Talking with creative coach Jonathan Tilley

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.

Jonathan Tilley

Studio Mojo

Grace McLean/Haven’t You Noticed

Chameleon Markers

Listen Now

Interview transcript

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?

What people are saying

  • Your classes are just amazing and I have learned sooo much from Cindy Pope’s classes on the Silhouette machines. She breaks it down so any beginner can learn. I didn’t take my Curio out of the box for a year until I watched her class. Now I’m addicted

    Beth B
  • Thank you for the informational class last night, and for the notes, it looks like a great product to work with. Best Wishes,

  • You are a truly generous soul to share so much with the community. I am constantly impressed by the extra effort you put into everything you do. A true inspiration. 

    Bridget D.