Portland Downtown

PPP005: I’m Melanie and I Quit My Job to Work for Myself

Today we welcome guest Melanie Lockert, a self-employed freelancer who quit her job in a non-profit to work for herself. She also happens to be one of our writers here at Personal Profitability.


Melanie bMelanie Lockert Dear Debtegan her career with plenty of student debt after attending college in California and graduate school at NYU in New York City. She moved out to Portland, Oregon hoping for the best, but found the job market leaving her wanting more. After struggling to find a non-profit job with a steady salary, she walked away to pursue her own online income dreams, where she now generated a full time income.

You can find Melanie’s work on this site, at her own popular and growing blog, Dear Debt, and many client sites around the web. You can find her on Twitter at @DearDebtBlog.

Resources Mentioned

Portland Finance Bloggers

Concepts Discussed

Full Transcript

Eric Rosenberg: Ladies and gentlemen, boys and girls, children of all ages, welcome back to the Personal Profitability podcast. I’m your host, Eric Rosenberg, and I’m so excited to bring our second guest onto the podcast today. Today we have one of the writers from our own website that you’ve gotten to know and see, our own writer, Melanie. She is here with us, and she is going to share a bit about her journey from working in the nonprofit industry and going on to self-employment and now she works for herself full time as an online freelancer. Welcome, Melanie, and if you want to say hi to the fans and tell them a little about yourself, go for it.

Melanie Lockert: Hi, everyone. Thank you so much for having me, Eric. I’m really excited to be here. I am a freelance writer, side hustle coach, editor, virtual assistant, and all-around side hustler. I love making money in different ways and have had quite a journey with the whole blog and writing adventure. So I’m really excited to talk to you about it.

Eric: I think that a lot of our listeners will have something in common with that ‘liking to make money’ thing. That’s something that brings us all together. Welcome and I’m so excited to have you not just as a writer but an audio voice for everyone to get to meet and say hello to. So everyone, say hello to Melanie, and just a quick pause for those who like to partake in my tradition of drinking a beer with us as we go through the podcast. Here’s your opportunity to press pause, go grab the beer of your choice and then come back.

Now that you’ve pressed play again—because I don’t know if you know, Melanie, I like to have a beer when I talk money as we’ve done at the bar a few times.

Melanie: It’s the best, they fit.

Eric: Totally. There’s no reason personal finance shouldn’t be fun. And beer is definitely fun.

Career in the Nonprofit World

Eric: So my first question for you, Melanie, if we can go back a little bit in your journey, how did you get started in your career and end up in the nonprofit world?

Melanie: I started in the nonprofit world pretty much right after college. I graduated with a theater degree, so you can all start laughing now, but I actually used my theater degree with arts education early on. So I was a theater teacher. I also was an arts administrator for a nonprofit program in Los Angeles. So pretty much for my whole career, I would say about the past nine years I was working in nonprofits in LA, in New York, in Portland—they were a variety of different educational services. There were a lot of arts-based cultural educational programs that I worked for, sort of managing programs, managing budgets, teaching, working with grants, administering city programs. The nonprofit world has sort of really helped me prepare to be a freelancer because you wear many different hats. You know, one day you are the janitor and one day you’re the executive director. You’re all working together to make something that is a highly imperfect work and you’re dealing with very limited funds. I’ve worked in a variety of different sectors in the nonprofit field, both in arts education and intercultural education, but a lot of it has been around sort of helping people really understand that you can transform your life through arts and travel. So that’s pretty much how I started my career for the past nine years and then fully transitioned to being a writer which I still see as a highly creative field.

A Realization of a Dream

Eric: Can you share a little bit more about how you ended up moving. I know you were a Californian for a very long time. I knew that you moved here to Portland. We’re actually both in Portland, different parts of the city, but for listeners we’re about probably two or three miles apart right now but both in Southeast Portland. So how did you move to New York and what drew you to Portland from there?

