Episode 32 - Seasons


Jen: Hey, Peter.

Peter: Hey, Jen.

Jen: I sounded so American just then: "Hey, Peterrr."

Peter: G'day, Jen.


Jen: Oh my God. I heard someone, a friend of mine who is a coach, say something last week that really struck me, and I would like to talk about it. And what she brought up with me was what she called, quote, "the season of overwhelm." End quote.

Peter: End quote. The season of overwhelm. I'm curious.

Jen: So what I want to talk about is not necessarily "overwhelm," but seasons.

Peter: Okay. It's currently approaching Winter, and you're approaching Summer. So, seasons sound like a very topical and fun and relevant discussion. This is The Long and The Short Of It.

I don't know why I needed to add context about seasons, but we went there.

Jen: Hey, it's all good. Well, it's funny, because right before we started recording, you were like, what's on your mind? What's going on? I was like, "Summer's coming, Summer is coming. I can't wait!" And the reason I can't wait is because that is a specific season for me. I'm not talking about the weather - although, I am talking about the weather - but what I'm talking about is the quality of life that I live during the Summer, and the quality of work that I'm able to produce during the Summer, versus what I just came through, which was for me, my season of overwhelm - January, February, March and early April in the theatre industry is absolute chaos. It is a season of overwhelm. And I wanted to, sort of, hear from you, and share from my perspective why it might be useful to think about our lives as having seasons. And just as you do spring cleaning for the Spring, and you, you know, get your Winter coat dry-cleaned before it snows, how can we be better at preparing ourselves for the seasons that we know are coming?

Peter: I love this idea, particularly because this will be, I think, an important learning experience for me, because I, full disclosure, do not think about, have not stopped, paused to think about how my work, how my life is structured into seasons, other than the Summer, Autumn, Winter, Spring weather. But honestly, from a work point of view, I've not done this, but I really like the of what that might help me see. So this could be, this could be a live "Aha!" moment in the making.

Jen: Oh, that's so, so exciting! Okay, well, I will do a little sharing from my perspective, and then I would love for you to bounce your ideas back, and maybe self-reflect and self-assess and do it in real time.

Peter: Alright. Talk to me, what are the Jen Waldman seasons?

Jen: So, I've got the season of overwhelm, which is January through mid-April. And I believe the overwhelming majority of the clients that I work with also experience that same season of overwhelm, which is why I think it is ironic that so many of my clients set New Year's resolutions and believe that they're going to be able to instil and implement new habits at the busiest time of the year where everything is, like, a complete and utter chaotic mess. So, after the season of overwhelm, I have this sort of, like, "bridge-the-gap" moment, which I'm in right now, which is like, a time to tie up those loose ends, figure out anything that I need to, sort of, deal with before I enter my "season of creativity and productivity and inspiration," which is really, for me, from the American holidays of Memorial Day to Labor Day, when my daughter's school year is coming to a close. I don't teach any of my group classes during the Summer. I do this program for a very limited number of artists in the Summer months, and I basically take back all of my time and completely change my routine. That is the season where I feel like I am doing my best, most creative work, and because I'm working on a book right now, I think I'm chomping at the bit to get there, because I feel so confident that I'm going to exit that season with a working draft.

Peter: And what - I love this - what dates are the, what date is that for the rest of the world and the ignorant Australian sitting over here?

Jen: Oh, so that is the last Monday in May Through the first Monday in September.

Peter: Ah, okay. Nice. So, essentially the Winter in the southern hemisphere.

Jen: Yes. So essentially, Summer. And then once we exit Summer, my daughter goes back to school and I get back to the studio and it is a, it remains a productive time but is much more structured and much more reliant on time management to get things done and also leave room for time with my family and, and creative projects. And then once we get through this, the holiday season, at the end of the year, I go back into the season of overwhelm, and it's like, I put my head down and I do not come up for air until the middle of April. It's just crazy. Even though my daughter has a two week break during March that we tend to go away for those two weeks. But even during that time, it's like so many people have so many moving pieces and things are very, very urgent. So I'm always in work-mode even when I'm not working during that time.

