Transcript: How to Earn $500000 on Upwork with Freelancer Morgan Overholt.

Transcript: How to Earn $500,000 a Year on Upwork with Freelancer Morgan Overholt.

Welcome to the Holistic Wealth Podcast, I’m your host, Kesha Blair, wife, mother of three, Author of Holistic Wealth and Founder of the Institute on Holistic Wealth. The show will showcase various experts in the key pillars of holistic wealth. Each week we deliver the best information on how to become holistically wealthy and live your best life.

KEISHA BLAIR: Today, we have a very special guest with us. We have Morgan Overholt and she is the founder of MorganMedia LLC, a concierge graphic design firm for clients. And she also does coaching for Upwork Freelancers now. Morgan’s story has been very popular because of her work on Upwork. She actually earned over $400,000 (now $500,000) on Upwork. She also advises other freelancers on how to supercharge their freelance careers and land jobs. Morgan, welcome to the show. It’s great to have you.

MORGAN OVERHOLT: Thank you so much, Keisha. I am honored to be on this list and on this podcast with so many other incredible women who have gone before me.

KEISHA BLAIR: It’s great to have you. And so I just wanted to start this episode with getting into the backstory. So I know you had your job, your cooperate job, and you weren’t being fulfilled and that’s what caused you to make the switch. So can you tell us a bit about that?

MORGAN OVERHOLT: Yes. So first of all, I have pretty much always been interested in graphic design. When I was 13, 14 years old, back when the internet was still on the dial-up, you know, we’re all familiar with that, that sound that it made. I would spend my summers literally just goofing off on the internet, working on different projects for myself, like my Harry Potter fan site, or, you know, playing around with Microsoft. I think was the freebie software at the time, you know, and it’s hilarious because I have always just kind of had an interest in doing that sort of stuff with design and even a little bit of web design.

Back then, in the early 1990s, mid 1990s, it wasn’t necessarily even something at least that my parents saw as being something that was going to be fruitful later on in life. In fact, more often than not, I used to get in trouble for hogging the landline. I was kind of a geeky little kid. So that was my jam. I mean, little did I know at the time that teaching myself essentially employable skills I would use for a lifetime and it was actually those skills that got me my very first part-time job, right out of high school, doing graphic design for the local office max. And after that I spent the next decade or so working my way, doing freelancing through college on the side, of course, at the time I’m doing graphic design for my full-time corporate career for almost a decade before finally, eventually into finding my way into freelancing full-time, which is basically what I do right now. So it’s been a journey.

KEISHA BLAIR: And that’s amazing because we’ve seen where the Passion Economy, which I’ve spoken a lot about in the past too, you know, using hobbies and skills to make money on the side is something that people are doing now. So it’s amazing to hear your story. It’s amazing to hear how these hobbies and interests can turn into a monetized skill. So, Morgan, it was always just a passion and then you landed into the corporate world and then you realized it just wasn’t for you?

MORGAN OVERHOLT: The funny thing is Kesha about this is that I almost kind of got to the point where I blamed graphic design for holding me back. And I quickly realized that was completely unfair. For instance, the first five or six years of my corporate career, I was working full-time as a graphic designer, still freelancing a little bit on the side, but the full-time was of course my, my primary income and for a long time, that served me really well.

I was doing pretty well for myself but then it started creeping up into my late twenties and I felt like I hit a wall and I’m sure a lot of women have also kind of experienced this. I started seeing other people – whether it be because of at least the way I perceived it as being nepotism or perhaps even gender bias – people who I perceived as having less experience than myself who were, getting raises, and getting the promotions. Even managing me. And it was really, really frustrating to me at the time. So I did what anybody would do. I switched to hosting a television shopping network for a while. I say that tongue in cheek, obviously, but no, seriously. I blamed it so much in the graphic design that I actually attempted to completely switch my career.

At the time I had actually been working behind the scenes as a graphic designer for a home shopping network. And I had spent years listening to these people, sell stuff on TV. And I felt like, gosh, how hard could it be? I’m kind of a chatter box anyways. So, well, you know, I could give that a shot. I saw a full-time position open up for a full-time show host at the nation’s biggest jewelry shopping channel, like in the US, this is a big deal. And I just applied thinking, okay, this is my big break. If I just switch to my career, that’ll make me happy. That’ll bring me riches. You know, I’ll be good to go. I can totally do it. Funny story. I got the dang job. I became full-time and for three years I did that job as a home shopping host, but that’s where I actually learned the biggest lesson of my life. It was never the graphic design holding me back. Really. It was me. I made this gigantic career shift.

