Teaching Transformations Podcast Episode 7: Our Relationship with Time

Teaching Transformations

Our Relationship with Time

How has Tim and Ryan’s relationship with time changed over the years? The two friends discuss transitions in their responsibilities and how it’s affected their daily work habits. They also ponder the meaning of leverage while applying it to their current careers.

The Teaching Transformations Podcast. Join Tim Desmond Ryan Wooley as they help teachers in their late forties or fifties to design a post-academic life.

Seize the Day!


Ryan  0:00  

Jeez, man, up until two seconds ago, my hands were shaking.

Tim  0:05  

Alright, explain.

Ryan  0:08  

Well, you know, every day is a run-around. Typically, I live like forty-five minutes from school. My typical day involves some sort of early morning practice, and I get up anywhere from 4:15 to 6:15 to kind of get going, and then get kids where they need to be. Then I start my workday, and after the work day, there’s more practice, there’s getting kids from whatever school they’re at. I’m used to the run around, but this morning, Christina offered to take Preston up to school because I was kind of nursing a headache, and she was like, yeah, you can sleep a little longer. I’ll take him to school and just come back home. You take Franceada to school. Then in the shower, she lets me know, oh, I forgot I scheduled Preston’s orthodontist appointment for 8:40, and by that time, the math just wasn’t adding up. I’m picturing myself on two wheels going around turns, and it was just a scramble. I mean, I had to get Francy to school, I had to rush up to Preston’s school to get him, I had to rush to the orthodontist. We were still five minutes late, but this was after, I hate to say this because I’m usually a really careful driver, but eighty on stretches of the expressway and stuff, so then I just got back here. Normally, I like to get set up and collect my thoughts, get some notes together and everything, but I literally just got my computer started, worked through a couple of the typical tech issues that we have every week, and here I am. I think we’re gonna talk about this whole time thing today, but, man, sometimes the reality of just the daily grind for all this stuff.

Tim  2:28  

Yeah, every day is a challenge in that way.

Ryan  2:36  

Yeah, so I’m in the middle of it. We’re both in the middle of it. I think because of the nature of our paths, we experience it in different ways, but we’re in the same life stage. I mean, both of your children are still in high school for the moment. You have one that’s going to graduate this year, right?

Tim  2:58  

Correct. Yeah, we’re getting the college offers coming in now, and it’s kind of weird.

Ryan  3:03  

Yep. So, I think for both of us, we’re still in that same stage, but we’re also kind of seeing what’s coming next. It’s an interesting place to be because I can’t really change this reality right now, at least not drastically, but I can look at what’s right around the corner and start to think about, well, how will life be a little different then? I’m thinking about this stuff a lot because I know it’s coming, but it also seems so foreign. My life has been like this for a long time, and if I have newfound time, it’ll be like I’m meeting it for the first time, and I won’t even know what to do with that.

Tim  3:54  

Yeah, it’s different. It’ll feel different than it did before you had kids too.

Ryan  4:01  

Yeah, the way I want to use my time is different.

Tim  4:06  

It’s just your appreciation of it like you don’t even know before you have kids. I have two, not three, but things are changing really fast here, too. It looks like Brady’s gonna be going out of state almost certainly for college in the fall, and in October, Brenna turns sixteen, and we have two cars. He’s not taking a car to college, he’s going to be away, and she’s gonna be able to drive herself, and that’s crazy to think about, like there won’t be many of those old dad responsibilities that I’ll still have to fulfill when it comes to chauffeuring kids around and making appointments and that kind of stuff.

Ryan  4:53  

Yeah. Is it Stockholm Syndrome where you like develop a kinship with your captors?

Tim  5:03  

I believe that’s correct, yeah.

Ryan  5:06  

I feel like I’m gonna have this relationship with time. I’ve seen other people go through similar transitions where, you know, they develop an affinity for the thing that drives them crazy, and I want to make sure I don’t fill my time needlessly with things just because that’s what I’m used to.

