Jordan Ostroff: Applying a Litigation Mindset to Your Life

In this episode, Steve Fretzin and Jordan Ostroff discuss:

  • How business planning and life planning are more similar than you might think.
  • Building a life that makes you happy.
  • Helping yourself make the right choices, not the wrong ones.
  • Achieving multiple outcomes from the same action (not multitasking).

Key Takeaways:

  • Put a team together to support you so you can focus on the things that are your unique talent – in your business, and in your personal life.
  • What low-hanging fruit are you overlooking that could change the game?
  • Start making small changes, they will add up and result in massive changes in less time than you think.
  • You are not the best at most things – delegate the things that you aren’t the best at. Know your limitations.

“You’re not sacrificing the work, you’re empowering somebody else who is better at these things to do them better than you would.” —  Jordan Ostroff

Get a free audio copy of Steve’s book “Legal Business Development Isn’t Rocket Science” here:

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Episode References: 

About Jordan Ostroff: 

Jordan Ostroff is a successful lawyer and visionary entrepreneur. After working as a prosecutor for the State Attorney’s Office, Jordan founded his own firm, Driven Law in 2015, a personal injury firm that focuses on using technology and automation to provide top-level legal work with care and compassion. Over the next few years, he went from a struggling lawyer to a successful business owner. He has made it his life’s goal to help more law firm owners run a firm they can be proud of and live a life that’s even better!

Connect with Jordan Ostroff:  





Connect with Steve Fretzin:

LinkedIn: Steve Fretzin

Twitter: @stevefretzin

Instagram: @fretzinsteve

Facebook: Fretzin, Inc.


Email: [email protected]

Book: Legal Business Development Isn’t Rocket Science and more!

YouTube: Steve Fretzin

Call Steve directly at 847-602-6911

Show notes by Podcastologist Chelsea Taylor-Sturkie

Audio production by Turnkey Podcast Productions. You’re the expert. Your podcast will prove it.


Steve Fretzin: [00:00:00] Hello, everyone. Have you ever wondered how much more business you could be generating each month? Well, you can take the Be That Lawyer challenge to find out. If I’m unable to help you find the money that’s been evading you, I’ll pay your hourly rate for the time invested together. Just go to to sign up. I’m challenging you. Now enjoy the show.

Narrator: You’re listening to Be That Lawyer, life changing strategies and resources for growing a successful law practice. Each episode, your host, author, and lawyer coach, Steve Fretzin, will take a deeper dive helping you grow your law practice in less time with greater results. Now, here’s your host.

Steve Fretzin: Well, hey everybody, welcome to Be That Lawyer. I hope you’re having a lovely day today. This is a wonderful opportunity for you to stop working in the business and start working on the business to be that lawyer, someone who’s confident, organized, and a skilled rainmaker. If you’re hearing this show for the [00:01:00] first time, it’s all about helping you to do that.

If you’re an existing listener. Please don’t be shy. Tell your friends and family and other lawyers, you know, about it. Let’s build our audience and continue to help people to be their best versions. You guys know, I’m constantly trying to like, figure out best, the best guests to bring on here. And one of the, one of the ones I’ve known longest time that I know will add a ton of value for you guys is Jordan.

He’s with me here today. How are you doing Jordan?

Jordan Ostroff: I’m doing very well, Steve. Thanks for having me.

Steve Fretzin: Yeah. Back from a really crappy cruise, literally like crap everywhere. Not good. Not good. No. But now you’re back working, which I know is, is your, you know, you enjoy that and you enjoy playing, but welcome.

Let’s, let’s start off Jordan with what I love to do, which is the quote of the show. And James Clear is really, I don’t know. How long has he been around? Cause I know like, is that atomic habits? I

Jordan Ostroff: don’t know that this quote is in atomic habits, but I mean, atomic habits has been a New York times bestselling book for.

Years pops up every now and then it stays on. It comes back. It’s I read it last [00:02:00] well, so we’re, we’re recording this on January 2nd. So I read it last year and the year before I’ll probably read it again this year. Yeah. Um, it’s just, it’s such a great book. And so I love the quote that we’ve

Steve Fretzin: got here. And it is a system is perfectly designed to get the outcome it currently gets.

