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Choosing what comes after high school can feel overwhelming—for both teens and parents. College, community college, trade school, entrepreneurship, a gap year, or jumping into the workforce: how do you help your son find the path that fits who he is without making the decision for him?
In Part 1 of this conversation, Suzy talks with Shellee Howard, founder of College Ready, about helping young people discover their strengths, find their “why,” and make thoughtful decisions about their future. They discuss the changing value and cost of college, financial literacy, exploring different career paths, and why allowing kids to make mistakes and even fail can be an important part of preparing them for independence.
Shellee Howard is the founder and CEO of College Ready, a former academic advisor, Certified Independent College Strategist, bestselling author, and speaker who has spent more than 18 years helping families navigate college admissions, scholarships, financial aid, and career planning. Through College Ready, she helps students identify the right academic, social, and financial fit while developing a strategy to pursue their goals with less debt and greater confidence. As a mother of four children who followed different educational and career paths, Shellee also brings a parent’s perspective to helping young people discover what success looks like for them.
Shellee is the author of The College Admissions Plan Simplified: A Busy Parent’s P.L.A.N. to a Debt-Free Degree (Best-seller) and How to Send Your Child to College Without Losing Your Mind or Your Money (Best-seller), which offer practical guidance for families navigating college admissions and costs. Learn more about Shellee and find college-planning resources at CollegeReadyPlan.com.
The information provided in this podcast is for general informational purposes only and does not constitute professional advice. Consult with a qualified professional for specific guidance.
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As moms, we all want our children to build happy, successful, and independent lives. But once high school begins winding down, the pressure can feel overwhelming. Should they pursue a four-year college, community college, a trade, the military, entrepreneurship, or jump straight into the workforce? How do we guide our children without making the decision for them? And how can we help them find a path that fits who they are, not who we think they should be?
Today’s guest is Shellee Howard, founder of College Ready and a former academic advisor who has spent years helping families navigate college admissions, scholarships, financial aid, and career planning. She’s also the mom of four children who each followed very different paths into adulthood, giving her a unique perspective on helping parents recognize that success isn’t one size fits all. Welcome, Shellee.
I’m really looking forward to helping parents navigate this exciting and sometimes stressful stage of raising independent young adults.
Shellee Howard: Thank you so much for having me, Suzy. I really want to give your listeners the opportunity to hear what colleges are looking for, but also just help clarify so it’s not so overwhelming.
Suzy Shaw: So, before we dive into the college planning, we’d love to hear a little bit more about you. And can you tell us about your background and what inspired you to make this career change to help families navigate this period of life?
Shellee Howard: Such a great question. So I was just filmed on Next Level CEO with Damon Johns. And he asked me the same question. And I kind of stumbled a little bit because I don’t often think about my past as it pertains to my current future.
So after that, I did some really good deep soul searching. And what I will say is I’m five generations from Southern California. That makes me unique in itself. And my whole family still is here. And I’ve been to 102 countries. And I am a big time traveler. And so I think those two things make me kind of unique. I am a mother of four; I have two boys and two girls. And why that’s important is all four have gotten into their dream school and graduated without debt, and I didn’t have a dime.
Suzy Shaw: So that’s inconceivable. Just saying.
Shellee Howard: If any of that sounds like something that’s interesting to listen to, I really encourage families; we’re going to get into some great stuff today. So I’m excited to have this conversation, Suzy.
Suzy Shaw: Well, thank you. It’s like your family came with a gold rush and you’re continuing to explore.
So you shared with me previously the story of your eldest son who attended Harvard pre-med. Congratulations. And that might have been the benchmark for your other children. So how do you navigate having multiple children with different ideas of what they want to do after high school?
Shellee Howard: So I think it’s first and foremost important to realize every child matures at a different age. My children, your children, your grandchildren, nieces and nephews. And so the big question is, when do we really start this process?
