How to stop waiting for permission to be a professional creative, with filmmaker Henry Thong

with your host Jessica Abel

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“I’m an all or nothing person. So when I get that resistance…it’s like a stubborn trigger in me that gets triggered and I’m like, you know what? I’m gonna use the frustration that I feel that people aren’t seeing what I’m seeing, or the resistance that I’m getting.
I’m gonna use that as motivation to get it done.”


On this episode, I’m joined by award-winning documentary filmmaker Henry Thong for a conversation about courage before confidence. Henry’s entire career is arguably based on his willingness to get out there before he’s “ready.”

He began his freelance career right out of high school, skipping film school altogether. He moved from Australia to NY, without a back-up plan, and parlayed his personal success into a full-time job as a filmmaker for ConvertKit. Henry has a ton of personal insight to share about how to be more courageous with your work, and why regularly taking imperfect action is the key to developing your creative business.

More from the episode

  • How to turn pushback into motivation
  • Why NOT having a back-up plan might be your best bet
  • How “expensive” mistakes can lead to stronger decisions going forward
  • How to balance paid and personal work, and the surprising value of creative “hobbies”
  • Strategies for dealing with the fear of putting yourself out there
  • How to turn your stress and anxiety into excitement

This episode comes from the Creative Business Design Lab, a live monthly conversation I lead with other creative business owners where we dig in and focus on a single topic, sharing strategy and solving problems.

Join us live for the next session of the Creative Business Design Lab!

About Henry Thong

Henry Thong is an internationally-recognized documentary filmmaker. His original series Makers Who Inspire has amassed over 1.85 million views, and has been recognized and awarded in America, Australia, Europe and Africa. Henry has also worked with like-minded brands and produced film and video content in Australia, Singapore and the United States for the likes of ConvertKit, Bright Trip, Adam Liaw, and ABC Australia. As a dedicated documentarian, Henry believes the world is an interesting enough place without having to create new ones. He has an avid interest in the creative process and is passionate about telling the stories of artists.

Connect with Henry

Makers Who Inspire





Additional Links





Click here to view the transcript!

Henry: some of the best advice that I got is from a painter, and he was saying you never know who’s looking at what you’re making, even though it might like get only 5,000 views or whatever.

And he was right because there’ve been many times people have connected with me in the last few years and they said, oh, I saw this thing that you did. And I’m like, really?

Jessica: What does it really take to become successful as a writer or artist?

There are a lot of destructive myths out there about what a creative career is supposed to look like. We’re told we shouldn’t care about worldly success or money. We’re told that if we’re good enough, everything would magically fall into place. That’s a lie and it keeps us struggling, baffled, and hungry for any shred of information that might shed light on how to keep making the work we love. That’s why I get any two artists or writers or any creatives really together in a room. And it’s a foregone conclusion that the conversation will turn to money and the nitty gritty reality of being a professional, creative.

I’m cartoonist and creative business. Coach Jessica Abel.

In my own life. The studio visit back channel conversations with other artists where we share our insights and hacks anxieties and red flags have been critical to any success I’ve achieved.

And now. I’m bringing that conversation to you. This is the autonomous creative.


Jessica: Welcome to the Autonomous Creative. This episode comes from the Creative Business Design Lab, a live monthly conversation. I lead with other creative business owners where we dig in and focus on a single topic. Sharing strategy and solving problems. The theme of this lab session is courage before confidence.

And my guest is Henry Thong. Henry is a self -starting self- producing documentary filmmaker whose original series, Makers Who Inspire has amassed over 1.85 million views and has won multiple awards.

Henry parlayed his personal success into a full-time job as a filmmaker for the email service company, Convert kit, and continues to develop his personal work along with a new interest in film photography.

People ask me all the time, how to sell their work, how to get attention for their work, how to get clients, how to build their business.

And usually they do something amazing. But they’re sitting back and waiting for magic to happen and people to discover them.

Or they’re out there doing content marketing, like blogging or social media, which feels like a lot of activity– and it is a lot of work– but that too can actually be a form of hiding from what they really need to do, which is to go out boldly with their work and put it in front of people. Even when they don’t feel ready. Maybe especially when they don’t feel ready.

In my experience, you’re never going to feel ready before you do a thing. You only know you’re ready after you do it and it’s fine. You don’t die. You can look back and say, oh, I guess I was ready enough.

I asked Henry to join me for this conversation because his story is one of courage before confidence over and over again. He started making films, submitting them to festivals and winning awards when he was still in high school. Then he decided to go pro and become a freelancer as soon as he graduated high school, while his friends all went off to college.

One of the hardest things about being a professional creative is that our success depends on doing our work without permission and with no guarantees.

We’ll dig into what that looks like, what it feels like, and how to do more of it. We’ll dive into the deep end. Right after this.

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Jessica: Does part of you suspect that the system is rigged against professional artists, writers, and creatives?

Does it feel like with all the incredibly hard work you do. With all your expertise and experience that somehow success should have…


Hey, I hear ya.

I went through most of my career feeling like success was just one step away. Around a blind corner, and that all I needed to do to get there was. More.

More work, more marketing, more income streams, more… everything.

But at some point, or really, over and over again, I did so much more, I almost broke.

And while I did achieve certain markers of success. The kind of success that I kept expecting to arrive, where I could slow down. And take a breath, really have space to think and do the work I loved the right way. Where I could stop worrying about money for like one minute.

That success kept receding in the distance.

Here’s what I figured out.

Hustle grind. Just keep doing more and more and more. That is the scam. That is the system that’s rigged against us.

What if everything we’re taught in school, everything we absorbed from culture about how artists and writers should live. And the tsunami of advice from online marketing celebs about how to make it as a professional creative. Is just wrong?

And if that’s true, what do we do? How can we fix it?

I’ve got something I think you’re going to want to read about how to escape the cyclical burnout creatives fall into, and how to build a truly sustainable creative career without just piling on more and more.

Check it out at jessicaabel.com/creative-business. That’s jessicaabel.com/creative-business.

Now let’s start the show.

begin interview

Jessica: So, Henry, Here’s the detail about your biography that inspired today’s theme. You started out making films and submitting them to festivals and winning awards when you were still in high school, and then you decided to go pro and become a freelancer as soon as you graduated high school, while all your friends went off to college, you started your own business and dived right in to client work.

How does this all land for you?

