The Man of Many Pivots with Dana Jacobson


Your career is more than a source of income. It provides you with a social network, variety and meaning in your life.

But what happens when your job grows dull?

Staying in a dead-end career is a recipe for burnout and depression. But if retiring is not an option for you, what can you do?

Pivot! Just like today’s guest Dana Jacobson did. He shares how to keep life interesting through multiple career changes.

In this episode, you’ll discover how to bring meaning and variety back to your life when your job grows dull.

Listen now.

Show Highlights Include:

  • A simple way to serve your community by having fun with your kids ([12:46])
  • The “optimist-practical” trap that could hold you back from a successful career change ([14:28])
  • How to ensure your spouse’s support with your next career change (even if it seems risky) ([15:01])
  • 3 habits that give your family name a good reputation that lasts for generations ([16:17])


DLP047 PC - The Man of Many Pivots with Dana Jacobson



Do you want a wealthy retirement without worrying about money? Welcome to “Retire in Texas”, where you will discover how to enjoy your faith, your family, and your freedom in the State of Texas—and, now, here’s your host financial advisor, author, and all-around good Texan, Darryl Lyons.


Darryl: Hey, this is Darryl Lyons. You’re listening to Retire in Texas. Thanks for tuning in. I appreciate you tuning in. I always have to give you the legal disclosure.

Dana: Always.

Darryl: I’m laughing here because we’re with an attorney and he’s our guest today, so you get to hear from Dana Jacobson. But, here, let me share with you our legal disclosure. This information is general in nature. It’s not intended to provide specific tax, investment, or legal advice. Visit PAXFinancialGroup.com for more information. Thank you, again, to PAX Financial Group for sponsoring this program. [00:58].6]

I want to encourage you to speak with one of our financial advisors. It doesn’t cost you anything. It’s complimentary and they have the heart of a teacher. You just have to text the number 74868. That’s 74868 and put in the word “Texas”. Really simple and really non-threatening dialogue.

Again, thank you for tuning in. Let’s get started with Dana Jacobson. Dana, thanks for being here today.

Dana: You bet. Happy to do it.

Darryl: Dana and I have known each other a while now, but what’s cool is I don’t know a lot about your background, so I’m going to actually discover Dana a little bit more here. But Dana is an attorney and he’s been a judge and he’s been in active duty, but there’s a lot of facets to Dana that’s really cool. Music, I know that, and so we’ll get into that today. But, first of all, do you live in San Antonio, or is it Fair Oaks or Boerne?

Dana: I’m in San Antonio.

Darryl: Okay.

Dana: Yeah.

Darryl: I always associate you with Fair Oaks, but we’ll get to that.

Dana: You bet.

Darryl: How did you get to San Antonio?

Dana: I’m an Air Force brat. Mom was born and raised in Brady, Texas. Dad was born and raised in Austin, and they went into the Air Force and we didn’t really come to Texas for about 24 and a half years. When my dad retired, he retired from a position in the military group in Venezuela, so that’s where I graduated from high school, and so we moved back here in 1975 because they said San Antonio was close enough and far enough away from all of their family. [02:16].2]

Darryl: Venezuela.

Dana: Venezuela, yep.

Darryl: You weren’t born there, were you?

Dana: I was not. I spent my last three years of high school there.

Darryl: Was he Air Force?

Dana: Dad was Air Force. He started out as an Air Force private, which was a while ago. It seemed to be not an airman basic back then. You were a private. He made buck sergeant, which is E-4, first non-commissioned officer grade. From there, he was accepted into the Aviation Cadet program, and so he got radio operator wings. He then got navigator wings. He then got pilot wings.

Darryl: Wow.

Dana: He was one of very few people of Air Force members who were entitled to wear three sets of Air Force wings. I’m not proud of him or anything.

Darryl: That’s pretty cool.

Dana: It is pretty neat. Pretty neat. [03:02].0]

Darryl: And when did he pass away?

Dana: He passed away in October, we’re coming up on five years ago now.

Darryl: Yeah, I remember that actually.

Dana: He was my law partner for 21 years.

Darryl: I remember that. Yeah. He was a good, good man, very well-respected.

Dana: You did, and you came to the funeral and we appreciate that.

