How to Start Freelancing with Jay Clouse

EP 13 Jay Clouse: Freelancing for Teachers


From copywriting, editing, and virtual assisting to instructional designing, project managing, and educational consulting, there are many great freelancing opportunities for both current and former teachers. While you have control and flexibility of your own schedule, one of the biggest challenges for those interested in freelancing is figuring out how to get started. That’s why I’m excited to have Jay Clouse as the special guest for this episode of the Teacher Career Coach podcast. With over 10 years of experience in the entrepreneur space, Jay has created an entire school to help freelancers succeed and scale their businesses. Follow along as he shares his knowledge and insight, offering advice for teachers looking to get started in the world of freelance work. 

Recap and BIG Ideas:

  • Freelancing is a great opportunity for teachers looking to transition or build resume experience and earn extra income while still in the classroom
  • Starting freelancing while in the classrooms gives you valuable insight into your likes and dislikes. It also helps you make career decisions without being controlled by financial fears
  • While teachers often underestimate their skillsets, there are plenty of freelancing opportunities that match their teaching experience, skills, and other interests. 
  • Many skills inherent to teaching, like writing, communication, breaking down concepts, and persuasion, are currently in demand for a variety of businesses and industries. 
  • When applying for freelance opportunities, especially without much experience, it’s beneficial to provide a work sample and just go the extra mile to show you are the right person to hire. 
  • There are plenty of sites where you can build your freelancing resume, but it’s always about building strong relationships with clients. 

Listen to the episode in the podcast player below, or find it on Apple Podcast or Spotify.

What Does It Mean To Be A Freelancer? 

Daphne: Hey, Jay! Thank you so much for joining us here today.

Jay: Daphne, I’m super, super excited to be here. Thank you for having me. I think this is going to be a lot of fun.

Daphne: I wanted to start off with just a little bit about who you are and what you do.

Jay. My name is Jay, as you probably heard already, dear listener. I am an online creator. So, I spent a lot of time writing. I spent a lot of time podcasting. I’ve also spent the last four years freelancing and sustaining myself through freelance work. 

After doing that for four years, I found that there’s a lot of opportunities for other people to make a living freelancing. So, I built Freelancing School as an educational platform to help people get to the point where they can make a living freelancing themselves.

Daphne: So with my audience, I know a lot of people have asked me questions about freelancing because I actually talk about how I freelance as an educational consultant on the side. 

So, what is a freelancer? What’s the textbook definition of a freelancer?

Jay: Freelancing basically just means that you don’t have a full-time employer. You’re not working a W-2 position where you’re getting a paycheck or consistent benefits. Instead, you are working as a 1099 independent contractor. 

Outside of that definition, freelancing can apply to a ton of different disciplines. It basically just means that people are paying you for your skills and the outcomes that you are promising to them for the scope of a project. That scope may be consistent, hourly work every week. It may be a very specific project that has a very well-defined beginning and end date and a specific set of deliverables.

You can really structure your freelance work in a lot of ways depending on the discipline that you are freelancing in. Basically, it just means that you are your own employer and own boss, and you are not getting a W-2 income.

How to Start Freelancing with Jay Clouse

Freelancing And Benefits. 

Daphne: It sounds like there are a couple of risks associated with freelancing, particularly figuring out your own benefits if freelancing is your full-time job. What benefits do you see with the life of a freelancer that outweigh the cons of having to pay your own benefits? 

Jay: Most people are drawn to freelancing because you have so much agency over your time. You choose the work that you do. You choose when you work. You choose who you work with. You choose where you work from. Your whole life is really in your control. The constraint is you need to earn enough to reach your earning and saving goals. So, that’s the main trade-off.

But there is just so much opportunity because you don’t have a cap on how much you can earn. With any W-2 position, there is naturally going to be a ceiling on how much you can earn in that position. The nature of that kind of full-time work is the organization or business owner is paying you less than they are receiving for the value of your work. They can’t pay you more than the value of the work that they are receiving. So, there’s always going to be a ceiling on how much someone is willing to pay you as an employee.

When you work for yourself, yes, there are some risks involved, but you also remove that ceiling. You can earn as much as you want and can. You can build a pipeline of clients and business. So there’s huge, huge potential if you choose to go down that path.

