Who to Trust When You’re Self Employed with Jenny Blake

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Who do you trust when you’re in business for yourself?

How do you know whom to trust? Not to mention trusting the market – but how exactly?

That was the main topic in my latest crossover episode with Jenny Blake, author of Free Time, host of the Free Time Podcast, and one of my favorite conversation partners.

We covered a lot of ground in this conversation, including: 

  • Why I say “Who cares?” all the time, what I mean by it and how it has freed me
  • Jenny’s (not so secret anymore) Substack – why she’s gripped by fear and what the fear says when it speaks – and how she is also thinking “who cares?” and "so what?"
  • The vicious cycle of what happens when the chips are down and how not to spiral down
  • How I’ve learned to trust myself – and which "self" are we talking about? Some really can’t be trusted :)
  • The old self vs. the new self – how do you even discern or know which one is present?
  • How I imported other people’s brains into my own as a way to learn to trust others, then myself. 
  • What happens when we are too attached to who we are. 
  • Inherently Confident? Is anyone born confident? What we need instead of confidence? Is it a byproduct and, if so, of what? 
  • How I decided to relocate to Savannah (and the baby steps I was instructed to take).
  • What made me so angry that I started my own business. The real story…
  • Why I say "yes" even when I don’t know how to do what I’m being asked to do. And why that is the essential attitude of a self employed person.
  • The connection between clutter and marketing.
  • Trusting the market.
  • Introverts are attuned to what people need, which is what it means to listen to the market (Listen to Episode 484 on how to listen to the market)
  • The antidote to the belief that you need to know things you don’t/can’t know yet. 
  • The beauty of the permission to “try it” (like a pilot project).
  • When you will know if your niche is (or isn’t) working.
  • Silence, ghosting and vanity metrics – plus, my favorite cognitive bias: absence blindness.
  • "Newsletter magic" and why it doesn’t matter what’s in your newsletter.
  • Why I put my phone number everywhere! Do people call?
  • The power of your voice in a sea of text.
  • What is the Magic Money Formula? How to use it to know how much marketing to do in your 30 minutes/day. 
  • How I use content to stay visible without driving myself crazy.
  • Quoting Jenn Lederer from Episode 483, "You will meet yourself."
  • The dream vs. the responsibility of self employment.
  • What to do when you’re surprised by a big bill.
  • How to know who to trust (and who not to trust) in a business situation.
  • Ilise's permissions: to listen to someone else and to do what someone else suggests.
  • Jenny’s permissions: choose something that’s vexing you and ask for ideas/input, even if you feel ashamed or nervous
  • Also, share honestly with trusted people about a mistake, stop keeping it all inside.
  • And more!

Listen here and below:

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Here's the transcript:

Who do you trust when you’re in business for yourself? Do you trust yourself? Do you trust others? And if so, which others? How do you know whom to trust? All very important questions that I think a lot about. Not to mention trusting the market that I keep telling you to listen to. If the market is going to guide you – and I think it should – you have to let it. But how exactly? That was the main topic in my latest crossover episode with Jenny Blake, author of Free Time, host of the Free Time Podcast, and one of my favorite conversation partners because she really does bring out the best in me, which we talked about too. So listen and learn.

Hi friends. Welcome back. I am delighted to be in conversation today with Ilise Benun. Ilise is the founder of Marketing Mentor. And we had so much fun doing our first round of podcast conversations with thanks to our mutual friend, Terry Trespicio, who introduced us. You can check those out in 165 on free time.

Are your clients bringing out the best in you? And episode 467 on marketing mentor on how to free your time. We had so much fun. We said, we got to do this again. Let's get on for just coffee talk. We have a few topics in mind about kinds of juicy things. So I'm just thrilled to have you back and vice versa, since we're recording this as a crossover.

So hi, Ilise. Hello, Jenny. So good to be back and talking with you and. You know, one of the things I actually, I think we talked about this too, is wanting to work with people who bring out the best in you. And there's just certain people who, when I talk to them, my excellent new ideas rise to the surface.

And that was my experience with you last time. So I'm looking forward to seeing what comes out of my mouth today. Ooh, I love that. Well, you really challenged me as well in a great way, talking about word of mouth marketing and you know, that alone cannot be a standalone strategy. So I learned just as much from you.

And I'm just so grateful to Terry for putting us in touch. In fact, we're recording this on a day, well, peak summer heat. My room is a sauna. I was telling you. Before we record, you're going to be a camp counselor again for her annual summer camp. And the theme of her summer camp is breaking the rules.

Your topic specifically is on trust and trusting ourselves. I would love to know how this particular topic bubbled up for you. So her version of my topic is the time you stopped giving a crap, basically. Because that's the format, the time, blah, blah, blah, dot, dot, dot. So everyone has the time. So that's my time.

