LOVED this interview with the butt-kicking, career-coaching, ukulele-playing Michelle Ward, as she gives her advice on how to quit your job to start the business of your dreams.

Click here to learn more

Download/listen elsewhere:


Resources from this episode:

Full transcript:

***Note: Normally, we put first names to distinguish between speakers. But since we both are named Michelle W, we’re just going to use Host and Guest instead! 🙂

INTRO: [00:00:00] Hello. And welcome to the Young Scrappy Money podcast. I’m your host, Michelle Waymire. And each week, I’ll be bringing you tips and tricks to help you take control of your finances as well as interviews with people who made big financial changes in their own lives. So join us. And we’ll help you get your financial s**t together. 

HOST: Hello, everybody. Welcome, welcome to another episode of the Young Scrappy Money podcast. I’m feeling pretty accomplished today, you guys. I do wanna let you know that when I was driving to work this morning, I thought very, very hard about stopping at CrackDonald’s. That’s McDonald’s for those of you who don’t have the addiction that I do. 

Um, I didn’t stop at CrackDonald’s this morning on my way to work. And I’m feeling pretty powerful about it. As y’all know, I’ve talked about this previously. One of my goals is to buy a house this fall, so tightening up my budget, fixing up my money mindset, and generally trying to do all the— all the good stuff day in and day out to make things happen. So that’s my little personal victory to share with you before we get started.

It feels like a good day because I get to come to work, and I get to work on my dream business. So for those of you who don’t know, I’m a financial advisor and financial coach in addition to running the Young Scrappy Money podcast. It’s probably pretty obvious. There’s some advertisements in this podcast every single episode. So if you’ve heard it even once, you might know that this is true about me.

But you don’t necessarily realize that this is my dream business. This is my jam stuff right here. This is why I get out of bed in the morning. And I’m really grateful that I get to come to work and do it. It is hard to find your dream business. Or it can feel really hard.

And so I’m excited because with me today is somebody whose number one goal is helping other people find their dream business. So her dream business is helping you find your dream business, which is very, very good. Um, I’m talking about Michelle Ward, PCC. She’s been offering dream business guidance for creative women. And she works under the name the When I Grow Up Coach, which is just fantastic.

Um, she’s been in New York Magazine, The Huffington Post, Etsy, Newsweek, USA Today. She’s one of the Forbes Top 100 Websites for Your Career. This gal, like, knows her s**t. So I’m super pumped to pick her brain and for you, if you’re listening, and you’re having those dreams about quitting your job and sticking it to the man and following your heart, that by the end of this podcast, you have a little bit more clarity on how to make that happen. So welcome, Michelle.

GUEST: Yay. Thank you, Michelle. And thanks for pointing out how meta my business is. I— it never clicked for me until you said it that way. I was like, that is so meta. But it’s exactly right.

HOST: Yes. I should also note that, uh, I actually met Michelle at a conference. It was the Women Work Worth conference— rest in peace. Its one glorious year was extremely good.

GUEST: Yeah.

HOST: And she was one of the keynote speakers. And sometimes you listen to somebody speak, and afterwards you just think, maybe— maybe I can convince this person somehow to be my friend. Like maybe there’s something I can say to persuade them—


HOST: To— to be my friend. And I definitely had those vibes about Michelle Ward. So y’all are in for a treat for reals.

GUEST: Mich— that is so sweet. And I have to tell you, you have a leg up because you’re a fellow Michelle with two Ls. So we’re obviously bonded for life already.

HOST: Yeah, two Ls, two Ls.

GUEST: Two Ls is the way to go. Any of those one-L Micheles, like, you know, it’s hard. They gotta like take a test to be in my circle.

HOST: Yeah.

GUEST: You know what I mean? We’re wary of each other.

HOST: Yeah.

GUEST: Those one-L Micheles and those two-L Michelles. But we’re two-L Michelles, and we’re bonded for life.

HOST: It’s definitely some Jets versus Sharks, you know. When I see a one-L Michele, I snap at her— or them or him. 

GUEST: (SINGS) (SNAPPING) Just keep making those musical theater references. It just goes right to my heart. I love it. 

HOST: Awesome. So I know you’ve been— you’ve been operating as the When I Grow Up Coach since 2008. But that was not always your job.


HOST: So I think to kick things off, why don’t you walk us through a little bit more about your story and your background? Like how did you get here? 

GUEST: Oh my gosh. Yeah. OK, I’ll try to keep it short— no promises.

HOST: No, don’t keep it short.

GUEST: Because it was like a long—

HOST: Tell us everything. Tell us all your secrets.

GUEST: A long, meandering road, right? Yeah. And I work— you know, I work exclusively with creative women. And like no one has a linear path to their dream business EVER, and I am not the exception. So really, like, my tale starts back when I was a wee lass and totally got obsessed with musical theater and performing. 

And that— I was one of those annoying kids. If you asked me when I was 10-year-old— 10 years old, what do I wanna be when I grow up? Um, I would say, you know, a performer or an actress or on Broadway. And that was my like— 

HOST: Me, too.


HOST: Yes.

[00:04:54] GUEST: What? I don’t think I knew that. Um, and so that was my like single focus. Oh my god, I’m doing everything to get up there. I got into NYU’s Tisch School of the Arts for musical theater. I graduated a year early. That’s how excited I was to like go pound the pavement and be an actor. 

And it took me— it took me probably about five years after graduation to really get so downtrodden about the business of show business that I was able to finally look in the mirror and say, I still love performing, but I don’t want this to be my career anymore. And I went through a huge identity crisis at this point as— as anyone could probably imagine. So it was one of those like, OK, not only is this not what I wanna do, but like who am I if I’m not doing this thing? Because this is who I’ve been forever. And I’ve been chasing this dream forever, even though I was only in like my mid to late 20s at that point. 