So talk to us a little bit

Jordan Ostroff: about that quote. Yeah. I mean, look, here’s the thing. The entirety of life is built in systems. Obviously, I think most of the time we think about them from the standpoint of like, at work, having a specific system, but like, your body is a system. The food that you put in with the exercise that you do leads to the weight that you have.

And so, you know, your current weight, your current sleeping habits, your current income amounts, your current relationships with other people is the outcome of these systems. And all of them are as currently designed, get you the outcome you currently get. So if you want to change your life in any part, you have to change the system.

Steve Fretzin: Really, really great. And by the way, a hack, if anybody’s interested is to go to YouTube and type in atomic [00:03:00] habits. There’s a great like 30 minute video that really breaks down that book. In some form of animated fashion where you can stop and listen to things again, but it’s really just such a great, uh, a great book has been brought up on the show number of times.

I enjoy it. Um, and, and, and teach, you know, a decent amount of it. Because I think without systems, just winging it isn’t a system. I think Jordan, right? I mean, maybe it is a system. It’s just a really bad

Jordan Ostroff: system. I mean, that’s the thing. Like having no system is still a system. But, and look, it could be as complicated as like building out an entire CRM.

It tickle you about, you know, reminding you to do this. Remind you to do that. And it could be telling, Hey Siri, every 35 days, remind me to check in with so and so. It could be a note on a calendar. It could be a sticky note on the side of your computer. You know, there’s. There are so many different things, but with, but if you don’t have an intentional system, you still have an unintentional one.

Steve Fretzin: It’s like making no decisions. You’ve made a decision. Something that’s in a similar kind of fashion. Yeah. So Jordan, give us, you know, [00:04:00] welcome to the show, man. We’ve known each other a long time. And, um, I always admire, you know, the way that you’ve run your life and structured your life using, I think these systems you’re talking about, and we’re going to get into helping lawyers, you know, Uh, live a lawyer’s life that they can really enjoy and, and you’ve done kind of done it.

So give us a little bit of background because I don’t think you’ve always been that way, correct? Oh

Jordan Ostroff: no. And I had to hit, I forgot what the, the rock bottom, yeah, we’ll call it, I’ll call it rock bottom. There’s, there’s more artful phrases, right? Uh, are

Steve Fretzin: you trying to say I’m not

Jordan Ostroff: artful? No, I’m saying there’s, there’s some, uh, philosopher from 4, 000 years ago in Japan that coined some perfectly encompassing phrase that, that hits this, uh, yeah, we’ll call it rock bottom.

Um, I, I, look. The beauty of Rock Bottom is you know, you can’t go deeper, you know? There’s a, there’s a weird beauty to it. So my Rock Bottom came when my wife told me she was pregnant with our son, who is now, uh, five and three quarters. As he will tell you, because I was super happy, it took us over a year to get pregnant, [00:05:00] because we were going through a ton of emotional stuff with the firm, financial issues and whatnot, and I was super happy, and then immediately flipped to like, what the hell am I gonna do, like, we’re working 80 hours a week, we’re 200, 000 in debt, we’re making no money, And now someone’s going to hand me a baby, you know?

Um, but thankfully that was able to really put me in the mindset to pull back. So cut a 120, 000 a year marketing budget cut down on the number of cases. I met, uh, Greg Eisenberg, who’s my, uh, former, well, he still owns legalese. He was my business partner there, bought me out last year, um, on it. And he really walked me through like marketing one on one.

And now I’m really trying to get lawyers to walk through like life planning one on one, you know, let’s take the same concepts that we apply to our business for business plans and marketing and doing great legal work through our life and end up with the same concept of results. Obviously, like your business is different, gets different results than you want out of your life, but it’s a lot of the same process.[00:06:00]


Steve Fretzin: we have this, you know, very intense conversation just leading before I hit the record button about, you know, how frustrating life can be today. I mean, it’s not just at the office. I mean, I was talking to you about trying to get my insurance handled and dealing with the rigmarole of that, dealing with my father, who’s in an assisted living, like a rehab center and how to like get him out and all the moving parts and all that stuff.

