Josh Monen opens up about his transition from senior copywriter who was booked out but working way too much to fractional CMO with productized offers, more time off, and a business closely aligned to the life he wants.

Josh didn’t need more clients. He needed different ones.

He didn’t need more ideas. He needed a clear roadmap with action steps he could put in his calendar.

During our one-on-one coaching engagement, Josh put in the work.

• He navigated hard conversations with dead-end clients.
• He created scalable, value-priced offers like Funnel Insights.
• He went through a paradigm shift and started selling leadership and advice, not just words.

More importantly, Josh stopped working Saturdays, started playing hockey again, and booked several long vacations with his family.

Was it easy? Of course not. It was a better, more satisfying kind of hard. Growth always is.

If you've hit a plateau, financially or emotionally, this conversation is the blueprint for what it can look like for a freelancer to move from selling implementation to selling strategy and advisory, without burning down a business you count on to pay the bills.

‍Key Points

• Booked out, but stuck: Josh was making good money and fully booked, but felt directionless and burnt out. He didn’t need more clients — he needed clarity.
• Desire for leverage: He wanted to evolve from copywriting into productized services, consulting, and fractional CMO work to create more time freedom.
• Indecision as the real bottleneck: His core problem wasn’t lack of opportunity — it was overthinking and analysis paralysis. Coaching helped him move from ideas to decisions.
• Created two scalable offers: Through coaching, Josh developed Funnel Insights and Funnel Blueprint — strategy-first services that led to $30K+ client engagements.
• From executor to advisor: By leading with strategy and positioning himself as a fractional CMO, Josh changed how clients viewed and engaged him.
• Lifestyle improvements: He now protects weekends, takes unplugged vacations, and feels more aligned with the freedom-focused business he originally wanted.
• Real ROI from discomfort: Investing in coaching created “point-of-no-return” momentum and helped him stretch into higher-leverage work.

Notable Quotes

“I was booked solid with copywriting and making good, consistent income — but more of my thing was like, ‘Where am I going with this?’ I felt like I kind of plateaued and was in maintenance mode.”

“If you’re making good money but don’t have time to enjoy it — what’s the point?”

“From that very first call, I was blown away. I even told my wife — ‘This guy really listens.’ And that’s rare. That’s one reason I hired you.”

Resources Mentioned

• Book a strategy call with Austin
• Austin Church on How and Why to Sell Strategy Engagements to Your Clients [Ed Gandia podcast]
• Josh’s podcast, The Way Of Kings
• Website: www.JoshuaMonen.com
• Twitter/X: @JoshMonen

Transcript

Austin

I’m so happy to have a conversation with you today. It’s been too long. For people who have no clue who you are, give them a little peek into what your career has looked like. 

Josh

Sure! I’m just looking at the calendar, about ready to  celebrate my freedom day - of quitting my corporate job back in 2011. May 25, I think.  But yeah, so before I got into this game, I spent five years in corporate America as an insurance agent, selling insurance from the cubicle. Did that whole thing, and decided I didn't want to do that for the rest of my life and didn't like to commute and wanted to have more freedom like a lot of us, right?

So I got into freelancing full-time back then, May 2011, and kind of fumbled my way around the first year, barely made any money. I was writing ads for cigars and random things and whatever came across my desk. So after that, I actually took  an in-house role  and  did that for a couple years while I built my freelance business on the side.  And that was good because I got some mentorship and learned about the marketing side of things, not just the copywriting. 

After that, I went back out on my own with a little bit more experience and know-how and  started just doing freelance copywriting in the insurance industry and that led to doing  freelancing for financial advisors and tax strategists, basically other financial kind of service providers. And that led into financial publishers and financial educators. So really the bulk of my career has been doing financial copywriting for the last 13 years.

I've done that and then a few years ago, got more into the consulting side of things. And that's, you know, part of the story where our story overlaps is wanting help and guidance with that and moving more into advising and consulting. So I started doing that a few years ago. And after I did coaching with you, I got that more refined and, and that's what I'm mainly doing right now. I still do a fair amount of copywriting, but now I have a good mix of advising and fractional CMO work in my career these days.