Melanie: Yeah, so the abridged version of that story—it could be a very long story—but the abridged version of the story is I’m from Los Angeles, roughly Long Beach, California. I sort of worked in downtown Los Angeles for the early part of my career. I actually got this work opportunity to go to NYU to sort of check out these programs that we’re going to bring back to Los Angeles for our high schoolers, and while I was there I just decided to check out a grad school program for myself. Sure enough, two months later after that trip, I applied to NYU and a couple months later I got in. It was just this weird thing that NYU had always been my dream school. I had written in my journal many, many years ago that “I wish I could go to my dream school, NYU, but I doubt that will ever happen.” Years later it happened, and so I had this really tough decision of leaving my career behind, leaving my family, my boyfriend, everyone to go to grad school in New York. I made that choice to do that. So that was a highly risky situation that got me into a lot of debt.

Eric: Did you keep that journal page? Did you frame it somewhere, that dreams do come true?

Melanie: I do actually because it was one of those things that I felt like I really manifested that reality. I was in a pretty dark place when I wrote that because I was just feeling frustrated with life and hoping for something better. It was kind of a nice way to turn out.

Facing the Consequences of a Risky Choice

Melanie: So I moved to New York, went to graduate school, had a lovely, lovely time there. Towards the end of it, after graduation I went on thirty different interviews.

Eric: Thirty. Though it’s not a record, but that’s a lot of interviews for sure.

Melanie: A lot of them were second, third, and fourth interviews and it was so close. It was so often between me and somebody else. During this time I also happened to be in a long-distance relationship. My partner, Ryan and I, we met in LA. I moved to New York to go to school. He moved to Portland to go to school, and so during this time we were doing a long-distance relationship back and forth from Portland to New York which also exacerbated things. So I graduated from grad school, had these thirty interviews in New York. They weren’t really panning out. I just thought, “I don’t know if I can go one more interview in New York,” and my relationship was getting strained. Maybe I should move to Portland to be with my love, and it will be cheaper here. It will be better here. So then I moved to Portland. So that’s the abridged version of this sort of tri-city adventure.

Eric: Well, I would say welcome to Portland but you’ve been here longer than I have. So it was very fun to come here and have Melanie—we actually have a little FinCon local meet-up group here in Portland. For those of you who aren’t familiar, FinCon is the financial blogger conference. It started like four years ago. I’ve actually been to all of them and gotten to know a lot of great people through that. That’s how I got to know Melanie was because of those connections with mutual friends in the FinCon world.

Melanie: I think Portland has one of the best FinCon meet-up groups. We have such a strong tight-knit community here which I love.

Eric: Totally. We have great people. If you want to go out there and check out some cool websites, Get Rich Slowly is one of the ‘granddaddy’ of finance blogs that was started by J. D. Roth who lives about— from where I used to live where, when I recorded episode one, probably about a mile from him. We have Kathleen, formerly O’Malley, she got married. And her blog, she actually has two blogs now, she had Frugal Portland which she still has and started a new blog called For Profit Blogging which she talks about how to make money blogging, the name’s pretty good.  Joe Udo is in town. He has a site called Retire by 40, and he’s been featured in the media quite a bit. He’s a great guy. We have quite a few active finance bloggers in town. It’s a great community.

Melanie: Yeah!

Reality Check

Eric: So another question for you then. So did you have a job when you moved to Portland or was it just I know that it’s going to be cheaper than New York and I don’t have anything in New York so I just want to try it out?

Melanie: So that’s where the story takes a downturn in a very interesting way. I came to Portland really feeling like a big fish in a small pond. I was like “I’m from LA. I just went to grad school in New York; I have a graduate degree from NYU. It’s going to be so easy to find a job in Portland and I’ve got this.” I got to Portland and the job market was way worse than New York, way worse.

Eric: Oh, it’s crazy here.

Melanie: So incredibly worse.

Eric: My wife had the same kind of experience when we left Denver and moved here. She thought, “Oh, I’m the experienced property manager. I’ve run my family business. I’ve worked for someone else. I’m going to walk right into something.” They say Portland is the city where young people come to retire. That’s actually kind of true. There are more over-educated people here working in coffee shops than probably anywhere else in the country.

