Turning 40 and Realizing Sometimes Failures are Successes in Disguise

Melissa DaSilva realized she was the only one working towards – or even interested in – the dream life she and her husband talked about. Then came the pandemic and forced togetherness, which made them realize they weren’t well suited as partners. So at 39, after 14 years together and 8 married, she asked for a divorce. And while that experience was hard, it allowed her to pursue a life that truly fits her and makes her happy – and one that builds in room for naps, which she considers necessary for her success. And now that she’s over 40, she’s less concerned about what other people think about her decisions, which she says is so freeing.

Guest Bio

An Expert in creating authentic lifestyles through unconventional ways of things and developing roadmaps to get there, Mellissa is a sought-after public speaker and educator who leaves her audiences feeling understood, entertained, and inspired to create change. Melissa’s success wasn’t achieved in the typical sense. Growing up as an artist with a learning disability, she found her unique path for creating wealth and a dream lifestyle while developing programs to address the mental health needs of the LGBTQ+ community and creating physical NFTs that make an impact on our changing world.

Career Inspiration

Melissa DaSilva was an introverted teenager struggling with mental health issues after her parents’ divorce. She credits a school social worker for getting her through high school, so much so that she thought “I wanna grow up and be Tracy someday.” 

She pursued social work in college and graduate school and feels lucky to have been in touch with Mrs. Lamb, her fourth grade teacher through school. As someone who struggled with a learning disability, she struggled with collecting her thoughts and writing papers. Mrs. Lamb graded most of the papers she wrote for her master’s program, making sure that they were coherent and well written. Her social work internship was working under Tracy in her old school. 

After getting her MSW degree, Melissa became a school social worker at a performing arts high school so she could “be somebody else’s Tracy.”  Before long, though, she realized she didn’t like working for other people and she knew she needed a schedule that allowed for her to fit in naps, which she says is a part of her constitution. 

Dating My Best Friend’s Brother

When she graduated college, Melissa started dating her best friend’s brother, which naturally caused some ripples, especially since her best friend said they’d never last. They got married after dating for six years. Her husband was very supportive of her career and her desire to start her own business. They bought a house and Melissa helped to take care of his disabled mother. 

So now Melissa had a career, a supportive partner, a house, and free time. And, while this is what “everybody says you should want when you grow up,” Melissa found herself unfulfilled. “But there was one night I was laying in bed and I just felt so empty.” She felt like there must be something missing; this couldn’t be “it.”  

Melissa had been vocal about not wanting to live in Rhode Island forever; the winters don’t agree with her constitution and the summers aren’t long enough. She wanted to figure out how to move somewhere warm, like Puerto Rico, but she realized she was more excited by that dream than he was. 

Then came the pandemic and, like many other people, they had to spend a lot of time together, which made them realize they probably weren’t the best partners even though they loved each other a lot. While they had always been “Team DaSilva,” she realized it was more “Team DaSilva but Melissa is pulling a lot of the weight.” That opened her eyes to the fact that her husband had been addicted to substances – either marijuana or alcohol – for the entire time they had been together. After her eyes were opened, she started seeing other things, too. As she reconnected with friends during the Covid lockdown, she realized she like talking to people who she shared interests with, and that she and her husband didn’t share many interests – or friends. Then she started to feel resentful of having to take care of his mother because he had his own stuff going on. 

Conscious Uncoupling

Things came to a head after an argument on her 39th birthday over, of all things, Facebook. Shortly thereafter, she realized the marriage wasn’t working for her and asked for a divorce. While they still loved each other, and continued to support each other, it wasn’t a ‘forever match.’ 

“People say, “Oh, marriage is forever,” but when the institution of marriage was created, “forever” was like 20 years. Not 80.”

Melissa took the opportunity to spend some time in Puerto Rico and eventually moved there. She runs her business remotely; she’s made great friends; and she’s able to pursue her art. 

The decision to get a divorce was hard because Melissa felt like she had the life so many people want and she worried people would think she was a failure. She doesn’t feel like a failure, though. “It was good for the time that we were together, and what it needed to be, and now we’re both free to evolve into the people that we need to be in the future.”

As they made their way through their “conscious uncoupling,” they realized they probably shouldn’t have gotten married, but it seemed like the inevitable next step based on where they were in their relationship. 

