The Future of Work: 2024 Predictions

UC Berkeley Extension
30 min readDec 15, 2023


Jill Finlayson: Welcome to The Future of Work podcast, with UC Berkeley Extension and the EDGE in Tech Initiative at the University of California, focused on expanding diversity and gender equity in tech. EDGE in Tech is part of CITRIS, the Center for IT Research in the Interest of Society and the Banatao Institute. UC Berkeley Extension is the continuing education arm of the University of California at Berkeley.

As we look toward 2024, we’d like to take this time to remind each of our listeners that it’s important to invest in your future of work goals. So let’s call this episode the Future of Work Gift Guide. What can you give yourself to upskill? How can you help someone achieve their career goals?

To unpack and highlight insights from this past year, we’ve brought back Michelle Hector from our first episode on overcoming barriers and Barry O’Reilly from our third episode on unlearning. Michelle has a doctorate in organizational leadership and is an expert in helping people build their leadership skills, create effective teams, and expand their emotional intelligence. She started her career in finance and tech firms and now is teaching full-time about workforce development and leadership, including a course in the spring at Extension titled Effective Leadership and Management, Understanding and Influencing the Dynamics of Organizations’ Outcomes.

Barry is the author of Unlearn, Let Go of Past Successes to Achieve Extraordinary Results and co-author of the international bestseller, Lean Enterprise, How High Performance Organizations Innovate At Scale. He is an expert in entrepreneurial education for executives and co-founded Nobody Studios to launch 100 companies over the next five years.

Welcome, Barry, and welcome, Michelle.

Michelle Hector: Thank you.

Barry O’Reilly: Great to be here.

Jill Finlayson: It’s so good to see you both. I can’t believe it’s been since the first and third episodes of the podcast since we’ve had a chance to get together. Have you been very busy over this time?

Michelle Hector: Absolutely, what a year! And I can’t believe this is the last day of November. Having fun, really navigating through the chaos of 2023, and excited for the successes and what 2024 brings.

Jill Finlayson: Absolutely. And Barry, as we are about to wrap up 2023, can you say what are some of the coolest or strangest or maybe most surprising things you’ve seen happening in the world of work and upskilling this year? Was there anything that made you go wait! What? Wait! [LAUGHS]

Barry O’Reilly: Yeah, well, look, I think it’s going to be pretty hard to not talk about the use of generative AI in work and how people have been leveraging that. I think it’s just hard to get away from not talk about that. But, also, the effect it’s had at a corporate level, too, as well. Even OpenAI is just a case study in itself. So I think that will be kind of fun to talk about.

About me personally, upskilling my own self with new areas that I’ve had to develop, as I think, as we said in the show in the beginning, almost three years ago now we started this venture studio, which is trying to build 100 companies in five years. As a leader, the different skills I’ve had to learn, the uncomfortable positions I’ve had to put myself in, mistakes I’ve made, hopefully some growth I’ve had, I’m certainly happy to share a lot of the things in leadership that I guess I’ve learned about myself over the last 12 months. Some of the lessons have been hard, but hopefully, all have been fruitful.

Jill Finlayson: Yeah. I think that’s a good point. Change is never easy and getting used to being uncomfortable is one of those things that allows you to grow. Were you uncomfortable in the past year, Michele?

Michelle Hector: Yes. And really, my aha moment was experiencing, watching, and guiding people go back to work. So we went from this virtual space, and people got comfortable. And the fight from the employee, the fight from the employer, and me supporting those individuals from the employer and the employee side, it was a really — or is — just a really big challenge on how do we work with people and navigating back into the workspace. So that was, I think, my biggest aha moment, where I’ve come from a world of when the boss tells you what to do, you do it.

However, we were doing it for about 2 and 1/2 years. And so just to turn the light switch on has been interesting. And I agree with Barry. I mean, the AI thing in the educational space, just going through training and really encouraging students to use their own knowledge versus AI, and how do we get around that, and what do we do, and how do we do it. And then, in the corporate space, it’s really taking places in spaces of human capacity. So yes, it’s been an interesting 2023.

Jill Finlayson: We had an episode where we talked about where did the trust go. We were all trusting that people were doing their job when they were working from home. Suddenly, now we don’t trust them to do that? What do you think happened?

