How To Love Your Career (And Help Your Team Do The Same)

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Becca Banyard: What if you could wake up every morning excited to go to work? Many of us spend the majority of our waking hours working, but how many of us truly love what we do? Is loving our jobs even relevant in a market where lay-offs are so common?

Welcome to the People Managing People podcast. We are on a mission to build a better world of work and to help you create happy, healthy and productive workplaces. I’m your host, Becca Banyard.

My guest today is Jen Dary, founder of Plucky, a company that provides leadership coaching and new manager training that essentially helps you learn how to work with other people. Jen shares from her own journey of finding career fulfillment and the lessons and tips she learned along the way. So stay tuned to learn how you can love what you do and help your employees do the same.

Hi, Jen! Welcome to the show.

Jen Dary: Thank you so much, Becca. Hi everybody who’s listening. Nice to meet you all.

Becca Banyard: It’s so great to have you here today. Usually when I have a guest on the show, it’s my first time meeting them. But we actually met a little while back when you were a guest over on our sister site, thedigitalprojectmanager.com. And I loved your conversation with Galen, so I really wanted to have you on the show.

So thanks so much for being here today.

Jen Dary: Thanks for having me. It’s my first time on a sister show. So that’s very interesting. I assume you have a lot of listeners who crossover.

Becca Banyard: I think we probably do. Yeah.

So I’d love to just get to know you a little bit better. Just before we dive into our topic today, we’re gonna be talking about the trade-offs that employees make in order to have a job that they really love. But yeah, let’s talk about you to start. Tell me about yourself, what you’re passionate about, and also just how you started your company Plucky.

Jen Dary: Sure. So I live outside DC in Arlington, Virginia. I have two sons who are 7 and 10 right now, and we have a puppy and a cat, and I have a husband. And Plucky is the company that I started almost 10 years ago.

Later this fall it will be 10 years in. And Plucky is a leadership coaching and consulting firm. So I would say a little over half my time is spent one-on-one coaching, that’s either with leaders or emerging leaders. And then the other chunks of my time, I teach a class called “So Now You’re A Manager”, usually do that about four or five times a year.

That’s for folks who are within their first three years of management, let’s say. And then I have some random manager products that I’ve invented. And I do a lot of teaching in other spaces too. Either lunch and learns or small groups or, spaces like that. And part of why I founded Plucky was I was internal at an agency in New York and I was handling employee development there. And 10 years ago, the market was really different in terms of what we understood professional development to be.

So nobody had a coach, it was like, oh, you have a prof dev budget, buy a book. It was like, oh, okay. And today, actually, thankfully, the world has changed a little bit and so there are a lot more supports available to folks internal at an organization. And you also see different budgets for each individual and that becomes almost like a type of benefit.

Yes, you get healthcare here. Also, you get access to go to a conference or find a coach. And so, I’m actually glad that coaching is more mainstream today than when I started it, even though of course, I’m not as subversive, shall we say, as it used to be in 2013.

Becca Banyard: Amazing. Thanks for sharing a bit about yourself and your company.

So we’re in this market where a lot of individuals are unfortunately getting laid off. So what does somebody do in the times that we’re in if they don’t love their job?

Jen Dary: I think there’s sort of an algorithm going on in an employment situation. So on one side you’ve got a company who has, let’s just say a role and they have a budget that they can pay for that role, a timeline for when they need that person to start, or assuming they’re already employed there, there’s like a situation there.

We have this poll to fill and you employee fill it. And on the other side you have an employee who has a motivation, a skillset, probably also a budget that they need to fit into. And so in this way, there’s a collaboration or an agreement of sorts between those two, I guess I’ll say like entities or presences, right?

A company and an employee. And in ideal cases, those things match. And things happen. Companies evolve and people evolve. So there’s, it’s possible that companies might evolve and say, uh-oh, we hired you as a junior and actually we don’t have any anymore. We’re not doing that product anymore, so we can’t employ you anymore. Goodbye.

Or the employee might say, thanks for the fun times. I actually wanna go make double the salaries of where else buy. And so this sort of series of coming together and then departing is actually just to me what career path is. And at any given moment, one of those sides of the coin might say, this is no longer working for me, for a million reasons, unpacked what I just said.