Um, and so while I was working as an actor but like kind of not really going after it, I did real estate. I got my license. I then didn’t want the commission-only lifestyle. And I started doing sales. That came with a salary. And then I was like, I don’t wanna do sales. 

And then I went to be an account manager for this company that, like, on paper should have been my dream job. Because what was important to me was that I not spend the next, you know, 40 years of my life at that point until I was able to retire, um, on— in a job that I didn’t want to be at. And I wasn’t as optimistic as I am right now. And so I didn’t really feel like I was going to find something I was gonna be as passionate about as I was about performing. 

But I— I just did not subscribe to what we’re all told, especially in America, that like, oh, you’re a grownup. And grownups go to work. And my dad used to say to me, uh, it’s called work because it’s not play. But I guess I have to go back tomorrow so we can eat and like keep this house. Um, I rebelled against all of that. And I was like, I wanna find something that I’m excited about doing at least, or I feel that I’m good at doing, and feeling valued, and feeling fulfilled. 

And I found this job that should’ve been so great on paper. It was for a company that was like not exactly a startup but felt that way, a lot of young people, a cool office in NoHo in New York City. And people would go to work in pajamas. And it was really— my role as an account manager was really about communication and relationship building, which were the two things I knew I was really good at and made me feel valued and fulfilled. 

But I had this verbally abusive manager who made my life hell. So about a year into the job— and at this point, I still wa— still hadn’t reconciled the fact that I was like leaving acting behind. I was still in that place. I was like, yeah, yeah, yeah, I’ll still get Backstage magazine every Thursday and write auditions in my Filofax. Because that’s how long ago this was. But I wouldn’t like actually go do it. 

Um, but after about a year into the job, I was on the subway and going to work. And I had to run out at Union Square, which is one of the busiest subway stations in New York City, during rush hour, a million people, and dry-heave into the trash can. And the job had such a hold on me that I didn’t just immediately say, well, I’m sick, and I better get myself home. 

I said, I need to go to the office, grab my laptop, tell my colleagues that I’m sick, and go work from home. And I did that. I like went up the platform. I went up the stairs. I got to street level. I walked like almost 20 blocks, feeling ill, to my office, got my stuff. 

And the second I left, I felt fine. And I think that was really my breaking point moment and my turning point moment of like, I need to get out of this job. And I really need to figure this out. Because I’m not pursuing acting anymore. And I need to like make it happen. 

Um, and that’s when I found life coaching, of all silly things, and, um, realized that I wouldn’t be happy unless I was gonna be an entrepreneur. And the very first thing I did when I had that realization was to get a new job that wasn’t so emotionally taxing. And I got a job as an executive assistant for a financial consultancy company. 

And the month I got hired was the month I started my coaching certification. Um, and I got certified about two years later. I got mar— I got engaged and married in that time frame. And then two years and seven months after I started that executive assistant job, I was able to give my notice in March of 2010, the middle of the recession, and left to be the When I Grow Up Coach full-time. And knock on some wood, never had to look back. 

HOST: Aw. That’s so very good. Um, did you— so you said you found life coaching, of all things. 

GUEST: Yeah.

HOST: Did you kind of know or have that sense of certainty like, oh, s**t, this is it?

[00:09:54] GUEST: Um, after a while, yeah. So it was definitely— I think my realization— my first realization was, oh, s**t, I wanna be an entrepreneur. And I’m not gonna be happy unless I work for myself. Um, and I wrote a post a few years ago— I could find it for you so you could link to it— called like “21 Jobs in 7 Years.” Like I literally had 21 jobs in seven years. 

And I realized— it was one of those things that’s like, oh, maybe the problem isn’t everyone else. Maybe it’s me. I mean, the problem in that job that I described was definitely like my dick of a manager. Um, he was awful. But it became really apparent that like, oh, yeah, I just don’t fit anywhere. You know, I call it my “oh crapballs moment.” 

And then once I realized, well, I wanna be an entrepreneur, which pissed me off because I really wanted— I wanted the, quote unquote, “grownup job.” Like I wanted the mythical things for me at the time as an actor, which was like benefits and a 401(k) and health insurance and all that stuff that I had never seen a day in my life, working all of my, you know, day jobs and sales jobs. And so I was really upset that I just didn’t wanna like go be an accountant or something like that.

Um, but then once I realized that, then it was, OK, well, what business do I wanna start? And really, I knew right away that I wanted to be in like a, quote unquote, “helping profession.” And I looked into being a social worker. And I looked into being a therapist. And those didn’t appeal to me for a number of reasons. 

And that’s when I found out about life coaching, which I don’t think I’d even ever like heard of up until that point. And, oh, that was the other like “oh crapballs moment” because back in 2007 when I found it, you know, it’s still I feel like life coach— and there’s a reason I don’t lead with like, I’m a life coach, and I use, you know, business coach. Um, there’s that stigma of like, I’m gonna read your aura. And like, let’s come braid my leg hair.

And like they’re— and like grow out your leg hair. Do it, girl. That’s great. I’m now someone that wears crystals in my bra. So I’m definitely more hippie-dippie than I was back then. But back then, I was like, oh my god, this is so not me. It’s not who I want people to think I am. Like this hippie-dippie life, what? 

But I came to realize that it was the way that I most wanted to go do the work that I wanted to do, which I figured was either gonna be relationship coaching or career coaching. Um, so it’s like I— I enrolled in a life coaching course because I knew I wanted to get that certification to then parlay that into the type of coaching that I wanted to do. And it became apparent pretty early on that, for me, the career coaching piece, and essentially being the coach that I needed at the time that I couldn’t find, was what I wanted to do.

HOST: Yeah. That’s great. So a couple of other follow-up questions, more kind of on the— you know, your background and your history, before we get into helping others find their dream business and kind of act out those things.

GUEST: Yeah, yeah.

HOST: Word on the street is that you have a pink ukulele named Lucille. 

GUEST: I do. It’s totally true. 

HOST: What can— what can you tell me about her? What role does music play in your business?