Michelle Hector: Yeah, I don’t know. Interesting enough, productivity levels during the shelter in place was really, really high. Now studies show that there’s a lack of productivity.

So I believe that we were at home working because there was nothing else to do. Now things have opened up. There’s a lot of distraction. So with that distraction, it’s much more exciting than sitting at home working. So I believe that’s the layman term.

The trust, also, you’re losing connection and collaboration and human contact, which is so, so valuable. And I believe that employers wanted to have more — I hate to use this word — control over how and what employees are doing.

Jill Finlayson: Barry, are you seeing the same thing in startups? Are people working remote? Or are they coming together again?

Barry O’Reilly: Yeah. One of the things I think we have learned is that you can never sort of replace the human, people-in-a-room moment. But it’s choosing those moments where it really matters to bring people together. Right?

So our studio, and we have people working in probably 22 different countries across North and South America, Europe, Middle East, and into Asia, everybody’s on different time zones. There’s teams that are working across multiple continents. There’s some moments where there’s concentrations of people in hubs, but, for the most part, it’s a distributed by default business.

Building startups is extremely hard, right? There’s a lot of ambiguity. Things change all the time. It’s easy for people to get misaligned and go off track when they aren’t in these intense moments together.

So some sort of big ahas for us this year especially was we had opportunities where some of our leadership team were sort of, like, doing a little bit of a world tour, right? Where they all got together in Los Angeles and London. All of the startups that were in that vicinity, we could bring them together and do really intense full-day or two-day workshops to get people really focused on what their product was going to be.

And not just personal time together, where you’re also having difficult conversations, but also sprinkled with a little bit of social and personal. We just saw the benefit that tactic offers, which was essentially like missing, not true want of missing, but just not the same experience. So that was sort of a big aha about it’s important to have those moments. We can’t just all be fully distributed, or we’re certainly never going to be all in person. So finding out where’s those really high leverage moments and points where we need to get people together was sort of a real learning for us this year.

Then for the startups’ point of view, one of the things that was a huge breakthrough for a lot of them is they went and presented their products at conferences relative to businesses that they were building. To see the energy, first of all, for the startups to focus on — one of our products is ThoughtForm. It’s a No-Code, Low-Code platform. The largest conference for that is in Paris. Once they had that as a place where they knew that they were going to go and present their product, the focus of the team to get to something to present was amazing. The chance to show their product to the world, to real customers, and get real time feedback lit them up.

They’re buzzing now with energy to keep going, to incorporate what they learned from being in person with people and seeing real reactions to their products in person. Your metrics can tell you 100 people have visited the website. But it’s different when a hundred people visit your booth and you see them use your product.

So I think it’s just we’ve learned more about the moments to leverage in-person collaboration and activities, and the benefits that they can provide, as well as what makes us very efficient that we can have teams all over the world, the talent can be part of building ventures, and it’s often excluded from it, and the benefits that provides. So it’s really just been learning, like, where do we have these interventions, what’s the leverage and outcome that they return, and then, when do we use them. That’s been a big moment for us.

Jill Finlayson: I like that intentionality around when can we best leverage bringing everyone together. That real-time feedback, of course, is phenomenal, especially for startups being able to hear from customers directly and see them interact. Just that energy that you get from being physically in the space when you’re collaborating or creating something new sounds really important. Michelle, are you seeing the same thing? Are people being more strategic about when they’re asking people to come back into the office?

Michelle Hector: Not necessarily. And I think, Barry, you have — the formula is the intentionality of when to bring people in. So the experience that I’ve had with, like I said, coaching individuals is be a push of you have to come in now. Really not understanding the life that people have created with working from home, whether that be supporting children or pets, or being comfortable, giving away cars, whatever the case may be, really lacking the human empathy for what people have created in 2 and 1/2 years by working remote. Then, the employee understanding that the business has to be ran in the particular way it needs to be run and the ask of coming back should not be a pull, versus yes, I understand and giving me time.

So I believe that the disconnect was the empathetic piece on both ends and the understanding of reality, logistics, productivity, and who runs the business. So you had people resisting to go back. You had employers strong arming people to come back and individuals eventually losing jobs because they did not respect the leader’s request. So Barry has the right formula of the intentionality of when and how and how frequent.

