How To Eliminate Boredom From Your Job and Your Business

Episode 12

I thought it would be useful to look at boredom in your job from two different perspectives. The first is from the employees point of view. Why boredom occurs, and how you can create opportunities for yourself within a company to advance your career and really to make your job more interesting and fulfilling. The second perspective is from a founder and a leader and how you can create a culture within your company that engages your employees to eliminate boredom and creates a more productive team.

Thanks for listening to this episode of The Stretch Goals Podcast! We'd love to hear your thoughts on this episode and answer any questions.

Find us on Twitter @The_Scott_Davis or @RobDickersonJr


Robert: In this episode, Scott and I will be talking about as a founder, some strategies for making sure your employees are engaged, and if you’re an employee, how you can keep from being bored at your job.

Scott: This is the Stretch Goals Podcast where each week we’ll share insights and lessons learned based on our experiences as entrepreneurs. We’ll challenge you to create ambitious goals as you start and grow your business. I’m your host, Scott Davis.

Robert: And I’m Robert Dickerson. So Scott, you’ve probably seen the articles online talking about how a large percentage of employees are bored at work. Most of the articles focus on millennials, but I really think it applies to everyone since the first job was created, people have been bored at work.

Scott: Yes, definitely.

Robert: I think boredom is reflected maybe more in millennials because employees are younger. They’re just starting out in their careers and so they’re really just starting to understand the corporate world, understand what their interests are, and really, how do they create opportunities for themselves within companies. So in this episode I thought it would be useful to look at, really at boredom in your job from two different perspectives. The first is from the employees point of view. Why boredom occurs, and how you can create opportunities for yourself within a company to advance your career and really to make your job more interesting and fulfilling.

The second perspective is from a founder and a leader and how you can create a culture within your company that engages your employees to eliminate that boredom and creates more productive team. Then I think we can talk about how if you’re an employee and you’re interested, this kind of goes back to our second episode, where we’re talking about moving from a corporate job into a startup or a business of your own, how you can think about boredom, and maybe how that helps you, some skills that you learn within the corporate environment, how that helps you transition into a full time job. So just to start out, I mean, I’ve been bored out of my mind at companies before, really when I first started out. I don’t know if you’ve had the same experience.

Scott: Oh, yeah, well so here’s the thing. I had ADHD my whole life so getting bored for me is pretty easy, but I mean yeah, I would be bored if I was working on the same thing for too long or not being challenged is really the thing for me. If I felt my skillset was different than what I was being utilized for, then I got bored because it wasn’t satisfying. That gratification is what keeps you interested and makes you want to go to work every day.

I’ve definitely been there and it’s not fun, and you start having thoughts that go from the whole range of I could be making more money, to I’m better than my manager, to I can run this business myself. The fact of the matter is when you’re just starting out, you don’t have the experience to do any of that but you think you can. That’s really where you have to take a step back and say, “Look, you got to work and you got to hustle. You got to learn.” You might be able to do all these things but you’re going to learn the hard way, so learn for a little while under some other people. Yeah, you might be bored but just go be proactive.

Robert: Yeah. I think so many people don’t want to take the time to learn. They just want to jump to that next position, and think they’re kind of owed that, or they don’t need to hustle and work.

Scott: We’ve all had that thought. We all have.

Robert: Yeah.

Scott: Every single one of us.

Robert: Yeah, I agree. I’ve thought the same way but you really need to put in your time. If I look at my career, I can see how I’ve incrementally learned things that have helped me grow my own businesses. If it wasn’t for that time within the corporate world working for other people and learning, I wouldn’t be where I am today.

Scott: Yeah. We would have fallen flat on our faces. We might have eventually gotten there but we’ve learned a very, very difficult way.

Robert: I think when I was first starting out too is that I was always waiting around for my manager to tell me the next task. You’d get done the work and you’d just sit there and you’d wait and you see managers, you see all these people running around. They’re all busy. They don’t have enough time to talk to you. You mistake that for then not really caring about what you’re doing, and so you become disconnected from the organization because you’re just fulfilling your day to day jobs. For me what turned that around was I started figure out well I needed to get more engaged in what these people work on. How do get into the work that the company is really valuing? How can I make myself more valuable for the company?