So just. I think there’s just so much coming in that is pushing us down and making things so complicated and so difficult that lawyers and just people in general, but lawyers in particular have a hard time being happy because there’s just business and personal stuff that just all kind of like you were talking about, you know, in your, in your previous life, like pressure pressing down on your, on your

Jordan Ostroff: shoulders.

Sure. Oh, and as like. What’s most lawyers work? It’s other people’s problems. You know, unless you’re doing adoptions and everyone’s happy at the end, like you’re sitting there arguing and in litigation, there’s another lawyer arguing against you, like talking about the extra [00:07:00] complexity of it. I just, what I really want to see more lawyers do though is apply that same like litigation mindset to their life.

You know, when you’re sitting here like, okay, I have a paralegal who gets this file together for me. We’ve got a law clerk that puts these stuff together. We’ve got a runner that does all these things like do the same thing for your life. You know, have a housekeeper, have a landscaper, have whatever other team you need to support you in the things that you don’t want to do in the things that aren’t worth your time and the things that you’re not great at and really be able to focus on your unique talent, whether that’s.

Litigating in front of the, you know, in front of a judge or jury, whether that’s sitting down with a client to do the consultation, whether that’s being there for your friends and family, you know, being a rock that they can lean on just as much as your clients lean on you. Like, let’s get more time doing those things and less doing bullshit.


Steve Fretzin: that, is that one of the main reasons why people in general are just so unhappy? Because they spend most of their time doing low level work. That’s, that’s not really the best use of their time and their [00:08:00] specific set of skills. Um,

Jordan Ostroff: to some extent. I mean, like, so I would put a fine point on that. And I think we have, we have this concept that we think it’s great to be busy, which is, I think, stupid.

Part of it is exactly what you’re talking about. But part of it is just like weirdly taking on other projects that don’t move the needle. And so instead, I think we need to really like get into that 10, 000 foot view, decide what do you actually want out of life? What role do you want your work to play in it?

What role do you want relationship to play in it? What role do you want your clients to play in it, friends, and then really make decisions to have those things happen instead of sitting here and saying like, Oh, I have two hours free on my calendar today. Let me go, I don’t know, fuck around in the Jones file for 20 minutes.

Let me file. Let me respond to this email. Like, let me do all these other things that sort of seem to be pressing without ever taking the time to think like, What do I actually need to be doing? And then what do I actually want to be

Steve Fretzin: doing? Well, is that, is that, is that just hard for people because you’re in it?

Like when you’re [00:09:00] seeing things from your perspective and out of your eyes, it’s hard to see what you really want or to try to come up with a plan or to try to look at it from, from a perspective that. Where you can, where you can, you know, have that internal or external conversation completely.

Jordan Ostroff: And it’s so weird to me, as much as lawyers get a bad rap for being like egotistical a holes and trust me, I was one, maybe still am one.

It’s a daily struggle. We, we also like sort of refuse to be selfish, you know, like the amount of the lawyer suicide rates, five times the national average, the lawyer and oppression rate is between two and three times the national average, because like, we refuse to put ourselves first. Even in a situation where we’re trying to work from an empty cup and burning a candle at both ends and burnt out.

Like it’s fascinating to me that, you know, so sitting here like, Oh, well, I can’t take an hour to get a massage because I need to do all these work for these clients. But then like you do that work worse because you’re in that mindset of not having the hour to relax and let your brain catch up and whatnot.[00:10:00]


Steve Fretzin: So how, how do law firm owners and lawyers in general, I mean, even a lawyer that’s at a firm is still an owner of their time and of their position. Um, I always think of, of every, everyone in business as an entrepreneur, whether they have an umbrella of a firm around them or it’s their own, how, but how, how do they build a life that makes

Jordan Ostroff: them happy?

Yeah, I mean, look, the more that you can get high level about it, the better. You may not have that luxury. When I was sitting there with, Hey, we’re having a kid and we’re 200, 000 in debt. Like it was not a, Oh, let me think about not working on Tuesdays and Fridays. Like that was not in that moment. You didn’t go right there.

Right. But I could go to like, all right, I’m going to cut our 120, 000 marketing budget. Let’s see how many fewer cases come in. I won’t have to take on an extra 20 cases a month to just. Get the marketing nut handle. And after that, so that was 20, my kid was born in 2018. So that was like aggravation, 2017, 20, 2018.

