Talking with creative coach Jonathan Tilley

Episode #191

Today’s guest is Jonathan Tilley, author, speaker and creativity coach.
Such an "creative" talk and important information if you are thinking of switching careers from 9 to 5 to freelance.

Listen in to some great advice! Also, some new craft products I love.

Transcription of interview with Jonathan Tilley

Alison Lee: Ok. You know I love these kind of conversations. Today I'm talking with Jonathan Tilley. He has a website of the same name. And I love it. On his website it says "Where he helps creative people transition into successful, creative freelancers." So I love that. Thank you so much talking with me today Jonathan.

Jonathan Tilley: Thank you so much for having me
Alison. It’s a pleasure.

Alison: Alright. So first off, tell me your definition of freelancers.

Jonathan: Freelancers. OK. So I would define freelancers in the sense of what they are not. So freelancers are definitely not 9 to 5'ers working in a cubicle waiting to turn 65 to collect their retirement. That is not a freelancer in my book. If you wear a suit and tie, you are probably not a freelancer, a creative freelancer at least. If you are a freelancer, you probably don’t have, you probably have more of an inkling towards the right brain. So you're a little bit more creative or maybe a lot more creative. So yeah. That's how I define a freelancer of what they are not.

Alison: OK. And how do you differentiate a freelancer from an entrepreneur?

Jonathan: Oh that is such a good question. Because I speak a lot at many conferences. Some conferences are of entrepreneurs; others are from freelancers. And I get this question a lot actually. So, I've sort of created my own little conversation about it and it goes something like this. I think a freelancer is somebody that's very right brained, that maybe needs a little bit of help with the left brain stuff like analytics and math and organization and structure. I think entrepreneurs are thee opposites. The entrepreneur section has really strong left brained qualities: Math, Structure, Vision, Drive. But there may be lacking a little bit in the creative realm on the right brain. So I find, and I like to go back and forth. So I really enjoy 50% left brain, 50% right brain. So I think freelancers and entrepreneurs would really benefit each other and sometimes we do when we freelance because we sometimes work with entrepreneurs who need the creative outlets for their product. So yes, I find that dichotomy of freelancing and entrepreneurship quite interesting.

Alison: I do to. And I think that one doesn’t mean they're both for you. I think there [inaudible] be very different.

Jonathan: Exactly. Exactly.

Alison: Now. Ok. So freelancers, we are going to take that term away from meaning it’s just something you do in between your next corporate job. I mean that's the way I hear it used sometimes or people use it as freelancing separate, in addition to their regular day job.

Jonathan: Exactly, like a side job or maybe. If they have their 9 to 5, if they have their regular job but they want to transition out of it into freelance, then you know you work weekends, you work nights on your side job which will turn into your full time job once you transition.

Alison: OK. here's the other I've discovered. I'd like to know your opinion. What do you think is the biggest fallacy about what you'll have when you freelance?

Jonathan: Oh. The biggest fallacy that I think that people when they go freelance that it’s going to be all fun and games and that its going to be pure creativity. Which it is, I mean you're your own boss which is such a wonderful thing. But also when you go freelance it’s your job to make sure that the jobs keep coming in. It's the left brain sort of thing. It's the, just making sure that everything is taken care of on the business end. So once that's taken care of then you have the freedom to create. And I think a lot of people forget that or creative people get so inundated about that they just feel like throwing their hands up in the air and just saying I don’t know how to go forward with this.

Alison: Yeah. I've heard many people think that it’s going to be, which is sort of true but not really that all their timers are on. That they sort of this endless time off then to do what they want when they freelance. And always called when I was really a freelancer of my own business freelancer kind of thing, we called it unemployed when you [Laughter]. Not on a vacation. The only way you could go on a vacation was you knew your next freelance gig was coming up in 2 weeks. Now you can go on vacation. Otherwise you're just unemployed. So I think it gets, you know there's that in there. Now when you are working with people that way, what is their biggest fear then about freelancing?

Jonathan: I think that their biggest fear is when is the next job coming in? You know. And to go back to dovetail the last question into this question, the whole freelance thing it’s so romantic isn’t it. Like "Oh I have all this time. I'm going to be creative and its beautiful." Where at the end of the day it’s like "Oh geez, the rent needs to be paid." So what am I going to do? So I think the biggest fear that people have is when's the next job coming in? You know, or how do I get the next job? How do I reach out to people? How do I build my list? How do I create more of a client list and continually give to them, give something of value to them or be a resource to them without feeling like you are a jerk or like you are spamming them? Really you're not but a lot of people are so petrified of reaching out to new client prospects because they don’t want to come off unauthentic.

