How to Start Working for Yourself, with Bear Hebert

Does the idea of marketing yourself or selling something make you queasy? Do you already work for yourself and hate that part of it? It doesn’t have to be that way. In today’s conversation with anti-capitalist business coach and social educator Bear Hebert, we break down the reasons why working for yourself can actually be regenerative, beautiful, and subversive.

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A Wild New Work · How to Start Working for Yourself, with Bear Hebert

Introduction

Welcome to A Wild New Work, a podcast about how to divest from capitalism and the norms of modern work and step into the soulful calling of these times we live in. Which includes the call to rekindle our relationship with the Earth. I'm Megan Leatherman, a mother to two small kids, coach, writer, and amateur ecologist, living in the Pacific Northwest, and I'm your host today.

Hi, friend. Welcome. I'm so glad and honored that you're here, that we get to spend this time together. We are in the fullness of spring now. The days are long. There are possibilities opening left and right, things are in bloom. The first fruits might be coming in where you are, and I hope you're just feeling into all of the new ideas about yourself, about this world, about what could bloom for you, for us this summer, that those are just sort of wafting all around you and that you can tune into them as needed.

Most of you know that I work with people one on one through significant vocational transitions, career transitions, and soulful callings where something just is no longer working and we're being asked to step into different kind of work. And many of the people that I work with are trying to explore new pathways of earning a living ways that are less soul sucking than where they currently are, might have been, but that still enable them to meet their material needs. And one of the ways, of course, that people can earn a living and show up differently in the world is through starting a business. Through self-employment. So of course, this is something that I want to explore with people, usually, when they're my clients. I just wanna offer that as an option if they haven't really considered it before.

And one of the first objections I hear is something along the lines of, "oh, I could never talk about myself as much as I'd need to," or "I could never try to promote myself constantly," or "I could never sell something or sell my services to someone else." And I completely understand. I've been doing this for about eight years and I still get nervous and queasy sometimes.

I still am, you know, wrestling with marketing questions and have been greatly helped by today's guest. And so if you have said any of those things to yourself or had those thoughts when exploring the idea of starting a business or if you have those thoughts or say those things while you're in business already, you are in the right place today.

And before I introduce our guest, Bear Hebert, I just wanna remind you that this is the second to last week that registration is open for my summer solstice retreat on Wednesday, June 21st. This is an all day gathering in an old growth forest right alongside a river. And we will be crossing the threshold from spring to summer, really integrating what has come up for you in this season and casting a big, generous, spacious vision into your future so that you can feel more ease and alignment in your working life no matter where you are today. So in this day, I'll be teaching, there will be discussion, we'll be making things. My friend Heather is leading a forest therapy walk. Another friend Magda will be leading a floral workshop. We've got all the treats and goodies throughout the day, and it's just going to be very luscious and a space for you to drop in and come out with some new insights and new momentum.

You know, retreats and workshops and the things that we do are often helpful just because of what they are, like just on a surface material level, it just feels nice to be outside all day or with other people or making a floral bouquet. But we have to remember that there's also something happening beneath the surface, that we're creating different ripple effects, that the things that we do, the things we say, or explore, the commitments we make in these spaces are creating new momentum that we may not see the effects of right away, but that are surely happening. So come fill your cup. Of course. And my intention is that through this day you're creating some really different, serious, just beautiful momentum for you to lead you and carry you through the summer.

So, camping and hotel options are available nearby if you're coming from Seattle or Eugene or anywhere in the area. And I would just love to have you if the idea resonates and you could use it. You can learn more at awildnewwork.com/summer-retreat, and I'll put that link in the show notes for you.

So let me introduce Bear to you.

Bear Hebert is an anti-capitalist business coach and social justice educator. They've been self-employed since 2014 and now they help fellow small business people and other beloved weirdos figure out how to build the world yet to come inside the world that currently is. Bear believes that relational work is real work and emotional work is movement work. They're trying to help us all get a little more free.

Bear has been my own business coach, I have been in their marketing for Weirdos cohort, and I have just been so blessed by their perspective and their teachings. Bear has really helped me and helped me to embrace relating to business and those that I work with, with more humanity, with less striving, with less like gunk in the middle and just with a lot of care, and I'm really excited that you get to hear from them today.

So why don't I read our opening invocation for you and you can just settle in and we'll kind of set the tone for our time together. Taking a big, deep breath wherever you are. Just noticing what it's like to be in this body today and this time that you're in and the space that you're in.

May each of us be blessed and emboldened to do the work we're meant to do on this planet.

May our work honor our ancestors known and unknown, and may it be in harmony with all creatures that we share this earth with. I express gratitude for all of the technologies and gifts that have made this possible, and I'm grateful to the Cowlitz and Clackamas tribes, among many others, who are the original stewards of the land that I'm on.

Interview

Okay, Bear, thank you so much for being here and for sharing your wisdom and yourself with us today.

Bear: Yeah. Thanks so much for having me. It's a real pleasure.