And the more I thought about it, the more I realized, I mean, it came out of something that has almost become one of my signature quotes lately, which is, who cares? I say, who cares? Constantly. It can be misunderstood. It's very provocative. And so the thought was, let's try to dig into what it means when I say who cares and how it has freed me to not care.

And so the more I thought about it, the more I realized that who cares actually is a trust issue. And it has to do with so many different ways of trusting and things that can or cannot be trusted. And one of the ones that has occurred to me most recently is that when I say who cares, what I mean is, I don't know.

And whatever happened and whatever is going to happen, I have to trust that it's going to be fine. I'm going to be fine and I will figure something out because I am, as my teacher always told me, smart, resourceful, and there was one other thing, smart, resourceful, there's one other thing I am that makes me able to just say, who cares?

We'll figure it out. Where do we begin to list the other qualities? Smart, resourceful, creative, experienced, wise, improvisational. I love this. And of course, it's perfect timing because we were talking offline about how I'm just launching a secret sub stack for astute VIP listeners. I'm going to put a secret link in the show notes.

So you've got to dig to find it. And one of the things is I was having all these daily vulnerability hangovers, feeling totally gripped by fear, overwhelm, vulnerability, insecurity, just all the waves because it's very personal writing. And in one of the early posts, I write. Who cares? And I write it in all caps and I said, it is so exhausting to care.

So I love how you're framing this of who literally, who cares? And I, here I am. I'm so worried about what people are going to think. Are they going to judge me? Is my writing good enough? No, it's not good enough because I could list 10 sub stackers with better writing or smarter thinking or any laundry list of things.

And I say, we're not meant to compare ourselves to 8 billion people, which we now have access to seeing a good portion of them through social channels. And that if you really break it down, it's like, okay, maybe people see me for who I really am or what I really think or hard times that I'm going through or that my writing is filled with cliches.

Okay. Even if those things were true, which they may not be, who cares? Mike's so wide. I think Sometimes my mind goes to these worst case scenarios like, Oh, my clients or potential clients in community will lose respect for me and they'll unsubscribe in droves and I'll be left with the husk of a business.

That would be my fear talking. a result, but it could so easily go one of a hundred other ways. This phrase, who cares, which another way of saying it is what you said, so what, which is a little bit softer, right? I think it is so freeing. That's my experience, because the minute I realize, Oh, nobody really cares.

And yes, I am going to pick myself up. And figure it out. And that distracts me from all those big feelings that are getting in the way so that I can really focus on action because when something's happening, action is what we need. I do think that sometimes there's a vicious cycle in business, the psychology of running a business where if the chips are down, I tend to lose confidence and I get, want to crawl into my turtle shell.

And I also lose a little bit of trust in myself because I think, well, if I was so smart at business or if I took my own advice, maybe things wouldn't be going this way. A question I have for you is how do you trust yourself? And embrace the who cares, even when things aren't going the way you would like them to.

And this is something I've been giving a lot of thought to also. And one thought is that when we say trusting our self, which self are we talking about? And which selves cannot be trusted? And so I even made a list just off the top of my head of a few of the various selves, like the old self versus the new self or the rational self versus the irrational self.

And not even that it's binary, but like the desperate self, I'm not going to trust the desperate self or the self that wants something too much or the critical self. I would rather trust the compassionate self. And I even think like I have a morning self and an evening self and I totally trust the morning self and not so much the evening self.

That's hilarious. I don't trust my evening or afternoon self for that matter. I don't let my afternoon self participate in meetings because she's like hot and tired and over it. Yeah. And you're so right. I'm a terrible coach. If I do coaching sessions with a client, it has to be before a certain time in the day.

Otherwise I can't remember things. I don't have my words. I'm not nearly as sharp. So I love even thinking about the morning self and afternoon self or whatever listener, whatever your circadian rhythm would indicate. The idea there is that once you've identified which selves, and there are so many of them, right, we could make a long, long list of how many different selves there are, then We know which one's not to trust?

And then maybe we begin to think about how we might trust the ones that are left. And so to me, that first pass is the important one. I'm fascinated by the first one, the example you gave, the old self versus the new self. Sometimes in a liminal state, I find that it's not exactly clear which self is talking or which one's which, or which one even to trust.

Sometimes the new self is this reckless, excited risk taker, at least for me. That's how my new self comes in, like really wanting to go for it sometimes. So, do you have a recent example where you had even a debate between the old self and the new self and how did you discern the difference? Well, let me not answer exactly that question quite yet, because the thought that's coming to my mind is that that's a very common state, I think, especially when you're in that liminal state to not know.