Darryl: Yes, I do remember that. Obviously, in a military family, did your mother work?

Dana: Mom was … they first got married. When you’re in pilot training, you bounce around to a bunch of different little training bases, right? So, Mom was doing things like the advertising at a local radio station, those kinds of things. She mainly was having my sister and myself. We’re about 15 months apart.

Darryl: Okay.

Dana: And then she was an Air Force wife, and while she was doing that, she and Dad got married. She was a sophomore at Trinity University here. They, like many people’s parents, got engaged at Earl Abel’s.

Darryl: Yeah, at the literal Earl Abel’s. [03:57].4]

Dana: You bet, you bet, it’s a long tradition. She then had me and Kathy, my sister, and during the time that she was an Air Force wife, she also continued her education. She ended up getting a degree from Utica College in New York and then a bachelor’s degree from University of Arizona, and got her master’s at the U of A as well. Then got her PhD at the University of Texas. That was about probably a 30-, 35-year journey for her.

Darryl: Wow, that’s fascinating and where I was going with that, as I said, obviously was middle class.

Dana: Oh yeah, absolutely.

Darryl: Yeah, 30 years studying doesn’t necessarily … income doesn’t materialize just all of a sudden from …

Dana: Correct, yes.

Darryl: Yeah, y’all grew up, and I’m putting words in your mouth, but correct me if I’m wrong, in middle class, kind of prudent, conservative. Values were conservative I think.

Dana: Yes, values were always conservative. We were a middle-class family, but due to the nature of what dad did in the Air Force, he was a fighter pilot, but he was also in military intelligence. He was an attaché, a military attaché, which means that we spent a lot of time in the sort of State Departmenty kind of area where we were a middle-class family with a whole bunch of rich people. [05:17].5]

Darryl: Oh, I see.

Dana: Which was always interesting.

Darryl: Yeah, so at the officer’s club, that was interesting.

Dana: Yeah, I mean, O Club was okay because everybody is just –

Darryl: In uniform.

Dana: an officer, right? But when we were in Pakistan, my dad was the assistant attaché for the embassy and Pakistan for two years and the embassy pilot. You’re always dealing with all these very foreign service people and that sort of thing and lots of fancy parties and that sort of thing, where it was pretty clear who the folks with money were and who the folks who were there, because they had to be …

Darryl: Yeah, you could tell.

Dana: Yes, exactly, and the same thing when we were in high school. My mom was actually the head guidance counselor of my high school, which means I never got away with anything. [06:02].2]

Darryl: Oh.

Dana: But it was about 50 percent American, 30 percent high-class of Venezuelan and 20 percent everything else, except the Chinese because they wouldn’t send their kids to our school. Once again, we were middle-class kids dealing with children of the ultra-rich.

Darryl: Interesting.

Dana: It was always an interesting balance and tension.

Darryl: That is interesting. That is interesting. That can create some different dynamics. I can relate to the degree that I grew up in Boerne.

Dana: Right.

Darryl: And we didn’t have much money, but there are some rich kids in Boerne, so I kind of see a little bit of that.

Dana: You bet.

Darryl: And so, then you graduated high school and then I’m fast-forwarding a little bit, but went to undergrad where?

Dana: UT, Austin.

Darryl: And then where did you go to law school?

Dana: Here at St. Mary’s.

Darryl: Okay. Yeah.

Dana: I spent three and a half years in radio, in Texas radio after I graduated from high school, which was a radio-television-film degree, and then went to law school after that.

Darryl: Okay, and so you go to law school, and when you graduate law school, let’s let the audience kind of understand how that works. Do you just hang up a shingle and people come to you or how is it? [07:01].8]

Dana: You certainly can. My dad did that. My dad finished his undergraduate degree after he retired from the Air Force and then went to law school, and literally hung out a shingle at the house. That’s how he started to practice law. I, on the other hand, was looking for something a little bit more public servicey, I guess.

Darryl: Yeah. Okay.

Dana: I tried four times to get into the Air Force and the fourth time it actually worked. That’s a whole other miracle God story, but we won’t go into that right now. But the bottom line was that the Air Force JAG accepted me pending my passing the bar, so then I took the bar exam two weeks later, got married. Eight weeks after that, the bar results came back and I had passed the bar and went into the Air Force.

