“When people lose the fun, they stop growing”
Collin Cummings, founder of PlayWell, talks about play, fun and how we can design better work experiences.
Collin! I’ve heard so many great things about you and I really admire what PlayWell is doing so it’s great to finally meet. What’s your backstory?
Well, I started studying political science in college but it wasn’t really my thing. I get very frustrated in environments where someone tells me the method I need to use and where I feel I have a lot of value and input but I’m not allowed to exercise that. It feels like a waste of my time. So I dropped out and started a couple of businesses getting experience. After doing that, I went back to school to study design and I think that worked out because design education is self-administered. At least it was at the school I went to. So we studied what makes design great, but when it came time to our projects we were self-managed and they held us accountable for our success.
So you like running your own show?
Yeah but that’s just my personality. I perform better when I’m not in a big organization, stuck between systems and barriers to getting good work done. That situation has always bothered me and made me feel like I was wasting my time. Big companies can be so bloated and want you to navigate their specific systems. I think that’s why I like being in a startup. Everyone is scrappy and working to make things happen. Nobody is wasting time because you don’t have time to waste.
So what is your startup PlayWell about?
Fundamentally, PlayWell is about education on game creation and taking that knowledge into product and organization design. Some people come to learn how to make games on a technical level whereas others might sign up for something like a a world building class learning how to tell non-linear stories. Courses like that are important because how we think about stories in games is completely unique to the medium. Consequently, There’s a lot to teach and we’ve learned that those game concepts are equally applicable to products and startups.
We’re now spreading the knowledge on why every product, organization and group should be thinking about play as a driving force behind what they do. Creative play helps people get out of their comfort zones. It facilitates fearless interaction where we might otherwise be afraid of achievement, confronting a challenge or engaging with a co-worker. Games encourage bold, brave and experimental behavior.
That’s such an interesting point of view. What made you start it?
I love play and I love what it does to people. It makes us tolerant. It makes us kind. It can make us a bit competitive too, but there’s something great about the spirit of competition when it’s in the context of play. It makes us empathetic, and often in ways nothing else can. I long held this belief that games does a better job in making complete strangers connect with each other than almost anything else in the world.
I can relate to that. I was an avid gamer in my teens and I played World of Warcraft and went to Dreamhack (world’s biggest LAN-party) and I met so many people through my guild and through games in general.
Yeah. I mean, wow. You get total strangers to collaborate on highly co-operative challenges, like a dungeon or a raid. And you meet in the simple pretense that you just like to have fun together and that breaks down barriers. You’re just having a good time and before you realize it, you achieve incredibly difficult things together. That’s powerful.
So when I think of play my mind goes immediately to children. What are your thought on that?
I’m fascinated by children and how, when we’re so young, absorb information like a sponge. But, because we’re limited in our ability to communicate, we learn through play. Then, we grow up and unlearn how to play with boundless creativity and energy. Most people that I know whose careers suffer are because they’ve lost the fun in what they do. I think that’s when people stop growing and finding success. They’re not enjoying themselves. I think there’s something to learn from just how much fun propels us to achieve.
I agree. Enjoying what you do is so important for your well-being and quality of life and since we spend so much time at work it’s interesting that we’re not really thinking about that in the workplace.
Exactly. I don’t know why companies don’t think that’s a fundamental thing and ask themselves “How can we make sure that these people have so much fun at what they’re doing?”. That’s just the key to all of it. Too many places I’ve worked at have no concept of fun. There’s no play whatsoever. How do you want me to make something meaningful if you don’t prioritize fun for me and among my coworkers?
Maybe it’s because work is supposed to be “serious business”?
People often think of games in a work context superficially. Gamification is a good example of this. We’ve all seen apps where they’ll add some kind of badge system to motivate you towards repeating unsatisfying tasks. We’ve become quite good at seeing through this. Rather, what we want are satisfying feedback loops that reward deep engagement and motivate us to succeed. Figuring out that loop enables people to achieve. This in turn creates positive systems where fun leads to effective work and positive outcomes on all level. Somebody who makes play a core function of how they work isn’t just benefiting their workplace. They’re achieving more in their own personal career and their trajectory has a greater upswing.
So — the million dollar question here. How do you start applying more fun into your company?
They key is to design around a key emotion that triggers happiness. For example, in my design studio I want people to feel really creative andI would construct a playful experience around creative exploration. Maybe cover the wall in paper and ask everyone draw only with their feet, who knows. I would construct constraints like rules or win conditions, to guide the experience. This helps eliminate fear and measure progress, which is great for short, rewarding feedback loops.
