Listen to this podcast Ep. 146: From Lawyer To Small Business Owner: How Jeremy Cline Found His Calling

Interviews, strategy and advice for building your online business with your host Trudy Rankin.

Trudy Rankin: Welcome to the Online Business Launchpad podcast. I'm your host Trudy Rankin, and today I have with me Jeremy Cline. And Jeremy is both a lawyer and he is the host of Change Work Life, which is a podcast that's all about beating the Sunday evening blues and enjoying Mondays again.

And I can remember a time in my life when I did not enjoy Mondays at all. Now they are the favorite day of the week for me, so, and I can talk about that later. It's really, really cool to be able to talk to somebody who's a fellow podcaster, who's interested in building an online business, and his podcast is all about interviewing ordinary people who have taken action to change the path of their career, because you can actually do that if you want to. And he also talks about the career coaches who help them.

So it's basically all about the changes that anyone can make to enjoy a better working life, whether that means altering a small day-to-day routine or making a major career shift or something in between.

So after spending about 15 years thinking about how he was helping other people reach their dreams, Jeremy started to wonder whether he was going to end his career thinking, really this is what I did with 40 years of working life. And so he started the Change Work Life podcast to find out what other alternatives there are out there. And that kind of flows along a little bit with kind of the journey that I had because I was in corporate for quite a while and Chief Information Officer type roles and always had that itch to just see what else I could do in terms of starting my own business.

And so we share a little bit of a common story, and I just thought you would really enjoy being able to listen to Jeremy talk about what he's done and how he's gotten to where he is and where he would like to go as he sort of goes on this journey of being an online business manager, leader, director, leading other people through his podcast to be able to achieve the goals they want.

So Jeremy, thank you so much for being on the podcast.

Jeremy Cline: It's a pleasure. Thank you so much for having me.

Trudy Rankin: So do you want to start out and just for the sake of our listeners, just talk a little bit about your career, kind of where you've got to where you are now, and what in the world was the trigger that really, really, really made you decide to go down this online business entrepreneur route?

How Coaching Transformed Jeremy Cline's Path From Lawyer to Entrepreneur

Jeremy Cline: Historically, I think my career had largely been a case of doing what I thought I should do, rather necessarily than doing what I really wanted to. So I think the idea of being a lawyer was put in my head when I was relatively young, like 14, 15, something like that. And I explored other possibilities, but that was the one I stuck with.

And it was very much the mentality of the time that you did well at school. You went to university, you got your degree, you got a good office job, corporate job, and then you did that for 40 years and then you retired. And the degree was interesting enough in parts. I didn't love it, but there were certainly bits that were interesting and I can probably say that for most of my work, actually, even when I started and you know, it should have been new and fun and exciting. But even when I was a a trainee lawyer, there were bits of it where I did just think this isn't terribly exciting, but you just kind of assume that it's going to get better or that this is just what work is. And the shift in thinking certainly happened quite gradually. I guess there was a subconscious part of me that was looking at alternatives.

And it started when I first started to look into the world of real estate investment. In my day job as a lawyer, I act for some you'd call 'em ultra high net worth individuals and families, and lots of them have interest in property and real estate. And so I thought, yeah, there might be something in this. So I started to learn a bit about it and found a podcast. And the podcast that I listened to in particular about that has a number of, it's not just property, it also talks about the business aspect, the mindset aspect, that sort of thing.

And the single book that changed my thinking was one recommended on that podcast. It's a book called Unscripted by MJ DeMarco. It's probably his slightly less famous sequel to Millionaire Fast Lane, which some of your listeners may well have heard of. And in that book, he essentially sends out a blueprint for running a business.

I mean, the first half of the book is essentially a rant. Why employed work is just a path to nowhere and it's not a good lifestyle. And he gives lots of fairly compelling reasons for shifting from that to business ownership. And I was sold, I was absolutely hooked. I thought, this sounds brilliant.

Yeah, this sounds like what I want to do, okay, how on earth am I going to do. I mean, okay, the idea to start a business, but then there's what businesses start with and you know, how you actually do it. And one of the points that was made in the book is that finding ideas for a business isn't all that difficult.

