Kidorable Parenting Interview

with founder of 18 Summers, Jim Sheils



Jonathan: Welcome to Kidorable Parenting’s interview with founder of The Family Board Meeting, Jim Sheils. I’m Jonathan Domsky, blogger, parenting coach, and co-founder of Kidorable. For three years now, Jim’s been inspiring and teaching me to use regular practices to connect better with my family. Let’s get started. Jim, tell me a little bit about who you are, what you do, and what you’re passionate about.

Jim: Hey, Jonathan, yeah, good to be here. Like you, I’ve been an entrepreneur for a long time. In fact, I went off into my first business venture of leaving corporate America about 20 years ago and found that whether you’re in corporate America or you are owning your own business, it can be tough to grow your career and keep balance at home. So I’ve had a real estate investment company for years.

And about seven years ago I started a business called 18 Summers which was really just a network of entrepreneur and executive families that wanted to stay connected with their families, not only be successful at work but also be successful at home. So, between my real estate deals and my speaking and consulting, with sharing the frameworks that my wife and I have created to try to simplify family life and also deepen it, it keeps me pretty busy. Plus, I have four beautiful children that I love to pieces and love to…along with my wife, be my adventure partners in the many adventures that we take.

Jonathan: What’s something that you wish you had more courage or imagination to do when you were younger?

Jim: I wish that I had had more courage to follow my passions. I was kind of taught to go into things that I had no inclination for, I had no interest in and I should’ve listened to my gut more and gone after the things that I had a natural ability for and love for. And I think that would’ve served me a lot better.

Jonathan: What’s an example?

Jim: An example was public speaking. I loved it. I was very into public speaking, very good in music and I didn’t really pursue either one. I was focused to catch up in science classes and advanced math classes, things that I really wasn’t that good at. And they seemed to just block me out from really wanting to do the things that I enjoyed because I was just burnt out. So, those would be the best examples, where it was, kind of forced myself to do things that just weren’t in my natural tendencies. I love to work hard in things that you see really good results, which I think all entrepreneurs do but I think I just got spread thin.

Jonathan: Yeah. You know, I know a lot of high school students who I feel are squandering their youth studying advanced math and…

Jim: Oh, yeah.

Jonathan: …science just so they can get into a good school, just so they can get a good job, and they’re not developing their full person. What advice do you have for families that push their kids to excel with this goal of getting into a good school, whatever that means?

Jim: Yeah. I think it’s an interesting question and I was actually with a mutual friend of ours down in the Florida Keys this past weekend. And we’ve been instrumental with sharing lessons for our families, and what we’ve decided is… Like my father was first-generation Irish, first one to go to college with a badge of honor. And it served a purpose. So my dad is also in his early 80s. And today from what I’m seeing of the change in education, the amount of people going to college now, college has actually suffered inflation. What a Masters degree is today is what just a regular four-year degree was worth probably 30 years ago. So there’s been inflationary issues there.

And I have come to the conclusion with my own family, and I know it’s kinda scary that college is an option but it’s not something that has to happen. Like with one of my sons right now, all we’re trying to do with his education is…because the old Seth Goldman question, “What is school for?” For me it’s been to unlock and support their natural talents and then also prepare them for the practical affairs of life. And most school doesn’t do that.

But the best way that I’ve been trying to do with my kids is just be very aware of what they’re passionate about and working naturally hard in and then whatever that is, just support them, dump gasoline on it and set it on fire. And that’s our friend, Baron [SP] who I know you know taught me that. He said, “Hey, if your kids just… Find out what they’re passionate about. Dump gasoline on it, set it on fire.” They go deep into those things, you don’t have to force them to work.

It’s not a big difficulty or friction like I had with things that I knew at the age of 15, I have no interest in, I’m not gonna help the world in these subjects, they’re for some people but they’re not for me. Just like the subject I was excelling in were not for some people who were in the other ones. So I’ve really tried, Jonathan, to follow that. And with my oldest son right now, he wants to be a charter fisherman and go in the entrepreneurial route of owning docks and owning his own boats but also being a very good fisherman. And you can make a very good living.

