EP 4: Getting Your First Paying Client

In this episode of Second Act Freelance, host Judson Voss provides seasoned professionals with actionable strategies to secure their first freelancing client. Voss highlights leveraging personal networks, utilizing gig economy platforms like Upwork and Fiverr, and making targeted outreach on LinkedIn. Listeners will also learn about setting appropriate expectations and maintaining professional ethics during their transition to freelancing. Practical tips, encouraging insights, and a reminder to maintain patience and resilience make this episode a must-listen for aspiring freelancers.

00:00 Introduction to Second Act Freelance 00:49 Getting Your First Client: The Crucial Step 02:39 Leveraging Your Network 02:52 Networking Tips and Overcoming Fears 04:16 The Value of Your Network 05:15 Reaching Out to Your Network 14:48 Freelancing Platforms: Pros and Cons 18:54 Using Social Media to Find Gigs 20:33 LinkedIn Strategies for Freelancers 27:46 Recap and Final Thoughts

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Transcript

  Welcome to Second Act Freelance.  The show for seasoned professionals who are ready to leverage their knowledge and experience to create freedom and financial security. Whether you're nearing retirement and seeking new challenges, a mid career professional looking for flexibility, Or someone simply ready to break free from the traditional nine to five.

This podcast is your go to resource for expert advice, inspiring stories, and practical tips on how to thrive as a freelancer for your second act.  Welcome to another episode of second act freelance, the podcast dedicated to helping you kickstart your freelancing career. Especially if you're just a little bit older and you're looking to make that exciting leap into the world of self employment.

I'm your host Judson Voss, and today we're going to take a deep dive into what I think is probably one of the most crucial steps in your freelancing journey. And that is getting your very first client. Now, um, whether you're. Coming from a long career, starting fresh in the freelance world, getting the first client can seem a little bit daunting.

I get that. Um, but today we're going to break it down into some bite sized morsels so that we can walk, walk away with some action items to help you land that very first, uh, gig. And just as importantly, start building your freelance portfolio. But before we dive in, just a quick reminder to subscribe to the podcast, whether it's on iTunes or Spotify or anywhere else.

And, uh, if you find this info helpful, two things I'd love is one, leave us a review there. Cause I know that people  decide whether to spend their time on some content based on reviews, which I do the same. And the other thing I'd like, if possible, if you do find it helpful and You know, other people that are sort of thinking about the same journey you are to refer us to them and send us our podcast information. 

The other thing you can do for yourself is if you go to secondactfreelance.  com there is a free ebook there, it's success. In your second act and there's eight chapters, I think I have in there, maybe 40 pages, so it's not too long to go through, but there's, there's a bunch of exercises and some other information to analyze.

One is freelancing right for you. Let's be honest, may not be for some, maybe for others. And then number two, if it is some first action steps to take to head down that path of getting into freelancing. So that's it for all of the pre amble type of stuff. Let's get into landing your first client.  I would say the very first step  in getting your first client. 

Is leveraging your network. Now, um, leveraging your network can, can look a lot of different ways. And so we're going to talk about sort of three things today that we can look at individually to, uh, leverage our network, but I'm going to say, and you'll probably get tired of hearing me say it, that I believe that the key to making a difference in your business, I'm not sure it really matters if it's freelancing or anything else, to be honest with you.

It is networking, learning how to network, well, how to do it efficiently and overcoming The fears you may have in networking. I'm going to be honest with you. I have fears too, asking somebody to go out for coffee or even worse asking somebody for a favor or to refer me to somebody, uh, for whatever reason that, that just scares me and turns my stomach.

You may be the same way. Maybe not. Maybe you just, you love that type of thing and you can't wait to  get in front of somebody, chat them up and ask them for favors. But that's just how I am. And I think a lot of other people are too. So number one, you're not alone in that area. Now we'll go in deeper dive later about networking.

There's a little bit more in the book success in your second act that you can grab from there as far as networking and some tips. But one thing I will say is, uh, um,  that's in the book. But also that I would think about, and I picked this up from Jeff Henderson, who wrote a great book about starting over in your career.

And one of the things he says is, um, what, what, you know, may make you money.  And I'm, I'm butchering this quote like crazy. And I really should look it up before we start  and actually read it to you. But basically what, you know, may, may, uh, make you money, but  how much money you make is determined. By the size and the health of your network.