Ultimately what matters in that experience isn’t whether or not the game generated the final creative idea. Doing something like should often be done purely for the fun of it, no client or business goals in mind. What matters is that people have fun and they got away from being scared of creating weird things. That’s how you start breaking down walls.
So designing around an emotion — got it. How do you scale that experience?
It’s all feedback loops. So try to figure out how to make that loop or grow more difficult, just like in a game where you level up and the bosses get harder. But that’s all the same loop. So how do you vary it? How do you bring that type of design thinking into spaces? How do we help organizations think about what key emotion they want to design around, both for employees and customers? Then it’s also about asking yourself what key emotion you want to access each day and designing your own playful experiences. Just learn to access those as frequently as possible.
Could you translate this to gaming terms?
So, the type of gamer I am is an explorer. I like to wander and see new things. In a game like World of Warcraft, I love expansions but I won’t really get into playing the end game. I lose my motivation because I’ve seen everything and I don’t get to explore anymore. It becomes repetitive. Everyone has different motivations. Game designers must be mindful of that when you’re designing those loops and think about what motivation everyone has. There can be some people who just want to explore. Others want to finish and complete things, they’re very achievement-driven. Still others are very competitive and just want to win. There are many different play styles out there. You have to be aware of which one you’re designing for.
How do you align the organization’s motivations with the people’s motivations?
A lot of it happens in the hiring process, but that’s a bit idealistic since there’s so much discovery that happens when someone joins an organization. I think it’s important that you’re flexible as an organization to deal with that. I’m a big fan of Richard Branson and what I like about him is that his methodology for managing centers on bringing in great people and then giving them everything they need to make incredible things. Hire well and get out of the way. I think that is a good example of an organization not just expecting their people to wrap around their goals, but the organization being flexible to enable their talent to forge a path.
So when I hire someone I don’t only fixate on how good they are at something, even though that might be important. I like to focus on how much they love what they do and how warm and fuzzy they feel about it. If I can see that there’s a similar motivation between us I know that they will grow with the organization and vice versa. I expect my company to embrace their growth. What do they bring to the table that’s currently not there? How can I change my goals so I can learn from them and how they best succeed?
Obviously there are bad apples. But if they simply do things differently than I’m used to, I try to make a point to learn why they are so passionate and see if there’s something to glean from it.
That seems like a scary thought if you’re a CEO of a company — changing as you hire more people.
Yeah. But I think it’s always important to put yourself in check. No CEO has the secret on how to best run a company by themselves. No one knows the best way to do something 100%. You can’t go in there and be like “I’m The Guy and I know what I’m doing and if you got a problem with that — get out of my way”. Sure, there are those who work that way, but it’s not my approach. And since fun is such a big part of PlayWell, I have to divorce myself from such unfun and soul-sucking procedures. For me I see it as “we’ve got this new cool person and she’s amazing for a reason”. Maybe we can learn from that.
Since we’re kind of already talking about it — what does culture mean to you?
Well… I don’t think it means ping pong tables. I think it means your human goals and that it’s largely about the attitudes and the environment you set for the people who work there. I don’t want to build a workplace where people feel like we waste our time, but I also don’t want that culture that assumes work is everything. I’m having a kid soon and I don’t want to feel guilty about going home to see my family. Even if you do what you absolutely love, you have to disengage from it daily in some form and be a whole person. I don’t think people will continue to have fun at what they’re doing if they don’t have balance in their life.
That’s the best way I think of culture, at least at PlayWell — Are you a happy and balanced human being? Do you have time to shut off and not answer emails for me? If you do, then I think the culture is okay.
There’s been a lot of talk about failure in culture lately. What’s your thoughts on that?
I think it’s really important to cultivate an environment where it’s okay for people to make mistakes and be human and be cool with it. For example, we set up a class and we didn’t fill it up and I was really nervous that my partner was going to start doubting our business and thinking it sucks. But there could be a thousand ways why it didn’t work. So just try again. It’s fine, it’s nog big deal. We just try harder next time and do new things. We try to learn from our mistakes. In a way, starting a new business is like a baby learning to walk. You’re definitely going to walk into walls, get a few bumps and fall flat on your butt. Just keep coming back up and keep trying.
How do you work with the culture at PlayWell?
