Teaching Transformations Podcast Episode 13: Using the F-Word – Finance

Teaching Transformations

Using the F-Word – Finance

Sales, scams, and charity. Tune into this week’s episode for a captivating discussion surrounding the definitions of work and how they can be applied to the current way you make income. 

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!


Tim  0:00  

Welcome to Teaching Transformations: Designing Your Post-Career Life with Tim Desmond and Ryan Wooley.

Ryan  0:01  

Just noticing your label there. Sleazy Sales Guy.

Tim  0:03  

That’s me.

Ryan  0:04  

We’ll come back to that. Do you have any pets?

Tim  0:06  

No, we’re not animal people.

Ryan  0:33  

Okay. I wondered about that. I don’t know why. We have two dogs, and they’re biological brother and sister, and they’re ten now, so they’re getting more needy. I was going to show you this picture. The one of them has allergies that we’ve been chasing down for the past few months, and we can’t figure it out. We keep eliminating things from the diet to see what changes things. I mean, she blows up with hives all over her if she eats the wrong thing, and we don’t know what it is. They sell these tests now where you can like take a saliva sample in and send it away, and they’ll analyze it and try to tell you what’s going on.

Tim  1:27  

This is so outside my world. I’m completely fascinated right now.

Ryan  1:30  

Here, look at this picture.

Tim  1:32  

Oh my god.

Ryan  1:33  

That’s what happens to her when she gets the wrong thing.

Tim  1:36  


Ryan  1:38  

Here’s another one.

Tim  1:39  

I thought dogs caused allergies, I didn’t think they got them.

Ryan  1:44  

Yeah. Then the other one, a few months ago, he kind of like fell off the bed really early in the morning. It turns out he had this mass on his spleen that had ruptured, and it was a weekend, so we had to rush him to this emergency hospital where they did emergency surgery. Luckily, it didn’t end up being cancerous.

Tim  2:12  

How much did that set you back?

Ryan  2:14  

Oh, $4,000.

Tim  2:18  

 I’m not laughing at your dog, I just, oh my god.

Ryan  2:22  

I know.

Tim  2:22  

How do you budget for something like that?

Ryan  2:26  

We don’t.

Tim  2:26  

Do you have a dog fund?

Ryan  2:28  

No. We need some pet insurance or something.

Tim  2:33  


Ryan  2:34  


Tim  2:34  

 That is crazy.

Ryan  2:37  

It’s not the first time either. We’ve had other weird, different dogs, but one of our dogs had a weird fracture in her wrist, and we had to take her to OSU for a special surgery for that to fuse the bones together, and we’re never gonna say no to that. For us, they’re like family.

Tim  2:59  

Did you and Christina grow up with pets?

Ryan  3:02  

I had dogs growing up. I think she did, too. For some reason, we’ve made it a point to have two dogs since we’ve been married, so we’ve always had at least two, and that just multiplies the care.

Tim  3:23  

I have a theory. I think people who grow up with pets are more likely to have them and people who don’t aren’t. My wife and I had a dog here and there, but neither of our families had pets on a regular basis, so maybe that’s how it starts.

Ryan  3:38  


Tim  3:39  

Your kids will thank you someday.

Ryan  3:41  

Yeah, I’m sure. So today I want to talk about every academic’s favorite topic.

Tim  3:52  

The F word?

Ryan  3:54  

The almighty dollar.

Tim  3:55  

Finances. This is the F word when it comes to education.

Ryan  4:02  

You’ve been around educators for a long time. How would you describe their relationship with money?

Tim  4:09  

I had to put this in the notes for myself because I don’t want to forget it. My initial reaction was talking money with educators is like telling them about your latest colonoscopy. They don’t want to hear it. They don’t want to know about it. They don’t want to know if you have it or not.

Ryan  4:26  

That is so funny. I wonder, why do you think that is? I would agree with you. That’s been my experience, too.

