Brooke Monaghan, Air Date

[00:00:55] Sanjay Parekh: Today, our guest, Brooke Monaghan, is joining us from Long Beach, California. Brooke is a project management professional who specializes in process improvement, project management, people management, business acumen and coaching. Brooke balances her uncanny knack for simplifying complex problems with her knowledge of industry best practices, and a truly supportive relationship with everyone she works with. Brooke, welcome to the show.

[00:01:20] Brooke Monaghan: Thank you so much for having me. I'm really excited.

[00:01:23] Sanjay Parekh: So am I. And before we get into the fun, juicy parts of it, I'd love for you to give us just a minute or two about your background and what got you to the point that you're at right now.

[00:01:32] Brooke Monaghan: Sure. So, I had shared with you before when we were chatting, that I always wanted to work for myself and just from a very young age was not, I wasn't like that entrepreneurial kind of kid who was constantly doing the lemonade stands and selling things at school. I was just constantly in my mind about, how can I figure out how to not have to deal with, honestly, I think it was like not having to deal with the kinds of things that I was dealing with at school, where I was just like, I don't want someone to be able to tell me what to do for the rest of my life. Like I need to figure out a way out of this.

And then as I got older, I kind of realized that I really loved business. I loved the puzzle of business and figuring out ways to just problem solve around it and the ways that you could generate solutions for people and how cool that could be. And I went to school for entrepreneurial management. Thinking, if I get the know-how for how to do it, then I'll just know what I need to do and then I'll just start a business. And that was absolutely not what happened because I did not realize that knowing what to do and having the risk tolerance and being able to deal with the vulnerability of putting something out there that you really care about or possibly failing and all of that was like, that is so much more part of the equation.

And so, I ended up working retail for quite a while and I learned so much in retail. You just end up as a GM, it's like you're learning so many things that go into running a business, but the thing that was really mind blowing for me was seeing that every single store would get the same setup in terms of, this is what you're supposed to do and this is the product that you have and this is how you're supposed to set it up. And you would see some stores just run like a well-oiled machine and other stores were just a hot mess and were not doing well. And I thought it was so fun to just figure out how to just be really high-performing and also have a team of people that actually were respectful and felt respected at work and had this really nice experience of, I've been working retail for so long and now I actually like working here.

And I worked there for a long time and then finally one day was just like, I can't. I need to do something that, at the very least, feels meaningful to me and is aligned with my values and maybe gives me some space. Because I was so burnt out and I just needed some space to figure out what my business was going to be. I knew that I needed to work for myself, but I never could figure out what my thing was. And I don't know why consulting just literally never popped into my mind. I remember listening to a podcast one day. Podcasts have changed my life, like conversations that I've heard people have like this have absolutely changed my life. And I heard somebody talking on a podcast one day talking about how they started their consulting business, and I was like, oh, wait a second. I know so many people who want to start businesses or who have wound up accidentally working for themselves and don't want to deal with the business side. That's all I want to deal with. Like, why don't I start doing that?

And so, I started toying with that idea while I went into a new nonprofit role. And then what ended up happening was eventually, I ended up in a situation where I was moving across the country for reasons that were just, my husband was getting a job across the country and so I was leaving, and I ended up convincing my employer to hire me as a consultant. And that was my very first client. And I was like, you know what? There's never a good time to do this. I'm just going to figure it out.

And I started consulting with them on the side. I was walking dogs half days and then working on my business half days. And then I started a podcast at the same time where I was documenting, what's the process actually like when you're in it? Because I had heard all these stories about, this is what happened, and it's such a curated story where you have no choice, right? Even in this like it's 30 minutes, right? I'm going to edit out so many things that happened, but I really wished that there was somebody talking about it while they were in it so that I could hear, how do you deal with the stuff that's going on in your head and the really hard things that seemed to be really simplified in these conversations. So, started doing that and that was what actually ended up leading me to doing business coaching because people started listening to my podcast and were then coming and finding me and being like, I want you to help me. I've heard, I've seen all these other business coaches, but I want you because you're just so honest about all of these things and it seems like you're doing it in a way that really works for you and your lifestyle and with your values. I resisted it for a long time, and now here we are.