You just look for a pain point, something which is difficult in your life. So I started there and I had a few ideas. And I got my own first round of coaching at that point to help me figure out what I wanted to do. And the coach said to me, well, you know, instinctively, which one appeals to you?

And I said, start a podcast. Cuz at that stage I'd heard of people like John Lee Dumas, who have tens of thousands, hundreds of thousands of listens. And they, you know, they make their money through advertising and that kind of thing.

And I thought, Oh yeah, I'll start a podcast. I'll get a few tens of thousands of downloads per week and monetize it that way.

And I started the podcast and fairly swiftly realized that just getting into over a hundred downloads a week, let alone thousands or tens of thousands is really, really hard work, especially when you're starting from absolute zero. No one knows you. You have absolutely no authority or presence in this space at the moment.

And so yeah, I Started the podcast, which loved, but realized it wasn't much more than a glorified hobby. And that was what led to the second round of coaching which led to a realization slightly better. But I realized that I would like to do coaching. And so I started that about a year ago.

Trudy Rankin: I think that what you're saying is the path that a lot of people go down.

They start something. They work on it for a while, realize that there's a lot more to learn and there's a lot, it's a lot harder than you think. And yeah. How did you feel when that realization hit you? That it was just a hobby and not really a business?

Jeremy Cline:  It was, yeah, it was slightly depressing.

Definitely. In hindsight, it wasn't really surprising. I mean, I didn't go into this with a plan and that's probably the first bit of advice I'd give to anyone who wants to start a podcast is be very clear what it is you actually want it to do for you. Because I wasn't. I just had this idea that it was going to be something that would grow organically into this, you know, self-sustaining monster.

And it was an almost inevitable that it didn't, not because the world was against me or anything like that, but just because I didn't take action in that regard, you know? I would've needed to have done lots and lots of more work, lots of different things in order to turn it into that. And I didn't feel like that was necessarily right for me or I didn't really know how to do it.

I was basically kind of stuck. And it was when I realized that I was stuck, that I'd got this thing, but it wasn't, it didn't feel like it was moving me any closer to this goal of quitting. I should be doing something else that I had the second round of coaching, which was absolutely essential and absolutely pivotal for me just to get that clarity in my brain as to what I was going to do next.

Jeremy Cline: Cuz I'd, I'd had other ideas. I'd even started another business in the podcast transcription space. I mean, as you know, a lot of podcasters include full transcripts of their shows, and I'm quite picky. I want something which is going to be readable. You know, it could be freestanding and it was either paying a fortune for a human transcriptionist or having an AI version, which, well, the first time I did that, I started to tidy it up and just thought, I cannot do this. I cannot do this.

And so that was my first outsourcing. I hired a VA to help me tidy up the transcripts. But then I realized that I actually had a scalable solution, you know, the whole run it through AI, then get an individual to tidy it up for a fixed cost. That was something that as well as doing myself, I could offer it to other people.

So I started to do that and then quickly realized that I wasn't really enjoying it. And that was one of the aha moments. I realized that it wasn't enough just to have a good business idea. Cause I still think it's actually as a business model, it could be very effective, but it wasn't for me.

Trudy Rankin: Yeah, I can resonate with that very definitely. So, when you realized you weren't enjoying just that part of things, you know, doing transcripts for people, other people who are doing podcasts did you continue it on or did you just let it go? Did you hand it off to somebody else? How did you move from there into the sort of the coaching side of things after you'd had your, your own coaching?

Jeremy Cline: So I stopped that pretty much, and it was soon after that that I started the second, if you like, the deeper round of coaching. So the first round was kind of focused on starting with something. And it was fewer sessions. We didn't go in quite as deeply. But then I knew I needed something, something more, something bigger than that.

Discover How Jeremy Cline Found His Passion From Podcasting To Coaching

Jeremy Cline: And one of the great things, as you know about podcasting is that you get to meet a whole wide range of interesting and different people. And so I'd effectively already auditioned my coach because she'd been on my podcast and given a great interview. So I reached out to her and said, can you help me? And she said, well, yes, of course.

And so I started to work with her and we spent a good time doing work on myself. So figuring out things like my own strengths, my own weaknesses, my own limiting beliefs, my own things I like, things I don't like. And the biggest one for me was figuring out my values, which is always quite hard to explain to people.

