Raising a Big Family for Success — with Craig and Jennifer Webb

Jennifer Owens/Firstly^SM
Welcome to Club Sandwich! We three have known each other for a very long time, and we're still talking! We're Pre-K friends — pre-kids. And now between us we have seven, but not equally: You guys have five; you guys went over and you were overachievers. So just a quick level-set: so, this makes us experts, right?

Jennifer Webb
Experts, wow. That’s a lot to live up to.

Firstly
Well, you know, I really do think that when it comes to budgeting and building a family that you guys are very inspirational. And you don't know this — and we would never say this out loud except to record this — but that you guys do the work that you love to do. So why don't you tell us a little bit about it. Craig, you're in the industry that paid me so well that I had to leave it: newspapers. What are you up to now? 

Craig Webb
I'm a survivor. I like to call myself the last man on the boat. I've been at the Akron Beacon Journal for 22 years now we're now part of Gannet. So I’m in my second job, but, I think, maybe my sixth newspaper chain, perhaps. [laughter] So yeah, I work at the Beacon journal, I've been an editor over the year, and a reporter, and I’m back to reporting, which is what I love. And I cover fascinating things like LeBron James, and I'm going to the Doctor Hibachi food truck, where [the chef] does all the hibachi things in the truck. So I do a lot of features. And now I also do some hard news. But Jen is kind of the one who's really pivoted in her career. 

Firstly
Yes, because Jen and I sat next to each other as reporters. And I love the way that you've taken your skills and gone into areas that you love. So tell us about what you're up to.

Jennifer
I have a degree in journalism and came out of college as a reporter and worked only about five years in that world, covering just basic hard news kind of stuff, and then had an opportunity to go and be features editor at the Catholic newspaper. We’re Catholic and that was a chance to use my skills for something that I love and felt a great passion for. And eventually, we started having a family — 

Craig
Kid after kid after kid after kid after kid…. [laughter]

Jennifer
And once we had our second daughter, I really wanted to be that stay-at-home mom. And so I was able to start a freelance career then that was able to help us pay the bills. But it was good. And just one thing led to another, and I worked for a variety of trade magazines, and eventually that kind of all faded away. But I did that for quite a while, and as that was kind of waning, Mike, the pastor at our church here said, “Hey, would you consider coming on staff part time as the communications director,” and other things, kind of a catch-all sort of position. And that's just grown and taken on a life of its own in the last seven years. I still do some freelance. But as that need has kind of disappeared, you know, things have kind of withered away — we've always operated on the cross-our-fingers-and-say-our-prayers plan, and just really trust that God provides. And yeah, one thing may go away, but something else comes in its place and we've managed to tread water, I guess!

Craig
We're on financial hospice. [laughter] 

Firstly
Well, that's my question! Well, so (a) was it always a plan to have a big family? And (b) did you have an idea of how you could — well, you know, you both chose to stay in such lucrative professions. [laughter] I mean, the way the cash rolls in at churches and newspapers! I guess the budgeting wasn't a concern. 

Jennifer
To answer your first question, about did we plan to have a large family? No, I didn't really have a real firm idea of what our lives would look like — except Craig is one of four, and I'm one of five. 

Craig
I'm also very romantic. 

Jennifer
You’ve definitely got that going there, yeah. [laughter]

So I kind of thought that we would have maybe four kids or so. But we had our first two, and they were two years apart. And it was like, “Wow! Two is good, yeah.” You've got one; I've got one. This works pretty well! 

Craig
They didn't have numbers yet.

Jennifer
And right before we knew it, we were expecting number three. And they were 12 and a half months apart, so our hands were full. And so there was quite a break there. And then after a while, I just kind of missed that little baby thing and…

Craig
And you weren't wearing your maternity clothes.

Jennifer
Yeah.

Firstly
For a hot minute. Right, exactly.

Jennifer
So then there was number four. And then along came number five. And so that's where we're at. It's all good. 

Firstly
Well, and so what has worked? So let's tell the dear listener that Craig has quite the reputation for being the bargain hunter. I'm sure you are, too, Jen. 

Jennifer
No one can hold a candle to him.

Firstly
No one can hold a candle to him. So I just I've always wondered, that he was like, “I got this. I can find a bargain that will support this entire enterprise!” 