Melissa wonders if she was ever fully ‘in it.’ She says they never shared a bank account and, while she had access to his account to pay bills, he never had access to hers. She had a deep-seated fear that she needed to be able to survive on her own and she knew she didn’t want to end up like her mom did after her parents’ divorce. So while she was being protective of herself, she thinks that may have prevented her from opening up fully. 

As she moved through her late 30s Melissa realized that she was having a lot of depressive episodes. Her ex was supportive when she didn’t feel well, but she was experiencing more days when she couldn’t get out of bed. Even when she visualizes that time of her life now, she sees it as a filter of gray over the thoughts of what her life used to be. 


Melissa’s mom will say about Melissa, “You never do anything like normal people do; everything’s different.” Melissa thinks that’s part of being an artist: she sees things differently and makes decisions differently and lives her life outside the traditional path.

While she’s not a traditionally trained artist, Melissa loves to create and was amazed and delighted to find people were interested in buying her artwork. Today, she realizes that if she’s not creating art, her life probably isn’t running well.  

Starting a Business

After pursuing the school social worker career, and realizing she didn’t like it enough to stick with it, Melissa opened up a private mental health practice focused on LGBTQ+ community. While she was working in the school, she worked with a student who was transitioning and there weren’t any providers to support that person, so she became that provider. She geared her practice to helping people in the process of transitioning gender or dealing with gender issues. 

The business exploded and Tracy, her school social worker, is now her Chief Operating Officer. She runs the business from Puerto Rico and now spends most of her time supporting and coaching therapists who want to start their own businesses. 

One piece of advice Melissa has, whether in business or in life, is to remember that other people’s perception of success and failure will be different than your own. She considers her marriage a success, despite the fact it ended in divorce. She considers her career a success despite the fact she’s not still working as a school social worker. 

“We have to remember to be okay with ourselves and our own decisions, because at the end of the day, we’re the ones that have to lay down with ourselves, and be happy with who we are and what we did for the day.”

As we get older, not caring so much about what other people think is truly freeing. 


Melissa considers napping a crucial component of her success. Whether she’s having a down period mentally and physically, or she just needs to decompress, she takes a nap. She structures her day so that she has time to lie down after lunch. She scheduled appointments around her naps. And sometimes she will need to clock out for the day because she’s not feeling well. Building a life where she can be open and honest about her needs and surrounding herself with supportive people enables her success. Finding your tribe goes a long way towards allowing you to be your true and best self.


The Forty Drinks Podcast is produced and presented by Savoir Faire Marketing/Communications

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Stephanie: Hi Melissa. Thanks so much for joining me today.

Melissa: Hi. I'm so happy to be here.

Stephanie: I'm to have you as well. You are coming to me from sunny glamorous Puerto Rico. Is that right?

Melissa: Yes, I'm just in my new San Juan apartment. I moved here to a new location this week, so yeah, you have my first interview here in my new office.

Stephanie: Well, is very exciting. And I wouldn't have known for a minute that this is a new place for you because you already have beautiful art on the wall behind you. So it looks like you're at least settling in a little bit.

Melissa: I do that very fast. I have to get things all settled in so I can function like a human being.

Stephanie: Yeah, I understand. We're doing a little project in one of my rooms upstairs in our house right now. And there are boxes everywhere and we're building furniture and I have felt just a low level anxiety all week for having to go into that room. So I understand. But we're not here to talk about moving today, we're here to talk about your 40 story, which I'm very interested to dig into. Tell me a little bit about your background. Where do you come from and what made you, who you were as a young adult?

Melissa: So I was born and raised in Rhode Island, very close to Boston. So that's why I sound very Bostonian. I grew up there in a small town with my mom, she got divorced from my father when I was 10, so we lived a very, simple, poor life for a long time. I went to school, struggled with some mental health stuff, had this really awesome school social worker, Tracy, who I feel like got me through high school and I was just like, I wanna grow up and be Tracy someday. So I went to college, I went to school social work, also struggled with learning disability, so it takes me a lot longer to write papers, get my thoughts out. But I was also lucky to still be in contact with my fourth grade teacher throughout my life, and she actually graded a lot of my master's program papers. She would go through and edit all them so that, you know, I could hand in legible pieces of work. So I had to thank her for getting me through grad school.

Stephanie: That's unbelievable.