Alison: Like the old used car salesman

Jonathan: Yeah. Exactly.

Alison: Yeah. No that's true, that is a, yeah. And how do you help people with that? That's a very valid point there. Desperate is what comes up.

Jonathan: Yeah. Exactly. So there's either you know I think there is a lot of creative people just waiting for the phone to ring but they are not putting in the effort to get the phone to ring. And I believe that, I think this is a part of everybody that we are so afraid to reach out, we'd rather be asked. But sometimes especially if you are a freelancer, you need to ask. So I've noticed this myself and I've noticed this with all of my creative friends that are freelancers and through research and through trying different things have actually created an online course of helping creative people reach out and build their client list and write awesome cover letters the rock instead of make you feel like a used salesman, you know.

Alison: Oh that's a good idea. We're going to have the link to that everyone who just heard that not to worry in the copy so people can click that. Absolutely. Yeah. That's a big. You know what? It's so funny. I'm hearing you talk Jonathan and I'm like, "Oh yeah. Be nerve racking going freelance." And I realized wait. I've been my whole life that way. Oh yeah right, I forgot. You know what always came up for me was that I always thought it was more insecure to work someplace because you could always be fired.

Jonathan: Yeah. Totally. I mean those things are over. We're living in 2015 not 1954 where you know your dad said go to college, get a degree, get a 9 to 5 job and retire when you are 65, that secure me. That business model no longer exist and if it does, you are living a lifestyle like in 1945 and not 2015. And with cutbacks and unemployment and you can lose your job within 2 weeks or maybe sooner, you know. So going freelancers is actually you have so much more control over the situation.

Alison: Yes. I agree. I think another thing that people don’t realize, see if you agree with this is. I was talking to someone; I'm not going to name drop. But just called "famous you'd know the name". And he said that we still always had to make the phone call. You can never wait to have the phone ring. And I think we assume when you get to a certain place people will call you. And that's not true.

Jonathan: Yeah. Not at all. I think it’s so funny. When you understand the rules of the game of TV, film, whatever, you know. When you understand how it actually works. Then the fantasy is gone, the romanticism is gone and you just go "OK. So this is how it runs. Alright. I can play this game to." And it’s not a game as in spar me you know used car salesman it’s like, “Oh we all have to do this, you know.” For example, last year, 2 years ago I applied to do a Ted talk and I got the chance to do it and it was great. It was a wonderful time. Do you know how many people have seen my Tedx talk and said “Oh my god! How did you do that?" And I said, "I asked."

Alison: Yeah. And congratulations and it’s great. People should watch that as well.

Jonathan: Thanks. Thanks. But then it’s just like, you know you have to put in the effort. You have to ask. You have to reach out to people to get what you want otherwise. Clients aren’t mind readers, they are clients.

Alison: Listen and I always think that you know having been on both sides of the fence, someone who needed to collect content to publish it, that you hope people will have a nice packaging come to you. You just made your job easier.

Jonathan: Totally.

Alison: Yeah. I think people forget that. That that's their job. If you show up with everything in order it’s like, "Oh thank god. Yeah. We'll take you."

Jonathan: Somebody finally gets me.

Alison: Yeah. I think it’s really important that way. So when you are working with people where is the biggest Aha moment that. Give people an Aha moment about building up a clientele. Like lots of people listening are artists, they make things. And I think what I hear is the block called "How to sell their first piece". That seems to be a really difficult thing.