Jill Finlayson: And I think the best companies are going to see that and value that. Because they’re going to lose great employees if they don’t realize the potential of leveraging this hybrid workplace and allowing people to work where they’re most productive.

A couple of things I heard you both say, which is really interesting, so thinking about empathy as a skill, thinking about AI as a technology skill, if we imagine skills are like tools in a toolbox, what practical tools should people be adding to their tool belts this coming year?

Barry O’Reilly: I think you can’t get away from the fact that understanding technology is going to have a huge impact in our jobs. I’m always of the sort of belief that the technology on its own is not going to solve the answer and humans ultimately have limited capacity about what we can perform. So the magic is human plus machine.

That’s where the magic has always been. Whether it’s we developed devices to do agriculture thousands of years ago, right through to what kind of tools we’re developing to help us be more efficient now. You just have to start embracing these things. The barrier to do it, I think, is so low now that it’s really just the human sort of anxiety, maybe, or the willingness not to give it a try.

Tools like ChatGPT, you can play around with this after dinner in an afternoon for 20 minutes. It might surprise you. It might terrify you. But it will give you context about what the technology is about.

So I’m just a big advocate in don’t let your ideas or assumptions about what these tools are be dictated to you by information that you read. Go and play around with these things, experience and use them. I think that’s where people will actually get at their own informed opinions of what this thing could mean for themselves or business, how they do things, their day-to-day.

For me, it relies on being curious and putting time towards these things. So that’s just the one thing I would always encourage people, is whenever I hear ideas that are scary, that are wrong, that feel totally against everything I’m about, my first intuition is I’ve got to try this for myself, because otherwise, I’ll never know.

That would be just one piece I would just encourage people to do. When they’re hearing about a lot of these things, just go give it a try, 20 minutes, see what it’s like. Have an opinion on it. You might be surprised about it.

Jill Finlayson: Michelle, you advise a lot of people. How do you help them get over this anxiety, the fear of the unknown? How do you get them to experiment with these new technologies if they’re not comfortable with it?

Michelle Hector: The first thing that came to mind was to experience, try it, and be open to it. When we speak about AI, people are threatened by it. It is so scary, even for myself, to be honest.

Barry, I went and tried ChatGPT because the universities were, like, you got to get these students to stop using it. You have to grade around it. If they’re plagiarizing, they can get expelled from the school.

So I was, like, whoa, such a bad thing. Then, all of a sudden, I took 20 minutes after dinner and tried it myself. Now I’m, like, you have to try this.

Try it at home. It’s that commercial, don’t try this at home. I was doing the opposite, try this at home. It won’t bite. Use this to your advantage.

So really pushing people out of their comfort zone is really always my advice. Technology is here to stay. It’s going to continue to evolve. You have to stay up with it in order to be present.

The folks that I coach are executives. They want to be present. They want to be better. They want to sustain. They want to increase.

So I’m going to give it a try. And really kind of therapeutic, or having therapeutic conversations with folks that go, it will be OK. Check this out. It’s here to stay. It’s only going to become more and more a part of our lives. So really being open and trying it, it won’t hurt.

Adding one more thing to AI and technology is increased emotional intelligence. Know that you are afraid and stepping out of that comfort zone, know what your strengths and weaknesses are. My strengths are this. My weaknesses are that.

And I’ve said to folks, try AI. Maybe they can support your weaknesses. So that’s been a real big catalyst for people to say, oh, I’ll look into that. I didn’t know.

For example, people that aren’t necessarily good writers. Now you can drop something in ChatGPT and it’ll create something kind of beautiful for you. You can go back and edit that and be proud of the work.

Jill Finlayson: One of the things I like to do is go ask ChatGPT for different use cases. I’m a tax accountant. How might I collaborate with ChatGPT? I’m a doctor. How might I collaborate with ChatGPT?

The reason I like to do that is it gives you an understanding of the use cases. Not just what the technology can do, but how it can solve a real problem that you face on a day-to-day basis. Barry, what have you seen that helps people learn and take on things that may seem like a chore to them, or it may seem like I’m done with school. Why do I have to do upskilling now? How do you get them to engage with learning?