Melanie: I know. It was an abrupt change for me to have thirty interviews in two months and really sort of feel that I was really close to something, but I just felt personally that it was time to try something different and then to come to Portland and just really struggle. I was actually sort of flunking up in that the first two weeks I was here; I did find a part-time job. It was a ten-dollar-an-hour admin assistant job at one of the arts nonprofits.

Eric: Making the big bucks for that master’s degree to use.

Melanie: Oh my gosh, I have a master’s degree and making $10 an hour. It was pretty tough but you know, I was happy to have work, and after that I sort of upgraded and made $12 an hour as an educational adviser for students who were studying abroad. But that was a seasonal position that sort of gave out six-month contracts and then they didn’t rehire you for three months because they didn’t want to call you an employee and then they would hire you again for six months. Then after that, I finally, after a year-and-a-half, got a full-time job as an events coordinator. It was just wild because I had thirty interviews in New York right away, and in Portland I was applying for full-time positions for a year-and-a-half and I had five interviews that whole time. I finally got that one job as an events coordinator at a nonprofit and I just thought my dreams came true. I was the happiest person alive to get that job at that point. A year plus later I quit that job to be my own boss. So it’s kind of ironic and in this big adventure, I looked for this job for so long; I got exactly what I wanted. I thought it was my dream-come-true, and then like most dreams, you achieve your dream and then your dream changes when you realize it wasn’t all it was cracked up to be and you try something different.

Debt Journey

Eric:  So before we get into what you did next, when you quit that job, I know you mentioned student loans from NYU which is not a cheap school to go to. I know from the name of your blog that you have, Dear Debt, that you had some debt come along the way, so how did your debt evolved over time from when you moved to New York until you left your job?

Melanie: So my debt journey has been quite varied. I went to undergrad at Cal State University Long Beach, a very affordable state school, and I graduated with $23,000 in student loans.

Eric: Which is a relatively manageable number for student loans in the scheme of things.

Melanie: Yeah, it was definitely manageable, but I was pretty clueless at that time so I just paid the minimum like most people do, thought that’s just what you should do. Then until I actually applied to graduate school that I realized ‘oh my goodness, I’m going to really get myself into a lot of debt doing this’ that I really realized that I had to do something differently. I’m embarrassed by this number, but I took on an additional $58,000 in student loan debt to go to NYU.

Eric: Had you paid off any of your original loans yet at that point or was this just adding to the pile?

Melanie: I had paid off about $13,000 just paying the minimum over three or four years. So by the time I graduated NYU, I had $68,000 in debt. You do the math, $58,000 plus $23,000, it’s a total of $81,000 that I’ve had in my lifetime. As of May 2011 when I graduated, I had $68,000 in student loan debt. Currently I have $34,000. So I [inaudible 0:14:29.5] this journey of paying the minimum and not really seeing it as any sort of burden. Graduate school sort of woke me up. I realized that I didn’t want to pay off my debt for 25 years and have it forgiven when I’m 52. I didn’t want to just feel like this constant nagging feeling. I know that I’m working really, really hard to put upwards of 40 and 50 percent of my income to student loan debt and really slew there as fast as possible, but it’s worth it to me so that I can be debt-free in just a few more years.

Eric: So when you were in New York living from your student loans, did you have any credit cards along the way or were you just sticking to the student loan debt?

Melanie: Just student loan debt. I actually didn’t even get my first credit card until two years ago. Even though I apparently so easily got into student loan debt, I have actually always hated debt and especially the idea of consumer debt. I just never really understood it. So I proceeded very cautiously and didn’t even get my first credit card until two years ago.