Jonathan: Totally. Such a great question. I think that there's this thing of when we reach out with our work, with our creative ideas, with our creations that have come from such a sacred deep vulnerable place in us that we're bringing out into the world. It's very, very vulnerable. We're very much attached to our work. Now the thing is if you reach out to 5 people and those 5 people say thanks but no thanks, you feel crushed. But there are 7 billion in the world and I think just statistically this isn’t very left brained. Statistically if you reached out to a thousand instead of 5, you're going to get more feedback, you are going to get the same amount of rejection but you are also going to have the opportunity to get more yes's. And if it’s not a yes it’s going to be a not right now. Or if it’s not a not right now it's say "Hey I like your work. You might want to work on this and go on this direction. And once it’s done please show me because we'd like to feature you in something else." So I think the problem that most creative people have is that when we reach out it is full of anxiety and 100% of our self-worth is invested in it when actually we just need our pieces of work go and share it with the world without wanting anything in return and when it does get picked up by somebody, then that's a wonderful thing. But to constantly keep putting yourself and your work out into the world, I mean Picasso he was amazing. He would just do something and then throw it out into the world. And he just produced so much so quickly that's what picked up and that's what sold and it was just amazing. I’m a big fan of his and I used to research him and everything. And I just think we get so caught up in the sense off "Oh nobody is going to like me." When we have all these wonderful outlets to showcase our work and give from a place of abundance and know that the more that you give you will get something back. And just to continually put yourself out there and it is vulnerable and it is scary but it’s not the end of the world if somebody says no. It actually feedback which is very, very important for our work.

Alison: Well I'm a big fan of the vulnerable place. I think vulnerable is your best strength, so it’s going from that point and putting it out there, even though it can be a little upsetting when it doesn’t go your way. But I like what you said about the left brain and the numbers part. It's true. It’s a numbers game and if we can put some of that emotion over in that area.

Jonathan: Yeah. Exactly. Like get excited about sending out to a thousand people instead of 5. Like geez, I have a thousand people that I want to send my stuff out to. This is amazing. And the amount of opportunities that we have to with the internet to get those thousands of people, we never had that 10, 20 years ago, you know.

Alison: I know. I love that.

Jonathan: So it’s such an asset.

Alison: I love it. And I think you know. Listen I never, before I started my business I didn’t even know there was the business to business because I didn’t have that in my background. I only knew from creative. And I found that embracing the business can also be creative.

Jonathan: Totally. So creative the business side of it, you know. Because there's no structured model, I mean there is. You have to make sure that the rent is paid. But, you know, there is so many creative ways of making that happen, you know. And the way that I run my business is totally different to the way that somebody else runs their business. And I find that so refreshing and so interesting to see that what works for me might not work for somebody else and vice versa.

Alison: Right and then you can learn from that person as well what they are doing. And that I love. That's why I love talking toe everyone to see what they do that's different. I want to touch a little bit on, I love that you have on your site called "Embrace the F Word: Failure". Now I believe like all the classes we have at are taught by masters. But what they're really teaching you is not their failures. They are teaching you what they learned because they failed a million times, right?

Jonathan: Exactly.

Alison: So what do you tell people when it’s like, what's your thing on failure?

Jonathan: It's so funny because I do a lot of public speaking and that is the number one most requested talk for me to do.

Alison: Really?

Jonathan: Yeah.

Alison: Because it just goes to our insecurity place of like?

Jonathan: Totally. And its universal. I mean I've given that talk to entrepreneurs, I've given that talk to freelancers. I've given that talk to economist. I've given that to.

Alison: Yeah. It's the same anywhere.

Jonathan: It's the same anywhere, you know. And it feels exactly the same.

Alison: It feels terrible. I mean I know that one of my biggest wants, and it makes me laugh and I have a joke with my son. I did my first keynote speech and I knew it was terrible. I felt like a total failure. And when I talked to him, you could tell by my tone of voice it’s like, how long are you going to be in this mode from that? It's like I don’t know, it could take a while.

Jonathan: Yeah. Exactly.

Alison: But then, what do you learn from it?

Jonathan: Yeah. What you learn from it. That's exactly it you know. You got to, Ok so you failed, you know. I don’t know one single person that could walk the day that they were born. It's not possible. We just don’t remember it because we were babies. So we've become so accustomed to having everything so quick and fast and go, go, go, go, go and success after success, that we really haven't the opportunity to sit down and just fail for a bit or screw something totally up and just be like "You know what? I screwed up and I'm going to mourn it, I'm going to acknowledge it. I'm going to ask myself what can I learn from this." And use it as a learning curve to not do it again until you hit success. So for example you know that spray can WD40?

Alison: Yeah, I do.

Jonathan: Do you know what the 40 stands for?

Alison: No, what?

Jonathan: 40th attempt.

Alison: I love that Jonathan. Is that true?