Barry O’Reilly: Charlie Munger passed away, I think, in the last week. One of my favorite quotes from him, I was actually tweeting it the other day because it just matters a lot to me. The quote was “The game is to keep learning.”

I don’t think you’re going to keep learning if you don’t like the learning process. For someone of that ilk who’s an absolute expert in their field and there’s so many nuggets of wisdom shared over the years, that’s their philosophy for life. Right? For me, it’s inspiring to think that, is that we are in constant evolution of ourselves. If we’re not open to learning new things, or if we’re not open to putting ourselves in uncomfortable positions, or if we’re not open to be part, to keep learning, and see that that’s part of loving the learning process, we’re just going to struggle. Technology is only going to accelerate exponentially about how it’s going to affect our lives

We often say in the studio that the internet was sort of a polite paradigm shift that took us 20 years to get our head around. We can all imagine our first internet experience on a 56k modem, making weird noises as we were trying to read Yahoo’s web page or whatever to the way it affects our lives now. We have multiple technology paradigm shifts all arriving together, whether it’s AI, biotech, cryptocurrencies and technologies. These are all arriving together.

So they’re going to be remixed into different recipes simultaneously and have very different sort of impacts on our lives. So if you’re not open to this idea of constantly learning, you will struggle, even in society as it evolves. So I’m just constantly trying to encourage myself and others to just take these little bite-sized experiences, as Michelle said, the 20 minutes after dinner, playing with these things for ourselves.

Try and buy one millionth of a Bitcoin. Experience what these things are. You can spend $5 to buy a tiny bit of Bitcoin and just realize how difficult that might be or how easy it was. And it’s a low stakes, hopefully low risk way of learning these things and being a participant in the system.

That’s what I really just encourage people to think about when they hear about these new things. Go try it. Just make it low stakes, low effort, but get a real taste of it.

Jill Finlayson: One of the advantages I have working at a university is I’m around a lot of students. Students are unafraid. They’re learning this at an incredibly fast pace. And they’re figuring it out, how to use it, where it can be used.

It’s a great reverse mentoring opportunity. Because they can actually say, here’s how I use it. I actually wrote the documentation and then the ChatGPT wrote the code. Or I used it to customize my resume and cover letter to match the requirements for the job description.

So it’s an arms race. They’re using AI to generate the job descriptions and screen them. And the students are using AI to better game the system and make sure that they’re seeing and making it through the filters. So we’re seeing this back and forth, which is really interesting.

But it does speak to the students are willing to learn. They’re willing to take it on and try it out. So I ask the question to both of you, maybe Michelle first, is traditional education in need of a makeover? Do we have to be doing things differently now?

Michelle Hector: Oh, absolutely. The first thing I think about with traditional education is throw away the books. We cannot rely on textbooks. They are outdated by the time they hit the consumer or even the publisher, let me say.

We have to evolve our teaching styles, the way instructors are promoted into teaching, all of the above. And I can tell you, and I’m a little biased, but students appreciate my practitioner approach to learning because what they are taught in my classroom, they can execute into real life.

We have to do more of that. I’m 49. My undergrad experience was daunting. It was reading books. It was memorizing things that I’m never going to use again.

Then I went to MBA school and absolutely loved it. I had these practitioner professors that were dot-commers. I got an MBA in 2001. They taught us how to make money, how to analyze how to make money, how to make strategic moves to make money.

I’m working in the financial industry. I totally excelled. I went back to work. I implemented things that I learned. And I was highly successful.

That’s what we need more of. That learning style was so attractive to me that I adopted so much of it as an instructor. We have to, have to, have to. These 30 year instructors that are using the books from 20 years ago, we have to stop.

The millennials are complaining about it. There’s a lot of [AUDIO OUT] with instructors, the millennials and now Gen Zs. They’re, like, are you sure that works? Or if they’re trying to implement it, that’s why Gen Z is having trouble getting into the workforce.

Jill Finlayson: That’s why I’m a big fan of entrepreneurship education. Because it’s very practitioner-based. It’s very problem solving-based. You have to create something from nothing. Barry, do we have to use that to teach in the mainstream, or are we even changing the way we teach our startup founders?

