How to turn disappointment and despair into success with playwright Jack Canfora

In this episode of The Mindful Writer, Jack Canfora and I explore the challenges of keeping a calm and positive mind despite disappointment and despair.

Welcome back to season two of The Mindful Writer. There are lots of great guests in this season. As always, they have been a joy to meet and I am looking forward to sharing their wisdom with you.  

In this episode, Jack Canfora and I explore the challenges of keeping a calm and positive mind despite disappointment and despair.

Before I introduce you, let me update you on my writing journey. Life has become incredibly busy for me – but exciting too. We returned from a Mediterranean cruise a week ago, our first venture abroad since the pandemic. It was a wonderful holiday and I returned with my creative well overflowing from the many fascinating experiences on our travels. 

The downside of a holiday is managing the workload before and after the break. I am following the advice I have shared here from guests – scheduling everything in my diary and only concerning myself with one day’s activity at a time. 

Alongside preparing for the launch of my next novel The Forever Cruise on 1st December, which is incredibly exciting because it will be my first in person launch event since the pandemic, I am helping to organise the Frinton Literary Festival in October. Paula Hawkins and Freya North are just two of the authors featured this year. 

I try to schedule at least two hours every day to write, as well as allocating marketing and admin time. It would be easy to neglect my writing if I did not make this a priority.

When there are many competing demands on our time and we feel overwhelmed by the to do list we often neglect our self-care. The truth is relaxation, exercise, family time – the things that make us feel good, are even more important because when we balance these with work we achieve more and become more resilient. 

My guest this week has experienced many highs and lows in his writing life and has a realistic perspective on what we might expect of ourselves in challenging times. So, let me introduce you.

Jack Canfora is a playwriter and podcaster. He blogs www.thewritingonthepaddedwall.com, has an

online theater company  www.newnormalrep.org with a podcast “New Normal Rep’s Play Date” on most platforms.

In this episode we explore:

What we can and can’t control as writers and when to let go

Coping with envy and disappointment

How we can learn from our suffering, turning it into something positive

Jack Canfora

You can listen to the podcast here: Season Two, episode One.

 How to turn disappointment and despair into success with playwright, Jack Canfora.

Or read the transcript below.

Deborah: Jack Canfora, playwriter, podcaster and writing coach, I came across you through the Pointless Overthinking blog as you’re a regular contributor. However, since then, I’ve discovered and listened to your podcast NNR, the New Normal Rep Theatre Company podcast, and I love your energy and sense of humour. There have been numerous regional productions of your plays, and you’ve won several playwright awards. So, I consider you to be very successful as a writer. This is something you and I have discussed – how do we measure success? So, Jack Canfora, what does success look like to you?

Jack: Well, I can tell you what I aspire that answer to be for me, which is – and I’m getting better at it, I feel I’m getting closer to it – is thinking of success in terms of doing what you’re doing, in my case writing, as well as you can possibly do it. In whatever that means to you, you know, for me, it is to be honest, and it’s hopefully entertaining, but also accomplishing what I set out to do, which is writing a play – simply writing a good play. And if you get people to perform it, that’s even better, of course. But ultimately, those are all things beyond your control – beyond my control, certainly, and the only thing I can control is how well I write. And if I feel satisfied with what I’ve written – relatively, because I’m never completely satisfied, right?  I think someone said, forget who – they said about plays, the plays are never finished, they’re just abandoned. And I think that’s true of probably all writing. But as long as I can feel at the end of the day, I’ve done the best I could do, then that should be my definition of success. And there are days where I’m pretty close to that. And there are days also when I get to work with some talented people, which I’ve been very lucky to do pretty regularly, and get to spend time in a room with them working on a play that I wrote, and they take the trouble to remember the lines I wrote.  I mean, that’s pretty great in and of itself. There’s a sense in which, you know, what more could you want from from life? In fact, that’s the most fun for me – being in the rehearsal room and doing those things in collaboration. There are external things sure, like, having your name better known and having some money. I wouldn’t lie and say that I’m not so profound, that those things don’t matter to me. But I think in the end, I have to try to measure and I think all I can do is try to measure what I can do, and leave the other things to the fates. So, is that too long a winded answer?