Right now we’re in a situation where companies are doing a lot of initiating of that sort of detaching, but last year it was exactly the opposite. And last year everybody was leaving because they were getting better jobs or more interesting jobs. But last year we were in a situation where it was very different, and last year it was majorly a candidate’s market, especially in tech.

And so you had people all the time just interviewing and going different places. The reason I bring that up is that this question of what do I love to do at work? Or do I love my work? That is relevant all the freaking time, regardless of how the recession or market is going on. And so there’s gonna be ebbs and flows from my point of view of when you might take a risk to maybe better authenticate or better align yourself to find work you love.

And there will also just be times of life when you need to pay your mortgage. And so you sit tight. And so right now we happen to be in that ebb of sort of the story of things, but I don’t think this will last forever. And I certainly think people can still love what they do, even in the minutiae of “how could I love when I’m doing this” hour.

Love is also a really big verb here, right? How could I appreciate or be fulfilled by, or enjoy or collaborate with or something. So I think that’s always available to us in a way.

Becca Banyard: So for somebody who’s in that space who’s I just wanna love what I don’t love what I do right now, what is it that I wanna do and how do I achieve it? Where do they even start? What do you recommend they do?

Jen Dary: Oh my God. Well, this is the soul searching question, right? Who am I in the world? I think this is why I started Plucky. Just to circle back for a second, I had my first son and I went through postpartum depression and helpfully, it allowed me to ask every day, why am I on the planet?

What’s my thing? And for people listening, you might be more on the sort of spiritual side of the spectrum, more faith-based, or you could be on the other side, which is more, let’s say mathematical-based, but it doesn’t really matter either way. You can say, why am I on the planet? Either what has my purpose been laid out for me?

Or based on the math of where I went to school, what I studied, how much money I need to live? What does that spit out either, right? I think every person should ask this question, why are you on the planet? And then we should go to dinner and discuss because it’s the only thing that matters to me in talking to people.

I think there’s so many things that try to convince us of answers to that question, including what our parents did or expectations from society, or what our professors, encouraged us towards, or what gender you are. There’s lots of things that have assumptions about that, but only you, the individual is gonna be able to say this, when I do this kind of work, I like resonate, and I vibrate almost because I love it so much.

Filling its energizing. And that can never sort of be applied from the external. So I guess the first thing I would say is you should probably ask yourself that question. If you have a trusted network of friends or coworkers or a coach or therapist, you could ask them, Hey, what do you think? And as long as you have a healthy emotional boundary there where you don’t have to agree with everything they say, then that can also be a fun data collection to sort of do.

But in order to find your way to a job you love, you can’t authentically answer that unless you’ve asked that question to yourself. What do I love? What resonates for me? And you might look back at previous roles or parts of previous roles and said, when was I most fulfilled? Was it when I was customer-facing?

Was it when I was quiet and working at my desk alone? Was it when I was solving problems every day? Was it when I was leading people around a campus tour during college? Like what of the, those sort of stories and anecdotes come alive for you as times when you were really fulfilled? And then what’s the pattern?

Were you always with people? Were you always traveling? Were you making no money but mission-driven? Were you making all the money? People have a lot of data inside them that we forget to look at, and so I think that’s a big part of that question asking too.

Becca Banyard: So good. I’m curious to know just a little bit more about your own journey of soul searching that led you to Plucky. What did that look like?

Jen Dary: So I have an exercise that I make all the people who do my manager training do, and I call it jobs and verbs. And it’s based on literally a journal entry that I did when I was going through this postpartum depression and wondering. So I have everybody write a very long list of every job they’ve ever done.

Kind of what I was just talking about. It can include like babysitting in high school and volunteer jobs, whatever. Next to that, you write your favorite part about that job, starting with a verb. So a classic example I give is that I worked at a farm over the summer in college and my favorite part was teaching kids how to milk cows.

So you’ll notice that I’m starting with the word teaching, which is a verb. So you go through and you do that, and then at the very end you calculate your verbs and you scrape kinda like three most common verbs off of that. My three most common verbs were leading, connecting, and writing. So what I knew is if I decided to go back to my job, which I was out on mat leave for, maternity leave for, I should advocate for responsibilities that would allow me to lead, connect, and write.