Megan: So you have, from my perspective, a really interesting sort of, weaving together of interests and passions and skills and the way that you've brought those together, I think especially in the last like 10 years, is really interesting. And I would love if you could just give kind of an overview of where you've been and how your major sort of work endeavors fit together now.

Bear: So, you know, starting in the present, I'm a, you know, a anti-capitalist business coach, and if you had told me that that was what I was gonna be 10 or 15 years ago, I would've laughed at you.

So, you know, I sort of started my working life waiting tables. I, I worked in the restaurant world from like 17 through 30 something, waited tables for a long time and at some point in there I sort of knew that that was not like what I wanted to do with my whole life, but I was an artist. I was doing activism.

I didn't really see like a way to make a living doing the things that I was doing outside of work. And I started teaching yoga in 2008 and did that for a long time. Ultimately I quit in 2018 because of concerns about cultural appropriation, being a white person, trying to really be in right relationship with those practices.

So it's like, you know, waiting tables, started teaching yoga, also still waiting tables. Then started doing life coaching and that sort of happened organically too, where I was in relationship with a lot of my yoga students, and we weren't just talking about like how to move your body into these postures.

We were really talking about how to be a person in this world. And so I started doing life coaching as a sort of, you know, offshoot of the, the yoga teaching that I was doing, and found my first clients out of my community in New Orleans where I lived at the time and yeah, and then sort of again, organically, it turned out that after some years of doing life coaching, that many of my clients were coming to me with business questions and asking me questions about how are you using Instagram the way that you're using it, and how are you figuring out what to charge for these sessions? And like, can we talk about business more? And so I realized, "oh, this is also a thing that I could do. This is also an offering that I could have."

And so yeah, I sort of, you know, the, the, like, the slow fade from like waiting tables to teaching yoga, to life coaching, to business coaching is not really where I... I didn't start out thinking that I would end up here. And it also seems totally plausible to me that in five or 10 years I'll be doing something else entirely that will surprise me also. But yeah, and now I teach a lot of classes and that also happened organically. I teach business classes and really that came up because when I have client after client come to me with the same questions and I'm like, oh, I'm, I'm answering these same questions about this topic in the same way every time. Oh, I have something to teach here. There's like, you know, a broader audience that this might be useful for. So now I teach classes about marketing. I teach classes about pricing and, and then sort of as a side project, I do this other thing that's like undoing patriarchy classes.

So, you know, it's really been just sort of like following what's interesting to me, following what people seem excited by and really trying to find the overlap of those things.

Megan: Thank you. One of the things that I really appreciate about you, and I don't know if this, I think it's intentional, but that so much of your own, like inner work is tied into this, that it's not- and we'll talk about this more in a minute- but it's not just business coaching. I mean, you weave in like attachment, like the work that you've done with your identity and your attachment, and I feel like you really bring who you are into the work and you're very honest and transparent about that. This is all stuff that you have had to do.

I don't think you teach about anything that you haven't actually been through yourself, which is just good practice, but like, I don't know, there's a real depth to it with you, I think. And yeah, I guess - is that intentional or is it just the way you move in the world? I mean, can you say a little bit about that?

Bear: Yeah. I think that a lot of that has to do with my own kind of like relationship with schooling and credentials actually. Because, because when you asked that, the question that came up for me was like, "well, how else does anybody else do it?" Like, how is anybody else teaching or coaching about things that they haven't personally been through?

And the answer is they went to some credentialed institution who taught them how to deal with things that they themselves had not experienced. And so, you know, I do have a college degree, but I'm like the first person in my family to get a degree. I'm the first person in my family to, you know, pursue education in the way that I have.

I think I have a real inclination towards, yeah, towards like being self-taught and, and about the, the validity of the lived experience as a place to center our expertise. I think, you know, I don't know if it's because I grew up in a family where college was not like a thing, or like, because I'm queer, and so there's like all these things in terms of like heteronormativity that I've been excluded from, but I just have had a real sort of skepticism about the forces in the world that say, "this is how you become an expert at something." Like, conference of institutional value is how we know that you're trustworthy. And I've just sort of shrugged my shoulders at that, rolled my eyes at that a little bit. And yeah, I'm really interested in what it means for each of us to have lived through the things that we've lived through.

And then what do we have to offer because of that? Like what are the things you know that become unique to each of us because of our lives and because of the particular confluence of our identities and our experiences, our traumas, as you said, you know, like our, and our healing. And so I really try to bring all of that.

And it's funny to think about like all of that in the context of business coaching, but for most people that I work with, like their whole self is already showing up in how they're approaching their work. And so dealing with the whole person seems counterintuitive maybe, but actually I think helps people make a lot of progress.

Megan: Oh, definitely. I remember that was a big benefit of my time working with you one-on-one that, you know, it wasn't comfortable, but yeah, talking about like my style of attachment and how that might be translating to how I'm relating to clients and why I feel like I have to do a lot or earn their affection or whatever and yeah, it's completely related. That was impossible to separate, and I think just the way that you model that was so refreshing and is so refreshing.