Tim  5:31  

You will temporarily. I’ve talked to other friends of mine who have left their day jobs to pursue writing, and all of them say like, yeah, even up to the whole first year, you’re still doing things based on habits and things that’ve worked for you in the day job. It’s not that they don’t work, but they’re not necessary, but you still do them. That’s everything from alarm clock and wake times to when you do work or when you think you’re supposed to work, all the way down to really what most people consider radical things like mealtimes and what you eat and how you eat. It’s amazing. When you step outside of the structure, you realize, wow, I can really do anything I want. I can recreate my life in whatever fashion I choose.

Ryan  6:31  

That just seems crazy. I mean, I know it’s there, but in the moment, I have trouble even relating to that.

Tim  6:41  


Ryan  6:44  

Well, I know we’ve talked a lot about our different paths, and we’ve drawn focus around yours in a lot of ways because like we’ve said, you’re kind of on an accelerated version of what all of us are on our way to, which is some form of a second act where we maybe get to let go of this kind of structure and have a little more control over our own schedules and our own destinies. We just got done saying how we’re in the same life stage except, you know, you are a year older than me.

Tim  7:30  

Not that you ever remind me of that.

Ryan  7:35  

We’re kind of in the same place, but we’re also in very different places, too. Can you talk a little bit about how your schedule really changed when you made your move to leave education? Give us a little sense of what your day-to-day looks like?

Tim  7:59  

It wasn’t easy. I think for a lot of professions, there’s more flexibility than there is for teachers–we live and die by the schedule. It’s impossible to keep that from bleeding over into your personal life, and you end up managing your time outside of the classroom the way you do inside the classroom. It’s regimented, it’s regular, it’s cyclical. All that goes out the window when you remove the constraints, for better and worse, like there are really great things about my time now, and there are things that are really challenging. On a high level, high altitude, it’s important to realize that the grass isn’t greener, the challenges just change. They shift, and they may shift more in your favor based on how your brain is hardwired, or they may not, but it’s a different set of challenges. We talked a little bit about the adjustment. Let’s put the adjustment phase aside, and let’s say you skip over those first awkward three, six, nine, twelve months, whatever it takes to kind of break the routine that you’ve had for years or decades. Let’s skip ahead to okay, you’re out of that, and now you’re completely in charge of your time. For me, some of the great things about that is I value my independence more than anything else, more than money. I don’t care about money unless it affects my ability to be independent. I don’t chase dollars for the sake of it. It’s not a game to me. It’s just a means to an end. One of the advantages to that, I guess, is that you do have complete freedom. I can do stupid things like calling a plumber out. I don’t have to take off a day of work, I don’t have to coordinate that with my wife, I can just be here and be in that window, and I can work in the window until the plumber, the electrician, or whoever, shows up. Then I can go back to my thing, and I don’t lose a lot of transition time. I’m not driving from the office or from the classroom back to my home to meet the person and then back to school, so that’s all an advantage. The disadvantage to that is I’ll get messages from Joy, and she’ll be like, can you pick up such and such, can you do this, can you get this, and I’m like, I’m working. I’m home, but I’m not just laying on the couch. I think most, if not all, people were well up until the pandemic working from home. You’re just sitting on the couch not doing anything. It’s not a time for me to run errands, you know. I think that’s one example of how it plays out on a real practical level. You have complete control of your time, but there’s also these downsides to it. I don’t know, am I getting an error with that?

Ryan  11:24  

Yeah. I mean, after you sleep in till ten or eleven, you know, 4:30 you’re on call, right? It’s funny to say that with you because I know that that’s kind of the opposite of you. I think you get up for bed as early as you ever did, don’t you?

Tim  11:45  

Yeah, so this is another crazy element of time. I haven’t used an alarm clock since I left teaching, and I never would have predicted that. I think I’ve always been a morning person, and I’ve always enjoyed getting up early. When I was teaching, I would have to set my alarm to get up and get my hour or so of writing in before I started my day and help the kids and things. Again, once those external constraints were gone, I transitioned into this phase where I’m like, I’m just gonna go to bed when I’m tired and wake up when I wake up, because why not, right? This was that retraining my brain about, well, you don’t have to get up at a certain time. Now my kids make fun of me because around eight o’clock, and it’s hard in the summertime when it’s still light out and kids are playing in the yard, around eight o’clock, I start getting my things together to go upstairs. I like to read for about an hour before I go to bed, so I’ll do a few things, I kind of set my agenda for the morning or set my things out like my workout clothes. I’ll go into the bedroom about eight, and I’ll read for about an hour. I’m usually asleep between 9:00 and 9:30, and then I wake up at 4:35 at the latest, and it happens every day, and every night I get tired at the same time. It’s just weird. I guess that’s how it should be. I’m not sleeping in, I’m not staying up late, I’m not getting any more or less sleep than anyone else or myself, but it’s just with the freedom, I let my body take over, and it naturally falls into this rhythm.

