The Messy Middle: What Career Change Actually Looks Like Before You Have the Answers

Happen To Your Career - Meaningful Work, Career Change, Career Design, & Job Search

The episode explores the 'messy middle' of career transition through the personal story of Holly Dixon, who left a 20-year legal career withou

Key takeaways

• Holly Dixon transitioned out of a 20-year legal career after experiencing burnout and health challenges including type two diabetes.
• The 'experimentation' phase involves structured trials such as mediation certification and organizational development projects to gather useful information.

Main topics

• Career experimentation
• Managing burnout

Notable quotes

The experimenting isn't the detour on the way to clarity. The experimenting is how clarity gets built.

Conclusion

Career change is often a non-linear process of trial, error, and emoti

Transcript preview

Speaker 1 (0:00) I don't like to argue and I don't take sides. So obviously law school was like the obvious choice for me, right? She went Speaker 2 (0:06) anyway, and then she spent two decades in the legal field. I Speaker 1 (0:09) would come home from work and I would put my pajamas on and turn on Netflix. And that is all I wanted to do. Speaker 2 (0:14) This went on for years. Speaker 1 (0:16) I don't think I identified it as burnout until after I left and had some time to be like, oh. That's what was going on. I just knew this didn't feel like me and it felt awful and it was getting worse. When Speaker 2 (0:28) she finally took a hard look at what she was amazing at, she almost missed it. Speaker 1 (0:32) Everybody can talk to people. I really had to reframe like, how is this a strength and how valuable that actually is. Speaker 2 (0:41) Holly left without her next job lined up. And now she'd tell you she's never been more herself than right now. This is Happen to Your Career. Most people let their career happen to them, falling into jobs by accident, staying longer than they should, and wondering if this is really all there is. But a few people decide to stop settling and do something different. This podcast is for you to take control, get intentional, and design your career to fit the life that you want to build. Real stories and real research so you can stop waiting and start making it happen. I'm Scott Anthony Barlow. I want you to meet Holly Dixon. She got her law degree, and not once in her career did she ever want to argue a case. She actually decided not to get her law license and then spent five years working at the Innocent Project, particularly with people who had been wrongfully convicted of something that they didn't do. Later, she worked in a federal defender's office in both Tennessee and then in North Carolina. Now, fast forward 20 years. An entire career invested in law. But she knew now... this wasn't where she wanted to spend any more of her time. So she decided to leave with no next job. And after giving four months notice, which by the way, Holly co-created an exit plan with her boss, which is an entire section of this episode just Speaker 1 (2:00) by itself. Speaker 2 (2:01) She went to, actually, you know what? She still hasn't landed, which is the entire reason we're sharing her story. On this show, we typically will share crew change from start to finish, you know, entire episode that is built around the whole story. That said, what we hardly ever do is look at the snapshots in time that happen on the in-between. And that's exactly what this is. Well, Holly's going to walk you through is the messy middle, as some would call it. We call it experimentation, which is a critical part of designing a life and a career that you really want to build. And in Holly's case, this meant designing experiments to create rapid learning, volunteer work, a mediation certification, an organizational development project, and a few short-term jobs. Now, from the outside, this looks like trial and error, but it isn't. Every one of those experiments gave her useful and specific information. The experimenting isn't the detour on the way to clarity. The experimenting is how clarity gets built, iteration by iteration. And you can't get there by thinking harder or taking any single assessment. By the way, when Holly and I first started having our conversation, she was in the middle of telling me that she's still happening to her career, which for a podcast called Happen Your Career is a pretty good first line. Speaker 1 (3:23) I'm exploring life and I'm doing a lot of like volunteer work in areas that I had always been interested in, but sort of never allowed myself to get into. So still exploring. I'm a wanderer, as I say, a gypsy at heart. Speaker 2 (3:37) I think one of the things that is really sort of fascinating about your story is that you spent a couple of decades in the legal field, right? I think the twist here is that you went to law school and then you didn't get your law license afterwards. So sort of walk me through why you chose to pursue law in the first place. And then, you know, what happened through that time period? My Speaker 1 (4:00) childhood really influenced. what interested me or what I thought interested me as far as careers. So I grew up with a lot of unsafety and not being supported. And there was a period of time where we had a lot of contact with law enforcement because of someone that my mother was dating at the time. And it was a very unsafe situation. And so my first kind of inkling of what do I want to do with my life