Austin

I think there’s this misconception that people only get help from a mentor, coach, or an advisor if they’re not making any money or enough money. If I recall, when you first reached out to me, that wasn’t the case. I think you were making what most people would consider really good money as predominantly a copywriter, sometimes you were doing copy critiquing or copy chief work too. But if it wasn’t just “Hey, I’m not earning enough,” what was going on in your business at the time that would make you reach out to someone?

Josh

Yeah, it's a good question. Cause I've been there for, needed help just making more money and booking myself solid. I had coaching on that in the past and it was good. But yeah, when I reached out to you though, that wasn't the case. I was booked solid with copywriting and like you said, making good, consistent income but more of my thing was like, “Where am I going with this?” I felt like I kind of plateaued and was in maintenance mode. And I just, for my personality, it wasn't good. I wasn't excited about what I was doing anymore. I needed a new mountain to climb a new dragon to slay. And so I wanted to work on my business more and really get into productized services and strategic consulting, things like that. Cause I would do that for clients, but I just wasn't calling myself that a lot. And that's why I think I was able to hold onto clients for so long and get referred a lot is cause like any good, I feel like copywriter isn't just a copywriter, right? They do play the role of advisor and things like that, but they don't always officially label themselves like that.

And so I wanted to do more of that. I wanted to create more leverage, and to have more freedom. I found myself working six days a week and long hours. And I was like, why? I was having less freedom. And that was counter to the whole reason I started doing this in the first place. And so I was like, wait a minute. Who cares if you're making good money if you don't have time to enjoy it.

And for me, I value time way more than money. I'm always looking for ways how I can buy back more of my time and, now with four kids and married and I love what I do. Some days more than others, some projects more than others, but I also want to able to enjoy life. I'm not one of those guys who wants to not work and figure out. I actually enjoy work, but I want it to be in balance where I can go do things I love. I want to go play hockey. I want to go play legos with the kids. I want to go on a hike. I want more of that. So that was a lot of the reasons that were driving me.

Austin

We have spent a lot of time together. I know this now - I didn’t then. Knowing what I know now, you could have figured out some of these problems on your own. You’re more than capable. You have the work ethic. You have the intelligence. You have the problem-solving aptitude. A lot of freelances, consultants, and fractionals, agency founders are in that same boat - where you can solve your own problems… Why hire a coach? Why reach out to someone like me who’s, in many respects, a peer - not like so far ahead of you. Why?

Josh 

Good question. I think it's like a lot of areas of life. I think about like when I got into strength training, I mean, I could have just read all the books and done all the things and figured out my own programs. I know I could do that, but I want to get the results faster. That's one reason, you know, so that's a reason.

And I know that I just get so close to my own problem that having that outside perspective is huge. And it doesn't need to be like someone who's way far beyond where you are. Sometimes I think someone who's a little bit closer to where you are, but just a little further ahead can be more helpful than the person who solved that problem 10, 20 years ago and they've been talking about it on stages ever since. You're like, okay, it just feels distant. Their stories and everything just versus the one who's like, hey, I just figured that out a year ago or 18 months ago or two years ago, I'm still figuring like, wow, that's actually more applicable, more tangible and helpful for me.

And I was in a spot too, where I was looking back, I was like, Hey, I haven't worked with a coach in a while. And I've always had good experience when I've hired coaches, I've got a good return on my investment. And I found myself like, wow, I haven't really had some one-on-one coaching in years. That's maybe that's why I'm feeling a little stuck again. I'm just in my own head, going through the same problems, revolving them in my mind over and over and journaling about them and just overanalyzing, overthinking. And I was ready to take some action and I was like, okay, well, I know if I make a financial investment and make the time investment and do it with someone who I feel like is good at what they do, then I'm confident I'm going to make progress faster than me trying to do it on my own.