Barry O’Reilly: I really want to just resonate on a point that Michelle made. This is something I see a lot in the workforce is because these technologies are coming into the workplace so fast, to the point you made, Jill, that students embraced them naturally and are using them, so what I’m constantly seeing is that even in our startup world, right, where we’ve entrepreneurs who’ve been building businesses for many years, maybe they’re more experienced, later in their career, but you have people who are entering the workforce that are more efficient and have better ways to get work done.

Then they’re frustrated because they’re dealing with people who are not embracing these technologies. They’re technically their superiors in work. But they’re not superior in terms of their efficiency about how they execute work.

So the classic joke that probably all of us can resonate with is you’re sitting there sending your manager a PowerPoint. And they don’t know how to do anything in PowerPoint that you can do in two seconds. And they’re, like, why can this person not open a PDF? They’re the head of the company, right?

You’ve got to accelerate that to I’ve been given a research task. Go find out about what are the top five competitors in this market niche in this geography in this demographic. An experienced person will open their book and go read Wikipedia.

Or the up and coming person will start using, essentially, GPT agents to link tasks together and go start pulling all that information together. They’ll get a first raw cut of something that’s not perfect. Maybe their expertise doesn’t allow them to interrogate that information at the same level of an experienced person. But they’re coming back with something in an hour. Where the expert is, like, I need three days to do that task. Right?

So it’s a very, very different sort of style about where and how people operate. And therefore Gen Zs, or the people coming into the workforce, they’re frustrated. Because they’re actually experts in these new technologies, but they’re treated like they’re not experts yet. They’ve got to do their time.

Sure. They’ll develop their expertise in maybe the business domain. But wow, are they experts in getting information, the first cuts of information.

So it’s very fascinating to see that dynamic play out where you have these people pushing to say no, I should be given more responsibility, more recognition because I’m getting the information. And let’s just say, like, the custodians of the workforce right now are almost not recognizing the skills that these people actually have because they say you’re not an expert. I’ve been doing this for 20 years. But they have expertise in other areas. So it’s very fascinating for me at the moment.

Jill Finlayson: Well, I think it’s interesting to think about the people with years of experience who have built up an understanding of what the logic is behind the decisions that are being made, whereas somebody who’s using these technologies may not have the breakdown of how that decision was made or the factors that went into it. So one of the concerns I have is, how do we ensure that the up and coming generations that really grasp these technologies also grasp the importance of ethics and responsible innovation? How are we building that into their education? What do you think, Barry?

Barry O’Reilly: Yeah, absolutely. It’s a huge part of the process. All these things, I just feel more and more it’s like an “and.” No actor has all the information and all the insight.

Where we’ve seen magic happen is where you bring people together and they’re naturally curious about what the other side is doing. Where we’ve seen it being toxic is when there’s this sort of no, sorry, I’m the senior. You’re just the junior. You will listen to me.

Or in the opposite term, I know everything. You don’t know. You’re outdated. Information going the other way, right?

We’ve seen great, great teams, where, people are, again, everyone coming to the table from a same place and letting their expertise shine rather than see it as one side is sort of dictating to the other. It’s interesting, absolutely.

Jill Finlayson: So what does the workplace 2.0, Michelle, look like, that brings these people together?

Michelle Hector: Flat organizations are becoming more and more common. Tech has really embraced flat organizations because of that collaboration. The only way you can have wisdom is to live. Wisdom is priceless.

Add technology with the wisdom, and you have a great finished product. That is what both of you all have said. And it’s true. So having more flat organizations, and that collaboration and teamwork.

I’m a Gen-Xer. Me managing millennials was probably one of the worst facets of my career. They wanted to know the why. I asked them to do something. They said why.

I’m like, this didn’t happen in my financial background. This was the goal. This is how we need to achieve it. How would you like to do it? How do we collaborate? Let’s go.

I move into tech. I’m managing millennials. And I wanted to pull out my hair. And I went to training. That willingly learning is super, super important.

So these folks are 10 years younger than me, but they’re 10 years younger than me and they have been brought up with technology and computers. And all of a sudden, I learn that millennials need to know the why. They need to have autonomy to do things and be successful The way they want to do it and not be told.

After I did this training, it probably was a three-day, week-long training. It changed my life. My team started to respect me.

