Ep 101: From Solo Creator to Creative Leader
Mastering the Transition to Leading Creative Teams
SUMMARY
In this episode, Dustin Pead explores the challenging but rewarding journey from being a solo creative professional to becoming a creative leader. Drawing insights from Jason Sperling's book "Creative Directions," Dustin discusses the mindset shifts needed, practical transition strategies, team-building approaches, and vision-setting techniques that can help creative professionals scale their business while maintaining their creative integrity. The episode offers valuable guidance for freelancers and solo creators who are ready to build something bigger than themselves.
KEY TAKEAWAYS
⚡️ The transition from solo creator to creative leader begins with a fundamental mindset shift - changing your language from "I" to "We" and embracing your identity as a leader before you even build your team
⚡️ Know when it's time to expand by recognizing key indicators: reaching capacity thresholds, identifying skill gaps, evaluating ROI on new team members, increasing project complexity, evolving client needs, and assessing opportunity costs of handling lower-value tasks.
⚡️ When building your creative team, prioritize culture fit alongside skill set - hire people you'd actually want to spend time with outside of work, as shared values and compatibility often matter more long-term than technical skills alone.
NOTABLE QUOTES
💬 "There has to be a point in your creativity, in your endeavor, that you have to shift your mindset. You have to go from this solo creator that everything begins and ends with me... to a leader."
💬 "Success is also going to come from having adaptable systems. You're going to have to have some structure, but the structure doesn't have to stifle innovation."
💬 "Are your projects managing you or are you managing your projects? There are some fundamentals that me and my team help go through."
EPISODE RESOURCES
⚡️ Jason Sperling's book: Creative Directions: Mastering the Transition from Talent to Leader
⚡️ Dustin's eBook: "Using Asana for Creative Teams" available at DustinPead.com/store
⚡️ Learn about Dustin's creative services at DustinPead.com
⚡️ Subscribe to my weekly newsletter here
TRANSCRIPT
Okay, you've mastered your craft as a solo creative freelancer, but there's a nagging voice that keeps asking if you're ready to build something bigger than yourself, a team that can multiply your vision while allowing you to step into true creative leadership. Today, we're diving into the transition from solo creator to creative leader with insights from Jason Sperling's game changing book, Creative Directions.
Let's get into it. Creatives from chaos to clarity. Welcome back to creativity made easy. The podcast where we transform creative chaos into clarity. I'm your host, Dustin Pead creative coach and consultant. And I help creatives know themselves, their process and their teams that they can create with efficiency as they scale together. This podcast is for any creatives out there, whether you're just dabbling into what it means to be a creative or your full-fledged been doing it for a long time. Designers, photographers, writers, all creative entrepreneurs seeking some practical and actionable strategies to grow their creative business through efficiency. Right. That's what we're all about here is efficiency. That's what takes us from creative chaos into clarity. Today, I'm so very excited to dive into a topic that is near and dear to my heart from solo creator to creative leader.
But before we get into that, I want to remind you that you can find me online, Dustin Pead, P E A D dot com. There you can learn all about my creative services, coaching, consulting, and speaking as well. Got a couple of really cool speaking engagements coming up later this year. If you're interested in having me speak to your team, whether it be live in person or digital. You can go to that speaking page and fill out the form there and we can chat all about it. Would love to. You can find out all about me there and every way that I can help your team. All my free tools and resources all found right there on the website. You can follow me on social media at Dustin Pead, P-E-A-D, like I said. And if you're watching on YouTube, I'm glad that you're here. Would love for you to hit the thumbs up button to like it. Also subscribe and ring the bell while you're there as well. And you'll be notified every time we drop new content, just like this podcast every single week, you'll be the first to know about it.
All right, so let's get into today's episode. I want to just kind of set the tone a little bit. I was kind of thrusted into creative leadership without much preparation. So many of you know my story. You've read the book Growing Upward that I released last year. And I went to Liberty University to study worship music and ministry. Right. So there we learned a lot about how to lead worship, how to lead musical songs of praise in a church setting. Right. And so much of my leadership was about that. Those few moments each week, 20 minutes or so on stage and very little was taught to us at the time because the worship program was extremely new there about how to lead teams.