And it really started with my firstborn. He came home from middle school. So excited. He’s like, “Mom, I know exactly what I want to do after high school.” And I was like, “Whoa, whoa, whoa. You know, I was the first to go to college on both sides of our family, and I changed my major five times. So what you’re telling me is you already know.” And he’s like, “Yeah, Mom, I know.” I said, “What happened at school today?” He said, “The high school counselor came to our class and said, “We need to pick our classes.” And so I told her I wanted to be a brain surgeon and I wanted to help people. And I wanted to go to one of those Ivy things. And I said, “Sounds wonderful.” And he grabs his snack, and he walks out, and he turns around, and he goes, “Mom, will you help me?” And that was like that moment, right? When you’re like, “Wait, he just called me out.” Like, “He’s my responsibility.”
And so that’s when it really hit home. I’m like, “Wait a minute. It’s not his dream. Now it’s my responsibility to help him his dream.” And so I really took it to heart. I did go back to school, and I got my master’s degree. And then I went back to school, and I became a certified independent college consultant. And I started touring 25 colleges a semester because I did not want to let him down. And I didn’t want to pay full price. So I had two really, really big goals. One, there are no doctors in our family. So I had nobody I could even ask, “How do you do this?” And two, Harvard was $63,000 a year at that time, and I had three other kids.
So I was wearing a pretty heavy weight on my shoulders. And I will tell you that young man, firstborn, did exactly what I recommended. He never complained. He never asked why. He just did. And remember, I have three other kids, so I know that is not a common thing. I know that it was different. And so what he did is we really built his custom strategy. Getting into a college, let alone an Ivy League school, is so competitive and so expensive that I had to really think about it as I would an entrepreneur.
So I’ve started seven businesses. College Ready was my seventh. That was 18 years ago. So at 18 years, I’ve helped thousands of students navigate this process. But he was my first one. And I wasn’t as sure as I am now what colleges really were looking for. But I had a pretty good idea because college is a business. What do I do? I start businesses.
So I built him a marketing platform where he would stand out genuinely and help colleges understand the benefit of them bringing him onto their campus.
Suzy Shaw: What do you mean by marketing platform?
Shellee Howard: So think about it this way. As colleges are a business, why would they want your child at their school? Colleges are not looking for students to come sit in a classroom, get educated, and leave. That is not going to help their future business. They’re looking for leaders to run leadership opportunities. They’re looking for students who want to do activities and honors and awards. Win the Nobel Peace Prize. They’re looking for students who are going to make their school and that experience better. That’s exactly what marketing a student looks like.
So, for example, my son loved leadership, still does. He was freshman class president, sophomore class vice president, junior class president, and ASB president. Then he stepped it up, and he ran all of Southern California’s leaders. That’s what I’m talking about. I didn’t tell him he had to be a leader. I say, what do you love? “Mom, I love to support and lead other people to create the change they want to see.” Outstanding. Let’s go all in on that.
That was one example of taking something that is a gift and a talent and building upon it so colleges will see the value. Yes, he was on leadership when he got to Harvard. He ran the Key Club there. So it didn’t end. It was truly something they valued. They saw in him- think about the “Ivys.” They could have any student they want. Think about any college, truly. They can have any student they want. Why would they pick your child? What’s the benefit?
That’s what we do when we promote. We show benefit, feature, benefit, feature. Do you want it or do you not want it? And that’s what we do.
Suzy Shaw: So it reminds me of a podcast I did with a gentleman (How to Raise Boys With Purpose Who Grow into Good Men), and he was a gentleman and he was interested in sending his son to an Ivy League school and so he contacted Harvard and asked for them to send him the admissions requirements when his son was still a child. I mean, a little child and then helped guide his son through his childhood to meet the expectations of what was needed. It just feels a little bit similar to me.
Shellee Howard: Yeah, so we always tell parents this. When should you start planning for college? It’s when your child’s asking questions. What is that person doing? Why do they do that? What does it take to get into that opportunity?