Getting Started Freelancing While You’re Still In The Classroom. 

Daphne: So if a teacher wanted to start freelancing, they would have the ability to actually freelance part-time because they’re creating their own hours. They’re taking the jobs that they’re able to do when they’re not in the classroom, correct?

Jay: Yeah, absolutely. I think that’s a really great place to start. In fact, a lot of people get started with freelancing that way. Think about any gig economy type employee—anyone who’s driving Uber or Lyft, or doing Postmates on the side, or anything where you’re just kind of going through this application and being paid on a per gig basis—that’s the same nature of work as freelancing. A lot of people do that on the side because it’s a way to earn extra income. 

I think if you’re just getting started, it actually makes a lot of sense to start freelancing on the side. You’re going to get a really great sense of whether or not you enjoy it, which is important if you’re thinking about doing it full-time. It also takes some time to build up the skills, competencies, and confidence to freelance full-time. It takes you a little bit to build up enough conversations and potential clients in your pipeline who may want to hire you for some sort of work. 

There’s a lot that goes into it upfront. So, if you can start freelancing before you need to depend on it for your sole income, you’re going to be much better off long term.

Daphne: Yeah, that’s a really great point. I’ve talked to people before about starting their own business—even just something as small as selling digital curriculum online—and the reason why is because you don’t know what you like until you actually try it. 

For me, I looked at all these skills that I would need to sell digital curriculum online. When it came to blogging, search engine optimization, and social media management, I thought I was really going to enjoy blogging. I found out quickly that I don’t like blogging as much as I like search engine optimization. Until you start implementing and start playing around with these skills, you’re not going to know what you actually enjoy. 

Freelancing Helps You Build Resume Experience While Getting Paid. 

For people who are thinking of using freelancing as a resume writing experience, you’re going to want to know what you actually enjoy doing before you put all your eggs in that basket. So, this is the perfect opportunity to build those skill sets, while you’re actually getting financially compensated for it.

Jay: Can I talk about that a little bit more, because I think this is a really, really important point. If you’re listening to this and you’re considering freelancing, or you’re considering a transition of any kind, you’re in the perfect position to be very thoughtful about designing your life. The constraint for people leaving a full-time job is replacing their full-time income. 

If you jump without a parachute or without a plan, or you haven’t tried these things out, you are not going to be able to avoid making decisions based on money. Those decisions won’t necessarily be the same decisions you would make if you’re trying to optimize for lifestyle, fulfillment, happiness, things like that. So, if you’re in this position where you’re thinking about a transition, but you are still full-time employed, this is the perfect time to be trying things. 

You can get a sense of what you do and don’t enjoy. Usually, people enjoy two-thirds of something but hate the other third.  That’s a great insight. Consider what you can do to maximize the time spent on those two things, and erase the other thing. It might be a slightly different freelance path. It might be hiring somebody to do the third part, which is totally okay. 

You want to have these insights before you are so dependent on the income coming from this thing that you may not love before you don’t have a way out. When you’re in this position of potential transition, but still earning a paycheck, it’s the perfect time to be discovering these things.

Daphne: Yeah, absolutely. A lot of people feel like they’re at a certain point on the salary schedule, there’s no way that an entry-level position will hire them for anything near their current salary. 

My advice for those teachers is first to show you have years of experience and how your experience translates into the experience that they need so that it’s not entry-level experience. 

Second, start diversifying your income. If you feel like your income is holding you back from achieving or reaching for a different path, then start diversifying. Figure out what you can put in place to start supplementing your income so that somewhere down the line you have the ability to make that decision with confidence. 

Jay: Yeah. I 100 percent agree.

Getting Started As A Freelancer. (No Additional Schooling Needed.)

Daphne: Another thing many of the teachers that I’ve talked to about freelancing ask is if they need to go back to school to learn some of these skill sets. 

Jay: Nope, you don’t need anything other than the ability to convince somebody that you can do the job. Technically, you don’t even need a portfolio. You need to be able to convince the person who’s hiring that you can get the job done. That’s all you need. 

Now, most freelancers will find that they are more confident and more able to convince people that they can do the job if they have things like a portfolio of past work, past clients, or a website that shows that they do this kind of work. There’s a lot of validity to that because if I’m thinking about hiring somebody, I want to know that this person can deliver on what they’re saying. The best way to know that as someone looking to hire is to look at past experience, client testimonials, and things like that. 