Ryan  13:37  

It’s so funny that you would have the ability to sleep in if you wanted to. To a certain extent, you still have the same run-around in terms of getting people where they need to be, getting groceries and all that, but it’s just funny that your version of freedom looks very much like a lot of our schedules in many ways, you know, you’re up earlier than probably most people are.

Tim  14:09  

There’s an occasional day where I’ll wake up at 4:30 or 5:00, and I don’t feel well or I just don’t feel like getting up yet, and in that case, I can roll back over, and maybe I’ll lay there or fall back to sleep for half an hour or an hour at the most. That’s where freedom comes in. I can totally do that. I don’t have to jump up at that time, but it’s weird because that doesn’t happen all that often.

Ryan  14:33  

Yeah. So with this freedom, which I’m sure is nice in many ways, although as you’re describing it, maybe not all that different from anybody else’s life, but there’s also got to be some pressure that goes along with it, right? I’ll continue to get a paycheck if I show up to work whether I’m optimized or not, whether I’ve really planned out my day well or not, the paycheck will continue to come in, and that’s kind of a security blanket that probably a lot of us take for granted. For you, it’s not like that. Your time, your productivity, you really own it, and it has to be there for you to get a paycheck, and I would imagine that comes with a different type of pressure.

Tim  15:36  

It does, and it’s very challenging. I can’t say I’ve got it figured out yet, and I can’t even say I’m good at managing it. I think too, for most of the listeners, this is not going to be your situation. It could be, but I don’t think it’s going to be my situation. When I quote unquote retired from teaching at forty-seven, it was not, okay, now I can start drawing down my retirement funds like that. I needed to work still even though I retired from teaching. I’m a pretty type A personality, like I like to take charge of things, I like to get things done, and that can be hard at times. I think we mentioned in another conversation that I really don’t have weekends or vacations anymore. I mean, I coordinate downtimes with my family schedule, but I don’t ever have a day where I feel like I can totally check out or I can just be like, alright, I’m not doing anything today or let alone a week. That’s almost unimaginable for me at this point because I’m a solopreneur. I’m running my business myself, you know, I pay a few VA to do a few tasks, but it’s me, so if I’m not working with clients or doing editing jobs or contributing to my author community, I don’t get paid. There’s a real pressure there, and it’s beyond the obvious. The obvious is, well, of course you can’t just play video games all day or play guitar all day long and not worry about it. The added pressure comes when you have fifteen or twenty minutes of downtime, and I have this inner argument. Do I pick up a book and just read for twenty minutes? Do I go for a stroll around the neighborhood? Should I be creating that next blog post? Should I be working on the podcast? That is a real struggle, and it’s in those margins where it’s the most challenging because logically, I know I can’t work all the time. I can’t work every single hour up, but when I have those spaces, I have this guilt of like, well, you should be because if you’re not, you’re not working on your business. That’s a bit of a nuanced element that I really was not aware of or couldn’t anticipate. It’s very real, and I go through phases. Sometimes I’m really good at being like, screw it, I’m just gonna go read. I know I work too much.

Ryan  18:30  

And that’s different from the reality of someone in a conventional situation like mine because everything connects to that equation for you. All of your time could be sort of productive, income generating time, if you wanted it to be, if you were willing to just let all of it be dedicated to that, but then you would be miserable. There’s math involved there that a lot of us just don’t even have to consider.

Tim  19:09  

I hate to say it, and I’m certainly not talking about anyone specific, but I think one of the criticisms that’s legitimate with education these days is that there’s not a lot of merit-based compensation. If you’re in a public school, and you get tenure or whatever, you’re kind of protected. Even in private schools, if you’re doing a mediocre job, you can kind of skate by for years. It doesn’t necessarily figure into your compensation, so you can kind of go through the motions, and we know people who have, you can go through the motions and still get the same paycheck you would be as if you were all-in 100% of the time, and you can coast. When you’re in business for yourself, you can’t ever.