So when we would travel as a family, I remember my son was in fifth grade, and we went back to visit family on the East Coast. And I said, “Why don’t we go check out MIT and Harvard?” And they’re like, “Well, why? We’re not going to college in forever.” And I said, “Well, we saw a science museum and we’ve seen an art museum. Let’s just see what this big old college has to offer.” And I’ll never forget the day we walked onto the campus, and then we walked into the freshman eating dining hall, and my son opened the door, and there was Hogwarts. It was literally straight out of a Harry Potter book. It just happened to be that my son was a huge Harry Potter fan, and all of a sudden he’s like, “How do I get here? When do I get to go? What does it take?” And he was so excited because he saw that this was not like elementary school, not like a day in the life. He was very excited, and he was the one driving, “How do I get there?”
And so I tell families it’s really about what does your child want, what is the connection, the academic fit, the social fit, and the financial fit. And then it’s just having some great intellectual conversations with them about what they want to do with their life.
Suzy Shaw: Right. Well, one of the hardest parts of parenting is knowing when to push them forward and when to step back. And so do you have any advice on what to do about that?
That balance is really tricky when you’re giving guidance. And I think location, seeing physically someplace and getting that excitement, was valuable. Were your younger kids excited about that too, or just your oldest son?
Shellee Howard: My daughter did not. She knew from the minute we walked on campus that she was not interested at all. She’s four years younger, so she was on the younger side. She just knew she wanted the big football school. She wanted the big sorority program. She wanted the big southern college experience. That’s okay. Two totally different people.
So what I like to tell parents is this: by middle school, they have established their core values, those things that are really intrinsic to them. And so to answer your question, Suzy, is how do we do this balance of parenting pushing? And as soon as the “why” becomes the students’, you don’t have to do any of that. You’re only pushing because they haven’t figured out their why. Why do they want to go to college? Why that college? Why that major? Why that career? Why do I need to do it at this timing?
Do you remember when they were three years old, Suzy, and everything was a why, why, why, why? And you’re like, Oh my gosh, no more why. Yeah. As a mom of a high schooler, I would always lean in, tell me more. Why? Why is that important to you?
Suzy Shaw: Right, that culture of curiosity, you know.
Shellee Howard: And so then it’s not pushing; it’s genuinely asking without judgment: help me understand why is that important to you? What about that got you excited? What about that university feels like something you would enjoy? And then it’s not having to push because their why is driving them forward.
Think about anything they get excited about. And they’re the ones who are like, I need soccer cleats, and I need a soccer ball, and I need this and that and when’s practice, and, you know, that whole infectious thing when they figure out, this is about me and what I want. That’s a big part of it. And if they don’t have that why, you will be pushing them and pulling them and dragging them. And that’s no fun.
Suzy Shaw: I’ve been on both ends of that why. So, you know, there are so many more options today for what somebody can do after high school, whether it’s four years or a community college or trade school, apprenticeships, military service… just going out there and doing it, entrepreneurship. So, you know, I feel like the definition of success has broadened significantly in my lifetime. So, how has the definition, do you think, changed, and what do you think parents should be talking about that they might not have considered when a generation ago, when they were going through school?
Shellee Howard: There’s a whole podcast just in that question, but I’m going to give you just the bullet point. So, the generation prior or the families of this generation, the parents, we typed our application on a typewriter, and we used whiteout. We then put it in an envelope, licked a stamp, put it on the envelope, and we just hoped it got there. Right? You just, wow, it’s on its way. And then you would wait to receive a response in your mailbox. That’s a big difference, but yet parents are treating it as if it’s the same. It’s not the same. And your child is going through very, very different challenges. It’s never been more expensive, and it’s never been more competitive.
And so, my generation, our parents told us, you will go to college. I don’t know what you’re going to major in, but you’re going to go, and we’re going to figure it out, and we’re going to take on debt because we think it’s the right thing to do. So, off our generation goes, we change our major five times, six, seven, eight, nine, ten, or never figure it out. We graduate, we look for a job, and we’re like, well, there’s no job for psychology. Well, nobody told me I had to go on and get a master’s or a PhD. I don’t even want to go to school. There was a big gap between what we thought we wanted and what really happened.
For a lot of families, the parent went to college, went in debt, and didn’t use their college degree. Now that they’re parents and they’re going, I don’t want that for my child. I don’t want them to go to school and just kind of mess around and see what happens. I don’t want them to take on debt.
