and that gave me the impetus to be like, I got it. I got to get out.
[00:45:07] Lisa Hoashi Mm yeah. Yeah. I mean, yeah, the golden handcuffs is like, you know, there's still. You know, it's just like, yeah, it can bring so much self questioning when you go to a party and someone's like, Oh, you work there. It's so amazing. You're so lucky and you're just like, Am I the most ungrateful person in the world? Or like, where is the reality? Check here? And it can be hard when you're on your own sometimes to like, do that reality check.
[00:45:39] Jennifer Dillan Yeah, yeah. And I did. And I I felt the positive benefits immediately. So that kept me that that was easy to keep going the moment I did it.
[00:45:52] Lisa Hoashi Hmm. All right, John, for our final wrap up question, please. I would love for you to like specifically speak to the people in our audience who are like at that 50 year old like sort of point and offer some of your thoughts to them. So the first question is, what do you wish that you knew before you made the leap?
[00:46:15] Jennifer Dillan It's exactly what you and I were just talking about. What I wish I had known before I made my leap was that I would feel freer, more positive and less stressed in my life and that more energy I'd feel like myself again. I wish I had. I wish I had known how good it would be, and I would have done it earlier.
[00:46:37] Lisa Hoashi And what was maybe one of the most unexpected things about your leap are they came from it?
[00:46:43] Jennifer Dillan Well, one of the most expected things that I hadn't reckoned with yet was that, like we'd mentioned earlier in the in the conversation, is that my identity was so tied to it, I felt I had to let that go. That was I didn't realize it when I was getting ready to let it go, and I was like, Wow, I, I'm going to need to let this old self go so I can kind of bloom into this new self. So that was an unexpected and somewhat difficult thing. And then the other unexpected thing was how alive I felt in the new role learning new things. I thought school would just be drudgery and hard, and it was just going to check the box. But it really was very inspiring and connected me to people I'm still connected to today, professionally and personally, and ignited a love of learning that I didn't know I had at 50. So that was a nice gift. Nice silver lining. Awesome.
[00:47:43] Lisa Hoashi And then what would be your advice to others who are considering this? Similarly?
[00:47:48] Jennifer Dillan I would say that it's super scary to make a mid-life career change very scary for all the reasons we've spoken about, but there's kind of no better time we have. As I mentioned, the experience, the wisdom, the resourcefulness and support system often not always to make it happen. And there's no expiration date on being happier. I think that it's a fallacy that people in the middle in your middle age can't reinvent themselves and those whole 40 under 40 lists. You know, I really wish there was a 40 over over 40 list or over 50 list for everyone who has the guts to make a leap, make it happen and then transform their life at between, let's say, forty five and 60 is extraordinary and beautiful to watch and exciting, and allows everyone that gives everyone permission to know that they're not stuck for the rest of their life in a job they're unhappy with.
[00:48:53] Lisa Hoashi Well, thank you, Jim, and I would love to hear about what you're doing right now for work and how can people be in touch with you?
[00:49:03] Jennifer Dillan Yeah. So now I've started my own company called Wild Hair Development. It is really to facilitate these two projects that I have going. Personal projects. And then I'm doing some consulting on the side, too. That's exciting to me. I want to be doing more of what I really love and this allows me to do that. And if people want to connect with me, I'm on LinkedIn. That's the best way to get a hold of me, and I will respond to messages and. Any other questions people have happy to?
[00:49:36] Lisa Hoashi Awesome, thank you. Well, it's been a really inspiring conversation and I love hearing that this live to like a new raw and new industry has then led you to like yet another leap of starting your own business.
[00:49:52] Jennifer Dillan Yeah, thank you. And I'm excited to see you growing your business. It just from our past friendship. I just loved working with you so much and watching you flourish in your business too has just been incredible to watch and very inspiring. I can see that you're really thriving.
[00:50:10] Lisa Hoashi Thanks. Yeah, it is incredibly satisfying to be able to to start to refine what you learn about yourself and how you want to work right and to be able to like, I mean, what I really like from your story today is just hearing about, like how you took these things that you were like, I'm not going to repeat this. This is how it's going to be different next time. I'm, you know, I want I choose this for my next work, and I feel like that's been something that I've learned to is like, I want to be intentional about that. I can have control over like the various elements of my work and how I work, so that it's it's something that's really supportive of me and the life that I want to have. Yes, it's so important.
[00:50:56] Jennifer Dillan Yes, let's have more of that.
[00:50:58] Lisa Hoashi Yes, absolutely. Well, thanks again for being with us. It's been a pleasure.
[00:51:04] Jennifer Dillan So fun, Lisa. Thanks for having me.
[00:51:07] Lisa Hoashi Thank you for listening to this episode of Leap like me. There now is the time. If you're listening for the first time and you got some inspiration and ideas for your own life and work to hit that subscribe button so you don't miss new episodes and leave us a five star review. You can listen to leap like me wherever you stream your podcasts, and the video recordings are also on YouTube. Head on over to Lisa Variety.com to get the show notes, which also includes transcriptions. If you're at your own crossroads moment in life and are ready to get clear on your next direction and want to work with me as a trusted outside perspective who can guide the way, then head on over to lisahoashi.com/catalyst-coaching. That's a wrap for this episode. Thank you for listening, and stay tuned for more.