Melissa: But between Mrs. Lamb and Tracy, I ended up doing my internship for social work underneath Tracy. So I got to like work with her too where I grew up. So I became a social worker and I worked in a school because that's what I wanted to do. I wanted to be somebody else's Tracy and I worked in a charter school where it was performing arts, so I got to sing and dance with the students, but then realized that I don't like working for anybody and I definitely need a schedule where I can take a nap anytime I need to. It's just who I am; it's a part of my constitution. I'm just a professional napper. So in that process, I was like, I think that I need to start my own business.

Melissa: My husband at the time, he and I met when I just graduated college with my bachelor's in social work, he was my best friend's brother - that caused a lot of issues, especially when we decided to get married six years later, 'cause she said we would never survive. We were together a total of 14 years, and he was very supportive of me throughout everything, doing the school social work, deciding to start my own business, we bought a house together, I was taking care of his mother. She was disabled. It was like what everybody says you should want when you grow up, right? You got the career, you got, a partner, you got a house, you get free time. We decided we never wanted children, so we could travel.

Melissa: But there was one night I was laying in bed and I just felt so empty. I was like, there's something missing, this just can't be it. And I had spoke with him a lot about not wanting to live in Rhode Island forever because I don't like the cold. It's awful. It hurts in the wintertime, summer is only three months out of the year. And I said "Let me figure out how we can make it where we can move somewhere warm, like Puerto Rico. I'll make a lot of money and you could be a kept man, and we could just move somewhere together." I think I was more about that vision than he was. And then when COVID hit and I think this happened for a lot of people, we started having to spend a lot of time together and realizing we probably weren't the best partners. The thing is, is that we loved each other a lot. We were always Team DaSilva, but really, it felt like it was team DaSilva, but Melissa was kind of pulling a lot of the weight. Then it started, I started realizing like he has been addicted to substances, marijuana or alcohol, for pretty much the entire time that we were together. Things started coming out that I didn't realize, and it just kind of started to fall apart, especially when I started reconnecting with old friends during COVID and realizing like, oh, I enjoy when people enjoy talking about the same things I wanna talk about and do things that I wanna do. And my ex-husband was into other things, sports and hanging out with his sports friends and stuff like that. When I sat and looked at it, it was like, we don't really have much in common. We like watching three TV shows, we just sit in front of it and eat, and that's it. We don't share many friends, I don't think we shared any friends, my best friend at the time, and him barely had any conversations. I felt kind of resentful that I was taking care of his mother. I was doing a lot of the emotional lifting with that, because he had his own stuff going on. On my 39th birthday, we had gotten into this little argument about Facebook and he hadn't realized that we weren't Facebook friends for years. And all of a sudden he was like, "Oh, I didn't even realize that." So then he's my Facebook friend. And then he starts like posting on my page, which it felt like he was trying to like almost claim ownership, like, "Oh, what a wonderful wife" and stuff like that. Where is this coming from? This isn't working for me. And at that moment, I was like, I think that we need to consider a divorce. And it just really happened really fast after that. We talked about it, we had to go and talk to his mom, almost like a child and say "We're getting a divorce, it's not you, we still love you, but we're not the right people for each other."

Melissa: To this day we still say that we love each other, we know that we can rely on each other, but it just wasn't a match forever. I think about when people say like, "Oh, marriage is forever," but when the institution of marriage was created, forever was like 20 years. Not 80.

Stephanie: Okay. Fair point.

Melissa: And so I was like, okay, so that was our starter marriage. We'd never had any children, so it was really easy to separate. He's always known that I wanted to move to Puerto Rico, and I said I'm gonna take this opportunity, go spend some time in Puerto Rico. I booked an Airbnb for five weeks. He was in charge of taking care of the house because I took care of the house most of the time otherwise. And I decided to stay, I rented another apartment, I would fly back and forth to kind of settle things. And here I am today in Puerto Rico where I run my business remotely. I have great friends, I have my business, I'm able to do my art.

Melissa: It was a hard decision to make because it was the life people want, right? And feeling like people are gonna think that I'm a failure because I had this great life and it should have been forever and I should have been happy. But the thing is, is I wasn't. And you know, and I hope that he finds a partner that likes the stuff that he likes. I want the best for him. And I know he wants the best for me, and I don't feel like we failed. It was good for the time that we were together and what it needed to be, and we're both free to kind of evolve into the people that we need to be in the future.

Stephanie: Yeah. Wow. Wow. That's a lot. That's a lot.