You start thinking about well how can I find new opportunities really to challenge myself. You talked about the work wasn’t very challenging, but it’s taking that initiative to recognise that and go find those opportunities because not everyone does that. I think that moves over into if you’re thinking about starting your own business. I mean as a founder of your company, no one’s going to tell you what to do. You’re going to have to go out and find those opportunities. You’re going to have to grow your company. You’re going to have be … you know, show that initiative. So if you’re thinking about being an entrepreneur and you’re in a corporate job right now, use that opportunity to learn, and try out different ways to grow yourself like what things you need to work on, what things you need to learn to make that transition.

Scott: Well it’s a couple of things too. I mean obviously it’s a resume builder for you, number one. Right? You’re putting great things on your resume that can get you down the line. The other thing is you’re learning, you’re getting street smarts in the business world. You’re getting technical expertise. You’re getting all these things, and if you … Yeah, we could all do our boss’ job in some way but the reason they’re the boss is presumably because they’ve been in that position, they’ve got industry knowledge, they’ve got inside knowledge. The thing is repetition and experience, they pave the way for smarter decisions.

If you’re a little wet behind the ear going about these things, you’re not going to have some of that knowledge. So absolutely, if you’ve got the opportunity to learn, learn get those experiences but challenge yourself. Take the initiative to go learn a new skill. Maybe you’re a software developer but you want to know another language, but you don’t have a lot of work going on because you finished all your tasks, well go learn another language in your spare time. You know like challenge yourself.

Robert: I think there’s so many areas within a company that the company values. You need to find those areas for yourself by talking to people within the company. I think that could be getting more customers, doing better customer support, increasing revenue for the company. Adding innovation into the product development. There’s so many areas that companies find valuable. You need to figure out what those are, and then figure out how you can use your skill set to help that. That might mean developing new skills, but you need to figure out what that value is for the company so that you can align yourself with that value, so you’re not just sitting there bored, waiting for someone to give you the next task.

Scott: Yeah. The only problem is that if you’re bored, you’re just phoning it in basically. You’re maybe not engaged in the company, so it’s your job and you’ve got to get engaged somehow, make it interesting for yourself. Obviously, you started working there for a reason. Hopefully, it’s not because you wanted a paycheck but it was because you were interested in what you were doing. If that’s the case, find that again and get re-engaged, find some new aspect of the business that you haven’t previously learned, and try to apply that to what you’re doing.

Robert: You talked about in a previous episode how you grabbed a Mac that was sitting around, and started developing apps in order to help the company. Right?

Scott: I did.

Robert: That became a profit center, a new product for the company. You were learning new skills and you were growing with that. That shows initiative. That’s something you have to do as an entrepreneur to grow your company. So I think that’s a really good example.

Scott: Yeah. When I was 18 or 19, I was working for the Department of Defense. I was rarely challenged there. I’d get my tasks done so quickly that my supervisor would often be like, “Dude, you’ve got to slow down,” because they didn’t have enough for me to do. Well, I played on a softball team for the Department. I decided to start learning database programming by making a database, and keeping track of all the statistics, and wrote a little app that you could switch and view player cards, and see how many home runs, and what their average was, and all that stuff.

I took something that was interesting to me, which was statistics and sports, and I applied it to a technical skill set that I needed. I wasn’t wasting my time. What was cool about it is I showed that to my supervisor who was also on the softball team. He immediately knew that I could be doing more with my skillset. My next project that I got was all about database programming. I took my initiatives and my interests, and I applied to things that were related, and it ended working out for me. So the thing with the Mac like you mentioned, obviously I’ve been doing IOS apps for a long time now. That wouldn’t be the case had I not taken that initiative.

Robert: Yeah. I started at one of the companies that I worked, I started getting involved with really seeking out mentors, and people that were into business development. I really like to architect new products, and think about new ideas. I would align myself with people that were going out there thinking about these innovative ideas. I got an opportunity to just brainstorm, and prototype different things that they could pitch to customers. That was a perfect opportunity for my skillset. Those weren’t just given to me, I had to go find those people. I had to interact with those people, and show that I had some initiative to do that. So I think that’s really important that you find opportunities within the company, and really show that initiative. Sometimes you just need to get a new job. Right?

Scott: Yeah.

Robert: Not every job is the perfect job, but try to make the most of it. You can, and learn new skills.

Scott: So for awhile you were a hardware guy, right?

Robert: Yeah.

Scott: So that’s accurate, right?

Robert: Yes.

Scott: So for you in that scenario you can’t just steal a circuit board and start wiring up a bunch of stuff that’s company property. It’s like what did you do when you were there and you were bored?