Some people go, “Oh, you’re going to let your son be a fisherman, what about Yale, what about Harvard, what about law school?” And I really don’t care about any of those things because what I want him to be able to do is support his family, enjoy his life and contribute in ways that he wants to contribute. And it’s a scary thing to give our kids a little bit of space to be able to take the passions and go deep into them. But what I’ve learned is our kids definitely…they know what they want better than what we know what they want.

Jonathan: Yeah. Jim, can you give me another example of things that you do to give children you love the courage and imagination to seize possibilities within themselves and the world?

Jim: Absolutely. Well, as you know and I think that’s how you and I originally met, I really like to get involved in family events. I like to go to events with people who are like-minded, they have similar core values. And again, being an entrepreneur, I’m kind of an entrepreneur in itself and so I like to hang out with other entrepreneur families because I think we share the same core values. And that’s one of the ways. A second way is I like to involve them. I never wanna force my kids into my business or any of the things that I do, but since I have a family consulting and event business, I let them be a part of it. I let them help run the events, I let them travel with me to do a talk. I wanna get them involved so that they’re having conversations that normally kids wouldn’t get to have.

Jonathan: Describe something in your family life that you’ve consciously made more fun, easy, meaningful, or joyous?

Jim: I think the power of rhythms, which I know you talked about right when we started the interview, has been absolutely key for me. And rhythms are just powerful, repetitive events that we go through to hold the most important space. I was taught years ago, rythmize your life around your highest and most important relationships. So just like a lot of people do that in business, I do it for home. I have some very set clear rhythms that I consistently do with my wife, with my children, with all of us together and these have really saved me from myself so that I’m not feeling depressed at the end of the year because I haven’t been consistent with my quality time. And it also gives them some time to have access and full attention from me and that’s been absolutely key. There’s a couple of again, when you hear about rhythms, that you’re setting a few home rhythms, doesn’t mean you have to have 25 or 30 of them. But if you set even 2 or 3 powerful ones, you could be 80% of the way there.

Jonathan: What would say are the two or three most important ones that you’d share for families with young children?

Jim: Absolutely. The most important one is date night with a question. Every Wednesday night, from 5:30 to 8:30, unless I’m traveling and we’ll pick another night then for the week, we have date night, my wife and I. My phone is off, her phone is off, it’s one-on-one. We love our four kids to pieces but we need our time to recharge and just be with us. That’s been one of the best ways I can be a better father and she can be a better mother. And we call it date night with a question because what we found, Jonathan, is, I don’t wanna just go out and talk about how’s the weather, what’s your favorite color, how was the kid’s day at school? I mean, those are all important things to discuss but we like to find, off of different lists, off the internet and Google, something of what is one powerful question we can ask? And what I found is by doing a date once a week, after a year you’ve answered 52 questions that you now know your spouse much better for. You’ve gone deeper with it.

So that’s one, secondly as you know with my book, “The Family Board Meeting” is about, I believe that my children and my wife are my most important investors and clients in life. So, I, just like most large businesses, I actually get with them to do a quarterly board meeting. And by doing that quarterly board meeting I spend time with them one-on-one without electronics, doing a fun activity of their day. So once a quarter, I actually spend almost a whole day with each one of my children one-on-one. And that really sets the tone for our relationship and it also is one of the ways that I’ve been able to get below the surface with my kids. And it sounds like a big commitment, but when you schedule it, it’s really not. And I love one-on-one time. When you have bigger families and busy lives, we don’t realize how much one-on-one time we lack. But one-on-one time is really the super glue that strengthens the whole family if you do it consistently with everyone.

Jonathan: And like you said, no electronics, no distractions, full focus on the other person.

Jim: Full focus on the other person.

Jonathan: Jim, what’s something about your current family life that you wish was more fun, easy, meaningful, or joyous?