Henry: Well, it was a learning curve, that’s for sure. A lot of mistakes were made. They were expensive mistakes. But I’m glad that I chose to go that path because when my friends graduated high school, I had a few in Melbourne. And I’m in Australia at the moment that’s why you can see the sun coming in. I’m from Australia.

So a lot of people, uh, friends of mine went to school in Melbourne. Pretty good film school. When they started graduating three, four years after we all graduated from high school, I saw them go through a lot of the similar stuff that I was going through right after I graduated high school.

It was just took them longer to get to that point because they were still in school. So I’m glad that I made that decision to go and make those mistakes and learn on the job instead of going through school.

Jessica: Right. Did you see them not making those mistakes because they waited longer?

Henry: Well, they had to make those mistakes eventually it just took a bit longer to get to that point.

Jessica: Yeah, I mean, I wanna hear about the mistakes, we’re gonna get there, but like basically this idea of… I mean, your particular case is, I think a really striking example of somebody who was like, You know what? Screw it. I’m just doing this right now, and I’m not gonna wait. I’m not gonna wait for permission from anybody.

I’m sure, and well, tell me if I’m right. Were people telling you no, you should go to school?

Henry: Here in Australia, it’s very common to go to college right after high school because it’s so much more affordable. It gets to the point where some people, it’s such an expectation that people just choose a degree to do or a course to do without really knowing. And some people switch two or three times throughout the undergraduate.

Using naysayers as fuel

Henry: So yeah, a lot of people were expecting me to go to college. I was a straight-A student up to the point where I decided not to go. I mean, I continued past that point, but at that point my principal and my teachers were all like, wait, what? Why are you choosing to do film let alone not go to college?

And yeah, there was some pushback. For me… I don’t know, like I’m like an all or nothing person. So when I get that resistance… I don’t know, it’s like a stubborn trigger in me that gets triggered and I’m like, you know what? I’m gonna use the frustration that I feel that people aren’t seeing what I’m seeing, or the resistance that I’m getting, I’m gonna use that as motivation to get it done.

Jessica: I love that. Yeah. Use that stubborn gene to just like push yourself through the thing. Did you have doubts at that point about whether you should be going to college, following the traditional path, or going out in the world? Or were you just like, yeah, this is fine.

I mean

Henry: I had doubts. Yeah.

Jessica: Whatever. So that’s a different brain place.

Henry: It was a different brain place. It was just fun. I mean, like, I remember there was a distinct point… It was two or a year and a half after I graduated high school and I’d chosen this path already, but I realized like, oh shit, I have to make money and where is that gonna come from?

So that moment did definitely happen, but the lead up to it there was just a lot of momentum that was happening with my career, even towards the end of high school, cuz one of the films that I made was screened and awarded in the US and I met a lot of my mentors, who are still my mentors now in that festival.

So it was just a lot of exciting things happening. So that sort of sped me along for a little while and gave me the courage to just do it without knowing. But there was definitely like uncertainty. This career pathway is obviously not… there’s no guaranteed path to success.

Not having a back-up plan

Henry: That was definitely on my mind a little bit, probably more on my parents’ minds. I didn’t think about it that much until after I’d made that choice. And I think for me, my philosophy is always like I’m gonna back myself into a corner and not give myself any backup plans, because then I’m forced to make it work. I specifically didn’t choose a secondary backup career. I didn’t.

A lot of my friends, sometimes, they were doing this as well at the same time I was doing it, and some of them had an, a different undergraduate degree that they were doing while they were trying to make this be the thing that they were doing. Just to have it as a backup.

And I was like, nah, I don’t think I’m gonna do that because then I can dedicate a hundred percent and I have no choice but to dedicate a hundred percent to this. So when I had that moment of realization, I was like, well, I better make this work.

Jessica: Yeah. No, I love that. That’s like, it’s really powerful, the idea of no backup plan. I think that’s really smart. It’s, I think would really make a huge difference to, it’s like you’re engineering your commitment.

Henry: Yep.

Jessica: And so even if you are gonna have doubts at some point you still are gonna be able to see it through. You have to see it through. You have no choice, right? You have no choice but to see it through. At least you perceive it that way. I’m sure, again, like people in their late teens and early twenties think a little bit differently about risk than people who are older, right? So I’m sure there were certain elements where you’re just like, whoa, this is gonna be fine. Where later you might have had other thoughts about it. And in some ways it’s good that you did it when you did.

Henry: Yeah, that, that definitely helped. I think back to that decision now. But actually even more than that, the decision to move to the United States.

Jessica: Okay. Wait, wait, wait. Let’s go in order here. So you won awards and you were doing, you were getting attention and found mentors through winning a competition in the United States. And then you immediately or later you started working freelance because you needed to make money to support your personal filmmaking work.

And then you moved to the US or you…? I mean, what’s the order there? How did that happen? So again, like guy in Australia up and moved to the US to try to make it.

Highlights of his journey

Henry: Yeah, so basically the highlight points of that journey is graduated high school, decided not to go to college. Did a lot of freelancing here between 2014 and 20 19. So five years. Didn’t make a lot of money. The industry here in Australia is– I mean, freelancing anywhere as hard as it is and especially at the beginning of your career.

But here in Australia it’s especially difficult cuz there’s no, not as much value put on the creative industries. There’s not as much money to go around. And so you have to fight harder and it’s for much less.

So that was an interesting, um, environment to come up in. And then over those years I also kept coming to the US just on my own trips. And whenever I’d come, I’d film little things from my own YouTube channel, which is where I host the series that I make Makers Who Inspire.

And progressively over the years, I think I came for four or five years in a row before I actually moved. Progressively the people that I was making films about grew bigger and bigger.

It went from like the first ones I made with people here, friends of mine in Adelaide, the city I’m from, and then in the US it got to like principal dancers at New York City Ballet or Ronnie Chieng, the Daily Show comedian. He’s also in Crazy Rich Asians and Shang-Chi.

What’s the worst that could happen?

Henry: So it, it grew that way and then eventually I was like, you know what? I’m not getting anywhere, uh, here in Australia. At least I don’t feel like I’m getting anywhere as fast as I want to be getting. There was progress, but not as fast as I wanted it.

But whenever I came to the US it was like, wow, there’s actually like people here who do this, value it, and they say that they can give me work. So I guess if it’s not working in Australia why not just give it a shot somewhere else? What could I lose?