The collaboration, the teamwork, and the harmony that was built because I understood how millennials function, it was phenomenal. My most successful team was a team of millennials. And I had to do a paradigm shift. It was powerful. It was impactful.

And I still was the leader. I didn’t lose any credibility from being a leader or any power. But I learned how to coach and develop people the way they wanted to be coached and developed. It was totally different from traditionalists, from baby boomers, from Gen Xers. And now Gen Z’s, they want autonomy to do it their way, trust, and if they could do it quickly, which is great, right? We don’t need three days. We have one hour.

So just really, really working through that was powerful and impactful. I take that with me wherever I go. On top of that, I teach generations in courses, in seminars, in how do you work with the different generations. There’s four generations in the workforce right now.

Jill Finlayson: So what do companies need to teach? What kind of upskilling courses do they need to be offering? How should they be doing this? Back to you, Michelle, just because I’m trying to figure out how do we help the companies to provide the supports that they need for their workforce upskilling?

Michelle Hector: One, I mean, the easy thing was to train a company and people go through training. Really, having understanding, this is open forum. If you talk about what do baby boomers want in the workforce, it’s respect and acknowledgment that they’ve been there for 20 years.

What do Gen Z want? They want flexibility to do their job the way they want to do it, along with millennials. You have the Gen Xers saying let’s do it most efficient. Let’s create a plan.

So companies need to have understanding of who’s in their workforce and how do people — what’s their carrot for success. Once that understanding happens across the entire department, company, depending on the size, you have more cohesiveness. So you don’t have a millennial saying to a baby boomer, you don’t know how to do this, or I can do this faster.

You have a millennial saying let’s meet together and let me show you how to use AI because this will move really quickly. So there’s this respect for that knowledge. Because if you can get that knowledge of the baby boomer into AI, you have a phenomenal product.

And the millennial who’s moving the computer, the baby boomer’s providing the information, and guess what? That team has success. There’s promotion. There’s incentive. And there’s all of that. So it’s really for the company to have understandings, whatever that means. It’s AI doing research and having a meeting and really having this conversations of how do we work together.

Jill Finlayson: Barry, what would you add? What other things do companies need to be upskilling their workforce to do?

Barry O’Reilly: The things that I’m constantly thinking about even in our own business is it’s more just encouraging people this ability that it’s OK to try things. One of the best things that was given to us in the last company I worked in is that we had a training budget. It was a discretionary training budget, that we could spend it on.

It was, like, $1,000. It was great. That was an opportunity that the company gave us all to go and self-educate on something that we were interested in.

But the thing that sort of struck me every year is that we would get to this time of year, and everyone would go around going have you spent your training budget? I would say 95% of them would say no. Then what everybody used to do is to go on and start ordering books and books and books in this sort of haphazard sort of, oh, I’ve got to burn this budget type way.

Where there was always one or two people that I remember who were, like, no, I did this course. I went to a conference. Who had sort of done things throughout the year, if you will. I was, like, those are the ones. I need to start hanging out with those kids because they are getting their act together.

They are taking ownership of their professional development. They’re thinking about what do I want to learn, how do I want to do it, what are the things that there’s a good course on whatever it might be, workplace, working remotely, AI, how to give feedback to somebody. They were constantly sort of investing in themselves in areas that they wanted to grow.

So I think that’s what I would always be saying to people. Whether you have a budget or you don’t have a budget, the activity of thinking about how you want to grow as an individual and making a plan to do that, that’s what I would encourage everybody to do. There’s ways to do it, but you’ve got to be proactive about managing your learning process.

So maybe if you are thinking about something that you should be doing this time of year, whether it’s the reflection plans for next year, I would just put a couple of points down about things that you want to learn or get better at. Then tee yourself up for the opportunity to learn them throughout the year is what I would encourage.

Jill Finlayson: That is fascinating. It’s almost a health of the organization indicator. If you haven’t spent your training budget, it means you haven’t been talking with your employees about professional development.

If it’s still there at the end of the year, you’ve kind of already missed the boat. So I really appreciate that. Is there something specific you would say that you learned or sparked your interest in learning a new skill this year?

Barry O’Reilly: One of the things that, like, we’re building a startup which is building startups. It’s really hard, you know? One of the things I’ve had to remind myself is that it’s meant to be hard.