Do you technically need anything? No. Do some of these things help? Yes. But you don’t need any type of degree for freelancing. People care much more that you can exhibit the skills and the outcomes that they’re hiring for. They don’t necessarily need any type of certification or degree to believe that

Daphne: When you’re talking about the different skills, do you have specific skills that you recommend people look into first? What about those who have no idea what they even want to do as a freelancer? 

Jay: Well, there are a couple of ways you can approach this. There’s skill development and then there’s just packaging and showcasing your existing skills and leaning into those. I 100 percent recommend starting with what you know you can do. People often radically underestimate their own skills and the value they bring to the table. 

Think about any job that you’ve worked. That is something that someone might want to hire you for on an independent basis. Tutoring has been around for a long time, right? In a way, that is essentially freelancing as a teacher. Think about the other skills that are inherently part of teaching. As a teacher, you’re probably public speaking every day. Those communication skills, soft skills, persuasion skills, and teaching skills are actually very, very rare. 

In today’s gig economy marketplace, there are a lot of people who can help you create a banner for Facebook using Canva or something. There are a lot of graphic designers who can do that. There are much fewer people who can do some of these nuances that come with communication, writing, proofreading, and things like that. These things that used to be much more common are actually becoming more and more scarce. 

I think teachers are in a fantastic place to lean into their existing skills of writing, communication, teaching, persuasion, proofreading, and such. That is all in demand right now for a variety of different businesses and industries. 

Freelancing Opportunities For Teachers. 

Daphne: Yeah, I wanted to add to that a little bit. When I’ve talked to different teachers who have been freelancing, there are career writers, copywriters, virtual assistants online, and project managers, right? One of the most common things that teachers can actually start to look into or explore if you love pedagogy or are still really passionate about education is something called educational consulting. 

Consulting is just a very vague term. Educational consulting can mean you’re freelancing and working with educational companies to answer their questions like, what gripes do teachers have? How can they better their curriculum to help teachers succeed or be more interested in that specific product? There’s also educational consulting where you create your own professional development and sell that to districts. You go and present professional development for teachers and districts.

Jay: I love that. Generally speaking, curriculum development can be really, really powerful. You can go into a business or an organization that has a really good way of doing something like they’ve been operating for years and have a really great process for X. It’s getting more and more common that organizations want to produce their information and their skills, and turn them into an online curriculum. 

It might be an online course that they’re putting on a platform like Udemy, or maybe they’re trying to do some live cohort training. Somebody who’s developed curriculum can come in, ask questions, start to pull out and codify the way that these organizations work, and help create curriculum for them.

Innate in that activity is facilitation. As a teacher, you’ve likely facilitated a ton of group discussions. That can be really, really valuable for other organizations who need to bring in an outside facilitator to help them have productive meetings or productive planning sessions, things like that.

Freelancing To Full-Time: The Valuable Skills You Learn Along The Way. 

Daphne: Have you seen a lot of freelancers actually use their experience freelancing to leverage themselves into full-time positions?

Jay: When people get into freelancing, they usually have one of three directions that they’re working towards. The first direction is they eventually want to build a larger business than themselves. It’s kind of the agency model. It’s hiring people. It’s working with bigger clients. It’s doing bigger projects. It’s building a business out of your freelance business of one.

Another path is using freelancing as the economic engine to let them explore some other interests. That might be building a new economic engine, like building online courses or a podcast that generates income. A lot of people get into freelancing to preserve the time and space to build some other thing that is more passive. 

As far as income goes, other people on that same path are using freelancing to build an economic engine so they can just spend more time with their family. They have an hourly rate and a consistent amount of inbound leads helping them meet their earning goals. Then, the rest of their time is just gravy and can do with it whatever they please.

The third pass is kind of an exploratory phase. They want to make a transition and think they can earn money on their own using these skills. They’ll figure out what comes next when they figure it out. 

Most people who enter into freelancing recognize that they’re going one of those three paths because it’s kind of a transient thing. Nobody freelances forever. So, to answer your question, people in that third path where they figure it out later, often do leverage that into a new full-time role. 