Robert: Well you can get development boards, a couple hundred bucks. So I’d go to people with an idea, and say, “Hey, it’s going to cost me a couple hundred bucks to get these development kits. Let me prototype it before we go spend a bunch of money and actually develop a product.” You can do a proof of concept like we were talking in the episode nine about product demos. You can show that concept and then just take it from there. Once you get customer buy in, and once you get it out there, people are more willing to invest money in your ideas to develop them.

You’re right, you can’t just … It’s hard to go out on your own and just start doing that, especially if you need resources to build things. A lot of times you can find ways around that, cheaper ways that people are willing to …

Scott: Or you can ask.

Robert: Yeah.

Scott: Like I said, I asked about the Mac. I was like, “Are you guys going to use this thing.” They
were like, “No.” So guess what? It’s mine now.

Robert: Yeah. At one of my last jobs they … an idea that we were developing within the company ended up to be multi-year project. It was small project just like I was saying, I spend a couple weeks putting it together, and it ended up being a multi-year project. So you really never know how things are going to turn out when you take that initiative to drive things forward. Let’s talk about this is about kind of as an employee, but let’s talk about as a founder. That’s really what our podcast is about, is about growing your business and being a leader, being a founder. If you have these people on your team, how do you keep them from being bored? How do you keep them engaged, and what are some reasons why the employees become bored?

I think it’s important that I’ve seen it a lot when people start to become micro managed. Where they’re given these small tasks, and not provided a high level context of what is the goal we’re trying to accomplish. It’s more of complete this little task and then I’ll get back to you with the next task. You were saying for yourself, you were able to complete those things quickly and then you were sitting around waiting because at that point your manager becomes the blocker to give you the next thing that you need to do. I think it’s important as the founder to think about how do I provide the context, and the goals, and the milestones for the employees and the team such that I’m not going to be in the way, that they’re just going to be able to take it and run with it.

Scott: Yeah. I think in my experience as a manager and founder, you really have to know your team. Every person’s different, get to know them, get to know what makes them interested in what they’re doing. You can sense passion. If you’ve got a developer who’s a greenhorn who just wants to write everything, take some time to get to know them, and find out what they’re really interested in. It applies to any industry, not just to software but get to know your people, find out what’s interesting to them. Then listen to what they’re saying.

If they’re working on a task for you, whether it’s software, or it’s an accountant, they’re going to come to you and talk about the work that they’re doing. During the course of that they might make recommendations or say, “Hey, there’s this thing out there I thought about looking at or using.” That’s in a subtle way, them telling you that’s something they’d like to explore. Probably because it’s interesting to them, or maybe because it also benefits the company.

My point there is listen to those pieces of feedback because at some point they’re going to not have something to do on a Friday afternoon, and you’re not going to give them something because it’s Friday, right before Christmas or something. You ought to say, “Hey, you know that thing you mentioned two weeks ago? Why don’t you go ahead and play around with that.” Give them that opportunity because they mentioned it, they’re interested about it. Then also allow them to explore a little bit. Say, “Hey, we’ve got this new feature that we’re doing on this new product, and we want a couple of ideas.”

Give them the opportunity to go out and research as well. It allows you to still feel creative, and feel like you’re still a part of the process. You have to involve them in the company, and make them feel wanted and needed like they have an impact. It’s when you get to the point that you don’t feel like you can impact a company, that you start becoming bored or disconnected. Those signs are very, very basic. You don’t care. They’re not as passionate. So just keep an eye out for those things.

Robert: How do you let people explore their creativity when you have all these deadlines coming up? I think that becomes hard, especially when you constantly have things you need to get done. You have deadlines, and you have customer deadlines. How do you balance that within your organization to let people explore that creativity while still meeting customer deadlines?

Scott: You know sometimes it’s not even necessarily about whether you have the time. If you can acknowledge the fact that they’re saying they are interested in these things. If you can say, “You know what Rob, I hear you. I’m going to write that down. I’m going to put it in our backlog. I’m going to put it in your career goals.” But if you say, “Hey, I am acknowledging what you’re saying. It’s important to me that you eventually get to explore that. Let’s finish up these deadlines. Then I promise I’ll find a way to sneak it in.” That’s better than going, “No, we can’t do it right now.” As a person you hear that and you have no context as to why, but if you give them something that’s like, “I can’t do it right now, but here’s what we’re going to do, we’re going to try and fit it in.” That’s a better approach.