Darryl: Tell people what JAG is.

Dana: JAG is the Judge Advocate General’s Corps. When I joined, it was a Judge Advocate General’s Department. It switched to a corps about halfway through my career. Those are our military attorneys who do everything from prosecuting people and defending people in courts-martial or adverse administration, administrative actions to representing the Air Force in federal litigation. [08:10].0]

My last job on active duty was as the medical law consultant. That’s the hospital attorney at Wilford Hall Medical Center, so a broad variety of things that you can do as an Air Force JAG.

Darryl: How long were you JAG?

Dana: I was in active duty for six years and I was a reservist for 24.

Darryl: A 24-year reservist.

Dana: [Yes.]

Darryl: Active duty, then reservist. Did you get deployed while you were a reservist?

Dana: I got deployed in place.

Darryl: Understood.

Dana: That means that the deployment opportunity when it came or the deployment opportunity when it came up, I was at Air Intelligence Agency, so it was very sort of intel heavy in surveillance and reconnaissance, that kind of thing, and I basically backfilled the active duty Staff Judge Advocate there as a colonel.

Darryl: That makes sense, and then while you’re fulfilling your reserve obligations for 24 years – [09:05].6]

Dana: Yes, sir. Yes, sir.

Darryl: – thank you for that and thank you for the active duty, but it’s a little bit of a challenge because you have this obligation to fulfill and an opportunity as well, but you still need to work. Where did you work during that time?

Dana: When I first got out of the Air Force, because I had been an MLC, a medical law consultant, I actually was hired by an insurance defense firm here in San Antonio that did medical malpractice defense. I represented at hospitals, hospitals and medical professionals who had been sued for malpractice, and that’s how I started out and then just really was not excited about the big law firm issues.

Darryl: It’s hard.

Dana: It is, and unlike the military where there was an incredible esprit de corps and camaraderie, large law firms pit their associates against each other and I was never comfortable with that. I went from there to a smaller insurance defense firm for about a year, and then my dad asked if I would join him at his firm, and that just seemed like a really good idea to me. [10:11].0]

Darryl: Now, you were a judge for a little while.

Dana: Yes, I still am an associate judge. I was the judge, the municipal court judge in Fair Oaks for 15 years and I have been the associate judge in Cibolo for probably 10 now. I’m also the prosecutor out in Boerne, so if you’re listening from Boerne, please don’t speed. But I’ve been doing that as the primary, the alternate, and then the primary again for a little over 20 years.

Darryl: You mentioned Fair Oaks, Cibolo and Boerne, and for those that are listening out of the state or even out of the country for that matter, those are just smaller communities right outside of San Antonio, but San Antonio has grown so much that they’ve kind of been absorbed and they do have their own municipality and their own courts and their own rules. Actually, I live in New Braunfels and I had to sit through a city council meeting. It was five hours and it was rough.

Dana: It’s brutal.

Darryl: It’s brutal. But I think it’s kind of cool to think about, and we’ll get into what you’re doing today a little bit, and since this show is Retire in Texas, to a certain degree, we talk about retirement as pivoting, right? [11:12].8]

Dana: Sure.

Darryl: You hear that at PAX. We pivot to another part of our lives, and “retired”, by definition, is the disposition of an asset over its useful life. What you’ve done is you haven’t retired.

Dana: Ouch.

Darryl: I know, right? Exactly. Exactly. It’s kind of crazy that that’s the way we use that term.

Dana: Sure.

Darryl: But you’ve pivoted several times now, so you’ve pivoted and it hasn’t been just a stark [turn], like you haven’t made a sharp turn. You pivoted from active duty to reserve.

Dana: Right, reserve and civilian practice. Right.

Darryl: Right? And then, you’ve pivoted from a major law firm to Dad’s practice.

Dana: Right.

Darryl: It’s not like you went to an extreme, like, Hey, now I’m going to go be a coach, and then pivoting to be a judge. I just think this is cool how you’ve done it and everything kind of ties in, and you’ve just kind of let the Lord just kind of lead you in different directions, but it’s all been rooted in the legal field. [12:04].4]

Dana: Yes.

