#25 - Peter Shepherd, Human Periscope
[#25] - Understanding Imposter Syndrome with Pete Shepherd
Pete Shepherd is the 6”7’ founder of Human Periscope, co-host of The Long and the Short podcast and a head coach of Seth Godin’s altMBA, an online leadership and management workshop. Pete specialises in helping leaders around the globe to develop, grow and create great change by allowing them to see things they can’t.
In this episode, Pete and Conor discuss the various strands of being a freelancer, breakthrough moments throughout Pete’s early coaching career, and understanding how to acknowledge and move forward with imposter syndrome. Key points covered include;
Pete’s transition from the corporate world into freelance coaching.
The process of discovery and the skill set of curiosity.
The Human Periscope – helping someone see what they can’t see just yet.
Building experience and confidence in coaching, and acquiring the first 10 customers.
Unpacking the nugget of pitching and pricing.
Managing marketing and maintaining momentum throughout the freelancer cycle.
Exploring social media; finding purpose and joy within your chosen platforms.
An insight to imposter syndrome and the impact of dancing with the universal feeling.
Practical advice for freelancers at the beginning of their journey.
For over 10+ years Pete has worked in leadership and culture helping thousands of leaders, executives and changemakers launch just as many projects, businesses, and experiments right around the world.
Connect with Pete Shepherd:
http://www.linkedin.com/in/petershepherd3
The Long and the Short Podcast: A podcast for curious people with Peter Shepherd and Jen Waldman.
http://thelongandtheshortpodcast.com/
Pete Shepherd’s blog – Noodle Scratchers
Pete’s Resource to help you find your First 10 Customers
Connect with First 10 Podcast host Conor McCarthy:
http://twitter.com/TheFirst10Pod
http://www.linkedin.com/in/comccart/
Resources:
Book recommendations:
The Prosperous Coach by Rich Litvin and Steve Chandler
The Win Without Pitching Manifesto by Blair Enns
http://www.winwithoutpitching.com/the-manifesto/
The Art of Possibility by Rosamund Stone Zander
http://rosamundzander.com/book-art-of-possibility.php
Steal Like an Artist by Austin Kleon
Transcription
SUMMARY KEYWORDS
people, freelancers, freelance, business, podcast, clients, started, unreal, projects, community, courses, create, building, find, relationships, realised, jay, deadlines, trust, programme
SPEAKERS
Conor McCarthy, Jay Clouse
Jay Clouse 00:01
I just want to help you earn more put a business in place that supports the lifestyle goals you have, which is probably giving you more time, whether it's creating digital products or content, or just spending more time with your family. So I made it agnostic of the discipline you're doing just to help you sell more projects earn more.
Conor McCarthy 00:21
Hello, listeners, and welcome back to the first 10 podcast. I'm your host, Conor McCarthy. And in each episode, I interviewed Business Builders on their first 10 customers, who they were they found them how they talked to them, or what effect they had in their business so that you can learn what worked and what didn't. When I'm not recording podcasts, I help Business Builders find their first 10 customers and grow their businesses. I do that with one to one coaching, and a series of online workshops. please do check out my website, Conor mccarthy.me. For more details, and to sign up to my regular newsletter. I hope you enjoy the show. My guest today is Jay Klaus Jay's website says that he quote, helps creatives thrive as business owners, unquote. And while that's true, Jay actually does so much more. And we really get into what those things are on this podcast. Jay is a true freelancer, he climbed the rungs of the solo freelance ladder to this point where he's created a series of assets in the form of courses, blogs, podcasts, etc. His courses are on topics such as podcasting, selling for freelancers, marketing for freelancers. And as we talk about these things are really must have for all freelancers out there. I'll include links to those in the shownotes. We start by getting into Jays early days, and the value that he found in his close relationships when he was looking for those first projects, as well as figuring out who to approach to work with. He has a great framework though chaturbate. We also talk about the power of the ask, and as well, earning trust from yourself. First, we talk a lot about the idea of finding balance as freelancers which is so important, especially when we juggle so many plates in our businesses. We talk about community at Jay started a community called unreal collective A number of years ago, was when I first met him, and he recently got acquired by Pat Flynn. So we get into the weeds of what it truly looks like to create, grow and manage a community of people. J really walks the walk. As I said, he has personally created a bunch of resources that have helped a tonne of freelancers launch successful businesses. And apart from just being a great guy, as you'll hear on this podcast, Jay really is a model for understanding what it takes to run a great freelance business. Also, there's a secret surprise in the show notes. And it's something Jay was kind enough to share something that he used when he was starting out, that will help all freelancers listening to this episode on their journey. So please enjoy my chat with J class. So Jake lives First of all, thank you very, very much for taking the time to be with us here today.
Jay Clouse 02:53
Anytime I can hang out with you, Connor, I'm up for it. So I said about to go before we started recording, like it's kind of hard to throw in that era Do you and what you do, because you do a lot. So you want to give us a quick summation of your business journey, even in the last few years. And we can we can jump in at one point. Totally. And it's been pretty, pretty much tied to my own journey of expanding my view of what entrepreneurship is. Because I started with a software company that sold tickets. That was in 2014 2015, we sold that company. And then I took a job as a product manager at a healthcare startup that was super venture backed. and realise I didn't want to freelance forever. In fact, I wanted to freelance for as short a time as possible, because I would rather decouple my time from how I'm earning an income, and instead focus on building more leveraged passive assets. And so that became online courses. It became content, which is mostly it's not a course it's either a workshop or the podcast that I do now. And so today, I mostly identify with the idea of being a creator, because most of the time I'm writing or I'm podcasting. I'm studying other creators through my work, and really focusing on building community online, as as something that's interesting to me. But that's always evolving. And I'm sure that will change over time as well. But probably the core of being a creator and trying to make an independent living from my work is going to be the most consistent part. Okay,
Conor McCarthy 04:51
it's so interesting because this is this whole season of the first 10 podcasts is the freelance season. So it's really exciting to talk to you Who has been a true freelancer, and you've done something, you've done a few things that a lot of freelancers I meet, want to ultimately do, you know, have paid courses have community elements have a body of content that the they're kind of proud of it is that they're working on their behalf. If you like, when you go back to the start of your personal kind of freelance career back when you were starting off getting your first 10 customers, can you tell any stories from back then that you could remember about getting those those clients, those customers, I remember
Jay Clouse 05:31
probably the greatest gift being that I had a good friend of mine, who was just so excited that I was going back on my own again, because he and I were building businesses and parallel software businesses. And then when we sold that company, and I ultimately took a job, he continued building that business. But we branched off each other's paths a little bit, because he continued to be independent. And when I left that company, he was just really excited for me and happy for me and supportive of me, and was my first client. And I don't know how intentionally that was. But I think he was probably, in some regards, trying to just show me that I could do it, because I hadn't actually just like, sold my time or expertise for money up to that point. And there's something really magical about being able to prove that you can do that. And so he was starting a podcast, ironically enough, and I was helping him to produce that show in the beginning and make a good show and, and get the artwork, right. Then I had another also friend from college, who also was supporting me in finding Funny enough, the sweater that I'm wearing is, this logo is the entrepreneurship organisation at the university, one of them. And the other guy was starting a company and he didn't know what to name it. So he gave me He gave me a project basically, to come up with some suggestions for names for that company. And I created this like really cool spreadsheet that I would take like a root word, or take a word, and then I would have that word plus the root of that word. And then it would add, like every prefix, you could think of every suffix, you could think of just like create some sort of variation. And then I would check and see like, which one of these is fun and makes sense. And seems like a good name, that's a good jacket, see, like, is the.com available the.co really, really fun project. But those guys have given me those projects really early on, as my freelancing I think gave me a lot of confidence that, okay, it's possible, people will actually just pay me to help them with things. And I could probably get enough projects like that I could make do. And at that time, I was still very much thinking that entrepreneurship was software. And so the idea was, I will just freelance enough to afford the time and space to figure out what is the next company that I want to build. And that never really quite happened.
Conor McCarthy 07:51
He never got out of the out of that lane, I guess. But you've built something, you've built many things that are definitely bigger than you than you in person. If that makes sense.
Jay Clouse 08:01
Yeah, well, I just realised that I could build assets that weren't software. But that could be leveraged in a similar way. Like, I could use that time and space to create podcasts, or I can use that time and space to create courses. And now all of those are assets that can sell. And what was beautiful about all this, when I was doing the first company or even the job that I had, as a product manager, I was working with a lot of designers and engineers, and to make the things that I wanted to make, I had to go through other people to ultimately create the thing. And it was very freeing to find that I could make content for lack of a better word. That was my vision, and I had total control. And I could make it real. And I realised that was what I wanted to do. Probably forever.