And I wasn’t really outta the ballpark of that. I was already very much, that was part of my role, but I knew that those would be fulfilling verbs for me and actions. If I decided to take a different job, I should look through job descriptions and job recs that allowed me to do those three things: lead, connect, and write.

If on this random off chance I started my own company, it should probably be one that invites me to lead, connect, and write. So I say that because again, anybody listening could certainly do that exercise, but it allows me sometimes if I’m having lower energy or feeling a little burned out or whatnot, I can always say, oh, hold up.

Hold up. When’s the last time I led? When’s the last time I connected and when’s the last time I wrote? And in those ways, it helps revive me. Again, I feel like this whole conversation is me revealing some kind of like mathematical algorithm, even though I’m an extremely social, emotional person. But I think sometimes it can be hard to hold on to the emotional or soul-based or, squishier things.

And for me, some tangibility is helpful. So when I can track back to those three words in particular, it helps me feel set up for success in appreciating what I’m doing and the opportunity I have. And obviously that has, turned into a business that I’m really thriving with.

I will, as a side note, say that last year was a particularly just fatiguing year for me. And by the fall I was, I just something wasn’t good and I couldn’t figure it out. And I think part of this is, almost 10 years in, you say like, I don’t have a boss. Nobody’s laying out a career path, nobody’s increasing my salary unless I do that work.

Where am I going? And so I admit that to everybody listening very freely that a decade into my own business, which is dream job, you love everything. It’s so shiny, but you still can have those questions. And so this year, I always work for Plucky four days a week. And this year, my fifth day a week I’m writing and I’m in a fiction class right now and doing all kinds of really fun essays and things like that. And that has been so fulfilling and I’m in a much better head space than I was, let’s say, six months ago.

Becca Banyard: Oh, that’s so good. I love to hear that’s what you’re doing. And your exercise sounds like such a really practical and useful exercise, not only to find what you love doing, but also to continue to love what you’re doing, like to have that longevity in your career. So, yeah, so cool. Yeah, I love that. I’ve never heard of that before.

So I’m curious because, with our jobs, there’s so many trade-offs that we can make. Like we can look at financial stability, we can look at wanting to have career advancement. We can look at just the market and what jobs are available, work-life balance, the way that we feel like, do we love our job?

Are we fulfilled? So what trade-offs have you made? What things have you looked at and said, actually really that’s not important to me, or that is, and how do you balance that with loving what you do?

Jen Dary: I will use my situation as an example, but there’s obviously some principles underneath it.

So what I kind of subscribe to is the idea of seasonality when it comes to, well, pretty much anything but we’ll say career right now. There are gonna be different seasons of your career and you’re gonna be hungry for different things. And so by and large, earlier in your career, you are probably looking for experience and maybe a social component to the work.

Maybe you go out with friends after work and social life. And then eventually the season might evolve into something like, okay, I actually need just some stability here, or I need money to pay for, my family or whatever. And none of the answers to those seasons is incorrect.

It’s expected behavior that a person is going to need something different from work across their whole lives. You’re just not gonna always need the same thing because people are complex and they change. For me, when I look back at the last 10 years of Plucky, it has been an intricate balance as a parent. Because remember, I started Plucky literally at the same time I had a baby when my son was 10 months old.

That’s when I started Plucky. So I have not really known Plucky without being a parent, and so I’m sort of the primary person who had stayed home a couple days a week with kids and whatnot. And a really specific example I can give you is that when we had moved to California from New York when my son was about 18 months old. And when we first got out there, we were like, okay, let’s get a daycare three days a week.

That’s what I had been doing, and we only found daycare two days a week. So for about eight months, I ran Plucky two days a week. And then I got him in, and then I ran Plucky three days a week, and then I had another baby. So I was off from Plucky for, you know what I mean? And so, what I needed from Plucky was certainly space to experiment and some kind of income, but my evolution in my career was really hand in hand with my evolution as a parent.

And for folks listening who aren’t parents, that can be a lot of different things. Family that you’re caring for, volunteer opportunities, like we all have something we’re balancing, right? And so, that for me at least when my kids were that young, work was hand in hand with parenting. Now luckily my kids got older and then I could travel a little bit more, and so work became also this like exciting time for me to shed across the country and spend three nights somewhere teaching a class.

