165: Are Your Clients Bringing Out the Best in You? Engineering the Evolution of Your Business with Ilise Benun
8 Dec 2025 · 29 min
Ilise Benun on building a joyful creative business: vet clients so they bring out the best in you, price for an "aggravation factor," and use a three-step proposal process (discovery call, written proposal, walkthrough) to reduce stress and learn what works.
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People who don't bring out the best in you or who are kind of difficult or who are amateurs are. Are not bad people. I want to reinforce that it's not black and white. These are the good people, these are the bad people. I often feel sorry for them and if I can help, I will. But there are some people who just cannot be helped and you need to be able to recognize that right off the bat, especially as a coach.
This is your time. How can we earn twice as much in half the time with joy and ease while serving the highest good? That is our guiding question here at the Freetime Cafe, your home for heart based business. I'm your host, Jenny Blake. Join me for conversations with authors, friends and fellow business owners as we explore ways to free your mind, time and team to do your best work. Now onto today's show.
Welcome back, free Timers. I am so, so delighted to be here today with Elise Bennen. She is a mutual friend of previous guest Terry Trespicio who helped welcome free time into the world by hosting the IRL launch party in New York City. And Terri said you two have to meet. Elise is the founder ofmarketingment.com. there's a dash in the middle, the go to online resource for creative professionals who want better projects with bigger budgets through which she offers business coaching. She's also a national speaker, author of seven books including the Creative Professional Guide to Money, three online courses, and the Simplest Marketing Plan. She's just full of practical tactical tools to help build a joyful business, all of it tailored to the needs of creative professionals. She has also been hosting the Marketing mentor podcast since 2008 with over 465 episodes at the time of this recording and I'm honored to be on one of them. We've just been hanging out today recording podcasts. So Elise, welcome to the show.
Thank you Jenny. It's so good to be here.
I am thrilled to have you. Big thanks to Terri.
Again.
You start your podcast intro by saying that you help creative professionals get out of feast or famine syndrome. Can you describe that for us? I have a feeling we all have a visceral sense of what that means, but what do you see? How does that get expressed?
Yeah, that's when you have a lot of work at some point and you're so happy that you're so busy and you don't have to market yourself, and then suddenly the work ends or stops or the project ends. Nothing you did wrong. And suddenly you're in famine mode and you think, oh my God, this is the beginning of the end. And it just goes up and down like a roller coaster, over and over and over again. And often people can't figure out how to get themselves out of that spiral.
What do you find creates that spiral? So one of the things I heard you say is that it's thinking you don't need to do marketing while you're in the middle of working on a project or with a big client. What else contributes to entrepreneurs who find themselves in that position?
Yeah, it's not just thinking you don't have to, but also thinking you don't have time to. You couldn't possibly fit one more thing in, especially something you don't really enjoy. And that kind of goes against the grain of the work you want to do in the first place. And there's so many myths embedded in those ideas that I hear people express to me every single day. And one of the myths is that marketing is yucky, that sales is salesy and slimy, and I just don't want to do it because people are going to perceive me that way, and I don't want to be that guy. And I submit to all, all of you that it doesn't have to be that way and that there are lots of things you can do that bring yourself and everything you love and your enthusiasm into your marketing so that you stand out from all those other people who do kind of exactly what you do, but gives them a reason to connect with you and attracts the right people and gets you the jobs that will really be, to use your word, joyful.
You mentioned attracting the right people. I did a double take when I was reading your book, and there's this line, and it seems so simple and yet I don't think I've heard anybody ask this before. Are you working with amateur clients? We've talked about the business owner being at different levels of sophistication. You might be a newbie business owner, an amateur business builder, even an amateur marketer, but I've never heard somebody ask, are you working with amateur clients? What defines or describes an amateur client?