Austin

I was going to ask a question about negative experiences with coaches. It sounds like yours have been mostly positive. Do you have any advice you would give to people who have either had a negative experience with a coach or have never worked with a mentor or a coach in a more formal capacity given that you seem to have had multiple successful relationships with coaches. Any advice that comes to mind?

Josh

I have to think about that. The people I've worked with have been  good for me. And I've tried to think of maybe a pattern in my decision making. And  I guess one thing is I have learned from them before, I got coached by them. Like, for example, you, I heard you on a podcast, and I think it was with Ed Gandia and I was like, wow, who is this guy? And I liked the way you thought about things, how you approach problems. I could just tell you what you thought just from that podcast. You're very open and just that conversation,  it just clicked like I want to connect with Austin. And other coaches in the past too, I had read their books or listened to their podcasts and I got a feel for how they thought about things. And so that made me comfortable reaching out.

And I think also knowing what you're trying to achieve is helpful. Like getting clear about what is your problem? Or like big picture, what are you trying to solve? And I guess if you don't know that there's life coaches out there that can help you with like even that, if you don't know what you want, like people can facilitate you getting clarity, but I think it's, career wise and where I've got coaching is like, okay, I have a more specific type of problem I'm trying to figure out here, who's really good at that? And then who do I resonate with? Who do I like? Who do I click with based on what I'm reading or what I'm hearing from them?

So yeah, I would say, do your due diligence and dig in. Most good coaches have put their thoughts out there and their personality out there, spend some time taking advantage of that and then say, “Hey, maybe I should have a call with this person.”

Austin

That’s a good word: due diligence. Once we make up our minds to do something, we may be tempted to just pull the trigger before we change our mind. I do want to point out that I’ve worked with a number of coaches too, and I try to talk myself out of it almost every time. When I have pulled the trigger, I’ve always seen the ROI. I’ve never regretted it. It wasn’t until I got into some work from a guy name Dr. Benjamin Hardy, who had done some research into creating a point of no return for yourself. The situation where you kinda have to get the results. He said that it’s actually more effective if there’s money on the line. Almost more than anything, money creates that point of no return situation. So it’s interesting to hear you say it and compare that with my own experience and be like yeah! It can still cause a bit of anxiety. I mean, none of us wants to make the wrong decision. None of us wants to lose money. But there comes that point in time when you have to put money down and create that point of no return situation for yourself.

If you were to summarize the problem that you were trying to solve at the time, do you remember what it was? I mean, I remember a little bit of it, so I could perhaps fill in some gaps. But how would you summarize that?

Josh

I would say one of the biggest problems I had was indecision, if I was to boil it down. I had so many options in front of me and things that I had dabbled in and kind of started. But then just analysis paralysis mode is what it felt like, so I feel like indecision was a big issue there.  And because I was trying to figure out, “How can I create these productized services?” I just was overthinking it and I could do it for other people and all this kind of stuff. But that was, I think a big thing is overcomplicating it in my own mind and just not making a decision because when it's just you and yourself, you don't always force yourself to make a decision. When someone asks you a question, you just asked me a question, I have to answer it. It's like I'm just thinking about this in my head. like, ah! I don't know. Maybe I'll come back to my own question later. I'm gonna go get some more, you know, it's just like… it forces what do you wanna do? What kind of productized service? Who is this for? What does that offer look like? Okay now I gotta engage and just make a decision. It sounds so simple, but I really feel like that was one of the big things I was struggling with.

Austin

That matches my own memory and also I’m really good at creating process for myself, and yet sometimes it’s really healthy for me to submit to someone else’s process, to trust someone else’s process, especially if that can short-circuit overthinking. You may have your own marketing or lead gen process, but sometimes it’s nice to just kind of show up at the gym and have that personal trainer tell you to do it this way, not necessarily the way you’re accustomed to, do it this way instead.

