How Much Should Freelancers Pitch Each Week?-EP099

I’m so glad you're tuning in for another episode of the Advanced Freelancing podcast. Now this episode was inspired by a handful of one on one clients and strategy session clients who come to me because they feel like they're not booking enough business or that their pitches aren't converting. I recently talked about this in my Facebook group because most of the time, when I dig a little bit deeper with these coaching clients, I find out that they're not really sending any pitches at all. So that's why this episode is focused on how much you should really be pitching depending on the phase that you're at in your business.

Now, it's important to remember that even an experienced freelancer is going to have ups and downs.

So you'll need to adjust your pitching expectations based on where you're at in your business. A fully booked freelancer is probably not going to pitch as much as someone who just lost their biggest or only client and now essentially has to build their business from the ground up.

The reason I want to cover this on the podcast is because it comes up in such a similar way. So often I hear somebody say, “I'm not getting enough business. I really wanted to be fully booked. I wanted to replace my day job with freelancing.”  And they sort of lead with that concern

or complaint. And then I dig a little deeper and say, “Okay, well, how many pitches did you send last week?” The answer is almost always something like two, one, or none.

That really confuses me. Because would you go to your personal trainer and complain, or your spouse or your friend and complain by saying, “I'm not really building any muscle.” If the answer to that was, “I go to the gym once a month, or twice a week for 20 minutes, essentially doing the absolute bare minimum.”

The truth is that you always should be pitching as a freelancer.

I think a lot of times people assume that once you're fully booked, you can turn that part of your business off. That is not true. I believe that you should always be pitching. So let's start with this idea of being the new freelancer who's really looking to scale their business up, or the intermediate experienced freelancer who has recently taken a major hit in some way.

A major hit could be that you recognized that you had a collection of toxic clients and that you went ahead and fired a lot of them. It could be that you had one client or a few big clients that let you go. I've had one on one coaching clients cope with that as well. Where they had one huge client then that client’s business folded or something else happened where they had to step away. It could be that you took some time off from freelancing.  So you're not new to the game, but you had to take a couple of months off for personal or professional reasons. And now you're coming back and you really need to ramp your business up.

Again, these are what I would consider more like crisis pitching situations. And you definitely need to turn up the volume on how much pitching you're doing in order for that to be successful. It is not enough to jump back into the game and send one pitch or two pitches per week.

Now, people are often looking for this magic number.

I'm not guaranteeing that what I'm going to tell you is going to be your magic number. But if you're not sending a minimum of 25 pitches a week, I never want to hear that your pitches are not working. If you're sending 25 pitches a week or real close to it, like 22-23, and nothing is converting, then we have a problem with the pitch, your samples, or how you're approaching people.  You might be targeting the wrong clients. 

But when you're only pitching once or twice a week, you do not have enough data to say that this isn't working. That is the absolute bare minimum that a fully booked freelancer should be sending. So if you are going crisis mode or if you are new, promise yourself that you're going to send 25 pitches a week.

Now I include everything in that 25 pitches.

That includes job board pitches, Upwork, reaching out to people on LinkedIn, and sending cold email pitches. That even includes if you do have previous clients, if you're that experienced freelancer, that includes following up with them and reaching out to see if there's more business they can offer you.

For example, I've had a client for three years that all of a sudden they just stopped assigning me projects around the end of December. And right now, we're about one month later when I'm recording this episode. And I didn't know why that was.  But the job I couldn't get them to respond to me in the Upwork work room. So I just closed the job and left them feedback and was like, “Okay, well what do I do now?”

The next step for me was finding the owner of that company who had had a few conversations with in the Upwork work room. And who I knew was the person who was paying the invoices. I found him on LinkedIn. And I connected with him.  I sent him a personalized message about who I was, in case he didn't remember. And we kind of had some back and forth for a couple of days. And it wasn't until he consistently saw me posting on LinkedIn that I think my name kept popping up into his brain.

This is one of the strategies I go over a lot in LinkedIn for freelancers.