So let me lay a little foundation there to say that always when we talk to a prospect, whether that prospect is someone we pursued because we chose them and did a little marketing and introduced ourselves and they said, yeah, you know what, let's talk. Or they found you through word of mouth or some other content marketing perhaps that you're doing. Often people are very, let's say, self involved or self centered or self conscious and all they care about is I want this person to like me, I want this person to want me, I want this job. Instead of it's a two way street, it's an interview, it's not an audition. And the main thing I'm thinking of is who is this person? What kind of person am I dealing with here? And are we going to be able to work together? Are we going to be able to communicate and be productive and get something done that we'll both be proud of? So you have to start with that mindset. And one of the criteria I think about when I am interviewing people who could be prospects for me is is this someone who worked with people like me before and know what they need. Those are the professionals or who is an amateur who has not worked with someone like me before, who. And so their expectations are often unrealistic. And it's not like these are bad people. And I don't say I don't work with amateurs. But it's important to see very clearly who you're dealing with so that you can adjust not only your behavior and your service offering, but also your pricing so that it accommodates what you're going to need to put in to work with that person.
Right after that section of the book. You also talk about calculating the aggravation factor and it seems that even if someone is not an amateur client, they could still be aggravating. Does it make sense to work with a potentially aggravating client at all? Is it just when we get stuck, we don't realize up front? I mean, in this case you're saying calculate the aggravation factor. It's hard to say. And maybe we build that into the price. But what's your take on that? Is it even worth pricing a little higher if we spot aggravation factors or should we work to kind of remove those streams of clients altogether?
I think it depends on where you are in your business. If you need the work and your plate is not full and you don't have many options because your marketing machine isn't very robust yet, then I think it's perfectly fine to take clients who are going to be a little bit aggravating and learn how to deal with it. Because most people are actually very difficult for. From my Experience. And I think there are people out there who are what I call and think of the ideal clients. And everybody has to define that for themselves. But who really. For me, it's bring out the best in me. I want to work with people who bring out the best in me. And I'm willing to do what it takes, marketing wise, to find those people and bring them to me. And so if you put that effort in, then you can find those people. But if you aren't there yet with your business, and it really does take time and momentum to get there. If you're not there yet, then, yeah, just price in a little extra time and money time. Especially actually for the aggravation factor.
I had a very aggravating corporate client, and yet it was good money and I needed the money. So my mini business mastermind group helped me create a label that would automatically come onto their email when they emailed me that said bless their heart. And that was my homework. And it's kind of a tongue in cheek phrase. We all know it's only I see it. But the label says bless their heart. Like, it's okay. This one's a little more high maintenance. But remember, this is what they're paying for. Because it's the point where I didn't want to lose that business. And yet I needed to find a way to soothe the frustration that I had with so much of the communication style. And I love what you said of looking to work with people who bring out the best in me. The best in you. That's such a great frame to put around it.
And the people who don't bring out the best in you or who are kind of difficult or who are amateurs are not bad people, I want to reinforce that it's not black and white. These are the good people, these are the bad people. I often feel sorry for them. And if I can help, I will. But there are some people who just cannot be helped. And you need to be able to recognize that right off the bat, especially as a coach.
Part of prospecting for ideal clients is actually defining who they are. And I loved this episode you did. It was for a podcast called Marketing the Invisible on the proposal Oreo strategy. And I would love if you could tell us about the importance of an Oreo strategy that also involves us vetting prospects, not just the other way around.