Eric: So at least your interest rates were staying pretty reasonable. So for those of you listening who aren’t as familiar with student loan debt, if you get it through a government student loan, the rates are fixed by the government so you’re not going to pay super high interest rates. You can get some private student loans with a higher interest rate, but they’re still generally pretty reasonable. With credit cards your consumer debt can often be by 20 % or more. A lot of them start at around 15 %. So the interest rates are much higher so it makes it a lot harder to pay those off. So that was good news that, Melanie, you didn’t have any credit cards along the way so you don’t have any of those to pay off. That’s a great story.

Melanie: Yes. Just student loans.

Eric: ‘Just student loans’ is easy to say but that’s a lot of money too to pay off. I was in the same boat. I actually got undergrad I was on a full-ride scholarship because of what I did with Boy Scouts so I got through that without any debt. My first loan I ever took was a car loan because my car died on the way to work one day; it just turned off, and the repair would have cost more than the car. So I went and got a new car which is still my car that’s sitting out front, my Toyota, but when I really got my first real taste of debt was also in grad school when I went and got my MBA at the University of Denver. And I ended up taking about $40,000 in student loans for that. Because of my career stuff, people who are interested in reading the story, I’ll put in the show notes a link to my post about how I paid it off in about two years and six days. If my payday had been one week earlier I could have said I got debt-free in less than two years, but I’ll always say ‘two years and six days’ thanks to that payday being one week later.

Melanie: That’s fun though.

Eric: So there is this story.

Melanie: Very exact.

Eric: Two years and six days later I felt in my heart like I’d had a flyover at the Super Bowl and have jet fighters fly over. It was like, ‘yeah, I conquered my debt!’ When you do pay your debt off, I’ll call in some favors and see if we can get a flyover over Portland for you.

Melanie: I’m planning on partying. I already know I’m going to host a party.

Eric: Dance party?

Melanie: You’re invited. Dance party, karaoke party. I’m just going to have a big party because that’s just such a huge amount of money to pay off and I’ll be very excited.

Eric: You’ll have all this free money now that you used to be paying into your debt. You can now just put it into a party fund.

Transition to Freelance Work

Eric: So you had your job in Portland and you started freelancing on the side while you were working. When did you start your online income and how long did it take from that point until you quit your job?

Melanie: This is really interesting is that I just started freelancing actually officially the first thing that ever made me any money was October 2013.

Eric:  And was that before or after you started Dear Debt?

Melanie:  I started Dear Debt, January 2013.

Eric: Okay. So was your blog a part of how you found the freelance client or was that totally unrelated?

Melanie: It was definitely how I found my first freelance client. He had found me via Twitter and invited me to write an article, and so I was so thrilled and so terrified. I had been writing in my blog for almost a year by that point, but I just felt “oh my goodness, this is the first time I’m writing for pay. I’m going to make it perfect.” Yeah, it was an interesting experience, but it didn’t really catch on until a few months later in February 2014 is when I really got sort of serious about it.

Eric: So you started building up your income from freelancing while still working at the same time which is what I’m doing. It’s what many freelancers do. If you don’t mind sharing, how much was your nonprofit paying you at the time that you were also freelancing? So what were you trying to build on?

Melanie: So I made $31,000 at that nonprofit job so not an incredible amount of money. It seems like an incredible amount of money coming from ten to twelve dollars an hour.

Eric: Totally. A salary is a nice thing even if it’s not a Wall Street salary; it’s still a salary.

Melanie: It felt really nice at the time. I just really wanted to prove to myself that I could at least match my nonprofit job. I tell this to people a lot that I had sort of a lower barrier to entering that way. I would never suggest someone who’s making $100,000 or $90,000, or maybe even $60,000, really seriously think about quitting your job to freelance because you do obviously want to be making that same amount of money or ideally more. For me I didn’t have a ton of money that I was going to be replacing, and I really believe in myself that I could do it. So I was hoping to get $2000 a month after taxes, and in a matter of months and really, really busting my ass, I was able to make it happen.

Taking the Plunge

Eric: What steps did you go through from that first freelance client? How much were you making roughly a month freelancing when you decided it was time to leave the job and go out on your own?