Melissa: Yeah.

Stephanie: I'm gonna take you back and dig in, in a couple of places. You said that your ex-husband was the brother of one of your best friends. So this was somebody you had known before you were involved romantically.

Melissa: A very short amount of time because we were best friends in college. And so I had only known his sister for about a year and he was also in the service, so he was deployed. Throughout our dating relationship, he was deployed six months at a time, and I would take care of his mother when we were dating too.

Stephanie: Wow. That's a lot of responsibility to jump into.

Melissa: Yeah. Yeah. I'm very codependent. I've learned that about myself.

Stephanie: Oh, that's interesting.

Stephanie: Okay. So you start dating and you guys were together for six years before you got married and then you made the decision to get married. Tell me about that period of time where you felt like this was the right match and someone you wanted to spend your life with. What I'm really interested in digging into is this transition that so many of us go through around age 40 and we'll get to yours, but I wanna understand. Tell me about how he was the right person at the time or how you, put yourself together to fit there.

Melissa: When I talked to him throughout the, the, we called it conscious uncoupling, because we didn't like the D word because for us, it had very bad memories to it, both our family being divorced. And when we kind of processed it a little bit, we both said like, we probably shouldn't have gotten married. We knew that it probably wasn't, well, it was good for both of us, but it was like, well, what's the next step? We were just at this crossroad, we lived together, we had a house and my name was on it, but his wasn't on there, so that had some tension under it, so it was just kind of like, well, this is the next step we take in our lives. Like you're gonna be 30. Even when he proposed to me, it was in the subway of Boston, I was like, oh, okay. It was like surprise, but interesting surprise.

Melissa: We had a destination wedding, we didn't invite anybody. But I don't think that I was ever fully in because like we never shared a bank account. I would have access to his bank account to pay part of the bills, but I never shared mine with him. It was always this fear of, I need to be able to survive on my own, because I know things could go down and I don't wanna end up in the same situation my mother ended up with with having a kid and not being able to survive and just trying to make ends meet every month. I refused to be like that, so I was very protective of everything. I think sometimes doing that, you stop yourself from opening up fully to your partner. I think that's probably like one of my mistakes in that relationship was just not feeling that I could fully put myself into it and not recognizing that at the beginning, and saying like, "Well, if this is the thing, then maybe it's not the right relationship to say you're gonna spend forever in. Yeah, definitely being codependent, creating myself as that caretaker was something that was really easy for me to do. Like, "Okay, you're getting deployed, I'll take over. I'll help out. I'll drive 45 minutes to help take care of your mom because she needs this or that." Very easy for me, so that was a learning process. To this day I still have to kind of stop and say, "Hold up, you're dating somebody who also has a mom that lives with them. I think this is a pattern that you're repeating Melissa."

Stephanie: Okay. So you guys are married for nine years. How was it that it started to dawn on you as you're getting closer to 37, 38, 39... How is it showing up for you that this is no longer fitting?

Melissa: I think it was I was having a lot of these depressive episodes. So I also have bipolar too. And so I go through phases of being very manic and then other days of not being able to get out of bed. I have to say for my ex, who was very supportive of me in that, because he knew, he would say, "Oh, you're not feeling well today." And I would like, "No, I'm not." And so he would know to gimme a little extra loving care. so he was very supportive in that, but I found that for a while, I was getting more of those days where I couldn't get out of bed. I just didn't wanna do anything, or I have these feelings where I just wanna kinda scratch my skin off and just feel like I just keep on just taking it day by day and nothing's changing. It was just a lot of that. And even when I visualize it in my mind, it just seems to be gray, like this filter of gray over these thoughts of what my life used to be. And I think that's when things started to kind of decompose for me.

Stephanie: As you're in that place of not feeling well and feeling everything's gray and doing some of that soul searching, did you ever ask yourself when you were happiest? And I'm curious to know when it was.

Melissa: I don't know if I asked myself that, but I had recently had an experience where I went on my first business conference, and I went to the Philippines. I go big when I decide on a decision. And so I felt like I was amongst other people like me, other entrepreneurs, other people who thought differently. And that was when things, I was like, I want that more, fortunately in Puerto Rico, there's a huge community of entrepreneurs here, other podcasters, and I just knew I felt good amongst people like that. That's what I wanted. And I think he understood that as well.