Absolutely. So the proposal Oreo strategy basically means there are two cookies and the cream in between. And the two cookies are conversations, and the cream in between is the proposal document itself. So when someone says, can you send me a proposal for that. If it's someone you don't know, especially then, you don't say, oh, my God, they want me. Yes, I'm just going to put a proposal together, which is often what people do from that kind of desperate position which you don't want to communicate. So the first thing to do is the first cookie, cookie number one, which is essentially a discovery call, or I call a qualifying call, where you offer to chat for 10 or 15 or 30 minutes. I would say no more. Where you can again do this thing of who is this person I'm dealing with and do I want to work with them and can we communicate? So cookie number one is that conversation in which you also have to have the beginning, at least, of the money conversation, where you get a sense of either what's their budget or what number is in their head, or what's the value to the thing we're talking about that they're thinking about. So that if I write a proposal, the budget is not going to be the problem. You've already covered that in the conversation. And if you have a positive result of that conversation, then yes, you go ahead and you draft the proposal. But drafting the proposal doesn't necessarily mean you're now obligated to work with them if they say yes. And often people think that, oh, my God, I've done all this work, and now they say yes. And now I'm starting to feel like, no, maybe I don't want to do this project after all, or maybe I underbid it, or lots of other things that could happen. But anyway, cookie number two is. Is. And this is the trickiest one, but the most effective. I can't tell you how many clients these days are saying to me, I'm not doing any more proposals without cookie number two. And cookie number two is another conversation where you basically present in real time, whether on video or on the phone or some way, sometimes even creating a little video and sending it to them. That's a backup. But you essentially walk someone through your proposal verbally to make sure that they have read it. Because often people don't read the whole proposal. They've read it. They understand what they're getting. They're not confused by anything. And you can wrap up that call with a clear sense of this is either going to proceed or here's what's missing, and we need to do a revision. And that's why I call it a draft. It doesn't have to be a final proposal, but these conversations give you so much experience of the actual prospect that by the end of it you have a pretty clear sense of who you're dealing with. And this is anathema to so many people because they just want to rush through this whole piece of the process to get to the actual work. And when you do that, I really think you do a disservice to yourself especially, but also to the client and the project.
And I can just picture those times where I. You almost want to send the proposal and close your eyes and like, oh, I'm going to hope for the best. And as you said in that episode, and then you get ghosted by the client. Do you think it's tactical question, is it mandatory to be on video when you do that proposal walkthrough?
Not necessarily, no. I mean audio is fine. We just want to be in real time so that we can either see if the person fell off their chair or hear if they gasped when they saw the price, which they shouldn't because you've already talked about money. That's again a very important piece of the process. But I call what you're referring to throwing the proposal over the fence. And I think that often creates what I think of as self inflicted stress. Because then you start fantasizing about, I hope they like it and I hope the number is right and I blah, blah, blah, all of these things. And which is very stressful. As opposed to have the conversation be in reality and then you'll know, is the number too high? Is it too low? How are they thinking about it? Are they happy with it? What else do I need to do? It's all in reality. So self inflicted stress is about making stuff up. And real stress has to do with being in reality when something actually is stressful.
That's true. And then you get feedback of what you might do differently in a future proposal. Whereas when you just throw it over the fence, there's no learning. Because I've done that so many times in the past, throw it over the fence, I never hear from them again. And then I have no clue. Was it me? Was it them? Was it the offerings? Was it the budget? I have no clue.
So, and I love you're pointing out the idea of learning the importance of learning. Because part of the mindset I think is essential is that everything, and I mean everything is an experiment. Everything is practice, not the real thing. So every time I send a proposal, I'm just trying something out to see how it's going to work. And that brings the pressure down, it brings the stakes down. And it really creates a sense of perhaps ease. Again, to use one of the words you like to use around this prospecting idea. Like nothing is really for real. Everything is just practice until forever.
I love that. I love that. I know you've talked about it as business as a laboratory.
Exactly.
Such a great metaphor.
We'll be right back just after this.
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One of my favorite marketing approaches that just fits my personality is word of mouth marketing. And you have so many helpful frameworks. You've been in business over 35 years. You've had a consistent newsletter for over 20 years. I want to ask you about consistency in a moment. Do you have any frameworks for actually doubling down and leveraging word of mouth marketing? Because sometimes word of mouth feels like it's just a result of creating great work or shareable work. So are there ways that you engineer increase word of mouth in your business?