And then I realized I qualified for a special like visa for artists. Went through the whole process. It cost like 16,000 Australian dollars to get that first visa.

I didn’t go to college, so that money was like, well, might as well invest in this and see how it goes. I used a lawyer who, you know, and people advised me, people who have the visa. I spoke to a lot of people before making this decision and they were like, we reckon you’ve got a very good chance. And I managed to get that visa, which was quite surprising under Trump as well.

And I was like, you know what, I will just go to the States, spend three months there and figure it out and come back to Australia if I need to. Left to go there in October, 2019. And around that time as well, ConvertKit, which is the company I have a full-time job with right now. I was connected to them through one of the mentors that I met in that very first film festival when I was still in high school.

He’s a producer at Disney. He did Beauty and the Beast, The Lion King. He connected me with them. He said, “Hey, congrats on the visa. I know this company wants to make the same types of films. They already have your films on their mood board, so why not just hire you to do it cuz they’re looking.”

So I connected with ConvertKit, went through this whole interview process that was quite extensive, actually more than it should have been for just a contract role. And it made sense later because after making a couple of films for them, they were like, you want to join the team full-time?

And I’m like, cool. We had a conversation about it. Of course I never thought I’d get a full-time job, but this company is incredible the way that they support creators. And their mission is to serve creators and the way they support the creators on their team.

So I was like, all right, I’ll join. And then the pandemic hits. And without that job, I wouldn’t have been able to, um, stay in the US. So I ended up staying in the US the whole time that I, for the three years essentially, that I had the visa. And I’m here to renew the visa, so that’s why I’m back in Australia at the moment. Yeah, that’s essentially the big plot points of the journey.

So moving to the US was also a decision that was like, not going to college, but bigger, I think. Because now I think about it and I was like, I would not do that now. Cuz it’s like, , no, that was, I was literally just gonna move and freelance. This ConvertKit thing had only happened like three months after I moved there.

But I, I just felt like I have a better chance in the States and I love America and there’s nothing happening here. So give it a shot, see what happens. And it, and it worked out.

The role of preparation and mentors

Jessica: So another point then. You raised a couple things that jumped out at me. One was you had these mentors, you listened to them, you kept in touch with them, and you were willing to use their advice to help support you through difficult decisions. So that’s number one. Relationships made a big difference.

Number two, you did a ton of research about this visa, talking to people, how it worked. You got a lawyer, you got professional help. You did jump into it not knowing what was gonna happen, but you didn’t jump into it like you just took a plane to the US and see if they’d let you stay. You know, it wasn’t like you, you were planning it, and like doing it intentionally.

Loss aversion

Jessica: And again, committing to that plan meant investing money, investing time, all those kinds of things. And there was something else that’s gonna come back to me, I’m sure of it, but hasn’t yet. But yeah, this, this idea that like you wouldn’t now, but you did then. I’m sure you don’t regret having done it, but like the person you are now, you might not have taken that risk because you know how risky, I guess, in retrospect, how risky it really was.

Henry: Yeah, it’s funny, I was talking to you about this, I think even when we met a few years ago. A couple years ago now, but I think this job, cause I’ve never had a full-time job until now and it’s, it was a learning curve to begin with, but I feel like I’ve settled into it pretty well.

But having a full-time job, I’ve got a, like a level of security and comfort and stability that I didn’t have before. And it was like, I think not having that kind of comfort and stability just made it normal for me to be like, You know what? If my bank account hits zero, it is what it is. And I might as well move. I might as well do this.

But now that I have that comfort and stability, it’s harder to imagine making that decision. So now the challenge is to still push myself in that way in spite of having all of this stability and comfort that I didn’t know before.

Jessica: That is so smart. Cause I think that’s really like, the loss aversion is such a huge part of not wanting to take these kinds of risks. That now you have something to lose that you didn’t have to lose before, which doesn’t mean you’re gonna stop taking these risks.

Cuz in fact you’ve taken huge risks and they’ve paid off. And I think part of having– the whole idea of courage before confidence is that you actually get confidence. The result of this is confidence because you do the thing and you go, oh, that was okay. Like, it was scary and it was a rollercoaster, but I did it and it had this result to it.

The power of courage to change your trajectory

Jessica: And I gotta say across the board, doing all the interviews with the Autonomous Creative and all this other stuff. And I’m sure, and we talked about this when you interviewed me for this ConvertKit film that you made. One of the most consistent things that every single person who I’ve talked to who’s successful says is, Oh, there was this time when I just started doing this thing.

I just started making this thing, and I did it because I wanted to do it, and because it was what made most sense to me creatively. I fully committed to it and I had no idea what was gonna happen, but that’s what opened all these doors. That’s the piece that five years later so and so found and did whatever it is.

You know, that was turned into this kind of opportunity that now makes my name. You get found, your work gets seen because you are out there making it, doing stuff. It doesn’t happen if you’re not out there doing stuff and you don’t know at first what’s gonna happen. You can’t know ahead of time. Right?

So it’s just impossible to predict that and set yourself up like rock solid boundaries and say like, this is absolutely gonna work. You have to be willing to put yourself out there a little bit. But the nice thing is that like people overestimate the risk of it. You know, they overestimate the downside and underestimate the upside.

I think the upside is huge and the downsides. Yeah. Stuff can happen. Tell us about your expensive mistakes.

Expensive mistakes

Henry: Yeah, it’s just like, business stuff that I wish I’d known. And I know now it’s like how to price things, how to read people. One of the most expensive mistakes was just partnering with the wrong person, like right outta high school.

People like, oh, he does film. I know someone who does film. Let me connect him with them. Someone I started working with seemed really good on the surface, but now in hindsight, I realize like he didn’t have a lot of his stuff together.

He was this guy, young dude who had a media company or media collective, and all he wanted to do with this was like take photos and make videos about clubbing or parties that he wanted to go to, or models that he wanted to go on dates with.

I remember the first thing he tried to, he got me to like do a sort of an exercise to audition for, like, the role was to edit for free this video that had been shot of this model that he was dating at the time just a walking through the botanical gardens, I don’t know.

And then I, I didn’t know, right? I don’t know anything. I’m like 18, so I was like, okay, cool. I’ll just do all of this. And then I started bringing real clients in like a hospitality company that manages like hotels in Singapore and like Melbourne and Brisbane. And, uh, like 20th Century Fox Promotions, they were promoting a movie called Spy that had just come out with Melissa McCarthy and they wanted to do some like activation video here in, in South Australia.