[00:06:12] Sanjay Parekh: Yeah. Okay. So, there was a lot of great stuff in there that I want to unpack. First, you talked about how you went and got entrepreneurial management — was that the degree that you got? And what I find, I think you hit something that's so interesting that. We don't teach risk management or understanding the risk in those classes. And I don't think we do that in any business class. We talk about risk and risk management, but it's not ever about that personal risk that you take. And I don't know that you can even teach that. It's something that you have to experience. So, for you, how did you get over that hump of dealing with the risk of being an entrepreneur for the first time?

[00:06:56] Brooke Monaghan: I really think it was just as simple as getting so fed up with my own stuff around, why there was never a good reason to do it. And I'll wait until this, and I'll wait until this, and I'll wait until then. And then finally realizing there's always going to be a reason not to, and I literally have two choices. I can either try it and find out, or I can guarantee it doesn't happen by just not trying. The only guarantee that it's not going to work is if you just don't try. And so, I think I just got to a point where I was just like, you know what? This is not going away anytime soon. I've wanted to work for myself since I was like 14. This is not a phase, so at what point are we just going to figure it out? And I think that it was just like, I knew there was a risk, but I also knew that, if I just figured out a way so that I could keep going, I would figure it out eventually.

I was so confident. It might take me longer than I want it to. It might be hard, but working a job I don't like is hard and I signed up to do, otherwise I'm signing up to do that for the rest of my life. So, what are we doing? And I think that was really it. And since then, I've definitely learned, I think you're right, we don't teach the personal risk side, but I do think that something that we could do a lot better at is normalizing the experience of learning something new and how you have to put yourself out there and try some, when you're learning something new, you have to put yourself out there and risk not doing well at it. And in fact, like if you don't put yourself out there and expose yourself to things that you don't know how to do, you're never going to grow at anything. And I think our culture is just so perfectionist. It really does not lend itself well to that.

[00:08:42] Sanjay Parekh: And I think that starts early on, right? When you're going to school and the point is to get good grades and get A's, and if you fail, that's a bad thing. And so, we're kind of indoctrinating that. And to your point, when you learn new things or try new things, you're not going to succeed the first time out of the gate, very likely. It is very rare. Some people will. Some people that are not me, or maybe not you, will succeed right out of the gate, but most of us are going to fail right out of the gate. And we've been taught that's not good, right? And so, it prevents, I think a lot of people and I think to your point, there's a lot of people that prevent themselves from being entrepreneurs because they're afraid of failing because of that. So, you mentioned you didn't do the entrepreneurial thing, selling candy bars to other kids and things like that. Is this your first entrepreneurial thing, and if so, are there other entrepreneurs in the family that you got to watch through this process that has helped you along the way?

[00:09:43] Brooke Monaghan: Yeah. This is my first entrepreneurial thing. But yeah, there's entrepreneurs in my family, but I don't think I realized that until I was older because nobody looked at themselves as a quote unquote entrepreneur. I come from a fishing family, like my dad and my whole dad's side of the family are all commercial lobstermen. And so, they're self-employed, work for themselves. But it's the kind of work where you get up at 4:30 in the morning and you go out and you do physical labor and you get skin cancer because you're like out in the middle of the ocean with the sun beating on you your whole life. And everyone is beat up and it's just such hard work. And I think that honestly that was part of the reason why I really wanted to figure out a way to work for myself was because I really didn't want to have to beat myself up in the way that I saw so many people in my family do it. And I don't think I realized that, well, they're working for themselves.

But I also had other people in my family, my grandmother, actually. She was divorced in the sixties when it was very unusual. And ended up teaching art classes to kids in the neighborhood and then eventually started doing like parties for kids, before that was a thing. And bringing balloons and music. and she made costumes, like character costumes she would go to parties in. That was what my grandmother did. I have an uncle who, my whole life, he's always been in different entrepreneurial ventures, and I actually realized like later on, he had a very kind of a similar path to me. So, there's a lot of it in my family and. I think that the narrative of entrepreneurship made me feel like there wasn't, I always felt like I didn't belong in the entrepreneurial kind of world because there's like this narrative of what it's supposed to look like. And more and more I just realized, it's a mess. It is a mess most of the time and what I was seeing when I was growing up was it.