To go back to your original question, how do you fit it in. Well you obviously have to weigh company objectives and things like that, and timelines, and make sure that it can fit in. It’s not always going to, but you could do something like once a month have a half day on a Friday. They’re typically called cake and beer days where everyone has either a beer or a slice of cake, and you just go work on something fun. It keeps people relaxed and loosened up. You could afford half an hour a month to give your employees some time to explore a little bit.

Robert: You’ll have to let me know when that cake and beer day is, I want to come to that.

Scott: Just as long as it’s not beer flavored cake, that would be nasty.

Robert: I think what you said is really good. I think acknowledging and attributing that to say hey we’re going to do this at the right time is really important. I think that’s a really good way to do it. I think that communication is really where things breakdown as you’re communicate … you know where you have a team. I see it everywhere. It’s in big companies, it’s in small companies. It’s that communication of how we’re going to operate, what the expectations are, and if you can do better at communicating what your plan and your vision are and how you fit these things in.

I think another thing to what you’re saying too is that in the normal course of doing their work, you can allow this creativity to sink in. Instead of telling them exactly how to do something, you give them that flexibility. I think you touched on that a little bit.

Scott: Yeah. I mean you just have to say these are the expectations for completion. What are your acceptance criteria for this task or this product? They can figure it out themselves. Presumably you hired them because you trust them in some way, so let them do their job. Let them have some creativity. Like you said earlier in this episode, you can’t micro manage people. Number one you’re going to remove their own sense of personal satisfaction, and you’re going to remove their drive. Then they’re going to resent you, and you don’t want that.

Robert: Yeah. I think that’s a really good point. You want them to do their best. You want them to achieve what the company values. It think it’s important to put that out there too as to what do you value within your company as well, so they can achieve that.

Scott: Right. There’s also just to touch on what I’ve just said about acknowledging that you’ve heard them, and say that you’re going to give them the opportunity. Lip service is bad. Don’t just tell them that every time. You actually need to try give them the opportunity. Sometimes you can’t focus strictly on what business objectives are. You’ve got to work life balance. People’s creativity is part of both. It’s not just something you do in your spare time. It also is important to the business. Like you said earlier, your exploration turned into a two year project. I mean those types of things don’t happen if you don’t give somebody the flexibility to explore new opportunities.

Robert: How do you get that feedback from employees that they’re bored? Because I find a lot of times employees don’t want to tell the founder, the manager. They keep that information from them. They might tell their peers that they’re bored, but they won’t come up to you and say, “Hey, I’m bored.” How do you open that dialog between them to get people to be more upfront with what they’re doing with you? I think maybe it goes back to what you’re saying that establish that relationship, that communication channel to

Scott: Yeah, it does. Well the thing is typically in a corporate world things are more structured and more rigid. When happens is you tend to have this condescending sort of attitude as you go further down the food chain. When that happens you don’t have trust. If you’re being condescending towards me, I’m not going to tell you anything. I’m going to be very protective because this is typical psychology. If you’re being aggressive towards me, I’m going to either be aggressive back, or retreat. Since you don’t want to lose your job, you retreat a little bit, so establish a relationship. I’m not saying you have to be best friends, but I’m saying know your people as a founder of a company. Even as a manager in the startup space you’ve got to be able to relate to people.

If they can’t talk to you in the startup world, you’re doing something wrong. We live and die on being flexible, and creative, and adaptable. We need everybody’s feedback. We don’t have a thousand employees in our company. We need to hear what everybody’s saying. Just treat them as part of the family, the company family.

Robert: Yeah. You can’t afford to have people who are bored in a startup.

Scott: No.

Robert: I mean everyone has to engage because everyone is so critical to the success of that business because it’s so small.

Scott: Yeah. If you talk to them in a normal human way, just like we’re talking right now, and say, “Hey, what’s going on? You seem a little down lately,” or “Hey, man read any good tech articles lately? What’s going on in the space? Is there anything we can do to improve?” If you ask them an honest question, or even if it’s not something you necessarily care about. Let’s say it’s a crafted question because you know that they’re a little down. The point is as long as it’s delivered in a good way, they’re going to respond, and you’re going to get information from it. Okay, he’s bored because of this, or whatever. The thing is it shows that you care when you ask questions. That’s really all that matters. People want to know that they’re needed.