Even be able to distinguish between the various selves and identify them that way. And that's where, from my experience, trusting other people and knowing who out there you can trust becomes paramount because my experience was that for years and years and years, I did not trust myself. I always made the wrong decisions in all aspects of my life.

I was okay. I got very lucky in many situations, but the decisions I made and remember I've been self employed for 35 years now. So you might think that first decision to go out on my own was a smart one, but it was really rooted in anger and nothing else. And it happened to be a good one, but it wasn't a rational decision at all.

And so little by little I found people outside of myself That I could trust, and as I began to trust them, I began to essentially import their brains into mine, which required letting go of the way I was thinking, that's the old self, and instead, agree to think the way they do, and that's very tricky, it took me, I don't know, 15 years to even begin to do that, But as soon as I did truthfully, things got better.

And so I saw that the way these other people are thinking is just smarter than the way I think, and I need to think like they think, and then. you know, it's really just a question of like remaking the new self based on teachers and mentors and people you admire and respect and then adapting what they're doing for myself.

That's the key part also, is you're not just following someone else's instructions. You have to integrate it and experiment. I like to say that your business. is a lab for your own personal growth, essentially. And so you experiment with things and then you see what works and what doesn't and what feels right.

But if we're too attached to who we are and how we do things and very rigid about it, then we can't let anything else in. I'm so curious to hear about the anger inducing incident that started your business. And I'm also curious back then, how did you know who you could trust? Because I always joke that I just had a faulty picker when I was in my twenties of who to date.

I really did trust the wrong people, my trust picker mechanism. wasn't great. It had to be developed. And I think that can happen too, in a business sense, because it's really easy to do what Mike Michalowicz calls keeping up with the entrepreneur Joneses and maybe trusting, or also like you said, kind of delegating the, Oh, how would you think about this?

How would you approach this to others? Sometimes for better, sometimes for worse. And just real quick before you respond. I can relate so much, and I'm so happy you brought this up because there's been areas of my life where I've been confident, but in many areas, I am not naturally inherently confident.

And it is not until I go to my trusted advisors and ask for input that I can move forward and even see what I'm not seeing about them. Qualities that would help me to move forward or that I can do something. And so I love that you've put words to this because I've never thought of it in quite this way, that there have been countless business decisions that I could not and would not have made if it weren't for the trusted advisors encouraging me, reflecting things to me along the way.

All right, first, I just want to say, I don't know anyone who is inherently confident. I don't think we are born with confidence in any way at all. And I personally don't love the conversation about confidence because I think confidence is a byproduct of action and experience. And it comes later. And if we think we need it first to do something, well, we're sabotaging ourselves essentially.

Totally agree. Right? And so courage is the word that often gets used kind of as a complementary idea here. And I think it does take courage to do the things that need to be done to trust someone based on Maybe it's a feeling, maybe it's someone else's referral, maybe it's something you can't even pinpoint and describe, but you're going to try it again.

You have to experiment, you've got to test it out little by little. Okay, here's an example. In, I think it was 2016, I had been living in Hoboken for almost 30 years. And I decided... Like, why am I still here? I don't understand. I know why I came here in the first place, but I don't know why I'm still here.

And it was just too cold. I'm from Southern California originally, and I just got tired of the cold. And so my teacher said to me, why don't you try Savannah? I don't know why he thought Savannah would be a good place for me, but I trusted him. Over the years, right? It took many years to trust him. And so he said, try Savannah.

So I did. And I was like, all right, well, I'm going to go spend the winter there. And he said, uh uh. You're going to spend one month first, the first winter. And then if you like it, you'll go back for two months. And if you like that, you'll go back for three months. And then you'll see how it goes. And then you can make a decision.

I was like, no, I want to go now. I want to spend the whole winter there now. And it's not like he was in charge, but, you know, if I was going to trust him, I was going to follow his guidance. And so I did it that way. And that was really the best way to do it because I got to see different neighborhoods. I got to dip my toe in the water and test it out before I made any big commitment to anything.

And I think We get very excited about things and we want to dive in and we think diving in is the right thing to do, but I'm really all about the baby steps and the testing and small bites before I make any decisions. I was used to quote Joan Baez, who said, action is the antidote to despair. That was like my living mantra, because it's so true that it's only taking the action, like you said, that any confidence.

And so that became one of my mantras for a long time. And I used to have these postcards that would say, build first, courage second, it's like, it's not the other way around. We'll be right back. Just after this.

So tell me, I just have to know, maybe your listeners have long since heard this story about what made you so angry that you started your own business? All right. Well, first of all. Well, it's helpful to know that I come from a family, a long line of self employed people. I wouldn't call them entrepreneurs necessarily, and this is actually maybe even before people thought about or talked about entrepreneurs, but everyone in my family essentially was self employed.

