413: Defining Your Ideal Role Based On What Success Looks Like For You

Jackie Yerby 00:02

So I will be the policy director for the Urban League of Portland. And you know, we work on civil rights issues for folks of color with a particular emphasis on the African-American community. My heart is singing at the prospect of doing mission driven work that feels really important especially right now.

Introduction 00:28

This is the Happen To Your Career podcast, with Scott Anthony Barlow. We help you stop doing work that doesn't fit you, figure out what does and make it happen. We help you define the work that's unapologetically you, and then go get it. If you're ready to make a change, keep listening. Here's Scott. Here's Scott. Here's Scott.

Scott Anthony Barlow 00:52

What happens when you have a job that seems prestigious, most people would love to have it, but you can't stand it?

Jackie Yerby 01:00

The work culture was pretty toxic. I didn't feel good about the work. So my first best day was the day that I decided I needed to leave that job.

Scott Anthony Barlow 01:10

That's Jackie Yerby. She is what, the kids today would call a boss, she's had a series of various prestigious high impact roles in public policy, although not all of them are fulfilling. And this is a fascinating aspect of career change in itself. We have shared a lot on the podcast about looking past what other people do to change careers or what other people think is fulfilling and trying to identify what you want, what you find fulfilling, even if it makes other people say, "really? are you sure?" Well, it turns out that Jackie's career brought her into some high powered circles of people who had very specific ideas about what it meant to be successful and Jackie felt like she had to meet their standard. Keep your open during this episode for Jackie's explanation of how she escaped other people's expectations and focused on what actually made her feel fulfilled. Here she is, explaining where her career began.

Jackie Yerby 02:13

So I have a Master's in Public Policy from the Kennedy School of Government at Harvard. And I studied Health Care Policy. To the extent, there are minors by, kind of minor concentration was in international affairs and security. But I knew that I really wanted to focus on domestic policy. And I went to grad school in the 90s. And so that was when Hillary Clinton was working on health care reform. And I've always really been concerned about the lack of access to health care especially for folks who have been marginalized which includes lots of communities of color. So that's been something I've always really cared about and, you know I tried to do other things, but I kept being called back to health care policy. And as you can imagine, I mean even in the 90s going to grad school is expensive. And you know even with scholarships I took out a lot of loans. And so when the Blue Cross Blue Shield Association said, “hey we want to interview you.” And I'll just pause and say like you know they post in our career center. I looked at the job posting. I'm like, "No way. That's not me. I'm not qualified to do that." And they said, “No. We actually want to talk to you.” And so I was flattered. So I went to that on-campus interview and they invited me to Chicago to interview. And several folks within that organization had actually gone to the Kennedy School. And so, I didn't have to play my degree to them. And we hit it off and it was amazing. And then I ended up being in a horrible experience.

Scott Anthony Barlow 03:44

In what way?

Jackie Yerby 03:45

The work culture was pretty toxic and it was the kind of thing where I did form friendships within my department. But it was kind of like, in spite of all the energies trying to keep us apart, and I remember I had this one really good friend who, we would have lunch together on a regular basis, we were sneaking out, you know, we're like meet by the elevator or meet down stairs. And we think that we were conducting like a clandestine affair because like we didn't want the boss to know that we were becoming such good friends 'cuz we might be talking about them, you know.

Scott Anthony Barlow 04:25

Oh, no.

Jackie Yerby 04:26

And I would say, my first best day... oh, let me just say to you, I didn't feel good about the work. I didn't feel like I could stand behind the work.

Scott Anthony Barlow 04:35

What was the work at that time?

Jackie Yerby 04:37

Yeah. And you know it was a consulting type work. And I didn't feel good about what we were selling. I also wasn't forming deep connections in Chicago. And like for the 14 months I lived there, I didn't spend a single three day weekend there. At that point I had the ability to just kind of like hop on a plane at a moment and used to be able to do that. And so I would fly to Washington D.C. where most of my friends were. Or I would fly to New York where my sister and brother in law live. And every time I went to D.C. I also traveled to D.C. once a month on business. I always felt like I was flying back into my life. And so really striking. So my first best day, was the day that I decided I needed to leave that job. And that was about seven months in. And it was like this huge weight was taken off my shoulders. So then I started looking for a job in Washington D.C. And so this is 1995. There's no Internet. There are no cell phones. This is back in the day when a friend of mine, friend of a friend, who has since became my friend had two Rolodexes. And I sat in her office in D.C. and she went through her Rolodexes and she said, "Get in touch with these people. Use my name." And then I read the letters that I have printed on that really nice paper that you used to buy. And I nailed them. And then you know then I called them on my landline to make appointments and then I set up all these appointments and then I took time off of work. I don't forget what I said I was doing, it really detailed clandestine meetings in Chicago because there was the possibility that I actually might see my boss in Washington D.C.. But it was amazing actually how much being able to use my friend's name, opened a lot of doors for me and this is my first experience with doing informational interviewing. And I was really struck by how generous people were with their time even in Washington D.C. Through that experience of networking looking for a job, I actually interviewed for a job as a legislative assistant to then candidate Senator Joseph Lieberman and other finalists. And they hired somebody had so much more experience than me. That's fine. But I asked a colleague at the Blue Cross Blue Shield Association if she would be a reference for me and she was. My colleague based in D.C. and I didn't get that job. But then she called me and she said, "I have a job for you. Do you want to come work for me?" And the answer was, "absolutely yes." And so I ended up going to work for her. And it was night and day from my experience of having worked with the folks and she got liked the leadership in Chicago.

Scott Anthony Barlow 07:15

The culture in one section was completely different than the other section.

Jackie Yerby 07:20

And also I mean, just I felt like the boss I had with D.C. was warm, comfortable in her own skin. But I remembered, like my office was right next to hers. And had that been the case in Chicago. Like it just... it would have been untenable. And my new boss would say, "hey we haven't talked in a while. Let's go across the street and get coffee." And I'm having this moment of like, “Oh no, no. This is a different boss. It's okay”.

Scott Anthony Barlow 07:48

Oh dear, flat boss flashbacks.