was, oh, I want people to feel safe and supported. I'm going to. be that epitome of like safety for people. And that, that stuck with me for so long, but there was sort of this pull back to what I thought was the law. I loved the black and white nature of what I thought the law was. And I loved like being able to know what's right and wrong. Again, this is what I thought it was. And I ended up, I went from working with families to being promoted in that same nonprofit agency into HR. And while I was doing that, I had a set nine to five during the day, like Monday through Friday schedule. And so I decided, well, I'm Speaker 2 (5:04) going Speaker 1 (5:04) to go to law school. So I started going to law school part time in the evenings and ended up moving out to California to finish law school. I knew before I left that I was like, oh, this is not for me. And the reason was because I got to see sort of the inner workings of the law. So I was obviously most interesting in criminal law. That's really the reason I went to law school. So I thought I was going to be a prosecutor, like I was going to keep people safe. But then I got to see how our system actually runs. And I don't mean that to be a dig. I just mean for me, it was not what I thought and it was not what I wanted to be a part of. I knew that it wasn't me. Well, first of all, me arguing in court. I don't argue. I don't want to argue with you. There's no reason for that. I knew I didn't want to be a lawyer. So I was like, I'm not going to get my license because what's the point? But during law school, I had found the Innocence Project and I ended up working with them out in Northern California as a student assistant. And then they hired me to be a paralegal and investigator after I graduated. So I ended up spending five years total there. And I loved working with clients. Like I loved hearing from them. I loved hearing their stories. I loved going to visit them in the prisons throughout California. I really got to the point where it didn't feel like I was, I could do very much because the mission, while I love the mission so much, it was very narrow. The mission is you're looking for innocent clients. That's it. Most people in prison are not innocent, but that wasn't the point for me. Like there were a lot of needs I was seeing that just weren't being met. Speaker 2 (6:47) One of the things that you mentioned, I'm curious about, aside from you couldn't see yourself. arguing, which we'll talk about your strengths later on here. And I think that's a clear, obvious distinction in many different ways. Square peg, ground hole type of situation. But aside from that, what else made it really clear to you that this was not going to be a thing in the way that you thought it was? A Speaker 1 (7:10) lot of it had to do with what I saw as my own integrity. So in criminal law, which is the only law I was ever interested in. Trials and cases are built on, we want to call them facts, but not so much because there are so many rules that dictate what you can and can't say and what you can and can't present in a trial that I felt like if you've got a jury, you're asking 12 citizens to decide something and they don't have all the facts. And that felt very out of integrity to me. And I just, I was like, I can't do this. And I do want to say, I understand why the rules are in place. I know where they came from. I know what our goal was. And it did not feel an integrity to me to be like, well, but really there is all this other information. But because of these certain rules, you can't let people know it. And that might actually change their decision. And we're talking about somebody's freedom, maybe somebody's life. And it was just, it did not square with who I knew myself to be. Speaker 2 (8:15) When you're talking about. recognizing that the Innocence Project in particular was much more narrow than you wanted to focus on. What happened from there? At Speaker 1 (8:26) the same time, life sort of happened. One, I decided it was time for me to leave there. But two, my mother was getting older. Her health was... getting worse. And we did not have a great relationship growing up. So part of me was like, this is the time when I really need to repair that relationship. I really need to be there for her. So I ended up leaving California and moving to Eastern Tennessee, which is where she was. And so the beginning of that journey was really about rebuilding our relationship. And so that I never had to look back and regret where we were because I knew she just wouldn't be around that many more years. And I really wanted to get out of legal. I was doing the thing we do. I was looking on LinkedIn. I was looking on Indeed. I was looking what's available. And I so wanted to do something different, but it was like, I wasn't finding anything. I wasn't finding anything. And then a legal job popped up at the federal defender's office there. And I was like, I can do this. And that's sort of how I ended up sort of staying in legal. It was a good experience. And it showed me again, like. how easy it was to fall back into what's natural for you, like where it's easy for people to see your skills because you've done that before. Speaker 2 (9:37) What you're talking about, it's so easy to fall back into either the current trajectory or the trajectory that you've been on or the situation in which you already have skills developed or have a track record. I think that's maybe one of the hardest things for building any kind of a life and a career