Deborah: No, it’s not at all, but there are a few things I want to pick up with you on the interesting points you made. First of all, the point you made about the things we can and the things we can’t control, that’s quite difficult, isn’t it?  To think about what we can control and letting go of the things we can’t.  I know you coach writers, how do you help them cope with the letting go of what they can’t control?

Jack: Well, first of all, do as I say not as I do to a certain extent. I mean, I think it’s something that’s aspirational. Like I would argue, mindfulness is probably. You know, attaining that perfect sort of Zen – just being in the moment and letting everything go. Very few people can ever really, truly accomplish that for any length of time. But that’s always the goal. And you can’t – paradoxically, you can’t measure your time there in terms of goals. It’s just, you know, being in the moment in terms of letting go of the stuff you can’t control. I think it’s a tough reality to square with what your dreams or ambitions may be. I have to tell myself this on a regular basis. I read – someone posted something recently, and they said that ‘the theatre is at least twice as old as the Christ’s tale and it’s been disappointing disciples ever since and that – art owes you nothing. And you owe yourself the best you can do. The things that are beyond your control – you’re going to have to let go one way or another, are you going to let go of it freely? Or even let go of it? Or are you gonna have it prised from you kicking and screaming? Either way, you’re gonna have to let it go.

Deborah: We’ve all had that experience – that kicking and screaming, when you rail against the world that ‘why hasn’t this or that happened?’ and, ‘it’s not fair.’ The energy we waste on that.

Jack: Oh, my goodness, yes, that’s, you know, more of my week than I would like to admit.

Deborah: Another point you said, is knowing when to let go – when it’s finished. Saying that, you can keep on and on and on, and you say ‘a play is just a play that’s been abandoned because it’s never finished.’ There are two things there: How do you decide it’s good enough? And also, when you’re doing the best, you can, for yourself – to show your best work, how do you stop those voices in your head, that are the critics – the voices questioning how it’s going to be received that get in the way?

Jack: Yeah, well, again, it’s sounds like this is going to be a wishy-washy answer. But I think that it’s a little bit of both. I think you do have to silence those critics at a certain point. But I also think it’s important to listen to them to a degree. Because, I think, if you don’t, you run the risk of becoming sort of self-indulgent. And the minute I think, as a writer, and as a novelist, or a poet, or short story writer, or a playwright, or what have you, you send – you know, you write your work and keep it to yourself, that’s fine, you can be as self-indulgent as you like, it’s sort of freeing in a way – but the minute you send it out for someone else to read, then I think you have an obligation to not be that way, to yourself as much as anyone else, because probably no one’s going to want to read it or do it if it’s that way.

 I have been lucky enough to cultivate relationships with a few people in particular, whom I have great respect for. And so, just to give you my own experience as a playwright, if I’m in a room with people whom I trust, you know, in terms of their intellectual and emotional judgement about a work, and they say, X, and I was thinking Y, then, that doesn’t mean I’m wrong necessarily. Or there is a wrong. But if you’re saying X, and my intent was Y, it behoves me to at least consider X, because three very smart and dedicated people have said this whom I trust. And again, I can’t emphasise that enough, because there are people who, whose judgments won’t jive with yours. And so, you need you need to be open to that critic. 

But on the other hand, you also have to say, you sort of have to feel I think, when you’ve reached a wall. The great thing for me as a playwright is if my play is being produced, there reaches a point where the script is what they call frozen, and the actors and you are no longer allowed to make changes. And that is a great thing to do, you know, to a writer actually, because you can overwrite things. I think, a lot of problems for playwrights and also my guess is for novelists or other fiction writers, you can workshop things to death. And there is a point where, you know, there’s little quirks in the play that technically may not be by the book correct. If you sand all those away, it becomes pretty nondescript. So again, it’s a question of taste, right? I mean, I readily accept that not everyone is going to like my plays. I say that, but I don’t really think that!  But I aspire to that. I mean, Tolstoy hated Shakespeare, so Shakespeare can’t be beloved. I do feel the onus of having everyone like me, is definitely lifted off of my shoulders. You know, I just have to do the best I can. And you know, again, it’s a constant practice. I think it’s a practice and I’ve never gotten there completely. I may never achieve that at all. But that’s certainly what I what I aspire to do. 