And he at, they didn’t know how to, like the guy running this company didn’t know how to manage those types of clients. And it got like, the communication and like the negotiation was getting a little bit sketchy.

Eventually, after a year or two, like we, me and a couple other people in the, company realized like, oh, this is not a vibe. Because like he had gotten us to do a bunch of stuff and it turned out that there was a lot of conflicts of interest in these jobs that he was getting us to work and he didn’t pay us, of course.

And he’d say things like, oh, I’ve already set the budget. If you need an extra shooter or you need an extra day, then you have to convince people to work for free. Those kinds of things.

Yeah, it’s just a lot of like sketchy stuff, a lot of very sketchy stuff. So I had to learn all those things the hard way, but I think everyone has to go through stuff like that at the start of their careers no matter whether or not they went to school. So those were some of those expensive mistakes.

Jessica: Yeah, I mean, I think learning how, like the importance of contracts and vetting people and getting paid up front part of your fee and all those kinds of things are… you can read books about that, but until you

Henry: Do it yourself.

Jessica: Experience it. Yeah.

Henry: Yeah.

Jessica: Yeah. Can you tell us about your pricing mistakes? Cause this is a common one.

Learning how to put lessons to use/Pricing mistakes

Henry: Pricing? Yeah. I mean, I’m still figuring out pricing.

It’s funny sometimes now, like I still– ConvertKit, encourages you to do side hustles, you know, outside of the work that we do at the company full-time. So I’ve done a little bit here and there over the last few years where I can fit it in. And some people ask, still ask me to bring the price down a bit. But I still, I’ve got other people who are like, you’re charging too little. And I’m like, what?

So that’s still something that I’m figuring out. But pricing mistakes to begin with… just, I don’t know, like charging far too little and not factoring in all the things that would go into it. And, and clearly saying, okay, this is including only like two revisions or three revisions or whatever.

There were times where I went to like seven or eight revisions on a video or something cuz a client just wasn’t on like a birthday event video because a client really wanted this or that. So, so learning how to like

Jessica: So boundaries.

Henry: Boundaries is important also what I found that’s really helped me, and I’m still doing it right now, is tracking my time. I know it’s, it’s a little bit like… it’s counterintuitive sometimes, but I run a timer when I’m editing and of course when I’m on set, I know how long I was there.

And then I enter it into a spreadsheet and the spreadsheet calculates the number of hours that I worked on the job and like divides it by the total amount I got paid or whatever to show me the hourly rate.

And that helps because it, it helps me keep track of how long things take. Now I, if someone asks me to do something that I’ve done before, I can go and look and be like, okay, it’ll take this much time. So I know how many hours to quote for it.

But it also makes sure that I can sort of refer to that to see if I’ve been getting the hourly rate that I had set out to get on that particular job, because it keeps me accountable. So just tracking your time as a freelancer, that kind of stuff is, it’s very important.

Creating a savings account, separate savings account, to put money into for taxes, factoring taxes into it. I think everyone’s gotten hit with like a tax bill at the end of the financial year that was more than they expected because you never think to do that.

So things like that. They don’t teach you that kind of stuff even at school here, like if you go to college here, it’s like they don’t teach you that, which is a problem that I have with the system here. They cultivate a mindset of dependency on external factors to get success when they should be teaching creators business and all of the logical logistical stuff like that.

Jessica: Yeah, it’s tough. I mean, I’ve been teaching in art school in the US for 20 plus years now and it varies what students get depending on who’s teaching the professional practice class, but usually it’s just one class, and it’s very hard to fit all that stuff in. And yeah, I mean, I think that stuff’s so important.

I teach professional practice. I’m starting my professional practice semester on Tuesday so I just am revising my syllabus. And my syllabus is full of like business model and financial, whatever.

And, but I’ve taught this class like four or five times, and the students… I think they get a lot out of it, but it’s more like an overall sense that there’s stuff you need to know and do, which is good, but like the specifics of it are just like, they just are not, it’s too fast.

Courage to brave the Gap is the only way you get to the other side

Jessica: Like you need to have much more immersion in this and in some ways, you have to have that on the ground experience. And this is the other piece of this is like… Ira Glass talks about the Gap, right? The gap between your taste and what you envision for yourself and for your work and what you’re actually able to do. And that the only way through the Gap is to make a lot of stuff. Just keep making stuff.

And I think that’s very true. I mean, the Idea Debt concept that I teach about and the Creative Focus Workshop and elsewhere where people sit with all these ideas and they kind of mull and stew about all these things, but don’t actually finish and complete and move on to the next thing and the next thing and the next thing.

A lot of it is about perfectionism. Thinking like you can somehow, again, future proof. If you just nail down all the details, it’s gonna be good enough to get out there and be bulletproof. Nobody’s gonna be able to criticize it.

And you’re gonna get all the way to the other side of the Gap, the big gap, that way instead of by the painful iteration of project after project birthday party videos and whatever

Henry: weddings

Jessica: That you weddings that you need to do in order to get to an award-winning documentary series. Like you, you have to be able to go through this stuff on the way. That’s the only way to get to the other side.

That’s why at an essential level, that’s why courage before confidence is so important is because that is how you actually get to be the creator you wanna be. Aside from the money part and the recognition. And while all that stuff also comes as a result of taking risky steps with your creative work. But at a basic level, just making the work you wanna be making doesn’t happen unless you’re willing to just commit, do it, finish, move on, keep going.

I’ve been looking through all my old stuff, getting ready to donate a lot of archives and things to an archive of comics related stuff. And, you know, I look at my stuff from, I dunno, like 98 or whatever.

Henry: Yeah.

Jessica: A little horrifying, but if I hadn’t done that, I couldn’t have done what I did later. It’s just not, you can’t go from one end to the other end. You have to go through, through the middle and at the time those things were things that I was proud of and happy with.

Being out there with your work is how you make connections that matter

Jessica: You know, and I said like, saying yes to… another piece of this is, I think saying yes to opportunities that come up. Like saying yes to ConvertKit, saying yes to your very first festival that you entered.

Seeing the, the poster and saying like, I’m doing that. One of my big ones is saying yes to doing non-fiction comic strips in the Newcity, which was a tab– is a tabloid newspaper in Chicago.