Conor McCarthy 08:51
Wow. Okay, that was to be a great feeling when you realise Oh, I can I can do this. And I can start and keep going and get better as I go and build things you've got, you've got a great positioning statement. After say, like on your website, it's I help creatives thrive as business owners. And I think positioning is something that when you're starting out as a freelancer can be difficult. Because, you know, as you mentioned, you you worked with some friends for your first couple of jobs and you did this one naming job. But you didn't ultimately end up doing that. So did you go through many iterations of I do this for this, or I do this for those people over there.
Jay Clouse 09:32
I'm still going through it. And candidly, like, I'll probably change that positioning statement in the next month. If you don't treat your freelance business like a business, you're going to end up working more hours and you've ever worked. You're going to be earning less than you've ever earned. And you're in a worse position, actually. And when you when you share that with people, usually they relate because like yeah, I feel like I'm working all the time. And I'm not happier. I don't have more time. I'm not making more. It's like well If we really looked at, you know, the rigour that you're putting into running your business, there's probably a lot of holes. In terms of prospecting and finding new clients, a lot of people wait too long to try to find new clients or create new projects. And they're in this constant state of like Panic of, I gotta find that next projects. And then they go into overtime, like working like crazy and talking to a tonne of people because they need to project tomorrow. Whereas if you have a little bit more rigour and process around your your sales pipeline, and even how you manage your finances, this can be much slower and more sustained and predictable. And give you that time that you're looking for. That is you're saying, You're saying all the magic stuff that I totally agree with? And but I also noticed like to be on the other side of that kind of going. They said like dirty words to me, but they are they are the business, weirdly enough, the projects and the clients and the relationships are kind of the the exhaust at the end of all, that of all the good planning and the good systems. Was there a moment where you, I mean, I don't I don't assume this came to you in a flash. But was there a moment where you kind of went, Oh, this is I got to pay as much attention to this as I do. The projects that I'm creating for the clients. Yeah, I ran out of money. My first my first year after I got out of MBA, and I started doing unreal, this accelerator that I was putting together, I started doing that. And I set up the model of the business that I would work with 15 to 20 people for a three week period, two to three times a year. And so it was very understood to me that if I have 15 to 20 people, that's going to cover my expenses, and that is good. But then I immediately need to start another cohort at the price that I'm able to charge to cover my expenses. Again, what I miss calculated was the calendar, actually, my first my first paid cohort that year was in the fall. And it wrapped up around October. And I realised there is no way I'm going to get 15 people to sign up for a 12 week intensive programme through Thanksgiving, Christmas, New Year's. So that model didn't work. And I ran out of cash. And I realised Oh, I need to find some projects. And I got lucky, another person that I actually had known for years from this club. I just chatted with people that were close to me. And this is, you know, spoiler a lot of how I got my first time customers, I had conversations with people I already knew who already knew liked and trusted me. And I felt comfortable being vulnerable with them. When I would ask, you know, how are things going for your business? And they would tell me, they would then usually say How are things going for you. And there's a point at the end of that year where I was just like, things are really good, unreal, went really well. But I miss calculated my own cash flow. And I'm not gonna go do another programme until January. So I have a couple of months here where I have time, and no cash coming in. And that guy hired me on retainer, and said, Well, I know you're good at this. And this because I've seen you do it, I love your website, I love the way you do email helped me rebuild my website, and how many put in some systems for my email, and taught me a couple things. One, the fastest way to find a new client project is to go to people who already know like, and trust you and you can be like, pretty open with and like, you can just have a much more honest conversation. And to if you don't watch your cash flow, and understand that we're how this is all gonna work, you can find yourself in a bad position really quickly. Like, I'm somebody who will often run at something. And I'll touch the stove to realise, oh, I shouldn't touch that stove. But once I touch the stove, I figure out how do I make sure I never touch that stove again. And I touched the stove of cashflow. And I hadn't realised how to never do.
Conor McCarthy 13:57
This type of cash flow might end up being the title of this episode. It's pretty, it's a great mental image. That is, you know, the know, like trust framework, if you like is is such a great one. And I think it's often approached or thought of in the sense of it's the trust piece really. It's like oh, I need to find people who trust me and what I do, but what you've just said, I don't think I've ever heard it expressed that light before you kind of went from a place of vulnerability and being honest and saying, You know what, I actually need work, which I think a lot of freelancers sounds like a needy statement. But in lots of cases that you'd have need to make the ask and that can feel scary.
Jay Clouse 14:37
And I wasn't asking him even specifically like, Can you give me work? I just felt like our relationship was strong enough that business owner to business owner, I could say, here's where I'm at. And he kind of filled in the dots actually of Well, I know you can help me with this. So I'll hire you to do that. The other thing that I like to talk about but haven't talked about in a while when somebody hires you It's because they believe you are elevated on like a skill spectrum from where they are, you know, I think of it like ladders against a wall. And each ladder represents some sort of skill. Maybe it's building a website or doing email. On those two ladders, I was a couple rungs above this guy, and he knew it. And he knew he could hire me because I would be better at it. There are a million ladders that he's higher than me, he's better at hiring, he's better at outsourcing. And I think a lot of times we we get kind of afraid to be vulnerable in these conversations, because we think that it's just one absolute ladder of like, Am I worth hiring? And we think like, why would this person hire me, they're so impressive. But chances are like, if you're ahead of them on a couple of these rungs, they would rather hire you, then try to invest in the time to get as good at that skill. So you can just basically say, like, I can do these things. And I know these relate to your business. You know, can we talk about that? Is there some opportunity here? And be kind of Frank, and if you know, somebody, you have a relationship like I had with this guy, you can be very frank. And that's very valuable in the beginning, because if he says no, I also would have felt comfortable to say, Well, why not unknown, he would have given me like real feedback. And that's hard when you're having like a first time conversation or just sending a proposal to a client. Useful, probably a good idea to try to do but that type of candour i think is positive.
Conor McCarthy 16:28
Hmm, yeah. That's fascinating. And did you ever did you ever reach a point with any client, where, you know, they trusted you so much that they keep giving you more and more work, which consultant which is great. But sometimes you maybe need to put in some boundaries or some guardrails to make sure that you don't end up spreading yourself too thin, or
Jay Clouse 16:48
most of my clients actually. Because, and this goes for both unreal, but even some of the freelance stuff that I did. I strive to just be the best freelancer, contractor person anybody ever works with like, and I'm thinking about it very holistically, like, I want to have the clearest communication, I want to make things the most efficient, I want to make as much of this relationship as possible just feel like magic, like it's effortless. And when you strive to hit those bars like that stands out, there are just a lot of people who don't follow through on deadlines, or the things that they say they're going to do. They're flaky, they're flighty, you can't, you can't like get a hold of them. When you are communicative. And you hit deadlines, that sets you so far apart, that people like want to hold on to you so strongly, because there's some innate amount of onboarding that goes into any type of work relationship. And if they hire somebody else down the road, they have to redo that onboarding, here's how we work, here's who to communicate with, here's like, our standards and our practices. Nobody wants to do that over and over again. So if they find somebody that they've already done the work of getting them up to speed, and that person delivers what they say they're going to do when they're going to do it. That is so valuable to those people. And we often underestimate, especially people who are doing that we often underestimate how valuable how valuable that is. And we could probably earn more if we recognised that as as valuable as it is because people would pay more to keep you around, than to go through the process of onboarding somebody else. And hoping the quality is as good as yours is,
Conor McCarthy 18:26
yeah, I love that there's probably a handful of ways that outside of the body of the piece of work you're doing that you can add 10 20% to whatever project you're doing, even if it's striving for such clear communication, or just just being on time, just being punctual. There ways to add value that are free, essentially,
Jay Clouse 18:48
yeah, we'd like to work with who we like to work with. So if you're somebody that people like to work with, you're going to be in a really good spot, you just kind of have to get your foot in the door in the first place. And, you know, we talked about this know, like and trust factor. These people are your advocates, whether they hire you or not people who already know you, who already like you who already trust you, they are your advocates, to people around them to themselves even. And it's so much faster, to go to your advocates first and see if there's a way you can collaborate. You know, I don't even think of finding clients as finding clients. I think of it as creating clients or creating projects, because I go to the people in my life that I feel like would be potentially good clients, because they're business owners because they're doing things that are interesting. And I have conversations with them to understand what they're doing, where they're going. If they have some challenges that are intending they're aware of, and if I can plug in and solve those challenges, boom, I just created a client project. They didn't have to go out searching for somebody, they didn't have to do any price shopping. They just realised Oh, I have a problem. Jesus has a solution. I trust Jay, I know he'll do a good job. Perfect. This makes it easy for me.