What I would advise is constantly tug back and forth with yourself. Be absolutely as forgiving to yourself as you can be while you’re writing and then as ruthless with yourself as you can be when you’re editing. It’s a bit of a back and and forth, I think.

Image by Hoàng Anh Vũ from Pixabay

Deborah: Do you use anything like yoga or meditation? Because as you were talking, and you were saying, keep going back to it, it made me think of when we’re meditating. And your mind wanders, and you come back to the stillness. So, do you have affirmations or meditation or anything to help keep you in the right state of mind? 

Jack: Yeah, I think I would benefit enormously from it. And again, I think my story is very typical. But I have tried meditation on several occasions and have found it bafflingly hard. And I am ashamed to say I have, you know, I’ve sort of walked away from it. But, you know, it’s, it’s clearly to my benefit to try it again. I guess this is the word of the day, I aspire to get to that place where I can incorporate that as part of my life, because I have no doubt that it would help every aspect of my life.

Deborah: I’m a great believer in in meditation and yoga. It’s part of my daily practice. And it has made a huge, huge difference. In fact, I started a daily meditation practice, when I knew I was going to be going through a challenging time as a writer. This is about four years ago, when a book was out with an agent, to find a home for it – a publishing contract.  I started doing it then – planning to do it in the 40 days for Lent before Easter. And I’ve carried on, I think about four years into it now, for daily practice. 

Jack: That’s wonderful.

Deborah: When I compare how I was, emotionally, and mentally, at that point – when I was waiting for to hear back about my work, compared to how I am now. All the things you say about letting go and being calm and accepting. I’m totally – I can feel, in that place. And I just noticed such a huge difference.

Jack: Yeah. I guess I would want to drill down on that a little bit. So, like you said, that you’re in a completely different place? And is it that you just feel calmer and more at ease? Or is it something more profound than that?

Deborah: I wouldn’t say – profound, in terms of great spiritual-awakening-type things, to dress it up. It is a sense of absolute calmness. But the greatest thing for me is really being open to possibilities. And knowing that I’m not giving responsibility for my happiness into an agent’s hands or in the outcome. I’m not wedding myself to one particular outcome. I absolutely feel uplifted by the number of potential outcomes there might be. And I truly, truly believe 100% that the right thing will find me at the right time. And I have absolute faith in that. It takes an awful lot away from the anxiety. And I think that positive attitude, and that feeling of well-being, you’re more likely to attract something, just by the fact that if somebody is positive and happy, and not chasing something, they’re more attractive to a person, whether it’s dating or a job or anything. The desperate person, the uptight person has a closed mind and can’t see the wood for the trees. So, I think it’s just practical, you know?

Jack: Well, I think that’s a much better answer than I gave about what you would tell the student in terms of letting go. Yes, absolutely, that sounds wonderful. I hope to get there someday. But yes, I mean, I think that’s exactly it. It’s not living and dying with every rejection. Because if you do that, you’re I mean, as a writer, as an artist, you’re just really asking for it. I mean, I think you’re asking for it as an artist to begin with, right? You know, the odds are stacked against you, in terms of what you can control in terms of, you know, the standardised in normative sense of what success, you know, means. So, if you go chasing after that, and if you go chasing after that doggedly, with only one sense of what constitutes happiness or success, or, you know, and I think, you know, as a writer, and just as a person, if you do that, then you’re bound to be, you know, the irony is, I think the more you do that, the less likely you are to, to get that specific thing, because you’re never going to. It’s never going to be played out the way you expect it to play out – good, and bad or indifferent. You just have to sort of be flexible enough to bend with the wind.

Deborah: So, looking at your journey Jack because often when you look back, you can see oh, that happened. If that hadn’t happened, this wouldn’t have happened. And it all starts to make sense. What has your journey been like? Because as I said, you are successful, and it can’t have always been easy. So, what were the breakthroughs for you that you can look back on and say, ‘Oh, well, I’m glad it happened that way?’

Jack: Again, success is such a relative thing. I mean, you know, it’s there. I’ve been very lucky in many regards, with plays done regionally in and off Broadway, and I’ve a couple, you know, published for sale on Amazon, by the way. 

Deborah: Which I will promote in the show notes (see below).