Stephanie: So the path you were on sounds like maybe it was a little too traditional, too boxed in for what you really wanted.

Melissa: Yeah, you know, my mom's a little nuts, but one thing she will say about me, she's like, "Melissa, you never do anything like normal people do, everything's different." And I think that's a part of being an artist too, I just see things differently and make decisions differently and live my life very differently.

Stephanie: Yeah, and we haven't even dug into that yet. So tell me a little bit about being an artist. How long have you been an artist?

Melissa: I think all my life I've been an artist. People always say, "You're not gonna make money being an artist." I'm not a traditionally trained artist, I just create what I feel and see what comes out from it. I like upcycling. My father taught me how to use tools when I was older, cause we reconnected when I was in my twenties. And so we had that in common for a while before he passed. So that like keeps me connected to him is like creating something outta nothing. I started selling my work and I was like, "Oh my goodness, people wanna buy my stuff?'

Melissa: Now I'm creating art all the time and just wonderful things come of it, and I realize when I'm not creating art, everything else in my life isn't running the right way: my therapy business isn't smooth and fulfilling or my social life doesn't feel fulfilling. Art is always a foundation for my life and I have to make sure that I continue to keep that as a part of my life.

Stephanie: That's an amazing realization to know of yourself. When you were talking and telling us about your late thirties and being in that place I was very curious to ask you what your art was like during that time.

Melissa: I was building more stuff. I was taking tables that I found on the side of the street, repainting them, putting Frida Kahlo on them, or creating little tea boxes and painting them. When my ex-husband had to clean out the house, I'm sure he was saying some words under his breath when he had to take all my junk that I have taken off the sides of the street to throw it away. But yeah, up cycling was my thing back then, and then I would go to the farmer's markets and, sell my items that I've created. I created a bookcase out of dresser drawers and used that instead of buying a huge bookcase for my office, just setting them up in different ways so that I could use them for books and it was free. That's the other thing up cycling is pretty close to being free.

Stephanie: Right. And what's your art like now?

Melissa: There isn't much junk on the side of the road, or what I like to call sidewalk treasures, so now I work with alcohol ink on Yupo paper. It's ink that you move with rubbing alcohol and air sliding it back and forth. Working with that medium has really been great for me. We don't have like a Michael's down here or a Hobby Lobby, so I have to go up to the States and get supplies and then bring them down, so lots of smaller pieces right now.

Melissa: The pieces behind me are actually my pieces.

Stephanie: They're beautiful, I noticed them immediately when we jumped on. Do you think that the type of art you were creating at that time compared to now has connection to where you were mentally or emotionally, then and now?

Melissa: Yeah. I feel like back then, I was really trying to create like really tangible pieces, right? Like pieces that took up space, tables and chairs and hoarding things, because even my art studio started to feel like very hoarding. So it was almost like this feeling of, I'm comfortable amongst my stuff. Out there I'm not feeling comfortable with the people and stuff like that. So yeah, I would come home and it was a dining room, but who eats at dining room tables anymore? It was now my art studio. And so I just kind of hunkered down in there amongst my things.

Stephanie: And now you don't feel the call to create pieces with structure and tangible elements anymore?

Melissa: I don't have access to it and I don't have tools for it. I had to get rid of all my tools because you can't really move them down here. I just feel like the universe is saying, "We're moving on from that right now."

Stephanie: Tell me a little bit about your business. It sounds like you started a business at some point during your thirties. So tell me a little bit about what you were doing before you started your business and how it came about.

Melissa: I was doing the school social working thing, realizing I wasn't a big fan of that, after so many years of believing that's what I was gonna be when I grew up. That was another transition, too, of like, "Oh, Ah, this isn't what I'm gonna be when I grow up, because I don't like it." And being okay with that, opened up my own private practice for mental health and I geared it towards the LGBTQ plus community. When I was the school social worker, we had a student that was transitioning from female to male, and we couldn't find any providers in the area at the time.

Melissa: Realizing that was a need for the community, I really geared my practice towards helping people who were in the process of transitioning gender or figuring out what their gender was. So I started that. I went off to this conference in the Philippines, really started getting into the business mindset of things and figured out marketing is how I get clients and get lots of clients. Within two years, I had to increase the size of my business, hire more people because I was getting all these referrals. I ended up having about 23 therapists working for me right before COVID hit, and I was seeing my own clients too. We were really servicing a great population, we were starting to get into the schools too, because my background as school social worker realizing I needed to help the schools out 'cause I know that they need therapists in the schools. My COO ironically is Tracy, my school social worker, so we came full full circle.