Craig
My children have been fed on marked-down meats from grocery stores. I like to think of myself as a bottom feeder. Target hated me because I was the bottom feeder at the end caps.

Firstly
And it continues. Do you still find joy in your bargain hunting? I just referenced, someone was saying that they find joy in budgeting. And I was like, Ugh, okay, there's that. But do you find joy in your finds? 

Craig
Well, we were never — you know, you’re talking about budgets — we were never budgeters. I always felt like it was like ballast in a boat, you know? There’s just so much: you get the extra paycheck because it's a Friday, but then the wheels fall off the car or something. I always felt like God provided in a way that we had just enough that we always needed. But you can be bargain poor, too. I mean, I've always kind of been this way. I remember before we even had kids, they had Pepsi points. And we were walking through the neighborhood, in our village we lived in, and they had recycling on the curb. And I'm pulling off caps off of Pepsi bottles because you can mail them in for a beach blanket — and we still have that beach blanket, by the way. Every time I pull it out and tell the kids — they hate this story — I pull it out and say, “Do you know how many bottle caps I pulled out of garbage for this?”

Firstly
Oh, yeah. We have a TV, the only TV we have is from this promotion that the health insurance company did. That if you did these classes, they would give you dollars. And Brett and I did all of them and we gathered our pennies together and presented all these.coupons to whatever it was and got this TV. And I think about it all the time. And it's also not a great way to be healthy is to have a TV — so I don't know, I think I discounted what they were going for.

Craig
Our kids had a few Christmases where all they got was Barney things because we used Luvvs —because I think it was the cheapest diapers it didn't make them break out into hives or a diaper rash —but you had points on them. So we would save the points, and you’d get like a Barney plush doll or a Barney DVD, and our kids would have another Christmas with Barney. But you know, it got a little old. 

Firstly
You're still not doing Barney? You still don't have stuff in the attic that you're pulling out for Christmas? Guess what, kids? 

Craig
Yeah, I’m known — I just love a good bargain. And we have the places with all the Amazon and Target returns not too far from us, where I swallow my dignity and I go inside and you dig through bins. And so today we got an entire case of marshmallows for $1. Now they're close-dated, so they may be crunchy eventually, but we have a case of marshmallows.

Jennifer
We make a lot of Rice Krispie treats in this house.

Firstly
There's a role. Okay! Well, I always say that, if you go to [promotional] events and they'll give you like a swag bag sometimes — I always say, “Just because it's free doesn't mean I want it.” I don't need to take it home. I live in a very small apartment, so I cannot bring things in. I can't get the big bag of marshmallows. Because I don't have any place to put it.

Craig
We live in a fabulous state. [laughter]

Firstly
Yeah, you really do.

Craig
In suburban Cleveland. Where we have this thing called a basement? Maybe you've not heard of it? 

Firstly
No, no, tell me more. Tell me more.

Craig
We're getting better, though. I'm trying to be more restrained of what we pick up. I mean, we have kids who play travel baseball. And so it gets a point that the cheap bat from Walmart just doesn't work anymore. Our poor kids showing up to a game with the wrong shoes or whatever. We kind of had to up our game a little bit, be a little creative. And so we haunt this place, and we were able to buy our son a bat for 75 bucks that everyone else paid 300 bucks for because it was an Amazon return. We actually found our son Luke a pair of $100 cleats for $1 because they were at this goofy place. So I try to be selective and you try to buy things that make sense.

Firstly
So now let's so let's talk about the kids, because I feel like you've launched three kids into their young adulthood. Is that right to say?

Craig
Well, I would say — and I'm jumping in front of Jennifer, because she hates when I say this, but I’m going to say it anyway — I say this is my second family.

Firstly
I'm sure your sons at home love being called the second family.

Craig
And we didn’t have to get a divorce. We just did it with each other without separating our first family from our second.

Firstly
Dear listener, Jennifer is now rolling her eyes. And I can't even see her. And I know this is what's happening right now. 

Jennifer
Yes. With the disclaimer that, yeah, I’m not responsible for all the nonsense. 

Craig
But you’ve stuck with me.

Jennifer
I have. So yeah, the three kids: the oldest is 25, the second is 23, and the third is 22. And so the oldest, she’s been off on her own for a little while. She went off to college and pretty much stayed there. She's working, finishing up her master's degree. 

Craig
She fled the house, as quickly as she could.