And so when I took my first job out of college at a church just south of Indianapolis, I immediately had a team of people that were looking to me. Now they were all volunteer, but still it was a team, right? That were looking to me for leadership. And I was like, I'm fresh out of college. don't, I mean, I can, I can tell you what I learned there, but I don't think y'all are ready for that. I like, I don't think we're there yet. And so it took me a few years to kind of trial by fire. And I wish I had this book back then. It came out in 2021. I have it right here. It's called a creative directions, mastering the transition from talent to leader right here. If you're watching on YouTube, I'll put the book up and let my camera do its focus thing. There's the book right there. I'm going to have a link to it in my show notes. Um, this is unofficially not, this is not sponsored by Jason. Um, in any way, but Jason, um, who I don't know, never met, um, but I've gleaned a lot from him over the years through this book. It really is a how to textbook from going from this solo creator to creative leader.
So we're going to reference it a lot in today's episode, but if you don't know about Jason, that name doesn't sound like a household name to you. Uh, Jason was a, uh, professional creative, uh, higher up in the ranks of Facebook and now owns his own agency and has worked with some of the top brands in the world. And so today we're going to dive into that journey that he kind of lays out in the book a little bit. And we're going to talk about leading a team a little bit, because next week we're going to talk about the art of creative leadership. So we'll, talk a little bit about leading a team here, but we're mostly going to be talking about strategies for transition, vision setting, growth management, things like that. So let's go ahead and dive deep in so that we can learn how to go from solo creative, solo creator, to a creative leader.
All right, so the first thing is pretty simple, right? It's a mindset shift, right? Before you can make any strategic changes, practical changes, hiring, onboarding, whatever, bringing in people to help, there has to be a point in your creativity, in your endeavor, that you have to shift your mindset. You have to go from this solo creator that everything begins and ends with me, solo creator to a leader. And I understand that there's a lot of fears involved in that. And Jason in the book lays out some of those fears. So there's fear of creative control, right? We want to have our hands on everything from beginning to end. There's anxiety about diluting the quality or the vision that made your work successful to begin with. There's imposter syndrome, which, newsflash, that doesn't ever really go away. We all, all deal with imposter syndrome, but it leads you to kind of feel unqualified to even lead other people to begin with, right?
There's concerns about managing interpersonal conflicts among team members. Like, I don't want to babysit adults here. don't, don't want to have to worry about this person, my designer getting my web designer getting along with my photographer or, know, all these things, right? There's resistance to giving up the identity of being the creator and becoming the leader. We don't want to necessarily give up the title of creator because that's what we got into this thing for in the beginning, right? Was to create. We're going to talk about how to hang on to some of that. There's also fear of spending more time managing than creating. And that's a real legitimate fear. But if we, if, if we really do feel this thing, welling up inside of us that says we need to, we need to grow this, this is, this needs to be more than just what little reach I can bring to the table. Then we're going to have to conquer some of that anxiety.
There's concern about building systems that enable creativity rather than stifling it, which we talk about on this podcast all the time. You can listen to any of the previous episodes. And there's then there's resistance to the administrative aspects of leadership, right? Budget schedules, performance reviews, all of which I would say doesn't necessarily have to be you. And we can talk more about that. So we have to identify, we have to shift our identity from the doer of all things to the leader of all things. So mental mindset shift first. And the way that you can do this immediately is very, simple. Immediately start to change your language, change your language from, uh, here's what I do. Here's my work. Here's my approach to, to this prop, to this problem. Here's how I would tackle, uh, this creative project. Here's how I would lead this creative project, right. And start moving it towards your team.