Jonathan: It's true. It's totally true.40th attempt. So WD40, we never heard of WD33. We've never heard of WD7 because those were all failures. We know WD40 because it took the 40th attempt until they actually hit. Or what about the number 52? Angry Birds, the game Angry Birds needed 52 attempts until it hit success. It needed 51 times to fail until it hit success on 52. Or the number 1526. Dyson, the vacuum cleaning company, they needed 1526 prototypes until they hit success. They must be really patient people.

I love that.

Jonathan: So, these major companies have had to go through massive amounts of failure in order to get to where they are now. So when we crippled because we sent out our work to 5 different people and 5 people say no, no thanks, not right now, come on, grow up. It's time to really put on your big person pants and here we go. Let’s do it. But everybody goes through this. They just don’t talk about it.

Alison: I'm a big fan of talking about it because I like to get to crying and then laughing because you know. And then OK, so I do think there is gold, I really do in every single failure. Like in that case of my keynote speech, I didn’t know that you could do a good one. I didn’t know the structure behind it. I didn’t know it had structure. So then I was on a whole new learning.

Jonathan: Exactly.

Alison: Yeah. I think there is always gold in everything single thing, everything piece of feedback you get.

Jonathan: Totally. And I mean even think about when you're crafting something, when you are creating something. It could be, you know the silliest thing from cookies, baking cookies and you leave the cookies in too long or too short and oh, OK. The simplest things to like stubbing your tow to not putting on your blinking when you do take a left turn and then you get beeped at. You know those are failures that we can learn from. Little small everyday failures and we can learn from them and then relate that to the other larger failures that happen in our lives and say "Hey, can we just laugh at this and learn from it and move on so we can hit more successes?"

Alison: Yeah. And just to admit to it too I think always helps. It was really bad, that was so bad. It usually isn’t as bad as you make it to be but its fine to just feel it that way. I love that WD40 thing. I have a whole new respect for it. I'm going to take that can out and put it on my desk.

Jonathan: Yes. As a trophy.

Alison: Yes. I love that. Alright so now, one thing you talk about which I love this: Freelancers Financial Freedom: How not to be a starving artist. I hate that term starving artist. To me should be removed. It’s like what's up with that, you know. Really? No. So what's your thing on that?

Jonathan: I think with the term "Starving Artist" it’s the fear of selling out or what selling out means. It's sort of like the opposite in the corporate world then they said the "Man". Working the "Man" which is such BS, you know. So this whole thing of starving artist, "Oh it’s a labour of love. It's my passion. But I don’t want to get paid for it." I just go "OK. So you enjoy being on the board line and homeless?" OK.

Alison: Some people do.

Jonathan: Some people do and they love it and that’s fine. But I think the whole starving artist thing is once again the romanticizing of it where I just go you know. We've been put on this planet for a reason and whatever artistic thing that is or whatever creative thing that is, you were given that gift. I'm horrible at math, horrible. Do you think I went to Harvard for math? No. Of course I didn’t. I went to Ithaca College in Cornell for music theatre and dance. And that totally fit to who I was. So I think it’s our strengths that we should really reinforce and say, "Hey I stand by this and this is who I am. And when you ask for your prices you know when you say "Hey this is how much I charge for the work that I do", there should be pride in that. There should be, this is the price, you don’t go to the grocery store and say you know" Oh that gallon of milk is $1.50. Can I get it for 74 cents or half off?" You know. So it’s the same thing. But because the milk doesn’t have a soul and doesn’t have feelings, it can’t you know priced up itself. We as artist, we very often have the tendency to price them ourselves. Here is one trick to not price up yourself or when you are trying to ask for proper rate. When you are on the phone with somebody, whenever you say your price, whether it’s like $100 did you notice how my voice went up? $100?

Alison: Yes.

Jonathan: Which sounds a good question?

Jonathan: See if you say my price is pause $100. And land. Go really so land it really deep in the gutter of your chest voice, people are going to go "Oh. Ok. Their price is $100. Great." Even if they wanted to pay 75. So that's a little trick for you guys.

Alison: That is a very good trick. I always notice that when you people will say their name and if it was me "My name is Alison Lee." It’s like are you sure?

Jonathan: You sure?