Jennifer
She got a full time job in that town, and has been working really hard and doing a great job. She's very self-sufficient. Our second one completed college last May in the height of all this COVID crazy and had her graduation on TV and all of that. So she's kind of been treading water, trying to figure out what her best next step will be because her degree is in the arts and it's just not —

Firstly
It's a tough time for that, yeah.

Jennifer
Yeah, but the right thing will come along. She's been working hard in other jobs — 

Firstly
Yeah, that that would be her life anyways — without the added stress of pandemic life. Being a young person in the arts.

Craig
The added car has helped with transportation.

Jennifer
Oh, yeah, believe me, we have appreciated her being home and helping with the car service and all sorts of things, so I very much, I'm glad that she's here. 

Craig
And I'm not sure what our yellow lab would do without her.

Jennifer
Right. And then our third, Ryan, is in the army. College just wasn't for him. And he decided, rather on his own — 

Craig
On his eighteenth birthday — 

Jennifer
Well, it was about a week after. 

Firstly
Well, didn’t he call you while you were getting milk? 

Jennifer
Yeah, he called and said, “Yeah, I just wanted to let you know that I went and signed” and we were like, “Uh, uh…!” 

Craig
“Why don't you just get the tattoo instead?” 

Jennifer
It's really turned out to be such the right step for him. We didn't have any history of military service close in our family, so I really didn't know what that life was like, and what he had chosen. But I'm not sure he did either. But it really has worked out well for him. It's really given him a chance to really shine In all the ways that he is gifted, and I think that really has been the right thing for him. 

Firstly
So, with all of them, what were the kind of discussions that you had? And what I'm leading up to is, is it helping with the discussions you're having with your “not-second family” as they start to think about their future? 

Craig
Well, a little background: they've been kind of on their own for college, pretty much. We had some savings, a little bit. It trickles down, down, down, it gets less or less.

Firstly
Yes, I have two, and that's the case. I totally get it.

Craig
They went to private school up until — well, for the girls [it was] Catholic school through high school. Ryan wanted to go to public school for high school and his brothers will go to public school, too. But we kind of thought of it like building a house, building a good foundation on the front end, and do what we can to help on the second end. 

I think Jen put it well, when you said that they wanted them have little skin in the game. I also am an adjunct professor at Kent State, and see some students who, maybe their parents are paying for everything, and they just don’t have any skin in the game. 

Jennifer
They're not [motivated] to make it a success, because they don't have that much invested in it personally. And it's all covered for them. And I think them being responsible for their own bills at that point, really makes them focus on what do they have to do to make it work? I don't know. Maybe that’s just the way that it works for other people. But the girls, especially, have been really aggressive at finding the scholarships and the campus jobs and all the things that they needed to help pay their bills. And hopefully that gave them the incentive to make sure that they came out with a degree. Because I know lots of people who go off to college and don't, after four years or three years don't have a degree, and they've spent thousands and thousands and thousands.

Firstly
I know. It makes you heartsick. I find your daughters an inspiration. I point to them with my daughter, because my daughter would love to travel the world. And I see these kids that I know have not been given, like, “Hey, here's your blank, check, go see the world.” They've made it happen themselves. So I know it can happen. So I say that if these things are your goals, you're going to have to make it happen. Because we can help a little bit for college, but we certainly cannot give you a blank check for the world — you’re going to have to get to where you want to be. And when I see smart, lovely, talented young women in particular able to do it, I think, see, I know it can be done, because I see it being done. So kudos to you for making the lovely girls that can make it happen.

Jennifer
They really are. I think a lot of it has to do with their schooling and they really did grow into smart and responsible young women, and they make good decisions, and they really always have. But I also think that they've learned, as we have learned, that you ask for help when you need it. And there is help out there for some of these things. I know it sounds kind of corny, but God really does provide. I mean, we had Tieghan in in high school, they were going to take this trip, the music and languages department was going to take a trip over the summer to France and Spain. And it was to sing in all these places. Well, we didn't have the money to send her. We had shown some initial interest just to find out what the deal was, right? But then said, “Oh, no, no, we can't afford to do that.” And out of the blue, the head of the music department said, “Well, then we will pay for her to go because we need her on this trip.” And the only thing we paid for on that trip was her passport. They covered the entire thing because she was the strongest singer and —

Craig
Well, then we also bought her a phone that broke on the first day. 