GUEST: Oh my gosh. Oh, it’s funny. And, you know, I don’t play as much as I used to, which makes me sad. And you’re reminding me that I need to pick Lucille back up and give her some love.

But, you know, with my musical theater background, once I— once I left that behind, and I was living in New York City, what was really difficult was that I didn’t— I didn’t really have a place that I could tap into the performer in me. Because everything is so competitive in New York City that even if you’re auditioning for like a community theater production, you could be there with 400 other people. And it’s ridiculous.

HOST: Oh, wow.

GUEST: Oh, yeah. It’s— it’s insane. And so I kind of left that piece behind. And I really wanted to just like sing more. And I wasn’t really letting myself do that so much. And I remember I just kept thinking like, I wanna buy a ukulele. Like I think if I buy a ukulele and teach myself the ukulele, I could kind of just even sing more for myself and have fun with music again. 

And I bought that ukulele in the summer of 2011. And I took some like— you know, watched some YouTube videos and kind of taught myself a few things. And then I went, and I took lessons and learned how to play it. And it’s interesting because it came up like, um— when it comes to my business, like once I started playing, I would bring it to any sort of speaking gig that I had.

Um, I’m big on when I speak, when I used to speak— I don’t necessarily do this every time I speak anymore. But, um, I would have the participants, you know, answering questions while I was up on stage. And so there would be like, you know, three minutes or five minutes where I’m— where they’re writing. And I would bring my ukulele so I could play like background music.

[00:15:10] Um, I would play the ukulele for any webinars that I did. Uh, I would play the ukulele— I had an about video on my home page for a while that also featured the ukulele. So it was fun to be known by that. And it was fun to bring that into my coaching and my speaking gigs and give it a sense of lightness and fun that I think just, you know, set me apart to my right people.

HOST: Yeah. That’s wonderful. I also have to ask— because your bio says this, so it’s not my fault for asking. I have questions. 

GUEST: Uh-huh, uh-huh. 

HOST: Um, your bio alludes to the fact that you were a Judge Judy fan contest winner. And I gotta hear about it.

GUEST: Yeah, yeah.

HOST: I just need to know. I need to know what’s up.

GUEST: Yeah. Well, Lucille played a big part in that. So back in 2014, I’m— I’ve been a Judge Judy watcher for a long time. And, um, she’s someone that I started watching like in the morning before I would— like as I was getting ready to go to work, I would put Judge Judy on because it’s something you don’t really have to watch. You can just kind of listen to as you’re getting ready. 

And she just became a staple in my day. And I just became like a huge, huge fan. Um, so I would record the shows that were on at like 4 o’clock and then watch them in the morning. And for like a few weeks, I would see in the closing credits, enter to win a trip to meet Judge Judy. And I was like, yeah, that sounds like something I wanna do. 

Um, so I went to their Facebook page. And they were running this contest where they were picking three different winners based on the three different ways you could enter. So you had to either write an essay or make a video or draw a picture that alluded to what you’ve learned from Judge Judy, like the lessons that Judge Judy has taught you. And the essay had to be a certain length. And the video couldn’t be more than like 90 seconds or whatever. 

So I looked at that and went, oh, I’m gonna go write a song on my ukulele about Judge Judy. And I’m winning this contest. Like it was one of those things where I just went, yeah, I’m gonna win this contest. Um, so I— I wrote like a, you know, 70-second song about Judge Judy on my ukulele. I put it on YouTube. I entered. 

And, ah, I will not forget this. They wound up a week or so before they announced— they were gonna announce the winner, they put my video on Judge Judy’s Facebook page. And it was like, look at this entry. Blah, blah, blah, it’s so great. And I was so excited because I’m like, I’m gonna win. I’m gonna win.

And they said, winners are gonna be announced April 1, April Fools’ Day. And I was going— and I remember I was going like a few days later to California with my husband to speak at another conference. And on April 1, I heard nothing. And I couldn’t believe that I lost. I was so upset.

And I was like, you know what? It’s April Fools’. They’re probably playing a joke on me, and I’m gonna hear like tomorrow that I won. I would not accept it. And on like April 2 or April 3, I got on a plane to go to California. And when the plane landed, and I turned my phone back on, there was a voicemail from a 310 area code, which is Los Angeles. 

And I look at my husband. And I said, this is Judge Judy telling me I won the contest. And he’s like, Michelle, you lost the contest. Like you just have to deal with it. We’re in California. It might be someone from our hotel that’s calling you. Like we don’t know.

And it was literally the Judge Judy person calling me to tell me that I won the contest. And I like lost my mind on the plane. And I think that whole plane knew that I won the Judge Judy fan contest. And I got— and I like went back to California. They were like, you have to come in this two-day window. Yes or no? And I was like, yeah, of course. 

Um, so I got— I got flown out. And I got to be on the set and see her do cases for half a day. And then they tricked me into like making a YouTube video where then that’s when I met her. Um, so I could link to that, and you’ll see me like be a crazy fangirl but try to keep it together and act cool because I’m being recorded. 

Um, and then we got to go have lunch with the crew. And Judge Judy came to our table at the end and got to talk to us. And it was like all my dreams have come true in my life. Oh, and then— and then like I became a mom the next month. So like it was a good— it was a good chunk of time. 

HOST: Oh. You’re living the dream, my friend.

GUEST: The dream, I was living the dream. My life— I like to say my life is super weird. Like my life is just really weird. Um, so yeah, that was part of it. But, yeah, totally living the dream. And I feel like I manifested it/aggressively got it somehow. Because I was just like, yeah, I’m winning this thing. I’m winning.

HOST: I think all the best life plans are a combination of both, right? You manifest that s**t. But then you also bring your A game a little bit. 

