The Long and The Short Of It

Episode 123 - The Freelancer Cycle

Transcript:

Pete: Hey, Jen.

Jen: Hello, Peter.

Pete: So in the last week, I and we have finished a handful of projects. And they just all happened to, for me, they all happened to finish at once. And it got me thinking about seasons (which we've talked about before), but also cycles, and how all of this relates to freelancing. And I thought that we could unpack, from one freelancer to another, or a former freelancer to one freelancer.

Jen: Ooh, yes. The freelancer cycle, very familiar with that. Let's do it. This is The Long and The Short Of It.

Pete: Okay. So I guess, context. I identify as a freelancer. And maybe we should unpack our definitions really quickly. Which, I think about freelancing as being getting paid for your work. So, you are the product/service. And when you do a certain thing, like coach somebody, you are paid for that service. Is that how you think about it too?

Jen: Yeah. I'll just point everyone toward two podcast episodes. One, the recent one you and I did in conversation with Seth Godin a couple weeks ago, where we asked him about this distinction. And then the other is the thing that made us ask him in the first place, his incredible Akimbo episode. I will drop it in the Box O' Goodies.

Pete: The greatest Seth Godin episode of all time. Do you remember the day that came out?

Jen: I listened to it like a hundred times.

Pete: I woke up to the most...

Jen: I just kept rewinding and going back.

Pete: Yeah. I woke up to this frantic series of messages from you. Like, "You have to listen to this. I listened to it twelve times."

Jen: Well, it was the first time I felt seen in that way. That...

Pete: Yeah.

Jen: ...I had somehow erroneously devalued the concept of being a freelancer. And then I recognized that, "No, I really am a freelancer. Like, I want to be the one making the work. I don't want to make the structure that allows only other people to do the work. I want to be the work."

Pete: Yeah. Which is the really the important distinction between entrepreneurs and freelancers. So entrepreneurs, he describes as being someone who gets paid in their sleep. They create something bigger than themselves that then scales to a point of leverage where like they're not even required. They're just kind of in the background, running a system.

Jen: Yeah. And I feel like we have to...to be fair to entrepreneurs, you only get paid in your sleep after a certain point.

Pete: Oh, totally.

Jen: Because otherwise you don't sleep, and you're working your patootie off.

Pete: This is true. For many entrepreneurs, they just don't get paid because it's such hard work. Yeah.

Jen: And they don't get to sleep either.

Pete: Yeah, yeah. That's a great call out.

Jen: Okay, so tell me about this cycle. Because you're right, you just had everything you were working on come to the end of its contract.

Pete: Yeah, which is weird. Weird. It's both exciting and terrifying, if I'm honest, because as a freelancer you (again, like to go off the definition), you kind of live and die by the work that you're doing, and the people that you're serving. And so when a project comes to its natural conclusion, nothing dramatic happened. This was always going to happen. There is often a moment I have of, "Oh. What am I going to do with all this space? What am I going to do with all this time? Who is my next project going to be with and for?" And then honestly, if I get on the overthinking side of things, is like, "Oh, you fluked it to this point. No one's going to hire you again. You're not going to have another really great project. Like, you just finished the Big Ideas Lab with Jen, she doesn't want to run that with you again." Like, I get honestly caught up in these really weird stories because there is less work to do day to day, that prescribed work than there was, say, a month ago or two weeks ago. So there's this really weird cycle, and I know it, and I see it. And it happens to me multiple times a year. And yet, it still trips me up every now and then. Like I'm sharing now, I go through this cycle of...I think a lot of freelancers, we love to do the work. So when we're running the Big Ideas Lab, or I'm coaching someone for like a three month period, it's like, "This is great. I'm showing up. I know where I need to be. I know what I need to say, or how I need to approach a conversation with doing the work." I think all freelancers can probably relate to loving the craft. That's why we do it. The bit that we love less is looking for the next project, or thinking in sort of a slightly more strategic sense about our business and where is the next workshop or keynote or coaching relationship coming from. So, there's this tension of getting so caught up in the work that we kind of forget about that. Or then the work finishes and we're like, "Oh, I guess I better focus more on that." And it becomes, as you can tell by this conversation, a little thrashy.

Jen: Yeah, it is an interesting cycle. And I'm guessing every freelancer right now is like, "Yes, I know this so well." That when a job is ending, you convince yourself you will never, ever, ever work again. "This is my last show. This is my last talk. This is my last workshop. I better make it count because I'm done, baby. I'm done."

Pete: And I'm over three years into this journey, and I stand before you as someone who is going through that right now.

Jen: Wow, yeah, that's so interesting. I kind of want to pull on this a little bit. And then, I have a different cycle I'd love to talk through that I'm cycling through at the moment. What do you do to first get your mindset in a place where you can open yourself up to the work that has to happen in order to get the work you want to do? So now that you have completed this contract cycle, instead of deciding to commit to the story that you're never going to work again, there's something else that has to happen in order to help you pursue new clients. So, I'm interested in hearing your take on that. And then the other piece is something that I think all freelancers struggle with, and you pointed to it...but I'm just wondering, how can we make the pursuit of the next client something that is more delightful to partake in, rather than the slog that weighs us down?