Alison: It’s you know, state it with a finish at the end there. Well I also think that the starving artist thing, listen is our job as artists, I put myself in the category to make sure that you know. People will, if you keep that thought in your head, people will not pay you that amount. I mean certainly in the world of acting I'm aware of that you are supposed to give it away for free or work for, you know dollars. There's something that we allow it to occur and it has to just. As artists you have to keep saying no, the value is more. So you have to do it just to make it all work for everyone

Jonathan: I think so to. I think, it’s such a great word, value. What’s the value? For me the value is this. For somebody else the value is maybe less or maybe more. Or you're going to get to a point in your creative career where you know, you are not challenged anymore and the money is coming in and its ok. But you're maybe not being challenged anymore. What really entices you is something a little bit hire up which maybe has a little bit more value to it, which probably 99% of the time is going to be more expensive. Your prices might be a little bit higher because you want to add or share that much more value than before. So I think it never stops. You never make it, quote unquote. I just think it’s a thing of the amount of value that you are offering or the value that you are taking from it depends on the intrinsic value in your heart and your soul and there's a monetary price to that to. And I think being starving artists, it sounds romantic but we all need to pay the rent.

Alison: Yeah. It’s not romantic. I just want to cross that word out.

Jonathan: It's hungry. And nobody likes to be hungry.

Alison: Yeah. You're hungry. You need food is what you need basically. So that's done. What was a just thinking about with artist there? That you just need to constantly look at yourself, put out the value and state it the way it is and get the feedback and on your go. It's like, and then keep push yourself. I think that's the other thing. Some people think as a freelancer if you have a job, I’ve heard this, you know. When people I know were working would say "Oh. You're all set." Because you know they think looking at someone, "Oh you're all set now. You have that." And I don’t think, I think that's another fallacy. You're never set, you know. It's a constant, organic changing type of thing. And you know people who keep moving on and doing stuff it’s because they're asking, like you said. They are pushing the envelope that way and I think that's one of the trickier things to have people understand is their own push, pushing forward that way.

Alison: I totally believe that. I think we need to push, drive, hustle to get where we're going. It's our job to do that for our inner artists, you know. But pretending that you are your own inner artist’s agent, like you are the agent for your inner artist. And sometimes you can land a gig or land a row of gigs and be like "Hey, I’m really comfortable and its nice but gigs usually end." Everything is non-permanent you know. So everything is constantly changing. So sometimes you might plateau, sometimes you might stagnate but we always need to be looking out for the next possible job that can come in and not in a spammy, used cars man sort of way. In a sort of way of like "hey, where is the value that I can add?" How can I be a resource to somebody? How can I create something that blows my mind that I never thought I could do and be a part of something bigger than me as a whole?

Jonathan: And I agree 100%. And you know what also I think in there Jonathan, that people don’t, not everyone sees until you're in is how generous you have to be in giving away also for free. You and I are doing this podcast together but we are doing this for free because that's what we do. But we know that energy will promote the other things we do that people who are interested. So that's a big part of it as well which is great you know to get yourself more out there and more people find out about you that way.

Jonathan: Exactly and just to reiterate we are doing this for free but there is an intrinsic value for me. I feel like I’m making an impact on your listeners. I hope I am at least you know. And I want to share where I am up to in my journey with your listeners and that’s the impact of giving and value that I want to bring across you know. And you can’t put a monetary value on that. True there are things that you can put a monetary value on. But giving an interview, most interviews unless you're an ex-president of the United States are usually free.

Alison: Right. But I just wanted people to understand that, that doesn’t fall under the starving artist. There is plenty of ways to give away free and generous because you are promoting yourself that way. That's a different type of thing and it’s really important. Well I'd love to hear before we finish up, you talk a lot about your sacred space where you create and what do you mean by that? What do you think works? Or what do people need? Or how does that work?