The other thing that comes to mind just based on what you said at the beginning was “I wanted to take more vacations… I don’t want to be working Saturdays much longer…” And I really admired your work ethic. It’s always fun for me to be like you are an amazing provider. You’re making high-integrity decisions in terms of keeping your commitments to clients, and also trying to keep your commitments to your family. But there comes a point in time where you’re like there’s not enough room for these other things in my life. That was one of the very first things we did was figure out what the growth strategy looked like so that you’re not working as many hours but you’re also not seeing a big dip in your income.

During that six-month engagement, which I think ours stretched more to more like seven and a half based on scheduling, do you remember some specific outcomes? I remember several, but when you look back at that experience, what did we do together? What did come out of it?

Josh

Just what you just talked about,  working back from there, like the vacations. I mean, that sounds simple, but I mean, I've been taking more time off and just getting it on the calendar. I think you were the one who first planted the seed of like the cruises, making a family cruise. At first I was like a cruise… I was like, I'm an introvert. I don't want to be on a boat with 5000 people. That sounds terrible, noisy and all this stuff. You're like just imagine, you don't have to think about the kids' food and everything. Like, oh, okay, now you got me.

So anyway, we ended up going on our first cruise at the end of that year. That was December and it was awesome. It was a one week cruise, went down to Roatan, couple ports in Mexico - completely unplugged. We didn't buy the Wi-Fi package. I just got some good reading time in, time with the family and it was so good. And and then before that, I took another like week or so off up in the Upper Peninsula in Michigan. We got a lake house. And just being able to get those things on the calendar was really helpful.

So just thinking about that making that commitment and now I'm not working Saturdays, which is great. I got Saturdays and Sundays off. And as far as some of the other work stuff that we worked on, the productized service, I've actually launched that. So Funnel Insights was one of the main things that I created out of the work that we did. And I've already sold several of those engagements and they've led to bigger engagements.

I actually haven't even told you this, but I did one probably a month ago for a client and these I just sell. I mean, right now my prices will probably increase, but they're $1,900 to do this, what I call funnel insights. We'll go and analyze someone's marketing funnel and give them a very thorough analysis and report and stuff like that. And show them which levers to pull to get a better return on their investment. And it's valuable in itself, but also it opens up opportunities for other things too, right? And so like that one I just sold a month ago. He turned around and said, Hey, how about you just build the whole thing? And it turned into a $30,000 job. And it was great because I've already done the blueprint. Actually, this one was sorry, this was a funnel blueprint. I have funnel insights and the funnel blueprint. So this one was a funnel blueprint, similar thing, but someone who doesn't have a funnel to blueprint it all out, and give it to him. And then, he turned around and now I'm working on the full promo and things like that. And partnering up with a  good friend of mine. So we're doing it together, which is fun. He's an Agora copywriter. And so I'm just being more creative with these kinds of  packages and what I've learned working with you even more is like starting these engagements off at the strategy level, at the advisory level just sets the tone. It's just different.

So I've done those, the funnel insights and funnel blueprint and done these strategy days, these in-person strategy days, which I love. I've only done a few of them, but they're great. I mean, a client flies into Austin. We spend a day and a half together. And I remember when I did the first one, I was a little nervous about like the agenda and I was like trying to cram all this stuff in and you were really helpful. Just helped me simplify, like, no, just  focus on the what on this day and the how on this day. And you shared some things that were helpful when you led those kinds of days and stuff like that was really, really valuable. So I was able to get some advice from you and do those days. And those engagements have led to other retainers and things like that too.

I'm just viewed differently in the eyes of my client because we started off with strategy, like before we just dive into the tactics and all the execution of everything, first, let's look at strategy. So those have been some really good tangible outcomes. I mean, the funnel insights, funnel blueprints, the marketing strategy days. And I do have fractional CMO clients now too. So I'm doing that  and I'm learning as I go, of course, like I emailed you not too long ago, like, man, I've been getting into the weeds too much with some of these clients. Cause I fall back to old tendencies of just like well, let me roll up my sleeves and go do this thing instead of advising on it and helping you hire someone, I'm like I want to go in and just let me just go write the copy because the copy needs to get done and we need to launch this… I have to remind myself to like restraint! So I'm learning.