Peter: And then the overwhelm comes again. It's so, it's so interesting to me. I mean, obviously, your Summer/my Winter sounds amazing. This idea of creating space to be creative, this idea of spending time with your family, the weather's warmer, all that, unbelievable. Like, I love that you construct your life in a way that you can really appreciate that time. What I'm curious about is, all of this, but in particular knowing that the season of overwhelm exists, how might you mitigate it so that it's not the season of overwhelm? Or, do you think about creating a structure or a way of approaching your work so that it's not an overwhelming three months, four months? Or is it that that's just part and parcel of what it means to be Jen Waldman?

Jen: I should say that I don't necessarily feel particularly overwhelmed. It's just very, very busy and there are a lot of moving parts. So this year I tried something different, which I think was very successful, which was, I created a new course that I ran for four months, four different groups, around shifting your mindset and changing the way you're moving through your life. So I, I introduced this right before the new year because I knew we were about to go into this season and I ran it four times and it was very, very successful for the people who went through it that they were able to move through the season of overwhelm, or season of chaos, or audition season with a much clearer and more confident mindset, and make smarter choices and more proactive and productive choices. So by them making those changes the way they were interacting with me changed. So it definitely felt more productive this year, but still very, very busy.

Peter: Busy. Yeah. And so, just, I have a curiosity I need to pick. I don't know if you pick curiosities, but that's what I just said, so that's what I'm doing. The workshop that you described, did you create that or was the idea for that manifesting itself, did that manifest itself in summertime last year in your creative time?

Jen: You are so good at revealing blind spots. You really are. Because no, I did not create that course during my season of creativity. I created the course after this, sort of, mini audition season that happens in the Fall, and I could feel people needing more practical tools to help them make the changes in their lives and careers that they wanted to make. So no, it did not require my season of creativity to create this thing. Interesting. Interesting.

Peter: To be honest, that wasn't the answer I was expecting. I was expecting you to say, "Well, yes, that is when I created it - in my creative time," because I know this podcast, for example, the idea for it, I believe, and most of the upfront execution that we did before we launched happened last Summer during your creative time. The idea for you to double down and pursue your book happened for you in Summer last year. So like, I love this idea that you have and this structure that you have, it almost feels like, you create, then you test, you learn, and you go back and you create. And I know, like, this in terms of startups and development cycles, this idea of create/test/learn is, like, littered throughout the ways that you can develop software and all sorts of things. And so it like it, it just dawned on me that it almost feels like you've got a little bit of that baked into your twelve-month period, which I love. This is where I'm thinking I could do with something like this.

Jen: Well, you know, it's really funny, because now that you say that, the, all of the seeds that were harvested to create the new course were actually indeed planted in the Summer, because last Summer, you know, cause you were there at least virtually, we came up with the idea for the podcast. I started writing the blog - although I didn't release it until the fall - I started writing the blog in the Summer. I came up with the idea for the book in the Summer. I started having these, like, crazy creative dreams in the Summer, a couple of which have been spoken about on this show, and the blog was really the initial laying the groundwork for what ultimately became the course. So yes, you're right, it did start in the Summer.

Peter: Well that's, that's exciting. That was what I was hoping you would say, because I think, what I'm, like, putting together at the moment in my brain is, we have spoken about before, and I've got my head around on a micro level, this idea of creating space for yourself to think and creating space for yourself to, for me it's bust out a whiteboard and do some noodling and thinking on a whiteboard, and that, you know, adding a couple of hours into your calendar every week or here and there is important for us to have a chance to think creatively and build stuff. But what you've actually done, it feels like it's like, extended this to a macro view, which is like, "I actually have a three month period where that is, that is kind of what I tend to do." And me, personally, I do not have that. And I love the idea of somehow creating some sort of structure where that could work for me. And I think there'd be a number of freelancers, creatives, performers, entrepreneurs, employees out there that would feel the same way. It's like, what if you had a two-month period that was your "create stuff" period. I love that.