[00:11:57] Sanjay Parekh: Yeah. There's all different shades of entrepreneurs. And I think the thing you touch on there is that in media, we almost always talk about only one type of entrepreneur, right? The one that raises money and exits for a bazillion dollars or whatever, right? But there's so many shades of entrepreneurship along the spectrum that it can be almost anything from the kid selling candy bars to his classmates to that thing, to being the billionaire because you exited. And it's all valid and it all works. It's just what floats your boat. Not to use a boating analogy for you, because I don't want to set off your PTSD or anything like that.

[00:12:41] Brooke Monaghan: I actually do have PTSD. So, it's actually funny that you say that.

[00:12:46] Sanjay Parekh: I know never to ask you to come out on a boat, especially at 4:30 in the morning.

[00:12:50] Brooke Monaghan: It's not about, it's not around that. It's okay. I get seasick, but the PTSD won't be an issue.

[00:12:54] Sanjay Parekh: Oh, you and me both. I don't think we're, either one of us then are going to be on a boat. I get seasick as well.

[00:13:01] Adam Walker: Support for this podcast comes from Hiscox, committed to helping small businesses protect their dreams since 1901. Quotes and information on customized insurance for specific risks are available at Hiscox.com. Hiscox, the business insurance experts.

[00:13:22] Sanjay Parekh: Okay. So, let's talk about when you started the business. You said like all these things, and you realized like all these things were holding you back for no reason. Was there anything else that made you nervous about starting this, that you were worried about, that maybe this won't work? Was there anything like that and how did you get over that?

[00:13:40] Brooke Monaghan: Everything. Yeah, everything. I was terrified all the time. I remember driving around, I remember driving, like vividly, I have this memory of driving my car and being like, I have felt like I was going to throw up for I think the past six solid weeks. There hasn't been a time where I haven't felt like I'm going to throw up. Everything terrified me. I was terrified that I was going to find out I didn't have what it took. I was terrified I was going to find out that this dream that I had wasn't going to work for me. I was always terrified. I would get a new client and I would be so excited for a minute and then five minutes later I was like, all the other ones are going to leave, or I'm never going to be able to get another one again, or I'm going to blow it. I'm not going to be able to deliver. Everything scared me.

And I think that the biggest thing was, I learned really early on in the process that there was no way to avoid being scared. There was just no way. It was so different from things that I had done before, and I was finally putting myself out there with something that really, really mattered to me. And when something really matters to you, it freaks you out when you start to let other people see it or really go for it and expose yourself to finding out how it's going to go. And so, I think I just embraced it, and now I'm at a point where if I don't feel scared, if it's been a few months and I haven't felt like really scared, I'm like, okay, we're avoiding something. Like something is not happening here because I've just learned that if I'm approaching growth edges, I'm going to feel like I'm going to throw up. It's just the way that I'm wired.

[00:15:13] Sanjay Parekh: Yeah, that's an interesting point. And I think a lot of entrepreneurs feel that nervousness or scared. And I find it funny that you're like, oh, I got this new client you celebrate for five minutes and you're like, oh my God, what if I can't do it? What if I don't get any more? And I think that's the highs and lows of entrepreneurship right there. But I think most of us that keep going harness that energy, to keep ourselves going, whereas people that come off the tracks are the ones that it just becomes too much for you. Was that something that was always true for you? Did you always harness that to propel yourself or did you have to learn how to do that?

[00:15:50] Brooke Monaghan: No, I was such a perfectionist. I was such a straight-A kind of person who needed to do everything exactly the right way. I'm dyslexic and I didn't even realize that until so much later, that it wasn't normal. The amount of stress that I would put myself through to be able to still get a 4.0 GPA. The things that I would come up with to get it so that I could actually understand what I was reading, it was extreme. So, the point being that I was terrified of doing any of that, exposing myself to anything that I couldn't do, and I only attempted anything if I was a hundred percent sure that I could be the best at it. I was like, there's no point in doing anything if I can't guarantee that I am going to be the best person at it in the room.