Tim  4:33  

Yeah. I don’t know. It’s real, though, and I think there are certain factors that play into this. I think one of the major ones is that educators have been historically underpaid forever, and that’s not changing. I think that over decades, over generations of being one of the most underpaid professions, in my opinion, teachers don’t value money. They don’t value themselves, and there’s some sort of weird shame that’s involved in talking about it as if you would just teach for free. Like, it’s such an altruistic profession that no one ever wants compensated for it, which is, you know, whatever.

Ryan  5:15  

Well, I think that complicates that a little bit. I do think most teachers are motivated, at least in part by wanting to do good, right?

Tim  5:26  

True, and thank God they are because they have to be almost.

Ryan  5:33  

Yeah, but it’s funny, I feel like it does kind of take over. Maybe it’s a way of self-explaining like, okay, this is why I’ve accepted a low paying profession when maybe I could have done something else. I feel like maybe we latch on to that reason, and it sort of inflates, you know, becomes a bigger part of the reason that we become teachers.

Tim  6:06  

You think it’s a badge of honor amongst other teachers to not emphasize money or not emphasize compensation?

Ryan  6:14  

Yeah, I do. I don’t share that. I wouldn’t teach for free. I mean, I enjoy it, and I love the fact that I do feel good about the work that I do, and that is important to me, but for me, it’s a “both and”. It’s like they need money therapy. They need somebody to tell them like, no, it’s okay, we all need it, it’s nothing to be ashamed of.

Tim  6:51  

You have to pay your bills.

Ryan  6:52  

Right. I mean, we’re not talking about like country club memberships and Mercedes’, we’re talking about all the things that are noble that we have to spend money on just for a living–putting our kids through school, you know, paying for our…

Tim  7:11  

Putting your dogs through surgery.

Ryan  7:15  

Yeah. Things cost money in it, and money’s stressful. When I think about reasons I wish I had more, it’s mostly just to remove that stress. I feel it, like when we had that $4,000 suddenly, you know, that bill, we didn’t have $4,000 just sitting there waiting to be spent on something. We didn’t feel like we had a choice, and I don’t know how many more of those are around the corner. What if something else weird happens? We’ve also had those unexpected car repair costs. Last year, Christina’s transmission suddenly failed, and we had to spend like $3500 out of the blue just to keep the car on the road.

Tim  8:13  

Yeah. We both have a mutual acquaintance who we won’t mention by name, but he’s about our age, and he’s had a long career mostly at boarding schools. I had a conversation with him one time, and he said, not in like a snarky way or an egotistical way, but he said, like, money just isn’t one of our concerns. They have other concerns. They have concerns with their kids and family issues and things, but he’s like, money has never been a concern because if you teach in a public school, you might not know this, but if you teach at a boarding school, most of the time, your housing and a lot of times your food is completely taken care of by the school, so you can really sock away a nice chunk of your salary because your main living expenses are covered. On top of that, if you work at a boarding school, you don’t drive or need as many cars. Basically, what this guy was saying is, all those years, they were just kind of saving that money, and now it’s not a concern. I remember him telling me that, and I was in the classroom still at the time, and I was just thinking, like, I can’t even imagine that. I can’t imagine not worrying about money.

Ryan  9:25  

I have two follow-ups for that. One is we lived at a boarding school for six years, and there was a guy there that had five children, and I remember him at the dining hall. They didn’t miss a meal, and he was giddy about it. He was like, eat up kids. This is part of the daddy salary right here. The other piece, you know, the whole thing about explaining travel expenses, I mean, I drive forty-five minutes to and from work, and we put 30,000 miles on each of our cars. I think that may have gone down a little just since I have one in college now, but 30,000 miles per car between the two of us. Not all of that’s just getting to school, some of that’s getting to swim practice and all that other stuff. Back when gas was really high, we were spending seven or $800 a month on gas. These are just examples of things. We could have moved closer. That’s a whole story in and of itself and related to the housing bubble. We might actually circle back to that here, but life costs money, and for people who figured out how to not have to worry about it, I applaud them. I give them credit. I just don’t think that’s most of our realities.

Tim  10:58  

No, I think it’s a very, very small portion of people that don’t have to worry about money.