Sometimes you sort of hope it’s going to be easy. But the reality is that it’s hard. What I have found I need more of is people around me who are doing hard things and having a place to go and talk to them about the process of doing hard things.

That is probably a big breakthrough for me because I work remotely. I have the joy of my commute being a two-minute walk from where I sleep and eat to where I work, which is phenomenal. It also can be isolating, because I spend a lot of time physically on my own.

So having places to go and talk to people, whether it’s virtually or in person, about the process of doing hard things and how am I feeling, what’s working for me, what’s not, where is my head at, that has been something I have lost touch with but have reconnected with, if you will, this year. That is one thing that I’m going to invest heavily in next year, is finding groups and communities where I can spend time with people doing difficult things and share that with them and learn from them. I’ve already made two investments in that area, a conference that I’m going to go to.

Jill Finlayson: Fantastic. Michelle, what have you learned this year and what are you going to invest in next year?

Michelle Hector: What have I learned this year, really self-care and balance. Self-care is something that I truly believe in and stepped into several years ago and said, if I take care of me, then I can take care of others even better, so really scheduling out my self-care and being intentional about that.

Also, surrounding myself with people that I think, as Barry said, work as hard as I do and their achievement, trajectory, and ladder is fascinating as mine. Because when you have those support systems, and I tell students all the time, have a support system and support systems look different for different people. But really having people that will hold you accountable to greatness, to self-care, to slowing down, which is my challenge, is really, really slowing down. So having those people to hold me accountable for the good, the bad, and the ugly is priceless, so appreciating those.

The last couple of weeks I’ve spent a lot of time talking to others and reflecting on gratitude. So showing gratitude for my own accomplishments, patting myself on the back and taking a pause, and on top of that, appreciating the people around me that have to support me in all the things I do.

And so that is really, really powerful, is that taking those moments to myself, having gratitude, pausing, and I love to celebrate. So I’m going to continue to celebrate. But yes, so I think those are the things that I learned to do more of. I talk about it with others, but really taking a bit of my own advice.

Jill Finlayson: I’m glad you brought up mental health, because this has been a rough year. Between the natural disasters, the wars, there’s been just an incredible burden this year. Barry, do you have any gifts you would suggest for self-care when you’re trying to keep up with the work?

Barry O’Reilly: Yeah. Well, as Michelle is saying, celebrating is a really important thing. I think people sometimes forget that, or they feel like they can’t celebrate out loud, or with themselves, or take themselves out for dinner, or whatever they need to do. But it is a really important part of it.

Because when people are busy, they’re pushing hard. They have big aspirations. They’re trying to get to places. Maybe you have some ups and maybe you have some downs.

But there’s definitely some wins in there. And if you don’t take a moment to celebrate the wins along the way, that’s the thing that keeps you going. You know, these little micro milestones along the way where you’re, like, it’s hard, but I’m making some progress. So let’s celebrate the little bit of progress we made.

Then what’s the next thing that we’re going to go after? And it’s one thing I’m certainly trying to underline more is just remind myself that while we have a huge goal that we’re aiming for, there actually has been lots of little wins along the way and to celebrate them. Whether that’s me treating myself and going out for sushi for lunch, or having a time with friends, or time for me, doing something that I enjoy doing, where that’s been a really important part for me as well. So I would underline that one.

Jill Finlayson: So I want to obviously start thinking about the future. Because as we come to the end of the year, we also want to look forward. Do either of you have something in your crystal ball for 2024, any trends or wild guesses as to what will be the next thing in the future of work?

Michelle Hector: AI is going to be more, better, greater. With that, human collaboration is going to really, really elevate. I believe that people are going to come together to do more. So as there was this push in 2023 to please come back to work, people are going to find that as an opportunity to maintain their jobs because technology has this huge advantage.

So I believe, and it might be one, my research, and two, my joy of people and my wholesome, like, let’s get together. But with that, we can really make change, using our technology and our artificial intelligence as an asset and a contribution to our human greatness.

Jill Finlayson: And Barry, what’s your future forecast?

Barry O’Reilly: It’s an interesting one this year. You know, I think like you said, there’s been so much trauma this year inflicted upon people and especially now the pandemic that ran before that. I would just love to see maybe us all come together a little bit and have some great moments as a society, maybe to celebrate again.