And eventually I realized that all that was doing for me was just keeping me in this big fish in a little pond kind of syndrome, where I was constantly wondering why I was ending up in these places where I guess it felt good that I could really perform, but it's not where I wanted to be. And so, that was really one of the things that pushed me to be like, okay, it's time to start taking some risks. I'm done with this. When I was done, I was done. I was just like; I'm not doing this anymore. And I just really went totally in the other direction and started opening myself up to finally taking the risk. The financial risk is one thing, that wasn't even the scariest part for me. For me, the scariest part was taking the risk of saying, I am going to go and dare to do this thing, and I'm going to let everyone watch me potentially not be able to do it. It was like the first time in my life that I felt like I was really opening myself up to that. It was brand new.

[00:17:35] Sanjay Parekh: And that's a common thing I think a lot of entrepreneurs have to grapple with because, I remember it from when I started my first company that a lot of other people around me that we're probably scared to be entrepreneurs themselves would say things to tear down the one that's stepping out. And it's hard to do that because, what if you do fail and then everybody's looking and pointing at you and, see, you shouldn't have done that. And I don't know how we solve that problem and how we, get people to kind of normalize no, this is an okay thing and it's okay to fail. It again, goes back to that whole thing of no, you don't have to always make straight A's. It's okay to fail.

[00:18:19] Brooke Monaghan: I agree. I think that there's really something to be said for, and this is something I've been thinking about so much lately because I see it happen so much in the coaching space, where there's people who are saying that what they want to do is help people build confidence and go out there and put their thing out there into the world. But then they're so quick to tear down the way that other coaches coach their clients or why somebody else isn't qualified to be advising you or whatever. And I've gotten to a point — that used to make me really mad. And I used to get really, I mean up until very recently, honestly, like I've really had to work through that.

But finally, I've gotten to a point now where I'm like, okay, you know what? That's a projection of the judgements that you're putting on yourself. And I know that because I used to do that to people. I used to do that too, but now that my confidence has grown, I don't feel the need to judge anyone else in the way that they're doing things because I'm just, you know what? I want to build your confidence so that you can also turn around and do that for other people. And yeah, so I think that it's almost like you've got to be willing to just build people up around you. And I think that with that, it comes back to you in time. But it does mean that you've got to deal with people who are just grouches and it's okay.

[00:19:45] Sanjay Parekh: So, let's pivot on that and talk about the business and how you manage it. So, you're dealing with these clients and you're coaching them and everything, and how do you balance the stress of that? And you're taking on like the stress that they're going through as well. And how do you balance that and the demands of the business with personal life and family and all of the other things that are equally if not even more important in life.

[00:20:13] Brooke Monaghan: I think the number one most important thing for me is, first of all, I have strong boundaries around the work that I will do and won't do. There's certain things that I don't want to do and I've made the mistake of doing it before, whether it be working with a client who really wasn't the right client for me, or them saying could you do this for me? Me saying, oh yeah, sure. Because it's easier to just say yes than it is to set the boundary, and now I'm at a point where it's look, I know what I'm good at. And I know what I am worth you investing and working with me for. And I also know what doesn't make sense for me to be doing. And if I start doing it, it's going to burn me out. And so now I'm pretty good about setting boundaries and I think that helps a lot because there's really nothing that I do in my work that I'm like, oh my God, I can't believe I have to do that.

There are some things that of course I don't feel like doing. I of course wake up some days and just don't feel like working, but for the most part I can remind myself of why I'm doing it and it's enough to motivate me. And so, I think that's the biggest thing is, I really like what I do, and I want to do what I do. And so, it doesn't really feel, there's some days where I have to really stop myself from working, because I just want to keep working on it. And I think also just being incredibly intentional about making sure that anything that I'm doing is sustainable long term. Because I made the mistake early on, and I see so many people do this, where you get caught up in this. I call it the freedom mirage, where it's like, if I just hustle hard enough, now I'm going to get to the point where, finally, I will have achieved enough or earned enough, and then everything's going to be easy, and then I can chill out. And it's like, no. All that does is it sets you up in a business that you just want to escape from. You're not going to be able to do that long term, and this is a long game. For most people, you need to set yourself up for the long game. And so, I've been very intentional about that, with anything that I'm doing, I'm always looking at, okay, is this sustainable for me or is this going to burn me out? Because nothing is worth being burned out for, because it's going to set me back in two months.