[00:19:55] GUEST: Yes, totally, totally. And Judge Judy did say that like she— supposedly they were late a day or two because Judge Judy herself wanted to pick the winner. So they brought her like, here are our top picks. And she decided. So she said she used to have a babysitter that would come over and play the ukulele, so that was very endearing for her. And I was like (CLAPS), ukulele for the win. Thank you, Lucille. Thank you. 

HOST: Oh. So I feel like now we have a pretty good understanding of how awesome you are as a person. So now people are like pumped and ready to take all of your dream advice, now that they know the feats of which you are capable as a human.

GUEST: Right.

HOST: Um, so let’s get into dream businesses. I know that I personally as a coach work with a lot of people who wanna quit their jobs. And you talked a little bit about your journey. But how— how does one in general start to find a dream business?

GUEST: Yeah. OK. So keep in mind that everything I say really exclusively applies to creative people, usually creative women. Um, I’ve exclusively worked with creative women for probably the last like six or seven years. So someone who wants— I don’t— who doesn’t kind of identify as a creative person might hear me talk and be like, none of this applies to me. And in that case, like a traditional, you know, career counselor or business coach sort of person might be right up your alley and be able to help you. 

But I work with women who are highly creative and multi-passionate, and they’re supersmart. And they’re really ambitious. And I think what is hardest for them is to, A, allow themselves that sliver of belief of like, I could do this and make it work. 

Because they have all of the responsibilities that their families and society have kind of put on them. And they’re people pleasers. And they’re perfectionists. And so they have to first just lead with that sliver of belief of like, I could do it and make it work. 

And then they need to shut down— and I like to tell people like, try to do this for a week. Make it temporary. Like I’m shutting down the nos for one week. And instead of telling myself all the reasons why I can’t do this and all the reasons why all these different ideas won’t work, I’m going to say instead, how? 

I’m gonna say to myself, but if I were to do that, how could it happen? But if that worked for me, what would that look like? But if I got my right plans, then how would that feel? Um, and I think really once you kind of open yourself up to that, it’s a really big like mindset piece. Then at least the ideas start coming. 

And I find that most of the time, what my clients wind up saying like, this is the what of my dream business, or at least this is where I’m gonna start. Because I tell people, we need to put the crystal ball away. And I don’t care if you think you’re gonna do this in 10 years or not or, you know— you just have to— you have to feel connected to it now and feel like it speaks to you, to who you are now and who you wanna be in the near future. 

Um, usually it’s the stuff that has been like sticking for a while. So usually it’s the ideas that they’re like, well, I’ve been wanting to be a stylist for five years. But, oh, it’s not gonna work out because of X, Y, or Z. Or like, oh, well, I’ve always wanted to be a children’s book author. But blah, blah, blah, here’s the reasons why. So usually my clients— and because they’re multi-passionate, they usually don’t have a lack of ideas. 

But if anyone’s listening and feels like, well, I don’t have that thing, I always say to start with whatever you discount for yourself as coming easily to you. Because we also have to reprogram ourselves that we think we have to climb the mountain, and like pay our dues, and climb the ladder. And we have to hustle. And things have to feel really hard. And if it doesn’t feel really hard, then it’s not something worth doing.

Where I find the opposite, that if my clients say like, but anyone can do blah, blah, blah— or, but this comes so easily to me. It doesn’t count. Like that’s what we need to hone in on. Because that’s your zone of genius. And that’s what you’re able to deliver on. And that’s why people would hire you and work with you. 

HOST: Oh, I love that. 

GUEST: There’s a lot right there. Um, and I used to say that— like when I work on the discovery stuff with my clients, I have a program called Discover Your Dream Business, which is an eight-week program. Because it’s just not as easy as like, follow these three tips, and then you’ll do it. Because even if you do find some answer for yourself, it’s very hard to reconcile it. And it’s very hard to commit to it and start working towards it. That’s for sure.

[00:25:11] HOST: Yeah.

MID-ROLL ADVERTISEMENT: If you love the Young Scrappy Money podcast, you’ll love our digital subscription service. For less than the cost of your gym membership, you get access to our whole suite of classes, workbooks, a private Slack channel, and more. Check us out online at www.youngscrappymoney.com

HOST: I wanna get back to something that you mentioned earlier. Because you started your business while working elsewhere. 


HOST: And I like that you had mentioned too that you kind of knew that you wanted to be in a helping profession. And so that was kind of your hook to do the additional research. So, um, I think— that’s I think important to realize. 

And then second, we— a lot of us have this idea that when you decide to start a business, you quit your job, and you dive in. But I like that you mentioned you— your goal wasn’t to quit your job and dive in. It was to find a job that was less emotionally taxing to get you the runway you needed to start things up.

GUEST: Yes, yes. I like to say— and this is some of the first work my clients do when they— when they get that dream business piece is like, oh, I need a bridge job. I like to call it a bridge job because it’s gonna be the quickest way to get you from where you are now to working in your business full-time. Um, and it’s about, you know, what job is gonna give you the money that you need to like calm down about money and not stress out, while giving you the most time and energy that it could give you that you could devote to your business and side hustle it up? 

So I— you know, if I was in the position where I had a trust fund or a rich partner who wanted to pay all my bills or whatever, then I might’ve been like, oh, here’s life coaching. OK, bye. Like I’m just gonna go do this thing. But I was not in that position. Um, I lived in New York City. 

I— at the— in 2007, I had moved in with my boyfriend at the time, who’s now my husband. But like we shared the bills. We fully shared the bills. And if I just quit my job and was like, yeah, I’m just gonna make this life coaching thing work and make enough money to pay my bills, I knew that was the quickest way to fall flat on my face. 

So that’s— it’s solidly half the reason why I named my business the When I Grow Up Coach. Because it’s not only about, “What do you wanna do when you grow up?”— quote, unquote. But it’s about, I’m a grownup. I have grownup needs and responsibilities and priorities and values. 

And amen and hallelujah to the people, you know, trust fund or rich partner or just like, I’m in a place where like, I don’t care. Let’s move in with seven roommates and eat ramen noodles. Like amen and hallelujah to those people too. Um, it just was not me. And it’s not the majority of my clients. 