Ryan  11:04  

I looked this up just for today, but this is from a post on annuity.org from a 2020 TD Ameritrade survey. “58% of Americans give their return at retirement a grade of C or lower,” I thought the grading was a nice touch for our educator fans here. “and 46% would retire immediately if they won the lottery.” I just think those are two funny statistics.

Tim  11:33  

Yeah, they don’t surprise me.

Ryan  11:37  

Most people are not feeling good or not feeling prepared. If we polled most of our friends and colleagues, I bet the vast majority would say, yeah, I don’t feel ready.

Tim  11:52  

Almost every one of my acquaintances, this is all anecdotal of course, but almost every person I talked to who’s our age has said they either are woefully unprepared financially for retirement or have nothing, like zero, and I think that’s the case.

Ryan  12:16  

I’ve noticed as I’ve poked around out there, there are retirement calculators. There are a bunch of those out on the interwebs, so you can kind of like plug in, here’s how much I have in my retirement account, and here’s how I want to live, and it’ll let you know if you have enough. I can tell you, I’m not even close, and not that I’m necessarily planning on retiring soon, but when I look at what those calculators tell me, and I look at what I have, I’m like, I don’t even know how I’m gonna get there. I mean, it’s just kind of scary.

Tim  12:54  

I want to put a little asterisk on this, and I think we could almost come back and do a full episode on it because I feel like those calculators are good, but they’re a bit misleading, and I’ll tell you why. I’m not saying we don’t have a retirement crisis looming, but it might not be as bad as those tools would indicate because most of those tools are under the assumption that you don’t want to draw down your balance, that you’re creating a portfolio, and that you’re living off the interest or dividends, and you’re never touching the balance. This is a bit of an emotional third rail on this conversation which is like, Joy and I have already said to our kids, we’re not leaving you anything. We have put you through private school, we will put you through college, and we’ll get you through college with almost no debt, and then it’s up to you. I look at my mom, you know, my mom’s talking about like, well, you guys can have the house when I pass. I’m like, Mom, God willing, that’s not gonna matter to us. My third of my mom’s house is $50,000, and I get that when I’m seventy, that money is meaningless at that point, so I said to my kids, we’re front loading all of our support for you, and hopefully by the time you’re young adults, you’re going to have a career, you’re going to have an income, and you’re not going to be waiting for us to die to use money when you’re middle aged or older. That doesn’t make sense. We’re talking about like a “die with broke” strategy. We don’t need to maintain that retirement balance. What we need to do is slightly outpace our life expectancy, and I think when you look at it that way, it’s much more feasible because it’s not about accruing. It’s not the 4% rule that you hear in the fire community where you’re never going to touch the balance of that portfolio.

Ryan  15:02  

I like that you guys have had a conversation with your children about this, that seems pretty healthy to me. I have this funny image in my head, though, of you and Joy realizing late in life that you have money to burn and that you’re throwing like lavish parties and stuff just to burn through it because you said you would.

Tim  15:28  

Yeah. If you think about it, too, there’s a ton of stuff. There’s a lot of data that shows the older you get, the less money you need. I mean, health crisis is a whole different category, but generally speaking, your living expenses decrease as you get older, so you need less and less, too.

Ryan  15:48  

Yeah, that makes sense. The only little weird variable for our generation, and I think most of us are still feeling it, is the residue from the 2008 housing meltdown. I know so many people our age who got upside down in their houses and are still climbing out of that hole. I mean, literally, I could name you ten people with barely even thinking about it who had that experience. We got hit twice by that because it just so happens that we bought my grandmother’s house really for a bunch of reasons. My friend was renting it from my parents, and things weren’t going well there, so it was in part to try to help out a difficult situation, but I also thought, I’m a handy guy, and the house needed work. I thought, okay, I can sort of ride this out for a bit, and then I’ll fix the house up and sell it, and we can make a little profit. Basically, I borrowed all the money to do all these repairs, you know, siding, roofing, windows, carpet, all that kind of stuff, and that’s right when the housing market crashed, so the house value kind of went… I would say it fell almost by 40%. That was a side project that’s leaving my main home alone, so we really got hit twice by that. Eventually, several years later, that’s a whole saga. We could do a whole episode just about the story as it unfolded for us. The bottom line is we lost a bunch of money. We finally were able to get rid of it, but it takes a long time to climb out of those kind of holes, and I just think a bunch of us, our generation, unfortunately, we really got screwed on that.