And that is, I can't think of anything that is more true when it comes to starting up your freelance business than that.  If you have a really good healthy network from day one until day 6, 000, that is going to make a big difference. If you're running out of business and you're, you need some more work, what that network looks like and how you can tap it makes the difference between freaking out and worrying about how you're going to pay your bills to just turning on the faucet and bringing in more work.

I honestly, honestly believe that.  So a few different ways we can leverage our network. First thing I would do  is reach out to people you already know. So here's, this is just me. What I do, um, I think I talked last time about  having one sheet of paper and writing down your strategy for something when you work on it.

But what I would say when it comes to networking is get out another blank sheet of paper, just start writing down  all the people that you know that are either in your business or may know somebody that's in your business that may be looking for someone, which means it could be your next door neighbor.

It could be family members that have nothing to do with anything in, in your business or the type of work that you do, but they may know other people that are. And so  I'd say nobody is off limits from, from that perspective. Um, You know what the sheet of paper thing to I do everything on my computer. I use notion love notion.

Um, but however you want to do it do it The key is is don't exclude people just because you've decided that they are not going to bring you money today They may not bring you money tomorrow But they may know somebody that knows somebody that you get in touch with that down the road Ends up being a long term client and there's no way to know that from day one So I would recommend doing that Um Once you've done that and written it down and you've got that list and you sort of brainstormed without any judgment on that list The next thing I would think about is this  Our goal here is to get our first client.

So don't go and whittle that list down to oh I think this client can give me 80 percent of the work. I need to be at 80 percent capacity for the next six years What you wanted to get is somebody that is going to pay you to do the work you do and freelancing Today. So if it's five hours of work, if it's one small task, whatever it is, go out there and find that one individual.

And it's really hard to find one individual that may give you a couple hours of work to do something, uh, based on analyzing your list. The way you do it is you just have to go out and reach out to people. Once you have that list together, let those people know that you're looking to do some freelancing.

I get it if it's a coworker and you have to be a little careful about that, whatever that looks like. And I wouldn't, I'd say  never, um, Jeopardize your career or even more so never jeopardized your character by taking on freelance work in place of your full time job. If it's going to hinder your full time job, somebody is paying you whatever number of dollars to do whatever hours of work or perform whatever task it is in your salary job.

I would say always make sure you're doing that even when you're freelancing so that there's no question in your character along those lines. And usually when that's the case, then it's easier to reach out to people because you're not sort of submarine ing the work you're doing on your full time gig.

But anybody that's out there, just start reaching out and letting people know. And this is what I do because I just, I'm just not Not, uh, confident, I guess, in sales. And so instead of saying, Hey, Bob, I'm looking to do some freelance work and X, Y, Z, you know, I do that already, whatever. And I'm looking to pick up some side sidework in that area.

Uh, are you interested? That's a tough one. So usually what I say to people, whether I think they're the direct person that might give me some work or they just know somebody, just tell them, Hey, I've been toying with this idea of getting into freelancing. as a side hustle. Um, to be honest, I haven't started doing it yet, but still thinking about it.

And one of the first things I want to do is just find somebody that's looking for some, some help that I could help out. I mean, it was just a couple hours or whatever it is. I just want to see if I like it or not, to be honest with you. Do you know anybody that'd be interested in that? Or if that's even too hard of a close for you.

Um, I just wanted to let you know. So if you ever run across anybody, just let them know that, that, uh, I'm looking to do that.  If it's somebody that may directly be able to hire you the dollars to donuts, there's a good chance that I wonder where that saying came from dollars to donuts,  because it really makes no sense.

But, um, especially with inflation, it's like two 75 or three bucks for a donut. Now, I, anyways, the, There's a really good chance that they may be like, yeah, actually, you know what? I, I can use some help. And if you're just looking for a couple hours, that's pretty low, pretty low risk on my part, here's what I'm looking to do, or no, I don't.

But you know what? Just the other day I was talking to so and so and they said they were looking for somebody to help, or I was talking to somebody about you one day and saying, what a good job you do. And, and they're like, well, if you ever find somebody like him, that's looking for some side work, let me know.