I still wasn’t happy and I was downright miserable by the time I took that job because hello, whoever thought hosting a TV shopping network, what’s going to be a cakewalk is crazy. Your alarm goes off at two o’clock in the morning. Most mornings you gotta be hair and makeup ready by like four or five. You’ve got to go on TV and act like you are happy to be there. Even if you’ve not had your morning coffee. You’ve got serious goals to hit and I actually took a pay cut temporarily to take that job because I had this promise of promotion and I thought it would all be okay. So I took a pay cut back and, you know, and after three years of working even harder than I ever had before and not sleeping well, not to mention the fact that I never saw my family. I never saw my husband. I mean, by the time I was getting ready for bed every night at 6:00 PM to hit that 1:00 AM wake up call, he was just getting off work. We were like passing ships in the night.

I worked every night, every weekend. It was not any kind of life to live and it’s funny because I even, sometimes I listen to myself on another podcast or I read like a blog that I wrote early on when I first made the switch into freelancing. And I still very much blamed, I think the home shopping network or blamed all the people I felt like were holding me back and sure there were definitely some individuals that were less than helpful, but it’s a large part. It is really my fault because I never really trusted myself to go into business for myself to do those things for myself because I was too busy, blaming all these other little circumstances around me from holding me back.

And basically what happened is I got in one morning and I basically quit my job. I was just like, I can’t do this anymore. I’m out of here. And I walked out and I don’t recommend anybody doing that. This is definitely going to be do, as I say, not as I do. That’s just the point that I was at my life.

KEISHA BLAIR: And that’s amazing Morgan, because so many women have left the workforce due to COVID-19 and they’ve experienced and have been experiencing the same thing that you experienced, you know, being overlooked at work. More women are micromanaged than men at work, and then we’re juggling or home life, kids, marriages. We’re juggling all of that on top of everything in the corporate world. And it’s so amazing to hear your story, because I think so many women can identify with that story. And so, Morgan, you mentioned when you quit, so was there a plan? Was it just cold turkey without saving?

MORGAN OVERHOLT: Well, okay. So luckily and I call it rage quit because technically speaking, it was really kind of an expedited plan, if you will. Like, I had gotten to the point about six months prior where I had the heart with my husband, he was actually also part-time contracting then as a programmer. And I said, all right, look, I don’t think I’ve got a whole lot more of this in me. So Let’s like have like a one-year plan here. Let’s, let’s save up a little extra and then you can go to full-time contracting or you can find a full-time job, whatever, you know, so you can become the stable person. And that will allow me to make this switch. And we had this whole like one-year plan hilariously.

We were even in this one-year plan going to like remodel our home a little bit and go take care of some of those home improvement things we didn’t put on the back burner. And, you know, so we could sell it and a whole whopping five or six months into that plan, I was asked to do a nine day straight from my employer with no breaks. It was the day after Easter. I worked a double on Easter as well, Easter Sunday. I hadn’t just FaceTimed my very young nieces and nephews, who had to explain to for the umpteenth time, why aunt Morgan wasn’t at Easter and kids don’t by the way, don’t understand. Oh, I have to work, but that’s not something that registers with a five-year-old as I’m sure y’all know.

And it’s heartbreaking to tell them that. And, in the morning after the shift, I’m working Monday straight. I had a meeting with my boss previously scheduled and I got into the meeting and I swear to you, she goes, yes I wanted to talk to you more about being in the office more frequently. I have to sit here for nine days where I don’t know what happened.

I don’t know if I blacked out. The next thing I know, she started to open up this vanilla folder with all these great plans she had for me and how I was going to give even more of myself to the company. I was like, I’m so sorry, I’m going to stop you right there. I was like, my heart’s not in this anymore and that is the line that I used. And honestly, it was the most truthful line I could have used at the time, because it was, it was honest, you know, the heart was not in this anymore. And she goes, are you saying you’re ready to walk? My husband at the time was like ringing my phone, the entire meeting.

Because apparently our bathtub had come in for the remodel, like while this was going on. So like he’s literally knee deep in a remodel at home. You know, not thinking I’m sitting there quitting my job, not having a midlife, early midlife crisis. None the wiser, you should have seen the look on his face when I came home. So luckily, to answer your question, I did have a little bit of savings, but even more importantly than the savings, as I mentioned earlier, Because I’ve always been a freelancer in some respect, like, when I was in college, I was just earning like a couple hundred dollars month and freelancing not much, but hey, a lot to a starving college kid. That’s like a ton of ramen. I knew freelancing was something I wanted to explore full-time at my husband’s suggestion because he saw, I was pretty naturally inclined with it already and thought I could be more successful at it.

