As someone who has been freelancing for almost 40 years – I just turned 60 – it can often be a frustrating career (especially these days) but never a boring one. I'm glad you made that decision to quit your job 21 years ago. (Though I'm a little pissed off that you can draw AND write. Bastard.)
You obviously chose the right path for yourself and all the people you've entertained for that time -- and the world will continue to need and support people who are really clever and really funny.
I really appreciate your creativity and tenacity, Jason❣️ Good for you! You’re incredibly talented and I like how you engage! I was self employed and I wish there had been more financial security. It is good for you to think about this and to squirrel 🐿️ money away. I don’t know why the world seems to think it’s ok to ask artists to go to bat for free! It isn’t! I don’t know your financial situation, but make sure you get paid properly! Enough of the ‘exposure’ nonsense! Come on everyone…realize how important art is and help support $$$ the arts! It’s paramount to all our health and welfare!
I love this: "At my FIT guest lecture earlier this year, I told the students that freelancing is like trying to build a parachute after you’ve already jumped out of the plane. You’re sewing panels together mid-air, hoping the thing opens before rent is due. After two decades, I like to think learned how to fall with slightly better form. But who knows?"
It reminds me of this line from Chögyam Trungpa Rinpoche “The bad news is you’re falling through the air, nothing to hang on to, no parachute. The good news is, there’s no ground.”
I love that you read Chögyam Trungpa Rinpoche. I came to them through Waking Up— I had this on the wall of my studio last year:
“All our past history and all our neurosis is related with others in some sense. All our experiences are based on others, basically. As long as we have a sense of practice, some realization that we are treading on the path, every one of those little details, which are seemingly obstacles to us, becomes an essential part of the path.
Without them, we cannot attain anything at all—we have no feedback, we have nothing to work with, absolutely nothing to work with. So in a sense all the things taking place around our world, all the irritations and all the problems, are crucial. "
Freelance IS daunting. Arnie and I got married when he was just doing medical charts, Kano shades erc., but fortunately the newspaper and magazine business was thriving and his portfolio showings began to get jobs. But the crazy thing about freelance is if you get one job you get three, so lots of work or none. It requires so much discipline.
In the beginning when the jobs were just little “spots” in the middle of magazine back pages, my mother kept all the magazines and placed them all around the living room open to the page Arnie’s work was on!
We wish you all the best. You have so much talent and we know you love being “boss”.
Brillant reflection on the freelance life. The parachute mid-air analogy captures someting most career advice misses - that uncertainty isnt a phase to endure but the actual terrain of creative work. What's inetersting is how the identity shift happens gradually, from 'freelancer struggling without structure' to 'professional who's internalized their own systems.'
All I have to say is that you look darn good for your age. I also wanted to share the reason I have a paid subscription to you all. I looked at the news I receive on Substack and I needed some humor to go with the sadness of the news I read. I thank you for lightening up my spirit. 'Berta
Great piece, as usual, Jason. Somehow you manage to make it seem pleasant. From my experience, it is! I've been freelancing since 1978 (not a typo), and one recurring question from W2 recipients: "How do you cope with the uncertainty of not having a regular paycheck?". My answer was that I manage money a lot better when I didn't know exactly when I was going to get any. Keep up the great work, my friend.
Beautifully said - my 60th year and still building that parachute - so glad I did it and still am. Clearly you have all the right tools to keep building. Cheers!
This is an amazing description of what it must be like to be a freelancer. As a high school art teacher for the past two decades I don’t know what that life would feel like but at least now I can share your description with students who might think about being a freelancer with their art skills. Thanks Jason!
I can remember my late bf, James (he passed in 2016) telling me how just after had the money to buy his house- the TV show he was on got cancelled. And when I finally moved into my home in my late 20's, I lost my job on a TV show... and I panicked, not certain how I'd pay my mortgage or anything. I was pretty young to have gotten where I did by 28 in the world of TV production... and then all of a sudden I was just shot into the world of freelancing. And that concept of building the parachute as you freefall is so relatable to me. I changed my career path completely in my 30s, sold my home and started waitressing. And I soon got into comedy and started on my path of documentary filmmaking... and all of this is to say, I've found a way to dance as I free-fall. I like how my life is a bit here and a bit there. I'm creating all the time. It's a way I couldn't imagine not living... and to think when I started on this path, I didn't know how I'd live. Growth, baby! Growth. :)
Love this perspective. That parachute metaphor captures the freelance grind perfectly, especially the part about trying to sew it mid-fall. The identity piece is underappreciated too, when theboss and the employee are the same person perpetually negotiating with themselves about deadlines and vacation.
As someone who has been freelancing for almost 40 years – I just turned 60 – it can often be a frustrating career (especially these days) but never a boring one. I'm glad you made that decision to quit your job 21 years ago. (Though I'm a little pissed off that you can draw AND write. Bastard.)
😂😂
Hahaha. Thank you Bob.
I’m just a baby compared to you in the freelancing world! Hats off to you for 40 years!
You obviously chose the right path for yourself and all the people you've entertained for that time -- and the world will continue to need and support people who are really clever and really funny.