Tim  17:54  

I feel really bad for people who were put in a position in oae where they didn’t have a lot of choice. What I mean by that is, they were put into a place where they had to borrow against retirement savings, or they had to take a penalty and do an early withdraw because I think if you didn’t have to do that in the long game, you’ll be okay. I didn’t have to draw my retirement, and even though I saw my portfolio dropped by like 30% in a matter of three months, I was just like, I’m going to put these statements aside, I’m not going to look at them again for another year. Now, here we are, twelve or thirteen years later, and I feel like my portfolio has recovered, but had I needed that money at the time, or had I needed to sell my house? We were underwater for almost a decade after that financial crisis, and I think it’s only because of the crazy real estate market now in the pandemic that our value of our home is higher than it was when we bought it in ’06, but that was ten plus years of waiting for that to come back.

Ryan  19:03  

Yeah, it is finally starting to turn, but think about previous generations. Their houses were appreciated the entire time. They were sort of married and raising a family and all of that kind of stuff, and it’s just not the case for us. I was going to ask you this question–you’d said in a previous episode that you don’t chase money, and I want to dig into that a little bit. I think you’ve already started to answer the question a little bit, but can you explain what you meant by that?

Tim  19:44  

Yeah, yeah, definitely. I’m all about freedom. Sometimes it’s money that buys that, sometimes it’s intellectual capital that does, sometimes it’s tough management that does, but that’s what I chase. I’m not looking for a Tesla or a forty-foot yacht as I would if I was strictly chasing money. I want to be able to get up every day and do what I want to do, and that doesn’t mean lay on the couch or Netflix. I want to do productive, interesting things. I want to build and create stuff, but I want the freedom to do that on my own terms. One of the things I thought would be helpful is I wanted to pull up my own personal dictionary and talk, and because I know where this conversation’s going, I want to create some definitions so that we’re all working from the same place. Is that cool?

Ryan  20:39  


Tim  20:40  

Alright, so I want to talk about what work is first. I know this sounds stupid, but stick with me on this. I have two definitions of work, and when you have an employer, when you’re working for somebody else, it’s a simple equation. It’s time exchanged for money, that’s all it is. You might think you have the greatest job in the world or worst job in the world, but when it comes down to it, you’re being paid for your time. That’s the only way that transaction can go. Now, there are performance indicators that might affect how long you have that relationship, but especially in the school environment, everything is based on time, you know, the minutes teaching time, or the number of classes that is on your load, whatever it happens to be. If you’re self-employed or you own your own business, then work is a little different. Now, in that case, work is activities that generate revenue or opportunity to generate revenue, and here’s the flip side of this. If you’re working for an employer, even in a school, there are certain hours that are off limits for most cases, right? Like, let’s say it’s 7pm, or let’s say it’s the bell that rings at the end of the school day. There’s not any expectation from your employer most of the time, that anything is required of you until you show up the next morning at whatever prescribed time and you have to be. Well, when you’re self employed, that idea of generating revenue or opportunity to generate revenue never shuts off, ever, because you’re the only source of it. Most of the time, I’m either doing something that’s making my money or I’m trying to create something that will eventually make me money. If I don’t do that for a week, I don’t get paid for a week, so there’s both sides to that, I’m not saying one is better than the other. I think that the definition of work is something that we need to think about and how we frame it. Whether you’re self employed or whether you have an employer is going to make a difference. The other three things that are kind of related, and this is getting into the sales thing. In my opinion, you have sales, scams, and charity, and they’re three versions of the same thing. Sales is the persuasion of behavior for mutual benefit, and there’s nothing inherently wrong about that. If you buy a car, the salesperson is going to make commission on thatd y, and you’re going to use the car to make money. They’re persuading you to buy a car, and there’s a mutual benefit there. Scams are the persuasion of behavior for perceived mutual benefit, so this is where someone takes advantage of someone else and convinces them it’s mutual benefit, but it’s completely one sided. That’s a scam. Charity is persuasion of behavior, but that is for collective benefits. It’s the idea that we’re all going to benefit from whatever this behavior is. The key here is that both sales, scams, and charity, the fundamental core is persuasion of behavior, and every single breathing human being has to persuade others to change their behavior daily.