But you know, these, these things which are important to you, which drive you. And it was really like the clouds parted because it was… I've got this list of values, actually. It's taped up on my wall cause it's so important to me. But it was when I did that, that it was obvious why the transcript business didn't feel a fit to me. And the big reason for that was that one of my top values is social connection, sort of community collaborating with people. I was just, you know, receiving audio, doing the stuff, sending back. Yeah, there'd be a bit of email communication here and there, but it wasn't really doing it for me.

What I really love is the conversations. It's the one-on-one connections with people like we're having here, this kind of thing. Having these deep, meaningful conversations, that really energizes me. And yeah, that was one of the things which made it clear why the transcription business wasn't going to work for me, but also was a good indicator for me why coaching was going to be something that I was interested.

Plus, I'd realized that I'd just always… you know, we did a lot of work sort of going through my you know, like my back catalog, the work I'd done, and just social situations and I realized that quite often I do just want to help people enjoy themselves and get the best out of themselves and have a good time.

It's a silly example, but when I was traveling in New Zealand and we had a… it was an organized tour and the bus driver was Maori. And I said to him, well, you know, whilst we're doing this, why don't you teach us a haka? So get the whole group together and teach us a haka.

Which he did. And it was an incredibly bonding experience for everyone. You know, we loved it. We were on, I forget which lake it was, but we were on the side of a lake and you know, we practiced it a few times and we did it there in this amazing background. And it was great. So it's always been in there in me, this sort of wanting to help people enjoy themselves, get the best outta themselves.

And so it was through that sort of work that I landed on offering coaching myself.
It is really,

Trudy Rankin: really interesting. It's interesting to me, especially that you almost unconsciously picked podcasting as a way of getting started, which does definitely, you know, expose you to people who are out there doing stuff, and it gives you a chance to have that sort of relationship and sort of get to know people through the whole podcasting process. That's kind of interesting. And I'm curious now that you've now started into the coaching side of things. What is it that you focus on? What kind of coaching do you do and who do you do for or with?

Jeremy Cline:  So I help people who are at … They're at an inflection point in their work, and it can be both career, job, employed work, or it can be entrepreneurship, small business. So just to give you a couple of examples to illustrate the sort of work I do, there's the client who has been working in IT for a few years, and it's not their love. They're sick of it. It's just not very interesting. But they don't really know what they want to focus on. You know, there's a whole world of stuff out there. What should I do? And so I've worked with people like that one in particular who was in IT to help them to figure out where they might focus on and doing the work on getting to know yourself, values, strength, and so on and so on. And he's now exploring a career in the fashion industry. So he's starting to look into that.

Another client who …she'd actually already been through her career change. She qualified as an architect and then shifted into marketing. So when we started working together, she was actually a marketing apprentice and what she wanted was some support, making this new career, making the best out of it, sort of letting go of the old baggage, figuring out how she could succeed in that, how she could make it her own, cuz you know, marketing again is a huge field, which way did she want to go?

And then one fond example on the entrepreneurship side. I have a client who has her own practice as a… she's a hypnotherapist, and she came to me saying, I can't carry on the way I am. I'm burning out. I'm working all the hours. I'm not doing the work I want to do. I'm doing it just at a very surface level.

I'm being bossed around by the people who are running my Facebook ads and all that kind of thing. I don't feel like I'm in control, just help. And one of the really interesting things with the way her thinking has shifted through the coaching was that she started by saying that she wanted to open this center, so she was going to have this center where she had other people in and you know, like a sort of a holistic health and wellness center kind of thing.

And then when we did the work on her values in particular, she realized that what was most important to her was mastery. And it wasn't the breadth, it was the depth. What she got most out of was going deep one-on-one with people. And so we've been yeah, we've been working on getting her practice so it more aligns with that as well as I've been helping her take control of the people who she's actually employing rather than letting them boss her around.
So those are the sorts of people that I work with.

Trudy Rankin: I think that's really kind of interesting because there's quite a wide range of different types of people with a different focus in what they're trying to do.

But as you said, the common thread seems to be inflection point where they've kind of got a tipping point where they've kind of gone, enough's enough. I've got to do something about this situation, not happy, what can I do? And being able to work with a coach to do that is really, really valuable.