[00:22:20] Sanjay Parekh: Yeah. I love that. And you're right, almost always, it's a long game. Any entrepreneur that's getting, even if you're looking to exit at some point, I tell entrepreneurs all the time, it's at least an eight-to-ten-year deal that you're signed up for, once you raise money and do these kinds of things. It's not a quick flip. Like these stories that we see in the media of oh, one year in they sold for a billion dollars. That's so rare. It's like a fraction of a fraction of a percent. So, you can't count on you being that incredible and that awesome that's going to happen for you.

[00:22:54] Brooke Monaghan: Yeah, and especially I work mostly with lifestyle business owners. People who are just trying to do work that they think is meaningful, set themselves up for some amount of flexibility or freedom or control over their schedule. So, I'm like, if that's the point, then what are we doing with this, run yourself into the ground, this hustle. It just it doesn't pay off the way that I think we've been sold on. For some people it does, but I think a lot of it is just going to tire you out and then set you up for a situation that's just like your day job, where now you have a different kind of situation that you want to exit, you want to escape from. And now you're in the same position where you have to start over. So, let's just not do that.

[00:23:42] Sanjay Parekh: Yeah. Do you have routines that you stick to on a daily basis to make sure you stay grounded. Like, make sure you sleep at a certain time, exercise, like whatever it is. Is there a routine that you try to stick to?

[00:23:57] Brooke Monaghan: Yeah, I, have routines that I try to stick to, and I'll be very transparent about the fact that it doesn't always happen. So, I know that I need to be exercising every day. It doesn't matter. It could just be a half hour, just get outside and go for a walk. Or go for a bike ride after dinner or something like that. Sometimes I'll do that, but I really like to be in the gym, so I really try to do that every day. And I also, I really try, every single day, this is a practice that has been so helpful to me, to call to mind actual people who I want to work with or help in my own business. And think about what they're going through, what they're experiencing, and like where they're at so that I can remind myself of how I can actually help people.

Because that kind of reconnects me back to the reason why I'm doing this, rather than feeling like I just have to go through my to-do list and go through the motions. And it makes a huge difference to prioritizing. Like, what's actually important today? And what do I, what kind of marketing do I really need to put out there today and what am I doing just because I feel like I should do it? And that really helps prioritize things and then, I really try to cook dinner every night and not just work until late and then, oh, now I'm out of time so, I have to. Cooking is a reason to make myself stop working. Taking my dog out is a reason to make myself stop working. And I really have to make myself do that because I just get in this mode, I'm one of those people who I hyper fixate and I get into this mode where I will just go and time goes out the window and the next thing I know I'm just working, working, working. I try to stick to the routines, but if I'm being very honest and like wasn't planning on talking about this, but we already touched on it. I have complex PTSD, and the way that my nervous system works is like I get in a freeze response very easily and if my routine is messed up for any reason, like someone comes to town and my work schedule gets thrown off, it will take me, I'm not kidding you, like, six weeks to get back to my routine. And it all has to shift back to like trauma resolution work before I can even get back into it. Going to therapy and actually doing the things that my therapist tells me to do, those would be the two most important things.

[00:26:29] Sanjay Parekh: Yeah, it seems kind of pointless to go to therapy and then not do the things that the person tells you, you're like, yeah, that was fun. No. I don't really need to do that.

[00:26:37] Brooke Monaghan: Yeah. It's very easy to go and then be like yeah, I'm going to do that. And then two weeks later they see you and they're like, did you go for a walk? No.

[00:26:45] Sanjay Parekh: I'm doing it this afternoon. Starting now. Okay, so thinking back, you've been doing like your own thing for a while. If you were able to go back in time, is there something that you've realized now that you wish you would've known then, that you would do differently? And why is it that you would do that differently?

[00:27:07] Brooke Monaghan: Yeah. This question's so hard for me. I have such a hard time not getting in the complexity of, everything taught me something. But we all know that. So I'm just going to indulge the question and I will say that I think I would have leaned into getting help or into other people more and realized how much relationships matter. Relationships are the absolute, in my opinion, three and a half years into this now, I think that relationships are your number one most important thing. And I think that when I first started, I really felt like, I'm going to go off and do this thing on my own so I can do everything on my own. You can't. You just absolutely cannot. And it's not even a matter of get an assistant and outsource and delegate. It's not even that. It's like being willing to send an email to somebody and be like, hey, I need help with this thing. I'm trying to promote this thing. Who do you know who could be a fit for this? Putting yourself out there in that way. And then also reaching out to those people and asking how you can help them. Like my network of other business owners at this point and also just clients of mine who I've worked with over the years and really built deep connections with, it's paid off for me in a way that, if I had known, I would've been leaning into so much harder, so much earlier.