Ryan  24:03  

I’m just gonna soak that in for a second. I have seen titles of books that are like, I think one is Everyone is a Salesperson or something like that. I know there have been a few of those titles out there. Have you ever read any?

Tim  24:22  

Yeah, I know what kind of book you’re talking about.

Ryan  24:25  

And I know this is true. I tell people I work with all the time who I’m mentoring in a way that a big chunk of our work is salespersonship. It’s convincing people to use tools that we think are important that are going to lead them to teach in a way that’s more consistent with our values here, but it involves sales. We have to put ideas in front of people, we have to convince them it’s worth the time to try to change the way they’re doing things, so I know that’s true, but it’s funny. I think it goes back to the money thing. Anything that feels like sales, even more than just straight up money talk, I think really, really turns off most educators.

Tim  25:20  

Oh, I know.

Ryan  25:23  

I know I put it in our notes here, but the email I sent out to like friends and former colleagues about this project, I put in this little disclaimer at the end of it saying, sorry if this sounded salesman-y or something like that. I don’t know why I did, it’s not like we’re charging for this.

Tim  25:47  

No. It’s a free podcast, a free newsletter.

Ryan  25:51  

But I think it’s so ingrained in me, like I’m so sensitive to the way that people in this profession react to sales.

Tim  26:02  

I don’t want to make light of it, Ryan, it took me years to get over that, literally years, and I don’t think it’s just limited to educators. I think for a lot of people, sales feels sleazy, and it’s really hard to climb out of that, but when you think about it, though, we’re all selling every day–the currency is what changes. If you’re trying to convince your wife to go to a certain restaurant, you’re trying to sell her on it. I think the other part that took me a long time to really internalize was that if you sell someone something for money that is going to improve their life, what’s wrong with that? That is not easy to get out. I’m not saying it’s easy to get past ten years, but I finally got to the place where selling books is tough, especially fiction, because people don’t need fiction to survive. Not on a biological level. It’s not like going to the grocery store or having to have a roof over your head. For a lot of people, entertainment is not necessary, and yet, it’s really important. It took me a long time to not be afraid to say, I wrote this thing that’s going to improve your life, and it’ll give you a few hours of escape from whatever troubles you have, and in exchange, you’re going to give me five bucks. It took me years to realize there’s nothing wrong with that.

Ryan  27:41  

Again, there it feels like a call for therapy.

Tim  27:48  

It’s not easy, man. There’s those sort of puritanical roots that are hard to get past.

Ryan  27:55  

Yeah. There was one branch of my family that made their living selling things, selling products and stuff. Back in the day, we used to have a lot of family get-togethers and picnics and stuff, and they would use some of that time as an opportunity to try to sell things to the family. I was too young to like it. It didn’t faze me at all. I didn’t think much about it, but I remember some of the adults being bothered by that, you know, feeling like we’re here just to connect.

Tim  28:37  

Context matters so much. If you’re trying to sell Tupperware to your family at Thanksgiving dinner, that’s a bit awkward. Another example that’s relevant to us and to what I do, the email list is sort of the primary tool for most online businesses and small business owners. Legally, you have to have people do what’s called opt in. If you go to teachingtransformations.com, there’s a box, and to hear from us, you put in your email address. You have to say yes, you have to raise your hand and say, I want to hear from you, here’s my email address. That’s permission marketing, so basically, then we now know, okay, we can send you stuff because you’ve said you want to hear from it. Well, it happens all the time to so many of my author friends where people will unsubscribe and say, you’re spammy. You don’t understand the definition of spammy because spammy would be me sending you emails that you didn’t sign up for, but you said you wanted this, so I think the context of where you’re selling can make all the difference in the world.