So I had to figure out, what is that job that’s gonna allow me to make the money that I need? And like I was looking for, let’s punch in at 9:00 AM and punch out at 6:00 PM, which was the best that I could expect, right? And I got a lunch hour that I had to take. Because, for the job that I got, you got paid for overtime, which was awesome because they didn’t want you to take it. So it was great. 

And, you know, I got a $10,000 raise essentially when I started that new job. I was gonna get a bonus every year, depending on how the company did. I was getting the mythical things that I wanted. And I was just able to breathe and be like, OK, I can take my time, even though I’m very impatient, native New Yorker. 

It was like, OK, I don’t have to— I could— I could get my certification. I could build my business. And then I could leave on my terms. And when I was in those two years and seven months, they definitely felt hard and annoying, to put it mildly. 

But now that I look back, you know, nine and a half years later, um, I’m able to go, oh my gosh, that’s all I needed to do to be here with you, talking to you? And helping, you know, thousands of women along the way? And making more money than I could ever dream of, and now being the breadwinner of my family, and a homeowner, and, you know, sending my daughter to the preschool that we want, and blah, blah, blah? Like I cannot— like worth it, all worth it, exactly right. 

HOST: Yeah. I love the term bridge job. Because I feel like a lot of folks have this concern that if they go and find another job, or the in-between job so to speak, then it’s not gonna actually be an in-between job. That people will feel so comfortable there that they’ll be scared to leave, and have the golden handcuffs, and not really be able to make the leap— rather than seeing it as a bridge and a journey to where you wanna be. I love that.

[00:30:03] GUEST: Yes, yes. But, you know, and the asterisk there is that you have to be either a self-motivated person to know that, I’m getting this bridge job, and then it’s on me to keep moving my business forward, and/or you better enlist the help that’s going to keep you accountable and is going to make the next steps for you very clear and actionable in order for you to get there. Um, because it is really hard to get out of those golden handcuffs. It is really hard for a lot of people to hold themselves accountable. 

There were definitely so many things that I had to say no to when I was in that job and building my business that cost me friendships and, you know, all of that stuff. But, um, again, like worth it, worth it, but very hard in the moment. 

HOST: Yeah. So I like that you mentioned self-motivation. 

GUEST: Yeah.

HOST: Because I think we can both agree that starting a business is hard. It’s— 


HOST: It can be a difficult exercise.

GUEST: Yeah.

HOST: So what types of other emotional pitfalls should people be prepared for as they’re going through this process? 

GUEST: Oh my gosh. Um, you know, I call the voices in our heads that suck the good stuff out of us our vampire voices. And you’ll appreciate this, Michelle, because you’re a musical theater nerd like me. I got it from “Die Vampire, Die!,” a song from a show called [title of show], which is one of the most amazing shows ever. Um, and, you know, the vampire voices are so loud when you get closer to what you’re going after and what you’re supposed to be doing. 

So I think— and again, I’m speaking directly to like my experience and the experience of my clients. But there’s the perfectionist piece that we hit up against. There’s a procrastination piece that we hit up against. There’s the, um, ah, you can’t do this. Who are you? You think you’re special. Like why are you— especially if you’re in a good, stable job, right? 

I left my job in the middle of the recession to be the When I Grow Up Coach, of all stupid things. And— and it was definitely like there were outside voices and inside voices that are like, are you an idiot? What are you doing? 

Um, I had a client just email me the other day. And she’s, um— she’s close to— she’s been working on her business now for probably about a year. But she’s kept the website down because she’s worried about what work is gonna think. But she needs to put it up in the next few months. And so she’s starting to talk to people about it. 

And she said, you know, she went to dinner with someone she really respects and admires. And he was like, why are you doing this? Like why are you potentially jeopardizing this stable job, and blah—? And it sent her into this huge tailspin. 

But what I like to say is to keep in mind what Steven Pressfield talks about in The War of Art, which is an amazing read and one I highly recommend to everyone. It’s a quick read too. Um, and he talks about it in relation to finishing your creative work. But I think it applies to being a business owner too. And he says, your only job is to show up and do the work. 

And he then doesn’t care how good the work is, what ultimately happens to the work. He said, you could show up— and he’s kind of extreme. I don’t have to be as extreme as him. He goes like to his cabin in the woods without electricity or Wi-Fi and like types for six hours a day and then leaves and goes home— or eight hours a day or whatever and leaves and goes home. But he says if he takes everything he wrote in a year and puts it in the trash can, and it’s gone, it doesn’t matter. Because his only job is to show up and do the work. 

And so that’s what I tell my clients. Your only job is to keep showing up and doing the work. And I think a lot of times people feel that they need to trust this business right off— out of the gate. I had a client say the other day, Michelle, I don’t feel like I can make money at this. 

And I was like, yeah, why should you feel like you can make money at this? You haven’t launched your business yet. You don’t have a client. Like why would your brain think, oh, yeah, I got— I’d be almost more concerned if she was like, yeah, I feel totally 100% confident and feel that I can trust this. 

It’s like so we expect all these things. And it’s like, no, that’s not the reality. You have to allow yourself to be a beginner. You have to give yourself that grace. The only way to get that trust and confidence is time and experience. 

[00:34:44] And I think a lot of the times, because our wins at the beginning are like a long time coming and kind of nebulous and take a while, whatever you can do to track what you’re doing so you can look back on your progress and say, OK, oh, look, I see how I did X, Y, and Z. 

Even though there’s not a client yet, or even though there’s not money in the bank yet, or even though I can’t quit my job yet, I see the progress that I’ve been making. And that’ll hopefully motivate you to kind of go forward. 

So there’s a lot of an emotional stuff that goes in there. But hopefully, if you approach it the hippie-dippie life coaching way, you could see it as like, this is an experiment. This is like a— I had a client say that all of this was like the biggest self-development and self-knowledge tool that she’s ever had. And she was like a self-help junkie. 