Ryan  20:10  

Well, we’ve talked about this a bit. It’s probably been a while, but I know that a book that both of us read was The Four Hour Workweek by Timothy Ferriss. What that book did for me was it reoriented me to the value of time, and not just my own value of time, but also the way that time is valued in our society. It really is how people get paid, you know, it’s you get paid because you were here for forty hours, not because you were productive. Many people are productive, and some people work, especially salaried folks. Teachers put in hours beyond the typical eight to four or nine to five workday, but by and large, everything is structured around getting paid for time, and it sometimes has little relationship to productivity. That’s one of the cool things there. I’m sure it comes with its own pressures, but that’s one of the cool things about your situation is it’s really based on being productive, and sometimes that’s being smart versus just throwing hours at a project, right?

Tim  21:31  

Yeah. We’ve both had colleagues who were busy as a badge of honor on their sleeve, and it always, man, that just pissed me off every time I would run into that. It would make me angry because the assumption is like, look how hard I’m working. Why aren’t you working this hard? You can’t always say it this way, but you want to like, well no, you’re just being stupid. You’re just randomly fleeing time everywhere, and you’re patting yourself on the back for that because it appears that you’re important because you’re in this chaos. You’re in this Cyclone that you’ve put yourself in, and you believe with that comes some sort of prestige or respect. One of the things I’ve always known in my heart is that time doesn’t equate to quality. There are certain obvious things that yeah, if you spend more time doing something, you’re gonna get better at it, but it doesn’t necessarily mean that’s always a direct correlation. I think especially now with a lot of the technical tools that we have, is you should be working less, not more. I think the further I get into this, like, I haven’t necessarily counted hours because it’s just not in my DNA, and it feels trivial to me and pointless, so I don’t even know how many hours I work. I do what I need to do, and then I don’t, and that works. It’s been working for me for four years. I kind of lost my train of thought here on the time element. It’s the people who I admire the most and the people who are in my space are working fewer hours, and I think I’m seeing that, too. I’m seeing time more strategically. I could spend thirty minutes crafting an email. Now, that could potentially earn me a month’s salary as a teacher, and I mean, that’s realistic. I’m not bragging about that, that’s just the reality of the business situation that I’m in there. When you run your own business, there’s no ceiling, there’s no cap, but when you’re salaried, your pay is your pay. Does that mean I should be working thirty times harder if it took me a day to write that email? Not necessarily. Again, there’s this guilt associated with sacrificing some things. I’m sacrificing security, job security, to earn the extra money. Shouldn’t I then reap the benefits of that with some more leisure time and not working as many hours? I don’t know for sure, but I’m certain I’m working less hours. I’m putting less minutes in now than I did before, and I’m making significantly more money.

Ryan  24:51  

Well, the word we haven’t touched on yet is leverage. When you work for yourself and you have control over the variables, you can have leverage that you just don’t have in a conventional situation.

Tim  25:06  


Ryan  25:07  

This idea that you’re talking about where you can write an email, I want to see this email by the way, that you can write and earn a month’s worth of salary.

Tim  25:20  

It’s nothing special. It’s just affiliate sales. It’s putting someone else’s product in front of your audience and earning a percentage of the sales from that. That’s all it is.

Ryan  25:32  

Yeah. Most of us that have been in education, we’ve never had these kinds of levers. Again, back to the whole time thing. It’s kind of like a foreign concept to most of us because we probably assume stuff like that happens, but it’s just not part of our world. That’ll take some acclimating. Just even recognize that there might be possibilities out there that look markedly different than the normal sort of exchange, time for money that we’re all used to.

Tim  26:08  

It’s not linear growth, either. That’s the other thing that’s hard to wrap your head around. You can work on your own business for three years and feel like you’re not making any progress or you’re not earning the money that you want, and then all of a sudden, things can lift and you’re then at another level, and then you plateau. It’s not strictly linear. I think that’s hard to manage because you can’t predict it, and you don’t know how high the hockey stick is gonna go the next time you hit that little bump. That’s another challenging part of this.