Jackie Yerby 07:50

Oh my gosh. Yeah. And I felt like this kind of you know like a wounded puppy for a while. So I was in that job for four years doing legislative policy work focused on what was going on the state legislatures, got to travel around the country, got to meet lots of interesting people. But I got tired of living in Washington D.C. And I also felt like I was plateauing and not that I have this like this huge aspirations to be important and famous and whatever. And I feel like I'm on the East Coast where I spent a lot of time like status counts for a lot and I remember watching TV, so I was 30 and were watching TV on a Sunday, watching the Sunday news programs with the Washington post spread around me. And George Stephanopoulos, he was 37 at the time, was on TV and he was counselor to the president. And here's Jamie Rubin, was an adviser to Madeleine Albright, also 37, and I remember thinking, "in seven years, is that what I'm going to be doing? I don't think so." Not much less my life takes a really different path. And I just, you know, get a turbo charge. But I was also like that's a not, I don't actually want that life. It felt like unless I go down that path I'm not going to be seen as successful in this environment. Also I'm originally from the West Coast, I'm originally from California. I live in Portland Oregon now, and I really missed trees. And it's not like I'm somebody who goes hiking and camping all the time. But like when I worked in downtown, Portland, I could look out my window and I could see three park blocks in downtown that have dove birds, you know. In Washington D.C. there was rock creek park which I would occasionally ride my bike through on my way somewhere or walk with a friend. But as a woman, it didn't feel safe to be in that space by myself. I remember I was also talking with friends like "hey, let’s go camping this summer." And I think I did that for three summers in a row. We never went camping. I wanted to move to a place where like nature felt a lot more present and also where people valued things other than work. And so back in '97, I just was starting to feel really bored in Washington D.C. and also at that time the whole Monica Lewinsky scandal. Actually, I feel bad for calling it the "Monica Lewinsky scandal." 'Cuz she's actually turned into this really amazing and graceful person. But that was going on.

Scott Anthony Barlow 10:23

The book “Clinton scandal”.

Jackie Yerby 10:24

Clinton scandal. Thank you, thank you. And so the environment in D.C. just the atmosphere just felt particularly toxic and I just thought, I got to get out of here. So like I said I've been traveling a lot, have met a lot of people around the Blue Cross Blue Shield System and really hit it off with somebody who was the chief legal officer for the Blue Cross Blue Shield company in Oregon. And I was in Portland to do a presentation to the leadership team and he said, "If you're ever interested in working here, let me know." I was like, hey and I really liked Portland from the time that I came to visit. And so I followed up with a Christmas card with the like, "Hey, I'm actually kind of interested." and got, you know, the like, let's talk. And then he called me, I think in January and said, "I have something that you might be interested in." And I perked up and I said, "What is it?" And he said, "Ethics and compliance officer" and I literally said, “are you nuts?” And the field was really new at the time. And my experience of interacting with the ethics and compliane officer at my company who had, was the chief auditor and became that was, I mean he didn't have great social skills and so if I saw him like, I'd walk in the other direction and not that I had anything to hide. I just wasn't a comfortable person to talk to. Mark, the chief legal officer and I kept talking and he explained his vision for the job and that it wasn't to be that cop, sort of busting people, for behaving badly but it was to set a tone. To help create an ethical culture within an organization. And the thing that I loved about it was that there was an opportunity to learn and grow on the job. And I specifically asked that I've never done this. And lots of people have never done this. So I have ideas but you and other people I will be interviewing with can't ask me what I have done because I haven't. And that was kind of funny, I flew to Portland for a day and a half of interviews. I was like, "we need to have breakfast because I need to make sure that people understand again like, who I am and what my background is." And he's like, "absolutely." And I don't know that anybody else interviewed for the job. So you know, I had this like marathon day and a half of interviews and I got off the job. And they totally lived up to their commitment of letting me learn and grow on the job.

Scott Anthony Barlow 13:01

That's awesome.

Jackie Yerby 13:02

Yeah. And I got to work with a great team of people, the other ethics and compliane officers in the other states where this company did business at work. And so Idaho Washington side, yeah, Idaho Washington and Utah. And it was the kind of thing where we didn't know each other before but we just really clicked. And it was the kind of thing where the kind of work we were doing it was really important that we trust each other and felt that we had each other's backs and we did. And we never became cynical about people which is how I was able to do that job for 11 years. There's some pretty stressful times and there's some very stressful investigations.

Scott Anthony Barlow 13:10

So then, that sounds great in terms of that lines up with so much more than some of the other pieces that we've talked about previously in terms of, hey it's a better location that matches up with what you really want, different people that aligned with what you really want, a cause that in a lot of ways, you could get behind that made sense at the time. So what ended up changing from that, that caused you to move on?

Jackie Yerby 14:11

So I switched jobs within the company. I became the Sustainability Program Manager and part of it was like our leadership changed. And I didn't so much care for that person. Smartest guy in the room consistently mansplain and also I just felt like my team had changed. So I was ready to move on. And the CEO, who was the person that originally recruited me to come work with the company, he had gone from the Chief Legal Officer to CEO, he created this position, the Sustainability Program Manager position, and I really care about sustainability. So this idea of triple bottom line that it's not just about the environment but it's also you know how to make economic sense and have to be good for people. And that just really resonated with me. So actually I was the second person in that role. The first person became a really good friend of mine, he's still a good friend of mine. And it was a growth opportunity for him but not a passion for him the way that it was for me. And he was just appointed to it. And I remember being really disappointed about that, that I didn't get a chance to raise my hand. And so I reached out to him and I said, "Congratulations. Then you have to let me help you." So I did. And so I became part of the unofficial team. And when it came time for him to move into another role, I became the most obvious person to step in. I had to interview for that. I think there was maybe one other person so I got the job.