Conor McCarthy 19:56
Yeah, that makes that makes so much sense. I hope you're enjoying this Episode and that there's some actionable and insightful advice that you can take out to your business, helping you identify and create those first 10 customers is what I do. So if you like what you hear on this podcast and want more information, including a bunch of free resources on how to find your first 10 customers and grow your business, check out first 10 podcasts.com, that's 10 one zero, or find me on Twitter at the first 10 pod. Now, you probably hear what I'm about to say on every podcast you listen to. And it makes a really big difference to the show. If you find this podcast in any way useful or enjoyable, I'd be so grateful if you left me a review on iTunes, it really does make a big difference in terms of other people discovering the podcast. Also, if you leave a review, you will get to see your name on the review. In lights. What I'll do is I'll design your words and post them online attacking you on your project along with it. I know it's a pretty sweet deal. Okay, let's get on with the show. Just to switch tracks a little bit. You mentioned unreal collective a few times. Do you want to just describe briefly what that is? Because actually, it was the first time that we properly had a call where it's like, I remember reading about unreal or being damned, that is good to know, I was probably a bit jealous of it. I was like, Oh, I don't want to do that. So yeah, just take us back and just talk about the start of that
Jay Clouse 21:21
unreal collective was basically how I started freelancing. I had had a conversation with a friend of mine. And I was telling him that I was gonna quit my job, and I didn't know what I wanted to do. And he said, If I was you, and I had your network, I would facilitate mastermind groups. And I didn't know what that word was, I don't know what that meant. And I said, Tell me more. He said, Well, I'm a lawyer. And I meet with other lawyers a couple times a month for an hour at a time, and we help each other grow our business. And that sounds like fun to me. It's not like something I would be good at. It was at its core kind of a facilitation role, but also a little bit of a consultant role. And I thought, if people value that, I can definitely put that together. So the concept was I would put five business owners together in a group plus me, we would meet every week for an hour for a 12 week period. And at the beginning of that 12 week period, we would do a road mapping exercise where I talked about their goals I learned about about their business, we created like these four, eight and 12 week check ins through that programme out group people based on the stage of their business, the nature of their work, and their timing, availability. And we will do that we meet every week for an hour for 12 weeks. And I did that in groups of 15 to 20. Total, like a cohort was 15 to 20. People all this language is hilarious, by the way, because now with cohort based courses, this is like a very common sort of structure. And that wasn't really as much of a thing then like I came out of old MBA and realised Oh, is this similar to an MBA, I'll do something like that. But I worked with 15 to 20 people at a time in groups of five, for 12 week period. And on the back end of that anyone who had gone through that programme, I added to a slack so that we can communicate between calls between groups. And that became a little bit of a private community. And yeah, I did that for almost four years, that community and, and me as a person, were acquired by Pat Flynn and Smart Passive Income at the end of 2020. And now I'm leading community for Smart Passive income. But yeah, that was the experience. It's pretty incredible. And congratulations on being acquired. I think it's, it's not something you hear often about communities, or at least you haven't until this point, maybe we'll see more going forward. The you know, community is again, it's one of those words that's now in the culture. And I I still meet quite a few freelancers who along with the, you know, I need to have a blog and a podcast, I need to maybe write an E book. But I but there's a vague sense of needing to start a community. And I sometimes think it's because it's so common to hear Oh, there's a community here. It's a community there that people kind of go what it must be easy to start a community. What what's it like running a community J. tarde, it's exhausting. Because it's, it's a never ending. Like you're never done. You know, a lot of people are thinking that Oh, extra community because it's easy. And you think it's easy because the tooling exists. And the tooling feels easy. And it's like I communicate with people. And I have a tool I have access to if I put the two together, magical happen, it will have a community. And that just like could not be further from the case, in my opinion. You mean you could have people in a community platform, but until people identify with it as a community, it's not really one of those things until people are having continuous sustained interactions. It's not really happening. And so I think people underestimate the amount of work involved in starting a community and I can talk more about this, but I think people really, really underestimate the amount of work involved in starting a community and making it something great that people continue to return. And spend time investing in investing in and putting attention and effort into that platform. I think we're all a part, a part of many communities that we haven't checked into in a long time. And you don't want that to be your community, you want your community to be the one that people can't stop talking about, I can't help but visit. And that comes from a lot of intentional effort in cultivation of relationships and shared language and things like that.
Conor McCarthy 25:28
Hmm, yeah, it's part of more dead communities than alive ones, unfortunately, are a part of one or two, where the the person who started just rarely shows up, but there's a kind of a culture of helping each other. And it's totally fine. They don't need to be there. You know, they're not the rock star on stage, and we're all kind of waiting for them to show up for the gig, we're just happy to hang out with each other. And that's kind of great.
Jay Clouse 25:52
Yeah, when you get to a point where you are not the, the attraction, you have a great example here of like a rock star, if you're not the attraction, you are the curator, like my thought is, as a brand, or as a creator, you are basically putting out the signal that is bringing people to you, and they say, I agree with this, I believe in this, I align with this. And you've created this very specific segment of people in the world who have a shared set of values or beliefs. And you, you've just been the lightning rod to them. But the opportunity is connecting them to each other. Because people probably have a hard time finding people like them, that's why they followed you in the first place. And if you look at your role as community creator, after, you know, being a curator of those people, then you can create a really special place where you're building relationships between the nodes of your audience, and they will always attribute those relationships to you to your community. But you're right, it's not about you at that point. And it shouldn't be about you, if your community is a place for you to talk about you and essentially be another broadcast channel. It's not serving the right purpose, in my opinion.
Conor McCarthy 27:07
Hmm, yeah, cuz when the community is, is, is good, it's great. Usually, you know, it doesn't. So I was gonna say doesn't take a lot, it takes a lot. But the value that's created within the, my working communities is just incredible, proper internet, friends, people I may never meet in person, but that I know, like and trust.
Jay Clouse 27:25
Exactly. It's, it's, it's exactly what we've been saying, you know, this organisation that I keep pointing to on my dress was a community when I was in college, and you meet people through these shared interests through these shared sets of beliefs. And those become really strong relationships that even if they go dormant for a little bit of time, they can still be like, strongly reactivated ties, these people. And when you have this history, and this shared vocabulary, it's just a lot easier to be vulnerable, be open and communicate, have candour. And, you know, get to the root of things quickly, even if that is like maybe a potential project
Conor McCarthy 28:01
like that. We just talked for a second about balance, and not the kind of you I honestly don't know how you get everything done that you do, because you've got so much going on. But I suppose in the context of people early on in their freelance career, and they're trying to figure out, you know, what, what do I work on? I know, it's probably easy to kind of go, I'll go and set up an Instagram account, or I will build my website, or, you know, probably Unfortunately, the last thing is, usually I'll go and find clients, or I'll go and you know, work on my craft, how did you balance those things?
Jay Clouse 28:36
Well, there are some very tactical ways. I'm a big fan of theming, your days, and time blocking. So it got to a point where like, when I got groups, together for unreal, I always tried to actually have the groups meet on the same day of the week. So that if Wednesday was the day that I had unreal group calls, I could get in the headspace of nothing else matters today, I need to show up and make this a great experience for these people. And if and when that was true, or if it was two days a week, there would inevitably be a day or two where I could just say, I'm not going to take any calls through calendly. I'm not going to make it possible to book a call with me on this day. This is a deep work day for me to do this type of thing. And I basically would align that with the cadence of my content. You know, if I have a podcast coming out on Wednesday, which the time was upside and now I have one on Tuesday as well. It became a game of Okay, well, I'm going to have my interviews on Thursdays. And that's going to give me several days to do this. Even the days where I had calls. I don't do this now. I don't take calls in the morning, because that's my best creative time. And I can get two hours worth of work done in 30 minutes some time. If it's in the morning, because I'm just way more focused and I can get a lot more done. So it's it's really leaning into your energy throughout the day. You know, I think about energy management as important as timeout spend a lot of time and context switching drains your energy. So the more that you can have continuous contexts throughout a day, the more you're gonna be able to get done.
Conor McCarthy 30:12
I love that the themed days, that's really smart. So it's, you know, I've read deep work twice. Now, I think this is a great example of kind of putting it into action where you say no to everything that isn't that piece of work for the day, which is, which must be quite freeing in a way, because that's all you're doing.