Darryl: And it continues to be that way. What does it look like today?

Dana: Today, my dad, of course, retired in 2015 and passed in 2017. I am the sole shareholder of the Jacobson Law Firm. It is a professional corporation and we concentrate in three main areas, and that is estate planning, business law, and probate. Also, as noted, I do some public sector stuff as the judge and as a prosecutor, and I’ve also been a city attorney for a couple of small municipalities.

Darryl: I didn’t know that.

Dana: Yep. Yep.

Darryl: Now, you’ve also been a professor, haven’t you?

Dana: I have, yes.

Darryl: I forgot about that. Was that at Hallmark University?

Dana: Yes, I taught undergrad business law and their master’s program, business law.

Darryl: Okay, so you’re the master pivoter here.

Dana: I am.

Darryl: You’ve done active duty, reservist, civilian, judge, municipalities, professor, and now let’s talk about your music.

Dana: Okay, songwriter, a singer-songwriter, and have done that for, gosh, 20 odd years. I’ve got a couple of tunes published, which is always kind of fun. [13:05].0]

Darryl: Can we find them on iTunes?

Dana: Probably, yeah.

Darryl: Okay.

Dana: I know we could. Yeah, it’s been a little while, but I always tell people it’s great fun because I don’t have to feed my family with it, right?

Darryl: Yeah, yeah.

Dana: I’ve been real blessed to have a small group that’s kind of ad hoc called on the side and we will assist people with their fundraising activities and that kind of thing. One of my daughters sings with me. Both of my sons-in-law play with me.

Darryl: That’s cool.

Dana: I tell people all the time, what I got out of these two marriages, it was a couple of really good musicians.

Darryl: That’s so cool.

Dana: Yeah, my younger or my older daughter is already just a great singer, so we enjoy it.

Darryl: Now let me provide a point of clarity to our audience. You said what you got out of these two marriages. You’ve only been married once.

Dana: No, no. Yes, my children’s marriages.

Darryl: Yeah, okay, got it. Yes.

Dana: I have been married once for 37 years last month –

Darryl: I thought so.

Dana: – to Betsy.

Darryl: Congratulations.

Dana: Thank you, and she’s a trooper. [14:00].3]

Darryl: She supports you in all these pivots.

Dana: She does. She makes her presence and opinions known.

Darryl: Yeah. Okay, good.

Dana: Yes, she does, in fact, support me in all these things and, as you know, these kind of decisions you have to make in concert and in conversation with your spouse and in just supplication before the Lord.

Darryl: She gives you good feedback and says, “Hey, this makes sense. This pivot makes sense. This doesn’t,” and y’all work it out.

Dana: We do. We do.

Darryl: Yeah, and has there ever been a time where she said, “Hey, Dana, that’s a good idea, but don’t do that.”

Dana: A time or two, yeah, a time or two.

Darryl: Maybe to that network marketing thing we were talking about before.

Dana: Yeah, yeah.

Darryl: Probably some of those.

Dana: Yeah, and we both went through that, but, yes, there are times. I mean, I think that I tend to be more spontaneous than she is.

Darryl: Optimistic. You’re an optimist.

Dana: Yeah, I’m just a natural optimist. She is not. She is much more, she would say, practical.

Darryl: Good balance.

Dana: It really is. It really is, and like I said, we– [15:01].3]

Darryl: Tell the audience how you work that out, though. I mean, can you give us some substance behind that? Because I deal with a lot of people. You do, too. And marriages are, you’re married for 30, 40 years, and some of the people that are listening, and this is an unfortunate case, but have developed coping mechanisms through their career that they’ve never been able to have robust conversations like you’ve had. How would you advise somebody who’s thinking about pivoting? How do they communicate with their spouse on their concerns and what their visions look like? That’s a loaded question, I know.

Dana: It really is, yes.

Darryl: But you’ve done it well. That’s why I’m asking you and I know you have.

Dana: And what I would love for people to think is everything always went swimmingly and we’re in agreement with everything, and that’s simply not the case. But I’ve not ever taken a position or a swing, or a pivot or change it direction, without, one, having a full and complete conversation with Betsy, and, two, without her saying, “Okay.” Sometimes it’s that and sometimes it’s “I think this is a great idea.” She is extremely supportive of me, and if I hear her saying, “Absolutely don’t do that,” I take that really seriously. [16:14].0]

Darryl: Good.

