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Home Learning Blog Master Flexible Thinking: Future-Proof Your Career Today [Show]

Master Flexible Thinking: Future-Proof Your Career Today [Show]

Master Flexible Thinking: Future-Proof Your Career Today [Show]

Demme Learning · November 7, 2025 · Leave a Comment

How do you cultivate flexible thinking and adapt to an ever-changing world, especially when pursuing a career?

In this episode, we have an insightful discussion with software engineer Dan Chimento. Having begun his career as a software engineer, he has journeyed from programming aspirations to mastering essential soft skills for business adaptability.

As AI reshapes the future of careers, Dan will share his experiences, from creatively crafting games and websites as a homeschooled student to becoming a thought leader in the financial world. This is an extraordinary conversation you won’t want to miss.



Episode Transcript



[00:00:00] Dan Cimento: You don’t have to wait until you’ve done the four-year degree and paid for the full education to get a sense of the thing you’re going to do afterwards. There is something you can find today that demonstrates what that career will look like on day one, on day 100, on day 1,000. I would encourage anybody who is eyeing a career, take the time, go on YouTube, and just google. Just search for, “What is this job like?”

[music]

[00:00:36] Gretchen Roe: Good afternoon, everyone. This is Gretchen Roe for The Demme Learning Show, and I am so excited to welcome Dan Cimento today to talk to me about future-proofing your career. Dan has done a lot of things, and I’m going to let him explain those to you. I was particularly excited to have this conversation because I feel like I’ve had the opportunity to watch him grow up. He’s got lots of things to say to you today. The most important thing, I think, is going to be, keep an open mind. Dan, welcome. It’s a pleasure to have you. Now, I’ll let you introduce yourself.

[00:01:14] Dan: Thank you, Gretchen. I appreciate it. Well, it is great to be here. My name is Dan Cimento. I am an all of the things. At a certain point, I used to be able to say what my job was and what my title was, but these days, I have bounced around so much that it’s hard to nail it down. I just like to say that I do whatever is currently in front of me. I live in Atlanta, Georgia. I homeschooled my entire education, except for one year. There was a little, like jumped out for a second, and then came right back in.

[00:02:02] Gretchen: I think that’s something I did not know about you, so I have learned something new already.

[00:02:07] Dan: There you go. My career mostly was software development, software engineering, building software products. That started when I was 12 years old. My dad, for whatever reason, thought that was probably a good career path for me. He threw some software development tools at me when I was 12 just to see what would happen. For whatever reason, it stuck. I played around a little bit, and then it just grew from there, building little games and little apps and things. Then I went to college at University of Central Florida for computer science, and then career after that, which is, again, all over the place, which we can talk about.

[00:03:03] Gretchen: When you were a teenager, could you even conceive of where you are today?

[00:03:12] Dan: Oh, no, not even close. When I was a teenager, I knew I wanted to build software and build products. That was definitely in my head. I would absolutely did say, I never want to manage people. I never want to be in charge. I never want to run things. I just want to do my job and go home at the end of the day. No, none of that has happened.

[00:03:42] Gretchen: [laughs] Well, okay. To be fair, I think when you and I talked about creating this conversation, we were talking about the suppositions we make when we’re teenagers about what life looks like in adulthood, and how we have to be open to change. Can you talk about where you started college, and now a little bit about what you’re doing? Those are two different paths. As a matter of fact, I might have said to you when we were planning this conversation, I don’t actually know anybody who is exactly specifically working in the field for which they got their degree, unless they’re some kind of professional, like a physician or a nurse, or someone in the healthcare field.

[00:04:34] Dan: Yes. No, I would say software. I might throw software into that category. For the most part, people that I’ve known who have gone to college to get either a computer science or a software development degree generally end up doing software development. That’s maybe just specifically in the last, I would say, probably 10 years, 15 years, where software has been in such high demand that if you had anything resembling a software development or computer science degree, there was an infinite number of jobs.