Poetic Licence and Jericho

Jack: But, I think inevitably, the answer comes down to relationships for me. You know, I’ve been able to meet people and some people fall away, just like you fall away from certain people’s lives. But I’ve been very lucky in cultivating some really good relationships with people who have helped me both pragmatically, but also just grow as a person and as a writer. So really cultivate those relationships, and not let in a cynical’ What can I get out of this person?’ way, but in a genuine form of connection. 

I have had it pointed out to me by a few people who have seen my plays, that a common thread is running through them, because the subject matters differ pretty wildly. But a common thread is – people sort of seeking a community or connection. And I think that’s probably true. It’s never in my mind as I’m writing it. But I think it’s probably true. And I think, especially these days, I think, you know, our culture is sort of, you know, finely crafted to promote alienation. And so, I think that it’s something we all need. And I remember, as a kid, I found that with people doing theatre, or as a musician, when I was in the band, you know, a lifetime ago. But, yeah, it’s always about the people to me, and I think I would, I would give myself this much credit that even a while ago, even at a fairly young age, even if I didn’t know it, intellectually, I intuited that really, the point of things is relationships, and other people. Not that you should become dependent on other people, but that you should be welcoming of other people. And so, yeah, like I said, I think that’s the one key thing for me that I’ve realised over and over again, that inevitably boils down to the relationships you have with people.

Deborah: Excellent advice. I agree. Absolutely, networking is so important, you don’t know who might come into your life that can have a huge influence, and how you can help other people. 

Jack: Yes, has to be reciprocal. I completely agree, and you have to be fine with it, you know, doing something with someone when they have some sort of pragmatic success from it, and you don’t necessarily. That’s certainly happened to me. And you have to sort of let go of that little childish self that says, ‘Well, why didn’t I get some?’ Which very much exists within me, but yeah, I am much happier, when I can be happy for that person. You know, and it’s just a very nice feeling.

Deborah: That’s a really good thing to pick up. Because I think we would be lying if any of us said we didn’t, at some time feel envy for a fellow writer who we wished well, who we loved with all our hearts, but we thought, That’s not fair. And then, you feel awful that you think that’s not fair when you really do wish them well. Feeling why not me? And it’s, as you say, it’s a childlike emotion, because that’s where we are.

Jack: Yeah, that’s where I am certainly. I think it was Gore Vidal said, ‘Every time a friend of mine succeeds, I die a little inside’, which is a little too acidic, I think, for it to be, you know, entirely true. But yeah, we all have those feelings. And I think it’s okay. You know, as I’ve grown up or attempted to, I think, one of the things you learn is that your feelings are going to show up, and they’re going to take whatever form they take. It’s a question of, you know, you can’t judge yourself for that, because there’s a sense of what you’re not, you’re not in control of your feelings. What you can control is what you do with those feelings and what feelings you choose to dwell on and to focus and to foster. That’s your choice. But the feelings themselves aren’t either good or bad. They just exist.

Deborah: When I do my meditation, if I feel like that, I do two things. One, I acknowledge, that’s how I feel and I don’t give myself a hard time about it. I just feel where it is in my body. I can feel it and recognise it’s there. And then I think about that person, wishing them love, wishing them the best and sending light and love. It sounds a bit hippy, but it’s sending a sense of feeling to them that I genuinely want well for them, and then with those two combined, and trusting that there’s a different path for me – and that’s okay. Those two techniques really helped me.

Jack: Yeah. I think that wonderful and it’s down to you, if you can put out that feeling genuinely – out there to the world. To quote someone else – the Beatles said, and  I think it’s very true, ‘The love you take is equal to the love you make.’ And I think really the point of that is – you need to learn to give and feel good and feel love wherever you can find it. And just, again, let go of anything negative and don’t judge yourself for it. You know, everything is transient. Even your darkest feelings are going to pass. Don’t try to label them. And more importantly, don’t label yourself based on what you’re feeling at any given moment.

Deborah: I was listening to something on TV about Julie Andrews’s life, you know, Mary Poppins, My Fair lady? 

Jack: Oh yeah!