Pete: Okay, let me do my best to unpack those questions. So the first one, I think of freelancing in...well, the work required in freelancing, you could always put it into two buckets. One is doing the work. That is the bit that we all love, like I mentioned. The other of it is working on the business. Which is, you know, whether it's updating your website, whether it's putting together a proposal, whether it's having a conversation with a prospective client who reached out to you. There is a level of working on the business, no matter who we are. And what I think is really important...which, I'm being a little dramatic in me saying, "Ah, I'm in this place of like I'm never going to get hired again." What I think is really important (which is what I try and do) is not being all in one of those buckets. So even when I'm executing on the projects that we have (i.e. doing the work), I still have a practice of working on the business. I have developed and cultivated that. I learned a bunch of lessons through Seth Godin and other freelancers that I've worked closely with, around what practices, what habits can you have every single day that nudge forward your business, not just the work that you're doing in this moment. So really tactically, that might look like reaching out to someone that you used to work with. Or, you know, I would say even recording a podcast with Jen is an element of us doing work on our business, on us as thinkers, as coaches, as curious humans. There are these like things that we need to develop practices in, rather than I'm all in in the work, and then all my projects finish and I panic, and I go through a phase of, "All I need to do is create more opportunities." I don't think that pendulum is where I'm at. And I think that what is more helpful is developing a practice that we can show up with every day. And then when a project ends, and when we realize we have more space and more time, recognizing that we can dial it up a little bit. So, "Oh, instead of trying to send one reach out a day to someone in my network, maybe I'll try and have a call or a couple of calls every day, or maybe I'll check in with two or three people a day." So, just kind of dialing it up a little bit. The other thing (which I think you mentioned, perhaps, just prior to this call) is, to your point earlier about mindset, is just reminding yourself...you did this so beautifully for me, actually, before we jumped on. Which was like, "Oh, what a cool opportunity. Because you know something cool is going to fill that space. Because you're open to it. Because you have the space. Because you're putting generous work out there. Something will happen." And even hearing you say that, I was like, "Oh yeah. You're right. I believe that." So again, the practice of showing up, practice of putting work out there and shipping our work, something can't help but happen if we do that. There is a level of, I guess, trust I have in that.

Jen: Well, because if you look at the data for the last three years, that's happened every single time.

Pete: Every time I have a space (and I'm sure you're the same), something ends up getting created and it ends up being great. So, you're right. There is plenty of data to back this up, or as we would call it in Australia, "data". The other question that you asked, I really want to hit on. Which was, "How do you make that pursuit of working on the business, or the pursuit of looking for a next client delightful?" I think that's such a brilliant choice of words. And to me, the way that I do that, or I seek to do that is I make the practice, the task of working on the business, something I enjoy. So, I love connecting with other brilliant people in my network. I love having conversations like this with Jen Waldman. I love filling my calendar with inspiring people who I get to, you know, find out what they're up to and where I might be able to support. So for me, it's not, you know, creating this really gross sales outreach that just doesn't resonate with me at all or fit in with my values. It's like, "What are the things that I like doing that will help me move my business forward?" Great conversations with really interesting people, and shipping work like this, and the blog, and a few other things. So I think it's, yeah, picking things that you know you're going to enjoy.

Jen: I don't know why I feel compelled to say this, but you have a practice that I haven't really witnessed with anyone else who works with clients in a one-on-one capacity. Which is, your discovery call (or your vetting of clients) really requires them to do quite a heavy lift. And you're able to almost determined before the actual first virtual face-to-face, whether or not someone is a fit based on the work you've asked them to do to prepare to meet you. And I just find that amazing, because I think so many freelancers are so afraid of what we were talking about earlier. That, "I'll never work again and I'll never get another client." That they try to alleviate as much tension as possible as they are meeting prospective clients. But you almost go to the ends of the earth to add the tension. And it's a really interesting strategy.

Pete: And maybe I can elaborate slightly. So if someone reaches out about coaching, or a keynote, or a workshop, usually I'll respond with a series of questions. A series of what I think are generous coaching questions that, yeah, add tension to...if you take the time to reply to this, then you're probably ready for coaching. Or if you take the time to reply to this, then you've probably thought through this company workshop or this conference keynote that you're seeking. And then, the follow up to that will usually be...if it's a coaching relationship, for example, we'll hop on a call and I will just coach them for an hour. And like what happens every time, literally every time is in the last five to ten minutes they'll say, "So, how does this work? Coaching and working with you?" And I'm like, "Oh, we just did it." So yeah, they're very deliberate, those practices. You're right. Huh.