Melanie: I quit my job in July of 2014 and at that point I was making I think about $1500 a month. So not quite exactly what I was making, but I had just secured this new client that wanted 20 hours a week of SEO writing and so I decided to quit my job to pursue this. Actually, it’s really funny, the SEO job turned out to be awful and totally not worth it and it just felt like another job. I ended up quitting that sort of that very lucrative side gig two months later and thought ‘You know what, I can be writing a lot more articles and spending a lot more time making more money’. I’m so glad I did that because I started making a lot more money right after FinCon essentially. I made a ton of different connections at FinCon. I really started hitting the pavement and sort of networking and really reaching out to people. I think the difference the between my income has always been direct action. What steps do I take to build those relationships that I already have, to create new relationships and to also continue to deliver a really great product so that people are seeing me? It’s been really great to be featured on a number of different platforms including your website; including your podcast as well as other people because then you’re sort of getting out there and making a name for yourself. People start coming to you, which I found, sort of the best of both worlds instead of constantly pitching people and really trying to hope that someone throws some money at you. It’s really great when people come to you. I feel like you have a lot more power and can leverage sort of increasing your rates because of that.

Eric: I totally agree. I actually have a fun story about that at FinCon. I ran the Ignite FinCon event; an ignite event is a speaking event where people get on stage and they have exactly five minutes to the second; it’s timed. They get twenty PowerPoint slides on a 15-second auto advance, so it’s kind of like Ted Talks on speed, and I planned that at FinCon. Last year was my third year doing that in New Orleans and somebody approached me right after the event when I did my talk. I did the last talk and one of the things I said was ‘I’m a freelancer and I’m for hire’. You don’t want to pitch yourself too much to that audience, but you can’t help but mention it. Someone walked up to me at that event and they became a great client who’s been great to work with. You never know where someone’s going to find you. Events like that are a great place. So I’ll ask you about that. How many FinCons have you been to or other conferences, and how did you meet people there. Did you have any networking tactics? What was the thing that really helped you jump up from there? As you said, that was really your launch point to growing your income.

Melanie: This is actually my first FinCon. It was awesome and so very exciting to be around so many other people that love personal finance. I am an extrovert, I love meeting people; I love talking to people. So I really felt like I was able to shine at FinCon. I know some people that are more introverted, sort of have a hard time. It can be very overwhelming, I’m sure, to see hundreds of people that you may or may not know online. But for me I just felt I’m here to learn from people, I’m here to grow. I’m here to learn about what other people can do and learn how I can help others. Definitely just meeting anyone and everyone. I gave everyone I that talked to a business card, not in a spammy way but at a certain time in the conversation when it felt like a right thing to do, ‘here’s my business card by the way. I would like to talk about ways that we can follow up and catch up.’ The key thing that I did, that I think really, really helped is after FinCon, I spent about four hours emailing every single person whom I met at FinCon.

Eric: That’s an investment of time right there, four hours.

Melanie: Every single person. It wasn’t sort of a mass email thing. It wasn’t something that I was just emailing to everyone. It was literally a unique email with notes about what we talked about or things that we had mentioned, really showing gratitude for that moment in time that we shared together, just following up with ways that we can collaborate. And that warranted so many great results. I felt like at least 20 percent of people responded with a new opportunity. Also I really learned to be really vocal. Two or three of those people who had contacted me at FinCon and we sort of had follow-up emails afterwards, they had this sort of really vague, “Yeah, let me know how I can help you or how we can help each other.” And I said, “Yeah, actually you can help me. I’m looking for [inaudible 0:26:05.5] clients; I’m looking for this. I’m looking for that.” That was kind of hard for me to do, but it felt so great because that warranted results. It really just proved to me that you really need to speak up and tell people what you want. No one’s a mind reader. You can’t assume they read your site or they know anything about you so you have to really tell people ‘look, this is what I can do, this is what I need. This is how you can help me. Let me know how I can help you’.