And so that's what I knew and that's what I grew up around and there was nothing scary about it to me, actually. And in fact, this morning I walked by a restaurant that was closed with my coffee and there was a little boy in the window and then he waved at me and I waved back and it brought back this flood of memories of Spending so many days during the summers in my grandmother's dress shop on Rodeo Drive in Beverly Hills, where before Beverly Hills was Beverly Hills and Rodeo Drive was Rodeo Drive, she had a dress shop called Sylvia Bender, that was her name.

And I used to go and spend time in the window, basically, and watch the people go by and pretend I was a mannequin. And, end. Who knows what I was doing, but I was just surrounded by self employment constantly in all of these environments. So that's my foundation. And so I went to college for Spanish. My degree is in Spanish.

I studied French as well. I had no idea what I was going to do. I moved to New York with a very good friend, and she basically got me my second job out of college. The first one was in the fashion industry, which is what my parents did, and I spent a year and a half working for a big buying office in New York.

I hated it, so I quit to become a waitress at Café Androit, one of my favorite places. And then my best friend said, well, we need someone to come in and do computer data entry at night. Would you do that? And this was like at the beginning of computers, 1985, 86, right around there. And so I said, sure, if you teach me, I'll do it.

And that's actually. A really important kind of reaction, I always try to say yes to things, even if I don't know how to do them because the no that comes from a lack of courage or lack of confidence gets in the way of being able to learn something new, actually. And so if someone is willing to give me a shot.

And it wasn't a secret that I didn't know how to do what they were asking, but even if it was after that, there were many times when people said, can you do this? I'm like, sure, I'll figure it out. And I think that attitude is just essential as a self employed person, because people are going to constantly ask you for things you're probably not prepared to do, or you're going to need to do things that you're not prepared to do.

And you're going to need to say yes, and then figure it out. So I just think that's a really important attitude. My best friend at the time had gotten me this job and it Essentially evolved into a full time job because then they offered me to be their operations manager, which I had no idea what that is either, but I said yes to it.

And it turned out to be kind of a marketing job and I didn't know anything about marketing there either, but I learned, and then I worked there for a year and a half and it just got a little political and on a personal level, my friend and I were, it was very up and down relationship and it. got to be very down.

And so I basically started doing bad things to get myself fired because I did not know how to quit that job. And I'm not going to go into detail about what I did, but let's just say one of them was I was also the bookkeeper. And I forgot to pay one of the tax bills, one of the quarterly tax bills, and the boss got mad.

And on a Friday, he basically just handed me an envelope and said, thank you very much. And that was in April of 1988. And at that point, because I didn't realize I had gotten myself fired, right. Because I didn't know how to quit. I saw that later, but basically I just thought, how dare he, and I'm never working for anyone again, and then I had to figure out what to do, but because he had given me a little bit of money in that envelope, which I thought was very generous.

I wasn't in a hurry and I could take my time and I went to my therapist and we talked about it and I just basically started listening to the market. I didn't know that's what I was doing at the time, but that was her suggestion, which is see what the world needs, see what people out there need people, you know, and that's what I started to do.

And. All the people around me were creative artists, actors, musicians, dancers, and I could see that they were very disorganized and I was a little bit more organized, you know, sometimes people call it anal. I'm not so much anymore, but that's the old self, not the new self. And I just started saying to people, Oh, well, I'll help you get organized with all your papers.

And people said, Oh, good idea. Let's do it for 15 an hour, essentially. And then little by little, I started to notice that at the bottom of everybody's pile, there was always something that had to do with marketing and self promotion that was not getting done. And it was just so consistent that I realized this is the main problem, but clutter is an obstacle to self promotion.

I can do that. I know how to. Get the word out. Let's just send stuff to people. That's really all it was. I love the mail and that's what I started doing. And that was the beginning of marketing mentor, essentially. That's incredible. And back to this topic of trust, how you say that you somehow knew even early on how to trust the market to tell you what was needed and that by taking on those early clients, you were able to see themes that were emerging and then trust yourself, not only.

To try to go this route in the first place, but then to trust that you were spotting the trends of what you could provide. Yes, but I didn't think of it that way at all. It didn't feel like an issue of trust. I was just really in tune with the people I knew. And what they need and often, you know, really sensitive introverts are very attuned to what people need.

And if you put your trust in that and just provide it, I think the rest, it doesn't happen by itself. You definitely have to do things, but the market tells you what it wants. The market guides you if you let it. Okay. That piece seems crucial. If you let it, what do you see among your clients today in terms of when they are leaning into that kind of mutual information exchange, let's say with the market, with their clients and where it goes wrong, let's say.