So on [00:11:00] $120,000 less spent on marketing. My firm made $5,000 less the next year. It’s not that the marketing was that bad, it’s that we were able to organically grow the firm in that timeframe also. Yeah. But it was still $120,000. I didn’t have to spend to handle fewer cases to make almost the same amount of money.

So like what are the low hanging fruit things, you know, is it hiring a dedicated assistant for a thousand to $2,000, virtually for three to $4,000 a month locally? Do you have enough extra work that, you know, they can take some stuff off your plate there? Is it hiring an associate so you don’t have to do all the litigation?

Is it hiring a great business coach? Or, you know, signing up with Steve’s program to get more marketing in the door? You know, is that your problem? Is it not having enough case? Do you want to actually focus on being a rainmaker? Do you want to focus on generating the business? Do you want to focus on being a farm owner?

Do you want to focus on being a marketer? Do you want to focus on being a parent, spouse? Father, son, kid, like whatever, really see like where the small [00:12:00] changes are. And then like you get an hour a week back here, you put that into getting another hour a week back and then it starts snowballing into having a life.

You actually want to live. I think

Steve Fretzin: part of it is looking at that top level. Like you mentioned, the other is, is then getting detailed about like maybe tracking your day and understanding, Hey, how did I start my day? What happened every 15 minutes, but not tracking time for billing, tracking time to identify.

And put a number next to it. Like, so I, I got up and I checked my email that checking email and getting rid of spam and getting rid of solicitations. Is that a 350 to 500 dollar an hour job, or is that something that someone could do for 10 or 15 dollars an hour? Then I had to get up and do my laundry.

So that’s a personal thing that took me 2 hours. Okay. Is that something I can outsource and, you know, have picked up and delivered for whatever 30 dollars a week? So it’s all, it’s all the things that are going on that we need to start identifying. What do we enjoy and what’s the best use of our talent and skill and getting rid of the stuff?

Is that a big, [00:13:00] how big a part is that? Yeah, a thousand

Jordan Ostroff: percent. In fact, um, anybody listening to this, if you email me, I’ll send you, I have a time audit sheet. It is just an Excel spreadsheet. It does what Steve’s talking about. It breaks it down by hour, half an hour, 15 minutes as we get into like the day.

But then I have two columns after that. The first one is, does it give you energy or stop your energy? So like, hopefully if you wake up from a good night of sleep, you should have, you know, plus five for energy. If you hate doing the laundry, it might be a negative four at the end. If you hate talking to.

You know, Mr. Jones, every time he calls, that might be a negative five. And then it has on a scale of one to 10, how delegatable is this? You know, is this a situation where if you had the person, they could take this task on tomorrow? If you hire a housekeeper, can they start doing the laundry and the dishes tomorrow?

If you hire a paralegal, can they start doing, you know, putting together these files tomorrow? Or are these things that you don’t have enough of a system built out to be able to really do? And then, ultimately, you can do math. You can take the hours that things are, [00:14:00] multiply it by the energy things, multiply it by the delegatable, determine what’s the right step from there, all sorts of things, um, off of that.

But yeah, Steve, I mean, you, uh, you teed me up for that one. I

Steve Fretzin: did. Is that, is that, well, let me tee up one more thing. Is that, is that set up as a link we could put into the podcast show notes to like give away?

Jordan Ostroff: You know, I’m pretty sure jordanostrap. com is live right now and it’s on there. Okay. But, uh, I don’t want to be a hundred percent, because I But this, this

Steve Fretzin: show is probably going to have a gap of a month between when we tape it and when we air it.

So I’m hoping that you get some progress in a month. But Oh

Jordan Ostroff: yeah. It’s Alright. It should

Steve Fretzin: be on there. Alright. So go to Gordon, go to Jordan’s website to grab that, um, form. I think that’s a great way to start off the year, by the way. Is to start, you know, really dissecting what you’re doing in a given day, a given week or whatever.

I love the extra categories of negatives and positives and energy and not energy. I thought about putting numbers next to it, but I like yours even better. Well, cause you’ve got the

Jordan Ostroff: time on it in the hour, you know, the hours there. And so. I just, it, it really [00:15:00] boils down to are you concerned about money or are you concerned about time?