I had taken what originally as an adult became like a or originally was earning about a thousand bucks or so a month, freelance income from working nights and weekends, in my spare time to $4,000 a month before I quit. Like so funny because when I did give myself that intention those few months prior to, you know, permission to eventually quit my job, it was a little quicker than I expected. I had to put effort into building that up. And so I did already have a decent sized amount of freelance income by the time I even quit my job, which of course made it way easier to quit. Right. It’s way easier to be like, I’m not going to spend one more day here.

KEISHA BLAIR: I get it. And as you’re talking, I’m thinking about financial resilience, and there’s so many people out there who’ve invested so much in their jobs and their nine to five. They’ve given everything they’ve turned up day after day. They haven’t even put their attention on something else that they might explore, like a hobby they might monetize or how they could freelance on the side, because they’ve been hyper-focused on giving their employer, just everything, just everything.

And then when things turn and then there’s nothing else, the salary goes, then everybody’s wondering, okay, what do I do? And so Morgan, like, I’ve seen your story about your success on Upwork you’ve earned like $400,000 ($500,000 now). It would be amazing to hear how you built up that success. And of course, tips for people who are just going on Upwork. I’m sure it’s far more oversubscribed than when you started. So that’s what I wanted to get at too, was like, well, if I sign up for Upwork now, or somebody else signs up for Upwork, who’s listening. Are there like these hacks or like tips to really stand out on the platform?

MORGAN OVERHOLT: You’re speaking to the Upwork, Jedi over here, I’ve got this covered. Literally there’s anything. It’s so funny because you know, when I was talking about earlier making that leap, and I know it probably doesn’t sound like a, a super scary leap when you’re already getting about four grand of freelance income, but in all honesty, that was unusually high for me to be able to hit $4,000. And just doing that on the side, in between working day shifts. I did have a unusual record month for myself, but honestly, that’s the thing I would recommend doing. Before you, you know, worry about Upwork tips or specific platform tips, if you are brand new to freelancing, you need to dip your toe into the water.

And if you have no experience freelancing, it’s unlikely. I’m going to be honest that you’re not going to find a lot of success or at the very least feel a lot of comfort on a platform like Upwork. It’s very active there. Yes. There is some competition. Yes, there are a ton of clients. I actually think the most difficult thing on Upwork isn’t fighting off your competition, sorting through. You know, the good and the bad clients, it’s almost kind of like a dating website, you know, do you swipe right or left? Because there’s a lot of people and forgive me, what’s the bad swipe. I always forget. Is it the left or the right? You get a swipe the bad way.

There’s a lot of people forgive me. I’m not of the Tinder age, but there’s a lot of people that you’re better off just not dealing with. And I get to tell you if it wasn’t for my experience as a freelancer who had been doing on the site and knowing how to speak to these clients and knowing what kind of jobs suited me, I think I would have drowned on a platform like Upwork.

So to be honest, that is the number one thing that you can do. But with the aesthetic, I realize that’s a lot easier said than done, right? Because you’re like, well, where do I get my first client? And that’s just with mostly a lot of really good old-fashioned work. You know, when I was younger, I was lucky since I’ve done this for a very, very long time and, and felt a natural passion towards it.

In fact, my very first freelance client actually came from OfficeMax. Because back in the day I was the only one, I was 18 years old working at office max and I was the only one in the entire building who knew graphic design. And so each of my bosses didn’t know graphic design, we worked in the copy and print section, you know, he could not open Photoshop, he couldn’t really do it. Even as a part-time employee, we had customers coming in, asking for me. Or waiting on me to get to work. And when I quit that job to switch colleges, I transferred to a four-year university where I actually had clients who tracked me down and said, Hey, would you just work with me on the side?

And then that snowballed. And then they would tell their friends and their friends would tell their friends and. And that’s the hilarious thing about a lot of my really early work. I didn’t even really go after it. Freelance almost sort of happened to me more or less than, than I actively pursued that in the beginning.

It was almost kind of meant to be in that way. If I were coaching somebody who was brand new to the world of it tomorrow. You know, I would say start out by, especially if you have very little experience, start out by volunteering for your friends or your family or a local business, or perhaps a nonprofit organization. Those are really great non-profit organizations. They always appreciate, you know, a bit of a discount are always willing to help. And those people honestly have some of the best connections. Oh my gosh, they can get you hooked up. And just because it’s nonprofit guys, down the road does not mean that they do not pay.

They also have funding. Most of these nonprofits, that’s a really great way to start. And I don’t usually preach working for freaky HSA, but I do think if you’re brand new to it, that’s kind of how you start to make connections. If you have no prior experience, no portfolio. I think it’s definitely something to consider just to network, you know, it’s to do a little something here and there and let them see what you can do.

Then they’ll come back for more. And that’s probably what I would do starting tomorrow. Now I have forgotten your original question. Your original question was about Upwork, right?