Austin

It’s a constant learning and growth process. And this is not something that’s ever easy for a coach to say, but growth is by definition uncomfortable. It’s funny that you’d pay or I would pay someone to coach me and part of what I’m paying for is discomfort. Because they’re going to recommend that I do things that if they were comfortable, I would have done them already. But having someone who can gently but insistently push you into the areas or help you commit to the projects that are going to make you uncomfortable, force to stretch and grow… It’s kind of strange that we pay other people to do this with and for us and yet that’s one of the reasons coaches exist is because again, if it were easy we would have done it already. And sometimes we need people to come alongside us as say “Hey, it’s okay to want what you want. Here’s a way to achieve that.” I think you kind of alluded to this at the beginning, what’s next? There’s this paralyzing optionality. And to even just say, “It’s okay to want to play more hockey.”

Was it even a pivot necessarily or was it more just the next logical and natural progression in your career? What was it like to start thinking of yourself, positioning yourself, as a fractional CMO? As a part-time executive marketing leader?

Josh

It was different. It wasn't too daunting I guess for me. It was just different. I revamped my whole website and kind of stripped everything out of it that just screamed, Hey, I'll just do a project for you right away. So I went through and did that and maybe stripped it too much cause I'm like, Oh, I don't know if I have any testimonials  anymore. Maybe we should put a few things on there. Actually, I think I did add a couple, so I went through that process.

And yeah, it wasn't too crazy doing that. There was a scary time though… I actually just let a couple of my long time copywriting retainer clients go during this process. And that was scary. I'll admit, cause I'm like, well, that's where the bulk of my income's coming from. And there were some things that kind of came to head with one of them was like, you know what? I feel like it's time just to be done. And it happened a little bit sooner than I was planning, if you remember that. But I knew I was probably going to do that  a month or two months in the future, but some things happened where I was like, well, I guess I'm ready to do it now. So  that was a little scary, because I did see my income dip for a month or two as I was rebuilding and getting these other types of clients. So I had to go through that. Like, oh no, did I make the wrong decision and all these kind of things. So yeah, so that was a little scary.

And for me too, like I'm realizing I don't always have to be so all or nothing. I do that a lot where I'm like, okay, I'm just totally going to do this. Maybe that because I'm going to be 40 next month and I'm hopefully maturing a little bit in life. But yeah, just, okay, like some of these things can happen like in phases. It doesn't have to be…  like I'm still doing some copywriting work right now, but it's in a niche I'm really excited about. I'm writing a promotion about biblically responsible investing.  So I come up  Christian and I'm like, this is a fun area for me. I would be reading about this stuff anyways. I'd be reading these books anyway, you know? And so I'm able to apply even the copywriting to an area that I'm passionate about and stuff like that. And so, and I still have my advisory and fractional CMO stuff.

I'm learning it's okay to have some diversity in my career and have different kinds of client engagement. It doesn't just have to be fractional CMO all the way, or just copywriting all the way.  And you've taught me a lot about just thinking about things more creatively, even crafting offers and engagements and things you can use, bring our creativity to bear in that realm too, so it's been good.

Austin

You said a couple things. One, you can specialize but that doesn’t mean that you can’t take or go after other opportunities that come your way. That’s a common misconception, like a false dichotomy that if oh if I specialize, that means I’m pigeonholing myself, what if I get bored cause I’m only doing one kind of project? I don’t know anyone who’s very purposefully specialized, who isn’t also an opportunist and being like this project is cool! As far as I’m concerned, one of the goals of being self-employed, being a creative entrepreneur, is what you said, I’m getting paid to learn more about something I’m already interested in, how cool is that?

And the other thing you pointed out which I think is important to recognize is good coaches aren’t gonna give you advice that simply isn’t feasible for your life. Like I never work well with people who are like you just gotta do this thing. No, that just doesn’t make sense for my life because things have to be more gradual - I’m the primary breadwinner or I have health issues or whatever. It’s funny when people sometimes worry about entering a coaching relationship because they’re worried the coach is gonna pressure them into doing things they’re not ready to do, or is gonna insist that they be rash. Like leap before you look. My experience with coaches and the way I coach is the opposite. You meet every single person where they are. Yes, I’m gonna make you uncomfortable at times but I’m not gonna encourage you to do anything that’s just straight up stupid or harmful.