Most employers want to hire somebody who exhibits experience more than somebody who just has a degree. Freelancing is the ultimate way to get experience, and not only experience with a certain skill set. You learn all these other incredibly valuable skill sets when freelancing, like managing many different projects, communication, financial literacy, and sales.

When you freelance, you have to learn how to sell yourself. That is such a valuable skill set for any organization. So, people will look at your freelancing resume and your freelancing experience and see all the ways that your capabilities plug into their organization. It can often be in a generalized role, where they know they have these three needs. They have a budget for one person and kind of need a superhero. 

Honestly, I think teachers are well equipped to do that anyway, but especially those who have freelanced because they’ve worn all those hats for their own business.

Daphne: Yeah, absolutely.  

Tips For Transitioning From Teaching To Other Roles. 

You’ve mentioned before that you have a couple of educators in your family as well, right?

Jay: So many. I had both of my parents as my teachers in high school. My oldest sister is a teacher and her husband is as well. They all taught at the same high school. So it’s definitely in the Clouse blood.

Daphne: You mentioned to me that you were having a really good conversation with your family members who are teachers. You were talking about how teachers can actually transition into roles without having specific experience. Can you go into that a little bit more?

Jay: I’ve seen my parents, my sister, her husband, and even my cousins and aunts go through hitting this point of burnout, like many other teachers. As the years have passed, there are more and more expectations as far as what teachers need to do with their very finite amount of time. It’s rarely expectations in the classroom and instruction. It all seems to be outside of it. I can see how it could really, really burn you out. 

The story that I’ve heard from people around me who hit that point, is that they have this limiting belief that their certification and degree is in teaching. They don’t know what they’re supposed to do with that and believe they can’t get another job with that. That’s so not true and is so limiting. Like I said earlier, so many companies would rather hire somebody with working experience than somebody who has a degree–unless it’s an entry-level position where they’re literally setting them up for recent college graduates. 

The real world is just so much different than school and businesses understand that they have to move quickly. They have to move at the pace of business. They want to hire people who are skilled, who have experience in the real world and have the skills of communication. They want someone who can problem solve and can figure things out. These sound like such basic things. 

I hope you’re listening to this and saying, “That sounds so basic. I can do that. I can problem solve. I can communicate. I can lead teams. I can do public speaking. I can do all these things.” And that’s why you’re in such a good position to actually get some of these roles that are out there. Especially younger companies who don’t have such a fleshed-out organizational structure where they have these really, really rigid expectations of what person fits into a role, right? 

Startup companies or younger companies, small businesses, they just want to hire exceptional people. If you look at their job descriptions and it seems interesting to you, but you feel like you don’t match the requirements, please apply anyway. Then take the next step of figuring out a way to stand out in application because most of the time, when you’re applying through the front door of a website, it’s just not your best chance. People on the back end want to have the right hire and to know they’re making the right choice as soon as possible. 

Unfortunately, it’s so hard to parse through all these applications and resumes. So, if you can make an impression and find the person who’s actually hiring and have a face to face conversation or voice to voice conversation with them, they’re going to be so much more confident that you are the right choice for this job than any piece of paper out there. 

It may be hard to get that first conversation. So, with your application, maybe add a line where it’s like, “Hey, I also recorded a three-minute video talking about this position and why, even though my experience may not map directly to this, I think I’m a really, really great fit.” That is going to create such an impression. It’s going to stand out. They’re going to watch it and have such a better understanding of who you are, how you communicate, how they might interact with you if they hired you.

People want to know that the people they’re hiring are people they want to work with. You can’t get that from a piece of paper. You need to have an interaction. That’s why interviews exist. But, if you can create that impression before you even get to the interview stage, you have such an opportunity to branch out into a new industry, a new organization, or a new company, because you have these skills that are innate from being a teacher.

Marketing Yourself as a Freelancer. 

Daphne: Yeah, and it’s not just with applying for full-time positions. That’s a really great strategy for marketing yourself as you’re reaching out to potential clients as a freelancer. If I’m trying to hire someone, let’s say to create my Pinterest pins for me, someone might say they’ve been making Pinterest pins for a year. However, another person might go out of their way and make a couple of Teacher Career Coach Pinterest pins. I’m automatically able to see they took the extra step. I can already see them in this role because they took the extra 15 minutes to go above and beyond for that application.