Scott Anthony Barlow 15:56

Let's go back to that what you just said for just a moment because I think that is something that is not the first inclination for many people. But I think it's really important. And I just heard you say that, hey like you saw this sort of situation that wasn't... maybe wasn't necessarily desirable because it sounds like you wanted to be able to raise your hand to be able to have an opportunity at that role at least. And what has a tendency to happen for many people is, they will just write it off as, you know... didn't have an opportunity, so I'm just going to, you know, I'm just not going to worry about it or didn't have an opportunity and I can't believe that guy got the job or any number of other things other than what you did in what you did was say, okay, I'm going to... I'm actually going to continue to be involved in this in a really positive and productive way. And then not so long afterwards, it created an opportunity for you and that is, unfortunately, I think the polar opposite of what many people will do and what I've even done in the past in certain cases too. But what I've found is that when you do exactly what you did where you look at that potentially not great situation and turn it into something that really is really positive and productive and actually really legitimately helpful for everybody, then it almost always comes out so much better in ways that you can't anticipate. So, nicely done, first of all.

Jackie Yerby 17:30

Thanks. So I got that job.

Scott Anthony Barlow 17:32

Yeah.

Jackie Yerby 17:34

And then I realized how much harder it was than the job that I had which was actually pretty hard.

Scott Anthony Barlow 17:39

Careful what you wish for, I suppose right?

Jackie Yerby 17:41

Yes, totally. And my friend, Dan, who had a job and then became my boss told me that it was like pushing rocks uphill that if he moved the program an inch forward in a day that that felt like success. I think him stepping into that job coincided with the start of the great recession. And so then it became about like waste and kind of productivity and, you know, streamlining processes which can certainly be a part of it but that's not a part of it. And to me, it never felt like there was a heart or a vision behind it. And I tried to articulate one like, hey let's get really involved around like childhood obesity. And here is how it affects the triple bottom line, you know, let's talk about how we're spending so much money on drugs for kids for type 2 diabetes that we wouldn't expect to see until decades later. And kids are really hard to treat because they're noncompliant, right. And then you know let's talk about food deserts and neighborhoods without sidewalks and parks and places for kids to like play in their own neighborhoods. And then there's no movement. And for that, you know, there's the environment he's in. And then the people he's about like, again, how it's impacting people. And I would tell them, I would have shot that around the organization and people would work in the right way. Is this about recycling? And I’m like, I am a master recycler. I actually really care, I’m a geek about this stuff but I just felt like I couldn't get traction. And when I came to realize from talking to other peers in our organization is that organizations that make things, that have a tangible inputs and tangible outputs like get sustainability a lot more because when you can use less material, less inputs you were saving, you were obviously saving money and you can tell a great environmental story about it. But in a service company, it's harder for that to pencil out, kind of hearts and minds to see, hey this really matters to employees and let's talk about employee retention.

Scott Anthony Barlow 19:53

It's not as pressing and in front of everybody in the same way. Unless it is already deeply ingrained into all of the other leadership messages and all of the other elements. So I totally get that. So what was the breaking point that caused you to decide to move on?

Jackie Yerby 20:12

Well I was laid off which is actually fantastic.

Scott Anthony Barlow 20:17

It worked out perfectly.

Jackie Yerby 20:19

And I mean obviously it's a hard thing but I was so ready to move on. So that was at the end of 2014. And in 2015, I started looking and this is like, I haven't looked for a job in a long time, probably not really since 1995 when I was looking at Washington D.C. and I didn't know how to look for a job, right? So I had like a one page cover letter that you know you can actually say a lot and cover a lot of ground in one page. And I didn’t know that I was supposed to parrot their words back to them in the application or the posting back to them so that their computer flagged it. And I was like, "oh, she's got this because she used our words." So I didn't get interviews for things because I didn't score, because I didn't understand their algorithms. So I'll just say it like, I do a lot of volunteer stuff. And I dove into volunteering to help save the LGBTQ community center which was in danger of closing. And I went there because I had the time, frankly, and also like a came from the board of basic rights in Oregon which is a statewide LGBTQ rights organization. And it was a great because I got my mojo back. It was like I had something unique to offer in this group. And I felt valued in a way that I hadn't for a long time. So I'm super grateful for that experience but also, I mean, I made some really great friends out of it and the Q Center the LGBTQ community center is still here. It's arising. It's the kind of place that when we are going through this which was like a weekly two-hour meetings that turned into four-hour meetings for six months. It's the place that I think, we all hoped it would become. But again a really great experience for restoring my confidence in myself and what I have to offer folks.

Scott Anthony Barlow 22:35

I think that's really important though, Jackie. What has a tendency to happen to a lot of people is just what you described where they're in a role that, for all intents and purposes, is kind of sucking the life out of them, right.

Jackie Yerby 22:48

Yes.

Scott Anthony Barlow 22:49

In one way or another. And it looks a little bit different for everybody but you know I was just having this conversation with my wife last night actually because she's considering a transition from what some of the things that she's doing, she's been involved in a lot of different pieces. And one of those, she actually really loves what she's doing but doesn't really love the situation around it. It's sort of, in the same way, sucking the life out of her. And in order to really make a successful transition you kind of have to find ways in order to bring that mojo back, as you're putting it. And I think that that confidence that has a tendency to come back with that is really really important. And it's one piece of the process that a lot of people I think don't think about or don't realize. And you know we see it all the time as we're working with people where we have to create a situation where they're bringing that back and then do the rest of the steps.

Jackie Yerby 23:46

Well, you know, was my experience of starting to work with you guys, but before we get to that I'll say, so in 2015, I did some consulting. I did some like equity work, like racial equity work within the environmental movement. And I really enjoyed that and felt like this really spoke to... it felt important and valuable. So I did that. And then I also got recruited to work in a climate change campaign called The New Oregon. And I got recruited to be a faith organizer cause I'm a person of faith. But I loved doing that, didn't pay well. I was contracted for a certain number of hours. It felt meaningful and important. That was also the summer that the pope came out with his people on climate change among other things. So you know so I got to talk about the pope a lot you know and obviously it was in the news. But I just... it was like, it just felt great to be working on something that I really cared about. And that drew on a lot of things that I had to offer including my faith. I was like, I just... I don't know that I ever felt that. And so it was great. And I thought I wanted to do nonprofit work and in fact I think it's really important I serve on a lot of nonprofit works. I found I wanted to be an executive director. Actually a friend, somebody I have a ton of respect for said, "hey you know you should think about this one." And I was completely flattered like that this person would think of me in connection to this role at his organization that they were working at at that time. I made it through the interview process and then I was one of two finalists. But there was this long sort of lag between the last interview and when they made the offer which kind of soured me on the experience and I just, I remember joking with them that it sort of felt like junior high like I would totally date you. But you know I want to date this other person. You don't love about that. And I'm not gonna state that organization. But it was an organization for which I volunteered in the early 2000s when I first arrived back in Portland. So even though I hadn't stayed connected to it, it was special and important. What I realized when I got in there was just how all consuming the job is being an executive director is 24/7. I would dream about it, I would wake up in the middle of a night like gasping about like something I was stressed out about. I would think about it when I was gardening, you know, it just... it was hard to turn off. So the other thing is that, I did not love the job and I think I realized pretty early on that I didn't love it.