One of the things that I have found really helpful, that has been like an anchor that I return to when I'm feeling really yucky about capitalism or like I don't know how to find my way through, is that you talk about the difference between capitalism and commerce. That commerce has been around kind of since civilization, really, since humans began like trading and being in relation in that way.

But that's different than capitalism. And I would love to hear more about how you define those two things, because I think it's a helpful way in for those of us who have to earn an income and wanna do so in less toxic ways. Can you tell us about that?

Bear: I love this question. I think it's such a clarifying one, not just for people who are in business, but for just like people who are trying to exist in the United States and, and in any place where capitalism is the economic system.

So yeah, commerce is defined as just like the buying and selling of goods and services. That's all it is. It's just buying and selling goods or services. Capitalism is an economic system that's based on the accumulation of capital. And what that means is basically it's an economic system that is based on making money by having the means of making more money, right?

So it's like how do you, how do you make more money inside capitalism? You own the means of production. That means like owning the factories or maintaining power over the labor force. You know, we could get much deeper into that, but capitalism is the sort of overarching economic system and commerce is like even broader than that.

Commerce happens inside all types of economic systems, not just inside capitalism. As you said, I think commerce is very old and capitalism has only existed for the last 500 years or so. So it's new. It's not the thing that people have always been doing. There was a time before capitalism and there will be a time after capitalism.

Commerce exists everywhere. So like in all places where people are engaging in relationality, in this way, commerce is a thing that's happening. People are buying and selling things even on a very small scale. And capitalism is not universal, right? So capitalism is not the thing that's happening everywhere. It is, you know, more and more a sort of organizing force in more and more places across the globe, but it isn't universal. Yeah. And then I think my like last kind of bullet point here about these two, and I'm happy to talk more about all of this, but is that commerce in and of itself morally neutral.

So buying and selling can be done in a way that is morally neutral or even morally good, at least in my opinion. And capitalism requires exploitation in order to function, which therefore makes it morally not neutral. Capitalism in and of itself requires that either we are exploiting the land, the resources, the people, in order for it to work.

It's inherent to the system in and of itself. And so buying and selling is neutral, and capitalism is not neutral.

Megan: It makes me think of this period like five years ago when I was exploring some of this and there was this whole thing of like "conscious capitalism," you know? And it's like there's no way, I mean, it's just not, like you said, it's an oxymoron.

And one of the things I love about kind of coming back to the idea of commerce is that it makes me feel free to like move in the world with less entanglement. I feel like when you take off the sort of moral weight of capitalism and feeling this pressure to like grow and exploit and like make it mechanical, I guess like capitalism, it's just, it's like a different sensation in my body. It just feels like, "oh, I can just be across the room or the screen from this person engaging in this thing that like can be okay," you know?

I think that is a, such a helpful way in to thinking about business and showing up in the world differently - that I can support myself in ways that are not necessarily harmful, even though we still live inside of capitalism.

What would you say to someone who has sort of thought about working for themselves or thought about starting a business but has a big, you know, "no" to the idea of like being a capitalist or like explaining yourself even and like marketing yourself in ways that aren't authentic, but I think the way you talk about business, it really can be a pathway to healing and to good in the world. So what are some reasons why someone might actually want to start a business? Even as things feel like they're on fire or falling apart?

Bear: And don't things feel like they are on fire and falling apart all at once right now? Yep. Yeah, I mean I think a lot of people start, are starting businesses these days out of necessity.

Just sort of wanna name that to begin with that like for a lot of people, they just need more money than whatever job they're currently working is paying them. And so people are starting side hustles and you know, additional businesses in order to just survive inside these systems. And I think that's especially true for people who are parenting or doing other kind of caregiving work where it's like, those needs are in competition with the requirements of working a more traditional job, and the same with people who have, you know, disability or mental illness or anything like that, where it's like, oh yeah, actually, like working a nine to five job and having to like show up in an office is just not plausible for people.

So I think there's a lot of, there's a lot of like really practical reasons why somebody might be interested in and trying to start a business at this point in time.

And then I think there's like also people who are are doing it because they're interested in doing work that is more meaningful. And one of the things about being in business for yourself is that like you get to choose what it is that you wanna do.

You know, that doesn't mean like any idea you have will therefore, you know, guarantee that you'll make a lot of money off of it. But like, you get to choose sort of how you wanna spend your time and, and what you wanna put your, your energy towards. So, that ability to be more creative inside the work, the ability to like diversify your income streams, like those feel like really good reasons why somebody might be interested in, in starting a business.

For me, those things were, were also part of why I wanted to go into business for myself. But a lot of it was just like feeling really, like I, I just couldn't see myself spending 40 plus hours a week working inside a system that I didn't believe in and doing things in ways that were like directly against the values that I hold.

And I feel that friction, and I feel the way that that impacts my body. I see the way that it impacts other people's lives, their spirits, their happiness, their, their health, you know? And so, yeah, for me being in business, it's not, it is in no way like, gonna solve the problems of the capitalist system in and of itself.