Trudy Rankin: I'm curious in terms of sort of marrying up the concept of podcast and coaching, how does your podcast, or does your podcast help you in (A) finding clients and (B) serving your clients?

Jeremy Cline: First of all, I've created this body of resource, which I can use and I can put out there. So, you know, where do I look to find potential clients? Well, there's career discussion boards on places like Reddit, which has actually been, you know, it's not been a bad source of leads for me.

So, there are very typically variations around the same half dozen questions, which is great because it gives me ideas for what to focus in a podcast episode. And then when I see something posting about that, I can say, well, here's some ideas for you and you know, if you're interested here's an episode on my podcast. And obviously I try and keep it as non spammy as possible and make sure that there's enough value in the response itself. And I'm not just saying, Hey, yeah, go and look at my podcast, but there's that aspect. My podcast is also… yeah, I've got. A lead magnet on my website, so exercises that people can try to sort of get started with the thinking, and that's something which I advertise on the podcast and you know, in social media posts and that kind of thing. So I build up my email list that way.

So the podcast is kind of a hook. And it's also, I've found something really useful in coaching. So when someone says, oh, I've got a particular problem. I had, you know, someone the other day said, oh, I really need to update my LinkedIn profile, and I said, well, why don't you have a listen to this interview I did? I've got someone who talked… It was, you know, LinkedIn 101, this is how you build your profile kind of thing. So yeah it's kind of a lead generator. And also it gives me yeah, it gives me a bit of credibility, the fact that I've, you know, interviewed and had exposure, you know, I've curated this content, which is going to help people with these sorts of issues.

Delegating Tasks To Focus On Growth And Impact

Trudy Rankin: I'm curious, you know, because the process of creating a podcast or every podcast episode can be quite intensive, and you've said that you have gotten help, I think with at least getting your transcripts done. Do you still do any of the hands-on production of your podcast episode?

Jeremy Cline:  Certainly less than I used to. Transcripts was the first thing that I handed off very, very early cause I, I recognized just how painful that process was going to be of editing AI generated transcripts. It was a few, I can't remember, 20 odd, 30 odd episodes in, I handed off the editing.

You know, I was a competent enough editor, you know, within the bounds of fairly basic stuff. You know, I could use about 3% of the functionality of Audacity to edit my episodes. But again, I recognized that I wasn't going to make any progress in turning the podcast into any kind of business when I was on a hamster mill of record, edit, post, et cetera, et cetera, et cetera.

So I handed off the editing. Later on I handed off the show notes. So really all I do now, aside from the recording is I prepare the audiograms, I do these 60 second audiograms, which I post on social media. So I do those. I prepare social media posts and I do the posting on my websites, which again, is something that I could potentially hand off, but haven't got there yet.
So, ultimately, I think I would actually quite like to hand off some of those other aspects as well. And that's something that I'm seriously considering because it's stuff that, yes, I can do, I can do it reasonably competently, but it's not in my, it's not in my zone of genius, you know, that's really where I want to end up.

So yeah, it was an important realization that even though it had a cost and even though the podcast was generating absolutely zero in terms of any kind of income, it was an important realization that I had to invest. I had to pay someone else to do some of this stuff just to progress matters.

Trudy Rankin: Yeah. Yeah, definitely. And it's one of the things that I think people find the hardest to let go of. Certainly in my experience and talking to other people is that if you feel like there's money not coming in, you could have all lots of other kinds of benefits from a podcast, but if there's not money coming in to help pay for the outsourcing of the production side of it, it can be a while before people can actually get to the place where they can actually outsource some of it. But it's not a bad thing because it allows you to have control over the storyline that comes through in the podcast transcript, in the show notes and all those sorts of things.

Discover How Jeremy Cline Turns Leads Into Customers By Repurposing Podcast Content

Trudy Rankin: I'm curious, do you repurpose your podcast? So you've already mentioned show notes, you've mentioned your social media posts and your audiograms. Do you repurpose your podcasts in any other way to sort of, I guess, maximize the benefit of them?

Jeremy Cline:  Not nearly as much as I could. And this is something which is certainly evolving in my thoughts.

I mean, don't look to me for how to do social media, that's for sure. You know, there's the idea that you should only start with one platform. Well, you know, I'm on three and I don't show them an awful lot of love it has to be said. I mean, I post once every two weeks and that's when an episode comes out.