I believe it starts with communication and people not being afraid to speak up. If you need more money, say so. That’s what I want my co-workers to do. I’ve always been uncomfortable with people who don’t speak up but I’ve learned that there’s a lot of times people have things they want to say but they can’t or aren’t able to say it. So many people don’t work well with boldness or confrontation of any kind. That’s okay. Or maybe they have anxiety, that’s okay too. A company’s culture should be inviting to different communication patterns. Everybody needs to feel like they can come forward and say whatever they need or want to say and ultimately be heard with no fear. I completely appreciate that.
So how do you work on improving the culture?
Communication is key and the best way to improve culture. We’re always trying to become better at that. Honesty goes a long way. I tell people if I don’t feel comfortable doing something and I think what that has done is allow others to be upfront with me and provide or receive support.
So, it’s about role modeling?
Sure. Maybe I’m assuming too much, but I try to role model the behavior I want to see in the company.
I’m curious to know if you’ve actually sat down and talked about your culture.
Not explicitly. We’re a small team and speak plainly. I hire people I love to hang out with so I think there’s a natural cultural fit there. Maybe I shouldn’t assume as much. I bet I could learn a lot if I had a culture-focused discussion. I like to have that personal connection because we’re in the weeds together.
What’s your biggest challenge as a startup founder?
There’s a few things that stand out. First of all is focus, and by that I mean pre-money. When you haven’t raised money and you’re not making a ton of money out the gate, you’re probably working on the side and it’s very hard to get a company off the ground if you’re not fully focused on it. I think the greatest secret to a startup is tenacity mixed with a dash of delusion. Great founders have a mix of both. They go back into the fight over and over assuming they’ll win at some point. And that type of vision focus can lead to success.
But the other thing is delegation. It’s a hard quality to learn as a leader because often leaders want to do everything themselves. We have a hard time letting somebody else take a side of the business when we’re not sure whether or not they’ll execute the way we would. That’s really hard. But I think Jack Dorsey said something along the lines of that if you’re the CEO and you’re doing all the work, your company is going to fail. Your job as a CEO should be more about building and guiding a team while you work alongside them.
As a founder, you maintain this vision in your head about the company and you want to execute it exactly how you imagined it. The great irony of that is… you know that phrase “a face only a mother could love”? Sometimes an early stage company is like that. It’s a bit ugly for awhile. But you love it and think it’s amazing no matter how bad it might be at the current time. It takes outside voices to say “this doesn’t work” or “you need to cut this and focus on that”. The important question is “How do I involve more people and stop trying to do everything myself?”.
Who can that outside person be?
This is going to sound very cliché, but 75% of the success of PlayWell is completely attributable to my wife. She’s got a fantastic mind. She’s not a gamer, so she doesn’t look all my ideas with rose-colored glasses. It’s great. She makes me responsible for things that I set out to do. You need to be accountable to someone who’s going to be blunt and make you own up to your weaknesses. So it might be a wife, an investor, parent or best friend. But having someone that doesn’t put up with your crap and let you slide by while keeping you humble and honest is really important.
So, we obviously talked a lot about play and fun. How does that, and other serious stuff, relate to those two concepts?
There’s two ways to respond. One is, I don’t know and it’s something I should think about and design into my experiences. Like, how do you bring fun into conflict resolution or managing failed expectations? The other answer is that fun is a critical part of as much as possible of what we do, but some things are just inherently not fun. I think there’s always going to be some stuff that has a serious tone to it. And that’s okay too. A lot of my push towards fun is because most companies we interact with are starving for it. That doesn’t mean we can’t be serious. Sometimes paperwork just needs to be paperwork.
You don’t want to undermine the seriousness of certain situations with playfulness. Emotional intelligence plays a big role in understanding the place that play should occupy in your work. I want to make sure that the people I work with know that we’re all about having fun but that I take them seriously and that their well-being is important to me.
So, what’s next for PlayWell?
We’re constantly trying to figure out how to increase conversion and make our learning experiences better. We’ve learned that we’re very limited in the way we can execute things when we’re not working full-time on PlayWell. The obvious blockage to success right now is funding. We’d like to raise enough money so we can work on this full-time and bring in someone that’s great on marketing and community building. We also want to bring in an education expert to refine the design of our education piece.
So that’s where we’re at and I’m scared to death of it. But everything I’ve done in my life that has paid off I was sacred to death of at some point, so I guess that’s a good sign.
Thank you so much Collin for your insights and helping the world become more playful! Where can people find you if they want to talk to you?
Thank you! You can find me on Twitter and you can read more about PlayWell on our website and follow us on Twitter. We also have a Medium publication.
I’m researching culture building in startups for my MA in Digital Media Management at Hyper Island. For more info: http://bit.ly/building-startup-culture