But it is a way on a small scale, or at least for me, running a business has been a way on a small scale, to get to actually enact some of the values that I hold in real life, in real time with other people, and to say, "this is how I wish the world was." "This is how I wish we could always be with each other."

And to get to create containers where that actually gets to happen. That's big, right? That's meaningful. That feels like little, tiny, practically oriented, world changing kind of work. And you know, again, it's not the be all end all. It's not the only way. It's not the only thing we need to do. You know, it's not like, oh, everybody goes, start a business and then you know, the end to systemic oppression.

But I think it is a potential real piece of that, of like, how do we let go of doing things in the way that we have been doing and how do we move towards a world that is more like the world we actually wanna live in?

Megan: I love all of that and it makes me think of how I was just talking to someone about how easy it can be to like actually build a toxic business for yourself.

That it's very easy to just build yourself another job, and that it actually takes a lot of intention and unlearning and relearning to build something that I think is what you're describing - this container where things are really different, and I think that's part of why your work feels so refreshing. I don't know anything about your astrological makeup, but it feels very like, you know, Scorpio and Taurus where you have like deconstructed business down to, it's like commerce bones or rebuilding it with like different language and different ways of relating to each other.

And that feels so different than if, you know, other solopreneurs who are just sort of doing it in the ways as if they were in a traditional workplace, you know? So I think this just takes a lot of intention and like, and kind of being an adult, like deciding for yourself, like how do you wanna move through the world and build a business?

And that can be a long, long process. Like, it's not something that happens overnight. Like I've worked for myself for eight years and I'm still like, learning and relearning. Are there like big buckets where you encourage people to start questioning, like, how we show up at work? Is it about your time management or like, it's like where can we start pulling the thread where this whole thing kind of comes apart?

Was there a thread that started for you where you started kind of the whole thing fell away and you could see that like, oh, business could actually be different. Does that give you anything to go off of?

Bear: Yes, yes. I have many things to say. Uh, first of all, I wanted to just side note for the astrology nerds listening, I'm a Scorpio Sun, Sagittarius rising, Aries Moon.

Yeah. I, I love this question of sort of like, how I'm interpreting this anyway is like, what are the kind of like principle shifts that happened that like led me down the path that I'm on and what are the, what are the shifts that I hope other people will sort of arrive at?

Yeah, I think one of them is like a really fundamental one in business is about, about how much money we need and I think that for me, getting 1) really clear about how much money I actually need to be, well, 2) giving myself permission to make that amount of money, and 3) doing that in a way that refuses to exploit other people in the pursuit of it, that's sort of the foundation of all the work that I do. I need a certain amount of money to survive. That amount may change over time. It has been higher in the past. It has been lower for periods, it's higher again, now, it'll be different for each of us, depending on cost of living, where you live, how many people you're trying to pay for, et cetera, et cetera.

But like, getting really clear about how much money do I actually need, so that's the math part, right? Which is like some, for some people, that's the easy part. For some people, that's the hard part. And then there's this like emotional piece that's like the attachment stuff, the healing stuff that's like "it is actually okay for me to need what I need."

It is actually okay for me to get the things that I need. It is okay for my needs to be met, and that has been just like, oh my God, like years long healing work for me to arrive at a place of like, no, it's, it's really okay for me to be well, and it's really okay for me to say, this is what I need. Even if my needs have not historically been met, even if I am a part of oppressed groups for whom their needs are often not met by culture and society, like even if it makes other people uncomfortable. It's still okay for me to need what I need and it's still okay for me to get what I need.

And alongside that, to hold this like sort of unwavering commitment to the fact that I'm not engaging in exploitation in order to get the things that I need as much as is possible, right? We could get into the real granular of like, I'm talking to you on a computer that was made with minerals that, you know, that like people were exploited to, to be able to be in this device that I'm, you know, we're recording this podcast on and so I'm not interested in moral purity.

But I am really interested in staying committed to the things that I believe in as much as I can. And so the fact that I can't be morally pure about it doesn't mean that I therefore can't try to do anything. And so, yeah, the money piece feels like a really huge one. I could keep going, but we could also pause because that was a lot.

Megan: Well, thank you for doing something so beautiful with that very tricky question. Yeah. Hearing you talk about needs made me think about one of the challenges that comes up for a lot of people that I think is also sort of rooted in class and access is the tension between starting a business and just going all in and like having needs and hoping the business, I guess, meets those needs as just that versus the idea of like starting small and kind of on the side and, and growing it over time, which also has its own challenges if you're working a full-time job and have little ones or a life and... building a business takes a ton of energy.

So one, just like naming those needs and like the internal work to just allow yourself to have those, I think is so refreshing. And then I think it also could open up more creativity about how to meet those needs. But what's your experience been like or what might you have to say about the options between starting a thing and sort of devoting yourself to it versus starting on the side and hoping it builds over time? I mean, any words of wisdom there?

Bear: Yeah. For me it definitely has been a sort of, you know, slow fade from one thing into the next, into the next, and arriving finally at a place where I'm making actually enough money has been, you know, a decade in the making.