Jay: Totally. I was listening to a comedy podcast where they were talking to an actress and his role had reversed and that he was producing a show. I know it seems like a weird setup, but follow me. He now had to do the casting for this show.  Prior to that, he had always been the person auditioning for roles. He said he realized that as the casting director for the show, you want everyone who walks in the door to be the answer. You want them to be the person that you hire, but they need to make it abundantly clear that they are the answer.

So, whether it’s a full or part-time position, if you go into job interviews or being considered for some sort of position or work, they want you to be the answer. They are rooting for you. All you need to do is confirm that they’re making a good choice.

Daphne: So, somebody who’s going in and applying even for a freelancing position or they know someone needs a copywriter, it would be really impactful if they took that extra step to actually write copy that looked like what their potential client would be looking for. Would that be advice that you would give?

Jay: 100% because we have infinite amounts of choice for anything in our lives. With that comes this underlying fear of making the wrong choice and failure. So, we don’t make choices until we have to. Most of the time, we need a deadline. We need a hard reason to make a choice.

All this to say, the more that you can do in the process to ensure this person that you are not going to regret that you are somebody who will get the job done that they’re making the right choice and hiring you, the better off you’re going to be. If that means showcasing the work that they’re looking for before they even hire you, that’s a pretty great sign. 

In the process of communicating with this person and interviewing for a position or a gig, you need to be the leader in that process. People respond well when it feels like you’ve been there before. You know what they’re trying to do or the outcome they’re striving for. You understand their problems, the outcomes they want, and the constraints they have. They want to feel like you’re giving them the next steps of where to go.

If you can literally transition in the interview the role from applicant to a leader, it helps eliminate their fear of making the wrong choice. That is obviously a problem that’s top of mind for them because they’re looking to hire for it. 

I can even give you a sample of how that conversation could or should play out if you want.

Tips for Approaching Freelance Clients

Daphne: Yeah. I’d also like to know, where are they even going to find these clients?

Jay: Let me go first with his direction of talking to the potential client, then I’ll talk about where we find them. 

When you’re talking to somebody who’s considering hiring you, they’re going to give you a bunch of details. You can literally start the conversation with, “Okay, so tell me about your project,” or “Tell me about your business,” or “Tell me about X.” They’re going to throw a lot of information at you. 

So, your first step, the first thing that you can do that’s really impactful is to make mental notes of the important points. What is the reason that you’re here? What is the outcome that they want? What is the pain that they’re feeling? Then, at some point, you say, “Okay, let me repeat this back to you. It sounds like you really want to have a higher conversion on your website,” or, “It sounds like you really want to have higher open rates on your emails,” or, “It sounds like you really want to grow your Twitter following.”

Then you pause and look at them. They’ll probably nod and you can say, “Okay, great. Super doable. I’ve done this before. I feel really confident that we can get to that point. Here’s what we need to go from here, A, B, and C.”

And then you ask them, “What is your timeline for this? When ideally, do you want this outcome? When ideally, do you want to have this many followers on your Twitter one? Ideally, when do you want to have this new about page for your website written?” They will declare a timeline and a deadline for this project. 

That’s when you can say, “Well, to get this outcome by this date, we need to get started on this date.” Then it’s, “So I’m going to crunch the numbers and will send you a proposal to let you know what this looks like moving forward. But, again, if you want to get it done by this date, we need to move by this date.” That creates the decision point I was talking about. It creates that little bit of urgency and that deadline to make somebody make a decision. 

It’s also showing them you know the outcome they want and their constraints, and you also know this process so well that you know when you need to get started to meet those constraints and meet that deadline. That shows so much leadership and so much confidence. They’ll likely think, “Wow, I need to get moving. This person really seems to get it.”

Daphne: Yeah. And being on the other end of that, sometimes I’m hiring freelancers and I don’t even really know what I want. I think I know what the objective is. For example, I’m hiring someone to do my blog writing, and then when they come in, they show that they have all of these ideas, and they take charge. It’s a relief to me and I think, “Oh, good. They’re going to do that work.” I don’t have to think about it anymore because I can tell that they’re a self-starter and that they have this all under control. 