That discovering and launching and working in a business is just, woo, you’re gonna get to know yourself, and what you’re capable of, and your fears, and your dreams, and all— and like get ready. Lean on in. Lean on in. 

HOST: Yeah. As a recovering perfectionist/not super recovered yet, I definitely appreciate this— this feedback. So thanks for specifically targeting me there just now. It’s no big deal. 

GUEST: Of course. 

HOST: I love it. Um, if I had a cabin in the woods where I could type six hours, that would be amazing.

GUEST: It would be amazing, but also maybe a little bit maddening. Like this was like— he was like, you need to go every day to your cabin in the woods that doesn’t have electricity and has an outhouse and just like type until your fingers bleed. And I feel like sometimes, ugh, this hustle mentality makes me crazy, especially in the, quote unquote, “girlboss” universe, which makes me, (RETCHING) excuse me, I’m gonna throw up. 

HOST: Yeah. I wondered when we were gonna hit that GB.

GUEST: Ugh, ugh. It came up.

HOST: Because we curse a lot on this podcast. But, uh— 

GUEST: I can’t. I can’t. The girlboss stuff I cannot get behind. Like my business coach is like, are you using the girlboss hashtag on Instagram? It’ll probably get you new followers. 

I was like, I don’t care. I cannot do it. I— like that is not— that is so condescending and obnoxious. Like I’m not a girlboss. I’m a CEO— the end. Like— 

HOST: I’m a founder. 

GUEST: I’m a founder. I’m a CEO. Like and that’s what I help other women do. Um, but I think there is this mentality of like, you have to be working around the clock. And you have to hustle. And you better blah, blah, blah. And like, nope, nope. 

Um, you know, and I don’t wanna say that my timeline is anyone else’s timeline. I’ve had clients leave their jobs and launch their businesses within months or weeks of working together. And I have had people where they send me an email five years after we worked together. You know, I just left my job. 

Um, but you will help nobody if you are burning the candle at both ends, if you are not sleeping, if you are working like you are your own clone. Like it is not going to be helpful and productive. Stop it. Don’t do— if your family forgets what your face looks like, this is not the life we wanna live. No, thank you. No, thank you. No, thank you. 

HOST: Yeah. That’s a good point. And to be fair, I don’t have a cabin in the woods. But I do have a very good French press and a fridge full of LaCroix and a laptop. 

GUEST: Ooh. Yay.

HOST: And I feel like maybe that’s my cabin. 

GUEST: Yay. That’s perfect and exactly right— exactly right.

HOST: So speaking of laptops and fridges full of LaCroix, um, I want to talk about support structures. 

GUEST: Yeah.

HOST: Because I think it might be useful for folks to have a good sense of some of the things they might consider accomplishing or getting on lock while they’re in that bridge job or while they’re preparing to quit their main job. 

GUEST: Yeah, yeah. 

HOST: So what good support structures do you recommend or did you put in place before you could start? 

GUEST: Mm-hmm. OK. Here’s— my answer to this question has varied greatly since I started talking about this like a long time ago. Um, I used to say, here are the things that you could consider doing, blah. Like figure out what’s important to you. And now I say like, here are the things that matter. Because they apply to all my clients. 

Number one is a savings goal. Um, I call it your breathe easy number. Because when you look at it in the bank, you go, (EXHALING) ahhh. And this number also varies greatly for people. 

Some people, this number is like, I just need $2,000. And I know that that’ll float me for however long. And like I’m someone who, once the pedal’s to the metal, like I will go in motion. And like that’s fine for me. 

And I’ve had other clients be like, it needs to be $10,000. Um, for me personally— and I wish that I had myself when I was going through this. Because all of this is in hindsight, not while I was working in this way. But for me, I saved up all my coaching money. Any dollar that I got from coaching I put in a separate savings account. 

[00:39:58] And I had very little overhead when I started, minus my certification program. Um, and so once I saw that I had about four months’ severance in that account, it was December of 2009. And I knew I was getting a bonus in March of 2010. And I said, when I get that bonus, if I put the bonus in the savings account, in this particular savings account, then I’m essentially leaving with five months’ severance. 

And if I’m smart about that money, I can make it last for like eight months of bills. I went, OK, that’s good enough. Like I’m giving myself that runway, and I don’t have to— and believe me, I had like plan B. What’s plan B? What’s plan C? What’s plan Z in case the money runs out or anything like that, and I needed to go find something else without just getting into another full-time executive assistant job? 

Um, and so for me, that was the number. So I always tell my clients like, figure out— I like to see it either in terms of the expenses that you have and like how many months’ worth of expenses, or you know what you get paid right now. And you know how far that lasts in terms of the bills you have to pay. How much of that do you want? 

And then I ask my clients— because usually they pick a number that doesn’t need to be as high as it is. And then I say, what if that number was a little less? Like is there really a difference between 8,000 and 10,000? Is there really a difference between 6,000 and 9,000? So, you know, look at— look at that and make sure you’re not using this number to get in your own way. 

And then don’t do what I did and just save I guess whatever you’re making side hustling. Because that could take a long time. Save your birthday checks. Save your bonuses. Save— you know, do a garage sale and put all that money towards it, like whatever. Go save that. Make that money. Save that money. 

So that’s a really big piece. And then I think the other pieces are that you have a website that you’re proud of that looks good and professional. And when you talk to people about your business, or you give them your business card, you’re not like, oh, yeah, but my website’s *mumble mumble mumble*. Don’t look at my page. 

And then this sounds obvious, but like a way for people to work with you and give you money. Have your product or offer there, and have it solid, and make it a price that will allow you to live and like not move in with your parents. And then obviously like some marketing tool that you’re gonna say, OK, this is how I’m going to drum up new business, get my— get more clients, have people in the world know who I am. 