Jen: So I think one of the benefits of working in the industry in which I work is that the seasons are, sort of, prescribed by the industry. It's funny, a friend of mine who owns her own makeup company, she was - it's not even worth going into the story - but basically there was a, an issue with one of the concealers; she had to find a new lab, so now they're launching this new concealer. And the, it would make more sense for her to wait to launch it because apparently there are three seasons for launching beauty products, but her customers are so eager to get their hands on this new concealer that she's going to launch it in June, which is apparently, like, a time you don't launch beauty products. So, um, what, what's interesting about that is that she has her seasons as per the sort of cycles of her industry. I imagine that every industry has its own interesting cycles. So it might be worth looking at that. But knowing that there is a pattern in my work, what it has afforded me, and - this is quite literally how I do this - I think you might've seen my, like, big macro calendar at some point, is I have a two, a two-page layout in my calendar that shows the entire year, and I have my major ship dates on there. So, I tend to know what I'm working on twelve months ahead, and I update that every quarter. So I always have this sort of like, twelve-month view of where I'm going and how it lines up with the season. So I would never put a ship date in place in February. I just know that I will miss the mark there. But I do have, you know, "Deliver a first draft of the, the book to the people who I'm gonna ask for feedback on it from" by September first - that's when that's going out. And I feel like I can make good on that. And I put that date in the calendar last October, I think. So, that date has been in there, and I feel like I can make good on it because I have a sense of the waves of dizziness and freedom.

Peter: Okay. So here it is: the moment that I unlocked something. I said at the start, "I feel like that 'Aha!' moment could come from this," and it just came to me.

Jen: [gasps] Let's hear it!

Peter: What I like about this is that it gives you permission to focus on something, and as a result let go of something else. And so what I, because what I tend to do is, I do this subconsciously. I'll spend a week focusing on creating a new keynote that I have to deliver in three weeks time, and then I'll beat myself up for not spending enough time talking to one of my clients, or not spending enough time setting up the next altMBA, or whatever that thing might be. And I will feel guilty, because I've focused too much on one thing and not enough on the other. And so I love that this, this idea of creating, versus testing, versus chaos, versus, like, space - baked into that is this permission to focus on one, two or three things, or to have a certain mindset for that period of time. And there's a classic analogy I've, maybe have mentioned on the podcast by a guy called Derek Sivers, and it's about a donkey standing in the field, and he's got a trough of hay on one side, and a trough of water on the other side, and he's hungry and he's thirsty, and he can't decide, "Do I eat, do I drink, do I eat, do I drink, do I eat, do I drink?" and he falls over and dies of dehydration and starvation. And the moral is, like, you could, you could have both. You just need to pick one first and not beat yourself up because of that. So start with the hay, and when you're done with the hay, have some water. So what I like about this, again, is I could start with creating for a month or for three weeks or for three months, and then I could think about executing after that. And that the permission to not have to do both at once is so freeing. So that's my little "Aha!" moment. Thank you very much, Jen Waldman.

Jen: Oh my gosh, I love that. It reminded me of something my brother in-law was telling me about: he and my nephew have been touring a bunch of different colleges cause he's got, you know, a bunch of acceptances that came in, and you need to make a decision about where he wants to go, and he's going to be studying engineering. And his dad, my brother in-law, was telling me about, at one of the schools, the engineering building is an eight-story building, and each floor represents a different part of a process. And yes, what you learn on the first floor is ideation, and what you do on the second floor is innovation, and on the third, fourth and fifth floor are R and D, and so on and so forth. And what I love about this is this idea that you have to literally, in that building, get on the elevator when it is ready to take it to the next floor, and you can't skip a floor. It's like, you can't go from two to eight. You got to go from two to three. And it sounds like the way you've just, sort of, wrapped your brain around seasons is that what it does is give us some, some sense that our process is making sense.

Peter: Yeah, exactly.

Jen: So, I'm going to now start thinking about my seasons as being a vertical building where I'm going to take the elevator from the Summer, which is when I'm getting all of my good ideas, up to the next floor, where I'm going to test the ideas and iterate and research and put them in a format, and then I'm going to implement and actually bring them to the market, and then I'm gonna start all over again with what's the next cycle of creation. I just, I love that so much. That's cool.

Peter: We're going to install a slide that you can get from the top floor down to the bottom when you start all over again.

Jen: How about a fireman's pole?

Peter: A fireman's pole. I feel like you could definitely get down with that. And it feels like, Jen, with that metaphor, it might be a good place to wrap up, and say that is The Long and The Short Of It.