Because there are some amazing things happening in the world. It’s easy to get bogged down by the differences on these things. I’m looking for a little bit of a renaissance at the moment. I think we’re due one. And I’m looking forward to hopefully having one next year.

Jill Finlayson: I am looking forward to a renaissance and having a brighter, better future. We kind of called this our skills gift guide. So closing around with that topic, what are some practical or inspiring skill gifts that you would like to give or receive this year?

Barry O’Reilly: Well, like I said, the gift I’m giving myself is investing in myself. I’m going to go to some of these conferences and masterminds, right? So that involves me getting on a plane, meeting a whole new bunch of people, going to different parts of the world.

So that is a gift for me. Because one, I’m going to dial out of the work that I’m doing, and I’m going to dial into a whole different space. So yeah, the fact that I can do that and the fact that my family’s giving me time to do that is a gift for me. And I’ll take that all day, to be honest.

Jill Finlayson: Amazing. Michelle?

Michelle Hector: I should do that, too. Yeah, good job, Barry. I’m going to go back to self-care. I believe that that is a gift that needs to keep on giving, for myself and for others, and really doing that.

Then creating that three to five year roadmap, that’s a gift that I think everyone should do for themselves. Really sit down and say, what do I want to do. And I’m going to be a little cliche and say do something you love and it doesn’t feel like work. And really having people pivot and enjoying what they do, get paid for it, time is a gift. So you might as well enjoy what you’re doing and continue to have fun, get paid, and live well.

Jill Finlayson: Any last words for folks, especially for new graduates? It’s a pretty rough job market out there. So if you’re in between jobs or you want to reboot your career in the new year, any tips?

Barry O’Reilly: Yeah. I have a massive one. It’s just find out whatever you enjoy, whatever as a side hustle. Because you know what? You could actually turn it into a job.

I think that is one of the very exciting opportunities that lies ahead for folks that are either in the earlier stage of their career or education right now. I don’t mean everybody needs to become an influencer or trying to sell t-shirts on TikTok. But there’s a real opportunity where, if you want to be entrepreneurial, if you have something that you’re passionate about, that you can actually have tools now to build and launch businesses.

Believe me. There’s nobody more employable in the market than somebody who is naturally entrepreneurial, gives stuff a try, gets stuff done. It works, it doesn’t work out, it doesn’t matter. Because companies crave having those people inside their organization because you’re going to learn a bunch more by practically trying to create a company if you want to go work inside a company. That’s what I would say.

Jill Finlayson: Thank you. Michelle, your thoughts.

Michelle Hector: I would agree. Take your talent and ask yourself, how can I make money by doing this. In addition, I am a super student. And I really appreciate these courses. And I’m plugging the Extension right now.

But I really love these courses that are entrepreneurial courses, leadership courses. What do you need to get better at to get where you want? Going back to that three to five-year plan, how can I get that knowledge to become better?

And launching my own business, so you’re developing, or you have the skill, and you can put money in your pocket, and you can have the formal learning, those two tools together is an employee that is unstoppable. And employers want that type of person, you’re a willing learner and you have the techniques and the tactics to make money. Those are the things that we need to be successful.

Jill Finlayson: I have my takeaways now. Be a super student. The game is to keep learning. Have a three to five-year roadmap. Build something. And be an unstoppable employee.

Well, thank you, both. Thank you, Michelle.

Michelle Hector: Thank you. Happy holidays to you both.

Jill Finlayson: And thank you, Barry.

Barry O’Reilly: Yeah, no. It’s always a pleasure to speak with you both. It’s so much fun. Yeah, have a great year ahead, everybody.

Jill Finlayson: And with that, I hope you enjoyed this latest in a long series of podcasts that we’ll be sending your way every month. Please share with friends and colleagues who may be interested in taking this Future of Work journey with us.

And make sure to check out to find a variety of courses to help you thrive in this new working landscape. And to see what’s coming up at EDGE in Tech, go ahead and visit

Thanks so much for listening, and we’ll be back in the new year with a look at trends and employment opportunities. The Future of Work is hosted by Jill Finlayson and produced by Sarah Benzuly and edited by Matt DiPietro.



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