Stephanie: I love that.

Melissa: Yeah. So now we work together and it's been a great experience. We have two locations now, I run it from Puerto Rico. I do more coaching of other therapists who wanna start businesses, and I also coach artists or creative thinkers in their own businesses. So I pivoted a couple of times in my life, the East Coast Mental Wellness has been something that I created, I love it. It's afforded me the ability to live the life that I live and help out the community.

Stephanie: Wow. That's amazing. I I'm blown away at how quickly and large your business grew. A lot of that speaks to the niche that you chose and the need there. That's amazing and as a business owner myself, I'm very curious that you're able to run it from afar. Tell me a little bit about that.

Melissa: It's about the team that I have. So I have, my assistant, Selena, she joined me a year into the business, as an intern for a school project and she has been with me ever since. I call her my Lady Sitter because she would keep me outta trouble. When we were working in person, she would be funny: she'd be "Missy, there's too many Mountain Dew cans in your trash." And then when I would get into those manic phases, I'm like "Selena, I think I need to hang a swing in my office because that'd be super therapeutic," and she'd be like, "I don't think that will work." Or I'll be hammering something at like seven in the morning and she'd come in she's like, "What are you doing?"

Stephanie: Wow.

Melissa: So she has been with me since the beginning, COVID hit we're now in two different areas, but we talk almost every day. She's now going to school to be a social worker. So watching her grow from an intern to now, asking me questions about ethical dilemmas and things like that has been really great. And because I don't have children, if I were to pass, I would want my business to go to her. I would want her to be able to have this. She has all my crypto passwords there's nothing in there, but if I pass away, you can have those $2. So I would say having that strong connection with Selena, having the strong connection with Tracy. We've traveled together. We work well together. I think that is what made it possible to be able to run this remotely and be creative in how we all do this because Selena doesn't work at the office, either she's in a different state. Tracy's the only one that's in Rhode Island still.

Stephanie: The people that you service, are you mostly servicing Rhode Island or are you now into Telehealth and servicing a broader audience?

Melissa: We do offer Telehealth, but it's to Rhode Island clients because of our licensing.

Stephanie: Sure. Right. That makes sense.

Melissa: It's been difficult because Rhode Island's such a small state. It'd be nice if we could like service other areas too, We have plenty of referrals right now, so we don't need to worry about getting out there.

Stephanie: Was going out on your own and starting your own business. I mean, obviously we can see from this point of view that you had a meteoric rise, was it scary?

Melissa: Oh yeah. It was scary last week, too. It's scary almost every day.

Stephanie: And how do you live with that?

Melissa: I usually cry in a corner somewhere and then take a nap and I get back up and be like, "You can do this, you can do this, there's no other option." And I know that my strength is that when things get hard, I rise to the occasion. If things are like kind of mediocre and I'm just kinda like doodle-ooh, then I'm just, but I know like when I need to rise, it will happen. But even at the beginning, I remember asking my ex-husband I'm like, "We're gonna make it, right?" He was like, "It's a little too late now to ask that." And I'll be okay.

Stephanie: Tell me about the calculus of leaving a steady job and going out to do your thing on your own and starting from scratch. I'm trying to get at almost an illustration for other people listening, who might be curious or who might think, "Oh, I could never do that." Either "I want to do that," or "I could never do that." I wanna illustrate the path for them a little bit.

Melissa: It was thinking about finances. I'm terrible at thinking about finances. I run my own business, I still hate thinking about finances. I'm a creator. I just wanna make things. I don't wanna think about anything else. But to sit down and think about like, okay, this is how much I need to make to survive. All right. So if I cut back to part-time at the school and then work part-time at the business. Okay. I can do that. All right. So now if I stayed part-time at the school, hire somebody else to work the hours that I'm not in the office, you know, trying to be creative about how to utilize the time and the space. Then when I had enough money saved, be able to step out and say like, okay, now I can do this on my own. And if I can't, what's my plan B. I always had to think of a plan B. I can't remember what my plan B was back then, but I didn't have utilize it. But even to this day, I'm like, okay, if, if tomorrow this all went to shit, what's my plan B.