We do this. We work with efficiency. We have a system for that. We solve problems this way. And just by saying that, even if it's just you, and I know you're like, well, that sounds like schizophrenia, like there's a lot of people in my head, right? But if you begin to make that mind shift immediately before you even bring in any other help, you'll start to operate. It's kind of like putting on the big boy or your dad's uh, suit, right? When you were a little kid and you felt, even though it was like too long for, you know, it covering up your hands. was way longer than your arms, right? You had an opportunity to kind of feel what it's like to be big. I feel what it's like to be an adult. Right? And so this is what we're doing. We're, we're, moving the language in our mind from it being just us, the small focus to we, here's what we bring to the table. And, honestly, folks, the more I work in this business, the more I realized is that other businesses that are going to work with you are going to understand that in order for you, for you to deliver on the scale that they want you to deliver on, you better have a team because if it's just you, you're limiting your impact. And we'll talk about all that.
So here's some questions to consider as you focus on changing your mindset. Right? So questions to consider when, uh, when did you know that it was time for you to expand beyond the solo work? Go back to that moment and think for yourself. When was it that I was like, I've got to expand this? Constantly remind yourself of that feeling, of that emotion, of that connection, and that will propel you forward into becoming the creative leader that you need to be. What were your biggest fears about leading others? When you think about leading others, what are the fears that you have? Write them out, right? Because then you'll be able to see the problem for what it is and you can tackle it head on.
And then think about your own creative journey. How did your own creative identity evolve? What were some key milestones? Did people speak into your life? Was it exposure to some new creative tactic or method or art form? What were the moments that kind of allowed your creative identity to evolve along the timeline of your life so far? Because when you understand those moments, you'll understand that every single time it took a leap, it took a step and there was some fear involved and there was some unknown involved. But being able to do that every single time, you realize, man, I'm so glad I did that because when I opened up Adobe Creative Cloud for the first time, I didn't know what was going on there, right? But I did it. And I said, I can do this. And I told myself I could do it even before I could do it, right? You tell yourself it's we even before it's we.
So you told yourself you could do it and guess what? Now you do it. Now you actually make money doing this thing using a tool that when you first opened it, it looked like a foreign language to you. Right. All So let's get into the next step, which is a transition strategy. All right. So there's a couple of different approaches you can take here when you're making the transition from solo creator to creative leader. You can do a gradual approach, which is probably smart in some ways financially. Right.
or you can do a rapid team building approach where you're just like, I'm going to hire a whole team immediately right now to come in and help scale this thing. And in Jason's book, he lays out a framework of understanding when to expand your team. And these are conversations that we are having right now in my organization as we look to grow what we're doing here for professional creatives. And he says, number one, think about your capacity threshold constantly having to turn down work or delay projects because you can't handle all that people are asking you to do on your own, it's probably time to expand. Skill gaps. He talks about skill gaps. Are there areas where you are personally limited and you're holding back the growth of your company or the growth of what you're trying to do or a project quality you need to possibly consider hiring someone specifically to fill in those skills gap. You don't have to be excellent and perfect at everything. You can be perfect at your one or two things and then you can hire out the rest of the things, right?
ROI or return on investment evaluation. You need to be able to assess what bringing on team members would, if it would generate enough additional revenue to justify the investment while maintaining or improving profit margins. in a couple of episodes ago, we spoke with Christian Brim, Profit First for Creatives, that him and the core group would be really good to ask. These are questions that I'm asking them right now because I'm a client of the core group and they are my fractional CFOs and I ask them all my money questions. And so the money question I just asked them a couple of weeks ago is, hey, based on what I've got coming in right now and what the projections are over the next quarter, do we have enough to hire these positions that I would like to hire? So evaluate that, bring other people in to see that from a different perspective, because sometimes you're too close to it.
Jason also talks about when you're trying to expand your team, the project complexity indicators. If a project requires multiple specialized skill sets that you can't reasonably master on your own, then that should be a signal to you that it may be time for team expansion, right? Another one, client evolution. talks about how as you as clients grow or as your clients grow, the number of them and the size of their organizations, they grow and their needs become more complex. Your team structure should evolve accordingly, right? If you're, if you're, if you're, if you are helping your clients grow, which you should be through your creative endeavors, right? If you are helping your clients grow, then you're going to have to grow along with them to be able to keep up with their ever-changing needs, right?