If you’re concerned about time, you want to get the larger things off your plate ASAP. If you’re concerned about money, then you have to look at what’s the easiest stuff you can delegate right now. And it’s

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Steve Fretzin: So are the things that we’re talking about helping lawyers be happy, is that really what it, what, how, how are they being happy? And then how does that like positivity about, you know, that happiness or that, that feeling of, of joy and doing what you love and not doing all the grunt work, how does that change people then?

Jordan Ostroff: Oh, I mean, it’s night and day. So like, let’s go back to my, my favorite experiment in the history of time is the marshmallow I don’t know if you’re familiar. No. No. What’s the

Steve Fretzin: marshmallow test? Okay.

Jordan Ostroff: So they took a bunch of, I want to say it was like six year olds, and they sat them down in a room and they put a marshmallow on the desk and they said, Hey.

You can have this marshmallow right now, or if you do X, you can have two marshmallows. So in some situations, it was if you can wait 20 minutes, we’ll come back. In some situations, if we have to step out of the room, you [00:18:00] can call us back in whatever you need, like whatever that was. Yeah. And, and then they took these kids and they tracked them.

So like the kids that could wait for the second marshmallow were happier, were more well adjusted, did better in school, whatever, you know, we’re, we’re pillars of the community. The funniest thing, though, is they actually have breakdowns of, like, how the kids did it. So some kids, like, took the marshmallow and made it into a ball and started playing with it so they wouldn’t eat it.

Some kids turned their chair around so they wouldn’t look at it. Like, it was very fascinating to see the coping mechanism of this children during this situation. But, like, but that’s life. You know, like, the ability to have willpower, it’s a limited resource. And so the more that you are happier, the more that you’re showing up in the right mental state, the more that you have leisure time or any semblance of whatever leisure means to you, the easier it is to turn down that marshmallow in this moment.

You know, if you are working 80 hours a week and making no money, you’re eating the marshmallow right then and there. But if you’re not, now you [00:19:00] can take that sacrifice. Now you can invest in that future marshmallow. And look, I know it’s silly to call it a marshmallow. Change your retirement. You know, time with your friends.

Uh, an actual vacation with your spouse where you don’t bring your laptop and sit on the beach in Hawaii while still working and sending emails and replying to Discovery and whatnot. You know, like these are little things. That we have to do now that add up to actually being able to have the life we want to live.

But what,

Steve Fretzin: what, what, so then what do you think? I mean, maybe you could just use your own example and experience, but like having that self control to wait for the second marshmallow or to do things that are going to benefit your life positively. What do you do? How do you, how do you keep yourself from making bad decisions, eating that, you know, Snickers bar in the middle of the day or doing things that you used to do, but you don’t do

Jordan Ostroff: anymore?

Well, okay. So I’m a Reese’s guy and it still happens, but look like, so first you give yourself some grace. Like that’s the beginning of this. I am not perfect. I don’t think I want to be perfect. I like [00:20:00] the struggle to be better every day. So like, first of all, give yourself a fun of grace and appreciate where you are now.

You are a lawyer in America. You’re probably making, you know, almost six figures or high level of six figures. You’re probably in the top 10 percent of income earners and education and whatever, yada, yada, yada. We have a million things going for us. So really so much what we’re talking about are these small changes right here, right there, you know, it’s marking off your calendar at three o’clock every Wednesday so that you can go see your kid play in the baseball game.

It’s marking on your calendar for the first four hours every Friday to work on the business. You can get to that to do list that’s been building up for five years. It’s some of these small changes. And then every time you do make that extra win, reward yourself in a way that is healthy. You know, please.

I hope it’s not like, oh, I did everything I need to do this week. Let me shoot up heroin on Friday. I

Steve Fretzin: got smashed. I got smashed right

Jordan Ostroff: afterward. [00:21:00] Now, like probably not find something that you enjoy, you know, for me massages, like that’s a huge thing. Okay. I, I enjoy them. I feel better after then. And it’s an hour of like shutting my brain off.

I end up actually having really good ideas after it, but like, it’s a reward for me doing what I need to do. Find some things that work for you that are, you know, whatever semblance of healthy you have, whether it’s food, whether it’s time with friends, whether it’s time for yourself, whether it’s, you know, splurging financially on something.