Scott Anthony Barlow 27:00

What didn't you love about it?

Jackie Yerby 27:03

I didn't love that being the Executive Director is pretty lonely and isolating. And I am somebody who likes working with the team. I like bouncing ideas off other people.

Scott Anthony Barlow 27:17

You're very collaborative. Every conversation I've ever had with you. It feels more like a collaboration than it is, I don't know anything else than a conversation.

Jackie Yerby 27:27

Yeah. Thank you. So yeah, I value collaboration and I value like making decisions that the lowest level that makes sense. And so you know people would ask me for permission for things and I'm like, you can make this decision you know and not like, 'hey don't involve me.' But it was like, well actually you can handle this and I'm happy to be a sounding board. But ultimately, you're the subject matter expert, you get to make a decision. And I felt that that wasn't valued. And in fact there were some folks that I worked with who I felt like, took advantage of that. And were actually kind of manipulative in terms of like, I know more than you, sort of made me or tried to make me feel like small and vulnerable. So it just didn't feel like a safe environment. I like challenges. But this was just a lot more than I wanted to deal with or something that I didn't love. I didn't feel valued and I didn't think that I could thrive in that environment. And that was reinforced by some feedback that I got... that gave me permission to say, "I'm done. I'm out of here." And I still reflect on that idea of needing permission to go as opposed to just deciding, this isn't working and going. I left that job almost a year to the day. And it is interesting. So I had actually interviewed for another Executive Director job at that time, the bicycle advocacy organization and I was a finalist. And I heard that I was the choice of the staff and I heard from a number of board members that they were really excited about me. But they went in a different direction which is probably good for me because I really don't think I want to be an Executive Director again. But I'm really passionate about active transportation and I had a lot of ideas for this organization. But anyway, so I was already like making plans for what would come next and not coming from a place of being anxious. But just as you know there are these opportunities. And I applied for another job doing equity and inclusion work which is a passion of mine at Central City Concern which works of people in recovery from substance abuse and alcohol abuse, great organization. And so you know there were things that were happening. And even though like I got right into that I wasn't feeling anxious about it. And I also knew that I needed some time to decompress after I was laid off in 2014. I realized how much, even in Portland, people identify with their work. And so people like, "What do you do?" You know and I'm like "oh I'm a consultant and I'm doing this training." And this time around people would say, "What do you do?" And I'd say, "I don't." And I would say like with a certain amount of glee. And I think it was in November, a friend of mine said, "you don't work for money." And I'm like, "okay, I don't work for money. I actually have stayed very engaged with different nonprofits that I'm part of." Yeah, I don't sit still well and so it's not been like oh I have breath and relaxed. I've definitely decompress from the last job. But I have been applying for things here and there, a number of government based equity and inclusion jobs. And get an interview because I had learned to play that game, right? Of like, I'm parroting your words back at you. And in some cases, you know I would get a second interview. And in some cases, I wouldn't, which didn't feel great. And then there was a job that had a community engagement equity component to it working for the Bureau of Emergency Management. And I was actually really excited about that. And for folks not listening from Cascadia, the last major earthquake was over 300 years ago and where the schedule is every 300 years and so we're trying to do and it's going to be bad. And so I care a lot about emergency preparedness. And here was an opportunity to work with communities of color around emergency preparedness. I'm really excited about it. They were excited about me, and they chose somebody else. And that's at the time, that's when I first connected with Happen To Your Career, because there was this job that I really wanted. And then you know they were super lovely about, "hey we think you're great, but..."

Scott Anthony Barlow 32:16

You're second place.

Jackie Yerby 32:18

And so in Portland, we have this thing called Mac's list, it comes out on Tuesdays and Thursdays. And Tuesdays when you know the job listings are. And usually I would go straight to the job listings. But on that day, I happened to read, you know what else is going on. And that's when they mentioned the webinar that you did the following day. I was like, "okay I'll sign up for this. I'll check it out." And I was in that headspace of not feeling confident. Like why can't I close the deal. Like, don't you know what I have to offer?

Scott Anthony Barlow 32:52

Don't you understand me?

Jackie Yerby 32:55

I'm starting to feel desperate and lacking confidence and starting to go down the path of the things that you folks talk about not doing which is just like, oh my gosh, I need to not just look on Mac's list but I need to look on idealist and all these other places. You know I need to apply more and I need to... I was starting to feel that scramble and I should say, like I have financed this year of not working. And I'll say like people ask me if I was going to do consulting. And I said "No." I like working with other people. I like working in infrastructure, organization has some infrastructure. I didn't want to be hustling for work. I have borrowed money from myself to make this happen. And so not looking forward to tax time next year. But I was fortunate and that I worked in the private sector for many years, I built up a very healthy retirement fund and I've got an amazing financial planner who has been taking care of me through my retirement resources for the last year.

Scott Anthony Barlow 34:00

So let me ask you about that really quick because I think that that is important. And you and I have had conversation already about this, so I know some of the behind the scenes and everything. But why did you feel like, that was the right decision for you? Because it's probably not the right decision for everybody necessarily but why was that the right decision for you?

Jackie Yerby 34:20

So, I guess when I felt like I had the wherewithal to do it that I could afford to do it.

Scott Anthony Barlow 34:26

Yeah.