It's often the lurkers or the people that you may have a really firm outreach method with, but they don't necessarily respond to that. It's sometimes the fact that they're looking and watching your profile. And they hear from you enough and see you enough that they reach out.

So for me that outreach was considered a pitch for that particular week.

I was re engaging that client and initiating that conversation all over again. And that client immediately after seeing me post different things about my business on LinkedIn, some of which were not even related to freelancing, suddenly reached out and said, “Hey, we really need to bring you on with a retainer.  We really have several projects per month that we need your help with.” So we negotiated that contract very quickly and got things going.

So that's just one example like a pitch does not always have to be from square one, you sit down and you write it. It can be a follow up. And it can be Upwork or can be all of the other things that I've mentioned. It could be following up with someone that you met at a networking meeting in person and you're trying to initiate that process.

I don't know why it's become so common that a lot of freelancers think that we have a lot of benefits in our business.  It is a lot easier to win clients, thanks to things like the internet. And thanks to things like job boards like Upwork. But that doesn't mean it's easy. If it were as easy as spending five seconds a day on your marketing, then everyone would be a freelancer.

The fact that everyone is not a freelancer should be telling you that there is work going on behind the scenes.

And it is not just the work that you do for your clients. As a freelancer, you are a salesperson.   That is your job. Yes, you might create content. As a virtual assistant, you might do admin tasks. You might design logos and other tools. But more importantly, you are a salesperson. And if you are not starting that sales process, initiating conversations, and sending out pitches, you will eventually have a lot of your work dry up.

This is something where a lot of those more experienced freelancers fall into a really bad habit that I will talk about in a moment. So if you're new or if you are in crisis mode, 25 pitches a week no complaining about problems with your pitching or that your business isn't growing, if you're not sending 25 pitches a week. Because if I am working with you one on one or if

you're in a strategy session, if you're in my facebook group, or you respond to one of my emails, and you know you have a legitimate concern, which is “I'm not booking business. My business isn't growing. I don't have enough clients on the books.”

My first question to you is going to be how much you are pitching? And if your answer is an hour a week or two pitches a week or three pitches a week, it is simply not enough. You're not serious about growing your business if you are only doing it a handful of times per week. So there needs to be a little bit of an expectation adjustment there as far as what it really takes to grow your business and to bring in business.

So perhaps you’ve been booked for a while.

So that was part one is for the person who's new, and for the person who's in crisis mode. Now, let's switch gears into the freelancer who's been at this for a while and is close to fully booked or is fully booked. This is a myth that a lot of freelancers assume, “Well, I'm good. I'm fully booked. I'm going to stop marketing.” And this really comes back to bite you if you need to fire a client. If a client's business folds or if a client fires you, that can be devastating if you've done absolutely no marketing for the last one to three months. Because you're essentially starting from zero in that crisis mode as well.

To guard against this, I strongly recommend having a pipeline of warm leads at all times.

This means that you might dial your marketing back, but you're still actively involved in marketing. So even when I'm fully booked, I am still posting articles on LinkedIn. And I'm still following other thought leaders on LinkedIn commenting on their posts and responding to their comments on mine. I'm still checking Upwork. And I'm still checking the daily job boards once a day. I'm not putting hours and hours into that effort. Instead, I might be only putting 30 minutes a day into Upwork. But I never let my marketing just sit there.

Perhaps I've got that process streamlined.

And I've got a virtual assistant posting on LinkedIn for me and I feel like I'm good. I still should be taking forward action steps with my marketing every single week. So maybe I outsource a lot of my marketing tasks to keep it on autopilot. But I might say, “You know what, I don't really have a funnel. I'm not offering a freebie to my clients where they get something after enrolling in my email list. And I'm not using that to nurture my leads and follow up with them.” You may say something like, “My blog sucks. I really need to fix it and pick the 10 blog post topics I'm going to write about next.” Those are also ways that you can still be involved in marketing, when you're close to fully booked or fully booked. Take on some of those bigger projects, so that you can continue to have people who are reaching out to you.