And they had me go out and cover like, what was the first one I did? I think it was Elizabeth Wurtzel, Prozac Nation, which was like a very, like, it was like the hot book of the time. And like everybody’s scuttlebutt, whatever.

And I went out and covered her like, her reading and like interviewed people and did like a man on the street thing. And I did those strips for the Newcity.

Hmm. Two, three times a year for a few years. And one of those ended up in Ira Glass’s. filing cabinet, which is why three years after that he pulled it out and looked me up in the phonebook on paper by the way, paper phonebook. That’s how old I am.

Looked up me up in the phonebook, called me, and invited me to collaborate with him on the first radio book that I did, the Radio: An Illustrated Guide.

So saying yes to this thing that was like, I don’t know how to do this. Oh my god, I dunno. And like saying yes to Ira Glass when he says, Do you wanna collaborate with me? You know, it’s like, in some ways it’s a no-brainer, right? You’re being asked to do something, but I wasn’t, it’s not like I was paid a lot for the Newcity strip.

It wasn’t aligned with the fiction work that I was doing, but it just opened doors, you know, it made opportunities available to me. and I’m really, obviously very happy that I did that.

Henry: Yeah, some of the, um, the benefits of the series that I was making was that I got to meet a lot of artists. People that I looked up to and then have conversations with them personally when we weren’t shooting. Even when we were interviewing, a lot of the questions I was asking them was stuff I wanted to know.

But in our own time, we talk as well. And some of the best advice that I got is from a painter, a really successful painter, and he was saying you never know who’s looking at what you’re making, even though it might like get only 5,000 views or whatever.

And he was right because there’ve been many times people have connected with me in the last few years and they said, oh, I saw this thing that you did. And I’m like, really? That?

like this guy Johnny Harris, he’s a big YouTuber now, used to work for Vox, and he does a lot of things on his own channel with the New York Times and other stuff now. I like his work. I’ve always sort of watched what he did and he started this travel company and he’s getting other people to make videos, contribute to the YouTube channel for this travel company, course company.

And yeah, they reached out to me and I’m like, how did you find my stuff? And it turns out his wife was watching, who’s also a YouTuber that I watch, both of them had seen my, my films from years ago. So it’s weird.

Jessica: It is weird, but it’s, it’s also like, it just shows… having a huge audience isn’t always what makes the difference. It’s having

Henry: The right people see it.

Jessica: You know, an audience who cares, an audience who, you know, in this case, it’s like the right audience in that this is somebody who’s influential.

Living with the unknowing of what’s gonna happen

Jessica: That’s not always the case though, but it’s like people who really care about your work, that’s gonna make a ton of difference. And I mean, you just never know what comes out of it, right? You never know what’s gonna happen. I think one of the biggest things for people who are trying to figure out how to like step forward boldly is that fear of the unknown. Like, what is gonna happen? I need to know what’s gonna happen.

And you have to live with the unknowing and just like, let it be out there. Let your early work be published still. And all of those other things. And be visible, be seen, have your, like the, your trajectory over time be traceable. All of those things are, they can be difficult for people. They can be hard for people to sort of face that, which I very much understand.

Balancing paid work and personal work

Jessica: There’s one other thing you mentioned as we were getting ready for this interview or for this conversation, where you talked about how one of the big things you’re struggling with at this point is that you do work a full-time job doing what you love. Making films about creative people, but that’s made it difficult for you to have this side hustle and do your own work because it’s like the same thing.

This isn’t really about the topic, but I just think it’s an interesting topic that comes up a lot. And I liked your… you have this advice from Don Hahn who’s your, your mentor, who’s helped you in a number of times through your, your career to have a hobby or creative passion that has nothing to do with what you do at work.

How does that play out, what are you doing in that regard?

Henry: Yeah, he gave me that advice cuz I was trying to make a documentary for myself, personal documentary, while I was also making documentaries at work. And he said like, this is why I don’t do film stuff. He produced, he’s the producer who did Beauty and the Beast, The Lion King. Nightmare Before Christmas. He’s done a lot of Disney movies.

He says, “This is why I don’t do any film stuff at all. Like in my own time.” Whenever I go and visit his place, it’s like a painting studio. He paints. So he is like, this is why I paint cuz like it just, has nothing to do with it. I can relax and I can still enjoy it, blah, blah, blah. Now like for me, those things are film photography.

It’s still camera related, so it’s not as different as it should be, I think, but it helps quite a bit. It’s not cheap, but the film photography stuff, if you are into it. That helps for me.

I also have really gotten into cycling. Just biking around New York. That’s a lot of fun. It’s become one of the core parts of my identity in the last couple years. So those two things together, I’ll take the camera out for a bike ride. That really helps.

I’m considering taking up like archery or something really random when I get back to the city. Maybe something recreational like that too, but

Jessica: Mm-hmm.

Henry: Yeah, that was some really good advice that I got from him.

Jessica: Yeah. No, I like that. Cause I, one of the things I realized that part of my… my motto when I was in my twenties was dare to be bad. Do stuff and be bad at it, and that’s okay.

But what it kind of led to that and just continually creating stuff and trying to get it out there was instrumentalizing, like basically everything I was doing. Every time I’d be like, I’m gonna make a print that isn’t, doesn’t have to do with my comics. I would be like, Hmm, it’s gonna be an ad for my comics. I’m gonna make a poster for my comic. Like, I’m gonna do some painting. Oh, that’ll be a cover for my comics.

I was taking everything and kind of feeding it into the comics with the result that I kind of didn’t keep doing those things, you know, as sort of they dropped off. So I feel like that’s, it’s like part and parcel with enthusiastically making everything, getting everything out there, still have to create space for these other… the other kind of work.

Henry: One, one. One of the things that the founder of ConvertKit has said to me, Nathan, he says, he said something really wise recently. He said, “When your output is tied to your motivation, then that doesn’t usually work because when there’s a slump in your output, then you lose your motivation so you need to find other ways to motivate yourself.”

Jessica: Yeah. Yeah. That’s very smart.

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What do you do when you’ve been courageous, gotten out over your skis, and find yourself unable to deliver on your plans?

Jessica: All right, so we’ve got a bunch of great questions. So I’m gonna grab those and let’s see what we can do with them. All right, so Syne asks, what do you do when you’ve been courageous, gotten out over your skis and find yourself unable to deliver on your plans? What do you think?