Ryan  29:47  

Yeah. I listened to a book a couple years ago by Jim Cook. He’s the guy who started the Boston Beer Company.

Tim  29:56  

Oh, yeah.

Ryan  29:57  

They make Sam Adams, and I’m a fan of Sam Adams. It was like the first good beer I had, and I think ever since then, I’ve always had at least a little in my fridge, and I like what I’ve known of that guy’s story, so I read this book. It’s actually a really good book, I really recommend it to anybody who has ever, I mean, first of all, if you like the beer and think his story might be interesting, but also, a lot of his advice about starting a company is really interesting. He says a lot of companies play company, especially in the beginning. They buy all the things that they think companies need, you know, offices and computers, and they spend money on all kinds of things like flying people to trade shows, and blah, blah, they just rack up all these expenses, but a lot of young businesses don’t have sales to back it up. He talks about the early days of starting this company where he had this beer that he loved and believed in, and he wanted to make this his life’s work to start this company. He would actually take cold samples of this beer. He made a special container to keep them cold while he walked down the sidewalk in Boston into bars and tried to get owners of these bars to give his beer a try. That’s sales, but it’s authentic sales. He believed in what he was doing, he actually left, he worked for the Boston Consulting Group, and he was like flying first class to big companies all over the world, advising CEOs and stuff about their businesses, and he left that world to start this business. I think there’s a chapter, or at least part of a chapter, about how even to this day, no one in his company flies first class anywhere. It’s just not a priority, you know? There are opportunities for sales to be honest, and I think if you feel like you have something of value or you’re building something of value, it can be really authentic, but it’s a different set of clothes for us. People that have been working in education, we’ve just never worn that set of clothes.

Tim  32:42  

Yeah, and there’s nothing wrong with that. I get it, you know, I didn’t really start to even understand it until I was five or six years into my journey and even didn’t fully embrace it until I didn’t have a paycheck anymore, so I wouldn’t expect your typical educator to be versed in sales because in the way we’re talking about it, it’s just not part of your life.

Ryan  33:12  

Do you know anyone else who left the profession, who went into a job that looked more like sales?

Tim  33:21  

Yeah, yeah, people here and there. I’ve had friends who have left education, went into more corporate structures, and came back. It’s really individualized, and I think that once you start doing it, one of the things you realize is that there are a few bad actors that really taint the whole perception. If you think about the number of companies and products and operations you deal with on a daily basis, how many of those are bad actors? Very few, but when it happens, it’s such a violation of trust that it becomes big news and headlines. But for the most part, I really believe, especially in this country, most small business owners, self-employed people, even corporations to a degree, they’re trying to do good. They really are and I think we lose sight of that too often.

Ryan  34:24  

I get bombarded with sales, and I think my irritation is just I get so much traffic in my job. I oversee technology for the school, so I get people that are trying to sell me a lot of different things, but yeah, I wouldn’t question their motives. I think they all believe in their products and services, and they’re just trying to make an honest living, and I’ve never faulted anybody for making a living in whatever way they needed to. It’s something we all have to do. It’s easy to take that for granted. When we get irritated about people who are sort of, say, pestering us with their information, ultimately, they probably believe in it, and they’re trying to feed their families, too, so I don’t think we should begrudge that, right? We kind of pushed this aside, but I want to circle back to this just because I do think that some people out there are, honestly, I’ll just take a guess here, I think probably the majority of our audience might be still planning for a conventional retirement but might be thinking about what they’re going to do when they get there, and they still want to be productive. They’re seeing that as an opportunity to do something new. There might be some people that feel a need to become a little more accelerated like you do, but again, going back to the whole thing about we all need to worry about it, I think our generation, a lot of us are going to be climbing out of that housing bubble hole and all that stuff for a while. Could you give us a sense for how your earnings compared when you left teaching? Like, did it take you a long time to kind of get back to square on that? Was it pretty immediate? What could people expect if they really tried to go all in on something, and maybe were hoping to maintain a similar sound salary level? Can you talk us through that a little bit?