Jay Clouse 30:31
Yeah. And I think I think we underestimate like how much you can get done in a week, if you just have a couple of things like, these are the important things to do this week, even when I was going through and hosting these calls for unreal, at the end of every call. We had a public accountability spreadsheet. And I would look at every single person and say, What are the things that are important for you to get done before next week on marking a spreadsheet? And then to start the call the next week? Let's say did you get that done? Yes or no and calculate a percentage of how well you're doing on the things that you're doing. And it forces you to distil you know, three to five things every week, and my list began to balloon because I got just really good at managing my time. But it does still like the five things that if nothing else, if I get these five things done, the business is moving forward. And it's not stuff like for example, because I knew that I was going to publish every Sunday a newsletter and publish every Wednesday, a podcast, I never put that on the sheet that was going to happen. It was stuff beyond the norm beyond the status quo, like build this asset, or finish this presentation deck, or reach out to three potential guests for the podcast, stuff that is moving forward and building on the business as the main like blocks for that week.
Conor McCarthy 31:50
I think that's, that's smart. Because it's probably easy to put in this stuff that you know, you're going to do already, but that decision has been made your you know, your decided to do that. So yeah, what's actually going to make a difference, which takes a little bit of courage. Sometimes it's like, Okay, I'm putting it down.
Jay Clouse 32:04
Like, start small, you know, if you don't have a system like this, and you're not as trusting of yourself as I am to hit like, content deadlines, put everything on there, like give yourself that magical moment of crossing something off your to do list, even if you know you're going to do it without being on your to do list, because that gives you momentum, it gives you confidence, you're implicitly training yourself that when you say you're going to do something, you get it done. By the way, if you're not doing that, you're kind of implicitly doing the opposite. If you continue to miss deadlines, you're continuously reinforcing to yourself that it's okay to miss deadlines, which becomes at least on a subconscious level, like a negative thing. I always find like, if I'm starting to slide, I will do something to psychologically wipe the slate clean and say, Okay, that was then we're starting fresh. And I am a person who hits my deadlines. And he said that mines that matter. And I just have to continues to prove myself because you need to earn trust in yourself that you're going to do the things that you're going to use a you're going to do on the timeframe that you're you're going to do it and that becomes such a superpower, because it will empower you to commit to things that you know are going to be good. And to say no to things that you know you don't have time for. Because you trust yourself to get done the things you're going to do. And if you commit to something that you don't have time for, and you miss it, that's going to change who you are to yourself into those people. A little bit of a rant there, Connor, but this is important to me.
Conor McCarthy 33:28
No, no, no, I'm sorry. That is I love a good rant. Because I think that's coming from a place as it's sobering, I guess like it's coming from a place of putting so much thought into actually how to advance your business and your craft and down to the nitty gritty of how you plan your days and your weeks. And you've accomplished so much from this, this system that you've outlined and it's it's kind of amazing it works and having having things like accountability and and everything you said it's like they are they're part and parcel of running successful business.
Jay Clouse 34:00
Totally. Yeah, time management, energy management, super important because ultimately, if you look at your calendar and you don't know where something on your to do list is going to happen. It's probably not gonna happen.
Conor McCarthy 34:11
So freelancing school if I attended free, let's go what I learned the magic art of producing as much quality content and quality courses as Jay tell us about free lead school.
Jay Clouse 34:27
freelancing school is my first set of courses that I continue to update and, and make even stronger. But it started from, you know, with unreal, I thought I was going to be working with a lot of startup founders. And what happened was a lot of freelancers and creative service providers were coming to me be as they realised I could help them get the business stuff in order for their business. Things like cash flow, budgeting, accounting taxes, but also marketing themselves to get more clients and selling themselves when they have those conversations. So I took every thing that I had been teaching for years through unreal. And I put them into three courses, business for freelancers, marketing for freelancers and selling for freelancers, to give you the toolkit, regardless of whatever service you provide, to better market yourself to sell larger projects, and to get the back office, operational stuff under control, so that you can actually have this time and income that you're looking for, as a client service provider, or Freelancer or contractor.
Conor McCarthy 35:28
And when did that kick off when to Freelancer School of start?
Jay Clouse 35:32
I want to say middle of 2018, maybe, or maybe it was even 2019. I think it back it might have been 2019. I think I started dating my now fiance. 20 2018. And we I finished, I finished this courses as we were dating, so it would have been the middle of 2019 that I started releasing them.
Conor McCarthy 35:55
Hmm, I love they're they're almost a holy trinity of freelance courses.
Jay Clouse 36:01
Yeah, you can, you can, you know, pick a pick or choose one of them. But there are a lot of people who do really great work teaching you how to be a better copywriter, or a better designer or a better developer. And that's not the lane I'm trying to play in. I just want to help you earn more. Put a business in place that supports the lifestyle goals you have, which is probably giving you more time whether it's creating digital products or content, or just spending more time with your family. So I made it agnostic of the discipline you're doing just to help you sell more projects earn more.
Conor McCarthy 36:31
I love that. And it's obviously drawing on your years of running on real and everything else that you're doing. I do recommend people check that out. It's exciting just to read about it from a freelance perspective. It's like, Oh, yeah, this is this is all the stuff that, you know, if you googled any one of these things you would be swamped with is seconds, and I've been that person. Whereas you, you've done a great job of I guess, kind of distilling down, let's say marketing for freelancers. It's like just that. I think it's really it's really great.
Jay Clouse 37:02
Yeah, I mean, all the stuff in those courses candidly, like, you can find resources and articles and YouTube videos to tell you all this information, probably pretty credibly and pretty well for free. But at the end of the day, like this is a very efficient, distilled way to go through this. So you can actually put it into place and get on with the rest of your life, get on with solid projects, doing the client work, things like that.
Conor McCarthy 37:27
Lovely big freelance enabler. Just as a final question, what would what advice would you give to someone who is just starting to find their first
Jay Clouse 37:35
10 customers? Start with people you already know, we've already talked about it, but start with your advocates. And even if they become a client themselves, is because they advocated to themselves that they should hire you. So always, always, always start with people who you already know and like, or who already know, like and trust you, because somebody has to know you exist, like you. And trust that you can get the job done if they're going to hire you. And so you might as well start with people who are that is already already true, then start from zero with somebody and build a relationship from scratch. chances are they're people in your life, who you could have a conversation with. And even if it's not them, who hires you, that can become a great source of referrals, a great advocate for you. And if they swim in the same pond as your potential clients, it's better just to make sure that they know that you're freelancing, that your coaching or consulting whatever you're doing, they need to know what you do and who you help. So they can effectively advocate for you when they have
Conor McCarthy 38:35
the opportunity. That is a great place to wrap up. Jay, thank you so much for imparting all that hard earned wisdom of love the show notes to include and I do recommend people check those out. A lot of them will be put in by to your website Jake lattice calm. Yeah, thank you very. Is there anything else you'd like to add any other places you want people to check you out?
Jay Clouse 38:52
Nope. Easy to find jayclouse.com is a great place to start or at Jay Clouse on pretty much every social media platform.
Conor McCarthy 38:58
Cool. Thank you very much a. Hey, thanks, Connor. Next time on the first 10 podcast, Peter Shepherd, unpacks imposter syndrome, and how you can use it to your advantage.
Peter Shepherd: It's really about what do you do with 10 you figure out a way to what I've talked about in the past is dance with it. And and sort of say give it a voice. You know, I see you I hear you. Okay, so I feel like a fraud. Interesting. And here's what I'm gonna do about that.
Conor McCarthy 39:23
That and more on the next episode of the first 10 podcast.
SUMMARY KEYWORDS
coach, people, podcast, realise, imposter syndrome, coaching, jen, freelance, skill, book, conversations, freelancer, business, pete, freelancing, pitching, imposter, talk, instagram, workshop
SPEAKERS
Conor McCarthy, Peter Shepherd
Peter Shepherd 00:01
I feel like most people listening to this podcast, they want to do interesting work. They want to challenge the status quo. They want to be constantly curious and learning and trying new things. Now in order to do that, one way of thinking about it is, I just need to put myself in situations where I feel like an imposter.
Conor McCarthy 00:20
Hello, listeners, and welcome to the first 10 podcast. I'm your host, Conor McCarthy. And in each episode, I interview Business Builders on their first 10 customers, who they were, how they found them, how they talked to them, and what effect they had on their business so that you can learn what worked and what didn't. When I'm not recording podcasts, I help Business Builders find their first 10 customers and grow their businesses. I do that through one to one coaching, and a series of online workshops. please do check out my website Conor mccarthy.me. For more details and to sign up to my newsletter. I hope you enjoy the show. My guest today is Peter Shepherd, Pete and I met while coaching Seth Godin salt MBA, and he was amongst one of the first people I ever used the phrase internet friend about. We started our coaching practices about the same time, and we've had many, many conversations over the years about tackling the various strands of what it's like to be a freelancer. We've thrashed a lot together, over zoom and in person sometimes. And the results of those thrashings are right here for you all to hear today, Pete website says that he quote, helps leaders develop, grow and create change, unquote. And Pete definitely does that every day in so many ways. And on this podcast, he talks about his coaching methodology, including asking good questions, holding space, listening deeply, and generating trust. We talk a lot about the business end of running a freelance business and why it's so so important to get your head around that as soon as you can. Beat also details breakthrough moments on his early coaching path, including meeting is now collaborator Jen Waldman. He talks about experimenting with pricing, understanding his imposter syndrome, and also helping others do the same. And what he learned from his experience of moving from the corporate world to the freelancing world. Pete Shepard, thank you very, very much for taking the time to be here with us today.