Jackie Yerby 34:26

When I was laid off at the end of 2014 and I first started working with this financial planning group who have just taken great care of me. One of the questions I asked was, "Should I be saving for retirement this year that I'm not working?" And they said, "if you didn't save any money for the rest of your working life, you would be fine." I mean that was a huge relief to hear because even when I was working there wasn't a lot in the way of retirement benefits. And so I just I felt like really confident that I was sitting on this comfortable nest egg which I still need to be responsible. So I've been making it work and it's been fine like learning to ride the bus again and like walking around and just noticing and being present. And it also really changed my relationship with time because I have to think about how long it's going to take me to get somewhere. And so I'm actually not, I mean there's still a certain amount of rushing but there's also a certain amount of like waiting and reading and noticing. And I actually really like that and I hope I can hold on to that even after I get back into the car owner.

Scott Anthony Barlow 35:40

Not to go too far in that direction. But I thought that was really interesting too because when we went and we lived in Paris for a month and were using, we were riding public transportation all around or when we were in London for a period of time doing the exact same thing. It was really really nice because I mean I live in Moses Lake Washington, and we don't have great public transportation. We don't have like, if I want to go anywhere, then it's about five miles away. And it's a hike. And I kind of actually loved that. I loved not having a car and not driving anyplace along those lines because I'd become used to it. But it really does, to your point, change a relationship a bit with time in that way.

Jackie Yerby 36:26

Well and also for me, also changed my relationship with people, you know because you get all kinds of people on the bus and sometimes I'm on a bus late at night because I like to work at a brewpub, you know less than a mile away from me. And so I'll hop on the 11:02 bus and you get some really interesting people on the bus at 11 o'clock at night. And it's just made me, in some ways, more patient with people you know like people have their own thing going on and I'm just not going to move my seat because of whatever. So the financial peace. I just... I felt like I had the wherewithal to do it. And I'm really really grateful about that. The other thing I'll say, I'm not a penny pincher and, you know probably would be better off if I were in a lot of ways but I didn't like change my standard of living a lot in the last year I'm not working. So again I felt like I could afford to do that. We'll see how I feel like, I said next tax time when I'm paying taxes and penalties on this early withdrawal that I've been taking to fund my life. But yeah and I just... I mean it gave me the headspace to not just take anything and certainly not take something I hate. And I guess the other thing too was coming out of a space of just knowing how soul killing that could be, to be in a space of like, I'm just doing this because I need to, you know, and it's hard to find like what you want to really be doing when all of your energy is being sucked away with just sort of going through the motions.

Scott Anthony Barlow 38:13

So that's a really interesting take because essentially what you were doing for all, intents and purposes, was you were financing your headspace and the regrowth of your soul as you were. And I think when you're looking at it like that, that really changes how you're looking, it changes how I look at value. But I think that having talked to you then because I got to have a pretty early on conversation with you after you found us, just as we were I can't remember totally how it happened but you and I, we found ourselves on the phone. You were telling me a little bit about this and it really did sound like it was the right thing for you based on everything else that you just shared with us. Like I don't think you would have gone down the same path and the same way, had you not created that space for yourself.

Jackie Yerby 39:04

Yeah, You and I like the first after I signed up, after I decided I wanted to do it. I was supposed to have a coaching call with somebody else. And then you hopped in and you're like, "is this okay?" I'm like, "yeah. it's totally okay." And I really appreciated that first conversation and it really set a very positive tone for my interactions with all the Happen To Your Career Career Change Bootcamp folks said that, "you're real, you're warm, your human, you listen amazingly well." Like I was talking to Caroline. She got like, "Hey so I heard you say that..." And it was like listening sort of below like behind the message, behind the words in ways that was almost spooky. So when you and Caroline asked me like, "what did I need from you" and what I needed was a confidence boost because at that time my confidence was flagging. And so going through Career Change Bootcamp and you know doing the different exercises like the strength thing which I kind of got bogged down in that. But I loved the piece about asking people like when you have us reach out and ask people to comment on our strengths. And I reached out to a bunch of people. And you know I figure they have good things to say about me but the consistency of those messages was great.

Scott Anthony Barlow 40:30

What did that do for you? Just curious.

Jackie Yerby 40:33

Well it's also for me, again, made me feel like, hey I actually have something to offer here. And just like reconnected with that. At that time when I'm like, nobody is wearing me. So that was that piece. And I said the other thing that was really really valuable was what you had is doing module one of creating a support network which you know I had once sort of informally. I mean I have one. But the formality of it, this is what I'm doing, would you be part of that. I almost didn't do that part and I'm glad that I did. And what having that support team made me do was I checked in with them at least every week, two weeks and a half and said, "Here's who I am." And you know some days it was, "I'm excited about this interview." And, "hey I'm really getting a lot out of this Career Change Bootcamp" and some days it was like, "Oh my God. I didn't get a second interview. I'm super stressed." And it was really great to have these folks like offer encouragement and support. So whether you're participating in a Career Change Bootcamp or not to have that and to have more than one person as part of that and doing it in a really, I don't wanna say formulaic way, but a more formal way. I found incredibly helpful today. So another thing that happened was in mid March, I started working with you in January, and in mid March, I think I was working on two job applications and the way that I applied for jobs and there were government jobs, the way I apply for jobs as I do a ton of research and you know go all over like this organization Website. And I had a coaching call with Caroline and she said, "don't apply for it" and I was like, "okay." And I didn't apply and I felt great. I also stopped looking at Mac's list. I focused on the Career Change Bootcamp and other things. And it just felt like this huge weight came off of my shoulders and it was interesting like at first it was hard to not look right? Because we're so programmed to like oh my gosh this email, showed up in my inbox and got all these things, I should be looking for this. And so I made myself not look. And so there was a job that I'd applied for, the Oregon Food Bank that I'm super excited about. Didn't I get a second interview. So again still not in the... I'm not looking stage. We're also still starting to have that, going back to where I was in January of like, "maybe I should be looking, maybe I should be like scanning all these lists because something's not happening." And in Portland and other cities as well there's a group called a civic organization called the City of Portland. I was a member a long time ago, recently re-joined, a friend of mine the Executive Director. Another good friend of mine was the Chair of the Board, she just started off of that. And the programming is really great. And so I was at the City Club and it was the state of the city. So another good friend of mine is Portland's small two degrees of separation was interviewing the mayor as the second part of a two part state of the city. And at that thing, afterwards I went up and was talking to people and saying hello to friends. I talked to the woman who will be my boss, who was the CEO of the Urban League of Portland. And we've known each other for years, where finally we hug each other when we see each other. And she asked me, 'how I was doing at the job I used to hold.' And I'm pretty sure that I told her that I'd left. But I reminded her that I'd left and she asked me, 'what I was doing' and I said, "I'm not", again with that like you know, 'what you do' "I don't." And she said, "why didn't you come work for me? I could use you. You should have come work for me. Come work for me."