Jay: There’s a lot that can be accomplished by asking insightful questions to gain fidelity in that person’s mind. Again, you’re leading that person. But the other reason you ask about their timeline is a lot of freelancers will tell you, “I had this conversation and it went really well. I followed the proposal and I never heard from this person.” That’s really hard and it’s because this person is afraid of making the wrong choice. You didn’t make an impression that you are obviously the right choice. 

But, if you ask for a self-reported deadline, that gives you a perfect reason to follow up after a few days. You can say, “Hey, I want to check in on this proposal.” Or, “I wanted to check in on this project. I know that you were trying to have this done by this date. And for us to do that we really need to get moving by this date. So, I wanted to touch base.” That doesn’t feel pushy. It’s not, “Hey, are you still doing this thing?” It’s reiterating that you know their constraints and want to check-in so that they can still meet that constraint. It feels as if you’re just being very professional and very thorough, as opposed to needy or pushy. 

Tips For Finding Freelance Clients. 

Daphne: Absolutely. Let’s go back to the situation where a teacher has decided they want to be a copywriter. They don’t have a portfolio written. So, where are they going to even start attempting to find clients? Where do they start looking for those clients?

Jay: There are three pathways to consider here. I wouldn’t say only do one and not the other two. Actually, you can kind of have a portfolio approach to all three of these things. 

So, the first one is direct a client. This is what I believe has the most long-term potential if you’re trying to build a sustainable business. It’s the most traditional method. It involves talking with a person about their project. Then you scope it out and tell them how much it’s going to be. You do the work, communicate with them on the work, and then they pay you for the work when the project is done. It’s pretty straightforward.

However, it’s also the hardest to get rolling in the beginning because if you don’t have a portfolio, if you don’t have a reputation as a freelancer, why should this person trust you? You have to go one client at a time, have an excellent experience, wrap that into a case study, put that into your portfolio, then start to show some history and some outcomes. 

The second path is what I call sub-contracting. Basically, instead of working directly with a client, you are working with somebody else who is working directly with a client. That agency may be a website development agency, if you’re a copywriter, and they sell a full website project to one of their clients. They sub out part of the project and part of the payment fee to you, the subcontractor, to do part of it.

Daphne: Would that kind of company have their job listings for freelancers on LinkedIn or other job search boards?

Jay: Potentially, but a lot of freelancing is kind of a relationship game. You need to build relationships with people who run these service-based businesses and get them to trust you so that they know when they need added capacity or need this other skill set, Daphne is my person for this. Daphne is my copywriter. I’m going to go to her and bring this to her first. One by one, you have to build relationships with somebody running an agency so you’re top of mind when they have that project and that capability that they can’t do themselves. 

They might hire for this on path number three, which is a freelance marketplace. There are these websites, these marketplaces like Fiverr and Upwork, where it’s two-sided. There are people posting jobs and there are people fulfilling the jobs. I would really recommend those going this route to build on Upwork, and not Fiverr. Fiverr really incentivizes you to shoot the bottom on pricing and go for high volumes. It’s a really, really hard game and not one you want to play long-term. 

On Upwork, you can start to build a profile and a history around yourself and the work that you’ve done and charge very reasonable rates. If you get to a point where you have done a lot of work for people and you’ve been reviewed well, it’s kind of a rich get richer circumstance. A lot of people are trying to hire the best people. And then there are also a lot of people trying to hire the cheapest people. Unfortunately, you might have to spend a little bit of time underpricing yourself to get some really great outcomes and really great portfolio work to put on your profile. Then you can be one of those highly ranked and sought-after copywriters.

So, some of these agencies that you might subcontract to might be hiring on Upwork. But usually, it’s a relationship game, just like direct a client. And the hard part with subcontracting is that you really have no control or predictability. It’s not on you to sell the work and you don’t know when it’s coming. It becomes really hard to depend on it. That’s why I tend to recommend a portfolio approach to these three, especially in the beginning. That way you can start to flatten out some of the seasonality from one of them using the other two.

Daphne: Yeah, I’ve seen a lot of freelancers start on Upwork and use those strategies of making sure that they’re standing out above all the other clients. When somebody posts a job posting, let’s say Pinterest pins or copywriting, they’re the ones that go above and beyond and actually create a small sample or a small snippet that really shows that they’re qualified for the job, even if they don’t have ratings. 