And boom. There you go. And it may not be the first person. And after the first person you tell, or you say that to, or they say, Oh, yeah, good enough.  Um, you need to go to the second person and keep going and going and going until you get that first person. Again, our goal here is not  to build a business today. 

Our goal is to get that first client.  So just go until you get that first client. And if somebody says yes,  hit pause. Just stop and do the work. Okay. Um, I know it can seem like, no, I got this momentum. I'm going to keep going. I get it. I totally get it. And if somebody comes and throws work at you, well, then you have to rethink that, but I'm just saying day one, the goal, get the first client.

So when somebody says, yes, go into delivery mode and start doing the work to complete that project, whatever it is with your first client. Um,  some folks have said to me, Hey, what do you think about  to get my first client doing it for free?  I think,  I think we all need to have a little more confidence than that.

if we really believe that the work we do has a value of 0 to it, I would highly recommend not doing the work. Number two, uh, I've gone down that road before I've helped people out. Even after I built my business and I really didn't have time to do extra work that I was getting paid to do, let alone extra work that somebody was going to, uh, get for free. 

Um, I've been there and what I found is the folks that get the work for free are some of the worst clients you can work with. And you can argue with me on that, but if you're arguing with me, most likely you haven't ever done free work for people  that, you know, that's not the same thing as volunteering at your church or charity or the, you know, the food bank or something like that.

That's not work for free. That's volunteering in service. Those are two different things. But if there is a job you do, if you're. We'll just take from me. For example, I do software consulting if I do that work and I get paid 150 bucks an hour, which is about what I make, um, and somebody, I do that work for somebody for free, I have just given away 150 per hour for that number one and number two, what I've done is change the value of the work I do to 0.

And that's just not the case. Um, but people that get the work for 0 treat you as if the work you do is worth 0. And I promise you, that's how it is. So what I would recommend is just keep going until you can get somebody that's going to pay you. for the work that you do. Again, if you're doing the work in service as a volunteer to help out a group, that's great.

There's no problem with that. But what I would recommend, if you're starting a freelance business, that you do the work that you're going to do in your freelance business, you get paid for the work you're going to do. That's not in your freelance business as a volunteer you do for free and try not to mix the two.

And most situations, especially if you're just doing it to try to get that first client.  Okay, off my soapbox on that one. You, but of course, keep in mind, everything I say here is up for debate. You can choose to do whatever you'd like, but, uh, in the comments below, if you've been in that situation where you've given away work for free, uh, let us know your experience.

If it was a great experience. Awesome. Put that down there. Let us know what that was, what you did to make it a great experience. And if it wasn't so great, let us know as a cautionary tale beyond just my cautionary tale for other folks that may be thinking about doing that.  So now, uh, that's the number one place I would go to.

And it is always, always, see if I can say that again, always. Your network and people, you know, by far the best place to get your first gig. It's just, people know you, they trust you. They've seen your work. They know who you are. Um, if you haven't freelanced before for somebody else and they don't know if you'd be a good freelancer, even though you're good in the work you do in your career, uh, it's easier for them to take that leap because they do know and trust you.

They know your character and it's easier to do that than an anonymous person.  That maybe they believe that you're good at your job. Don't know if you'd be good at managing a freelance project. So people, you know, by far is the first.  The second thing that. Uh,  I don't do to be honest with you and we'll, I'll talk about why, but it may be a good place to get your first gig is through some of the, what do they call them?

The gig gig economy sites, the freelance sites. Um, so like Upwork. And places like that, and I'm not disparaging Upwork at all. I use Upwork. I have folks that, um, do work for me through Upwork. Fiverr, depending on the type of work you do and what area it's in, is another one. And again, I, I use Fiverr, um, the intro to the podcast as a voiceover person from Fiverr.

So I have zero, zero issue with using Fiverr and I don't really have an issue with  folks freelancing through Fiverr. But what I, what I will say is this, going back to what I finished with  option one, the network. When you're doing it through, um, Upwork, Fiverr, any of those sites,  people don't know you. And people that don't know you, don't know your value.

And so they're willing to pay something for your work, but they are also willing to pay less for your work because there's a risk to them.  So I think if you have a dollar amount that you're worth in the market  and you, Do jobs on Fiverr, Upwork, again, comments below, email me, let me know where I'm wrong on this.