Scott Anthony Barlow 44:29

Why aren't you here already?

Jackie Yerby 44:30

Yeah. It was basically like that and I was like "Hey." And she said, "We should talk." And I said, "Well I've applied to this other job" and she's like "Don't go work for them. Come work for me." And so you know really flattered by that. I think she is amazing. Like ever since she's originally an Oregonian. So native Oregonians are a big deal as in, you know most of us are not native. So she's a native Oregonian which was working on the East Coast, working politics, came back to Oregon a few years ago. And so I've followed her career. Her predecessor in the Urban League is a good friend of mine. And every time I've heard her name, Nkenge Harmon Johnson. Every time I heard her speak I thought, "Wow. This woman is amazing. She says what's on her mind. She doesn't dance around, she holds people accountable. She's a strong strong woman, strong voice, and a really great and important voice for the African-American community." So just nothing but admiration for her. So anyway there's the whole 'come work for me' thing. And about just as I was thinking 'oh I should follow up with her.' So this was 10 days after we had talked. And I think I was working on some other stuff. She emailed me to say, "hey you know legislative session is coming up, well, next year. And our state of Oregon report and we could really use you as a policy director. Come work for me." And it was more like elegantly stated than that. That was the gist of it. And I was like "Wow." And felt good and excited about it. Like it was around that time that I also realized that I wasn't moving forward with the food bank. And actually felt okay about that. That job would have been largely an H.R. job which were they were pulling equity people in culture. And I definitely could have done it. But it's not like my sweet spot. And you know the food bank is great. It does amazing and important work. But the thought of being a public policy space working on racial justice issues for, especially the African-American community, just feels really resonant right now. The other thing is Nkenge and I follow each other on Twitter. And on Twitter most of my tweets are pretty political. So you can get a good sense of what I care about and what I think about, and I'll just pause and say, before I started at the non-profit, it was right around the time that a group of people occupied the Malheur Wildlife Refuge, bird refuge in eastern Oregon. I had a lot of feelings about that. And I was vocal about them on Facebook. And one of my friends, an old friend, wrote me a note and said that she was worried about me being able to find a job because I was so political. And we're not friends anymore because that me being true is really important to me. And I'm fortunate in that I don't come from a family where it's awkward to have converse... like we care about the same things. Right? So I don't have to worry about not making mom or dad bad or you know, actually I do have one aunt who's, you know.

Scott Anthony Barlow 48:14

There's always that one aunt.

Jackie Yerby 48:15

Yeah, you know. And so it was just... it was like, you're telling me that I need to check myself in order to be palatable to other people. And I was like, that's bad.

Scott Anthony Barlow 48:29

That's exactly the wakeup call that could be needed but in the opposite way.

Jackie Yerby 48:34

Yeah. And so the fact that like one of the ways that Nkenge knew me was through like how I engage on Twitter like that told her something about me. And also I think through that and other avenues like one of the things that she talked to me about was she's like, "I need somebody who can help me hold people accountable, hold people in the community accountable for their commitments to the people we serve." And I love that. I can be tough, I can be fierce. I mean I want to be collaborative, right? But I'm also just like "yeah, we're not doing that" or you said, you need to do this. I need you to do this. And so I'm really excited to be in a role that values that and where I will get to use that. So yeah it was one of the things where there wasn't a formal interview process. And it's interesting because another good friend of mine, who was actually the board of the food bank, asked me about the Urban League's process. And I started telling her. And her response was, "Well that doesn't feel very equitable." And I was like a guppy and like "um..." And what I said was the equitable process is, I think I told you this Scott, the equitable processes that I participated in, felt almost dehumanizing. Like we're making it so fair. Like we were scoring you. We were not responding to ... like there's no asset in the room.

Scott Anthony Barlow 50:15

It's gonna be so equitable we're going to take all the humanness out of it.

Jackie Yerby 50:21

Yeah. It was horrible. And I'm trying to figure out how to give them that feedback and I think it's based on the false premise that we're going to strip relationship out of this. Right? And I was talking to another friend and I would say, my really good, both of these women are white, which feels important to say. And the second friend I was talking to said, "you know the Urban League's equity journey looks very different than the food bank's equity journey or most organizations equity journey. Like they don't have to work as hard to hire folks of color as an organization that isn't that diverse and doesn't have that history." I was like, I wish I had those words when I was talking to my friend. And the other thing that comes to mind is, I was at a friend's high school graduation a couple weekends ago. And this is a young friend who I've met him when he was four years old when his family arrived from Democratic Republic of Congo as refugees. And my church was part of the group that sponsored them. And so I've, you know I've known this kid for 14 years, and he is amazing. He's going to Georgetown in the fall. So I went to his graduation. And their keynote speaker was a graduate, I think she graduated four or five years ago, and she's giving advice to the graduating class. And I felt like she could have been giving advice to me you know someone a lot older than her. And one of the things she said was, "take advantages of opportunities that present themselves. So if the elevator door opens, get in. Don't feel like you have to go find a ladder and climb that ladder, get in the elevator." And I was like, "ugh! That is what I needed to hear." Because I feel like you know again out of this idea of equity and fairness. Like, oh no no no we need to make this hard. We need to go this way to create these you know perceptions of fairness. Anyway it'll be interesting to see. Like once I'm in that role, how that's perceived internally as well as externally. So I'm still trying to figure out how to navigate that. But most people have shared the story with her, like oh my god that's amazing and you're going to be great, you know?