Jen: Yeah, I think it's very smart. Very, very smart.

Pete: Thank you. What was that other tangent you wanted to go down? I feel like you flagged there was a different line of thought.

Jen: Well, I'm almost wondering if this is like a completely different episode, but I'll give a teaser, a preview of coming attractions. Is, in 2020, I found myself almost by accident in the entrepreneurial seat, and had almost lost my freelancerness in its entirety. Because as I was moving my studio into the virtual space, I had to go back to having a founding mindset and my finger was in every single pot. Somehow, I was, you know, building out business models, and dealing with operations, and vetting different platforms. And it didn't occur to me until we were maybe six months in, like, "I am putting in more hours a week than I have in maybe fifteen years, and a teeny tiny fraction of those hours are spent actually teaching." And that was a very upsetting aha moment for me. Not that I don't like the building component, but not with a ratio of 90/10. And I had to really take a step back and ask myself, "Do I want to be an entrepreneur? Or can I take this business that I'm building...and I do have other people working within the business, so technically, it is an entrepreneurial venture. But how can I approach it with a freelancer's spirit, where my content, my work, my craft becomes a vital heartbeat of the organization?" I don't want to build something that I could walk away from and actually have it still run without me. I want to be integrated into whatever it is I'm building. And so, that has been like a big wake up call. So I've, in the last two months, really tried to come to the end of this entrepreneurial cycle and start a new cycle that allows me to tip the ratio back in the other direction. I'm not going to move out of the entrepreneurial seat completely. I mean, I am running a business that has other people involved in it. But I do know that at the end of the day, if I am not creating classes, working one-on-one with clients, getting into small groups, and digging into the mud with the artists that I work with, there's no point in me trying to build the business.

Pete: Yeah, yeah. I think that story that you shared is even more common than we realize, I feel like, especially without a really solid definition of what is a freelancer versus what is an entrepreneur. The pattern that I've observed in so many freelancers who have, you know, success or get to a point where their work is sustaining them is, at some point, they will start to talk about this word "scale". And at some point, because of culture, and the way that the conversations happen around scale, and startups, and, "Get bigger, and get more people, and get more clients," at some point, they'll reach this crossroads of like, "Oh yeah, so I have to train people to do the work so that I can scale." And that is flipping, to your point, into an entrepreneurial position, which I don't think necessarily a lot of them want to do. It's kind of...they feel like that's the natural progression, or that's what you have to do. So using myself as an example, I don't have any interest in bringing people on to teach them how to coach the way I coach so that I don't have to coach, or teaching people to give the talks that I like giving so that I don't have to give them. I absolutely like helping other people develop their coaching practice or their speaking business, but that's so that they can take that into their business. I'm not interested (just like you) in making myself redundant to the point where I don't get to do the craft, because the craft is the part that I enjoy. So I think it's really common to straddle that line, or to get too sucked up into the, "I've got to scale because that's what startups do, and I am a founder." And it's like, "Sure. But you're also a freelancer. And is it the craft that you're actually enjoying? So why not just give yourself permission to focus on the craft, or enjoy the craft?"

Jen: Yes, yes, yes. I mean, I feel this down to my toes. I wrote something down, and I don't even know what to make of what I wrote down. But I wrote down here, "clients versus customers". And I recognize that I want clients, and I have no interest in customers. And maybe that is also part of the freelancing mindset. Is, I want to have personal relationships with the people I'm working with. I want to have conversations about what's going on and how I can help them, and then tailor-make solutions and craft things with their specific circumstances in mind. And when I think about customer, the thing that comes to mind is a uniform solution, where I have created a product and then I would sell that one product to anyone who presents with a concern or problem that even remotely fits it. And for me, that's not of interest. Other people are incredible at that. But I want to have clients. I want to have personal relationships.

Pete: Yeah, me too. Me too. And you could, I think, actually extend that further in terms of the other side of a customer. Is where, you hear tech companies talk about users. And there's a brilliant documentary on Netflix called The Social Dilemma. And they point out that there's two industries that exist who refer to their clients/customers as users. And that is the drug industry and the tech industry.

Jen: [gasps] Woah.

Pete: Yeah. And so, I, like you, want to live in a world...and I think all freelancers, well, a lot of freelancers would agree. I want to live in a world where we get to work with clients, and collaborate with clients...not even "work for". It's a collaboration, I think, with our clients. And again, to your point, there's nothing wrong with, "I want to work with customers." But I suspect, with freelancers, it's probably about the former. That is, working with clients and being okay with that.

Jen: I feel like I want to challenge our listeners for a moment. So listeners, if there are things that are on your mind around this particular identity of freelancer, would you send in your questions? Or the things you'd like to hear us unpack, and maybe we can turn this into a bit of a freelancer series.

Pete: You can send your questions to hello@thelongandtheshortpodcast.com.

Jen: And that is The Long and The Short Of It.