But what I found is that you tend to get paid less through those. Partially because again, that risk mitigation that they're trying to avoid the risk of sort of being in a place where they don't know your work, so I'll pay a little less because I don't know what I'm gonna get out of it. Totally valid too, from a human nature perspective. 

Uh, and then the other thing is too, there's, you know, the other 6, 000 people doing the same work and is much tougher to differentiate yourself from the crowd. And number two on that, we are talking about getting your first client. So it is considerably. tougher to go and get a gig on Upwork for your first gig when you're competing against a ton of people  and the person hiring doesn't know you. 

And number three, those other people have a lot of portfolio on Upwork. So the other person knows if they've done a good job for somebody else or not. And if you're getting your first gig  and they look at your portfolio and it's, Goose eggs. I mean, where are they going to go? They're going to go to the other people.

I would too. You would too. And that's just how it works. So is, I'm not saying don't use Upwork, don't use Fiverr, any of those places. I'm just saying as your first gig is difficult. Now, if, if it's a, Uh, if you've hired, gotten hired outside of this and used your network or something like that, and you want to do stuff through like a  Fiverr or an Upwork or something like that, go for it.

I would recommend anybody that you work with that's not on those platforms, at least put together some type of a small gig for them on, uh, Upwork so that they can review you. They may be sort of reviewing you for work you've done outside of Upwork in the past, but they're still reviewing your work. And that will allow people that are on like the Upwork platform to see, Oh, these other real human beings have used you and they're happy with you.

And so definitely that will help you out. But first gig, I think that's very difficult. I think if you go and put a post up on Upwork and you're looking for work and you start, um,  Pitching on to different jobs that are open there. I think you'll get good at pitching. I'm not sure you'll get good at getting work.

At least on your first gig. That's just my two cents on there. Again, I'm not saying don't do it. I'm just saying that's how it works.  I also think you're going to get paid less through those platforms. It's just a matter of competition, supply and demand. That kind of thing.  Then I think the last place to look. 

At least for now there's others. I think I've probably got a list of 10 that I can think of, but as far as again, first gig, just trying to get out the gates, that first gig to get some work, to have something in my portfolio is through social media. Now, um, what I lump in  Twitter and Instagram and those things with LinkedIn, I guess you could, but when I'm talking about social media for getting your first gig, I really, really am talking about.

About LinkedIn. And, um, when I'm talking about LinkedIn, I'm a little.  Funny about this again, trying to get a first gig, trying to get it fast, trying to get off the ground, that first feather in the cap type of thing.  So I'm not building a long term strategy. Um, I'm not building out content to get followers.

And then, you know, two years from now, I've got 3  million followers and I'm going to get that gig. I'm looking for somebody that wants to throw me a couple bucks today so I can get into the portfolio today, which is a different strategy. I think when it comes to LinkedIn.  And so, uh, I'm not saying don't put content out there.

I'm not saying don't let people know you're looking for work. I'm not saying don't do any of that. I, yeah, yes, do all of those things. And then sure. In the future, we'll talk a little bit more about some things on LinkedIn that you can do or other social media to gain a following that allows you to, to grow that.

But at least today, if I'm trying to find a job, one single individual job, I think you have to take more of a proactive. The target approach to it.  Um, and to me, and  when I say I think this is what I've done, this was worked well for me. I have a network. I've tapped that network. But just like anything in life, you don't want to just sit in one area you'd like to grow.

Right. And so I've gone outside of that network of known people that I have to build a network of people that I didn't know before. And I use LinkedIn for that. Um, and very basically, here's what I would say. And I, I want to throw this up there as a, and put a guardrail around this because I know people, I Don't do it this way and they end up being disingenuous and turning folks off  And it's funny because the ones they usually turn off are  Recruiters who are also being disingenuous Sorry, recruiters, there's a lot of you out there that are disingenuous with your recruiting habits.

Uh, that doesn't mean there's not good ones out there. You know who I'm talking to. I'm talking to you. Um,  but if anybody that's ever had a recruiter that's disingenuous, hit them up on LinkedIn. You know what I'm talking about too. It's, it's an unfortunate part of the, of the deal. Again, that's when you, somebody doesn't know you, it's easier for them to not be the same person they are when you're standing in front of them and it just happens.