Henry: Hmm. Trying to think back to when that happened. I don’t know. It just, it sucks. I always think that I would rather try than not try because if it’s like, at least then I can see I tried.

Whenever it’s like, whether it’s a festival or lost opportunity with a… like, I didn’t get into a festival I wanted to get into the back when I was doing that. Or like, I pitched for this job and put in a lot of this time and didn’t get the project or just visa stuff, which is some of the stuff that I’m going through right now.

I’m glad that I at least tried because then I can say that to myself. And then you just gotta look at what worked and study what didn’t work.

You know, have that like couple of days of feeling bad for myself, and then I’ll sort of figure out what can be done next. I prefer to put things into action and, and not just sort of sit around and think about things too much sometimes because if there’s something that I can control and something I can do about it, then I feel better.

So yeah, like part of it is like just thinking about what you can learn from that situation and what can you, can do differently next time and use that to push yourself into something again in the future. And, and hopefully it’ll turn out better because you’ve learn something.

Jessica: It’s one of those terrible cliches, like there’s no such thing as failure there’s just like learning experiences which

Henry: It’s difficult when money’s involved though.

Turn stress into excitement: use it as fuel

Jessica: Let’s not go too far with that. But yes, I get the basic of it. My feel, my thought initially was a few things. I think that, first of all, I would say my first reaction when I’m like, oh, things are going sideways, is to go into improv mode. And just like figure something out. Like it’s the adrenaline kicks in.

And, um, this happens all the time, like in a classroom situation or a coaching situation or something where somebody asks a question or needs something or does something where I’m like, oh, oh, we gotta deal with that. And I’m just kind of like moving through. And I actually really enjoy that kind of excitement and stress, like that performance stress.

And one of the things I wanted to make sure to mention is, I mean, obviously you’re here probably cuz you’re thinking about some stress and anxiety around courage before confidence and getting out there. Try reframing that stress and anxiety as excitement. Like pre-performance excitement, that you’re like, oh, this could be really, uh, weird, ah!

You know, and like get yourself kind of hyped up to do the thing instead of looking at it as like, oh, that’s a bad sign. I should relax now. I need some tea.

Use it to fuel you as opposed to using it as like a explanation of why you’re not gonna do the thing.

I think that’s the, the energy I get into, if I’m on stage and the tech isn’t working or something. I’m like, all right, I’ll just yell. and You know, I just will do something. That’s one kind of fixing the situation. Doesn’t always work, not always appropriate. So I don’t always do that.

Communicate and renegotiate

Jessica: The second thing though is communicate and apologize. If something’s going, I’m not able to deliver, that I can’t finish on time or I can’t finish at all, or I realize I’m a totally bad fit or like something like that.

One thing I try to do, and boy is it hard is to communicate with whoever I’m doing this thing with or for, and just tell them what’s going on and be totally honest about it.

And if it’s something like you were saying earlier, Henry, with like somebody who’s like a bad collaborator or whatever, I’m just gonna be like, I’m out. I’ll try to come up with some very nonpersonal way to talk about it, but I’ll just be like, ah, things have come up and I’m gonna be, you know, and just get myself out of the situation.

If it’s my fault and somebody’s waiting for me, then I just try to really communicate, renegotiate, and like I’ve dealt with so many people who don’t, that I just feel like I’ve been burned so much as the person who’s waiting for something that I just try really hard not to let that happen. And that communication will fix so many things.

Just apologize for being late. Don’t overexplain. Don’t make them feel like they need to make you feel better. Like, don’t put it on them. Just say like, Hey, I take responsibility. How can we move forward with this? And yeah, that’s what I try to do.

Henry: That’s a good answer. It applies to some situations that I’m in right now too. I’m

Jessica: Exactly.

All right, so Kate says, how do you know which projects just need courage and to dive right into, whereas some projects need more time to incubate. How can you tell which ideas are ready enough to get going on? Good question. Kind of personal individual, like depends. But what do you think?

How do you decide if a project is worth pursuing?

Henry: I mean, I’m still figuring that out as well. Like I said, that film that I was trying to make while I was doing my work at ConvertKit, I thought it was a project where I just have to dive right in and just make it happen. But then at a certain point I realized like I don’t have the perspective to be able to give the film what it needs currently.

It’s okay to put it to the one side for the time being. It’s always gonna be there if I need, if I want to complete it again in the future and it can only benefit from some time to age well. So I think it’s a process that.

Take time to assess

Henry: It’s a learning process and it’s something that you, I think for me, it helped when I was like, I sat back and I sort of tried to stop thinking about what was actionable about the project and really think about how it was making me feel and what I was really able to give to it, and whether that was benefiting me or, or whether it was benefiting the project. And I realized like it wasn’t, so that was something that helped me realize like, oh, this is something that I, that needs more time instead of just brute force.

The value of an action bias

Jessica: Which is tough like you and me to acknowledge that. I think we’re both a little bit brute force people who kind of roll through stuff.

Henry: Yeah.

Jessica: Yeah. I mean, I, I just, I encourage with everybody, I encourage an action bias and knowing that it’s okay, like to get back to the previous question, to connect us to the previous question, it’s okay to start something and then stop, like you just were talking about.

It’s okay to recognize that like, I am out there, but I’m not really ready for this. And even if it’s in public, to publicly put a pause on something if you’re releasing a web comic or you’re doing a series of something and you’re like, I just need a break here. Again, just transparency makes a ton of difference.

And we also, I think, always overestimate how much anybody else cares about how fast our stuff comes. It’s very rare for somebody to care, like, Hey, where’s your next episode of whatever? That’s just not that common.

Henry: Also look back at the stuff that you’ve made in the past. If there’s anything similar and think about whether or not that required more time or whether it’s something that you could just go ahead and do without thinking about too much. That helps. That’s how I sort of judge what a project needs to begin with sometimes as well.

Jessica: Yeah. Although if it’s something new, you won’t necessarily know.

Henry: Yeah. That’s when you have to figure it out.

Jessica: Yeah. But also I think that, and I think that can be a little bit of a trap if you’re like, oh, well this thing I did in the past, I could have used more time on it because you did it when you were younger and you like you could do better now.