Deborah: Well, this is a great true story. I hadn’t really realised at the time but Mary Poppins, not Mary Poppins, sorry, Julie Andrews – she’s just a real person! Julie Andrews had done My Fair Lady on Broadway and in London. And it was huge, huge success. So, when they were coming to choose an actress to be in the film, she assumed it would be her. And of course, it wasn’t.  It was Audrey Hepburn. And can you imagine her disappointment, you know, as an artist, when that happened? How devastated she must have felt? She really believed it was hers. And it wasn’t. And then a few months later, the role of Mary Poppins fell into her lap. And she was asked to do that. Then when it came to the awards, that film and her as leading actress, got more awards than my fair lady. I take from that, when things don’t go the way that you hope they will or expect them to, very often, there’s something much better that you hadn’t envisaged just waiting for you.

Jack: That’s absolutely true. And that’s true of my life as well. In low moments, it’s very hard to see that maybe this is a new opportunity, in that this clears the path for you to go a way and you’ll actually get more out of. I’ve had multiple experiences of that my life. 

Deborah: Yes, me too. And I think the older you get – I’m sure I’m older than you.

Jack: You’re more mature than I am, I’m sure.

Image by Wolfgang Eckert from Pixabay

Deborah: As you go through life, the more experiences that you have that you can look back on. You can use those as a reference point to think, ‘Ah, but when that didn’t happen, X happened. And when that didn’t happen, that happened.’ And you get more and more affirmations that this is the way life can work – is, working for you. And that fills you, I think, with positivity. If you can go back and remember that.

Jack: Yes, absolutely. It’s so hard for me to claim to be committed. It’s so hard for me in the moment, where I’m expressing or experiencing disappointment to, to remind myself of that, but it is vital to do that. You’re absolutely right.

Deborah: It’s a journey. We’re all a work in progress.

Jack: Yes. Very much so very much. 

Deborah: That’s why the journey is so interesting.

Jack: Yes, that’s right. I won’t pretend this is an insight of mine, it’s pretty much common knowledge. But, you know, suffering is awful, it’s why they call it suffering, but it’s also imperative that you have it without that you wouldn’t grow in any way. I suffer a lot from depression, and I don’t recommend it to anyone, if they have a choice. But having said that, I also have to, in my less desperate moments, realise that it’s actually been a pretty, a very strict and mean, but very good teacher. At times, I think I’m a lot more empathetic than I would have been, had I not had those feelings. I think, whatever abilities I have, to whatever degree I have them, have been sort of sharpened I think, by that experience. I mean, certainly, I don’t think I would have been a writer. And I certainly wouldn’t have been, you know, as however good or bad or I may be, I wouldn’t have been able to reach the potential I’ve reached, you know, to whatever degree that may be without that suffering. And so, I think it’s you have to accept, you know, the yin and the yang as they say.

Deborah: It’s a really good point to make. Thank you. How would you like to be remembered?

Jack: Well, if I’m remembered at all that would be a little surprising for me. I think ultimately, you know, I mean, cliched answers are really cliches for a reason. I really want to be – I have two children who mean the universe to me. And so, I want to be remembered by them, as someone who loved them and did his best even when he – you know, although I am far from perfect father, but that they knew that they were loved and that I love them. And then, beyond that, I would love to be thought of fondly by my friends and most of the people whose lives I’ve been in, that won’t be 100%. But it’ll hopefully it’ll be nice. And then maybe if in my small, totally unverifiable via data way made the world just made, like a half a centimetre nicer, you know, slightly, slightly better than when I showed up. 

Deborah: I’m sure you’ve already done that, because my favourite film is, It’s a Wonderful Life.

Jack: Oh, that’s a beautiful one. The day, I don’t cry at the end of that movie is the day I really need to worry about myself.

Deborah: So, I’m sure you already touched a lot of lives through your plays and your work.

Jack: Well, that’s very kind. Thank you. Then of course, lastly, I would love it if a play or two of mine survived into the next generation, but ultimately, I won’t be around. So, the most important thing is to just, you know, be as kind as you can be, as often as you can be. There are days in which the bar for my ability to be kind is pretty low. So that varies, obviously, but I think that’s our main job – to try to be kind. When I was younger, I really valued talent and intelligence. And it’s not that I don’t value those anymore, but I place a lot more stock in than just being a good person, you know, a nice person, which sounds idiotic, but I think it’s true. I mean, I think being proud of, you know, your intellect, for example, is like being proud of your blood type it is sort of an accident of birth. But kindness is something you have to work at. 