It was my alone time. I got to see some friends, go out to dinner a few times, so work for me then was really social based too, and I loved that period of time. And these days, I think work is stable. And also it’s like where I experiment, I’m like, what should exist in the world? Why don’t I make a pack of cards to help people mentor each other?

Okay, let’s try that. It’s like an art project in a way. Like what else should exist? But I’m not a moron about it. I talk to people all day. I coach them, I teach them. So I’m listening for threads underneath what would be a helpful thing in the world. So, I’m not just like creating art for art’s sake.

But again, also it’s providing some stability so I can write and try my hand at some other creative work right now. So again, for those listening, I think it’s a seasonal thing and I’ve needed different things from Plucky, even though the content of my work is largely the same, always has been.

Becca Banyard: Yeah. Thanks for sharing. I’d love to look at it now just from more of a leader’s perspective and get your thoughts there. What responsibility do leaders have in creating an environment that people love to work in, but also helping their employees love their jobs?

Jen Dary: Yeah. I saw your question ahead of time on that, and I was thinking a lot about it this morning.

I think I, it’s interesting to replace the word love with do. So how do leaders help people love their work? If we replace it with, well, actually, how can leaders help people do their work? I don’t actually think you can make anybody love anything, right? That has to be agency on your own. So like I was saying earlier, individuals need to self-identify as what is motivating to them and what they enjoy doing.

I have so many people right now that would just really love to be able to do their jobs without politics or hitting a ceiling or having some kind of support from a manager or senior leader who isn’t like too busy all the time. You know, who actually needs to come and not handled, just literally manage, literally come, teach, coach, experience, walk through something, address conflict, be transparent.

Like all the freaking leadership things. We have a lot of leaders, especially at the very top, who probably realistically sometimes really don’t have time for that kind of work, but also as sure as heck, avoid it as best they can because that stuff is hard. I know it. I really know it. So, I think employees would love to be able to do their jobs, do the jobs they were hired for.

They’re talented people. They wanna come in and they wanna be allowed to do it. And sometimes doing your job means change, which is really threatening to an organization or sometimes they’re leaders. But I do really think, especially in like a post-ish Covid World where we’re a lot remote, like people are having different presences of work and home in their lives, and I think people are finding a lot more fulfillment outside of work these days.

So let me do my job and then I’ll go home and I’ll love the whole thing. It’s kinda like I wanna relieve leaders simultaneously of needing to motivate and inspire people all the time. Instead just show up and do the work and people are gonna love you more for that.

Becca Banyard: Such an interesting perspective. I love it. So I’m curious then, what do you recommend a leader do in order to help their employees do their job and be able to do their job?

Jen Dary: A really great question to say in a one-on-one would be, What are you blocked by? What can I unblock for you? Or what do you need access to that you don’t have right now?

That might be information, that might be Jira whatever. What do you need access to that I have access to? Or yeah, just like honestly asking those questions and being present and being a resource instead of just, I don’t know, a person on an org chart. So in order to help people do work, you want to make sure that they can be efficient and that they have channels through which they can get communication and you know here, relevant information.

Just like you look at a job description, you say, okay, great. What would this person need? You don’t even have to have the human in front of you. Just say okay, literally what would this person need to do good to do well at shipping this on time, making sure the customer’s happy, da.

You don’t even need the person in front of you. So that might be a fun takeaway for some people listening is before you even hire someone, take your job rec and next to it say, what would I need to do as a manager to support this job going well? And actually that would remove all of the nuance of well, we hired but they’re a little picky about that.

Okay no. We’re talking in a vacuum. What would a manager need to do in order for this person to be successful? And sometimes it’s a little cleaner even to think of it like that.

Becca Banyard: That’s so good and so immediately applicable. I love it. So we’re gonna wrap up shortly. What advice do you have for someone who is currently struggling to find a career that they feel fulfilled in? What’s one piece of advice you can leave them with?

Jen Dary: One of the most common things that people approach me about, who I don’t know, or actually also people who are in my network already is how can I become a coach? It’s like “the thing”, how. Oh, I wanna become a coach, and maybe you should, right? I’m not trying to say people should not. But sometimes late at night, I think about this and think, does everyone want to be a coach?