And yeah, as a person who didn't have a safety net or a spouse or familial, you know, income or wealth or whatever to fall back on, you know, you sort of touched on that inside the question around class that it's like starting slow and building as I, as I went was out of necessity. And I think, you know, for a lot of people there's, there's no fast way to build an ethical business.

And that is just in direct contrast to so much bullshit that gets talked about in the online business world and in the like traditional business advice that you might read, that so much of what is getting sold is speed of growth at all costs. And I'm just not interested in that. I just don't think that's healthy for us.

I don't think it's healthy for each other. I don't think it's healthy for the planet. There's like so many ways that that slowing down just makes space for things to happen in a better way, in a more ethical way, in a more relational way, in a less exploitative way. Yeah. I've lost track of what the question was, but I hope that that was helpful in some way.

Megan: Yeah, definitely. I think it's permission to start slow on the side and meet your needs financially through a job if you have to, or waiting tables or whatever you need to do. And that it doesn't mean you can't eventually build something that can sustain you on its own. I think people just need to hear that, honestly.

Yeah, and I just,

Bear: I mean, I feel like I've said this a lot, but I just like, I really wanna remind people that like building a business takes time and like particularly building a business that is thriving enough to fully support you on its own, just takes time. And anybody who's trying to tell you otherwise is trying to sell you the thing that they think is gonna help you to do it faster. There are many ways to make a lot of money quick. That's true. There are plenty of ways to make a lot of money quick, but there are not, so far, I have not come up with any ways to like ethically build a sustainable long-term business very fast. It just takes time to do it.

And so if it is taking time for you, it's not a personal failure. It's not because you didn't manifest hard enough or you haven't, you know, taken the right class or whatever. And you know, there may be mindset work that needs to happen and there may be skill building technically that needs to happen, but like, yeah, it's just not.. The people who make a lot of money really fast in business are people who had a lot of money to begin with, and that's not most of us. So if it's taking you a long time, it's okay. It's not you, it's the system.

Megan: So, what are some of the other internal challenges that you bump up against in business coaching that like, I mean, there's so many, no matter how long you've been working for yourself, but what are some of the primary internal challenges that you see when someone begins the path of starting or working on their business?

We talked about like having needs and allowing those to be met and being okay with that, but there's so many, you know... when people mention to me that they have thought about entrepreneurship, the first thing I hear is that they hate marketing themselves or that they, you know, if they don't like selling, they hate the idea of that.

What are some of the big ones that you hear and what could you share about how maybe to subvert those or look at those or untangle them?

Bear: Whenever people say they hate selling, what I hear is that so much of our experience with selling and being sold to is manipulation and like lack of consent. And so of course you don't wanna do that because like, oh my God, I don't wanna manipulate anybody. I don't wanna like override anybody's consent. And so, I guess I just wanna start by saying I think people's resistance is like valid and based on real life experiences inside capitalism, but again, commerce can be a separate thing.

And I think it is possible to do commerce without manipulation and to do commerce without, you know, in a very consent based way without overriding anybody else's, you know, needs, desires, whims, et cetera. So yeah, the, the sales piece, I feel like some of that is just, you know, shifting our own kind of perspective about what's possible inside of buying and selling, that it is actually possible to do that in a way that could be generative, that could be reciprocal, that could be good for all parties involved, and the planet and our future. Maybe there's some grief work inside of that for like the ways that capitalism has screwed us all over.

I think another thing I see a lot of, yeah, in terms of marketing is, is just people don't feel good about being seen. You know, Brene Brown talks about the like voice inside our head that says, "who do you think you are?" And I think that voice is especially loud for people who have had experiences of marginalization. A couple of months ago, Kelly Diels wrote a really great blog post about how marketing and visibility is like asking for power inside a system that doesn't wanna give you any, right?

So like if you are a woman or a person of color, or a queer person or a trans person, or like whatever other, you know, set of marginalized identities, culturally, other people control the narrative about you. Other people have a lot of power over you, your life, your livelihood. And so to say, "I'm gonna stand here and talk about myself, I'm gonna stand here and tell you the story about me." Like, "I get to control the narrative." That an ethical power grab to say the power actually belonged here with me all along. And it's been, you know, overridden by the powers that be inside our culture.

And so that, that piece about marketing where it's like, oh yeah, like, actually marketing can be terrifying, but also it could be empowering. Marketing could be a really powerful way to connect with other people authentically about the things that we care about. And again, I think it can be ethical. You know, I think it's possible to do marketing in a way that is just about trying to provide people with information so that they can make a consensual choice about if they wanna buy from you, if they wanna be sold to. It can be fun. It can be interesting and it can, you know, I think it really can be generative. Yeah.

And then the last one that I think of here is just like, I think inside of capitalism we have such a sort of relational habit of either trying to get one over on the other person, or a fear of the other person trying to get one over on us, that we can end up in a sort of default power struggle with our clients, with our audience, with the people that we're working with. And you know, capitalism really entrenches this. It says that like, "the only way for me to win is for you to lose."