Employers would be fighting over you at all times. It was very easy for people who started there to just roll into that, and then that would be the career. That’s exactly how things went for me. I started off. I got an internship my senior year in college at a software development company. I think I would say I can attribute just getting that internship because, a lot of times, that can be the first thing, right? If you can just get that first thing on your résumé, the next thing, the next thing will come after that.

That first thing happened because I was able to present a résumé that had a few things on it without any professional experience. In college, a buddy of mine, who I roomed with for a little bit, had an idea for an application, like a website that was like Craigslist, but specifically for college students to trade textbooks back and forth, because that was such an expensive– You’d buy a textbook for $200 or something ridiculous, and then you’d sell it back for about $4.50 at the end of the semester.

[00:06:24] Gretchen: Right. It is the biggest scam going. I remember one of my kids had a 400-level textbook that was a new edition that we had to purchase. When that semester was over, it was a doorstop because they’d come up with another new edition, and so it was irrelevant.

[00:06:45] Dan: We had this idea. Let’s give students an opportunity to just trade textbooks. Everyone’s doing different courses, and they’re done with one. They need something else, and they swap the books. We had this idea. I had been building small games and stuff, again, since I was about 12 years old. He had this idea and pitched it to me. I thought, “Let me just try and see what’s out there.”

I googled a little bit for how to build a website and followed a couple of tutorials, and was able to put this thing up that allowed the students to trade their books. Just that one, it wasn’t a job. I didn’t have a title, but was able to put it onto a résumé and say, “I built this side project, and I used these tools and solved this problem.” That alone, that one line item was enough to get the internship.

[00:07:39] Gretchen: You know what? I think as parents, the takeaway here is that you have to practice some initiative. We can’t do it for our kids. You’ve got to be in the position of figuring out what it is that you want to do. My eldest son is a wireframe designer, but his degree is in graphic design. Through internships and experiences, he’s ended up in the position he’s in now. It looks very different from what he got his degree, although he leads a team of graphic designers. Although he’s not working in that field, he’s still managing in that field. I think that makes a tremendous amount of difference. What did that internship do for you? What was the best takeaway from that?

[00:08:32] Dan: It was confirmation for me that the degree that I got was going to be a job that I enjoyed doing. I think this is something that I’ve now learned a lot and talked to a lot of people who find themselves in a situation where they do the four years, get the degree, go into that first job that you’re supposed to get the internship or the entry-level position for that degree, and then immediately go, “I don’t enjoy this at all. This is not for me,” which is such an unfortunate and sad position to be in after doing that degree.

Again, very fortunate to say that I started that first job and went, “Yes, this is exactly what I enjoy doing,” which shouldn’t have been too much of a surprise because I had been doing similar things during college and before college to get an idea of that. It’s something that I’ve tried to encourage students to do now is you don’t have to wait until you’ve done the four-year degree and paid for the full education to get a sense of the thing you’re going to do afterwards. I think, today, there’s so much content, and that content is sometimes not super valuable.

You think about as much is on the internet today. There’s content of every shape and size, but there is something you can find today that demonstrates what that career will look like on day one, on day 100, on day 1,000. I would encourage anybody who is eyeing a career in a specific field, take the time, go on YouTube, and just google. Just search for, “What is this job like?” I guarantee, there’s someone who has videoed themselves doing the job, put it up on YouTube, just to give you a sense of like, “Is this something that I think I might enjoy doing?”

[00:10:43] Gretchen: In that way, our narcissistic society becomes to our advantage-

[00:10:48] Dan: There is an advantage, absolutely.

[00:10:48] Gretchen: -because we can at least have insight there, right?

[00:10:51] Dan: Yes.

[00:10:52] Gretchen: Would you choose again the same path if you had it to do over again?