Tim  37:03  

Definitely. I’m one person on one example, so people can take that for what it’s worth. Some people have done extremely well, much better than me, and other people haven’t, but I’ll just kind of share my experience. When I finished in June of 2017, I had two more paychecks coming, and that was my ramp, so I don’t consider 2017. Even though almost all of the year I was self employed or the majority of the year I was self employed, I still had W2 money coming in. I look at 2018 as my first full year, and I think ballparking it, I made about $5,000 less than I did in my last year of teaching in 2018. In 2019, I made about one and a half times what I did in my last year of teaching. This past year, in 2020, I took home about two times what I made my last year as an educator, so my profit margin has really accelerated. I’m very proud of that and happy about it. When I left teaching, we had made a mortgage and two car payments, and then we also carried about $30,000 in consumer debt that we consolidated. At one point, shortly after the financial crisis, we took all of our credit card debt, we put it into a consolidated fixed term loan, and we had about $30,000 to pay on that, and then we had a monthly balance on our primary credit card of like $10,000 to $15,000, so we were almost $50,000 in debt and consumer debt, so high interest rate debt. As of today, I’ve eliminated all of that consumer debt, so we don’t have any consumer debt leftover. That also gives you some idea of the impact that that change has had. One of the aspects of that that you don’t know until you get into it are the advantages of being self employed. You do have a self employment tax, but you also have write offs. You have expenses that give you a little bit of a tax break. I’m looking at sort of bottom line, take home pay. One of the challenging things with when people talk about revenue, especially in my area, is authors will talk about how much money they make in a year, and it’s usually gross, which is very misleading because let’s say you have an author who says, I made 200 grand in 2020. What they’re not saying is they had to spend 150 grand on Facebook ads to make that 200 grand, and then they took home 50, and that’s fine, but it’s very misleading. Whatever industry you’re in, if you’re looking at what people are doing, revenue round ups, or talking about what they made, it’s really important to dig down a little bit and see exactly what it is they’re sharing.

Ryan  40:27  

Yeah, definitely. Wow, that’s really impressive, Tim. I mean, the fact that you were able to really stay pretty even your first year out, and then the second year, you’re already making increases. That surprises me just because I would expect if I were to make a similar plunge, it would take a long time to get back to square, so I think that says a lot about. You’re very strategic. You’re good at seeing opportunities and things, we talked about that. I guess the other side, and we talked about time earlier, but are you working like 24/7? How does your time investment compare to before? You mentioned all time is potential earning time, but you could get carried away with that and kind of let it take over. I just wondered like, how’s that felt the past few years for you?

Tim  41:39  

Yeah. I’ve always had this extreme aversion to the tech bro culture, the things like always be hustling, and you’ll sleep when you’re dead. I hate that bullshit, I really do. I hate that mentality, that attitude. I had this balance that I had to create in that. I knew I had to make money or else, we’ve talked about this before, I left with very little to no savings. I had debt. My wife was not making enough to support the family. It was a huge risk, but I think that was also what drove me was this idea of like, I have no safety net, I’ve got to make this happen. Early on, other than the time I spent with my family, I was working on something. If I were to quantify that, I might say sixty, seventy-hour workweeks in that first year, which is ironically not that much different than my first year of teaching. I don’t know if you remember that vividly. It was sixty, seventy, eighty-hour weeks because you don’t know what you’re doing, and you have all that grading. It’s brutal, it’s absolutely brutal. I had a very similar experience my first year being self employed, but then you really start to understand that because you have to, like there’s no boss, there’s no manager, there’s no one directing you, and you quickly figure out what it is you can work on that’s going to result in revenue or potential revenue and what isn’t. Over the past couple years, especially now, I would say, what I consider to be “work” in air quotes is probably twenty-five to thirty hours a week at the most. That is time where I’m sitting down in front of my computer, working with clients, I’m writing, creating content, I’m doing email marketing, the very delineated work tasks. There’s probably a five to ten-hour chunk of time every week that’s blurry. Let me give you an example. By the time this airs, he’ll be on, but we have Lee Child coming on the Writer’s, Ink. podcast, and he’s got a new book coming out on how to write a mystery, so I have to read that book to prepare for the interview. Now, is that work? I guess, like I would read that book anyways, but the fact that I had to do it for an interview and for a podcast and the podcast might lead the class. You can see how you get some of those activities where it’s like, well, I might be doing this anyway, so technically, is it work? Yes or no? But to be perfectly honest, I’m working less and more strategically than I was before I became self employed, and I think this is something that’s endemic. This is a problem with the profession. I think most teachers still believe, and administrators do as well, that working harder is better, and that’s just so wrong.