And if you're winning, it means I'm losing. And that is just not the way that it has to be. And so, you know, in our policies and the way that we build the structures of our, our offerings, like we can really put things into place that make it so that we're reciprocal. We're consent based. We're like really transparent, and that it gets outta those kinds of, you know, habitual ways of relating that are about exploitation and about, you know, fear and, and, you know, all that other junkie monkey stuff that makes us so averse to doing any of these things.

Megan: I'm thinking about how we can become people who have the capacity to do that because, there's the challenge of like never wanting to be seen and be like, "Ooh, I don't wanna, you know, bother you or ask for your consent to sell this thing to you." Or there's the, the other way we can go, which is like just sort of overriding that consent and, you know, doing the marketing that you mentioned feels so toxic.

How have you become someone who is capable of saying with a lot of like, confidence and stability, "this is what I do, this is what I sell. Do you want to hear about it?" And sort of being okay with whatever the response is. I mean, that's, that's like pretty meaningful personal growth and strength. And not to say that anyone has to be perfect at this, but what are the things like outside of your business that have enabled you to become someone who can do that?

Bear: All the things that I needed when I was a kid that I didn't get chased me into adulthood in ways that for a long time I was not aware of.

And so I was trying so hard to get those needs met by everyone around me, by anyone who I would engage with. And it made for really toxic dynamics because... I once drew this Venn diagram that I reference in my own mind all the time. That's like a two circle Venn diagram. And it's like the things that are reasonable for a child to expect of their caregivers, and then the things that are reasonable for adults to expect of other adults.

And there's like not actually that much overlap between these two circles, you know? And you can, like, negotiate with people to, with your intimate partners, with your closest friends, with your family, to like have more of the circles overlap. But like in reality, there's not a lot that's in that center place.

And so if I was showing up into my, you know, client relationships on a sales call, trying to see if somebody wants to hire me as their coach, and I'm feeling subconsciously the terror that perhaps my most basic needs will not be met, I'm gonna be bringing that into the conversation that I have with this other person.

And so, of course, I can't then have a healthy, helpful coaching relationship with them, you know? And so through a lot of years of therapy, 12 step work, reading a lot of books, crying, a lot of journaling, spending time with trees, spending time with the ocean, working with plant medicine, like so many things, right? Like long meandering conversations with friends, terrible dating relationships, like so many things have taught me how to heal this stuff so that I have like really done, I mean, just an immense amount of grief work around the unmet- ness of those needs so that then I can show up into these real-time interactions with people and go like, "Wow. Yeah, like some part of me will always be sad that I didn't get that. And also, I can hold that and not need that other person to meet that for me. I can like hold my sadness. I can hold my grief without then requiring the person on the other end of the line to show up for that consciously or unconsciously."

And so there's like a real sort of, I hesitate to use this word, but the one that comes to mind right now is like cleanness. There is like a, there is just like a cleanness of the energy that like, I'm not trying to like get you to... I'm not outsourcing my boundaries to you. I'm not trying to get you to like, solve for things that are not your responsibility to solve.

And I don't do it perfectly. And I like, you know, I screw this stuff up all the time in my own relationships and occasionally with clients, you know, that stuff, stuff shows up in ways that I didn't expect it to. But I try to really be conscious of that, of like, How can I be with you here as an adult and how can you be with me here as an adult?

And then together we get to like consensually decide, what is the shape of this relationship? What is the nature of this exchange? And I'm not trying to get you to be my parent, and I am also not trying to be your parent, right? Like I'm not trying to meet those needs for each other unless that's part of the dynamic that we've both like opted into with a lot of care and caution.

Megan: Thank you so much for sharing that. Yeah. I think it's so true. I am writing about this right now - that how much of this comes back to like our original relationships and what we learned about how to be seen and be cared for, and like you said, there's no quick route to doing that, it's lifelong work, but you really can feel the difference when someone you're in front of has done that and someone who just isn't there yet or isn't willing to do that. And how much more beautiful, you know, to be in commerce with each other in those sort of clean, less convoluted ways. Yeah, I mean, it makes me think about like how capitalism can only survive really, because we're just a culture full of attachment wounds. I mean, it can only exist in that way. Okay, so knowing that this is lifelong stuff and that we're all learning how to relate to each other as adults, and knowing that that can be an ongoing, imperfect process, where might you recommend someone begin if they do have some of these needs, like they need more income or they want to do work that's more meaningful and they want to start a business that is not rooted in toxicity. What are some of the entry points? Cuz it can feel very overwhelming, like, "you need a business plan, you need to do like marketing research on blah, blah, blah, blah, blah."

Where would you recommend people start?

Bear: So, I guess I'll say that my advice is limited mostly to people who are doing like a solo person business. I've worked with people who are like five people and fewer businesses, but if you're trying to start something that requires a lot more labor than that, your first steps will probably be very different than what I'm about to share.