Jonathan: Such a good question. Oh that’s great. So we're creative people. We are connected to our inner artist, our genius, inner creative genius. Whatever you want to call it. And that thing whatever it is needs to be in a sacred space, you know. When have you ever seen a dance rehearsal happen in the middle of Times Square in a traffic jam? Where have you ever seen somebody write a novel underwater, scuba diving with sharks? So the place that you're doing your creative work in has to be a place that you consider sacred, you know. Rarely do you have the chance to really clear out a room or find a space or table or a chair or somewhere in a cafe and really just make it your own. And if you just stay aware of your surroundings and the areas that you create in, I mean sometimes if you are in a crowded cafe you might put earbuds in or listen to soft, gentle music. That's another way of creating sacred space. And by honoring your sacred space on the outside, the environment that you're in and having that match your sacred space on the inside for your inner artist your creative genius, you can get some really great stuff done. You can create some really awesome stuff. So for example for me in my office, in my studio I used to work from home and there's a. I'm actually home right now because it’s the evening time. In my old office space, it’s now the guest room but I have transitioned my creative space into an office space outside of the apartment because I needed a space that I could just call my own 100% without any distractions, without the postman saying "Hey can you collect this delivery for the neighbors because we know that you're home." And every 5 minutes the doorbell [inaudible]. So I have my own lovely office space that I just treasure and I do a lot of writing and the majority of the time, the only time that I really do my writing is when I'm, and it’s this really weird ritual. I have to sit on the couch in a specific position with 2 and a half pillows behind me, 2 and a half, with my white blanket on top of me covering my legs and my French bulldog Dexter sitting between my legs and I have my laptop on my lap. That is my writing position. I cannot write anywhere else if I’m going to do some really deep writing. So that is the way that I created sacred space for my writing. And I think if you notice how you work and what your flow is and what your rituals are and what your sacred space is on the outside, it’s going to make you feel oh so good on the inside. And that’s how you in a nutshell, that's how you create sacred space.

Alison: No, I love it. It also makes you show up to create. I mean then you have it, you know because it is hard. You know you were mentioned all that way back when I used to design advertising and catalogues and everything. You've to create from the abstract world. So how do you actually do that is sort or crazy when you think about it. SO I had to sit down with magazines and the way I started working was looking through magazines which would look like someone else. You don’t look like you’re working. But it put my brain in the place where I could think abstractly and then start. And I think if you show up in that place you’ll start making work.

Jonathan: Exactly. And then to go back to the romanticizing "Oh in a freelancer. I'm creative. I'm just doing my free thing." No you are sipping lattes and smoking cigarettes. But if you show up for the work and even your process is flipping through magazines which is work. Its creative work in how you describe it. You show up, you are making yourself available to tap into the creative process and you have a space to do it in. You have your own creative process of getting deeper into whatever you want to create and that’s so necessary and so important. Otherwise you just creative something half-hearted and not be really proud of the work that you've done.

Alison: Well I think what you just said is great. You're making yourself available to tap into the creative process. Because so many people dance around their studio space or whatever. I've been there, we all do it. But you make yourself available when you are setting up. The sacred space is nothing to do with going to a church or it could but it’s what it is for you to all the process to start.

Jonathan: Exactly.

Alison: Yeah. We figured it all it out!

Jonathan: Amen to that sister!

Alison: We did it. We figured it out. So now, this is one of my favorite topics so I love it forever. But I want to make sure everyone knows your site and it will also be on my site so you can click through but it’s your name, Jonathan Tilley correct? And tell everyone again some of the classes you have that they can sign up for online.

Jonathan: Right. Thank you so much. So my main website is where you can learn all about me but I do have a couple of e course. One being out list building which we do every winter and every summer. We have summer and winter semesters of the 6 week course and the course is called "League of List Builders." L E A G U E OF L I S T B U I L D E R S .com

Alison: And this is for people to get more people on their list instead of 5 and go for the thousand.

Jonathan: Exactly. Or millions of people, you know. It depends on what areas that you are working in but this online course is a 6 six online business course for creative on how to develop long lasting, deep and powerful working relationships with future clients. And every day you have a little task to do, the whole process is broken down into daily bit by bit things. We even have stuff on the weekends where it’s not really work its more sort of like playful stuff but it also ties into list building which you maybe not have thought of before. And what's wonderful is that you can sign up for a freebee. You get 22 free videos from the actual course. Little sneak peek snippets of the course to see what it’s about and just to check it out and learn something for free. And then the other course is the Sacred Space Sessions which we just recently spoke about of created scared space for your inner artist. And you can find all the information there at

Alison: Love it. I knew it would be fun talking to you.

Jonathan: I knew it would be fun talking to you too.

Alison: It was a pleasure. Thank you so much Jonathan. Create, Create, Create I say! I'm going to go to that sacred space shortly.

Jonathan: Awesome. Thank you so much.

Alison: Take Care.