I really appreciate your creativity and tenacity, Jason❣️ Good for you! You’re incredibly talented and I like how you engage! I was self employed and I wish there had been more financial security. It is good for you to think about this and to squirrel 🐿️ money away. I don’t know why the world seems to think it’s ok to ask artists to go to bat for free! It isn’t! I don’t know your financial situation, but make sure you get paid properly! Enough of the ‘exposure’ nonsense! Come on everyone…realize how important art is and help support $$$ the arts! It’s paramount to all our health and welfare!
Keep up the good fight, Jason!
Thank you so much, Elisabeth. I appreciate your support so much. It means a lot.
Dear Jason,
Congratulations on 21 years!
I love this: "At my FIT guest lecture earlier this year, I told the students that freelancing is like trying to build a parachute after you’ve already jumped out of the plane. You’re sewing panels together mid-air, hoping the thing opens before rent is due. After two decades, I like to think learned how to fall with slightly better form. But who knows?"
It reminds me of this line from Chögyam Trungpa Rinpoche “The bad news is you’re falling through the air, nothing to hang on to, no parachute. The good news is, there’s no ground.”
Happy art day!
Love
Myq
Thank you, Myq.
I love that you read Chögyam Trungpa Rinpoche. I came to them through Waking Up— I had this on the wall of my studio last year:
“All our past history and all our neurosis is related with others in some sense. All our experiences are based on others, basically. As long as we have a sense of practice, some realization that we are treading on the path, every one of those little details, which are seemingly obstacles to us, becomes an essential part of the path.
Without them, we cannot attain anything at all—we have no feedback, we have nothing to work with, absolutely nothing to work with. So in a sense all the things taking place around our world, all the irritations and all the problems, are crucial. "
I love it, thank you for sharing, my friend!
Great thing to have on your wall!
It is valuable to remember sometimes that the obstacle is the path, that every difficult person and situation can be a teacher.
I appreciate you!
Freelance IS daunting. Arnie and I got married when he was just doing medical charts, Kano shades erc., but fortunately the newspaper and magazine business was thriving and his portfolio showings began to get jobs. But the crazy thing about freelance is if you get one job you get three, so lots of work or none. It requires so much discipline.
In the beginning when the jobs were just little “spots” in the middle of magazine back pages, my mother kept all the magazines and placed them all around the living room open to the page Arnie’s work was on!
We wish you all the best. You have so much talent and we know you love being “boss”.
Arnie is my inspiration! I was only freelance two years when we met, he was so encouraging!
Thank you Caroline
That was LAMP shades.
Brillant reflection on the freelance life. The parachute mid-air analogy captures someting most career advice misses - that uncertainty isnt a phase to endure but the actual terrain of creative work. What's inetersting is how the identity shift happens gradually, from 'freelancer struggling without structure' to 'professional who's internalized their own systems.'
All I have to say is that you look darn good for your age. I also wanted to share the reason I have a paid subscription to you all. I looked at the news I receive on Substack and I needed some humor to go with the sadness of the news I read. I thank you for lightening up my spirit. 'Berta
Thank you so much Berta! I really appreciate it
Great piece, as usual, Jason. Somehow you manage to make it seem pleasant. From my experience, it is! I've been freelancing since 1978 (not a typo), and one recurring question from W2 recipients: "How do you cope with the uncertainty of not having a regular paycheck?". My answer was that I manage money a lot better when I didn't know exactly when I was going to get any. Keep up the great work, my friend.
I appreciate the kind words. Thanks Michael!
Congrats, mate!
Good on you! You're a gem.
Thanks so much, Andi!
A self starter * highly motivated* even as a youth .
The love you have for your craft is evident .
Keep up the terrific work as much appreciated .
LM
Thank you, Louise! 🙏
Happy 21st to your career!
Beautifully said - my 60th year and still building that parachute - so glad I did it and still am. Clearly you have all the right tools to keep building. Cheers!
This is an amazing description of what it must be like to be a freelancer. As a high school art teacher for the past two decades I don’t know what that life would feel like but at least now I can share your description with students who might think about being a freelancer with their art skills. Thanks Jason!
I can remember my late bf, James (he passed in 2016) telling me how just after had the money to buy his house- the TV show he was on got cancelled. And when I finally moved into my home in my late 20's, I lost my job on a TV show... and I panicked, not certain how I'd pay my mortgage or anything. I was pretty young to have gotten where I did by 28 in the world of TV production... and then all of a sudden I was just shot into the world of freelancing. And that concept of building the parachute as you freefall is so relatable to me. I changed my career path completely in my 30s, sold my home and started waitressing. And I soon got into comedy and started on my path of documentary filmmaking... and all of this is to say, I've found a way to dance as I free-fall. I like how my life is a bit here and a bit there. I'm creating all the time. It's a way I couldn't imagine not living... and to think when I started on this path, I didn't know how I'd live. Growth, baby! Growth. :)
Love this perspective. That parachute metaphor captures the freelance grind perfectly, especially the part about trying to sew it mid-fall. The identity piece is underappreciated too, when theboss and the employee are the same person perpetually negotiating with themselves about deadlines and vacation.