I post the 60 second audiogram for that episode and I include a brief description in the notes that accompany that audiogram and that description comes from the show notes. There's a whole lot more that I could do to repurpose, to make it more relevant. In fact, I was listening to, I forget the name of your guest, but an interview you did recently Canadian in Croatia, who does this kind of thing.

Oh, yes. Which made me maybe I should have a conversation with her because there's, you know, there's so much more I could do in terms of social media posting. And again, it comes to, is this something I want to do myself or is this something that I want to pay someone else to do who'll be able to do it much more effectively?

And the thing I need to get my head round is what's it going to do for me? I mean, if I'm now in a frame of mind where the most important thing for me at the moment is building up my coaching practice. I'm, you know, I'm still doing the law job three days a week. I do coaching, podcasting two days a week.

Ultimately, my aim is to transition into coaching full-time. Is spending money on someone to do social media promotion, that kind of thing, is it ultimately going to turn into getting clients? At the moment, I don't know. I should probably get some coaching on it. But yeah, that's the kind of thinking at the moment.

So I don't do it. It's definitely on my radar, but not necessarily something for me.

Trudy Rankin: Yeah, it's interesting to me because I think, certainly for me, it's been a bit of a journey because you can do some things fairly easily because I actually do a lot of it myself, and I'm only just starting to hand off some of the editing, but, I use Descript, which is a tool that lets me do everything all at once.

So it makes it really easy to create all of those extra bits of content really, the snippets that go onto social media, the transcripts, the show notes, the audio file, the video file that I put up on YouTube. But the one thing that I don't do, and that I've only just started to try and figure out how I could do that without moving away too far away from my budget is to actually take each transcript and turn it into a blog that's SEO optimized, and that's something that I'm still figuring out, but I'm close. I'm this close. I will get there with it. So I think for people listening, If you enjoy podcasting and talking, I think it's a really powerful way of creating what I call a content creation engine where you create something once and then you reuse it multiple times.

Trudy Rankin: It's the most efficient and effective way of doing that. And I'm interested in your experience in how you found the podcast to be useful in helping you find clients,. You know, you've talked about Reddit threads and things like that, but are there any other things that you found that help you with getting clients because of your podcast?

Jeremy Cline: Certainly as a lead generator. So the podcast has led onto my email list and yeah, I've certainly had clients through my email list. I mean, it's quite small, but it's growing gradually. Something I'm starting to do is going through my back catalog of episodes and seeing whether there's any potential clients in there or people who can refer clients. So I had a coffee yesterday actually with someone who was a guest on my podcast. You know, she's going great guns in what she's doing, but she might know people who can use my services. So it's just using podcasting is a fantastic networking tool. I mean, I've met so many people like you, who I never would've met had I not had my own podcast, had I not started down this online business journey.

And so it's kind of tapping into that network, not necessarily in the case of going back to previous guests and saying, Hey, do you want to buy my services? But just going, look, I'm doing this. This is the sort of person that I want to work with. This is how I can help them. Who do you know?

Trudy Rankin: It's a great tool. It really is a great tool to be able to help with that, isn't it? It really is. Yeah.

Insights On Transitioning From Being A Corporate Employee To A Business Owner

Trudy Rankin: I've got one more quick question cuz I'm looking at the time and it just flies away with us every single time I do a podcast. We could talk about these things for hours. But I'm interested for the benefit of people especially who are still either in the early stages of sort of establishing a business and making the apron string cut from corporate to their business or they're a ways along their journey, but they're still kind of doing both things. In terms of your journey and your thinking have you sat down and decided what your criteria is for when you're going to go, okay, that's enough of the legal side.

I'm going to move into my business side of things a hundred percent. And because I'm really confident that I can, or maybe not confident but you're just going to do it anyway, that you could actually make a living out of it?

Jeremy Cline:  Yeah, and I mean, certainly I can tell you what I've done. I mean, what I would say is that, some people, this will be a good approach. For some people, it won't be, I mean, at one end you can just quit. You know, the analogy is burning the boats. You know, you have to make it work. So that wasn't going to work for me. I wasn't going to put that pressure on myself or my family for that matter. So the way I've done it, which kind of reflects my personality really, is I've got an escape velocity figure in mind.