In reason and reward yourself over and over again, because ultimately, like, that’s what I have. It is right. It’s the reward that we get the dopamine hit after doing what we want to do. And it worked just as much for opening up your phone and refreshing facebook as it does for completing that task off your to do list.


Steve Fretzin: mean, business development, that’s a, you know, poke at poke at the bear of something that I’m dealing with every day. But it’s hard for lawyers when they’re dealing with family issues, they’re dealing with business, they’re dealing with people, they’re dealing with all this stuff. And now, hey, on top of that, you need to go out and build a book of business.

You need to go [00:22:00] network. You need to go do these things. So, I mean, obviously having a system, number one, you know, obviously I’m teaching that the other piece that, and we talked about this, I had a class I teach every Tuesday morning and we set up accountability buddies because I know for me working out, you know, I go to Pilates and if I didn’t have to go to a class with a bunch of people that were expecting me and pay for it.

You know, I wouldn’t do it right. So having accountability buddies for things that, you know, you need to get done. And by the way, other people do too. That’s a really big help to ensure that you’re now not only committed to do something that’s good for you, but you’re also helping out someone else and they’re helping you.

And so I think that’s sometimes like a workout buddy, but for things in your, it could be for working out. It could be for business.

Jordan Ostroff: So if you ever read Gretchen Rubin’s four tenancies.

Steve Fretzin: I don’t think so. Okay. I’m not a, I’m not a big reader like you.

Jordan Ostroff: All right. So at the very least Google one article about it.

So there’s four tendencies of people. I think you’re an obliger and it’s not an insult, but she talks about like, some people are internally motivated. Some people are [00:23:00] externally motivated. Some are only one, some are both, and some are neither. So that you’re for like, you can be yes or no on either quadrant on either side.

Okay. And so knowing which one you are helped. So like, if you’re an obliger, the accountability buddy is great. If you’re internally motivated, the accountability buddy doesn’t, doesn’t mean the same thing. But like finding that stuff out is helpful from there. But then ultimately, like, I hate the concept of multitasking in the business sense.

Like I’m not writing an email while I’m here with you. However, how many things can you do the same thing that achieves multiple goals? So if you’re trying to lose weight and you’re trying to do business development, can you do a group walk with referral source? If you’re trying to spend more time with your kids and build a book of business.

Can you, if my kid loves golf, I’ve got a top golf membership. So guess what? He gets out of school two o’clock on, on, uh, on Tuesdays. We went and played golf, whatever it was, three Tuesdays ago with a referral source and his kids who are about the same age as my kid. So now the families are together. [00:24:00] We’re talking, you know, a couple of cases here and there and whatnot, while having fun with everybody.

So I’m cool with like multitasking, I’m cool with not multitasking, I’m cool with multiple outcomes from the same thing. And so I know there’s so many ways for us to put a little bit of thought into how we can achieve more of the outcomes that we want without having to add the inputs, you know, without having to work out and also do a lunch and also spend time with the kids and also do this.

Can we do some of those things at the same time?

Steve Fretzin: Yeah, and, um, like, you know, I have my book, um, legal business development isn’t rocket science is now on audio. So people can listen to that while they’re working out while they’re driving and just so now you’re learning business development as a skill while you’re doing something else that maybe is, you know, not, you know, thought provoking like driving something like that.

Um, but I know that for a second.

Jordan Ostroff: Yeah, yeah, please. So I read 175 books. I read and listened to 175 books for last year. The amount of time [00:25:00] that I did not listen to the radio in my car, like, probably cut it 90 percent down. Happened to be on a cruise, they happened to be playing, like, the Top 40 stuff. There wasn’t a single fucking song that I did not recognize in a year of basically not listening to music.

Mhm. So, like, it is fascinating to me. How slow some of these things, um, boom. And so, yeah, I mean, you know, a 20 minute commute on the train or in the car or something like that times going home is 40 minutes times, five times a week. That it’s 200 minutes. I mean, that’s a book a week right there.

Steve Fretzin: And a big, a big part of what you work on with lawyers and that you’ve done yourself as sort of proof and, and of concept is delegation.