Scott Anthony Barlow 52:43

I agree, as it turns out. Let me ask you this though, because here's what I know from our team being involved with your journey is that, this wasn't always easy and there was a lot going on behind the scenes. And even though it felt like in the end, if people were just looking at the end result, it felt like this happened very organically, there is a lot that took place in between in order to actually get to hear. So I'm curious from your perspective now that you're looking back, what do you feel like was the hardest part of going through that. Because it had you accepted or had you at anything, you know occurred differently had you not... does it made the decision to not apply for some of these roles and not worry about some of all the minutiae that was out there that probably wasn't a great fit for you. Then potentially you could have ended up accepting something completely different in a different place that might not have been a great fit. So what do you feel like looking back was some of the most difficult parts for you?

Jackie Yerby 53:53

Sorry, like most difficult about like being part of the bootcamp or just in general?

Scott Anthony Barlow 53:57

No, on this process.

Jackie Yerby 54:00

I mean, I think it was the... you know, there were definitely times that felt anxious, right? There were definitely times that again, like I would get excited about something, you know it's like you fall in love with the possibility of a job. And then you know you go into that interview and this is why you want me. Until you talk yourself into something even if there might be reservations about it and then to not have that. So there was, you know questions about my own judgement. And you know, what am I lacking? And I'm talking to friends who are also looking and you know not being hired for things and that feels like a common thread. And so trying to like weather that, you know and it again, my support system helped, Caroline helped. And you know like kind of staying connected to Happen To Your Career help. I was listening to a podcast. And I would just kind of like take a deep breath and be like, "Oh yeah that's right. Okay. Yeah." 'Cuz it can feel overwhelming and kind of lonely you know and then to hear about other people's experiences and be like, "Oh that's right. This is what this feels like." And there's another side, right? Yeah. So I mean... so I think that emotional roller coaster felt very hard. And also and I kept having to remind myself to find something that I really wanted to do and not just something that I could do. And Caroline kept like parroting that back to me like, "Well, you said this. So you know, remember this." Because there were definitely times when like, I could do that. And you know when I think about the different government jobs that I applied for and you know easy to say on this side of it when I didn't get it and I've gotten something else. But I don't know I have an idea of a good bureaucrat. I don't know that I would function well in that system and I, you know, works for a very large bureaucratic organization for a very long time and was successful most of that time, so I can navigate that but I think I'm done.

Scott Anthony Barlow 56:40

You don't want to in the same way.

Jackie Yerby 56:42

Yeah. I think I'm sort of done, like toning it down for somebody else. And you know having to navigate like big systems and silos and stuff. And I'd say every organization has their idiosyncrasies and their dysfunctions and so I'm not you know I'm not expecting everything in Urban League to be like, amazing. But hopefully a lot more nimble. And I feel like I'm going to get a lot of... have a lot of space to be myself, to bring like my best whole self and my connections built up over 18 years of living, 19 years of living in this community and the services I work. And that it's work that I really care about. I feel like it's work that needs to be done and I'm excited that I get to do it. So yeah, so I am... one of the things that I feel like, you guys do really well is to keep us focused on what's right for us and the way that I told that to friends to whom I recommended Happen To Your Career is a lot of times applying for a job is, 'Here's a round hole, you're square peg so let's get out the sandpaper.'

Scott Anthony Barlow 58:13

I feel like your next tweet should be what you said earlier that, "I'm completely done toning myself down for everyone else."

Jackie Yerby 58:25

And yeah. So I feel like you know Happen To Your Career is all about like what fits you, what do you need, what do you want. And I love that piece of it because a lot of times I feel like what we want like that we're being... we're asking for too much. Let's say, "I want this." And you guys are like, "No. that's actually really important. So can you find that thing that you want? Because if you don't, then you might be in a place of like it's a slog again." So it was helpful to have that sort of North Star of what do I want. And I should say this was... I mean, they definitely you know crawled all over the Urban League website. I'd rather see a black Oregon report. Talked to my friend who was the previous CEO but I didn't... I haven't researched it the way that I did the other ones. So how does this feels like a leap of faith? But again, I have a ton of respect for the Urban League CEO. I'm excited that I get to work with her. And I'm excited that she sees things in me based on having known me for years and observe me for years that I can benefit the organization. So again I feel like I get to be who I am, to bring like my best full self to this work in service of an important social justice effort. So yeah, I'm super excited about that.

Scott Anthony Barlow 1:00:16

That is amazing. And congratulations, by the way.

Jackie Yerby 1:00:20

Yeah, thanks.

Scott Anthony Barlow 1:00:21

And you know one of the things that runs through my mind as hearing you say all this and talking through the entire thing here and now is, it almost feels like in some way that you're going to such great lengths to do so much research. And I would never discourage people from preparing or would never discourage people from... just going in with no prep, no research, not understanding whether something is likely to be a fit necessarily. But it almost feels like a lot of those cases the more that you go into it, the more that you'd find ways to justify that this could be a fit for me. And I almost feel like afterwards, you know, having seen the full circle that I think it is less of a leap of faith, regardless of how it feels like outside looking at it it seems like it is actually less of a leap of faith based on all of the really important things are very aligned. And you have to like go find those things on a website someplace that it was said so that you could say them back to them or whatever else right.

Jackie Yerby 1:01:29

Right.

Scott Anthony Barlow 1:01:30

And I think that in itself is real. That is the important thing. So nicely done. Because that's not easy.