That may be a  unpopular opinion, but it's certainly an opinion. Anyways. So to not be disingenuous, I would not  do this with under the guise that you're looking for a job. Okay. I just want to say that up front so that you, you use this. tactic, this strategy, this tip, uh, with the intent or the best of intentions and doing it in a way that you're not going to burn any bridges or leave a bad taste in somebody's mouth.

But this is what I do. I look at the jobs that are available, um, for me, because I've built a strategy and a niche into not just what type of work I do, but who I do the work for. That's probably like 

I've designed who I'm going to work with and the type of people I want to work for. That doesn't mean good or bad. It's the type of business and the kind of work they do.  And, uh, so since I've done that, I have a very targeted group and so I look at the job postings for people that fall in Into those categories that are sort of my perfect target. 

And I see the jobs that are out there. Now, what I don't do again, going back to putting up some guardrails on this, I don't go and apply for the job and say, Hey, I'm looking for a full time job when I'm not at all looking for a full time job. Instead of what, what I do is hopefully the hiring person for that job is on the listing.

And if that's the case,  excuse me, what I do. Is I reach out to that person, send 'em a message however I need to, sometimes they have their email addresses and their profiles, and I'll send an email. Otherwise, I just use a LinkedIn message and say, Hey, so and so hiring manager, I see you're looking for this role.

I am not looking for a full-time job, but just so you, but I just wanted to reach out because this is what I do.  The same work, I've been doing it for 20 years, you know, whatever, accolades, take a look at my LinkedIn profile, whatever that is. I am looking to pick up a few hours work on the side. And so I know that sometimes when you're in the hiring process,  there's things that need to get done and you don't have the perfect candidate yet and they're not on board and they're not ramped up to do the work yet.

And so it can be stressful.  I just wanted to throw my hat in there to say, if you do want somebody that can hop in there, take the reins right now, help you out in the gap until you find that person.  I'd love to chat.  And that's it. And it's true.  I don't know if you, if you've been a hiring manager before, or you've been somebody that manages folks and you've had people leave, quit, fired, whatever it is.

Um,  you, you know, if when you're looking for somebody else, so the work used to be done by somebody, the work is not being done by somebody now. And that's a stressful situation. And if you can have somebody come in that is competent and has good character, we'll do good work  for whatever time period that is. 

That is huge value. And you know what, if they don't want that.  If they're good with waiting, they'll just ignore your message or say, no, thanks. That's totally fine. But I put a list of those together and I reach out and I just send that, that note to them. Occasionally I'll add in there a little extra about, Oh, I know so and so in this business and I worked somebody that used to, that works at your company, whatever that is, if I need to, but don't let that stop you from sending the message in the first place.

If you don't have some personal connection, Carrot, because to be honest with you, I don't think people read more than about a sentence or two of your LinkedIn message or your cold email. So just, just the key is to send it and less about what's in it from day one. So that's what I do. Um, may or may not use it.

That's up to you, but that, that's what I do is I just reach out to folks now down the road. Yeah. If. Okay. Thank you. You get to the point where there are no jobs that are out there. The other thing I would do on LinkedIn is just find target companies. That would be the kind of people I want to work with and go to the, go on LinkedIn to their company page, find the person that may be the hiring manager or, um, HR would oversee the departments you would be helping out on a freelance basis with and shoot them a message with the same type of thing.

Hey, this is what I'm doing. This is what I do. I've been doing it for years. Be honest. I just know getting into freelancing though, but I have been a XYZ for a whole bunch of years and I've been doing it in these companies, I've got all of these recommendations on LinkedIn, but I am just itching to, to get out there and do some other work.

And I wanted to see if you have any work, you'd be interested in having me partner up with you on, and just leave it at that. I would also recommend keeping that in the spreadsheet. So you know who you've reached out to and who you haven't. And so you've got that info later. And also,  if you're like me, it's really important to have that because I have people reach out like six, eight weeks later and say, Hey, I got your message or I got your email.

Uh, I'd be interested in talking. And I'm like, Oh crap. Who are you?  Um, and I've got to dig back through and do a bunch of research. If you've got it on a, in a database spreadsheet or something, I use notion of course, um, It makes it a lot easier to dig up that person's information and be like, Oh yeah, I remember now there's my note.