That it was very important because if you have not done that first, like I said, Upwork will eat you alive. Okay. So just dip your toe in, get used to talking to clients, get used to pitching clients, and most importantly, get used to asking for referrals. If you take one thing from this podcast, Get used to asking for referrals because you’ve got to do that in the real world offsite. And you’ve got to do that in the real world on site. And that right there is the difference between a successful freelancer and that’s what wins you, quality clients and the clients that come to you off of referrals are usually much more grateful. They’re usually I find more well-funded they’re easier to work with.

And they also know what they’re getting into with you because they usually they’ve seen what you did for, you know, so-and-so friend or so-and-so colleague. And, and so there’s not that wall in between you that sometimes you have, when you meet strangers online, that you don’t know whether or not this is going to be a good relationship.

They’re like, Oh yeah, that’s more again, I saw the thing she did and that looked great. And it’s exactly what I want and I trust this relationship going into it. And I find it so much more smooth, going in. So get used to kind of doing that. When I joined Upwork, it was actually on the recommendation of my brother-in-law, who was already on Upwork at the time.

I hadn’t even heard of this platform before. This was brand new to me. So this was like the wild, wild West. I didn’t know what I was getting into, but he seemed to be making some pretty decent money, working in tech, on Upwork. And I started Googling different stories about freelancers. I read a lot of good stuff. I read a lot of terrifying stuff. I tried to focus more on the blog posts and the stories of people who had been successful. I think that’s another really important thing to do in freelancing and in business, focus more on people who have achieved the thing that you want to achieve and who have been successful at it rather than listening to the naysayers.

So that was the biggest thing that I did in the very, in the beginning. And I think that really paid off after that, it was just a lot of persistence and hustle. It is the hardest thing to do on Upwork is get, get a couple of first reviews on your profile. Once again, if you’re brand new to Upwork, nobody knows you from Adam, right? You got no reviews or you might have a limited portfolio. You basically have to say to the world, Hey look, I’m awesome. Believe me, look at all this stuff like these other clients are saying about me. Look at this robust portfolio. Your job is to convince these potential clients that you are you, the woman for the job.

And so you have to do whatever you can do to get those first couple of reviews on the board. For me, I decided to try to look for jobs that I knew I could do really quickly. And that wouldn’t be much of a risk. Like for instance, I would apply for jobs like, you know, 20 bucks to convert a rest or to a vector or $5 to do a logo tweak or $10 to like lighten this photo.

I would almost kind of look for stuff like that, that I knew wouldn’t be a huge time investment just in case we suffered from scope creep or something like that. You know, it just in case it went South, because once again, I don’t know what this whole platform is going to be. I try to take moderate risks, you know, and that strategy, ultimately, that really panned out for me. I will also say though it took a lot of applying. I mean, when I first joined Upwork, even though I was applying for small jobs to get started and just to get a couple of reviews, I mean, gosh, I probably applied for three to five jobs every day for two weeks. Like each day it would be three to five different jobs every day.

And two weeks later I finally got a nibble. And it was an offer for 10, a $10 vector tweak. And you know, did the $10 set my world on fire? not necessarily, but what was really great is I got a five-star review. He gave me invaluable advice, which will be the next piece of advice I talk about actually, that I’ve always taken to heart since doing that job.

And after I got my first five-star review, you know what? The second client, didn’t take two weeks to come in, it took two days to come in. Then the third client was the next day after that the fourth client was the next day after that. And with every job, my rate went a little higher. My responsibilities, you know, got a little more. The jobs got a little bit bigger. The clients got a little bit bigger and before you know it, my first year, I believe in January, I believe that that following year, I hit the six-figure mark on Upwork, pretty crazy. And today I’m actually now borderline $500,000. That’s $500,000 earned within the next month or so.

KEISHA BLAIR: Wow. That’s amazing. So those are big strides from going from six figures to what you’re earning now. And so you mentioned a critical piece of advice that someone gave you. So I’ll let you go into that before I ask my other question.

MORGAN OVERHOLT: Yes. So this is the other really big piece of advice. So right now, right, I’ve already given you two, right? Recap. Get some freelancing experience, even if it’s just doing something for the mom and pop shop down the street, whatever it is, or aunt Sue or cousin, Jenny. Get some kind of experience. If you have none, you know, make sure you’re applying for jobs frequently, even if it’s something really small, because you have to get that first review on the board.

The third piece of advice, and this is absolutely critical for work is focusing on longer term clients. Now, I’ve done plenty of one-offs. In fact, you’re probably going to do more one offs in the beginning where it’s just a one and done, instead of something that turns into a multi-month contract. For instance, if you do try to make a point in focusing on an ongoing client relationship, your work becomes more steady. Your income becomes more predictable. Your relationships become greater. Honestly, I found the greatest amount of respect from, and to the client and the best relationships I’ve formed have been off of long-term contracts. And most importantly, on Upwork, of course, the dreaded fee, right?