Peter Shepherd 02:49
Thanks for having me, Connor. I'm very, very excited to be here. You are podcast host extraordinare. You're human Periscope. You're a freelance. You're a lot of things. But we first met. Doing the alt MBA is five years ago that we met, maybe five? I think it might be close to five years. Yeah, yeah. And even though you're based in Australia, we actually managed to beat a couple of times in person in the US. But when we first met you like me, we're also starting it as a coach.
Conor McCarthy 03:19
So do you want to tell us about that transition from what you were doing before into becoming a freelance coach?
Peter Shepherd 03:23
Yeah, yeah, I can give you the the quicksort story, it was a you know, long and arduous journey, as as a lot of these often are. But I, I, having taken the old MBAs a student was asked to point us back to be one of the coaches in the in the team. That's where I met you and a bunch of other amazing guests that have been on the show. And this weird thing kind of happened where I started to, I guess, have imposter syndrome around just the idea or the word, coach. And that framing of the skill set that we show up with in the NBA in particular. And as I got more and more into the workshop that we were coaching at the time, when I first met you, I eventually started to realise that the skill set required was actually the same skill set that I'd shown up with for the last. At that point, it was the previous six or seven years in a startup job that turned into a corporate job, working as a client relations manager, which was really around asking questions, holding space, helping clients solve problems, helping leaders in particular, create cultural behavioural change based programmes, like that was what I was doing full time. And I started to realise again, that long story short, I started to realise that same skill set can be used and is used as a coach. And so the more I sort of started doing it and getting more reps, the more I started to wonder, what would it look like if I did this on my own instead of doing this through this company that I was working for at the time and so that that was Like a very succinct summary of a very long arduous process over months and months of like, Can I should I will I want to die? How do you even start a business? What does it even look like? But yeah, this the short summary was I realised the skill set was very similar.
Conor McCarthy 05:12
Hmm, that's really interesting because a lot of a lot of freelancers start out by taking a skill or a set of skills they have and deciding that they can package those up and market them elsewhere. But you, you had a catalyst, maybe it was alt MBA, you know, maybe it was the like, the kind of the career path, you were on that moment to the career path. Was it difficult to I don't want to make it sound like a shopping list. But was it difficult to kind of put down on paper? Right, um, I've got to be a coach, and I'm going to, you know, here are the skills I'm going to bring. Um,
Peter Shepherd 05:47
I think it was, it was, it was less methodical than that. I think it was kind of this process of discovery as I coached leaders through that workshop. And then eventually what happened, I'm sure we'll talk about there was one particular catalyst catalyst, who is now my dear friend and podcast co host. There was this like series of events that kind of unfolded for me, that was experiential, as opposed to methodically listening skills. It was kind of a series of experiences that made me realise like an aha moment of, Oh, this is what you've been doing for six years in a different context. It's just packaged up slightly differently, and you're working with different people, and you're doing it in a different way. But the idea of coaching, you know, asking questions, holding space, being curious, opening doors, turning on lights, whatever metaphor you want to use, is a is a skill set that I recognise that I guess, as a curious human being I'd had for a while. So yeah, I guess to answer your question succinctly, it was experiential. As an aha moment, less and more so than it was like this methodical here are my skills. And this is what these skills could equal.
Conor McCarthy 06:54
Okay, yeah. They kind of reveal themselves over time. I like that. Exactly. Yeah. And I've watched you over the years, talk about and work on these skills, and it's amazing to see you it is your craft. You know, is there a Is there a way you think about how you work on those skills? Or is it? Is it the kind of putting in the reps with with coaching hours? Hmm,
Peter Shepherd 07:17
I think it's, I think it's perhaps both like, it's definitely reps, definitely reps. But what I've realised over the years is, the reps come in so many different contexts, when I started to realise when I launched a blog and started a podcast and started doing some speaking and started running group workshops, and like all of these other things. And looking back at my history, like we mentioned, I started to realise that the skill set of asking questions of holding space can actually be practising all of these different contexts. So I think about a really great podcasts, the hosts, usually, like you're doing now asks great questions, and then hold space for the people to respond. That's a pretty similar skill set to a coach. So it started off as I need to do all of this one on one coaching. And then eventually I realised, this skill set of being curious can be practice can be honed, in many, many, many different contexts. And as someone who likes to like try different things, and pick up different things and experiment with different ideas and formats, that really appealed to me, as someone who's going to try different things. So I sort of realised that over the journey as well,
Conor McCarthy 08:25
that's very good. I like that it's kind of meta, but it's a really, there's something kind of simple about it as well, which which makes it easier for you to go, Oh, this, this applies across the board. In a way you're always coaching, no matter when you're putting yourself out there when you're having conversations.
Peter Shepherd 08:40
Yeah, it was it was quite a quite a relieving realisation, to be honest, chronic, because I think in the past, I'd had certainly when I worked in corporate and startup and that kind of world was almost like I had two different selves. And I feel like I feel like I've heard this echoed through many people where, you know, you have your work self in, especially in a corporate job where you show up, you punch in and you kind of you behave in a way that is kind of in alignment with a corporate company culture. And then you kind of have this other like a little bit for me, it was like this little bit more rebellious self where I want to read these interesting books and challenge these ideas and asks these questions. And, you know, what if we did things this way, but it never quite fit into the corporate structure. And so it was kind of like exhausting having reflect to the personalities. And the beauty of eventually getting to this place where I realised that the same skill set can be practised across multiple disciplines was basically Oh, he had to show up as the same person no matter where you are. So if I'm coaching a leader one on one, I can finish that call. And then 10 minutes later hop on a workshop with a completely different group of people. But the same principle applies, I need to ask questions that are you hold space, I need to see what the leaders in that room you know, struggling with, which was quite relieving to not have to like tasks, which is much like that.
Conor McCarthy 09:58
And you How did you Think about your positioning as a coach. Because you know, it's important that when people come across your work, that either they feel that, you know, oh, pizza guy or also go, he's not my guy, which is totally fine as well. How did you and I look, this is an always evolving thing, of course. But like and we've had conversations in the past about how did you how did you think about it, you actually have a great kind of nickname phrase, if you like to talk about that. You made a human Periscope, you wouldn't have a periscope. That's it?
Peter Shepherd 10:29
Yeah, yeah. Which I sort of stumbled across after a conversation with my friend jen wallman, who I mentioned, I think earlier. And she kind of realised in doing this, you know, Simon Sinek style wire discovery that what you ultimately do as a coach, or as Pete is help people see things they can't, we will kind of like looking for a metaphor that, that or a symbol, I guess that speaks to that idea of helping someone see something that they can't quite see just yet. And the random story, there was my very first blog post ever, I actually refer to myself as a human Periscope. As a bit of a like side, you know, as a bit of a joke. It's a bit of a joke. And so that was the the story behind that. So having that helped, as like, Okay, I'm someone who helps people see things I can't. However, I will say like, I've really struggled. And I think still a little bit, but I'm getting a lot better at the whole positioning thing. And I remember actually getting, I think I reached out to you and was like, Can we have a chat about this? Because you're someone that I respect and admire who talks about their work in a really great way. And we, we probably bonded over the thrash, like, how do you? How do you do this? What do you say? So I don't know if I did a great job of it. To be honest, other than I had that, that like simple that metaphor of when in doubt, I say, okay, so it's like a periscope, you know, you can see things that you can't, and most people were able to kind of grasp that. I think what I was lucky to get access to, which is, you know, again, just been very much a place of luck has been a lot of word of mouth at an at an early stage, which meant that the pitching, if you like, in air quotes, was a bit easier because I came through my first few clients came through trusted sources via word of mouth. So there was less friction of like, Who is this guy? Why do I need to talk to this guy? So I was very lucky in that sense, I think,
Conor McCarthy 12:30
to to talk about those those moments. Because again, I know you so well, that I kind of saw saw it happening. And it's very, it is a very unique journey. But But let's get into it, because this is firsthand. And this is this is how you found your first 10.