Ryan  26:50  

Another term that I think is probably relevant here is passive income. That was part of the Tim Ferriss argument, I think was to structure things to generate passive income so that you could live a lifestyle without having to constantly feed time to it. One of his big stories in that book was when he realized there were some subtle changes he could make to his business that would free his time and basically allow a similar amount of money to continue to flow to him without him having to be on it 24/7. I think he had to have a freakout moment when he was supposed to be on vacation. He basically kind of had a mental breakdown that forced him to reconcile with that. Do you play around with this concept at all? Have you created sources of passive income? Is there such a thing?

Tim  27:56  

Well, I don’t know if I disagree with Ferris. It’s been a long time since I read that book, but I just don’t think passive income is real. If you hear people talking about it, it’s not really passive income. Let me give you an example. I will hear people outside of the publishing industry say if you’re an expert in something, you need to write a book because that’s great passive income. Now what they mean is, and this gets into the difference between products and services, what they mean is if you can create a product, that product then can sell endlessly, especially if it’s in the digital realm, but that’s not passive income. You’re a writer, you know, there’s nothing passive about writing. What people don’t see are the hours and the days of work that go into writing that book and revising it and publishing it and working with the editor and the marketing and the promotions. Especially my friends who are writing fiction, by the time they publish their book on Amazon, they’re three or $4,000 in the hole. Months, if not years, working on that. Once they publish, once they move from the red to the black and they’re now earning money at that point, then technically, it becomes passive income because they don’t have to do anything. It just sells, but it’s not passive, right? You can even take it to real estate. It’s really hot right now, everyone’s investing in real estate. That’s not passive at all, like the number of hours of research you have to do on neighborhoods and the management and on home repairs and dealing with tenants. That’s not passive, but people just see well, I own something and money comes in on a regular basis. True, but not passive.

Ryan  30:06  

When did you write your first book?

Tim  30:10  

Ah, I think I wrote it in around 2009, 2010, something like that.

Ryan  30:18  

If you think, how many years ago is that now? Geez, twelve years ago? That went fast. So, twelve years ago, you started writing. You’ve had different periods where you’ve been more prolific and some times where you’ve pulled back from writing and focused on other things, but you’ve been writing now for a long time. I can’t remember now how many titles you have out there, but I know it’s kind of astounding.

Tim  30:53  

I’ve lost track.

Ryan  30:54  

Those are all still for sale out on Amazon, right?

Tim  30:57  


Ryan  31:01  

I get that you worked for that, so it wasn’t passive, but in terms of some of those books that you were finished with years ago, do they continue to generate you income? Or is it negligible after a while? The ones that have been sort of sitting out there for a while. Is that why you have to just keep writing because the sales fall off of those early ones? I just don’t even know what that’s like.

Tim  31:29  

For me, I wasn’t smart about it. I didn’t have a plan. Most of those books, the sales are negligible. There’s certain things indie fiction writers know now that nobody knew in 2009. One of those is writing in a series. There’s statistics on this that if you write in a series and you’re using paid advertising or even not, you don’t see return on investment till you hit books seven or eight because the profit margin on books is so small compared to other products and services that you have to sell a lot, and you have to sell it sustained over time. For example, if you put a novel on Amazon and you sell it for $2.99 on E book, you’re gonna make about $2.10 per book. You got to sell a hell of a lot of books at $2 to really have it make any kind of a dent. If you write in a series and people are really engaged, then it’s another $2.10, and you’re trying to drive them all the way through the series. There are indie authors like my friend, Lindsay Broker, who makes a complete full-time living on fiction alone, and her back catalogue is probably still selling thousands of dollars a month. I didn’t do that. I wrote a lot of standalones, I wrote in different genres, I jumped around in different series. All those books are there, and they might sell a handful of copies a month. It’s not even worth talking about.

Ryan  33:12  

You need some of these teachers that are listening to this podcast to adopt some of your fiction into their classes so it becomes a required high school reading.