Because everyone freaks out about, Oh, well there’s a 20% fee on Upwork. Well, my average fee, because most of my clients are now been with me for several years is felt five to 8% and five to 8% is really nothing in the grand scheme of things. I always tell people, look on her, feel shark tank, but every time I’ve watched shark tank, he’s people are like, yeah, I’ve got a 15% margin on my product.

And they’re like, That’s all right, guys, I’ve got a 93% margin on my product, right a 93% to 95% margin on my product. And it’s not just the Upwork is bringing me these quality clients. Cause I’ve worked for big name clients that I found on Upwork, including Black and Decker, Kimberly Clark, people that I met on Upwork through that platform because they have those kinds of relationships over there.

It’s really important just because Upwork gives me those extra tools like the time logging, they give me the automatic invoicing, you know, I never have to worry about what did the client do? I got tracked on the invoice. They essentially do automatic contracts because your proposal essentially serves as a contract. And of course the most commonly known thing they offer is the marketplace. Right? So it’s not like I’m not getting anything set at 5% either. In fact, I still freelance outside of the site as well. Like on this side, my clients are about 50, 50 Upwork and 50 50 offsite. And honestly it kind of, I almost try to push more clients to Upwork, even if I don’t meet them there because I find it’s just easier to use Upwork’s tools than it is to use the other tools I have to manage with my other clients to track invoicing and contracts. I just think that you get a lot of value for Upwork for that, but the long-term client relationships, it does reduce the fee, which is yet another benefit of doing that. So that’s my third biggest tip.

KEISHA BLAIR: That’s amazing. And so I was just going to ask you something that you just said, which was, is Upwork your kind of like main go-to for clients and you just mentioned it’s 50-50. Are there other platforms and where do you get your other freelance work from? And the other question is, because you also mentioned that you’re at 500K on Upwork, which is around about 50% you mentioned of your client work. So, in terms of your total income from freelancing, is it way over that now with everything combined? Now, I’m eager to know about, you know,

MORGAN OVERHOLT: At this point I’ve gotten my hands in so many different buckets that almost have to ask my accountant what my total worth there might near my net earnings event. I now run several different little things, including a couple of blogs. And as you said, coaching that I’ve just now gotten into coaching, so my income has diversified and I always like to put a lot of my freelance income back into my blogs and back into some of the other products that produce that passive income. But I would say roughly from freelancing before I put money back into the business, or back into any of my other pursuits, I would say I get close to the $200,000 mark from just the freelancing for a year with major expenses taken out. The easier number I know that my top line is $300,000 a year, right below 300,000.

KEISHA BLAIR: That’s interesting. And I’m sure this is motivational for so many people listening to think that there’s hope like you can monetize your skills. You can make it out there. You just need the right tools and the right way of doing things. So Morgan, are there any other platforms that you’re on that you work with that you would encourage people to also check out too? Or any other sites, anything like that?

MORGAN OVERHOLT: So to be honest with you, when I first quit my job, I felt a little terrified because as I mentioned earlier, the whole rage quit thing, not really part of the plan. So I had like what I call a baby safety net. I kind of halfway prepared, but not all the way, especially if my husband’s still doing part-time contracting at the time. We know, not even giving their husband a chance to go find more work first. Honestly, I was so terrified. I quit my job.

I tried every thing and I think that’s a really good tip for freelancers. Right. You know, so often I see people say, Oh, well, I don’t want to give me all the tips that don’t include X, Y, and Z, or tell me what to do, but I don’t want to do Upwork. Right. I don’t want to do Fiverr. I don’t want to do any of this other stuff, right.

And I think it’s honestly the wrong mentality because you don’t know if it’s going to be Upwork or if it’s fiverr or if it’s offsite, you don’t know what it is. It’s going to click for you. And in the beginning, if you are in a struggle for that money or worrying about where that money’s going to come from, like I was, I mean, I was in a bit of a panic mode is because of the way that I did things a little bit unplanned, not completely planned, at least we’ll have, we’ll call it half date. Shall we we’ll call it half. That’s what it was, you know, I wasn’t going to be picky or snobby. I was going to try to enter into it with humility. I think that that’s a really important word and to see if I could get anything to stick, I did try almost every platform. I tried networking in person at conferences. I immediately emailed every single client I had worked with in the past, like five or six years. And I told them, Hey, I’m making this switch to full time. Do you have any referrals for me? Or, Hey, do you have, when you work for me just to let you know, I’m I I’m available. You know, I did that kind of stuff for me personally, the two things that really panned out were just the referrals and Upwork, but that’s not to say that other platforms won’t bring you success.