I want to shift gears, we’re almost finished, I’ve got two more questions for you. One of them is kind of funny but stick with me. If someone listening were in a position to help you, what’s a current need you have, and who makes a good client for you these days?

Josh

For me, what would help me? One of the things I guess I could use help with is I started a new podcast called The Way Of Kings with a friend of mine. And so that's a podcast for  people who are Christian entrepreneurs, they run an online business. And we're creating content and community and stuff for them. So if anyone has ideas of other podcasts we could be on or would be interested in being on ours. I want to spread the word. I mean, that would be something.

So good clients for me… if someone has like a funnel that they do feel like is underperforming and they are spending money on paid ads, usually at least $5,000, $10,000 a month on unpaid ads, and their funnel just feels like it's broken or could just be improved, and they want someone to really go in with a fine tooth comb and go through every part of that - the messaging, the upsells, what's missing - and they feel like they could get value out of that. That's also something. Or someone who wanna build a funnel, but they want the blueprint. They don't wanna just dive in and just start signing up for CRMs and hiring copywriters. They really want to blueprint that out just like you would a house before you start engaging in all the different trades and the contractors, if someone is in that phase two that's also something that I can add value to and be happy to talk to people. So yeah those are a couple things

Austin

Perfect! Thanks for sharing that. You never know who can help if you give them the chance to care. Where can people go online to find out more about you? You already mentioned the podcast. Is there a specific website or social profile where you want people to find you?

Josh

Yeah, my website's the best. Just my name, joshuamonan.com. That's my main place online. I have been absent from the social media conversation for years, but I've recently decided to start being active on Twitter aka X. So I think I'm just @JoshMonon there. So trying to be more consistent there. And that's my one social media outpost for now if you're on Twitter. send me a whatever you do on there, a message or a follow and or the website joshamonan.com or the The Way Of Kings too if you wanted to check out that podcast

Austin

Alright, this is off the cuff. If you could ensure that every new freelancer and consultant believes in one thing that would contribute to their long-term prospering, what would that one thing be?

Josh

I would say for freelancers specifically is if you can believe that you can get really good at prospecting and really good at your craft, you will have a thriving business. If you can believe, maybe that's two things, I can't pick one, but I think you need both of them. So just the whole be so good you can't ignore coupled with get really really really good at if you need to go out and kill something and bring it home and eat it, you will never worry about, like you have worries and stuff but you won't starve if you can do those two things.

Austin

Some people emphasize craft. Some people emphasize marketing. But you’re right in that if you can become very good at both, then you’re gonna be okay.

Alright! Josh, thank you for spending a little time with me sharing some of the stories about our work together, and some of your wisdom too. I really appreciate you. I look forward to seeing where you go from there.

Josh

Hey, definitely. It's always, always a pleasure. And I know you didn't ask this, but like if anyone is listening and considering maybe working with you or they get the chance, I definitely obviously would encourage that. And one thing I do want to say too that I didn't say earlier is  what I really noticed about you when we first met is you are a very, very good listener. And that's again, can sound overly simple and like whatever, doesn't everybody listen? No, they don't. And especially if you're working with a coach or an advisor, a lot of people have their pre-canned answers to things. Oh, you're doing this, do this. I never got that from you. Even from that very first call, I was blown away. I even told my wife, I was like, this guy really listens. Like I'm going to hire him. I told you what was going on and you actually listened. So anyway, I just wanted to get that in there and mention that that's important. And also if you're evaluating coaches and stuff like that too, I'll append my answer with that. But yeah, just wanted to mention that and again, it's been a pleasure. It's always good chatting with you, man.

Austin

Thank you so much. I appreciate all of your kind words. And I’ll talk to you soon.

Josh

Alright, sounds good. Bye.