Suzy Shaw: Well, the debt is much greater today than it was 20 years ago, too.
Shellee Howard: For sure, 110%. And so, why is that important? It’s a mindset shift. Because it is nothing like it was when this generation’s parents went through the process. That is the biggest shift we have to help with because these students are dealing with different struggles than we were.
Back in the day, you would pass a note in class and hope the teacher didn’t see you pass it. Now, people are videotaping them 24 hours a day. They’re watching videos. It’s a constant, in-your-face, everybody’s perfect life. So they’re already feeling, “Am I worthy? What in the world am I good at because somebody’s better than me at everything?” That’s a real struggle for this generation.
So what I do to combat it is I help them figure out who they are. And we start; it’s called See Our Future Now. We start with helping them get clarity about their financial literacy because without that piece, the whole rest of it’s in trouble. So as soon as we can help them understand how much it’s going to cost to live without their parents’ means, now they have a better idea of, “Do I need to go to New York University for $100,000 a year to be a botanist?” Probably not.
These are the things that nobody’s talking to our children about. The high school that your child’s at, there’s no financial literacy. The high school counselors have no clue how much you can or can’t afford. And now your child is making these big adult decisions with no concept of what $400,000 in debt is going to do to their future.
So we clear all of that out from the very beginning. We help them to focus, “What are your core values? What are those gifts and talents that you come with? You know those things that are easy for you. What do you advocate for? What are the things that aren’t right in this world? And what do you want to do about it?” Now we’re helping them get to know themselves. When they get to know themselves, how easy for picking a career, pick a major, and really focus in on a return on investment of that education.
Suzy Shaw: Right.
Shellee Howard: It’s a totally different strategy, a different way of looking at it.
Suzy Shaw: And it sounds to me like create a path in high school, and maybe even early in high school, like freshman year, middle school, high school, right, is to help develop that path and then be realistic about the financial ability of the family and the individual that’s going after whatever that higher education next path is going to be.
One of the things for our family was that this was an opportunity to help your children, and I feel as though what you do after high school- the decision-making part of that is one of the first steps to independence and how to make a big decision.
So what tips do you have for parents to help them understand how to coach their child through decision-making?
Shellee Howard: Oh, this is so genius. I love this one. Community service all day long. Why? Because you’re doing something for somebody else, and if you weren’t there, it wouldn’t be done. So you’re already benefiting somebody, and you find out, do I like people or do I not? Do I like animals? Do I like the environment? What is your passion, and what do you want? Has he changed in the world? And you know what?
And then allow them to fail. I know I said it out loud. That is a crazy thing for this generation. They do not want to fail.
Suzy Shaw: But I agree with you. Failing is one of the best ways they learn how to not do it again, and we let them do it when they were toddlers. You know, you’ve got to let them do it now as young adults.
Shellee Howard: And so why is that important? When they’re serving another person, they may make a mistake. But you think that person that they’re helping is going to say, “I can’t believe you blah, blah, blah.” No, they’re going to be like, “it’s okay. You know, I know your heart was in the right place.” So it’s a safe place to try things and maybe fail.
And then the other thing I want to let families know is if they don’t learn to fail and pick themselves up at home, do you really want their first failure to be in college in their first career, and they don’t know how to do it on their own? Oh, that just gave me chills. That’s the reality of what we’re setting our kids up for if we’re not letting them have big failures, not like getting run over by a bus or something, but little things like having them make an appointment to the dentist. If they don’t put it on their calendar, there’s going to be a little failure there.
And that is what’s going to teach them how to be resilient. So when they get their first B at college, they’re not going to come home and live on your couch and just be the best; they’re going to be okay and be like, you know what, I got to work a little harder. I need to stay a little bit up late or whatever that is.
I really believe that was the biggest thing that I set my son up when he went to Harvard was I allowed him to have some small failures. And they were real when he got to college, and he had to fight for every A.
Suzy Shaw: I know there’s a big cost advantage to a community college? What are the real differences financially in paths?