And my wife and I had a very long conversation about this. It's if I can sort of consistently do this amount on two days a week, and then one assumes that I could scale all that up to the same amount for five days a week, then it's a starting point figure. It's not a, this is where I want to end up, figure by no means, but it's a, okay, this would cover the outgoings.

It's just enough. That's the kind of like, alright, there's something in this. Off you go figure. When I'm going to get there. I don't know. It's it's like everything always takes longer than you expect it to. But yeah, that's the way that we've rationalized that one.

Trudy Rankin: Yeah, and it's different for everybody cuz I was one of the burn the boats people. And I wouldn't actually recommend it to anybody because you really do need to take time to build up skills. You're learning new skills all the time about being a small business owner that you don't get when you're in corporate. But if you are the sort of person where you are either a hundred percent in or you're a hundred percent out, you might have to do a burn the boats sort of a thing. Because when I'm focused on somebody else's business, I'm a hundred percent focused on somebody else's business and I needed to be able to do that for myself.

Trudy Rankin: One quick last question and that is that when it comes to… I was interested in, in what you were saying about the just personality and being able to understand your own values and, and then getting a fit between those values, kind of personality. You didn't say that specifically, but it's kind of there in what you were saying, personality, values and then what you do as a business. What would you say or what kind of advice would you give to somebody who's thinking about making the leap into their own business, whether they do it part-time or full-time, in terms of making sure they get that fit, that triangle fit straight from the very beginning.

Jeremy Cline:  Building that self-knowledge and self-awareness to begin with, I would say is really, really important. It's very, very easy to see what others are doing and appreciate the success that they have enjoyed, and to believe that the way to enjoy similar success is just to copy their playbook. Don't get me wrong, you can get great ideas from seeing what other people are doing, but it is not necessarily going to be right for you. And if it's not right for you, then it's going to be harder. It's going to be more stressful. It's going to be less enjoyable.

If you are working in a way doing things which align with those things, which you are good at, those things which you enjoy doing, and those things which align with your own personal values, it doesn't matter if it's not the way that someone else is doing things. Going back to the book I mentioned Unscripted by MJ DeMarco, he talks a lot about, you know, the exchange of time for money and the importance of trying to break that. And I absolutely get that. I mean, the idea of, you know, making money whilst you're asleep, be it through digital products or whatever, that's fine.

The way my coaching practice is currently set up, I'm exchanging time for money. And you know, I'm very conscious of that and there may be ways in the future that I can weaken, if not entirely break that link. But I'm doing something in a way which aligns more with me. So yes, coaching is a more people-oriented, more sort of time-based kind of thing.

It's much harder to productize. I mean, I have seen talk of AI coaching, which frankly slightly scares me, but yeah, I know from it… there was a great element of seduction. It was like, yes, I sh… And my first business ideas were, you know, it was like, marketplaces, online marketplaces where I could just earn affiliate revenue.

And I just looking back, it never really chonked with me cuz I just never, didn't really have a clue what I was doing and it just, it was completely beyond me. Whereas now I just feel so much more comfortable that I'm doing something that aligns better. So, it's something that you can do in whatever stage you're at really.

I mean, whether you are just starting out, whether you are further along, whether you are pivoting from a side hustle to take it full time. I can't stress how highly I believe that doing that work on yourself, getting to know yourself, it just makes things easier and more enjoyable.

Trudy Rankin: A hundred percent agree. Absolutely agree. It is critically important. Jeremy, it's been really great talking with you. If people were interested in finding out more about you or in getting in touch, where would they go?

Jeremy Cline: Yeah. Home base for me is my website, which is So change work life is all one word. There's a contact form on there. And also if people want to if they want to start this period of self-reflection, if they want to start to take a few baby steps there's a couple of exercises on there. It's And yeah, couple of exercises there, which just start you thinking down this process of self-reflection, self-knowledge, looking back at your past work history.

Look into the future, the sort of stuff you want to do. So yeah, happy if people want to check out those.

Trudy Rankin: Fantastic. Thank you so much, Jeremy. It's been great talking with you.

Jeremy Cline: Thank you so much for having me on.