So again, a little context first. I often talk about word of mouth as taking whatever comes along. I don't glorify it the way often people do because as you say, it is in fact a result. It is not. Usually when people think of it and want it, they don't have to do anything to get it. So it's not real marketing in my vocabulary. But what you're asking for is, is there something you can actually do to create word of mouth marketing? And I do think there are things you can do, although I don't have a framework around it. Just because I'm trying to stay as far away from this idea of I don't have to do anything as if that's a good thing. Because what happens when people don't do anything is, is that if ultimately the work dries up at a certain point, that's just the ebb and flow of business. Things dry up and then you panic because you don't have anything in place and you don't know what to do. And relationships, it's all about relationships take time to build and cultivate and turn into projects. So word of mouth is usually very connected to feast or famine, actually. So with that said, is there something you can do to generate word of mouth marketing? I think there is, and I think it's related to just staying in touch with your network. And that can happen on LinkedIn by engaging, commenting, sharing, or it can happen in you mentioned my email newsletter. Quick tips from Marketing Mentor. That's the way I stay in touch with with all the people in my network. And it's gotten kind of wide over the 35 years. And actually that is an example of content marketing. So word of mouth marketing is actually using the three tools, or at least one of the three tools in the simplest marketing plan to stay visible and stay top of mind. And the way I like to frame this actually is it's not like, oh my God, they don't want to be on my list. They don't want another email from me. What am I going to say in my email? It's this is how you remove the burden off of your clients and prospects and everyone in your network of having to remember that you exist because you want to be there in their moment of need and out of sight is out of mind. So if you're not there consistently, they're going to totally forget about you. Nothing personal.
So speaking of your newsletter, how have you stayed consistent all this time and stayed top of mind? Like, have you in your 35 years of business or 20 years of newsletter or so many of podcasting, do you hit dips or plateaus where you just can't bring yourself to do it, or are you consistent and you show up no matter what, rain or shine? Just how I admire people who are unfailingly consistent for as long as you have been. Tell us your secrets.
I don't have any secrets, actually, Jenny. I think it's a function of my personality. I'm a content machine, so I have more ideas and possibilities in my mind than I can possibly handle. And so it's just part of what I do to create content and especially in my newsletter. And that is the attitude and the mindset that I'm trying to teach. Like it becomes part of your day to day that you see content everywhere, you hear content everywhere, and you're taking notes and you're writing things down so that you're not landing on a blank page when it's time to actually send something out. So I feel like marketing is often compartmentalized. Oh, I got to do my marketing. It's way over there. It's far away. I don't want to do it. No, it's integral to the doing of your business. Because the content ideas come from the market. They don't come from my head. That's why I have so many of them. I'm talking to people constantly. I'm talking to you. I've got so many ideas out of our conversations already that I'm never going to be able to turn into content. But, you know, I sit down and I am that way. I'm very disciplined. I've always been very disciplined. There's a line, actually, between discipline and rigidity. You have to not fall into rigidity about it. And that, to me, is the challenge, actually. But I am very disciplined, and I send my quick tips out every other week, and I do my podcast every other week, and that's just the way it is.
And do you have a certain ritual that's newsletter time, where you set up your environment, or is it a certain day and time of every other week?
No, there's no structure to it. And actually, I think you'll appreciate this. What I've noticed. So I've talked about engineering the evolution of my business, especially in this year and the previous year. I am changing everything and delegating almost everything so that I can focus on the things I do best. And the way I like to do that is just to give myself big blocks of time, whether it's a Sunday or two weeks in Arizona or whatever the amount of time is I've decided I'm going to take for myself. And. And then I just let it bubble up and I follow my curiosity and I let things marinate in my mind, and I'm not worried about holding on to a particular idea. Oh, my God, I gotta get that one. So I don't forget it. No. If it's important, if it has depth, it will come back to me. And when it's ready, it will come out kind of like a baby, I think. Although I've never had a baby, so I don't know, but. But that's my experience. So I just have to create these big blocks of time to Let it come up and out, and that's when I do it.
I love that episode of your show. I'll link to it in the show notes. Engineering the evolution of my business. It just. Oh, I just love how you described it and trying to delegate almost everything so you can focus on the things you do best. You mentioned, I think it was in that episode, you're embracing the German term eigenseit, meaning the time inherent to a process itself. How are you embracing that? What does that look like for you?