Shellee Howard: So important. So the first one I’ll start with is the most popular one right now, Suzy. And that’s an influencer. I have students who get on a call with me, and I ask them, so what do you want to do? And they say, I want to be an influencer. I have this many followers. Outstanding. How much money have you made? Well, I haven’t made any money, but I have a lot of likes and a lot of followers. And I go, that does not pay the bills. I need a business plan. They say, well, I don’t know how to make a business plan. Oh, that’s what you learn in college. Okay, let’s keep going.
We have the entrepreneurs of the world. They’re like, I just want to do it now. I want to just start. Let them do it now. I started my first job when I was 12. I knew I wanted to be an entrepreneur. Let them do it. Start that job. Let them go all in, and they’ll see there’s a lot more to do than just doing that thing. There’s the finance, the marketing, there’s the whole business side of it.
Then we get into trade schools. This is a very popular thing right now. And I think it’s because there’s going to be a big gap. Right? So I have students who say, I want to be an electrician. That’s outstanding. Or I want to be a plumber. Amazing. Love it. And I say, so when you are 50, do you still want to get underneath a basement? Oh, well, probably not. I mean, I watched my parents, and they probably couldn’t go under a basement. So what do you want to do at that point? Oh, well, I haven’t thought that far out. I just thought it would be a quick way for me to make money and not have to go to college. Okay. It’s one route.
I never tell them good, bad, or indifferent. I just want them to know these choices are important. As long as they have a plan, they’re golden.
Then there’s the gap year. The student says, I just need- I need some time. I need some time. I want to take a gap year. I said, Outstanding. What are you going to do during your gap year? I don’t know. The same thing I do now. Go to the beach, hang out. Oh, no, no, no. That’s not a gap year. That’s called vacation. And so if you…
Suzy Shaw: That’s a good way to get kicked out of your parents’ house.
Shellee Howard: So if you have a vacation for a year, I would like to be your parents’ child because I too would like a vacation for a year. And then I tell the parents, Stop buying groceries, stop making dinner. The vacation will end very quickly. That is all tongue in cheek. And I know conversations are real.
But then we get into what am I going to do in my future? And it comes down to the student. If a student is very much in academia and they want to be a doctor, a lawyer, a CPA, an engineer, they’ve got to go to college. There’s just no other path for them to get to that career. But what if they’re really good at a lot of things? What if they don’t even enjoy school? Maybe they enjoy making money. They’re a hustler. That’s amazing.
I was brought up by two of them, both amazing entrepreneurs who are self-made millionaires in their own. That is brilliant for them. In today’s world, that is a very hard thing to do. Back in the day, it was a little easier, but it’s still a really hard thing to do.
So now you talk to the child about financial literacy. How often do they want to buy a new car? Once a year or once every 20 years? And all of a sudden, this all comes together very quickly. They want the life that you’ve given them, but they have no idea what it costs.
Now you step into helping them understand how much electricity and gas and not in a bad way, but in a wonderful, empowering way of we want you to know this because we want you to be successful. This whole discussion changes as soon as they understand what it costs to live on their own.
Suzy Shaw: Well, I just want to say the financial literacy part is so key, I think, to child-raising (Teaching Kids Financial Literacy: Real-World Money Skills for Life). And we had a gentleman from the Money Confidence Project. It’s a non-profit as a guest. And we talked about several tools for parents to use. One was Groove, which is a little app. It teaches financial literacy and helps somebody manage goals like saving money for college, whatever those goals are. There are videos, there’s an entrepreneur, a game, an online game. I mean, all really cool stuff, free. So I want to encourage parents to check that out.
Shellee, thank you so much for sharing your experience and advice. It was such a great discussion that we didn’t want to cut a thing—so this is Part 1, with Part 2 coming next week. In Part 2, we’ll talk about how families can pay for college, including sources of money, scholarships and financial aid, plus some of the biggest mistakes families make. You can learn more about Shellee Howard and find free college-planning resources at her website CollegeReadyPlan.com. Visit the MothersofBoys.life website where we’ll share links to Shellee’s resources, website and books.