Like, when do people stop? With that trust and timing connection, where does it go wrong? I think what happens is there's this belief that I need to know. I need to know what I'm doing. I need to know what my niche is. I need, in order to go out there, put myself out there in the first place, I need everything to be clear.

I need all my ducks in a row. Those are some of the cliches, but I don't think so. I think if you approach it with this, who cares? Life is an experiment. My business is an experiment. Yes. It's going to support me. So it must support me, but you can't be so. fixated on knowing anything before you can actually know it.

And so that's the obstacle I see most people putting in front of them. And one of the things my teacher always said was, if I came to him with an idea, he was like, yeah, try it. That was the most beautiful thing he could ever say. Yeah, try it. And I tried it and it either worked or it didn't. And I learned something and it always kept getting better.

Is there ever a case not to try it? Like, have you ever gone wrong with the, yeah, try it or who cares? Not really. I can think of a time. I mean, again, if you follow the baby steps and you don't risk everything to try it, you just figure out what's the MVP, as they say, right? What's the minimum viable product or the minimum viable service, whatever you can do.

Then you'll get enough information and often people, you know, again, they want to know like, well, how long is it going to take? The thing that happens is that you will know much sooner if it's not working than if it is, you will get the messages like, no, that's not interesting. Or no, we don't have money for that.

Or what are you talking about? We don't understand. And that is the information that's important. You're not going to hear, oh my God, this is the best thing I have ever heard of. Yes. Go ahead. Right. That's not usually what happens. You know, I say in Pivot that a good pilot will teach you three E's. Do you enjoy this area?

Can you become an expert at it? And do you want to? And is there room to expand in the market and your business and your services? So I've always said the same thing too, that you have to think of pilots as, you know, Resources at the Kentucky Derby. Like you can't know who's going to win, which of your small pilots or projects are going to take off.

You really can't know. You need to have a few running in parallel and then they'll show you which one takes on a natural momentum of its own. And if you're enjoying it and you want to develop your expertise in that way, and there's room to expand and you're getting that feedback from the outside world.

That's when you can double down and that's when you can kind of pick the direction. So I find that that's always been helpful for people who are stuck, myself included. Yeah, I totally agree. And another element of the obstacle though, is that people don't trust the feedback or they have really unrealistic expectations of what the feedback is going to be.

And What's normal for a lot of feedback is silence and we seem to have very little tolerance for silence. And the thing about the silence though, when someone isn't responding yet, or when you don't get any likes on your post or any of those vanity metrics. The thing is that there's a lot happening out there in the silence that we are not aware of.

This is another, I may have mentioned last time, one of my favorite cognitive biases is absence blindness. That we don't see what's not there, but in the silence, things are happening. People are thinking and seeing, even if they're not commenting and liking, it's making an impact. You just don't know it.

And that's another thing you have to trust. Oh, absolutely. I'm so glad you're saying that because it reminds me of everybody uses the iceberg metaphor. There's what you see and then there's everything else below the surface. But I like the way James Clear talks about it in Atomic Habits. He talks about an ice cube melting and that let's say the room is a certain temperature and the ice cube is going nowhere.

But little by little, the room gets one degree warmer, one degree warmer, one degree warmer. You're not seeing any action for a long time. And then at some point, the temperature threshold changes enough and the ice cube turns instantly into water. But there's so long in that alchemical process where it looks like nothing is happening.

Yeah, and often one of the ways I think about this and talk about it is in terms of magic. It feels like magic then when something actually happens, even though it's not, it's just been marinating for a while. And you haven't seen it. For example, one of the marketing tools in my simplest marketing plan that I highly recommend people do kind of as a maintenance marketing is a newsletter.

We talked about newsletters last time as well, a monthly newsletter, a bimonthly newsletter, a quarterly newsletter, even whatever you can manage, but you have to stay visible. And often when you send your newsletter out. And if the right people are on your list, then someone will respond, no matter what you said in your newsletter and say, Oh, I've been thinking about you and meaning to reach out and I have a project.

So let's talk. And I call that newsletter magic because It feels like magic, but the truth is you've been cultivating and developing those relationships over time with your newsletter, even if people aren't loving it or telling you that they love it, things are happening and that you have to trust. It's so true how it feels like magic.

My metaphor for that is like Bluetooth devices. You got to be discoverable. So, you know, when you're trying to match two devices, one of them has to go into discoverability mode or they both do. And so a newsletter just keeps you discoverable, keeps that light flashing like, Hey, I'm ready to be found. And you're really, really good at that.

You help my gosh, you do this in so many ways, more than I could possibly be able to keep up with. One of the things that I found most interesting and that Terry even mentioned when she asked To make the introduction is that you put your phone number in your email signature, and I'm pretty sure your phone number is on your website and in your newsletter, like it's everywhere.