Peter Shepherd 12:44
Yeah, so the I guess I hinted at a few of the things along the way. But essentially what happened is, having coached the old MBA and met you met a bunch of other brilliant people. One of the students that I was actually lucky enough, fortunate enough to coach was this lady by the name of Jen woman. And her and I had a one on 120 minute call, where she would say that she had sort of trajectory of how she was thinking about her business. I would say I was feeling like an imposter. And I just showed up and asked a couple of questions. And what transpired as a result of that was, it's kind of mind blowing to look back on it. But basically what happened is Jen said, Oh, once this workshops finished, can I hire you as a coach? And at this point, I was still working at a company. And I was like, Huh. And this was kind of the catalyst to kind of jumping around in terms of chronology, chronology. But this was the catalyst for me thinking, Oh, the skill set you've had for four years. It's a similar skill set. So she got me into this frame of mind of, okay, so if someone else wants to hire you, as a coach, what would that look like? And she very generously said, like, this is how I think it could work. I want to chat to you every month, and I want to pay you and let's talk about what that would look like. And I actually intentionally I haven't really talked about this, but I intentionally made the decision not to charge Jen money, but I decided, based on a few ideas that I could get paid through other means, like, practice, experience, a case study, maybe word of mouth referrals, maybe some testimonials, and all of those things became true. So having worked with Jen for like three months, then it became let's do a fortnightly call, then it became let's do a call every week that it became these like, three hour conversations. And which led to a whole different series of conversations, but but through that process, what I was able to get was obviously experience and confidence in coaching others, which then helps me talk about to your point, this idea of human Periscope, and what does that look like and helping others see things they can't Okay, and who were the other groups I could serve? And so it was really weird in a way because I was coaching Jen, but was getting so much out of that experience, it was almost like she was coaching me in reverse. And eventually it got to the point where I left my job. And I remember still remember this conversation as one of the calls with Jen, I was so nervous. In the last like five minutes. I was like, oh, before you go, you've said to me a few times that I should do more of this coaching for other people. So I was just wondering if you know, anyone that wouldn't fit that mould? Could you let me know? And she was like, of course, like, that was the domino she sent she sent an email to I don't know how many people it felt like 100. And because you know, the first like, four emails feels like you get 40 emails, you're like, Oh, my God, I can't believe someone wants to talk to me about doing this thing that I just decided that I would start doing more of. And so that was the that was the catalyst that was where the word of mouth started to come from.
Conor McCarthy 15:50
Hmm, that's really, really addressed to you. Like, you really did look at with Jen. Like, she's, she's, she's a wonderful person. And but I suppose the really interesting thing in there, is that your nervousness about asking, you know, totally, do you mind introducing or just telling people? Yeah, I totally get that. Did you? Had you ever kind of made it clear with Jen, that, you know, in other ways, it would be great if, if you could, if she could help you to kind of start your coaching career? Was that the first moment that she might have gone? Oh, yeah. Pete, Pete wants to get more clients? No, I
Peter Shepherd 16:30
was, I was pretty upfront with her. Because she kept very generously saying, How do I pay you? Where am I paying you? What's your fee structure? And I was kind of like, it's okay. Let me try and figure this out as a thing, basically, okay, as how I might approach this, like, I don't even know if it's gonna work, I really enjoyed this conversation. So it was pretty transparent. I think she knew that I was, I was kind of dipping my toe in the water as to what it might be like to be a freelancer, really. And I think knowing Jen's wisdom, she saw that. And I think she probably also thought, even when he feels the need to ask for my help, he will ask for my help. And, and she was right. That was that was eventually what happened.
Conor McCarthy 17:12
And were there any other first 10 customers in those early days that stood out in terms of where they came from? Or, or even something you did that, you know, was more, I suppose intentional, we kind of went, Okay, I'm gonna, I'm gonna go out and sell my coaching services. You know, and there is going to be a financial transaction. And there's going to be a proper, like a proper kind of setup if you like.
Peter Shepherd 17:39
Yeah. Yeah. So it's funny because the, the getting the email and the word of mouth was one thing. But then I knew what would come from that was potentially the conversation around. So what does this look like? How much do you charge? And what is this practice? And like, what does it look like? So it was kind of like, it was really exciting to get this word of mouth, conversation starters. And then on the rabbit hole of what happens next, how I still haven't quite solved how I structure this. In terms of like, in particular, around financials, I think a lot of freelancers. I know you and I've spoken about this a lot of like, the thrash and the confusion of pricing and value and worth and all that it's like a quite a hard nugget to, to wrap your head around anyway. And I remember I, at this point, I listened to so many books, listen to 1000s of podcasts, you know, all that freelancing and pricing and how to how to value yourself. And I think I probably went too far. I distinctly remember a few conversations that I, you know, because it was a lot of a lot of the marketing that I consumed, at least a lot of the content I consume was around, don't undersell yourself, don't undersell yourself, don't? And I was like, Alright, well, I'm not gonna understand myself. So the first conversation was kind of like, it's this match. And they were like, Whoa, that's a lot of money. I was like, Okay, good feedback. Interesting. Yeah, yeah. So the first few conversations, while they didn't end up, they didn't actually end up turning into clients, I was able to get a lot of valuable feedback and signals from the market, through even being able to have those conversations and propose those things. And so what that eventually taught me was, you know, pricing structures. The way that we can orchestrate an agreement as a freelancer across any industry is like an experiment and it can change and you can flex and you can decide to structure things in a way that you believe is appropriate at that point in time. And so I was a bit I think I was a bit too consumed by the lack 20. I went from like, not charging Jen anything to like, okay, so you have to charge I mean, it wasn't that much, but in my head, it was like you have to charge a certain amount and it's got to be a good amount of a lot of money because you don't want to get sucked down the tube of selling your time for nothing. And in the end, the feedback was like, that's probably a little too sweet. Pull it back.
Conor McCarthy 20:02
Really, really interesting idea. It is an ongoing thing. But I think what's really interesting in there that you said, it's like you may you kind of made small bets, you had coaching conversations, and you put a price out there. And that always, that always feels weird, especially when you're starting off like, Okay, how much does this cost? Silence kind of a number said further silence. What happened? What happens in that silence? Actually, ad? How do you treat that silence after a number
Peter Shepherd 20:29
of time? I think, yeah, I guess the thing I didn't say that I hear back in what you said, which was definitely deliberate was my my strategy, if you like, in air quotes of getting around pitching was to demonstrate the skill if you like. So instead of pitching people on what it feels like to be coached, I would just coach people for it. Like I would do an hour and a half initial calls when I started. And just basically just coach the crap out of someone for an hour and a half, ask questions, say, How can I help? Where do you need me? What what are you working on? What does that mean? Have you thought about this? What about that? And like, at the end of the 90 minutes, I was like, Whoa, so what does this look like moving forward? Like, how do you structure coaching? And I was like, Oh, it's basically what we just did. So I guess, I guess I yeah, my pitch was show that like, do the thing. And I found that to be I can't remember where I got that nugget from it was definitely from a resource. But I found that to be it might have been the book called The prosperous coach, which is a strange title, but a really, really good book, I highly recommend it. And, yeah, and basically, instead of pitching demonstrate by doing and that, as someone who cringes a little bit talking about themselves and pitching again, in air quotes, I really liked the idea of just do the thing, and give them the experience, and then let them decide.
Conor McCarthy 21:52
Yeah, I love that there is because there's so little strategizing, if you like, you know, in the sense of you're kind of not sitting there going, What do I say? What do I not say? What do I hold back? what's what's part, what's part of the quote, unquote, package? And what's part of this discovery call? And like, I'm not a huge fan of those words, but they can be useful labels at times. But But your approach, which I think, again, it's kind of simple as in, how about I just coached this person out at the end? If they're like, wow, this is, this is brilliant, then the conversation about money is like, now you know what you get? There's no, there's no hidden three point plan that's going to show up in a PDF at a later stage that you're kind of going well, what is that? So you already know what you're getting? I think that's really smart.
Peter Shepherd 22:38
Yeah, and I wanted to always be, I always wanted to be approached to be one rooted in generosity. And, you know, obviously, trust and openness and transparency. And I think that there was no expectation and I would say this, if, if you've got enough out of this hour and a half, and you don't need any, like, you'd never want to talk to me again, that's okay. Like, I think that that there was some level of Yeah, generosity and, and while it was I also found a just an easier way of, to me it was like this is easier than pitching, I would rather coach someone for an hour and a half and half the pitch.