Stephanie: I mean, for those of us who do run our own businesses, the plan B is just go get a job.

Melissa: Exactly.

Stephanie: Although that being said, I'm not sure many of us make for great employees, but you could always just go get a job, to get you through to the next, whether it was the next idea or the next great fit.

Melissa: Downgrade your life, figure out what you can cut, and then there's always something that you can do. It might suck for a little bit, but I know that I'm gonna take care of myself and I'm gonna be okay. And the cat, I don't know, might sell him to the sausage factory.

Stephanie: Okay for people who can't see the video. I just want you to know that her black cat just stood up right in front of the camera for a stretch. It was awesome.

Stephanie: Um, when I first started my business, the first six or nine months, you start saving your receipts 'cause everything's a write off. I had my desk and right in front of my desk, there was my printer and I would just stack my receipts on my printer because I, like you, I'm awful at the finance side, I cannot do numbers. So, it was like six or nine months, the stack got six, 12 inches tall and it just made me feel bad every day to look at it, cuz like how hard could it be to pop that in QuickBooks or put it in a spreadsheet or something. I just couldn't make myself do it and a coach said to me, "You don't have to do everything on your own. Figure out what it is you can't do, you absolutely can't do, and hire for that." So the very first thing I hired was a bookkeeper to just do the simple data entry and the accounting of the business, which I still to this day cannot wrap my head around.

Melissa: Oh, yeah, me either. My bookkeeper will ask me like "This and this?" And I'm like, "I don't know. That's why I have you."

Stephanie: two or three weeks ago my bookkeeper was in, we have been together, I don't know, maybe eight or nine years, she's the best. Um, and. I was saying to her, "This feels different this year, and I'm not understanding why this or that." So she's showing me in QuickBooks and she's like, "Okay, first let's look at it on a cash basis. Then we're gonna change this, we're gonna look at it on accrual basis and you can..." And the numbers were flipping and changing and, and she's telling me the whole thing. And finally, I sat back and I said, "I have no idea what you're talking about. Let me just ask you a question, does it make sense to you?" And she goes, "Yeah, it makes sense to me." I was like, "Okay, that's fine then, then nothing's awry.

Stephanie: Early on, one of my selling points, the first few years of my business, I used to say to people, "People start a business because they're good at or passionate about something. And that something isn't always marketing." And so that's where I came in, I was the person you would hire. So for me it was a bookkeeper for somebody else it was help with marketing. So for anybody who is thinking of going out on their own, or who thinks "I could never do it," the simple fact of the matter is that you can do it. Yes, it's a little scary. I like to think of it as there's just no net there, there's no safety net, but you know, at the beginning, you're not that far off the ground. So, the fall isn't that scary.

Melissa: And other people's perception of your success and failures is gonna be different than what you think your success of failures are. I think my marriage was a success. It doesn't mean it wasn't because it ended. I think other things are successful. Other people might be like, well, you went to school to be a school social worker and that's not what you are, so what does that mean? Or right now I do a lot of coaching and I ended up writing a book about how to start a profitable practice, all the stuff they didn't teach us in grad school, because people are good at being therapists or healers, but they're not good about the business side of things. We have to remember to be okay with ourselves and our own decisions, because at the end of the day, we're the ones that had to lay down with ourselves and be happy with who we are and what we did for the day.

Stephanie: Yeah and that's a big part of this transition between 35 and 45 is really learning to trust in yourself. Really learning to trust your own inner wisdom, your own decisions, your own intuition. Like you said, absolutely your version of success doesn't need to match anyone else's as long as you are happy.

Melissa: Yeah. And I think that's one of the most beautiful things of getting older, too. The act of being able to let go and not give a shit of what other people think it's been so freeing as you get older. And I know I'm gonna end up being that really old woman and be like, "I don't give a shit if you don't like what I say."

Stephanie: You said you've structured your business and your work and your life so that you can nap whenever you need to. Tell me about that.