But I think for people who are trying to sell a good or a service that is like, Small scale, the first place I would say to start is to figure out what it is that you wanna sell, and then figure out how much money you need to make, and then you figure out how does the math compute for those things, right?

So if you need to make X number of dollars per month, say how many of the item, whether it's a, you know, a tangible object or a service, like how many of those do you need to sell per month in order to make that amount of money? And at what rate, right? So you can finagle the math, you can triangulate the math in whatever way you want there.

Before you do anything else, you should stop and think, is this doable for me? Right? Like, is it actually plausible for me to work with, you know, 30 clients a week for 52 weeks a year? Because like maybe the answer is no. And so it's like, okay, maybe the rate needs to go up, or maybe I need to sell something in a different configuration that like, allows me to work with more people at a time or whatever.

So really, Kind of doing the, the very low key, very simple income projections of just like, how much money do you need? How many of this thing would you have to sell in order to make that? Is that doable for you based on the time and the energy that you have based on your real capacity? So then you're sort of setting your rates based on that.

The next thing I think you should do before you set up an Instagram, before you build a website, before you do you know anything else... you don't need a logo. You don't need brand colors yet. Like maybe eventually those are like fun bells and whistles to add. But the next thing you do is to just write three to five very clear sentences about what it is that you're selling.

That's it. Just write three to five really clear sentences about what it is that you're selling. Who's it for? What's it solve? You know, what's it good for? Why do you have the expertise to do the thing that you're trying to say that you do? And then make a list of all the people that you know who might be interested to hear about this thing that you have to sell, and then start telling people about what it is that you have to sell.

You can send emails, you can make phone calls, you can send text messages, but start with people who you already know and just start by telling five people, Hey, I have this new thing that I'm selling. Hey, I have this new thing I'm offering and I thought you might be interested to hear about it. I'll say that like in terms of consent, I think it is a-okay,to send people that you actually know one email that tells them about what it is, one unsolicited email that tells them about what it is that you're selling.

So in that email, you should include a way for them to signal that they wanna stay in touch with you about it. So, Reply here if you wanna hear more about this in the future, click this link if you wanna put your name on this email address, on this spreadsheet that I made for me to email you at some point in the future when I start sending an email newsletter, right?

So you don't need to like have all those pieces figured out yet, but you need to have a way for people to be able to signal that they're interested in continuing to hear about the work as it develops or about the product as it develops. And that's kinda it. That is like a good way to start a side hustle. Figure out the math. Does the math make sense with your, like your money needs and your capacity, the market rate, et cetera, et cetera, for whatever it is you're selling? And then, yeah, can you get really clear about what it is that you're selling, who it's for, what you're solving, and then who do you know that you can tell about it?

And that's how, I mean, that's how I got all my first clients. That's how I found all my first students. Just sending emails to people. It's really vulnerable. It doesn't feel awesome to do. But yeah, I don't, you know, I think there's a lot of kind of like, I have a lot of cringe about the kind of like mlm, multi-level marketing, sales tactics that are like people you haven't spoken to in 25 years being like, Hey girl, like what's up? Like can I tell you about these essential oils or whatever? No shade on essential oils, but like shade on multi-level marketing. Uh, and so, you know, I think that the kind of like repeated non-consensual sales is like thumbs down.

I don't like to do that. But like a single update about your life to people who you actually are in relationship with is like totally okay. So, That's my like crash course on how to start a side hustle in, you know, a week if you're trying to do that. What to do first.

Megan: Yeah. Great. Keep it simple. It doesn't have to be complicated.

I love that. It's a good reminder for me too, being further in that it can be that simple to just pivot or try a new thing and just being really sweet to yourself and trusting that the people for whom it resonates will come along and it's okay if others don't. And yeah, just holding all of that at once is really refreshing.

Bear: And again, being really clear about like, yeah, probably all of us have had experiences of like, Wanting to be seen and failing to be seen, being ignored, being misunderstood, being rejected for the things that we've shown to be true of ourselves.

And so of course it is with trepidation that we would approach something like this. Of course there is some like, you know, fear that comes up that says like, oh my God, I couldn't possibly ever do that. But for me, again, the real kind of like taking radical responsibility, not for the things that happened to me, but taking radical responsibility for like myself as an adult now, like it's not my fault that those, that I have these wounds around visibility.

Like, it's not my fault that I didn't get seen. It's not my fault that I didn't get understood, and also, I'm not a little kid anymore. I'm a grownup. I have people around me who love and support me. I can make different choices now instead of be able to like step into that place of empowerment that says, this is scary.

I can tend to that fear and I can do it anyway, like this might feel terrifying and I don't have to ignore that or white knuckle through it. Like I can, I can tend to that. I can be with it. I can grieve the, the origin of that fear and also then that makes space for me to show up and, and say "hey, this was scary, but I did it anyway." I really didn't wanna click send on this email, but I pressed it. You know, I pressed publish on that blog post or whatever the thing, you know, that social media reel or whatever the thing is that makes us feel so freaked out about being seen. We can hold both, you know, we can hold it. We can hold the complexity of that.