I really think you should cast a wide net. And then concentrate on what’s providing that ROI and the referrals, as I said earlier. So very important that you do that both with your current clients or your offsite clients and your Upwork clients. People often don’t think about asking referrals from their Upwork clients, but they often have great referrals as well.

So that’s a really powerful Freeman’s tool right there. So to answer your question still today, I mostly work off of referrals and I work off of Upwork. But that’s not to dog, any other freelancing platform. I think they all have potential. And honestly, I don’t think you should count anything out if you’re really trying to make something work.

KEISHA BLAIR: For sure. I’m sure people are listening in and they’re thinking, well, how do I get this recurring monthly revenue that I can count on? You know, revenue that’s stable. And it’s not like a big, huge drop from month to month, you know, it’s kind of stable. I can count on this amount coming in. And so do you think that’s kind of like the bread and butter of making sure you have stable reoccurring revenue from freelancing because you might get something here and there. But then how do you make it to be like, okay, this is reoccurring and you don’t have to sweat it, you’ll get this coming in and, you’ll be able to pay the bills.

MORGAN OVERHOLT: Yeah. In the beginning that is the problem. Right. Because in the beginning, it’s really scary. And in fact, I would say that I wasn’t able to truly stabilize my income until about three months then, you know, it was, it was up and down and I had moments where I thought I was going to be, you know, swimming in my vault of gold coins. And then there are other months when I thought, Hey, why don’t we put some more ramen in the cart this week? You know, it completely varied. But after the three-month mark, because largely because I focused on those referrals and I focused on long-term clients.

It all became very stable. I mean, today, I don’t think I’ve had it a month where I brought in below $20,000 in, rather than you nearly two and a half years now, just top line revenue from freelancing. And you’d be shocked because today I don’t even apply for jobs anymore, but they 100% come to me. And when you get into that stage of freelancing, it’s, it’s incredible because it becomes less about worrying about that daily struggle or you know, Oh my God, do I have enough money. Am I going to land enough clients, you know, am I taking on this client that’s not going to treat me well, or I’m not going to be able to do this job. You know, all those stressors go away and it almost kind of becomes like you’re on autopilot. You know, the clients that you’re working with every day are these tried and trusted professionals that even become your friends over time, you get used to a certain amount of workload. You know, you can always add on if you want to save up for something or you can always scale back a little bit, if you want to take a trip or take some time off. And, but that’s the great thing because after a couple of years, I really got to the point where I didn’t need to apply for anything anymore.

And that’s the point where I am now, honestly. Today. I, it’s almost harder for me to get some dang time off. Like I have to tap the brakes a little bit, you know? Yeah. So that’s amazing. Yeah, no for sure. Good problem. And so on Upwork does that, most of that just come then, is it just like past clients are like, Oh, I want this done and you don’t have to apply.

And so on Upwork, all of that just comes in. Yeah. So a lot of it will be past clients. I also get a lot of client referrals, even the ones I don’t ask for sometimes on Upwork. Now people talk, you know, he views, it varies. And the greatest degree in thinking about up workers, a lot of them have worked for each other or hired other people or work with the other companies.

It’s kind of its own little, you know, network group. But what’s also really cool to Upwork is they have this whole invite feature and the more successful you are in the platform, the more often the Upwork algorithm will suggest you. So like let’s say right now, and what’s even funnier. I actually keep my profile turned off half the time because lately I’ve been trying to bank time off so I can actually go on a vacation.

So yeah. I actually have it off right now just to like stop the invites. That’s how frequently I get invited. I have to turn my profile off temporarily and it’s not gone when I’m ready to receive again. It’s crazy when you kind of get to the point where you a lot of money and Upwork and you know, you’re using all those right keywords and you’re in your bio and you’ve got a great tagline.

That’s very attractive and you’ve got a lot of successful jobs that you’ve done. Have a great job success score. The Upwork algorithm. If it comes, somebody looks for graphic designer pretty much usually on the first or second page, if not pretty much at the top. Right. So we will look on for a graphic designer to go on Upwork and they look for a graphic designer.

It says, Hey, do you want to invite people to the job? And they’ll say, yeah, sure. And they kind of click on the people that Upwork recommends to them. Which usually I’m included to that and they invite me directly to the job. And from there I just go in and they say, yeah, I’m interested or no, I’m not interested. And I apply that way. And that I would say started happening with a fair amount of frequency, about six months to a year in that I was getting a pretty consistent amount of invites being sent to my Upwork inbox. So that’s really helpful too.