And, and I’ve had a number of, of guests on Dan Warburton, uh, most recently was on and talking specifically about delegation. He’s in assassin at it. But you’ve got your own kind of methodology. What, why, why are lawyers so, so first of all, why are they, why do they have so much trouble delegating, and then why is that so critical for them to do?[00:26:00]

Jordan Ostroff: We can’t delegate. We’re unique unicorns. We went to law school. Yeah. We were, we were forged in an ivory tower of our own making. It is, it is, you could go to jail for being a lawyer for doing legal work without being a lawyer. Like we, who else has that opportunity? No, but seriously, yeah. Fucking delegate.

And, and look, here’s, here’s the thing about it. Please, I, I have a moment. I’m gonna, I’m gonna tell a story. It was my 1L year of law school. I had been doing mock trial in undergrad beforehand. So I got a specific scholarship to come to my school to do mock trial. We had a very good mock trial team. I got placed on the shadow team with a bunch of the really good 3Ls to try to learn from them.

At the end of the year, one of the 3Ls took me aside and was like, Hey, the only thing holding you back is that you’re a raging asshole. And for 45 minutes, I was like, forget this person. She’s the pot calling the kettle black. She’s an [00:27:00] asshole. She’s an egotistical asshole also. And then finally at like the 46th minute, I was like, yeah, but you know, she’s right.

I am an asshole. Like, oh my God, I really am getting in my own way by thinking that I am, you know, by thinking that my shit doesn’t stink to, uh, to bring our crew story full circle. And here’s the thing. There’s a million things where that self awareness is helpful. The biggest one, or at least the most important one here is for delegation because I realized I’m not the best at everything.

And honestly, I’m not the best at almost like, I’m not the best at almost everything. I’m definitively not. So you’re

Steve Fretzin: not the best at most things.

Jordan Ostroff: Right. Correct. Thank you. That’s what I was trying to say. Right. So I need to find the things that I am actually the best at that I can focus on and I can find people who are the best at other things.

You know, I am not a details person. Good God. I have my wifi password written down next to my screen. I will not [00:28:00] remember it in any way, shape or form. I have whatever other notes for random things. So when it comes to like the specific technical stuff, I have somebody who’s really good with the specifics of lawmatic.

I can outline what I want the program to do. He can make it happen. Oh, we’ve got somebody in the firm is really good with practice Panther. I can help them outline what the workflows, you know, what the big picture is. They can build out the actual workflows. Like there are things like that where you need to know your own limitations and then you find people who.

Not do it 80 percent as well as you do it 120 percent as well as you and then you have them do it over and over and over again and your job is to help them get better at it, whether that’s feedback, whether that’s connecting them with other people to arm to help through that. So now they’re doing it 140 150 percent as well as you could have done it.

Now there’s that’s not going to apply to everything, but I promise you it will apply to most things like for me. I’m really short in emails. [00:29:00] I don’t mean to be rude, but it comes off that way because like, I don’t need to spend two hours a day on email. So now I have somebody who responds to most of my emails and they have a very specific system.

And I have had people reply back with like, Hey, your email seemed nicer. And I’m like, that’s because it’s not me. Um, you know, we, we built it out. So there’s little things like that where, you know, you’re not sacrificing the work. You’re empowering somebody else who is better at these things to do them better than you would.


Steve Fretzin: it started, it starts off with just identifying. We’re going to kind of wrap up on this, Jordan, but like identifying the things that you’re best at and maybe that you enjoy and then making a huge list of all the things you don’t enjoy and that you’re not very good at doing or that just aren’t in your best interest or skill set.

And then figuring out, is this a full time person internally? Is this a full time person externally? Is this a VA externally part time? And then looking at those resources, like get staffed up. Obviously, they’re sponsoring the show. They do. I, Sergio is my guy. I mean, he’s amazing. He does, you know, 40 hours a week for me consistently and, and.

He’s [00:30:00] just, I don’t have to tell him what to do anymore. He’s just on it.

Jordan Ostroff: Yes. And there’s always more work that can be done. So it’s, you know, it’s matching things together in the right skill set. If you’ve got somebody who’s super anal and pecky, put them in charge of the software. If you’ve got somebody who is super soft and caring and, you know, easy to chat with people, get them on the phone with clients at potential clients, former clients, current clients, as much as possible, like find these.