[00:11:00] Dan: I can go either way on this one. Yes, because it went really well, and I enjoyed it. I did that specific job for 10, 12 years, and enjoyed every second of those 10 and 12 years, and grew and became an expert in my field over that time. The only reason I might have a hesitation is that computer science software development is unique in that you can do it at home on your couch. There’s a lot of jobs that you need to have the job to do, right? This is one where you could do it on your own as a hobby. I enjoy it so much that it was great to be able to go to work every day and do the thing that I enjoyed doing. At the same time, I would come home from work and do it at home because I enjoyed doing it so much.

[00:12:08] Gretchen: How does the advent of AI change what a student who has a love of computer science now create for their future? I recognize that I’m asking you a question that we don’t have all the answers to because AI is this amorphous thing that changes by the day. What do you see with the advent of AI for kids who are interested in computer science?

[00:12:40] Dan: Yes. This is a really interesting and difficult time because of the unknown. It’s exciting, and the future is exciting. This sort of technology, this sort of innovation doesn’t happen often. I think we saw–

[00:13:03] Gretchen: Right. Well, I’m excited that you chose the word “exciting” because a lot of people I speak to, particularly in the last three conferences I have attended, have used a different adjective than they have said, “scary.” It’s here. We can’t make it go away, so we’ve got to create some sort of understanding with it.

[00:13:30] Dan: I might say those are not mutually exclusive. Something can be scary and also exciting.

[00:13:36] Gretchen: True. Rollercoasters. [laughs]

[00:13:38] Dan: Yes. Anything new that you’re not familiar with is always, I think, naturally going to be a little scary, but the excitement comes with a confidence in being open to the change. I think if I was in a headspace where I let things happen around me and then reacted to them when they happened, that’s going to be a little bit more scary. Something that I think probably the most important thing I would say I learned in my career over the last decade and a half would be that openness to ride the wave as it happens versus letting it hit you. Yes, there’s some scariness in not knowing where it ends up, but it’s exciting because there’s new opportunities every single day.

[00:14:45] Gretchen: True.

[00:14:46] Dan: Especially on the AI and software development, it is a huge change. That is the role that I think is one of the first roles being the most impacted by the advent of this new technology. Before, every single line of code is written by a human being. Every month that goes by, a higher percentage of lines of code being written in the world are being written by the machine.

At this point, not for a second would I encourage any hesitation to software development. That doesn’t change at all. Software engineering, computer science, is just as exciting as it was before. The job you’re doing is a little bit different. It’s not that different. If you think about when computer programming started, it was punching holes in cards and putting them into a machine the size of a bedroom.

[00:15:56] Gretchen: You gave me hives. My senior project for my senior year of college was a box full of punch cards, this big, to run a simulation. I dropped those in the parking lot on my way to run that simulation for the last time. Yes, I can still get in touch with those feelings intimately. [laughs]

[00:16:20] Dan: Then assembly language came out, which was just a way to write the code that did that. Then on top of that came out a higher-level language like a C or a C++ or a C#, and now a JavaScript. Every time it happens, the person doing the job before is a little bit scared and uncertain about what their job is because there’s this new thing that seems like it does the job for you, but it’s just the next person is learning how to use that tool to do the job. I would say with AI today, it hasn’t changed.

I’m probably going to look back on this in 10 years and say that was a crazy thing to say. It still today, and I’m going to hypothesize for the next 10-ish years, will require a human being doing some part of it. The machine will get better and better and better. If you said that there will always be a human forever, I would say, no, there’s not always going to need to be a human. For the foreseeable future, where we’re at, there will be a human involved in the process.

The computer science will just adapt to your part to play in the development of the software is just going to change. What’s not going to change is the need to know what software are you building, and why are you building that software, and who needs it? What are their specific wants and needs, and then how can the software help them or not help them, and what tool is the right tool? There needs to be a person there. At the heart of software engineering, I would say, is a creativity, a wanting to build something new and build something fresh.

For years now, the way to do that has been writing a line of code or a couple of thousand lines of code. Now, it will be using this new tool. At the end of the day, the input is there’s a need. There’s a person who needs a thing. The output is there’s a product that solves that need. Whether you write the code yourself or you use an AI to write the code, you’re still doing that same thing. There’s still that human connection. I don’t believe that changes.