You're not shy about it. Now for someone like me, who's practically allergic to phone calls, if it's not a podcast recording, tell me how that is for you. Do people ever call you randomly? Is it ever too much? It's overwhelming. Like I would just love to hear about this aspect of putting yourself out there in that way.

It's so funny. Yeah. And I do put my phone number in. My FromLine also, it's not just in my newsletter, it's in my FromLine because I want it easy to find. And I will say that these days very few people call me, but it used to be when people were picking up the phone and not afraid to pick up the phone. I think at this point people seem to be afraid to pick up the phone if you haven't made an appointment with someone.

And maybe there's some merit to that, I don't know, we could discuss it. But I want to be available. I don't want to ever give off this feeling to anyone, prospects, clients, my market, the world, like I'm too busy. And so as we've talked about, I put a lot of cushion in my schedule so that I don't have to rush from one thing to the next.

So that I don't have to have that feeling of pressure. Cause I think a lot of the pressure that people feel is self imposed pressure, and we could do a lot to take it off of ourselves. And so one way is definitely just giving ourselves time. And so at this point, you know, most people are not calling me.

And when they do, they're so thrilled to reach me. And I love to be able to thrill people in that way. When I'm available, I will definitely pick up the phone. I don't care if it's a number that's in my contact list, somehow the phone knows potential spam. So I don't answer potential spam, but. If it's a number I don't know, I'll pick it up.

I can always say, sorry, can't talk now. I love it. I love the feeling of somebody being thrilled that you answer and there's a real person there. I learned a little delightful software tip from my friend, Alexandra Franzen, many years ago that sometimes for email replies, she uses a service called Vocaroo.

I'll put the link in the show notes. And Vocaroo allows you to record a short voice message and easily copy and paste a link. So without having to do the rigmarole of recording on your phone, uploading a file. You just send this Vokaroo link. And what's interesting is that the times that I use it are when maybe it's a long message or it's an important message from a friend or a potential client, and I just don't want to sit there typing out the email.

And so then I'll open Vokaroo, I'll record a voice memo. And sometimes it just blows people's minds, you know, they can't believe it's my voice. And again, whether it's a friend or someone potentially reaching out to join the community or something, it always comes across as delightful to them, which surprises me because I'm doing it because I don't want to type out a long email, you know, and it's easy and it is joyful and you can convey emotion through the voice, which is why we're here doing this.

But it's one of those examples of something that's really a win win in this way where you get to. Spark joy and create a connection that wouldn't otherwise be there. And that does break from the norms of how we communicate now. Yeah, I love that. I'm going to check out Vocaroo because I do think that our voice has so much power, especially when we're just swimming in a sea of text and images, the voice just communicates so much.

And there are other tools that I am often advising people to use and I don't think they do it very often because there's something a little scary, I guess, about actually putting your voice in a recording, but, you know, LinkedIn on the mobile app, you can send a voice message to someone through the messaging app.

And on LinkedIn also, one of the things I love is they have a little thing. I call it an audio intro. I think they call it something else because its original purpose was if you have a weird name, you can say it in 10 seconds. You have 10 seconds to say something and you can pronounce your name for people.

But I thought, Oh my God, that's an awesome marketing tool. Just put your elevator pitch there and a call to action. And so I've been teaching people how to do that. It's not that hard, but it's also something you can only do on the mobile app. That's so good. Okay, so what's yours? What's your 10 second? I can't remember.

But it's something like, I mean, I say something different every time I introduce myself, but it's something like, If you want better clients with bigger budgets, then sign up for my quick tips and you'll get the magic money formula worksheet. Actually, you know what? I should change it to that because that's definitely better.

And that's what I'm offering these days is my magic money formula worksheet. When people sign up for my quick tips, little plug there. Yeah. Oh, I love it. Okay. Okay. Well, now, you know, I got to ask you about that. What is the magic money formula? Give us a sneak peek. I know they'll have to download it, but here's that word magic again.

So I'm intrigued. All right. People are often asking me how much marketing they should do. And I can't answer that question until we know how much you want to make. So the magic money formula is essentially you figure out how much you want to bring in on a monthly basis. And then you figure out how many different types of projects will get you to that monthly number.

And then that helps you figure out how much marketing you need to do in order to get to that monthly number and helps you figure out your capacity as well. Because all of these things are connected. But I find many people compartmentalize almost everything and therefore don't see the connections between it all.

And so the goal of the formula. is to tell you how much marketing you need to do in your 30 minutes a day, which is what I recommend. That's really what works. And that may be enough for most people. And then what you do depends on what kind of clients you're trying to get and how much you need them to pay for each type of project.

But the whole thing is rooted in marketing, which is why when you sign up for my quick tips, which is my bi weekly every other week newsletter, and all you get are really quick tips to help you do something right now,

we'll be right back just after this.