Firstly
We could do a whole other story about the goofiness of our children, but right now we're singing their praises, but yes.

Jennifer
I just think when the time is right, and things are meant to happen, they will. And if you need help, you take it when it's offered, and you seek out the opportunities that you can, and doors open.

Craig
And it is difficult to ask for help. With my kids, it was humbling sometimes with tuition or just, you know, little things, too, really. But I also think, if you have a giver's heart, you have to have a receiver's heart too, you have to know how to accept a gift. Or just help when you need help. And thankfully, we're a little better off now, financially and otherwise. We're not rich, but yeah, having three out of the house. The other kids kind of complain: “We never had these kinds of snacks in the house! I didn’t have a car!” And I'm like, “Well, we also had five people in the house, right? And a dog and a cat.” Now we're just a dog and a cat and two kids. 

Firstly
If we look into the future, into the next chapter? What does it look like when you've launched the other two boys? Like, what is life? Travel? I mean, at that point, somehow you buy a Maserati and you become some sort of midlife crisis cliché. Love it, got it. We'll write that down. Do you guys ever think that way? We're not. We're in the midst of college and high school graduation. But I'd like to think there might be a future for something. 

Craig
I think about that, because right now, our one son is on four baseball teams, and one basketball team, and the other is on one travel baseball team, and two basketball teams. So every weekend I'm somewhere in Ohio sitting in a field or sitting in a gym. And I think, “Do you realize that in just — what? — five years this is all over?” I like to think that we will maybe have grandchildren or something, and we'll do some kind of fun. But it is a sobering thought, to think we're so busy now and that — people say, say to us, “It's a snap of a finger and it's over, you know, just enjoy it.” Although I'm still grumbling in the sun or whatever. But yeah.

Jennifer
Well, we have been on the receiving end of a lot over these years. We have been consumers of all the good stuff that's out there. And I guess I would like to think that when we have a little more time that we will be busy giving back and getting involved in things and you know, we kind of repeat that circle. 

Craig
I'm gonna take up macrame, I think it's gonna make a real comeback.

Firstly 
I think Jennifer will go off and help make the world a better place and you'll be making a macrame hanging, you know, from the ’70s.

Jennifer
I’ve always kept track of all of the money that we've received as scholarships, and all of this and give that back to the organization so it can help somebody else. 

Craig
I'll still be eating marshmallows probably from that case I bought. 

Firstly
Didn't you once find a bouncy house, too? Am I remembering that correctly? Does that still exist? 

Craig
We lived near a very dilapidated Target in an old mall and it had the best markdowns in the world because nobody dared to shop there except for me. You had to have your head on a swivel when you were going through the parking lot, but it was my favorite Target. It eventually closed but it had the greatest markdowns. Target used to mark things down 90 percent! So yes, that was my 90-percent-off bouncy house.

Firstly
Yep. That when I knew you were serious about these bargains. I was like, “You found what?”

Jennifer
I think, too, I think our kids never expected the things that their peers have. They may have wanted them. But they also knew the reality is that we don't have those kinds of incomes, and that we're not going to take the family trip to Italy, and some of these things that other people do. But they've really been good about just being grateful for what they have. And you never know what sort of random crazy stuff dad's gonna bring home.

Craig
We take exotic trips to see the world's largest cuckoo clock, you know? And Colonel Sanders' original restaurant in North Corbin Kentucky. You know, those are fascinating trips we take. 

Firstly
You guys are welcome to come back to New York and sleep on my floor, aka the guest room. 

Jennifer
We should do that. 

Firstly
You can bring the “second family” — now I'm all into this phrase, the second family. No, I’m not. They are first family, they are first in my heart, those two young men.

Well, I want to thank you guys for taking the time to share your story. You really are an inspiration, even if you maybe don't know it when you're sitting at travel baseball team games, time and time again. But you really are. So, thank you. 

Craig
You're too kind.

Firstly
So, this has been a great conversation, and I want to say to our listeners: If you're living life in the middle, share your story at editors@firstly.com, and please take a moment to rate and review our podcast. It really helps us grow. And of course if you could use a little extra financial wellness help, visit Firstly.com, created specifically with the challenges of the Sandwich Generation in mind. And let me know what you think! And until next week, I'll see you in the Club, Club Sandwich.