First podcast of yours I listened to (not a big consumer of podcasts), and thoroughly enjoyed. When I was 14 for my "career" paper in high school, I interviewed 3 writers and all 3 said---get a different career, make the writing your side hustle, because you will never make a living at it. Probably why I became an historian rather than taking literature or creative writing as a major in college. Then made my writing my "hobby" throughout my teaching career by writing and rewriting what would become the first book in my historical mystery series. Then in retirement...well.. here your 3 bucket analogy breaks down a bit, because I started, as a self-published novel writer, to I make enough to live on, if I needed to) but in reality it was more of a side hustle to my retirement income, in that I didn't have to live on what I made. But I definitely did and still do write primarily for joy-felt by me, and apparently if my sales and reviews can be believed, for fans of my books. I also have adopted the "patronage" model on substack--by not putting anything behind a paywall--but that is because it was never intended to make money, but only to keep up a dialog with my already existing readers (and provide a way they can "tip" me if they wish. Otherwise, my expectation is simply that they go out and buy my books as I publish them. :)
Somehow I've managed to make creative writing my full-time career. A lot of big feelings followed, mostly from my extremely flabbergasted and disappointed wife.
Right before I graduated with a B.A. double major in Radio & Television Production (maybe one $100 per week job for every graduate) and Computer Science (ten $18,000 per year jobs for every graduate), I rightly decided to job search in software. On my first set of interviews, it took me most of the day to realize I was interviewing with a bunch of hardware programmers that all worked on the same project. The next day I interviewed with a bunch of math nerds that were interested in fast Fourier transformations (yeah, 40 years later I still don’t know what that is). The same day the math nerds sent a rejection letter, the other guys sent a job offer. Since the job was in the same city as my girlfriend’s job, I took it.
I ended up working for a genius for 18 years across 3 companies. After the 3rd company laid me off, I went to a company for 11 years and had 13 bosses. 8 of them were fired the day they stopped being my boss. But that was preparation for the next job where I had 3 bosses at once for another 11 years. Now I’m mostly retired except that I do special assignments for those 3 bosses for about 30 hours a month.
So overall, it’s been fun. And I still haven’t decided what I’ll do next year when I have to start taking Social Security.
Really liked this podcast, especially the delineation between career, hustle, and hobby.
I started writing some comedy pieces last year and I’ve been trying to figure out where it all fits in, what direction I want to head in, etc. so this was very helpful in getting my head some clarity. Thank you for sharing! Still need to go check out the other post you mentioned during the episode.
Funny, and profound. My career is providing a service that people “need”, yet regularly people ask if they can pay some other time (translated as never) because they need to pay for the spray tan and manicure they are going to right after their time with me. Thus, the questions of what do people need, what do they want, what is their priority to pay to obtain.
Enjoying your podcast, and your thoughts on these “buckets” - I had a similar epiphany of sorts back when I was first out of college and working hard to make theatre my full-time job - I succeeded for a time, but whenever I went over to the community theatre side of things - where the “hobbyists” were playing - it looked like so much more fun than I was having. The ones doing art for the love and not the money reminded me why I wanted to be in the arts in the first place.
I enjoyed hearing your perspective on humor writing, and where it fits in the Substack universe. Rule of Three’s take on The Substack experience, which includes a shoutout to Situation Normal. . .
Great episode, Michael. I really enjoyed hearing about your first job and then how you dovetailed into present-day, Substack-specific dynamics around being paid for writing.
This episode has me thinking about the nature of my own work (writing and offering writing guidance as an editor) and how my newsletter can "succeed" when I also don't enjoy being slimy with guarantees, gimmicks, 10 tips for fast growth posts, etc. If I use your very helpful framework (thank you for that, btw), I think right now I have a side hustle that's funded like a hobby, but we'll see where 2024 takes us. 😉
CAFÉ ANNE is a side hustle but plan is that it pays the rent by 2026!
Loved this episode Mr. Estrin!