Another one that he mentions is opportunity cost assessment. Again, this is where I bring in the core group. Calculate what you're losing by handling administrative or lower value tasks instead of focusing on high level creative direction. Are there opportunities that you're losing because you're spending too much time doing the administrative work? That's time for you to go, maybe I should hire somebody to do some of these administrative tasks that I can't do or that I don't that I can do, but I shouldn't be spending my time doing.
The last one that he mentions in the book is a sustainability check. Evaluate, look, if your current workload and schedule, are they sustainable for your wellbeing and creative energy in the long term? Have you ever, at the end of the day, asked yourself, How can I keep doing this? Or said to yourself, I don't know how much longer I can keep doing this. That's a sustainability check. And that's a flag that if you do truly desire to continue doing this, then you're going to have to bring on some help.
So there are some first higher considerations. Do you need administrative support, project management, bookkeeping, doing all that kind of admin junk that creatives hate, right? Or do you need additional creative support? Do you need, hey, I've got more design work than what I'm able to do right now. I need to bring somebody else in to help carry the load of the work. Those are the two kind of lanes you need to look at, Outsourcing versus employees. Again, I hate to sound like a broken record, but I do go to the core group for this and ask them, should I contract this or should I w two this person? Uh, and they can help you walk through that. But I would always say no matter what you do, be upfront about trying it for about 90 days or so. 90 days is a good long length of time where you can kind of be like, wow, this is actually worth the money that I'm spending on this person. Or honestly, it's not.
But we're going to talk about how to onboard those team members here in just a second. So it actually is worth your time. The systems that need to be in place before hiring. This is one that I really work with my clients a lot right now is how do we multiply you as this solo creative and we're bringing on additional editors, additional designers, additional cinematographers, photographers. How do we multiply what you're doing? We have to document those things, right? We have to have some systems in place before we hire. And that's really where I come in and help, specifically as well in the project management fundamentals.
Do you feel like your projects are managing you or are you managing your projects? I'll say it again. Are your projects managing you or are you managing your projects? There are some fundamentals that me and my team help go through in all the episodes. I'm not gonna get into it today all the episodes and all the blog posts on my website, they can speak to that. Is there a clear scope definition and delegation skills when you're, when you're bringing on somebody, is there a clear understanding? Is there a clear definition? Is there a job description? Is there a clear understanding of this is where I end and you begin. This is where I'm going to let go. And this is where you're going to pick up. Right.
So, uh, Jason and his book has many, many case studies of successful creative transitions. Again, pick up the book, read all about it, keep it on your desk. Honestly, it's what I do and refer to it often. Let's get into the next segment though. And how do we team build for creatives? All right. So we've identified that we need someone. We've identified what to consider before we bring them on. Now, how do we actually team build around us as the creative leader? And I think it starts with hiring, right? It starts with finding the team members who compliment your creative style, right? Are you really good at coloring, but you might need to bring somebody in who's really good at the audio side of video, right? Or you're really good at layout print design, but you need to bring somebody else in who's more of a digital mobile web designer, right? Find those things that compliment your, your creativity, your creative limitations, but also your style, right? Are you really into post-modernism style, right? Of what's like the most hip out there, right? Cutting edge. Are you more of a traditionalist? Find some, find a yin to your yang, if you will, right?
When hiring, this is something that we talk a lot about at the Culture Base, the other company that I help run, where we help creative, we help leaders know what they're about, their processes and all that stuff, right? So that they can scale their businesses, like from the from the lens of their culture, but hiring for a culture fit versus skill set. This is a tough one. I, my opinion, and I, and I would say Jason does a really good job at kind of balancing both in the book. Um, my opinion is that you should always hire for a culture fit. Me and, uh, my team members or my clients will often talk about the people that we want to work with. And we, we use this kind of internal measuring stick when it comes to if we want to work with them, whether it's clients or whether it's someone that we want to actually bring on to our team. And we just ask ourselves, is this someone that we would actually want to spend time with outside of the work? Is this someone that we would actually want to go to a sporting event with, have a beer with, go to a concert with, have a date night with as couples, right? Like are these people that we want to hang around? Those are probably going to be good culture fits for you.