Eric: Everybody listening to this isn’t a personal finance blogger so just so you know out there, if you do any other kind of online work, there are tons of conferences out there that are more general or specific on different topics. There are mommy blogger conferences and mommy bloggers—I know a few of them and have seen their financials and they make tons of money. It’s mind blowing how much money they make. They can make in a month what I make in a year and I do pretty well. There are conferences called Blog World Expo for a long time. Now it’s called New Media Expo or Media World Expo. It’s in California or Las Vegas. There is also a podcaster conference; so there are conferences for everything. So don’t feel just because we’re talking about FinCon here that there is no conference for me in the freelance type of work that I do. There are conferences for people who do anything—techies, anything you do there is a conference for you. My brother-in-law who runs an excavator company and he went to a concrete working expo in Las Vegas. It was a great place for him to make contacts for his business. So really there is a conference for everything. For me, like Melanie, it has been a massive part of how I’ve grown my income so much and met people and built those connections and the credibility and everything that comes with it. So don’t be afraid even if you’re on the introverted side to throw yourself out there and try it and get involved, volunteer to help with the conference itself. The more people who know your name and know what you do, the more likely someone’s going to email you just like they did to Melanie and say, ‘Hey,  I’m looking for a new writer for this site, what do you charge?’ That really does happen, and it’s a pretty cool experience.

Charge What You’re Worth

Eric: So when you started freelancing and you were brand new, didn’t know anything about it, what were you charging people at that time?

Melanie: I actually had no idea about rates and someone had just emailed me and they said I’ll pay you $25 for a post. I said, ‘Great! That’s awesome! I thought I had made bank at that time. It was, ‘wow! I can write an article in an hour and $25 is going to be awesome’. At the time, because I was so new and I was not experienced and things really do change once you start making money doing something, I was paralyzed with fear. I just thought oh my goodness, I’m so nervous to submit this, and this article that I thought was going to take me an hour ended up taking me about three or four hours. At that point I’m probably making about minimum wage or less after taxes. At that point I had been charging twenty to twenty-five dollars a post, and I was just totally inexperienced. I figure everyone has to pay their dues and work some of those lower rates and really understand what your time is worth and how you can grow from there and then also being really realistic. I learned the hard way about dealing with paralyzing fear and getting past doing something for the first time. I had no experience freelancing before. I thought people are going to see me, and they’re going to understand that I’m a fraud. I’ve never done this before, and they’re going to think my article sucks, and it just took away from my time and money. As I kept going I kept just saying I realize that I would turn my article and no one would say anything. I’m like well, no news is good news. You keep trying and you realize that the world’s not ending and everything is going fine. You start to build up your confidence and realize that a lot of that BS is just in your head.

Eric: Just so you don’t feel bad, my first paid post that I wrote was for $10.

Melanie: That’s making the big bucks.

Eric: So you were making about three times what I was, and so like you, my rates have gone up over time. So if you don’t mind sharing a range—I don’t want you to give away your trade secrets on what you charge—but what types of ranges did you see coming in, in newer clients that you’re taking on?

Melanie: It can definitely be a range. I prefer to work with people budgets because that has been a really great way for me to actually sort of leverage a higher income without having that sort of awkward negotiation phase. That happened with a client at FinCon actually. I had decided to sort of get rid of the whole rates thing and sort of ask what their budget was. They just floored me with their budget. They said fifty cents a word.

Eric: Fifty cents a word? That’s like magazine writing right there.

Melanie: Yeah.  I thought it was a typo at first and so I just played along. It was like that sounds great. On the inside I was dancing and screaming in my living room. I got paid for that assignment for a blog post about $400. That was something that really blew my mind because I feel like you sort of work with these rates that you think are sort of normal. In the freelance-writing blogosphere, $10 is obviously on the very low end. Beginners is around the $25 range. A pretty moderate range is around $50 -$75 per post. If you’re a real expert and you can bring a lot to the table, probably a $100 to $200. There is a definite range of rates you can use as a freelance writer, but that experience was one time but it really just showed me that you don’t know what people’s budgets are. It’s always helpful to ask, and you could be selling yourself short if you don’t. It just showed me that there are really well-paying clients out there that you just need to find them. So essentially the short answer is a rate between $50 to hopefully, several hundred dollars a post. That’s what I’m really trying to focus on next is getting those $200 to $400 posts and really having the confidence to charge more and to seek people out. For newer clients that do come my way, sort of just saying, ‘this is my rate, and this is what I want’. I’ve found more times than not that people who really want to work with you; they don’t even flinch and especially if they’re a professional or a corporate-sponsored blog. They have the funds to pay.