Megan: Oh, this has been so nice. Is there anything else, I guess, you would like to leave people with if they are curious about starting a business or reinvigorating one that maybe has been on the shelf or that they've been in? Any other tidbits you wanna leave us with?

Bear: I guess one thing that really excites me is just that like inside our businesses, I think that we have a lot more space to be even more radical than we already are. And so I just wanna give you permission to like really look at the places where there's friction if you already are in business, to really look at the places where there is friction inside your business and see if it's because you are doing things in a way that is like in alignment with how you think you have to do things.

And ask yourself if that's really true. I mean, yeah, I could give so many examples of how that, that question has really changed the way that I do things. You know, where it's like, oh, I think I have to have a cancellation policy that says if somebody late cancels on their session, that they then have to pay me for the session, even though they didn't come.

And I'm like, oh, I got taught that that's the way that I have to do things. Because inside capitalism, I need to protect myself from the customer who's trying to screw me over or take advantage of me. Is that actually true? Is that actually how I wanna be? Is it possible for me to like do things in a different way?

Turns out it is. And so, you know, that's just like one small example. So like now I don't have a cancellation policy. If you get sick or you're, you feel bad, or you need to like go cry outside or whatever, instead of come to our call, it's fine. You don't owe me for that session. The coolest thing is that people don't try to screw me over.

It makes me so excited because people are just like, wow, thanks so much for like offering that to me. And then people generally try to show up when they can, and if they can't, if they genuinely can't, it doesn't feel like I'm getting screwed over, right? It doesn't feel like they're like doing something to me.

Anyway, all of that is to say, Look at your business, look at the friction points, the places where it feels like, oh, this doesn't feel quite right. And like, ask yourself if you're operating in an old set of beliefs, ask yourself if that's like the most liberated way that you could do that thing. And then see what ways you can imagine of like doing things more generatively, more generously, more relationally, like more towards the future world that we can start living in right now if we want to. Sometimes. In some ways.

Megan: Oh yeah. I really appreciate that. I think that's such a helpful orientation, when there's a rub, to sort of try to imagine or conjure your imagination into something else. Yeah. Thank you. I love that. Okay, well, I wanna give you a chance to share where people can follow along.

I also wanna highlight the fact that you're gonna be running another cohort of Marketing for Weirdos, which I wanna gush about because I took one a couple months ago and it was so helpful. Again, like I've been doing this for a little while on my own, and I think it's helpful no matter where you are, either at the beginning of business or further in just a, a really different framework about what marketing is, why we use it, how to do it, so, Can you let people know when that will be coming?

And I wanna just highly recommend everything you do, but especially marketing for weirdos. If people are interested in starting a business, I think it would give some real, like concrete, but liberating ways to be in that. So where can people follow along? And anything you wanna share about Marketing for Weirdos specifically?

Bear: I'll start with Marketing for Weirdos cuz we're here. Thank you so much for those kind words about it. That really means a lot to me. I love teaching that class. It like surprises me how much I love teaching about marketing, but it just feels so generative and life giving to like help more weirdos and artists and activists and people who really want the world to be better to like figure out how to actually talk about themselves and their work in ways that feel good to them and good to the people on the other side. Like that brings me so much joy. So the next round of it, it's a four week online course, and the next round of it, I think is gonna start in August, maybe September, but I think August is what I'm aiming for and people can find out all the information about that class on my website, bearcoaches.com.

If you click the courses button, it'll show up there. Marketing for Weirdos is there. And yeah, bearcoaches.com is where people can find information about hiring me for business consulting. I still do very occasionally take on a life coaching client. So if you heard this and you're like, oh, I don't have a business, but I'd like to talk to you, you can, um, you can find that information on the website too.

And I'm on Instagram. It's really the only social platform that I'm on with any regularity. I'm there very intermittently, but I love to connect with people there, so feel free to reach out.

And there's a ton, a ton of like old content, so if you wanna hear me talk about these things for, for a lot longer, there's lots of videos and, and blog posts and stuff that you can, you can dig into.

Megan: Thank you so much, Bear. This has been just enlivening for me, and I know it will be helpful to a lot of people listening who want to shift and not feel so trapped inside of traditional ways of working. So thank you so much.

Bear: Yeah, thanks so much for having me. Thanks for listening.

Megan: Okay, my friend. I hope you loved this episode, and I encourage you to connect with Bear if you've got a nascent business idea or have, like me, been in business for a while, but might need some fresh energy that feels more human and less like capitalism.

All the links you need to connect with Bear are in the show notes. Again, I'm hosting this Summer Solstice retreat on June 21st. The link for that is also in the show notes. I'd love to have you there if it resonates. I will be back with you next week for a solo episode. Take such good care and I'll see you on the other side.

Resources Mentioned:

To connect with Bear: Follow on Instagram @bearhebert_. More at www.bearcoaches.com and www.undoingpatriarchy.com

To learn more about my Summer Solstice Retreat: https://awildnewwork.com/summer-retreat