And I think long-term that it's more important to get a good culture fit as it is a skill set. Now, obviously the more immediate side of that is you do need someone with the skill set. So I think it's both, but I'm going to lean more in the direction of a culture fit versus skill set more often than not. That's probably biased because I help run an organization called The Culture Base where we help organizations grow through their culture. Right? But there's a different communication frameworks for creative collaboration all in the book. He also discusses, uh, managing creative differences, which is a big deal. We've talked about that before here on this podcast, uh, resolving creative conflicts constructively. So it builds up and does a tear down. And I, and I know that sounds like babysitting, but trust me, it's an opportunity for you to cast vision in and, and, and carry your ideals and your creative style further throughout, uh, the your organization as you grow it. And he also talks about having some feedback systems that nurture rather than stifle creativity. We actually talk about this over on the culture based podcast just recently. So check that out. The culture based dot com.
One more aspect here on team building that I want to hit on before we move on to our final segment of today is mentoring some junior creatives. One of my clients that I work with right now, we've partnered up with an apprenticeship organization who basically has students that connects students to growing agencies like my client's agency. And we can get the work at a fraction of a cost while building somebody up. Now, the great part about this is, yes, it feels good to kind of teach others and teach younger creatives how to do what you do. That's a feel good part. But the cost benefit is we can get them on a fraction of the cost than what it would a professional. Now, it may take a little bit more time in the long run to bring them up to your standards, but they're usually a lot more available. They're usually a lot more affordable and you can grow them in a way that fits your culture and the way that you do things right out the gate. It's not like you're having to teach an old dog new trick. So I would highly consider mentoring some junior creators through apprenticeships or internships. And I know it sounds like I'm just me. I don't really know how to have an apprentice. Um, it's a really cool old school technique to help grow your organization from the inside out and nurture the talent, uh, from, the very beginning, all the way through your organization.
All right, let's get into the last segment. There's many parts of Jason's book, creative directions and how to master the transition from talent to leader. As we said, uh, what we're calling this podcast from solo creator to creative leader. But before we end today's episode, I do want to talk just for a moment about vision setting and creative direction. And this is where he really kind of spends the whole rest of the book. And this is really the main reason that I leave his book on my desk at all times. But you need to create, you need to craft, I would say, a compelling creative vision that inspires. Right. So in my, this podcast, for example, at beginning of every single podcast, I say the exact same thing, is that why I'm here is to help creatives know themselves, their process and their teams that they can create with efficiency as they scale together. What I'm doing in that moment every single time is I'm reiterating a creative vision that will hopefully inspire you to want to listen. And so as teams get together and we talk about the projects that are at hand, it's an opportunity when we're all around each other.
It's an opportunity to continually cast that vision over and over. It doesn't need to be complicated. It just needs to be, hey, reminder, this is what we're about. Let me tell you a 30 second story this week about how we saw that come into play and how we saw that executed with excellence, right? And then we move on. But communicating that vision effectively to different personality types is a part of it too. And this is stuff that we talk a lot about too at the Culture Base when we're talking just recently in an episode about generational differences. One of my partners over there, Blake Bayer, wrote a book called Uncultured, in which he spends a lot of time diving into the psychological approaches that you take with different generations within your workplace and different personality types as well. We talk a lot on this podcast about Enneagram types and how to be able to work with certain Enneagram types and knowing their core motivations and core fears will help kind of nurture them up to where you want to see them.
But learning how to communicate that vision effectively to different personality types, that's just a part of creative leadership. It's a part of vision setting, and it's a part of creative direction. Documentation and reference systems. This is an area where creative direction, think, a lot of times people think that that loses its luster, right? That I'm a creative director and I work with big top brands and I don't have time to document and reference systems. The reason why most people are successful in life, no matter what area of professionalism they find themselves in, is because they have figured out a way to do the same thing over and over and over again, right? It's that 10,000 hours to become a genius at something, right? That genius is 10,000 hours.