Jackie Yerby 1:01:39

Thank you. You know though, I think about... I don't necessarily want to say serendipity, you know but I think about it like having gone to that city club and you know not surprising that both of us would be at a Mayor's like State of the city address. But one of the things that, like the coaching that I've offered to other people is about being present. And you know about, I don't like to... I mean I don't like the word networking because I think it implies, like something that's transactional. And over the years like I have built a lot of relationships across a lot of different sectors and issues. And so I had my 50th birthday party last year, I invited tons of friends over. And one of my friends whom I knew from a project where they used to work and I was on the board, and they are a person of color, they said, "wow this crowd, like is truly intersectional." I had church friends and I had LGBTQ friends and I had friends from the different nonprofit, friends from like my biking circle. And yeah it was just a really interesting fun mix of people. And so I've developed a lot of relationships and friendships over the years. And it's not quite came from a transactional space but it feels like it has served me well in getting to this point. And I say this was someone who was an introvert. But introvert means I'd rather talk to someone one on one or in small groups than you know to be like interacting with larger people. So for example at my birthday party, I didn't actually want to talk to anybody. I wanted them to talk to each other or that I would party to them for like 2 minutes at a time. But I don't know, I just... you know I put myself out there. I talk to people. I got to know people. I think Nkenge also talked to like her predecessor about me and imagined she talked to other people about me. And yeah and I feel like that played an important role here. And so I've tried to encourage people to find the things like the city club that feel comfortable, that aren't just about I'm looking for a job. But, hey we have here shared interests. What did you think about that panel? And not just like I'm looking for a job and you work there. Although you know that works too, but that feels different.

Scott Anthony Barlow 1:04:37

It does feel different and I think the different feeling is a big part of it. I've got one more big question for you. No pressure or anything. But you know you've gone through this entire change, it's been quite a journey over the last year. And there's been so many elements of it that we've just talked through. What advice would you give to people who are kind of on the beginning of that, where they have realized that, hey I'm in the equivalent role where I know that I don't want to do this anymore and I am thinking about making this change and the right on the precipice. What advice would you give them when they're back there?

Jackie Yerby 1:05:17

Yeah. So I, you know I see... I usually reads comments in a Facebook group of Career Change Facebook group and I realize people are in lots of different spaces and have different situations, right. And I would say, "get out of the situation before it crushes you." And that's really strong language. But I think about the situation I was in before I was laid off where I felt like I couldn't hold my head up in terms of like, how I talked about the work that I was doing. And I wasn't excited about the work that I was doing, excited about like the kinds of contributions that I made which doesn't make for a great like, 'hey you want to interview me for this job.' I just I felt low energy or not. And so I'd say it's really hard, I mean certainly for me, it was hard to be in that headspace to think about what I wanted to do next. And I guess it also goes back to confidence and so I'd say, if you can get out of the situation before your confidence is gone and before you feel desperate about finding that next thing, so that's number one. And you know I think about like a bit earlier the climate change campaign that I worked on, and it was like, wow this is what this feels like when you believe in and love what you're doing. And I'll say, I mean, I worked for a large corporation for 16 years. And I believed in what I was doing most of the time that I was there. And you know believed in a lot of what the organization was doing. But body and soul we're kind of integrated. And so when I had that experience of working on the climate change campaign, I was like, "wow that's what feels like." It's hard to go back after that. And I think it was probably in the back of my mind when I was working... when I was running a non-profit. But it was really clear early on that I did not love that job. And so you know, and I get it. Like there's some people who, a job provides them the resources to do the rest of their life and to do things that they love and that's not where they want to put their energy, I get it. My friends are people who are listening to Happen To Your Career podcast and going through the Career Change Bootcamp, are those people that they're looking for meaning in work. And so I think to hold out for a place where that meaning feels like it's there and then the other thing too is that definitely been in situations. And I felt like this about sustainability job is, I'm going to make it meaningful. And it was certainly meaningful to me, but I struggled to make it meaningful for the organization. I wish I had realized that earlier and had decided to move on earlier when I still felt like my head was, I was holding my head high.

Scott Anthony Barlow 1:09:09

Most of our episodes on Happen To Your Career, often showcase stories of people that have identified and found and take the steps to get to work that they are absolutely enamored with, that matches their strengths, and is really what they want in their lives. And if that's something that you're ready to begin taking steps towards, that is awesome. You can actually get on the phone with us and our team, and we can have a conversation to find the very best way that we can help. It's super informal. And we try to understand what your goals are, where you want to go and what specifically you need our help with. And then we figure out the very best type of help for you, whatever that looks like and sometimes even customize that type of help. And then we make happen. The really easy way to schedule a conversation with our team is just go to: scheduleaconversation.com. That's scheduleaconversation.com and find a time that works best for you. We'll ask you a few questions as well. And then we'll get you on the phone to figure out how we can get you going to work that you really want to be doing that fits your strengths, that you love, and you're enamored with. Hey, I can't wait to hear from you.

Scott Anthony Barlow 1:10:33

You probably heard that you need to say 'no' to more things. We've all heard about drawing boundaries. And then if we're too busy, well, guess what, it's just our own fault. All we need to do is say 'yes' to less things. Which sounds easy in theory, and it's nice to write down. And it's great to read about on a blog post. However, it's much harder to do in practice, in reality.

Greg McKeown 1:10:57

All of a sudden, as COVID hit the, you know, like a quarter of the US population, almost literally overnight, had been asked to believe something like involuntary essentialism. Yeah, not unkindly, we were told, go to your room, and don't come out again until you've had a good thing about it. Like, it's a global teenager, we went and have had to think. And I think there's not almost not anybody who hasn't asked whether they said it in exactly these words or not. But the spirit of it is, what's essential now? All the things I could focus on, what should I focus on? All these things I no longer control which things even matter.

Scott Anthony Barlow 1:11:45

That's Greg McKeown. He's a huge advocate for pursuing less. What he refers to as "essentialism". His writing has appeared in places like New York Times, Fast Company, Fortune, Huffington Post, Inc. Magazine, lots of other places. And he's among the most popular bloggers in places like the Harvard Business Review and LinkedIn influencer scripts, averaging over a million views a month. Oh, also, he's the author of "Essentialism" which I read a while back and thought, hey, I have to get Greg on the podcast. So many months later, he's here to discuss the disciplined pursuit of less and where the idea of essentialism actually began. All that and plenty more next week right here on Happen To Your Career. Make sure that you don't miss it. And if you haven't already, click Subscribe on your podcast player so that you can download this podcast in your sleep, and you get it automatically. Even the bonus episodes every single week, sometimes multiple times a week. Until next week, adios. I'm out.