KEISHA BLAIR: That is for sure. And as you’re speaking, I’m just thinking about my next question, which this kind of segues really good into that because as you know, I developed this personal financial identities framework with a free quiz to help people identify their own personal financial identity, and I’m dying to hear your results because I can guess I can almost pinpoint based on this whole conversation, what your personal financial identity is, and I’m sure as soon as you announce it, everybody’s going to be like, ah, we can see that. So, any thoughts you have to share on that too, in terms of your family background and you know, how you were raised, Because I find that at this point in the podcast, It’s so amazing, the insights that people have shared and so others can learn from their experience and how they’ve harnessed the strengths of their personal financial identity. So, Morgan, can you share that with us, your quiz results and your thoughts?

MORGAN OVERHOLT:  I’m a Risk-Taker. But what’s interesting is I’m a Risk-Taker that was raised by Minimalists. All right. This is not normal for my family. And it’s like, I’m pretty sure that maybe if my dad listens to this podcast, he just figured out that I have a real job. Like, I mean, I think it still perplexes him what I do. He’s like, wait a minute. She is making money.

KEISHA BLAIR: That’s amazing. To hear you were raised by Minimalists. I want to hear more about it. I’m sure everybody’s like, I want to hear more.

MORGAN OVERHOLT: My parents are extremely traditional, you know, we were just kind of raised in a low to medium income household. My dad worked, my mom mostly stayed at home until we were a little bit older and then she became a Secretary at the local community college, you know?

And I was so privileged and fortunate for those things, you know, but, we shopped at the consignment stores. There were no fancy clothes. There were no fancy vacations or anything like that. It was all very simple. Or if you did want something fancy, you better be saving up for that four months because it’s definitely not going to be a given.

And so it’s kind of funny because my entire career, like I said, when we started this, you know, my parents were very much like they didn’t even understand why I was  spending all my time on the computer. My dad was convinced until I was about 21, 22 years old, that I was going to be a speech pathologist because that’s what he wanted me to be.

He said that that’s what he determined to be a steady and stable career. Morgan, you know, not this computer thing that you want to do. We want stable, you know, my dad, my dad has had the same job for 30 years now. My mom, you know, she recently retired recently but she retired as a secretary at another local community college.

I mean, they pretty much lived a very traditional American life where same job, you know, so for me, I mean, it was hilarious because when I quit my job, my parents were just like, especially my dad, he’d be like, so you’re applying for jobs this week, right? Like, no dad, I’m freelancing now. He’s just like, so until you get a job, right. So when are you going to real money?

KEISHA BLAIR: So funny and I’m sure many of us in our generation can identify with that. It’s just all about the real job. And then you work until you get the pension, right? And so the pension is the Holy grail.  

MORGAN OVERHOLT: even funnier is my mom, now that she’s recent retired, I’m kind of like pushing her a little bit out of her comfort zone after more or less working, a very similar job for so long. Now she assists me on my blog. We also run a travel blog called you know, quick plug, but I’ve taught her how to use WordPress and do all this stuff. So she’s now freelancing for me in her retirement.

KEISHA BLAIR: Wow. That’s amazing.

MORGAN OVERHOLT: Now we’re seeing her outside of her box, you know, she’s been her whole life, like, you know, kind of doing the same thing over and over and now she’s like, what the heck of it? Yeah. So. I’m kind of forcing her out a little bit, but yeah, it’s really interesting. I don’t know if this is your next question, but how did I become a Risk-Taker that was raised by a Minimalist? I have no idea.

KEISHA BLAIR: It’s so funny because I think most of us in our generation kind of saw our parents work and toil probably had no work-life balance. And, you know, with the same employer just retired, barely able to make ends meet. And we thought, I don’t want that lifestyle. I don’t want to have this job for like forever and everything is just this goal to have a pension. And still, when you get the pension, it’s not enough. It barely make ends meet. And so. I think for a lot of us that was never kind of, a goal. And if we want it should a different life.

I know that for me, after my husband died, I was widowed so young. And so I thought, no way, am I going to, to like live in this box where if I want to take time off, you know, because I had to take time off when he died and I had to forego the salary and if it wasn’t for investments and things like that, I wouldn’t have been able to do that. So even if you have a job, let’s say, and even if you are comfortable with your career and you’re happy, that’s great. But for me, it’s always been okay, well, how can I still have passive income streams so that if anything were to happen again, and God forbid something happened, I could, you know, I can live and take the time that I need to recover or to do whatever I wanted to do.

So that’s kind of, I think, where a lot of us are coming from, and that kind of divergence and thought. And so, you know, you explained in terms of taking risks from the very beginning, I mean, even the confidence that you had to quit your job, many women probably wouldn’t even have that confidence. And I mean, you had some freelance contracts and that was great. And so are there other areas where you’ve taken considerable risks that you can share with us, or is that like, kind of like the major one?