Now you're on so many platforms and I know you're their marketing mentors, like you're so good at this. Do you have any systems on the back end that enable you to stay visible, discoverable and consistent in so many places on a regular basis? You know, I know you're all about systems, Jenny, and I'm a little bit older than you are.

And so I want to say no, actually, I have help. First of all, I have really good people. Who disseminate my content and most of it is through my blog, my newsletter and LinkedIn and YouTube. That's essentially where I am. I know it may seem like I'm everywhere, but that's really where I am. And as long as I put out a newsletter every other week, that's my system.

I know that's what I'm committed to. And then the rest gets chopped up and put out into All the other places. And that is really the strategy that I recommend in the simplest marketing Glenn too, by the way, which is create some content and then chop it up and repeat it, repurpose it so that you're not reinventing the wheel every single time it's exhausting.

And, you know, the internet is a content machine. It's a content monster. It's a hungry beast. And so you have to find ways to repurpose and reshare because, again, you know that people are not seeing everything and even if they saw it once they're not going to remember or maybe they want to be reminded so it reinforces the idea and it reinforces your branding.

I mean, repetition is everything when it comes to marketing. So I just try to create, you know, one big idea, every newsletter, and then disseminate it in lots of places. That's my system. And so the newsletter is the crux. If you're doing that and you're coming up with your big idea, you're on track. And then it goes out blog, podcast, YouTube, LinkedIn, et cetera.

Hmm. Fascinating. Okay. So is there anything else on this topic of building trust in yourself or knowing who to trust? If we circle back to where we started, that we haven't covered or that you think people miss, or kind of think about you where there's an opportunity to think about something differently.

I want to go back to the idea of where we started in a way, when not to trust yourself, because I think if people can make a list of the different selves or the different moments, even, because it's kind of micro moments. Like I know for myself, I always have a big, excited feeling about something new.

That's just my MO, but I know better than to trust taking action on that. And so, for example, I will always sleep on it. Yesterday, I was negotiating a speaking engagement, and they're having trouble coordinating with the date that we came up with, and the time, and the place, and all the logistics, and they came back to me and they said, Would you reconsider doing it on a different day?

I had already said no to, and I could have reacted from my evening self. So funny. Yes. My tired self. Yes. Right. I mean, if you ask me something at night, the answer is always no. So don't do that. And I'll even get enraged. Like if I read that at night after a long day and I'm tired and I feel I've already set a boundary, that's what will make me angry.

Oh, that's interesting. Yeah. Yeah, no, it didn't make me angry. I just knew I needed to sleep on it and I would have a clear perspective and thought in the morning and my thought was the same, it was still going to be, no, sorry, I can't do that, but I was much more polite about it in the morning than I would have been in the evening.

So I just think those moments, it's about getting to know yourself. Jen Lederer, another friend of Terry's, I met her recently and I'm going to have her on my podcast soon, actually. She's hysterical. And she said to me, starting your own business is a spiritual experience. You will meet yourself. And I love that so much.

I've been quoting her. All the time, because I do think it's true, whether to you, that's a spiritual experience or not is not the question. The question is, you will meet yourself and you have to be looking to meet yourself and not trying to be someone else and learning from all these little moments that it's going to surprise you what you find out about yourself and.

Really, when the rubber hits the road, as they say, and when the chips are down, how do you respond? That is yourself, and you could make a mistake and learn from it, or you could do the right thing, or you could just wait. until the moment is right to actually decide. That is such a powerful statement. I can see why you love it.

You will meet yourself. It's so true. And then part of the reason that's so powerful is that when you run your own business, really no one's coming to save you. You could say the universe, or if you believe in a higher power, okay, maybe yes, there will be grace or you'll be guided or your intuition will show you or inevitable serendipity popcorn will pop somewhere.

And at the same time. There's no one coming, like you have to confront yourself. You have to confront how it feels to be vulnerable or afraid or in a cash crunch or whatever the situation, like you're the only one who can get yourself out. So it's not like if you just wait for a long time or the paychecks keep coming and you can kind of punt certain feelings or sweep them under the rug.

There's no one coming. So it's like it requires this meeting yourself over and over and over again. And I think one thing people don't realize when they're dreaming of self employment is that the reality is, yes, there's all that freedom everybody talks about with a lot of hyperbole. Both you and I talk about the freedom and we're kind of spoiled by it by now.

But I think the part people don't talk about is the responsibility because you are responsible for absolutely everything. Even when someone else makes the mistake, even when someone on your team makes the mistake. I think I heard you say this recently. What could you have done to communicate more clearly so that that did not happen?