You know best what your turnaround time is on your pitches. For example, maybe you pitch on Upwork jobs. And it's like three to five days later and you've got that contract set up on Upwork. If you're doing cold outreach to somebody on LinkedIn or through emails, it might take a lot longer than three to five days. So pitching today, even on that simmer mode, isn't about the business you get today. It's about getting that person as a warm lead in your pipeline for the future. So the pitches that I send today, on my low power mode, are really about the best business that I'm hoping to book two, three, or four months later.

You can see why that's so important that you continue to send pitches even when you are fully booked or very close to fully booked.

Because what's the worst case scenario that could happen? Someone wants to hire you and you don't have capacity yet? Great. Put them on a waitlist. Tell them it's going to be another couple of weeks before you can bring them on. Fire a low paying client that you hate and replace it with this better person. I've never understood why people will hold back from pitching because they're fully booked.

I still think it's a good idea to have warm leads in the pipeline. You can always tell them no if you can't do the project right now. And you can always tell anyone no if they present a project to you that you're not interested in working on. You can always say no. And that puts you in the primary power position as the decider. Yes, you're reaching out to the client, but you are by no means obligated to work with someone just because you pitch them.

So why wouldn't you open yourself up to as many opportunities as possible? Where you're in the decision maker deciding whether you want to bring this client on or not. And what that looks like.  Perhaps you pitch them and you're pretty close to fully booked right now and you have one client whose contract is wrapping up. Use that as a negotiation and persuasion tactic. When you're talking to this new prospective client mentioned, “Hey, in two weeks, I have an opening on my calendar because I'm wrapping up a project. If you sign in the next 72 hours, I can get you on my calendar for two weeks from now and you can spend the interim two weeks getting me the information I need to do the job and getting me set up.”

So don't stop pitching because you assume that you're going to be fine or because you think that, “Oh, what happens if I get too much business?”

Listen, you can always negotiate around that. You could outsource that to a subcontractor. You could put the person on a waitlist. And you could give them an incentive like they have to sign up sooner and get the first available spot. There's so many options that you can pursue with that.

So it should never be an excuse, because that's what it is. It’s an excuse as to why you're not doing pitching when you're fully booked.

Now, the amount of work that you do on pitching will vary a lot based on where you're at in your business and the seasons as well.

I encourage you to look back at some of the previous episodes about slow seasons in your freelance business that will help you kind of prepare for that. There are lots of people who say, “Oh, every day is an opportunity to do business.” Yeah, sure. But your pool of people is much smaller in the three weeks surrounding Christmas. It's essentially a dead zone in August when nobody is even in the office and a lot of people are cramming in their end of summer vacations.

So can you get business during those times? Sure. But it's not going to be as consistent or as easy as it might be during other periods. So perhaps, let's say it's in the fall. You recognize that December is coming. Perhaps you turn up the heat on your marketing and your pitching now after recognizing that December in January might be a little bit slower months. So maybe you put in a little more marketing effort to try to secure some clients on longer retainers to get you through those months.

Pitching should always be either in the foreground or the background of your business.

It should never disappear entirely. And I have met way too many freelancers who have put it off, have not done it, or who think it's going to be a lot less work than it is. And the truth is, if you are not booked at all, if you have no clients, if you have one client, or if you're new,  you need to be doing 25 pitches a week. The first question I'm going to ask if you are fully booked or pretty close or you're an experienced freelancer and you have a couple clients but you haven't quite filled out your client roster with as many people or as much money as you would like.  Then you can definitely turn down the power of your marketing plan.

But it should still be something that you work on every single week, even if it's in small ways.  Even if that's 30 minutes a week that you take to write a handful of LinkedIn posts with the right hashtags. It could be that you get up every morning before getting started and you connect with five people on LinkedIn or you scan the job boards to see what's new. You do all of your follow ups together. It doesn't have to be a massive project when you are close to fully booked. But you always should be doing something that moves you in a forward direction with your business.