[00:18:58] Gretchen: I like what I hear you saying because what you’re saying is that human element of being able to listen and adapt and adjust in the process to see that you continue to meet the need. I have been using AI for some note-taking this week because I’ve had multiple meetings. I had the best laugh of the week so far this morning because what it thought it heard, the person I was talking would say, was something entirely different. In fact, I read it four times, going, “That is not what he said at all.”

Until we get to the point where we don’t have to check on the checkers, checking the materials, we’re still going to need that human element. That’s one of the things that I wanted to dig into a little bit, because of what you do is so much of the personal touch. What are the skill sets, beside being a confident code creator, that a young person needs to cultivate as they go through their college experience, or as they go through their certification experience because there’s more than one path to what you’re talking about? What are the soft skills they need to cultivate?

[00:20:20] Dan: It is so much more critical now. The answer to this question is so much more critical now, and I’m going to give my best shot at it.

[00:20:30] Gretchen: Well, I’m not putting you on the spot, but you do have a well-cultivated set of soft skills, so that’s why I wanted to ask you, because you’ve seen the technology evolve. Now, the technology is at a point where really what we need to do is guide the question process to know how to create what solves the problem being presented. That’s a skill in and of itself.

[00:20:59] Dan: There’s a subtle difference between just building the thing and understanding what it is that we’re building. The traditional software engineer could separate themselves from the why. It was something I would hear a lot in my career is I would talk to a software engineer who would say out loud it. It was okay to say because of the way that the jobs were separated, say, “I don’t really care why I have to do this. Just tell me what to build, and I’ll build it.”

It was an okay thing to say because it was a full job of just taking requirements and writing code to meet the requirements. Today, any job that feels like that, that is take an input and just do an action on a keyboard based on the input, I would say, and this is not to scare anybody, that specific kind of job is the kind of job that we will see start to lose. You’ll start to see the AI really take over is input–

[00:22:18] Gretchen: That’s what I’m reading in my research. That’s what people are saying.

[00:22:20] Dan: Input in and keystrokes out is exactly what large language models do. That’s what their best at is. Give me inputs and I’ll spit out keystrokes or lines of code or sentences or whatever it is. Every one of those jobs, though, has those requirements behind it. There needs to be those inputs. The adjustment, I would say, for a student who is thinking about computer science is exactly that.

It’s that small step to the left, you would say, in the pipeline where, on the far right side, the outputs are all going to be AI-generated. There still needs to be those requirements. I might say, let’s use an example of someone who’s super interested in game development. They are writing code that makes the game happen. The step to the left would be find the person who you would like to play the game and ask questions. Ask them what kind of games they like to play.

[00:23:32] Gretchen: Oh, that’s interesting. I hadn’t thought of it from that perspective. Yes, but that makes perfect sense.

[00:23:40] Dan: That will lead to probably more questions and more people. It’s something that I think a lot of engineers will do in their head. People who are lean in engineering direction, I would say, have a tendency to problem-solve. I do this myself. I problem-solve in my head all the time, and then the code would come out on the other side. There’s all the humans who need to use the thing that I built. For a long time in my career, I had a tendency to just make assumptions about what people needed because it was what I needed or what I wanted.

I built the thing that would work well for me. Taking that step to just go find the person who’s going to use it, who needs it, and talk to them and ask them questions, and don’t make assumptions about it, but ask them why they need this and what they’re going to use it for. A lot of times, the same muscles that you use to write the code, it’s just problem-solving. The problem-solving can be used to figure out what this person actually needs and what their needs are versus how to write the code that does it, and so that small step to the left.

[00:24:56] Gretchen: Sure. It also speaks to the necessity to be connected with the humans in the equation to recognize that the way AI thinks may not be the way a human thinks. Our adaptability is one of the things that AI has yet to conquer. I spoke with a gentleman this morning who is over in Singapore right now on an extended business trip.