Finding a Mentor

Eric: So a little story from me. When I started freelancing and really getting serious about it, which I put it on my monthly entrepreneurial income updates how much I’m making from different parts of my online business, one that has really grown over the past couple years is the freelance writing for other sites. I did sponsorships on my own site for a long while and then I discovered this great world of freelancing. Someone who really helped me along the way, there’s a writer out there named Jason Steele. He is probably the biggest credit card/frequent flier mile freelancer out there who isn’t writing solely for his own blog. He has done amazing things and not only helped me plan trips with miles, but he really led the way to me to knowing how much you could make freelance writing online. He was a big inspiration to me at helping build me up. So did you have any stories or anyone who really helped you build up your business and you looked up to as a mentor? Did you kind of go at it on your own and figure out the waters yourself?

Melanie: I have to give a shout out to Carrie Smith from Careful Scents. She has been such a fantastic mentor to me. We started working together in April of last year, and I started on as her assistant editor for her site as well as for one of her other sites that she works for. We just really had this great relationship and I just looked up to her so much. She would answer my questions. We would have Skype dates and mentorship sessions. She was the one who really pushed me to quit my job even before I was ready. She said that sometimes you have to leap before you have all the answers. I really do think it was the right thing for me to do at that time. She has had a wonderful success story. She also quit before she was ready, and it has worked out amazingly well for her. So she has always been pushing me to charge what I’m worth. She’s always so appreciative of everything that I do. She has really been so helpful at sort of explaining some of the things that I just clearly don’t understand as a new business owner.

Eric: Do you think you could have come as far as you have without that mentor relationship or do you think—

Melanie: No.

Eric: That was a quick no.

Melanie: I would probably still be at my job if it wasn’t for Carrie.

Eric: That’s a great thing to say for mentors. I have a similar experience, not quite as close a defined mentor relationship with Jason, but he was definitely a leader and a friend who helped me along the way. It was a great experience for me.

Advice on Launching a Freelance Career

Eric: So if you were to start over today knowing everything you know now, and you wanted to start a new freelance business, what would you tell the Melanie of two years ago, ‘this is what you need to do to get started’?

Melanie: Number one, I would say, ‘just do it’. I can definitely resonate with that feeling of being paralyzed by fear and feeling like you’re not good enough and sort of comparing yourself to other people who have been doing it way longer than you. There are so many great freelance writers in the personal finance sphere that it’s so easy to be like, ‘oh, there’s already a ton of writers out there. Why do I matter? Why should I even start?’ But I think just getting started and doing what you do best and really cultivating your voice and not comparing yourself too much. I would have definitely found a mentor sooner rather than later. I was lucky enough to stumble upon Carrie, but if you don’t have a mentor, try to find one. I can sort of resonate with what you said too, Eric, is that they might not consider themselves a mentor to you but as long as you are getting something out of it, and you think of them as a mentor, it doesn’t have to be an established relationship or this formal thing. It can just be something that gift that someone has given you. Number two, is something that I’m dealing with right now, is definitely being more organized in the way that business is set up. I’m doing my taxes right now, and I have not kept very good records. I’m really sort of learning that it would have been a lot more helpful to be more organized with my records, my bookkeeping, actually having a business checking account, and I’m so embarrassed to actually say that I don’t have one yet.

Eric: But if you need help with any of that offline let me know because I actually just set up my third business checking account. I’m actually going to pitch a topic to PT for this FinCon to do a talk on this exact issue because I’ve run into so many people who started their own businesses but didn’t treat it like a business up front. They’ll go on just making a few dollars freelancing and then years down the road they’re still cashing checks under their personal name.