Dana: Yeah.

Darryl: Good. I believe that to be true.

Dana: Yeah.

Darryl: A couple more questions as we kind of turn the corner here. It’s been fast-paced already, so there’s just so much to your life that’s so cool. First of all, I just want people to know, as long as I’ve known you, everyone would say one thing about you, that you’re a good man.

Dana: I really appreciate that.

Darryl: But the question is, I know you’ve honored and respected your father and you’ve alluded to the character of him. What would he tell you to do over this next chapter of your life, if he were advising you?

Dana: His advice to me was often more in the nature of “be a good man.” Whatever you choose to do, commit to it, and make sure that God comes first and family comes second, and jobs and careers and that sort of thing come after, significantly after those two things. [17:03].8]

Darryl: Oh, that’s good to hear.

Dana: It’s what he always said. Now, Dad was … we have talked about my dad as being sometimes wrong, but never in doubt. He showed that, but you never had any concern or confusion about where dad stood on any particular issue, and that’s a good thing.

Darryl: It is.

Dana: Because, at least that way, you know who you’re dealing with and what those responses are going to be, and you can sort of tailor your approach accordingly, which I sometimes did. Dad was old school in terms of believing that a handshake was all that was necessary. It took a little while and a little conversation to get him to agree that we really kind of probably ought to have fee agreements with our clients, and things like retainers and that sort of thing, because Dad believed in the inherent –

Darryl: The good in people.

Dana: – goodness of people, yeah, and that they wouldn’t commit to do something and then not follow through. I guess, at some level, that might even be naïve, but that’s how Dad lived his life. [18:11].4]

Darryl: And he would tell you, “Dana, my son, my Jacob-son, be a good man.”

Dana: Yeah.

Darryl: Now, I think that’s worthy of people just settling in on, because this is a wonderful picture of values being transitioned down.

Dana: No question.

Darryl: And what we say about money is an inheritance is what you leave to someone, but a legacy is what you leave in someone.

Dana: Exactly.

Darryl: What I’m seeing today is that legacy.

Dana: And I’ll tell you that my dad got it from his dad, and as I mentioned to you, we didn’t live in Texas growing up, so I barely got to know my grandparents until I was in college, and actually ended up writing a song called The Name, which talks about what my great-granddad, my granddad and my dad taught me, which is when you need a good name, nothing else will do. [19:01].3]

Darryl: Oh, that’s so good.

Dana: Yeah.

Darryl: So good. That’s scriptural, right?

Dana: It is.

Darryl: It is very scriptural. All right. Thank you so much. But I do have one more question.

Dana: Yes, sir.

Darryl: What’s your favorite salsa?

Dana: Can we expand salsa to include pico?

Darryl: We can, yeah.

Dana: Okay, mine.

Darryl: Yours? That makes a good pico, huh?

Dana: Betsy and I make some real good pico.

Darryl: You like it chunky?

Dana: Yeah, chunky and fresh.

Darryl: With hot? You like it hot? You like peppers in it?

Dana: I mainly go with jalapenos and usually go with three rather than the recommended two, but we always have fresh pico in the fridge.

Darryl: Do you have a garden?

Dana: We do not. We have talked a lot about doing like a raised bed or something like that for just onions and tomatoes and jalapenos –

Darryl: Exactly.

Dana: – which should just be great. Maybe the next growing season.

Darryl: Yeah, maybe, and that’s another thing you can pivot to.

Dana: Exactly, exactly.

Darryl: Thanks again for being here.

Dana: Selling pico.

Darryl: Yeah, exactly. The Jacobson Pico, it started right here.

Dana: That’s right.

Darryl: Hey, thanks again for being here. This has been great.

Dana: I really appreciate it, Darryl. Thanks.

Darryl: And thanks for listening to the end, everyone. Again, you’re listening to Retire in Texas. If you need a visit with a financial advisor, just text the word “Texas” to 74868. That’s “Texas”, 74868. I want to remind you again, you think different when you think long term. Have a great day. [20:12].2]


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