Tim  33:25  

Yeah. I don’t know, the book business is really hard. I do it because I love it, but if I were looking at business opportunities strictly from a profit margin standpoint or return on investment, writing and publishing books will be at the bottom of that list.

Ryan  33:45  

Yeah. I don’t know the percentage, but I know there are a lot of authors that are famous that we read that are part of the so-called canon that didn’t make much money from their writing. There are a few exceptions, but I think a lot of the authors that we’re familiar with, you know, that wasn’t a ticket to riches for them.

Tim  34:15  

No, I mean, we’re very quick to recognize the JK Rowlings and the Stephen Kings and the Dean Koontz and the James Pattersons of the world, and they are like a fraction of a fraction of a fraction of a percent. I’m not trying to be negative, I’m not trying to dissuade anyone or be pessimistic about it, I’m just trying to be realistic about it. Amazon will publish stats from their KDP dashboard occasionally, and the average indie author makes like $18,000 a year on their books. The average self published book on Amazon sells less than 200 copies in its lifetime, so the odds are really against you as far as that goes. Again, I come back to this idea of revenue diversity. It’s just not safe. If all of your revenue is coming from a single source like book royalties and something happens to the industry, what do you do? You’re wiped out, you have no alternative. It’s almost like if you were fired from your job, so I think having different business models and different projects is important which is why I’m constantly starting different projects, looking at different industries, investing time in different places. I want to have twenty, thirty, or forty revenue streams bringing me in a couple hundred bucks here and there than just one that I’m relying on for my livelihood.

Ryan  35:50  

Are there any good models that you’ve encountered in the past few years? Are there people who you feel like have really kind of cracked this nut in a way that serves as a good model for some of us?

Tim  36:06  

Ah, it’s hard to say because I’ve been pretty insulated, especially in the past four years, being really in the author community, but there are a few people who I know in the author community who are in this model, and almost all of them who are successful have other sources of revenue besides book royalties. I can say that across the board. My friend, Lindsay, I was just talking about, she has real estate investments. My co-host on Writers, Ink, JD, he’s got all kinds of business interests and things going on. He basically told me at one time, if the book industry disappeared tomorrow, he’d be fine. He has other investments, and I don’t just mean stocks and bonds. I mean other business investments. I think that’s important to recognize because again, I don’t know how much this will apply to people who are heading into a more traditional retirement phase because they might already be funded for that. However, people who want to try something, and they asked me about being a full-time writer, and I’m like, it’s not what you think it is. It’s not sitting in a cabin in the woods typing up a great story and then handing it to someone and getting a paycheck. There’s a whole lot more that’s involved, and the more diversified you are in your interest and your investments, the better off you’re going to be.

Ryan  37:29  

Yeah. If you love to do it and that’s really what you want to spend your time doing, there’s an opportunity to make some income there.

Tim  37:41  

Here’s the flip side, I mentioned earlier that if I were going to go into a business, book writing and publishing would be at the bottom of that list, but that would be under the assumption that it has to support me and my family. If you’re talking about just generating another revenue stream, if you’re talking about a side hustle, if you’re talking about monetizing a hobby, if you want to do something after your teaching career is over that still earns you a little bit of money and you enjoy it, I think there’s nothing better. I think it’s at the top of the list because you are in complete control of what you do. You can be creative, you set your own schedule. If you do things right, you will earn money, you have the potential to earn a lot of money. I’m saying potential like if you study and you have a little bit of luck and things break your way, you could potentially make a lot of money. In that circumstance, I would say it’s one of the best things you could do.

Ryan  38:42  

Interesting. Well, I think we’ve explored this topic as far as we probably can. It’s probably not the sexiest topic, but at the same time, it’s one that everybody has to reckon with. I mean, how you use your time is kind of everything, and I think it’s important to be aware that what you can do with time, how you engineer it, the options that you have, really probably changes pretty drastically and being ready for that. I’m trying to be ready for that whether or not I retire conventionally. My relationship to time is going to change, but also, I value time differently. I think you mentioned this earlier. I have a different appreciation for time than I did in my twenties, like I wasted a lot of time. I’m sure a lot of us have, but you know, it’s more precious now, so I want to be really actively thinking about and orchestrating the best optimal use of whatever time I have left.

Transcribed by https://otter.ai


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