He said the attitudes that he gets in the Far East about AI are entirely different than the attitudes that we present, which is, this looks like it might be a good idea, but what about, whereas they are instead embracing it whole cloth as, “What are the things that it can do for us? How can it make our jobs easier? How can it free up our time to think more creatively?” What I hear you saying is there’s a middle ground, where you have to reach and find the people who are thinking creatively, and then pull them into the conversation before you can really create successfully.

[00:26:16] Dan: I would say that. Obviously, always caveated by, “This is where we are today.”

[00:26:25] Gretchen: [chuckles] Yes, that is true.

[00:26:27] Dan: We don’t know what tomorrow’s version of it will be. I think that’s super important. We’re going to have this conversation today. We can talk about what the best position to hold with the AI, how to use it, and where it fits best. That will change tomorrow. This is valuable today, but I’d say the more valuable thing and the more valuable skill to try to develop is the adaptability to what will happen. Unless you’re the person in the room building the AI, which, say, a lot of computer science minds, if that’s where you’re leaning, that’s a career that will be there for– that’s probably the most– it’s where–

[00:27:27] Gretchen: It’s a stable future-proof because it’s not going to go away. [chuckles]

[00:27:32] Dan: It’s a very computer science-y mind, but if that’s where you’re leaning, there’s so much need for people who actually build the AIs. If you’re not that person in the room, the best we can do is respond to the tools that are here. I think that adaptability and the willingness to have this conversation, say, “All right, how do we use this now?” Cultivating that early, I think there’s ways to do it that are– It’s just pick any tool, anything that you want to go find, and take a second and go download it, or go to whatever the website is, and play around with it for an hour or two. Step away and then try a different tool tomorrow.

That’s like being willing and able to just jump into something with all the unknowns. You don’t know what this thing is going to be or how to use it or what the rules are, but it can’t hurt, right? You try it out and see what happens. I think that mindset is the most important thing right now, because what’s going to happen tomorrow is a new version is going to come out. Everything we’re talking about today might be obsolete. We have to be willing to just go, “All right, cool. New exciting thing. Let’s go try it out. Let’s open it up and play around with it and see what it’s good at and what it’s not good at.”

[00:28:52] Gretchen: I like the way that you said that. My kids would say that if there was one sentence I repeated ad nauseam as they were growing up, it was flexibility is a sign of intelligence. [laughs] My kids used to joke, “Mom, we’re going to carve that on your tombstone.” It now is becoming a personification that we have to be flexible in order to adapt as things change around us. You and I had a bit of that just trying to get into this webinar today, given the fact that Zoom changed their interface this morning. That was fun. As we get ready to close this conversation, first of all, what should I have asked you that I did not?

[00:29:38] Dan: I don’t have a good answer. I’m thinking I have some things that are coming to mind, but assuming all of this is everything fits into place through something like this where the answers I have are all, “Well, that’s something that somebody can go figure out on their own.” Everyone’s ability to go get an answer to something, I think, is we all so underestimate our ability. It’s this human brain ability to adapt and learn things.

I don’t have a good answer because if you have a question, if there’s a question to something, everyone who’s taking something away from this, go find the answer to that question. Go get it yourself. Very unlikely someone’s going to give it to you. We’re in a world where the tools in front of us, that’s something that they are best at, is giving an answer to a question. The answers to everything are right here. I don’t have an additional question. For anyone who did have an additional question, pull up ChatGPT, and see what it gives you.

[00:30:59] Gretchen: That is a good plan going forward. In the last question that I want to ask you, we talked about future-proofing a career. Going forward from this, if you were a young adult listening to our conversation, what would you say are the three most valuable skills, whether they’re going into software or whether they’re going into now management that you’re in or whether they’re going into product development, regardless of where they’re going, what are the three skills that you would say would be valuable for a student to invest some time in learning?