Melissa: Yes. You know, it's. One of my most important things. I don't know. Maybe I have like the Chronic Fatigue Syndrome or sometimes I think like some people watch TV when they need to decompress, I just enjoy listening to murder mysteries and falling asleep and taking a nap. I kind of structure my day about one o'clock I might eat and then go lay down for a little bit. When I'm having those down periods, with the bipolar stuff, I need to be able to nap more so I'm able to schedule appointments around when I need to nap. I can even tell my assistant, like, "Listen, I need to clock out for the day. I'm just not feeling well. I need to go nap." And it's like, "Okay, I'll take care of it." Or I can call her up and say like, "I'm not feeling well today. I can't do anything. Can we handle it?" So just being honest and open about my limitations when they're there and having supportive people around me that'll be like, "all right, see you in an hour." Even when I worked in the office with everybody else, I'm like, "Siesta Time!" and they're like, "Okay, we'll see you in a little bit." There's research that shows that you are better productive after naps too. So once I read that, when I worked at the school, I was like, "I am going to take a nap every day." At one point I was napping under my desk, like George Costanza.

Stephanie: okay.

Melissa: I had like a little nest, I'd have like my yoga blankets and I'd just like nap for about 20 minutes under my desk.

Stephanie: That's hysterical.

Melissa: I would hear the kids knocking out my door. "Miss. Miss..." Like nap time. And they would come in and nap, too, 'cause sometimes what a teenager needs is just to take a nap.

Stephanie: Right. Yeah. It's interesting as you are younger, and certainly in the workplace, there's so much structure and so many rules and so many mores and standards that you have to follow and live up to that you don't think that coloring outside the lines is possible and in a lot of companies, it may not be,

Stephanie: there are pathways out there that allow for being weird. I'm just gonna call it that, being weird. Right?

Melissa: I do think COVID has opened that up a little bit more too. Yeah. We're like we see all you weirdos in your house now, so you can't hide it anymore.

Stephanie: Yeah. Just doing things that are outside the standard, there are pathways that allow for that. And even in some of those standard organizations, you can earn your way into that by succeeding and doing your job and being great at it, being a great part of the team. I'm guessing that as a school social worker, you didn't go in on day one or month three and say, "Okay, now it's time for a nap." It was something you probably earned your way into because you built your credibility, you built your persona of being a successful, hardworking, productive member of the team. Is that right?

Melissa: Well, I got lucky with this school social work job, because it was a performing arts, everybody's weird. The principal there who is now my best friend, I say he's like the second longest relationship I've ever had. Our interview was interesting because we talked about my master's degree program project, and it was studying gay-straight alliances in schools. He was like, "Well, I'm gay." And I'm like, "Okay" and so from there we just connected and he was an artist with ADHD and I'm like this artist that's kind of like bipolar and we just like really connected and, I would be like, "Steve, I'm gonna take a nap." It was like, all right. And then he's in my office taking a nap.

Stephanie: Oh my goodness. So that didn't help me with my illustration very well, but

Melissa: But if you walk into a weird place where there's other weirdos, it can work out really well. You gotta find your tribe.

Stephanie: Absolutely. that's a great moral of the story. Find your people.

Melissa: He came down here to Puerto Rico and helped me make this recent move. And I will forever be grateful to him. I mean, he and I were just sweating. We had no electricity, he's hauling stuff for me. We're laughing, I'm crying. He's consoling me. When I look back on my 41 years right now, I just think of these moments of great opportunities and great relationships I've had the ability to create, and I'm just so lucky and blessed that I've had these opportunities. Just having like a friend like Steve, to be able to come down here for four days and just sweat it out with me. I'm very, very lucky.

Stephanie: It sounds it. Let me ask you now a question that I asked you earlier and see if you have a different answer. If you think today about your life and when you've been happiest, is there a more obvious answer?

Melissa: I would say creating art and performing. Yeah.

Stephanie: That's great. So you've followed your heart and it's led you to a place where you can do all the things that you want to do. You can run your business, you can create art, you can be in a climate and area that inspires you, and that feels good for you. So it's possible, really is the bottom line.

Melissa: I tell people that every day. It's possible, it can be scary, but it's possible.

Stephanie: That's great. Well, Melissa, I just wanna thank you so much for being so generous with your story and letting me dig into your life a little bit. I think this has been a really great conversation and I thank you so much for being here.

Melissa: Thank you for having me and putting up with my menace cat.

Stephanie: Well, as you and I said before we started, we both have young male, black cats who are complete menaces. So watching it just takes me home and I think you and I should

Melissa: Right.

Stephanie: start a support group for each other because I literally was on the phone with my vet this morning about, yet another behavioral thing. So, um, yeah. you don't have to apologize to me for the cat. I totally understand.

Melissa: Thank you. I feel feel heard.

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