And how do you make sure that never happens again? Always. Yes. A hundred percent. Like just today I got surprised by a legal bill that I wasn't expecting and I kind of didn't think much of it. I was not venting to my VA, but I was just saying, Oh, did you see the bill? It's such a surprise. We got to cover this now.

Anyway, we're just chatting. And then she said something like. You know, it'd be great to get a quote for a flat fee next time in advance, just so you know what's coming. And it was such a great example of. Even this surprise could have been avoided and she was exactly right. And this is exactly how I encourage anyone on my team to think, which is, okay, this thing happened and it created friction or it surprised me not in a great way.

Now what? Okay, great. The next time I need to work on a contract renewal with a client or a legal issue or whatever, I need to ask for an estimate and a flat fee upfront. I can't just like let the clock roll, or at least I'm not in a position right now at this moment in time. And so. In this sense, when money is tight and a surprise happens, that's actually what starts the new system or makes us smarter at what to do next time.

Cause when times are really good, it's kind of easy. Things just roll and flow and you can be a little sloppy and things don't hit as hard. So that was exactly what you were talking about. Is there anything we missed on knowing when to trust others? I have a feeling you have some great rubric in there in that brilliant mind of yours of who not to trust.

I mean, we know the big red flags, but let's say in a business context, when do you know that someone is a true, wise, trusted advisor who can tell you what you might not be seeing for yourself? And when would you not let somebody's advice in? One of the things I think we need to be careful is someone who has too much at stake in the decisions that we are making.

And sometimes that could be a partner, right? Or someone in your family has some attachment to what you're deciding. And you want to trust the people who are closest to you, but sometimes they have the conflicts of interest and we don't see that. So that's one thing to make sure that there's enough objectivity.

Between you and the person who is advising you. That's what I would say. Okay, well, the last question that I ask always on free time, and I know this one's a crossover, is if you could give fellow small business owners permission to do something differently or drop something altogether, what would it be?

I would give permission to listen to someone else. Find someone. Try it. Find someone you think you might be able to trust. And just try something that they suggest and see what happens. I love that. And I'll build on your permission slip. I'll say. Choose something that's really vexing you that maybe you even feel a little bit vulnerable about, and you don't have to go this route.

But I always end up feeling very shy to ask for input, even from close friends, business friend, or it's been so rewarding when I put myself out there and ask for ideas or input on a situation, or what would you do if you were in my shoes or in your experience, what has worked for you? And I'm always so glad.

So even when I feel nervous to take a risk, Putting myself out there to ask for that input. I'm almost always so grateful on the other side, and I always take very interesting things away. Actually, you made me think of another one, if I may. Sure. Permission slip bonanza. Give yourself permission to share honestly with trusted people about a mistake that you made that you're especially embarrassed about.

Because I think when we're self employed and we keep it all inside, it's not healthy. And just the act of sharing it, even if you don't go into the gory details, you just say, Oh my God, I just made the biggest mistake. I need to get it off my chest. I think that is very helpful. So that's my other permission slide.

Okay. Well, now I'm going to build on that and just say, you know, the secret sub stack I've been so transparent in a very uncomfortable way, but I have to tell you, and the only reason I'm mentioning it again is that. Since the day I got some bad news and I felt like the sky was falling, I started writing.

And since I started writing, I have felt better every day. And yes, I have felt vulnerable. I say it's a 51, 49 ratio, 49 percent of me, speaking of parts, wants to take everything back down and Again, hide it from the outside world, but the 51 percent that's just tipping the scales toward courage. It's actually so healing to write about it and be honest about it and share more with people than I ever have.

There is something so freeing and healing for me in that process, even if nobody read it. And then I am hearing from people saying, thank you for being this open and this vulnerable, whatever. That's also something that really closes the loop is that we crave to hear the reality from other people because otherwise we feel very alone.

Like you said, it's a lot of pressure. There's a lot that we internalize in a bad way. It's like the pressure or the bad feelings kind of get stuck in our system. And it's so true that if you pick a mistake or something that's not going well and put that out there, it actually is incredibly freeing in a completely unexpected way.

Sorry just. Had to add that to say, yes, I'm going through it right now and I can confirm it's helpful. It's worth the risk. Definitely. Well, this has been so fun, Elyse. I just love our follow up coffee talk and we'll have to do another one again because I just love riffing with you on all these topics. Me too, Jenny.

It's been awesome. Thanks so much, Ilise, and big thanks to everybody who's here listening. Thank you.

Her “permission slips” are kind of like my baby steps and we shared a few of them – so take your pick! 

And if you want to build a thriving business on your own terms, the first step is to sign up for my Quick Tips at marketing-mentortips.com. Once you’re on the site, you’ll find lots more resources, including my Simplest Marketing Plan. Enjoy and I’ll see you next time. . 




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