[00:31:40] Dan: Are you looking for hard or soft skills?

[00:31:43] Gretchen: Either way. I’ll take both.

[00:31:46] Dan: They’re all going to be soft skills, every single one.

[00:31:49] Gretchen: Exactly.

[00:31:52] Dan: You learn the hard skills by being good at the soft skills. The soft skills are the, I would say, get really good at knowing where you are on that curve. For every single thing that you’re learning, be like, “I’m going to learn that thing. I’m over here on the left. I haven’t even gotten bad at it yet.” Then force yourself to do it enough that you fail a bunch, and you go, “Cool. Now, I’m down here at the part where I know that I’m not good at this,” and then track your progress. We’re getting good at it.

That sort of being able to someone says, “Hey, can you do this?” Let’s be honest with ourselves and be honest with the people around us that says, “Yes, I can do it. Here’s where I am on this skill. I’m going to have to go learn it. It’s going to take me a second, but I will go learn it.” The first thing, get really good at just tracking where you are on that curve and having the confidence to know that if you do it enough, you’re going to end up on the right side of it.

Ask really good questions. I would say, actively, collect good questions. You just asked such a good question, which is, “What question have I not asked you?” I love that question. That is now in my collection of good questions. I’m going to use that probably this week if I can. “What have I not asked you?” That’s how we learn. It’s from other people, and maybe it’s from the AI. Maybe you’re asking the question to the AI. Either way, I would say actively when you’re in this situation.

I do this. The trigger for me is when I find myself wanting to say something, sometimes I’ll go, “I’m going to turn this into a question instead of a statement,” because then I’m going to learn something at the same time, versus just say something. Now, everyone around you maybe has learned something from you, but you didn’t get anything from it. Try to find a way to turn that into a good question, and you’re going to get smarter from it.

[00:33:54] Gretchen: That’s great. I love it.

[00:33:56] Dan: I have a third one. Yes, maybe those two.

[00:34:01] Gretchen: That’s awesome. Well, I knew you were going to teach me a great deal today, and I was really excited for this conversation. I want to thank you for not disappointing because it was really terrific. I want to thank our audience for joining us today. I want to thank you all for trusting us to come into your living room. Dan, thanks so much for your time. I know you’re busy. You’re on a business trip, and you still found the time to have this conversation with me. I am very grateful, and I appreciate it. Thank you so much. Please let us know how your career progresses. Somewhere down the way, I’d like to have another conversation with you. That would be awesome.

[00:34:40] Dan: Thanks, Gretchen.

[00:34:40] Gretchen: Thanks, everybody, for joining us today. We’ll look forward to coming into your living rooms again soon. Take care, everyone. Have a wonderful afternoon.

[00:34:48] Dan: Bye-bye.

[00:34:50] Voice-Over: Thanks again for joining us. We’re glad to be a part of your educational community. You can help us grow our community even more by rating, reviewing, and subscribing to the show wherever you may be hearing this. Don’t forget that you can access the show notes and watch a recording at demmelearning.com/show or on our YouTube channel. We’ll see you again next time. Until then, keep building strong foundations for lifelong learning.

[music]



Find out where you can subscribe to The Demme Learning Show on our show page.

Show Notes

Dan Chimento, a software engineer and product developer, discussed with us the evolving nature of the workplace and the crucial need for adaptability. He emphasized that in today’s rapidly changing world, the job you hold now could be significantly different in as little as two years.

Dan advocated for cultivating the ability to learn continuously. He explained that actively engaging in new learning experiences trains our brains to be more flexible, enabling us to acquire even more new skills. He encouraged learning for its own sake, acknowledging that not every experience will be immediately profitable, but until you commit to the learning process, you remain unaware of your potential.

His advice to students was to embrace being “bad” at something new before striving for mastery. This concept, known as the Dunning-Kruger Effect, highlights the journey from novice to expert. 

Get good at the soft skills, because the hard skills can be learned.

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