[00:28:41] Sanjay Parekh: Yeah. Is there something that you do to make sure that you're maintaining those connections? Is there a tool or anything else like that you use?

[00:28:48] Brooke Monaghan: I have on my calendar, so I use Asana to manage my all of my to-dos and every single week I have two appointments with myself where all I am doing is intentionally networking with people. And so, I have one day a week where I am reaching out to new people and maybe it's somebody whose podcast I heard, or I heard them on a podcast or someone whose content I saw. And I'm just interested in what they're doing and seeing if they maybe want to learn more about it, about each other and what we're doing, and if we can support each other in some way. Or if there's something that I want to learn from them, I will just ask, hey, I see that you're doing this thing. I really want to learn how to do that. Would you be interested in talking about it sometime? People are always open to that.

And then I have another day where I set an hour aside just to intentionally be in conversations with people. But I think that the big thing is, if it's genuine, if you genuinely care about people, it just happens. And so a lot of the relationships that I have, I don't really need to think about how I'm maintaining them because they're real people who I genuinely just really care for at this point. And we're going for the same things. And there's this bond that happens when you are in relationships with folks who are also putting themselves out there in the way that you are. Where it's just a deep kind of connection that you end up building with those people. I have so many friends now who, anytime that something's going on, in the other person's business and we see them promoting something or something like that, we're like texting each other and like, how can I help? That's just a common conversation that I'm in all the time with folks and I'm really grateful for it now. It was so much harder when I thought I needed to do everything alone.

[00:30:43] Sanjay Parekh: Yeah, absolutely. Okay one last question for you. What would you tell someone who's thinking about taking this leap like you did, and start a side hustle or start a small business? What advice would you give them?

[00:30:57] Brooke Monaghan: I think that the biggest thing is that the longer that you wait, literally, it's just going to be the longer that you wait. It's not like it's actually going to set you up to be any more prepared. I think taking small steps now, just identifying what the tiniest first step is that you could take, even if it's just saying it out loud to somebody that you trust that this is something that you want to do, that counts. So, I would say just start taking even tiny baby steps toward it, because if this has been something you want to do for a long time, it's not going to go away and there's never going to be a time that feels convenient. But the other thing that I would say is, what works for one person might not work for you. And so just be really willing to filter anything that you hear from other people through your own kind of filter and figure out what's for you and what's not for you. My advice might be totally different from somebody else's. And while I went out and just had one client and was like, whatever, I'll walk dogs and I'll figure it out. For other people, they need to maintain a day job for a long time because they need the financial security for themselves to just feel grounded enough to continue to show up. So, you've got to be willing to just do it your own way and don't let what anyone else is doing. Don't compare yourself to that and judge yourself for it because. It's different for every single person.

[00:32:24] Sanjay Parekh: Yeah. Yeah. I love that. Brooke, where can our listeners find and connect with you?

[00:32:29] Brooke Monaghan: Yeah so, I do have a podcast as well so you can find me there. The title of the podcast is Transcend Your Dichotomy. So, if you're listening to this, go over there. And then you can find me at brooke-monaghan.com and all of the things that I have to offer there. I've got all kinds of free resources, so if you want to dive into anything there, then I'm sure I will throw it right in your face as soon as you land on that page with whatever I have going on.

[00:32:54] Sanjay Parekh: I love it. I love it. Brooke, thanks so much for being on today.

[00:32:58] Brooke Monaghan: This was so fun. Thank you so much.

[00:33:01] Sanjay Parekh: Thank you for listening to this week's episode of the Side Hustle to Small Business Podcast, powered by Hiscox. To learn more about how Hiscox can help protect your small business through intelligent insurance solutions, visit hiscox.com. And if you have a story you want to hear on this podcast, please visit www.hiscox.com/shareyourstory. I'm your host Sanjay Parekh. You can find me on Twitter at @sanjay or on my website at www.sanjayparekh.com.