So, building on what I just said, this idea of things take the time they take. So I don't know how long it's going to take me to write a newsletter if I let it marinate in me long enough. It doesn't take long once it comes out. So I don't want to be premature about it, but. But I don't like to rush. I made a resolution last year that I'm never rushing again. And so far, so good because that just squashes my creativity. So I like to let things just take the time they take. And one of my pet peeves, actually, is when someone says, oh, that took longer than I thought it would. And I think, how do you know how long something is going to take? What could you possibly be basing that on? Unless it's some kind of wishful thinking that is perhaps not based in reality.
That's so good. And I love your resolution. I'm never rushing again. I remember reading Nassim Taleb, who wrote books like Black Swan and Fooled by Randomness. In one of those books, he says, I never run to the subway in New York. I never race to catch the train. There's always another one. It's not that far behind. And he made that commitment to never race to catch a train. And I think about it all the time because it's so easy to. And we can use the subway as a metaphor for the work to, like, race and think, oh, we missed it. Oh, and always have that clenched feeling and time scarce and rushed and hurried. I did an episode in the early days of this podcast on precrastination and just how much more relaxing it is. My husband, to this day, thanks me for changing his relationship to the airport, because it used to be like running through the airport in a panic, trying to skid onto the plane at the last second before the doors close. There's no room for error. Whereas I get there, like three hours early. I go enjoy the lounge. I make it a whole experience because we don't know what's Going to happen. Anything can happen. And I hate that feeling of being rushed or stressed if I get at all prevented. So thank you for sharing that resolution with us.
And even, you know, this idea of interstitial time between things, I mentioned that I like to add a cushion to everything that I do to before and after an appointment. And what I also don't do in that time is try to get something done that can't fit into that time frame. I just want to use that time to think and reflect and prepare hair and just be ready to be present for the next thing. And I think it's very tempting to say, oh, let me just check my email. Let me just respond to that person. No, I don't want to respond without thinking through and following up and checking to make sure that the autocorrect didn't write something I didn't mean.
I am so with you on this. I think of it as I call it time buffer or margin. But I like having buffer padding around everything. And as a testament to that, you and I both set up spaciousness interstitial time around. We recorded for your show and then mine and we both had an abundant 30 extra minutes that we agreed to use half of it and then give ourselves a 15 minute buffer before both of us have our next call. And so it allows us to just be at ease and adaptable and yeah, that. No need to rush and I'm totally with you. I don't want to do anything in the buffer. I get up, I walk around, I get a glass of water. I might go say hi to Michael or Ryder who are in the other room. Like, I don't want to get anything done. I'm not in the mood. I need to transition out of what I just did and then get in the mindset for whatever's coming next. So. Woman after my own heart in so many ways. Yes. Last question, Elise, for now, before we continue, because there's so much we can talk about. If you could give fellow business owners permission to do something differently or drop something altogether, what would it be?
I would have to say, it's that scolding voice in your head. I used to have it. I worked very hard over many years to get rid of it. And sometimes it manifests as imposter syndrome, what people call imposter syndrome. Sometimes it manifests as, oh my God, I can't believe I did it that way. Bad, bad, bad, or even seeing something as a failure. I had a client yesterday say to me, I failed at this. I'm like, I don't see it that way. I don't think so. Let's look at it a different way. So just this idea of stop with that voice. Everyone has their own version of it and you know it when you hear it. Can you stop with it and just speak to yourself with more grace, with more love, perhaps with more joy?
Beautifully said. Thank you so much Elise. I'll put everything in the show notes, but is there anywhere you want to send people to learn more and keep in touch?
The best way really is to sign up for my quick tips, which is at marketing-mentortips.com.
Wonderful. Thank you so much Elise for being here for such a joyful conversation. And big thanks to everybody who's here listening.
Oh it was so much fun, Jenny. Can't wait for the next time.
Likewise.
If you've listened this far, you get a gold star. Thank you.
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