Conor McCarthy 23:17
Totally. I hope you're enjoying this episode, and that there's some actionable and insightful advice that you can take out to your business, helping you identify and create those first 10 customers is what I do. So if you like what you hear on this podcast and want more information, including a bunch of free resources on how to find your first 10 customers and grow your business, check out first 10 podcast.com, that's 10 one, zero, or find me on Twitter at the first 10 apart. Now, you probably hear what I'm about to say on every podcast you listen to. And it makes a really big difference to the show. If you find this podcast in any way useful or enjoyable, I'd be so grateful. If you left me a review on iTunes, it really does make a big difference in terms of other people discovering the podcast. Also, if you leave a review, you will get to see your name on the review. In lights. What I'll do is I'll design your words and post them online. I'm taking you and your project along with it. I know it's a pretty sweet deal. Okay, let's get on with the show. How do you manage your marketing? that's a that's a big question, I suppose, you know, how do you how do you go from your coaching and your clients and things are going well, to ensuring that you know, in future, you don't hit this point, this kind of the low end of the roller coaster where you're like, Oh, actually that work has dried up and I have nothing coming down the pipeline. Is there a way that you try to maintain momentum with your marketing?
Peter Shepherd 24:46
The Freelancer cycle I call it I feel like I go through that dip. Still a lot. That dip of i think i think they speaking as freelancers we love doing the work like I just describe to you for 10 minutes how much I loved, even when I wasn't getting paid doing the coaching call, because we love doing the work. Regardless of what the work is, as a freelancer, what we don't like, in my experience is working on the business. And your friend that is marketing is that what does it look like to set yourself up your future self up to have more opportunities to continue to do the work? That is really hard, especially when the works in front of you? And you're like, oh, but I have these clients, and I'm working with them. So what do I need to worry about? And I've gone through many, many times, that moment of like, oh, oh, when this when this contract finishes up, or when this project finishes up, what is next. And then you kind of swing into a bit of a panic. So I don't know if I have a perfect system for that. In fact, I know I don't have a perfect system for this. But the thing that I always really liked was, firstly, just the mental model of getting clear on those are the two things, doing the work versus working on the business. And once I had that distinction in my head, I was like, Okay, cool. So I need to make time for both of those on any given day really. But particularly on any given week, I try and look at structuring my weeks in a way to be I've done some work on the business, and then I've done the work itself. So that is a mental model has been really helpful. Now what that actually looks like very tactically, I've, like experimented with various things, whether it be I mean, I have a podcast. So I like to think that in some way that's, that's putting the experience of working with people out into the world, which is creating a change in someone because we have some listeners. And so that, to me is a form of marketing. It's a little less direct, which I kind of like to be honest. And and then, you know, I have a blog. And so I guess there's a bunch of there's a bunch of content that I do each week, which I consider to be on some level working on the business. And yeah, maybe I'll just pause there, but that that mental model in particular has been really helpful. Does that make sense?
Conor McCarthy 26:55
No, no, it's huge. And this is like, we talked about it before we started recording like I'm working on this. This accountability group called the freelancer marketing cabinet at the moment, and it came out of the realisation from another coach friend, Amir was talking to him about this exact problem. And it was like a, you know, freelancing in your junior thing. And he was like, well, your job is really to, to freelance is to sell your freelance services. And that was and it was like, Oh, that's, that's the reframe I needed is like, because yes, we love doing the work. But there will be less we tell people that this work exists. That's really good. Yeah. And it was one of those things that probably applies to everything I remember even back in my kind of festival days when, like we quite a successful festival in Irish terms. And other people who wants to start festivals came to a saying, oh, help us start a festival. And my first bit of advice was always like, what, how are you going to run the business? Because it's, it's great to want to start the new festival of interesting hats, or whatever it is. I heard all kinds of ideas professionals back in the day. But how are you actually going to market this? What about your cash flow? What you know, how are you going to set up the company? Oh, super boring back office stuff. But without that stuff? Unfortunately, your interesting hat festival is not going to go ahead.
Peter Shepherd 28:17
I think I think I probably needed you at that point. Because I don't think especially when I started, I did not do a good job of this. And I was very lucky, very fortunate that I was able to scrap and I've made it work. And that's for I think there's a few reasons in particular, one of which was Jen. And the other, which I think was being lucky enough to be involved in the alt MBA meant that in any given quarter, because we'd run the alt MBA four times a year, I knew I was going to have the opportunity potentially to coach so I had some sort of add some safety nets, I guess. But I definitely didn't start off with a really solid marketing plan, like like your friend.
Conor McCarthy 29:01
One thing, actually, while we're talking about marketing, you know a lot of freelancers, when they start out, there's this feeling that I need to be on social media, I need to know I need to have a podcast and he tell a blog. And all of a sudden that the body of work, that body of work alone becomes immediately overwhelming. And I find it often it's unclear. The who's the for what is it for around that. What would you say about people who are in the thick of that kind of confusion? Yeah, I
Peter Shepherd 29:35
mean, I'm sort of right there with them. In that. I have. I'm denied and hemmed and hawed about what to do about social media and the like. I can't, I can't say that it's not effective because I think there are plenty of examples of people who've made great businesses and great freelance Careers Out of really great social media. My experience has been one where I've found more benefit, and certainly more joy, which is maybe the more important thing from my perspective, I've gotten far more joy out of focusing on content that is a podcast, with a friend and content that is a writing practice, which is a blog, which I really enjoy. And I fairly intentionally made the decision to focus my energy there. And yet, even even still, I sometimes find myself like, oh, maybe I should do a little bit more content on Instagram. Because the lure is just, it's just like, I mean, it's literally programmed to be there. So I have a very odd and confusing and slightly anxiety ridden, slightly anxiety inducing relationship with social media. You know, I don't love it. And I recognise I've, there's been some value I've got from it, like I have got a client from from Instagram before because someone else posted about me. And so I recognise there's like some level of value in that. But I've, I've chosen not to really opt into marketing my business that much through Instagram.
Conor McCarthy 31:06
Yeah, this is that that's really good advice. One thing you said in there was the word joy. And sometimes there is that feeling of, Oh, I think I should be on Twitter. But oh, I just really don't like it. And that's like forcing yourself in to squeeze into a platform shape is obviously not the right thing to do. But is there I suppose the scarcity mindset of but there might be business for me over there. I think joy is a good word maybe to, to hold on to and thinking about that. There's the idea of kind of being comfortable in your in your chosen platform. So podcasting and writing, are two you mentioned is I think, really important. Because if you're gonna have to show up at whatever platform it is, and do it consistently and get better at it, then pick something you're happy to do that it I guess.
Peter Shepherd 31:59
Yeah. And I think the other thing is it. The there are various platforms that suit certain skill sets, so certain free careers. So like, if you're a photographer, I imagine I'm speaking at a school, but I haven't Well, I have a bunch of friends who have freelance photographers, and they have unbelievably beautiful Instagram accounts. Yeah, yeah. And I imagine that's quite a smart use of their skill. If you're a speaker, and a coach and a workshop facilitator, like, Is it important that you can post a nice photo on Instagram? Not really, it's more important that at least the story I've told myself, so I can avoid social media, is that it's more important for me to be able to make assertions, ask questions hold space, and what's a good platform for that a podcast? And what's another good platform for that writing? Because you get to think out loud. So I think looking at the skill set of a particular freelance job, might actually also help determine Where's a good use of your energy?
Conor McCarthy 32:57
Yes, yes, totally. And considering your your ideal customer as well, like, where are they going to hang out? You know, like, if if you coach C suite execs, let's say, like, very, very high level management. What are the chances of being Instagram, what it has to be on Twitter? What the chances are going to be a LinkedIn much higher? Or, you know, what are the chances that they will read blogs about management plus coaching, you know, sort of kind of almost reversing yourself that way into it. And some people just aren't on social media, you know, let's say elder generations, etc, I find people are they're like, No, I just rely on my friends and my network. So the only way that they're going to buy a freelance service is they're going to call their friend and say, Hey, do you know anyone who does coaching,
Peter Shepherd 33:43
I love that one of the most useful exercises I ever did was listing out I'm trying to remember where I got this, there might have been the freelancers workshop on the akimbo platform, listing out the last 10 things that you purchased through a freelancer and then looking at how you came to make that decision. And I when I remember, when I did this, I think nine of the 10 were because someone else told me about this company or this thing. So it was, so I was like, for me, word of mouth is basically everything. So if someone is trying to market something to me, and they're trying to do it through Instagram, like using myself as the as the subject, they're gonna have very little luck. But if if they get to a friend of mine, and a friend of mine tells me about it, they're gonna increase the likelihood a lot. So I love what you mentioned this like, empathetic shock. I like empathetic marketing or framing yourself in a way that is empathetic to Who are the people I'm trying to serve? One of the platforms they are on. Okay, cool. Let me go there and help them make that decision.