They were looking for this or they do that or whatever. And so you can, you can use that. So that is my two cents on social media. Um, mostly I stick with LinkedIn. I'm sure there's other places you can go. There's forums for different groups, but. Uh, here's what I would say and getting ready to wrap up for today. 

If you just put a hundred percent of your effort into those two areas,  I think you have a really good shot. It landing that first client and that's what we're trying to do now. We're going to talk next time about how to close the deal and how to, uh, sort of set up the contract and do all that type of thing.

But for today, first client, figure out how to find them, go out there big, wide net and try to, uh, Try to find those folks. We're going to have to talk a little bit about money too. And you know, what happens when they ask you how much and all that kind of stuff. But for right now,  we're just, we're not looking for somebody to sign a contract.

We're looking for somebody to say. Maybe, maybe let's talk a little bit more. And that's a wonderful conversation in and of itself. If somebody says, let's chat. Um, even if you're getting no work out of that, most of the time, when I have those conversations with people, I learned so much, I get so much information from them about the business, what they're doing, what other people might be doing, uh, new ways.

to  frame up what I do and how I add value to companies. So there are no lost conversations. Any conversation that I have when I'm reaching out to people sort of cold for this type of thing is, is a good conversation. So, uh, very quick recap on this.  Think really simply go out to the people, you know, or the people who know the people, you know, and just let people know.

That you're looking to do some work. Don't make it some big, huge thing. Don't turn, don't write a business plan to get there. Just try to get the work. By the way, one of the really nice things to, to, I should say really great things about getting your first client is, uh, number one,  you build this.  Enormous.

I don't know. Maybe I'm overstating that amount of confidence in the fact that you. Did the things and got the work by saying, going out and telling people, you're looking at somebody saying, yes, I don't know how to explain any better. How good that feels to know that you put the work in and you're getting results out of it.

Then you might've gone to 20 people and yes, 19 said, no, who cares? One said, yes. And you know what? If. Every time you do it 19 say no one says yes, that's awesome Because now you know when you're looking for more work I just need to go out to 20 people if I want one more job And if I want two more jobs, I need to go to 40 people and BAM I got the work that I need and so there is a level of confidence that an energy That comes from that.

I promise you, when you get that first, yes, you're just going to want more and more yeses. We'll talk later about how to start saying no,  because there is a disease that comes along with that. That could be even worse than not getting work. Um, but that will come later. And the number two thing that you get out of this, that sometimes is overlooked because you're so afraid of asking people for work is when somebody says yes, they actually pay you.

You get a couple of bucks and you might think, well, it's not that much money. I make a  good amount of money. I'm a six figure professional, whatever that is, but I don't know, an extra  five hours at 150 bucks an hour is yeah, it's only 750. And if I look at what I get paid in a month, yeah, it's not, it's not.

You know, it's not putting the Lamborghini in the garage, but 750 bucks once every month. That's like a decent car  payment in the garage. Um, and I'm not saying that's how you should equate it, but it's true. It's real money. And while you're nervous about getting that first client, getting a little real money, Is a nice feeling to go along with it.

It's going to, it's going to keep you moving forward a little bit, maybe even put some money aside to, if you do want to do some things later in your business that cost money, you'd have that, that cash there. So that's my take on it today. Um, that's it for today's episode of second act freelance. I hope you found some of this helpful and, um, hopefully if you didn't find it that helpful, but a little helpful, you'll listen to it on a 1.

5 speed like I do. Most of the time, but most importantly, I feel a little more confident about going out there and, and landing your first client again, if you enjoyed this episode, don't forget to subscribe on iTunes or Spotify or wherever that is. Leave a review and share it with a friend. Maybe while you're networking, somebody says to you, Hey, I don't have any work, but I'm actually looking to freelance.

You could always recommend second act. Freelance is the podcast to go to. Um, I just came up with that on the fly. That was exciting. Anyways,  as always, you can find more resources. You can grab our free ebook at second act freelance. com. Where you can pick up more information there. So thanks for listening today.

And next time we're going to go a little bit deeper into what do you do once you actually land that first client and start to think about how we start to build this business, whatever size you want it to be until then. I hope you keep pushing forward, take small steps every single day and stay inspired.