You have to be able to like kind of put yourself in this sort of, given what I had then, was this the best I could have? You can’t get yourself in a situation, you just mustn’t get yourself in a situation where you’re thinking like, oh, if only I’d waited on this project that I did when I was 30 and did it when I was 40.

But then you wouldn’t have been able to do the stuff when you were 40. You know, that’s not possible. It’s apples and oranges in that sense, and that’s why I think action bias is so important just to be like, you know what? I’m just gonna do it. Whatever. What’s the worst that could happen?

It’s a good question to ask yourself. What is the worst that could happen? Honestly?

Henry: Exactly.

How do you calculate the risk?

Jessica: Okay. So Katie asks, for your expensive mistakes that you made in your early career, how did you calculate what was worth the risk? And I think that we already looked at that a little bit, where it’s like you weren’t, I don’t know how much you were calculating the risk. You were just doing stuff and then figuring out, oh, that wasn’t so great

Henry: Hmm.

Jessica: Were you?

Henry: I mean, all of it was worth the risk because I learned something from it. Honestly probably it was the ones that were the mistakes and didn’t work out probably were worth more because it showed me what I shouldn’t be doing. Or something that needed to change.

I don’t know, like at a certain it’s helpful to do a retro after something doesn’t work or when something does work, obviously, but at a certain point it’s not helpful to keep calculating. So I give myself like a week after the project’s done to reflect on it and, and write if and if it helps, you know, journal about it, all that stuff.

And then after that, I generally don’t return to it for a little while because I don’t want that to be occupying a part of my brain that could cause doubt for another project that I was doing.

Reflecting, using debriefs

Jessica: Yeah, I’ve started writing debriefs on most of my projects. I try to remember to do it where I write here’s what happened, here’s what happened. And I, I use the question, so what? Like, here’s what happened, so what? Well, this is what this means. This is the takeaway from whatever the result is.

So Katie’s actually asking about real numbers also, like, how much money do into projects for how long before they start to see money back? What kind of investment seems worth it?

It’s the kind of thing where, like for me, with a business project where I’m like releasing a course or something like that, I’ll write like, well, here’s how much time we put into this and here’s how much financial investment we put into it. Here’s what we got back.

What’s the level of profitability on this thing? And then so what? Does that mean we don’t do this again? Does it mean we do it differently? Does it mean it was good and we can do better? Like try to get takeaways from, from big projects. Like if we’re doing big projects, I will, I always try to do that.

Henry: Yeah.

Jessica: I think you doing, spending $16,000 on immigrating to the US that’s an investment.

Henry: Well, yeah, that was worth the risk because the money I earned while I was in the US is far exceeding that. But that, I mean, calculating? Okay then, that’s something I knew when I moved to the US. I need to make at least $16,000 to like, make this worthwhile outside of the money that I need to make to sustain my life.

So that was something that I knew, that’s what I calculated. But sometimes it’s difficult to figure out what the actual metric number is, whether it’s amounts of money and whether that was worth the risk or whether it’s like a return on investment based on the metrics that you get on impressions and trafficking, engagement.

Anything with that kind of stuff. Brand content is very difficult to calculate. So at a certain point you have to be comfortable with just having risk, I think.

Jessica: And when, when you’re working solo, a lot of the, what you’re investing is time, most of the time. More than money.

Henry: Yeah. That’s why I calculate my time. I measure it and I’m like, that’s honestly something that I calculate more when it comes to like the question, like calculating the risk than money sometimes, because it’s like is that valuable use of my time? And if not, then I know how to do it again.

Jessica: Yeah. Yeah. Hard won lessons for sure.

How do you overcome self-doubt?

Jessica: All right, so Ray asks, how do you maintain the result to see your creative endeavors through in the base of uncertainty?

Let’s see if I can boil this down a little bit. Even though people are at the heart of what I wanna co-create, I regularly get into staring contests with doubt, with a pervasive and invasive question of what if people don’t want what I offer.

And the juxtaposition between wanting to create for the sake of myself and others and said, creativity, needing to sustain me and being able to afford access to resources I need, not just survive, but thrive.

Henry: The resources to survive and thrive is the part that’s challenging.

Jessica: Yeah.

Henry: For me it was… I didn’t, like I said, cuz I just graduated high school. It was something that I didn’t have to think about for the first year and a half or so. And then by then I was so deep into it that I had no choice but to just keep going.

Jessica: Well you did. You could have just gone to college or something.

Henry: I guess, yeah, you’re right. I don’t know. I think what I’ve found is I’ve always found that the amount of doubt is never, and it’s never as bad as you think it, it is. I think generally people at risk averse, you know.

Even if you’re not a risk averse person, people are always kind of risk averse and conservative and worried because that’s the way that we’ve been bred to be, to ensure survival.

But what’s the, what’s the worst that could happen? I think that’s the question.

Jessica: Right. It is.

Henry: I mean, you’re right. I could’ve just gone to college so that, that’s the worst that could’ve happened. I could’ve changed jobs. I could’ve moved back home. I could moved back home, changed careers. And that’s, that feels like the end of the world to me right now. But like, it’s not the worst thing that could happen, I think.

Jessica: I mean, who knows? Like it, it’s an entirely different life. Who knows what it would look like? It could be great. Better or worse, I don’t know.

Henry: Yeah. But generally, I found that it’s actually the opposite. Whenever I’ve gone and done something the return on investment’s been way higher than I expected, and the risks sometimes don’t even manifest.

You can never know unless you put it out there

Jessica: Yeah, exactly. And I mean, I think that the key thing that I read in this question is, uh, get into staring contests with doubt, with a pervasive and invasive question of what if people don’t want what I offer? You are never going to know unless you actually try. You will never know if people want it or not if you don’t try it.

No one has the opportunity to want it if you don’t put it out there. Nobody can tell you anything and you can’t learn. Sure. The first time you put something out, you may not get the response you want, but then that’s useful. That is truly useful information. You know, if you get yes, this, not that, or like, oh, I really liked this part, but I couldn’t commit cuz of blah, blah, blah.

Like, that is information you could use. If you’re trying to create an offer in your business that will work you have to make offers and try them. You have to get them in front of people and get responses whether or not it’s gonna land. That is the only way you’re gonna, you can’t design your way out of this problem.

Henry: And oftentimes you have to stick with it for a little while as well because like the first time that you put it out, I mean, you haven’t built the following or the foundation or people aren’t expecting that on the first one. So like it’s only gonna grow from that point. And that’s what I found with a lot of the work that I do on my own as well as at ConvertKit.