So the 10,000 hours is the same thing over and over again, right? Well, as you're growing your team, in order for them to do the same thing over and over again, you have to create systems that they can reference and documentation that they can reference throughout so they can have this, so they can approach it the same way every single time. It's consistency. Consistency breeds excellence every single time. And there's times when you need to hold firm to the vision. And there's times when you need to adapt the vision. And Jason talks about this in the book. He calls it creative elasticity and vision adaption. talks about distinguishing between core and peripheral elements, knowing which aspects of your vision are non-negotiable versus which can be modified without compromising the essence of that vision. He talks about responsive adaptation, being willing to incorporate valuable feedback and new information while you preserve the central creative intent. He also talks about contextual flexibility. And when we're talking about, we hold tight to this vision or not, or do we flex it a little bit and adjusting creative approaches based on shifting the client needs or the market conditions or team capabilities, that stuff is always going to be changing, right? But you can do it without abandoning the original purpose.
He also talks about principled compromise that there are some finding some middle ground solutions that both honor your creative standards and the practical limitations of what's in front of you, right? Sometimes there's just, it's impossible to hold these standards. And so being willing to flex those things and having some grace on yourself and grace on your organization, your team members will go a long way. And lastly, progressive iteration. This is where I talked about viewing the vision as evolving rather than it's static. Allow for growth, allow it to flex and bend over time. This is why I like 10 year goals are amazing. They're a great roadmap, but really like no more than three, because things change constantly for you to be able to say, is where I'm going to be in 10. You can kind of aim for that, but we know that over time you're going to shift. If you're watching on YouTube, you can see me kind of use my hand as like a rudder or an airplane direction, right? We're shifting it just a little bit of a shift here and there can change that long-term target drastically. So that is the episode for today.
Creative directions by Jason Sperling. One more time. I'll it up on here on YouTube for you to see, make sure it gets all in the frame there. Yep. Jason Sperling, creative directions, mastering the transition from talent to leader. Highly encourage you to pick that up again. This is not sponsored by him anyway. I don't know Jason. I've never spoke to him in my life, but I'm telling you it's worth it. So pick that up. Another simple little tool for you to pick up is my ebook using Asana for creative teams. Now know many of you may not use Asana and that's totally okay.
I often say in my speaking engagements, it doesn't matter if you're using a whiteboard or Post-it notes or Asana or Monday or Trello, but the stuff that we talk about in this book and the stuff that John talks about in his book, it's just simple practical ways for you to implement and reiterate and grow your team from the inside out by having a consistent project management tool and the way that you use that tool over and over and over again. so check that out on my website, dustinpead.com slash store. You can pick up Asana for creative teams. it's 10 bucks. It's an easy to read ebook. You can disperse it throughout your team, your organization, let everybody read it, reach out to me if you have any questions or concerns about it.
And so what I would just encourage you today as we wrap up this episode is to just to take one thing that we talked about today. Take one thing. If it's a mindset shift, if it's a, hiring consideration, it's an onboarding consideration, if it's a systems and processes or project management consideration, just take one thing this week and put an action plan in place of how you're going to go from this solo creator, right, to creative leader. What's one thing that you can do this week to do that? I'll put the link to Jason's book in the show notes and I would love to hear from you.
If you're reading through that, reach out to me on social media at Dustin Pead, P-E-A-D, but definitely pick up that book and also pick up Using Asana for Creative Teams. My ebook, it's 10 books, 10 books, not 10 books, it's one ebook. It's 10 bucks, $10 on my website, DustinPead.com slash store. Next week, we're going to dive a little bit further into this creative leadership topic. We're going to talk about the art of creative leadership today.
I want to remind you you can pick up my newsletter, you can get a free coaching call, all that stuff on my website. I would love for you to check that out. But until next time, have an amazing week. Get out there, create with efficiency, and scale your creative work. I love you guys. Cannot wait to talk with you again on Creativity Made Easy.