And like those are really— oh, I should add health insurance too. Um, just figure out what that’s gonna look like for you. And if you’re not somebody who can jump on your partner’s plan, or you’re not still on your parents’ plan, then if you’re in America, google health insurance broker and then your state. Um, there are people that will help you for free. You don’t pay them anything. 

And you can tell them, you know, here’s my timeline. And I’m just looking— especially if it’s not immediate, you could just say, I’m just looking at my options so that I know how much money I’m gonna need to save or put away so that when I quit my job, the insurance piece won’t blindside me. Because it could be very not cheap.

HOST: Yes.

GUEST: She says with experience. So that’s a big piece too.

HOST: Yes, totally. And I’ll add about that— this is like a nerdy money note here. That if you have workplace insurance, if that’s a job benefit that you’re currently taking advantage of, and you leave that job, know that that’s technically a qualifying event. So if you wanna get insurance from the healthcare.gov marketplace or whatever, you can do that outside of the normal enrollment period if you have a qualifying event like leaving a job.

GUEST: Yeah, thank you.

HOST: So don’t think that you have to leave a job in November to get insurance through the marketplace.

GUEST: Right, right.

HOST: Just— just saying, if you’re thinking about that, talk to a broker. And they can definitely tell you about whether you apply and what the timeline might look like. And I wanna say there’s even a find a broker option through the healthcare.gov website, so—

GUEST: Oh, good. Oh, good. You know, I’m always amazed people do not know about the healthcare broker secret. And thank you for mentioning that with the timeline. That’s totally true. 

And, you know, you might also want— if you have an accountant or know someone you could talk to, keep track of all of your business expenses. Because obviously your salary will probably drop a little bit or substantially. And that might affect your— what you need to spend on healthcare in a positive way. 

[00:45:02] Um, so that could save you a lot of money too if you know like, all right, I’m predicting this much is coming in. And, um, but I also know that I’m spending this much. And here’s what I think I— you know, I’m gonna claim or whatever. Here’s maybe what I qualify for. 

HOST: Yeah. That’s a great point. Do you have any good resources or templates that you recommend? I mean, we talked about a few different things in terms of support structures. 

GUEST: Yeah.

HOST: So any— any ideas that you have to share about where people can find ways to help them with these items? That would be super useful. 

GUEST: Yeah.

HOST: And I’ll make sure all of this stuff— I always put show notes on my website. Whenever anything goes on the youngandscrappy.com blog, I’m always— you know, I wanna link back to those resources for folks. So anything that has like a link that you wanna share, we’ll put it in there. 

GUEST: Yeah, totally. Yeah, totally. Um, you know, I recommend for the savings account— and I think it’s really important to keep that goal separate from the rest of the money that you have in your checking account or your savings account. Um, you could go to capitalone360.com, or you could go to— I think it’s marcus.com— and open up a savings account for free that has like the highest interest that you could get. So those are two really easy like open them up online, super easy options. 

Um, score.org for anyone here in the States is a nonprofit made up of retired entrepreneurs that are in most libraries that you don’t even know about. And if you have questions about incorporating your business— and notice I didn’t say, in order to leave your job, you need to be incorporated. Because I don’t— like, A, not a lawyer so don’t follow my stuff. But, B, I was— I only became incorporated about three months— when I knew I was leaving my job, and I had bought an apartment and had property, I went, OK, now I need to be incorporated. 

So sometimes I feel like it’s not a mandatory thing. But a lot of my clients want to have that base covered. And because the incorporation rules vary from state to state in terms of how you need to register your business and stuff, you can make a free appointment with a score.org mentor. And they should be able to tell you what you need to do. Mine was able to just give me a one sheet. 

But there’s an asterisk with Score. Because the information you’re getting is only as good as your mentor. And I know— I’ve had clients that have had very hit and miss experiences. And also, since you’re dealing with retired entrepreneurs, sometimes I feel like their advice is a little outdated. 

So for example, they gave me a one sheet that said like, go to Staples, and buy this form, and then type it up in a typewriter, and send it like with a certified check for $10 to this place. You know? And I went, this form has to be online. Like it was 2010. But it wasn’t— 

HOST: Oh my goodness. 

GUEST: You know, and I was able to google that form. And I paid $10 online. Or maybe I paid an extra $2 and like was able to do it. So that stuff, maybe eh. But overall, it’s still a good resource. 

And then if you have the— if you need that debt calculator and stuff like that, I mean, I feel like you know more than I do about that stuff. I feel like, um, I had a link to like an MSNBC debt calculator or that sort of thing. But I don’t even think you necessarily need that. So I guess those are my— those are my big ones. The savings accounts ones that have the higher interest rate but cost you nothing to open and keep open and score.org are probably my two biggest that I talk about with this stuff. 

HOST: Awesome.

GUEST: Oh, wait. I just thought of one. Sorry. Um, Squarespace for your website. Squarespace for your website. Squarespace for your website. Don’t go looking at everything else. Squarespace for your website— the end. And that’s it. 

HOST: OK. Heck yeah. And, yeah, because I’m a huge nerd, obviously I’m gonna put my favorite debt calculator in the show notes. 

GUEST: Thank you. I wanna know what your favorite stuff is too, so I’ll be looking at that. 

HOST: Cool. So we talked about kind of getting things off the ground and starting to make that transition and all that good stuff. But what about growing your business? So not just, how long does it take to start your business? Because obviously that can be super variable. But also really scale it.

GUEST: Yeah.

HOST: And I think it might be useful at this point if you are comfortable sharing some of your own experiences here. So like how long did it take for you to really get things started? How long did it take for you to hit six figures, or make your salary back, or anything like that?

[00:49:55] GUEST: Yes. Yeah. So again, my timeline and experience is not what I say everyone else’s is. Um, I have had clients hit this sooner. I’ve had clients take longer to do this. It’s just really about your own situation and what you’re doing. 