Robert: Yeah. I think that’s a really good point. I think this has been a really interesting conversation because I think it bridges the gap between a corporate job and being bored there. Then seeing how boredom impacts a startup, and you as a founder have to figure out how to reduce that, and make everyone engaged. I think it’s really good that we’ve talked about that. Let’s talk a little bit about … to kind of finish up this episode, if you’re an employee and you’re bored and you want to start a company. What are the expectations of I guess, making that transition when you move over to a company full time? You’re not going to be bored. I mean I’m not bored anytime. I always have too much work to do. That might be the same for you as well. I don’t see how I could ever be bored. It’s kind of this …

Scott: Yeah, well maybe for some people that’s the answer. Some people need constant engagement.

Robert: Right. I think that’s important to point that out because it’s this kind of I guess, this totally different worlds where in a corporate job you’re expecting someone to hand you tasks. Maybe some days you are bored, and you like that, whereas I feel like in a startup it’s constant. There’s always something to do. There’s always ways to push forward, and so you’re never going to be bored. You’re always going to have too much work to do.

Scott: Sure. I refer to the generational differences. I refer to a group of people as the trophy generation. What I mean by that is you show up and you expect to get a trophy just for playing. No, that doesn’t flow for me. I didn’t get a trophy unless I was in first place, or got MVP, period. You don’t just show up to work and get a promotion every day. It doesn’t happen. If you have that in your mind that it’s going to happen, you need to shift industries. The point is you have to work. You have show creativity and benefits to the company in order to go up the food chain, especially in the corporate world.

In a startup space, you still have to work. You can’t just go, “I’m going to make an app and it’s going to get a million dollars. I’m not even going to market it.” Does that happen? Very rarely, so you still have to work. You don’t just show up, put an app in the app store, and get a million downloads.

Robert: But that’s not what all the articles tell me online.

Scott: Then you’re part of the trophy generation Rob too.

Robert: No, I think that’s an important point to make. That there’s a lot of feel good stories out there of I worked three … overnight and then had an app that had a million downloads. That is really not the case. A lot of times these people that you see have successful companies, it may seem like it was an overnight success, but they were working 15 years grinding. I know we talked about Nike. That was the same way. That was an eye opener for me reading Shoe Dog, just how long he worked. He had a separate job growing Nike. I mean it wasn’t just a magical just happened.

Scott: Even those cases though of the hey I released an app, and I got 10 million downloads, they do happen, they absolutely do. They’re very rare. The point is they released it on the right day, maybe it was by chance, or maybe they thought about it. Certain days app store releases are better. For example, if you can get an app in before the Christmas break, when Apple doesn’t review any apps, you’re asking to stay at the top of the charts because there’s no new apps coming out, so there’s a tactic for you. Write that one down. My point is that there’s still pieces that made those apps successful that is more than just putting an app out there. There’s some marketing, or some tactics, or growth acting, or what have you. The point is you didn’t show up and play left field and go O for 87 on the season, and get a trophy. You showed up and you tried to win the game for your team.

Robert: Yep. Got to get out there and hustle.

Scott: That’s right. That’s the end of my baseball rant.

Robert: So let’s wrap it up. I think we’ve talked about in this episode some strategies for reducing boredom I guess. If you think about it as a leader, as a founder of your company, what you can do to engage your employees, your team, communicate better with them, create ownership. You want a team that performs the best that they can. If you’re working in a corporate job right now and you’re bored, find opportunities to challenge yourself, to learn new skills. Even if you’re thinking about eventually starting your own business, figure out what areas you can learn, and you can grow, and take those skills and apply them to your business. Use it as if it’s a personal learning opportunity, maybe that’s all it is, or take initiative. Hustle, and I guarantee you won’t be bored. If you start a company, you’re not going to be bored either.

Scott: Yeah. And ask for a trophy, it helps.

Robert: We’ll send you a trophy. All right, until next week.

Scott: Thanks guys, see you.

Robert: See you.

Robert: Thanks for listening to this episode to the Stretch Goals Podcast. You can access the show notes for this episode and listen to other episodes by heading over to

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Robert Dickerson


Robert Dickerson is the Founder and CEO of Mapout a mobile learning platform that uses video courses to educate customers and train employees. He helps companies develop and launch their products.

Scott Davis


Scott Davis is the Founder and CEO of MobX, a mobile development software agency. He has 20 years of experience developing software for Government, Finance, Sports and the Telecommunications industry.