MORGAN OVERHOLT: Yes. Well, that’s the funny thing about us risk-takers and I do want to say like, with this, that I’m a risk taker when it comes to business, I’m still not one of these people is going to go to Vegas and put a hundred dollars on the table Right. It’s my hard earned a hundred dollars and I’m still a person that shops the clearance racks, you know, I am that person. So I am specifically a risk taker with business, but here’s the funny thing about that. I kind of feel like it’s very addictive. It should come with a warning. In fact, I think I’ve gotten worse the longer that I go, because after I found success with the freelancing, I thought, okay, well, what else could I do, right?

I mean, why, if this worked, I’m sure I could get something else to work. So it’s kind of funny when 2020 hit and we were all, you know, in the midst of the shutdowns. I had a couple of weeks that we were just a little bit slower than usual. We were very, very once again, privileged and lucky and blessed to be able to have, you know, a steady amount of work during that time.

But there was a couple of weeks, a little bit slower than it normally was. And I got the harebrained idea because I always wanted to try blogging. To start blogging. And I asked my sister and my husband, if they’d be interested in doing it with me, you know, to have partners this time. So in just a couple of weeks, we launched a site called, which is just a regional travel website that caters to East Tennessee and the great smoky mountains, national park and the attractions around it.

And it’s amazing because looking back, I had no idea what I was getting into fast forward now just at a year later. I think we’ve had 1.5 million hits on that website 0.5 million and blogging at the time. And we all had to kind of learn on the fly, you know, and that was definitely a risk at the time, because any blogger will tell you, and yes, any content creator will tell you that there’s a lot of grind before you ever even see one penny.

I remember the first day that site brought in $6. I was like, Oh my gosh, jumping up and down. I was like calling my sister and I’m like six bucks. You know, we framed that $6. You know, it’s a big deal. But the great thing is once you’re a business owner, you know, the risks almost become a bit more nominal as one business can kind of fund the next business and you can.

You can try things and see whether or not they work or not. You know, you develop multiple streams of income. So inherently everything becomes less risky. In fact, that’s one of the reasons I think I did so well, you know, during the shutdowns, because my freelance client base in itself is very diverse. I could ever think from, you know, uh, I’ve done nuclear diagrams for the NRC to kitty litter illustrations, you know, so, I mean, I have a wide range of work and I try to set my business up that way. And so I think as Risk-Takers, we not only get a little bit more used to taking risks as time goes on, but they also become inherently less risky as one thing supports the other and diverse.

KEISHA BLAIR: Great words of wisdom to end on Morgan. I really enjoyed this and this was so good in terms of tips and strategies. So Morgan, where can people find you like on social media and your website?

MORGAN OVERHOLT: Yes, absolutely. In fact, as I just relaunched my website, in fact, actually, Keisha, you didn’t even know this, but this podcast is what I’m using to announce my coaching services. I literally just launched that last week. So guys make sure to go to

It’s You can also find me on Twitter. It’s And I would love to connect with you there.

KEISHA BLAIR: Okay, perfect. So once again, Morgan, thank you for sharing your story and those great tips and strategies with us. It was amazing having you here.

MORGAN OVERHOT: Thank you. It was such an honor to be here, Keisha. Thank you.

Thank you for joining us this week on Holistic Wealth with Keisha Blair. Make sure to visit our website where you can subscribe to the show on iTunes, Spotify or via Rs so you will never miss a show. While you’re at it, if you found value in this show, we’d appreciate a rating on iTunes or if you simply tell a friend about the show that would help us out too. Are you a member of the Institute on Holistic Wealth? If not, what are you waiting for? Go to Institute on Holistic Wealth/memberships to choose your membership plan and join as a member. You get so many perks, free worksheets, advice coaching, and a member’s workshop to design an intentionally designed life. Do you need to figure out your life purpose? Take the Build Your Life Purpose Portfolio online self-paced course. Are you struggling with all your money decisions? Take the free financial identities quiz and then take the personal financial identities course. Did you recently suffer a breakup job loss or experience the death of a loved one? Take the Holistic Healing online course. Do you need an overall plan to achieve holistic wealth? We will help you figure out your Holistic Wealth Blueprint and of course if you want to start making money by helping others achieve holistic wealth, become a Certified Holistic Wealth Consultant. Regardless of what career you’ve got, the Institute will show you how to increase your income and walk in your purpose. The sooner you join the sooner you start to achieve a more holistically wealthy lifestyle and you’re going to want to stay for a very long time so go to Institute on Holistic Wealth/memberships to join. If you haven’t read the book yet pick up a copy of the award-winning best-selling book Holistic Wealth: 32 life lessons to help you find purpose prosperity and happiness