Jim: It’s something that I’m already going into but wanna go deeper into. I really love, Jonathan, being involved in my kids’ education. We use a variety of Montessori, and Waldorf, and home schooling, and world schooling. And I just decided a long time ago with my values, and it’s not for everyone, every parent, I believe should have some degree of involvement in their kids’ education. I think for many generations we were taught that you should not get involved in your kids’ education because you don’t have a degree.

You just need to hand it off to a public or private school and they’ll take care of it from there. And I found that one of the best ways that I’ve been able to build a relationship with my kids is to have some level of involvement. In the subjects like my son’s fishing, I wanna help him learn, I wanna help him find things, I wanna get him new events to do that and participate in some of them.

I like fishing, not as much as him, but I found that that involvement in his education with something he cares about has inspired him to be even better and more diligent in his studies, but it’s also brought us closer together. So, my goal is always to try to figure out ways to simplify my business, simplify my life, have more adventures with my family and friends but also have space to be involved in their education. I really enjoy that part.

Jonathan: Jim, what’s something that you treasure from your childhood that you’ve tried to re-create with your own children?

Jim: That’s a great question. I think we didn’t get to do them often, but I really like adventures and vacations together. And it doesn’t have to be somewhere extravagant, but those adventures and vacations, they’re just such memory builders. You never forget them. So, I want to make sure as I have, you know, the name of my company is 18 Summers. A mentor of mine taught me that years ago, make the most of those first 18 summers, because once your kids leave the house, it’s different. They’re still your kids, they’ll still love you but take advantage of those first 18 summers before they leave to go off on their own adventures as an adult. So, I really try to… My parents, even if we didn’t have a lot of money, we did always try to have some sort of summer thing and now I try to do the same thing with my family. Take those adventures and grab hold of them. The one thing I do differently, Jonathan, is I let my kids help plan the adventures, because I think there’s more buy-in and more excitement when you do that.

Jonathan: What’s something from your childhood that you’ve consciously changed in raising your own children?

Jim: I was not the best student. I had older sisters that were very good students. I’ve always been more entrepreneurial, not really the natural route of education, I was more alternative. I care more about learning than I do about grades and whether that’s right or wrong or people think I’m crazy… There was a lot of pressure for grades on subjects that have never helped me fulfill my purpose, never helped me provide for my family. So what I’ve tried to do is be understanding. I won’t do my kids’ push-ups for them, I want them to work hard. But I really care about learning, I don’t care about grades because I think grades can sometimes be a very poor way of measuring a child’s progress.

Jonathan: What’s the best thing about being a parent?

Jim: Oh, the best thing about being a parent is the connection. I mean, to be able to be a part of someone’s life like that and have those… You know, I believe the best thing in life is the relationships we build. The relationship with ourself, with our family, with our friends and just that bond of relationship, that connection. For me, there’s nothing more important. It’s just having a chance to be a part of their life and for them to know that I’m gonna support them, I have their back, we’re gonna have adventures together and now I know, vice versa they wanna do the same for me. And there’s no better feeling of comradery than that.

Jonathan: Nice. Tell me about your current project or something else that you think I should know about your work?

Jim: Yeah, right now we’re building out a Family Rhythms Program. Because as you know, I get invited to speak at a lot of different entrepreneurial events and business organizations, and we found that this struggle to integrate business life and family life has been tough for a lot of people, but the good news with the work we’ve been doing over the last six years, some easy solutions have really floated to the top. And I’m really happy to see it with my own family, others we’ve worked with. The solution doesn’t have to be as complicated as we’ve made the problem. So, we’re creating a Family Rhythms Program that I think will help simplify family life and improve the quality of it in a short amount of time.

Jonathan: Where can I find out more?

Jim: All you have to do is go to

Jonathan: This has been such a treat. I’m grateful for your time, your wisdom, and the example that you share with me and our listeners.

Jim: Thank you very much, Jonathan, always good to chat with you.


In two weeks I’ll give a free Kidorable Umbrella to whoever leaves my favorite comment and shares this interview on the social media platform of their choice.

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