Melanie: Seriously. I really didn’t get it before but now I totally get it now that I’m dealing with this sort of nightmare figuring out where all my money went. You now, some of it came from PayPal, some of it was with checks, some of it I didn’t get to 99s because it was less than 600 dollars. I’ve been scrolling through all this stuff and it’s just been kind of a nightmare. Now I’m seeing that a little organizational work on the front end would have really saved me a lot of headache now. In that regard I have to say that I consider myself a very creative-minded person, and so my brain just short of shuts down at these things. So I’ve sort of delayed the inevitable in that regard. I think that through people like you that have done it and can explain it easily for people like me, that’s a great thing to offer because some people they do feel more sort of creatively-inclined and aren’t good with this actual business sort of stuff, and that’s definitely me.

Eric: I’m kind of a free kook who kind of likes doing my own bookkeeping and accounting because it’s kind of fun. I guess that’s why I have two finance degrees, and I used to be an accountant because that’s what I do.

Work-Life Balance

Eric: So one kind of fun question, working for yourself full-time, what is your typical work uniform and do you ever work in your pajamas?

Melanie: When I first quit my job I have to say that I took a lot of naps and worked in my pajamas a ton that first month. I just felt like, ‘oh this is awesome, going to work in my pajamas and [inaudible 0:39:32.4] and take lots of naps’. At that point I was also recovering from working 80 – 90 hours a week and so literally was just exhausted. Sort of as I recovered from that exhaustion from working so much and managing a full-time job as well as my freelance career, I started to realize that it was kind of unhealthy to work too much in your pajamas. I think it can be nice, but I sort of hit a point where I was working in the bed or working from the couch just in my pajamas and it was really affecting my productivity actually. I started to think about why is it so hard for me to focus and I realized that when you’re in bed in your pajamas, your body language is telling you, ‘I’m relaxed. Everything’s cool. It’s casual’, but in your brain you’re trying to focus, you’re trying to write, you’re trying to do business. And there’s sort of this disconnect of what your body’s telling you and what your brain is telling you. After that point I realized I’m saving the pajamas for days that I’m sick or literally too exhausted to get out of bed. I just wear jeans and a T-shirt. I don’t really dress up. Some people say that you should dress up in business wear and whatever. I don’t do that but at least get dressed in real clothes.

Eric: Do you go to a coffee shop or do you work from home more?

Melanie: I mostly work from home. If I feel like I need to get outside I do go to a coffee shop. I like working at coffee shops, but I also feel like I can get distracted there. I love people-watching and sort of wandering. So it really just depends on the day. I would say primarily I work from home from a desk and that was the big shift that I made when I sort of realized I wasn’t at my peak. Productivity was getting dressed properly every day, sitting at a desk properly every day, really setting up my personal space at home to be conducive to working. Because a bed and a couch is not conducive to working.

Eric: I get that totally. I do try to write on the couch every once in a while with a TV show in the background, and my words-per-minute go from like a 100 words-a-minute down to five words a minute.

Melanie: Exactly.

Eric: Sometimes when Desperate Housewives is on Netflix you’ve got to do what you’ve got to do. So anyway, you’re awesome, and we’re real life friends so I could chat with you all day, but the podcast listeners don’t have all day. They have a lot to keep themselves busy and starting their own freelance businesses. So if they want to find you and connect with you on the web, on the social media, where should they go to find you?

Melanie: They can find me at I’m also @DearDebtBlog on Twitter, DearDebt on Instagram, DearDebt on Pinterest.

Eric: That’s great brand naming. If I had known that when I started all of my blogging stuff six years ago, I would have probably had an easier go of it than just changing my blog name like I did a couple months ago.

Melanie: It would be a tough transition.

Eric: Well, thank you so much for your time here and all that great knowledge and your story that you shared. Lift up your beers everyone and say cheers to paying off debt. And thanks so much for being here. Everyone have a productive and profitable day.







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