Archetypes by the

Steve Fretzin: stereotype, the people that fit best into the groove of what what you need felt and then

Jordan Ostroff: have them do the things that fit that skill set, you know, like, don’t take your best paralegal and turn her into your intake person because she was your best paralegal, because those might be totally different skillset, right?

You know, don’t take your best lawyer and turn him into the managing partner because he’s the best litigator. Like, find the, yeah. Things about them that will do well in the role you’re trying to fill, and it might be somebody who’s there, it might be somebody [00:31:00] who’s strongly in their current job, but becomes better by you moving them to something else that’s more in their skill set.

Steve Fretzin: Oh, really great, Jordan. Thanks so much, Ben. And I want you to talk for a minute. I already shared a great book about the four tendencies, the one that you. Put in as your game changing book is the is called delivering happiness. That was your like your favorite book for the year. Uh, talk about that.

Jordan Ostroff: Sure.

Uh, so Tony Hsieh, who unfortunately passed away on her like really weird. I don’t know if you read the story. No, he like died in a shed fire. It was like it was anyway, but he was found to his appos. And so like the book is really interesting in that it goes into a company that. Basically, Amazon bought them for all in a stock trade for an evaluation of over 1, 000, 000 solely because of great customer service.

And it was really amazing to me to hear how they kept that going as they continue to expand, you know, that adding that. Overnight shipping and adding, you know, and, and paying people. And if you, uh, get hired, they’ll pay like three grand to quit [00:32:00] when your first month or something like that. Like, it’s just fascinating to see.

They really want people that are truly committed do customer service as their unique selling proposition. So yeah, delivering happiness. Wow. It’s the best job I ever

Steve Fretzin: quit. Z Um, there you go, . And, and, um, wrapping up, I just wanna thank our, our wonderful sponsors of course, law Maddox, who got some shout outs today.

And also get stepped up. We got some shout outs today. So again, we’re talking about automations, delegations, things that are really benefiting. And, and of course, we want to thank green cardigan marketing with Ashley and her team. What an amazing group, uh, over there helping people with their strategy and phenomenal reporting.

Giving them, uh, actionable tips to take. Um, if people wanna get in touch with you, Jordan, they want to get, um, uh, and I didn’t even mention Jordan Ostroff, the owner of a lawyer with a life kind of skipped that whole thing, but I think you guys got a, got a handle on it. Um, so, so you’re coaching, so yeah, tell everybody what you’re doing and uh, how they get in touch with you.


Jordan Ostroff: man. So I am helping people run a business they can be proud of while living a life That’s even better. It is totally your version of my, of [00:33:00] my life, your version of my journey over the last, you know, let’s call it five years. Um, or so, and you can check me out at jordanostroth. com, O S T R O F F dot com.

Steve Fretzin: Very cool. Very cool. Well, thanks again, man. I mean, I, I hope we can continue to, you know, talk and hang out and refer and all that kind of fun stuff and have you back again at some point soon. But, uh, for, from my perspective, this was, this was everything and more that I wanted to get out of our, our chat today.

So thanks. Thanks so much. I appreciate

Jordan Ostroff: it. Thank you for having me as everybody who took the time to listen to watch this new year for 2024.

Steve Fretzin: Yeah, thank you. Everybody again, as Jordan mentioned for for hanging out with us and. I’m just taking in this content and understanding, you know, look, we’re all in, in this together for living the best life.

You get one shot at this thing. So, you know, you can keep, you know, making mistakes and not improving or keep going down paths without systems that aren’t getting you where you want to go, or you can step up and start learning from others and get coaching and read and do things that are going to benefit you and ultimately help you to be [00:34:00] that lawyer.

Someone who’s competent, organized and a skilled rainmaker. Here we go. Everybody, take care. Be safe. Be well. We will talk again soon.

Narrator: Thanks for listening To be that Lawyer life-changing strategies and resources for growing a successful law practice. Visit Steve’s website for additional information and to stay up to date on the latest legal business development and marketing trends. For more information and important links about today’s episode, check out today’s show notes.