For me personally, I made my base salary from my finance job in the first calendar year I was in business. So from March of 2010 to March of 2011, I made the $60,000 base salary that I had at my job. And that felt like a huge win. 

When I quit— this is worth noting. I had— so I quit in March. I think January, I made like $1,000 from my business. In February, I made like $1,500 from my business. In March, I made another $1,000. So I quit before I was able to make the monthly money that I wanted to make that would replace my income, just FYI. 

But once I was gone, I think that April was another like $1,500 month. And then May was like a $4,000 month. And then I was able to continuously make these like $4,000 months. So, um, that allowed me to make my base salary. So that was 2010. 

In 2011— 2010 into early 2011— in November of 2011, I got breast cancer. So this is also why like all— you know, my experience isn’t anyone else’s, hopefully. And what’s interesting is that my 2011 money was like very close to my— well, actually, my treatments happened in 2012. So in 2011— my 2011 and 2012 money was very, very close. 

And I was actually really proud of that because I scaled my client work way back. But I was still able to make about the same amount of money. It took me about five years to reach the six-figure mark. Um, and now I’m in the multi-six-figure mark. And I’m almo— I’ll be— I’ll be ten years out of doing this work full-time this March. So that’s kind of how my business has grown and how my money has grown. 

But again, it’s all about the time that you have to put into it and what you’re offering. And I like to tell my clients that they have to put and keep their Nancy Drew hats on. This is something that I say to everyone coming into Discover Your Dream Business. But I tell them that 11 years later, I still have my Nancy Drew hat on. 

And there have been, oh, countless number of courses, and offerings, and community sites, and programs, and whatever that I have started and ran and stopped and scrapped or tweaked or evolved or whatever along the way. And I think that that’s what smart business owners do. So I was really able to— it’s interesting. I’m one of the only coaches that I know that really thrives and loves like one-on-one work and has a successful business with not having like big programs that a thousand people are in or whatever.

I really like keeping things small and intimate and having that relationship piece. Um, so that’s how I’ve grown my business in a way that will allow me to serve as many women as I can in that particular way. So it’s interesting. 

And I love my work because I get to see so many different business models. And I could work with four photographers who have four very different businesses and offerings and price ranges and business models. And that’s all really fun. 

HOST: Heck yeah.

GUEST: Yeah. 

HOST: Heck yeah. That’s very good.


HOST: Um, so you have taken us on a delightful journey. We’ve covered all kinds of stuff— how to quit your job, how to find your dream business, how to get your s**t together to make that happen. Anything else that folks should know? Any other parting wisdom that you have for us? 

GUEST: Oh my gosh.

HOST: Is it— you know, just a little question here, just like, you know— 

GUEST: I know, just a little— no pressure.

HOST: Just rack your brain. 

GUEST: The first thing that pops into my head is it’s a marathon and not a sprint. And if you treat it that way, um, I feel very strongly that baby steps build the strongest foundation. And just don’t— if you’re a perfectionist, if you’re a people pleaser, if you’re an impatient New Yorker like me, don’t— like ease up on yourself. 

[00:54:50] And remember it’s not about how fast you go or how quick you get there. It’s— it’s building the strongest foundation possible and continuing to show up and do the work. So just remember that it’s a marathon and not a sprint. And you’re gonna get where you’re going in probably a better way that way. 

HOST: Yeah. That’s great. 

GUEST: Uh-huh.

HOST: All right. So you work with folks one-on-one. You’ve mentioned courses. 


HOST: Tell us— tell us about your work. Where can people find you online and hire you? 

GUEST: Yay. Well, find me at whenigrowupcoach.com. You’ll see there— hopefully, I’ve made it really easy for you to figure out like where you should go on my website from there. So there’s a discover bucket, and a launch bucket, and a build and boost bucket. So just follow the images on the home page, depending on where you are in your dream business journey. 

And then, you know, my Discover Your Dream Business program is something that is on demand. Applications are always open. You could start at anytime. It’s an eight-week program. It’s my most affordable program. Um, and I really stand behind that work. I’m super, super proud of it. 

If you’re in the launching mode, I have a one-on-one program called 90 Day Business Launch that does exactly what it promises. It gets you your mission, your message, your marketing, your milestones, and your money. So that, from our first day together till 90 days later, you’re able to have that plan, launch your business. I’m super proud of that too. 

Um, and then if you’re in the building and boosting place in your business, where you’re working in your dream business, but you know you wanna take it to the next level, I have a one-on-one offer called Boost Your Dream Business. And then I have a small group, six-month mastermind that is closed now because we just started the 1st of July. But you could sign up for the list there, and you’ll get notified in November when I open it up for the January to June 2020 round, which feels like it’s not that far away. 

Uh, so that’s how I work with my clients. But just head to whenigrowupcoach.com. And if you’re on the social media, you’ll see a link to my Instagram. And I also have a private Facebook group. So just follow those links, and you could— you could be my friend and my follower and blah, blah, blah. 

HOST: Awesome. Yay.

GUEST: It’ll be fun. Yay.

HOST: Well, thank you so much for your time. It was— it was a delight. 

GUEST: Aw. It’s my pleasure completely. This time just flew. And like now when we’re just friends forever, so we’re gonna grab our ukuleles and our double-L names and just like— it’s gonna be great.

HOST: This is a jam. This is a total jam. 

GUEST: I love it, love it, love it.

END CREDITS: I hope you enjoyed this episode of the Young Scrappy Money podcast. If you want to read about my work as a financial advisor and financial coach, you can do so at www.youngandscrappy.com. That’s www.youngandscrappy.com. Thanks again for listening.


Financial anxiety got you down? Looking to replace some bad financial habits or build better ones? We've got your back!

Simply enter your name and email address below, and we'll send you a pile of our favoritest, juiciest tips on paying down debt, budgeting, saving, and more!

Thanks for subscribing! We'll send you an email with your PDF guide shortly!

Share This