Conor McCarthy 34:42
Yeah, yeah. Who is it for? Always? That's one of the things you and I have learned at a deep level. Yeah, shocker.
Peter Shepherd 34:50
Every day you realise it's still it's still there. It's still really nice.
Conor McCarthy 34:54
Yeah. Your your podcast with Jen. The long the short of it. is one of my favourite podcasts, I really, really mean that I was actually listening to it this morning before this. So I've got a recording of Pete Shepard, and I constantly take notes on it or listen to episodes twice as I think it's really great. What's interesting about it is you kind of go a level deeper on money topics. So you'll pick even sometimes it's even you'll pick a word like failure. But you'll really get into that. And one of the things that's come up time and again, I'd love to ask you about is imposter syndrome. And don't talk for a minute about what imposter syndrome looks like for you. And how do you coach people around that? It's funny,
Peter Shepherd 35:35
I think one of the reasons I really like thinking about or talking about or unpacking imposter syndrome is because I just realised that so many experiences that I've been fortunate enough to have, have been kind of the epitome of being an imposter. And I feel like every time I put my name in one of those situations, I feel like an imposter, like a fraud, like a fake like a phoney. Like you don't deserve to be there. And this goes right back to you know, being nominated school captain in grade six. Like who the hell am I with school captain in grade six, or my first internship, while I was still at university, I got to work for the state government. And one of the jobs that we had was looking after Prince William when he came to visit Victoria and like, Who the hell am I and his one year old, Shaggy haired kid with braces, you know, and a suit that doesn't even fit me and I'm here I'm with like, Prince Woot. Like, I just feel like I'm the definition of an imposter in so many different ways. And, and so I get really interested in thinking about that. And, and something that Seth Godin actually said, which really started to resonate with me was like, this is a feeling that is universal. And this is a feeling that comes about when we're doing something that we've never done before. So actually, by definition, of course, you're an imposter because you're doing something that you haven't done before. So you can't possibly be qualified, or you can't possibly have known what it's like to work with Prince William or if it's the first time you're writing a book, it's the first time you writing a book, you can't you can't be a qualified author, the moment you start writing your first book. And so he kind of frames it as outside of, you know, surgeons or lawyers or people who genuinely need a certain hard skill to do a skill to do a thing. A lot of these real human softer skills or leadership positions, if you like, or opportunities even or freelance careers. The kind of imposter syndrome that we should look for, and actually use as a compass, which is the moment that you are going to learn something new, grow and do work. That's interesting, because I feel like most people listening to this podcast, they want to do interesting work, they want to challenge the status quo, they want to be constantly curious and learning and trying new things. Now, in order to do that, one way of thinking about it is, I just need to put myself in situations where I feel like an imposter. And, yeah, I mean, I could talk about this for hours, I've spoken a TEDx about imposter syndrome. And like you mentioned, Jen and I talked about a lot in our podcast, but I think it's a useful, a useful frame for thinking about growing pains. Like this is a part of me growing and learning something new. And I actually think that you don't get rid of it, you don't crush it, it doesn't go away. That the, between those who I guess, fall down to imposter syndrome or or or succumb to it versus those who move forward. It's really about what do you do with it? Can you figure out a way to what I've talked about in the past is dance with it? And and sort of say give it a voice? You know, I see you I hear you. Okay, so I feel like a fraud. Interesting. And here's what I'm gonna do about that.
Conor McCarthy 38:44
Right. Yeah, that's great. Thank you. Thanks for sharing that. Because, again, you talked about a lot and even you mentioned Seth Godin on your good Seth was a guest on your was the first and only so far. guest on your, on your podcast. He said something that Jen picked up on he was like, he felt imposter syndrome still feels that what is launching a new project. But what Jen pointed out was like, Yes, but he's also the pioneer of so many takes, that that the imposter syndrome means you're on the path to becoming a pioneer net. Nothing that you know, not capital P pioneer, but just you know, you're creating something new. You're leading the charge here.
Peter Shepherd 39:21
I think but capital P pioneer, you can't be a capital P pioneer without having been an imposter at some point. So it's like, it's like it's an it's a necessary part of that journey.
Conor McCarthy 39:32
Mm hmm. I love that. You're, uh, you're you mentioned earlier, you've listened to a lot of audio books. I know you read a lot. We've read a lot of say books, any books that lead for you that have helped you on your freelance journey? I know you mentioned the prosperous coach. That's definitely going in the shownotes. It could be about the business of being a freelancer. But it can also be about you know, how do you understand people or yourself better?
Peter Shepherd 39:59
I mean, I could Talk about favourite books all day. I think freelance specific I did mention the prosperous coach. And it was I mean, for me, I think this would apply to a lot of freelancers, regardless of whether you want to go down the executive or leadership coaching path, or whatever it is, is a super helpful book really practical, really tactical, quite contrarian, which I always appreciate. The other one, like specific to the industry, or the world of freelancing that I actually really like, was a book called The wind without pitching Manifesto. I think that's what it's called. Yeah, not so obviously heard of it. That's it. That that I found, at a at a really important time, I think was probably when I was going through one of those dips of the freelance cycle of like, Where am I next few clients coming from? And what are the next opportunities and projects that you've been building? And I read this book that when without pitching manifesto in it, it really, it really, really resonated with me.
Peter Shepherd 40:56
I'm trying to think if there's any others off the top of my head that I mean, I think they're the two specific to freelancing in terms of like impactful books over the journey. I can, I can now many, many, many, you know, the audit possibility and steal like an artist with were really, really profoundly impactful for me at the right moment. And yeah, I guess I'll just go with those because I could just list books forever, otherwise, everyone will have a list of hundreds of
Conor McCarthy 41:24
diverse dead books. So just as a last question, I always ask, you know, what practical advice would you give to someone just starting out to find their first 10 customers? I think,
Peter Shepherd 41:40
I guess a couple of things. One is, don't feel like you need to quit your job to start a freelance career. Because I feel like that gets romanticised and talked about far too much. And I think about this six months, almost that I worked with Jen, on the side of working a full time job was so profoundly helpful. Because it wasn't the pressure of having to make it my career or pay the bills. And so I had the luxury of being able to say I won't charge and I'll learn from the experience. So I think that in particular, and other advice, I think, I would say, figure out a way, or try and think about a way to serve folks through word of mouth. And that the first, the first 10 in particular, I think they're probably closer to you than you realise. And this in my experience goes hand in hand with something like social media where you think you need 1000s of followers, because there's, there's more chance of getting the 10. But I actually think if you look at the inner circle, like for me, it was January help me get someone to help me get this person to help me get that person before I even looked beyond that little tiny network that I had. So I think like I think I don't know what the actual nugget of advice is other than like, look closer to your inner circle than you may think. For those first few.
Conor McCarthy 43:15
Yeah, I love that. Coming from a pro come from an expert. That makes a lot of sense. You know, it's not it's, it's something that quite a few people have said, because I think starting out as a freelancer Yeah, you need to, like where do you go this? What do I do, but literally just sometimes I've I've coached people, because they're ready to get your phone out, we're just gonna go through your phone. And it's amazing. You can get 10 or 15 names or like I would, I would happily call that person to talk to them about my new business or to see if they know someone who needs my new business. It's like, it can be that easy.
Peter Shepherd 43:47
Yeah, and I think that last point is really important is the tent. These these people that you identified don't have to be the customer per se. But they might know someone who could be the customer. So I think that's a totally, I love that, like pull out your phone and just look through your contacts. There's probably 10 people in there that would be willing to help you.
Conor McCarthy 44:03
Yes, yeah. Another way to say that is who, you know, who would be more than happy to help me. There's who would be my customer to your point and then also, who would be more than happy to help you find those customers? Yeah, yeah. Interesting. I couldn't figure it out on the podcast, doing it live running through my scroll through phone. This is like it's always fun to have a chat with you. But this has been fantastic because it's great to kind of pick apart I suppose your your early days and your ongoing journey and you've learned so much and you share so much. And I really thank you for that. I think people should check out your blog. Check out your podcast with Jen. It's short, it's sweet. I think it's brilliant. added the added skills you want to say anywhere people should find you not at all just
Peter Shepherd 44:52
Thanks for having me. Conor I always love a chance to chat with you. And the fact that we got to record it was just made it even funner
Conor McCarthy 44:58
absolutely cool. Talk to you soon.
Conor McCarthy 45:02
next time on the first 10 podcast, Margo Aaron shares the most valuable lesson she learned on turning meetings into sales. Let me tell you, Hunter I closed 90% of deals after Oh my god, like it changed my life. Thought and more on the next episode of the first 10 podcast.