And then as they start to build their ratings, and they start to build on Upwork, they actually take them and start pulling those reviews onto their own website. Then they can start branching out in that way. Those are the experiences or the reviews that they’re showing other people.

Jay: Yeah, totally. The same thing that we talk about with trying to stand out in interviews applies when trying to stand out on Upwork when you’re getting started, because you’re probably going to be applying for roles and gigs that a lot of other people are applying for also. So, you need to take some care in your response, your cover letter, your proposal, to stand out and show that while you might not have a lot of history on the platform, you’ve been teaching English for 10 years and can proofread the heck out of your screenplay or whatever it is. 

You can show how your unique skills map to this project, even if you don’t have a history of Upwork yet. Just call out the fact that you just joined this platform and don’t have a history because of that, but you’re really looking to have an amazing experience for your first few clients. You can even emphasize that you love it to be them. 

Daphne: Yeah, I love that. I love just calling it out and letting them know that that’s why you don’t have the reviews or history. And then just mentioning that you’re looking forward to putting all of your energy and resources into supporting their needs. 

Getting Starting In Freelancing? Check Out Freelancing School

Just pivoting a little bit here. Jay, you have a complete program that helps freelancers. Do you want to go into what is included in that program?

Jay: As a platform, Freelancing School has a bunch of different elements to it. I am consistently adding free articles to that website to help people get started freelancing. If you subscribe to the free five-day email course to help you earn more money freelancing, it will get you into my listserv and I send a new article to that every week. That’s free. We also have a community for freelancers that’s also free. So, there are a lot of ways you can plugin.

Now, if you want to get through and have the best and fastest outcome, the solution is one of the three courses that I offer. And those cover three different subject areas: business, marketing, and selling. There are a lot of course creators out there and service providers who will teach you how to be a really great copywriter, graphic designer, or WordPress developer using Divi. These are very specific skills and topic areas. Where Freelancing School’s focus is skill agnostic. Let me teach you how to start and run a freelance business so that it rewards you with the money and time that you want for the reason that you got into freelancing in the first place. 

I focus on setting up a sustainable business with processes that support you without taking all of your time. It teaches you how to confidently market yourself and your skills. It teaches you how to sell more projects or sell projects at a higher price so you can have more time and more money. It’s all about having the outcomes that you wanted as a freelancer in the first place, regardless of your skillset.

Daphne: I think one of the biggest changes that happened with me after I left teaching is I really started to invest in my own business and my own professional development. One of the main benefits that I got from that was being able to save time and energy by not trying to figure out everything on my own. There are so many times that we are that roadblock when we decide we’ll just find blog articles that will teach us everything. Then it takes us years or it ends up burning us out. We end up not actually making any progress.

About how long would it take somebody to go through all the resources in Freelancing School

Jay: So each course is about two and a half hours of content, and they average 16 lessons each. So, if you watched it from start to finish, you can watch all the content in about seven and a half to eight hours. But, each of those lessons is specifically designed around a learning goal. They each have a set of assignments for you to do afterward. They’re meant to challenge you that if you work through this, then you’re going to have a better outcome. You’ll actually have applied and built something from this lesson. 

So, I mean, you could fire through all the content in a week and have a great experience. I’ve had students do that. You can also space it out over a couple of weeks. Information is abundant and there’s some version of all the information for free. So, anything that you would want to learn in Freelancing School, I’m sure you can find online for free. 

But, after four years of freelancing myself and breaking that coveted six-figure milestone, I really do believe that with all the advice that I share with other freelancers and all the things that I’ve learned, I’ve taken the time to cool them down into 48 lessons that are ordered in a specific way and oriented in a specific way to give you the most efficient path to learn these skills to start a business and have that business reward you with the money and time that you want.

Daphne: Jay has offered an exclusive discount for Teacher Career Coach podcast listeners. You can join his Freelancing School for 20% off using coupon code “TCC”  

Jay, thank you so much for joining us here today.

Jay: It was so fun to be here. Like I said, teaching runs deep in my family. I love helping teachers earn more and love their work, whether it’s in addition to teaching or going in a new direction. I just loved the opportunity. So thank you for having me, Daphne. 

Daphne: Thank you so much. 


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