Ryan  44:50  

Is better than working smarter, you mean?

Tim  44:52  

Yeah. Better than anything, right? You hear that reflected when teachers talk about kids. “Oh, he’s a hard worker.” Yeah, it doesn’t matter in this world. Maybe that mattered twenty years ago, but it doesn’t matter anymore.

Ryan  45:08  

Well, and we know what they mean is they throw hours at it.

Tim  45:11  

Right? You get back to this idea that work is time exchanged for money, so yeah, they’re worth more if they work more hours.

Ryan  45:20  

Yeah. Do you still get summers off?

Tim  45:27  


Ryan  45:27  

I’m just kidding.

Tim  45:29  

You know, my sister said to me once, what do you do for your birthday? I’m like, what I do every Wednesday. She’s like, what do you mean? Well, I’ve designed this life for myself so that by definition, I should be doing what I want to do every day. I don’t have to wait for my birthday to do that. She was like, oh, I was trying to be smug about it. I’m like, that’s just the reality. I don’t have special occasions necessarily, and the trips I do, Zach’s a great example, our Authors on a Train, I would do that with my friend. I did like that with Lindsay and Joanna for fun. Is that work?

Ryan  46:14  

Technically, and on paper it is. I was there. It was a huge amount of fun.

Tim  46:20  

Yeah, and a ton of work. Does that surprise you?

Ryan  46:27  

No, it makes total sense. People find a lot of satisfaction in their work. I think that’s a concept educators are attuned to, right? Sorry, my phone’s ringing. We’re recording this during an office day, so normally, I remember to unplug that wire. I think that’s something that’s gonna resonate with a lot of people that they’re gonna connect with, like, doing something that I love to do, and, yeah, I’m getting paid for it, but it’s not hard for me to imagine a life where all of that is sort of combined. There are things that I do that look and sound like work if I have to put a label on them, but they’re things that I enjoy doing and that I would do anyways, so that makes total sense. What’s good about your story is you’ve really designed that. You went out of your way to say, this is how I want my life to look and feel like. That’s what we’re trying to help people start to do more of is to design that lifestyle and eat again, even if it’s after conventional retirement, but you know, be creative and strategic about that. Don’t just let it happen to you.

Tim  48:21  

Yeah, totally agree. Most people start with the wrong finish line in mind. That’s the problem, like most people start with, how much money do I want to make? For me, that’s the wrong question. The question should be, what do I want to do when I wake up every day? Then figure out how much money you need to do that, and that’s a completely different approach. It sounds oversimplified, but it really is because if you don’t know what you want to do, then how are you ever going to know if you have enough? That’s when you get on that hamster wheel, and that’s when you get into trouble with debt and overconsumption and all the other problems that are hard to dig out of once you’re in them.

Tim  48:57  

Thanks for listening. Go to teaching transformations.com and get instant access to Transformations, the free weekly email with the best personally curated resources to help those in their late 40s or 50s to design a post-career life.

Transcribed by https://otter.ai


Transformations – The free weekly email with the best personally curated resources to help teachers in their late forties or fifties to design a post-academic life. – https://teachingtransformations.com/ 

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