First podcast of yours I listened to (not a big consumer of podcasts), and thoroughly enjoyed. When I was 14 for my "career" paper in high school, I interviewed 3 writers and all 3 said---get a different career, make the writing your side hustle, because you will never make a living at it. Probably why I became an historian rather than taking literature or creative writing as a major in college. Then made my writing my "hobby" throughout my teaching career by writing and rewriting what would become the first book in my historical mystery series. Then in retirement...well.. here your 3 bucket analogy breaks down a bit, because I started, as a self-published novel writer, to I make enough to live on, if I needed to) but in reality it was more of a side hustle to my retirement income, in that I didn't have to live on what I made. But I definitely did and still do write primarily for joy-felt by me, and apparently if my sales and reviews can be believed, for fans of my books. I also have adopted the "patronage" model on substack--by not putting anything behind a paywall--but that is because it was never intended to make money, but only to keep up a dialog with my already existing readers (and provide a way they can "tip" me if they wish. Otherwise, my expectation is simply that they go out and buy my books as I publish them. :)
Somehow I've managed to make creative writing my full-time career. A lot of big feelings followed, mostly from my extremely flabbergasted and disappointed wife.
I’ll take #3.
Right before I graduated with a B.A. double major in Radio & Television Production (maybe one $100 per week job for every graduate) and Computer Science (ten $18,000 per year jobs for every graduate), I rightly decided to job search in software. On my first set of interviews, it took me most of the day to realize I was interviewing with a bunch of hardware programmers that all worked on the same project. The next day I interviewed with a bunch of math nerds that were interested in fast Fourier transformations (yeah, 40 years later I still don’t know what that is). The same day the math nerds sent a rejection letter, the other guys sent a job offer. Since the job was in the same city as my girlfriend’s job, I took it.
I ended up working for a genius for 18 years across 3 companies. After the 3rd company laid me off, I went to a company for 11 years and had 13 bosses. 8 of them were fired the day they stopped being my boss. But that was preparation for the next job where I had 3 bosses at once for another 11 years. Now I’m mostly retired except that I do special assignments for those 3 bosses for about 30 hours a month.
So overall, it’s been fun. And I still haven’t decided what I’ll do next year when I have to start taking Social Security.
I think creative writing is destined to be a small side-hustle for me, but I really enjoy it, so that's all right.
I wish more lawyers would pay comedy writers to come up with book ideas.
Really liked this podcast, especially the delineation between career, hustle, and hobby.
I started writing some comedy pieces last year and I’ve been trying to figure out where it all fits in, what direction I want to head in, etc. so this was very helpful in getting my head some clarity. Thank you for sharing! Still need to go check out the other post you mentioned during the episode.
Funny, and profound. My career is providing a service that people “need”, yet regularly people ask if they can pay some other time (translated as never) because they need to pay for the spray tan and manicure they are going to right after their time with me. Thus, the questions of what do people need, what do they want, what is their priority to pay to obtain.
Enjoying your podcast, and your thoughts on these “buckets” - I had a similar epiphany of sorts back when I was first out of college and working hard to make theatre my full-time job - I succeeded for a time, but whenever I went over to the community theatre side of things - where the “hobbyists” were playing - it looked like so much more fun than I was having. The ones doing art for the love and not the money reminded me why I wanted to be in the arts in the first place.
I enjoyed hearing your perspective on humor writing, and where it fits in the Substack universe. Rule of Three’s take on The Substack experience, which includes a shoutout to Situation Normal. . .
https://ruleofthree.substack.com/p/me-and-kareem-and-glenn-and-heather
Great episode, Michael. I really enjoyed hearing about your first job and then how you dovetailed into present-day, Substack-specific dynamics around being paid for writing.
This episode has me thinking about the nature of my own work (writing and offering writing guidance as an editor) and how my newsletter can "succeed" when I also don't enjoy being slimy with guarantees, gimmicks, 10 tips for fast growth posts, etc. If I use your very helpful framework (thank you for that, btw), I think right now I have a side hustle that's funded like a hobby, but we'll see where 2024 takes us. 😉
Did you know that Geraldo Rivera graduated Brooklyn Law?
And can it be my side hustle and my career? One of the great benefits of being over 65?