Getting back to our earlier point about what do you have control of, you don’t have control over a lot of things. And you don’t really have control over your talent to a degree. I mean, you can work at it and shape it, and I think you should, but you don’t have control to a degree in your intelligence, for example. But you do have control in how kind you are, and how you treat other people. So ultimately, I think that’s what I respect that, more than anything.

Deborah: Again, this is probably a cliche, but when I heard it, which wasn’t that long ago, for the first time, it had an impact on me. I was at a funeral. And the celebrant said, ‘It’s not what we have achieved, but what we have become that’s important in life.’ And I thought that was so true.

Jack: Yes, that’s really wonderful. It’s far better than I would have come up with, but I think it’s so true. And I think that, you know, in life as I get older, I think that most of life is a verb as opposed to a noun. You know, it’s about acting, whatever way you want to, but acting in the best way you know how for yourself and for others, rather than just thinking things will come to you or thinking things are facts – unalterable and permanent. You know, it’s about, it’s about trying to do these things that matters more.

Deborah: I nearly said, ‘absolutely.’ And I’ve noticed when I’ve been editing my show notes, I say absolutely too much. Absolutely.

Jack: Well, good. Good. I got a couple of them out of you so I succeeded today.

Deborah: Great. So finally, what words of wisdom would you impart to your younger self, when you go back to when you first started out writing and you felt overwhelmed by what you wanted to achieve and where you were? Looking back, what would you say to yourself?

Jack: Well, I would say to myself, and I think is what I would say to myself today, and will say to myself tomorrow, which is much of what we’ve been talking about is – ‘Just do the best you can do and don’t worry so much about the other things.’ 

Everyone would always like to have accomplished more materially. I certainly would, I’m not ashamed of saying that, but and I haven’t accomplished nearly as much as some and I’ve been fortunate enough to accomplish in the material sense, more than other people. Although, again, at the same time, you also have to realise a lot of it doesn’t have to do with you, a lot of it has to do with luck, and it’s not really necessarily in any way a definitive quantification of your abilities. 

You just have to do what you can do and try and enjoy the relationships and just enjoy the work as much as you possibly can, even when – this is gonna sound ridiculous, but even when it’s not fun. You should still enjoy it as much as possible. And, again, do everything you can to succeed materially, but don’t use that as the arbiter of whether or not you’ve succeeded or failed.

Deborah: Those are great words of wisdom. Life goes by far too quickly for us to waste our energy being unhappy. 

Jack: Yes, absolutely. Now I’m saying it now. You’ve started a trend.

Deborah: Brilliant.

Jack: It’s your catch phrase.

Deborah: (laughs) I’ve really enjoyed talking to you Jack Canfora.

Jack: Likewise. Thank you so much for having me on.

Deborah: It’s a pleasure. So, I will give links to your work in the show notes. 

Jack: Please do. Thank you so much. And again, it was such a pleasure talking to you. A lot of fun. Thank you. 

I really appreciate Jack’s honesty in talking to me about disappointment, envy, and suffering because we all experience these feelings at some time, even the most successful of writers. It is what we do with them that makes us stronger and better – both as a person and a creative.

Since chatting with Jack he has told me about an audio play that is going to be released on all podcast platforms in October, called Step Nine. You can find out more by visiting his theatre company’s website www.newnormalrep.org. I recommend you subscribe to New Normal Rep’s YouTube page, which has lots of amazing free content, including an online production of Jack’s last play Jericho, directed by Marsha Mason. 

I will be away on a writer’s retreat before we next meet. I’m so looking forward to spending a few days hidden away in the wilds of Norfolk with my writer friends, where I intend to lose myself in my WIP. When life gets this busy I have to remind myself that I love everything that I do and try to enjoy each moment instead of fretting over getting everything done!

Please check out The Forever Cruise available for pre-order on Amazon for just 99p/99c until publication day on 1st December. 

So, until we meet again look after your beautiful self, and trust the journey.

You can find all episodes of The Mindful Writer podcast here: https://themindfulwriter.buzzsprout.com

Don’t forget to subscribe so you don’t miss any episodes.

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