So ConvertKit really understands. Yeah. Like it’s gonna take, especially for brand content, a good amount of time before we can expect to see a return on investment in terms of like traffic and engagement alone. So it’s like you have to stick with it.

Jessica: Yeah, you gotta stick with it. And I mean, I think that you take feedback from whatever happened and you modify how you’re putting it out there. But yeah, I mean, you have to just, you have to trust that you know enough to start and then you can kind of go from there essentially.

Hype yourself up

Henry: It helps to hype yourself up too.

Jessica: Yeah.

Henry: To sort of look at what you are doing and realize that you are an expert in many ways that other people don’t and they can’t see the vision that you can see. So that’s sometimes what I do to, when I’m experiencing doubt and, and specifically creative doubt around my, the output or the stuff that I’m making.

Jessica: Yeah, people can’t see it, can’t see your vision, and they definitely can’t see your vision unless you show it. If you don’t put it out there, nobody gets a chance to engage with it. That’s just the end of the story.

Henry: Yeah.

How do you decide if a project is worth pursuing?

Jessica: All right. Amy says, what helps you de decide a project is not just a good idea, but really worth pursuing? And conversely, what helps you decide when a project has run its course?

Henry: Could you read the first part of the question again?

Jessica: What helps you decide if a project is just not a good idea. Or is not just a good idea, but really worth pursuing. And conversely, what helps you decide that when a project has run its course, like when do you stop? Like when do you look at something and you go like, oh, this is really, this is worth it, versus, hmm, maybe not? Do you have any sense how to navigate that?

Henry: I think preparation helps. You give yourself this amount of time to make this thing and see if it’s gonna work. But how do you decide what the amount of time is that’s appropriate to set as the, as that period? So talking to people who might know, for me it’s like mentors of mine, producers who’ve had experience in this field, you know, that kind of thing.

And then you give yourself this amount of like runway and then you’re like okay, these are what I want to see. These are the definitions of success for me to be able to keep running with this past this runway. And yeah, just commit to making stuff for that period of time. Like it’s like we just said, I think it takes like a little while for something to see whether or not it’s working or not, or to get the kind of like results that you want to get from it.

So giving yourself that amount of time and just committing to making the stuff for that amount of time, it helps. That’s what I did with the series that I was doing. And I was getting the results that I wanted in terms of, which was all I set out to do was just make the work and show myself that I could do it.

And also, um, get some views on that, on them in YouTube. But not only did I get that, I also got like better and better quality people that I was making films about or hire, uh, more famous people essentially. So I was like, okay, this is something that’s working and not you running with it.

Creative Engine, does it keep you interested?

Jessica: Yeah. And I think too, like you can do small test pieces of what you’re doing potentially and like put it in front of people. I judge it partly by like that whole, so I teach this framework called the Creative Engine and the first stage of the Creative Engine is Collect, which is basically research, figuring out like what’s in it, what are you gonna do, and then Decide. What are the, what are you actually gonna focus on and what’s the core of it, and all those kinds of things.

Then Act and then Reflect. So you go through this cycle, right? And so in collect phase as you start making decisions about it, if you keep getting more excited about it, even if it feels really scary and like too big, then I think it, for me, it feels like a good idea. Then I’m like, this keeps coming back.

This keeps coming back to me and I keep thinking about this thing. I think it’s a good idea, like I think this is, it has legs. For me personally, whether it’s gonna be a good idea in the world or not, I can’t know until I get further into it, but at least if it’s gonna sustain my interest and challenge me, then I know it’s worth at least the next step of investment.

Henry: Yeah. And also, I mean, that’s a good point. Be excited about it. Yeah. When I was making these films, I couldn’t wait. Even no matter how late I got home after the interview, I just wanted to edit the interview cuz what they said was so resonant to me. That’s how I knew that it was personally sustainable because I was excited about it. And with anything creative, if you’re not excited about it, I think people can often feel, feel that, or it doesn’t connect in the same way.

Jessica: And especially when you’re doing the things, the projects that are gonna be your personal projects, you’re gonna put out there in the world using courage, daring to be bad, all that other stuff. Those things are the bridge to the future opportunities that are gonna come rolling your way.

And if you can’t feel enthusiastic about that work and show your enthusiasm through the way you shared it and like, you know, the content of the work…people are, they’re not gonna read that it’s important to you, and they’re not gonna read that enthusiasm. And that’s such a huge piece of like, sort of the storytelling around the work is your love and passion for it.

I mean, it can be very, very weird work and you can still find an amazing audience if you’re like super into it, you know, and just kind of show that you’re really into it and you know, you have to live with it for a very long time. So going inward and, and sort of figuring that out I think is super important.

Henry: And you can still be enthusiastic and have doubts at the same time. Just because you’re having doubts doesn’t mean you’re not enthusiastic. There’s a separation between them.

Jessica: Yeah. Very much so. Very much so. All right. A couple questions about practical steps, which I think covered quite a bit. Yeah, I think we basically covered it here. Those were great questions you guys. Thank you so much for bringing the questions and showing up live today. Henry, thank you for being here with me for Creative Business Design Lab.

Henry: Thank you. I appreciate the opportunity.

Jessica: Yeah, it was really fun and just such a great conversation I think. I am very happy to have this like topic, just to be able to dive into this topic because it’s just such a fraught one, but it’s, it’s the pivot point between dreaming and doing, you know. It’s the pivot point between like imagining something and being the thing. This is it. This is the thing that makes the difference, honestly.

Henry: I hope it helped. Yeah, I feel like we could have talked about so much more as well, but it’s like there’s only so much you can cover in an hour,

Jessica: There’s only so much people can absorb. We’ll just have to come back

Henry: Oh yeah, that’s true.

Jessica: I’ll invite you back.

All right, thanks a lot. See you next time.


Jessica: Thank you so much for joining us today for the Autonomous Creative.

Our show is produced by Matt Madden, our production coordinator is Lousine Boyakhandjyan, and our production assistant is Rhiannon Sunday. Music is by Matt Madden, and I’m your host, Jessica Abel.

You can find all our takeaways as well as any links and extras we mentioned today plus transcripts, in the show notes. Find everything you need at acpod.show.

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We appreciate your help so much. And we’ll see you next time on the Autonomous Creative.


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