You could get a whole psychological armchair thing about the power that someone might perceive that, oh, someone’s the wise old person who coaches everyone. Although I hope you can tell my personality at this point that I don’t see myself in that holy way. But I actually think more often than not what people are responding to is some kind of perception that I am in the right job, that I am a fulfilled, confident person, and what lights me up and happens to be the work that I’m doing, and it’s such a foreign thing.

How often do we actually meet someone who is exactly aligned and plugged into what they should be doing? It’s not very often, and so sometimes I think people mix up my job with actually like my alignment, if I can say it like that. And what they really want is that shininess of enjoying what they do every day.

So it’s I’m gonna go back to the beginning of our conversation here, but I think you have to ask yourself, what is your alignment here? What are you on the planet to do? And in some cases it might be the content of the work. Like I’m a project manager, I’m organized, I love shipping stuff across the finish line.

I feel so proud when we finish something. And in other cases it might be a population, I love working with children. Or it might be a mission, I love working in the sciences because I wanna fix dementia. There’s not only one template for figuring out what you love, but based on the idea that you are a gift to the world.

Cuz it’s actually hard actually to have a baby, and anyone out there who is thinking about or trying it’s like real hard. The odds are not with you. So if you arrived here on the planet, what do you gotta do with it? And I think that question feels a little slippery and Oprah esque, but I literally don’t care.

It’s the only thing I like talking to people about. Exaggerating a little, but I think we should spend our time on.

Becca Banyard: Amazing. Thanks for that. So, to wrap up, I just have two questions for you that I ask all of my guests and I’d love you to weigh in. The first is, what do you think is the number one thing that keeps employees happy in the workplace?

Jen Dary: I think my answer is people. If they like who they work with, it goes a lot easier. And I don’t just mean personality, but facility to communicate, ability to bring up something hard. Not being afraid of people. The humans are the work, right? It’s like we took our dog to dog training and the lady joked that it’s actually human training, but the dogs are in the room.

It’s human training, right? We’re all in that. That’s who we have to work on and with and build skills around. It’s not the code or the design. It’s the people that are complicated or amazing.

Becca Banyard: Okay. Next question. What do you personally need as a leader in order to be successful?

Jen Dary: For me personally, I need ventilation systems.

So I need supports who are not, I mean, my company is very small, but I need supports who I do not work with so that I can be like, oh my God, that happened today. Right? Like I need someone who is a safe space for that. And I always coach my leader people to vent sideways and up. So you can vent to peers and you can vent upstream, so to speak, but don’t vent down.

So if I’m a manager to be tangible, if I’m a manager and I’m having a frustrating conversation with a different department. I should not bring that to my one-on-one with my direct report and be like, man, you know what design is doing over here? I mean, that is so not profess, right? Clean it up, people.

Become an adult. A strong leader is gonna have some kind of resource exterior to work where they can just be a child for a minute, be mad and it doesn’t have impact and ripple effect on everybody else that you work with. And that is very true for me too. I’ve had seasons of my life where I had a coach, seasons of my life where I had a therapist.

Sometimes I just need a walk. Like taking good care of myself and my own mental state is biggest ingredient for success for me, for sure.

Becca Banyard: Such great advice. Jen, it’s been such a pleasure having you on the show. Thank you for joining us. For people who want to get in touch with you or follow your work, where can they do that?

Jen Dary: So my website is beplucky.com. Maybe you’ll have show notes to stick that in. And we’re on Instagram @bepluckster. LinkedIn, just you can look for Plucky or for me. And yeah, and also just to throw it out there, you can just email me hello@beplucky.com. I love just, hearing what people are up to and I’m very friendly so you don’t have to be intimidated.

I’m not the wise old mystic coach. I’m just the normal lady coach.

Becca Banyard: Amazing. Love that. Well folks, thank you so much for tuning in. If you like this episode, please leave us a review and subscribe to get notified every time we release a new episode. And if you wanna stay in touch with all things HR and leadership, head over to peoplemanagingpeople.com/subscribe to join our newsletter community.

And until next time, have a great day.