Episode #7 – Boldness over Assurance

Clayton Lengel-Zigich, Roy van de Water, Derek Neighbors and Jade Meskill discuss the next item in the Gangplank Manifesto: boldness over assurance.



Jade Meskill:  Hello, welcome to another episode of “The Danger Cast” where we talk about the culture and design of Gangplank. I’m Jade Meskill.

Roy van de Water:  I’m Roy van de Water.

Clayton Lengel‑Zigich:  I’m Clayton Lengel‑Zigich.

Derek Neighbors:  I’m Derek Neighbors.

Jade: We’re continuing our series and talking about the Gangplank Manifesto. We talking about Boldness over Assurance.

Derek: I don’t know if I feel comfortable talking about this.


Jade: Let me assure you, Derek, it will be OK.

Roy: I am only participating because you said this would be good.

Roy: Is it all right if I participate in this broadcast?

Jade: We’re demonstrating how assurance might work.

Clayton: Well we got all the jokes out.


Jade: Derek, you remember why this came up?

Derek: I am trying to rack my brain on this, I am not remembering an exact example or an exact reason why this came up, but I think it was more that people had scary ideas a lot, but they wouldn’t really act on them.

I think part of what Gangplank started to do was be like the teenage catalyst that like, “Hey, it’d be really cool if we lit a can of hair spray on fire.”

Jade: I did that once.

Derek: Normally, you’d think, “I wouldn’t do that, that’s dangerous,” but instead Gangplank became a place like, “Yeah, you should totally light that on fire. You should throw it.” It escalated to that…


Derek: “You know what would be cool, if we’d throw the whole propane on the fire. That would be awesome.”

Roy: Then we made it into a kid’s event.


Derek: This is kind of the one that embodies the kind of whole “be dangerous” spirit which is, it’s the thing that says, when you have something in your gut, that you totally know, “If I could do this, this would be a really big deal, and this would make a real impact.”

Then your lizard brain talks you out of it, tells you that you shouldn’t do it or that you’re not good enough to do it, that sort of thing.

What we tend to do is, we tend to go around and try to get assurance from other people that It’s going to be OK. Not until we have enough of that currency of assurance do we actually execute. This is saying, “Just go out and execute it, and if it’s a right thing, it will be awesome, if not, that’s OK. People will support you.”

It doesn’t mean be bold from like a jerk’s perspective, when you know you should be doing something, do it. Don’t be passive in doing it.

Jade: Just like “be dangerous” doesn’t mean jump off a cliff without a parachute. It’s about taking risks.

I remember that we’re having a lot of trouble with getting people to even show up. There was this weird resistance to, needing to be prompted a whole bunch of times, told by a whole bunch of people, to even walk in the door at Gangplank.

I think that also informed this virtue that we put out here is that, you should just be able to take the leap and just walk in. Don’t worry about it being scary, it probably is scary and that’s OK. Just do it, just get out there and try it.

Roy: That’s interesting. That’s always one of those things where I’ll like, if Gangplank costs money, it would be easier because then you are buying your assurance.

Jade: We’ve had a lot of people tell us that. If I can make some sort of transaction, it eases that tension.

Derek: I actually think that, now you kind of spark my memory a little bit. I think a lot of where this came in is, we got so many complaints when we moved the Gangplank.

Gangplank 1.0 you had the kind of Come in, there was a secretary downstairs for another business. When you came in, you are like, “Is this Gangplank?” They would say, “Oh no, they are upstairs.”

You’d come upstairs, when you open up the stairs, there were some desks right at the front of the stairs that you could kind of say, “Am I in the right place?” You could get assured twice before you engaged.

We moved into the new building, you walked into a lobby and there was no desk in the lobby, there was no receptionist in the lobby, there was nothing in the lobby.

When you walked through the lobby, you were still in this wide open space where there were no desks. It was obvious what the primary desk was. We would get complaint after complaint, “You should really put a desk up front so that people know who to talk to before they come in.”

It was a pattern that kept repeating continually, people that were in the space all the time, “That’s dumb, just come in and talk to people.” What we kept hearing was, “Because some people, they need to understand, and they need a way to interact.” We started to really talk about, “If that’s the type of person you are, Gangplank’s probably not right for you.”

I think that translated into the Boldness over Assurance. If you need to come in and you need to be coddled, that’s probably a deficiency in interacting with Gangplank culture that is going to hurt you long term.

Roy: And hurt Gangplank, if it’s so difficult like that.

Derek: Hurt you and hurt Gangplank where if you come in and you are going to say, “Yeah, I am going to have the confidence to walk in and own it, and deal with it and do it.” You probably are embodying that boldness of like, “I am scared crapless. I don’t know anybody here, I don’t know what I am doing here, but I am really scared but I am just going to put a smile on it and act like it doesn’t bother me.” It works out.

Jade: You know what’s funny? I still feel that way sometimes. I was away for a while and I came back and I didn’t know most of the people that were here.

I went from knowing everybody to knowing just a few people. Definitely had to re‑kick in those values, “That’s OK, I’ll just go talk to them because they’re here and they’re a part of Gangplank, too, so it will probably just work.”

Roy: They don’t want to be talked to, they probably would’ve stayed home.

Jade: Or gone somewhere else.

Derek: I think that’s translated into everything from relationships to municipalities to relationships to third parties, to starting new initiatives, to.. you name it. That’s one of the things in community building that’s difficult.

If you are going to try new ideas that are truly new, you’re never going to get assurance. In fact, you are going to get the opposite of assurance. You are going to get people telling you, “That’s not possible, you can’t do that, that seems scary.”

Clayton: Yeah, nobody tried this before.

Derek: Right. If you don’t have boldness in what you are doing, you are never going to make it. We tell people all the time one of the ways you know you are doing good work is when people are getting mad at you. Because when you challenge the status quo and you put it in people’s face, that you are making a dent in the universe, they will attack the shit out of you.

If you’re not bold in doing that, what do you think is going to happen when you start to get attacked? You are going to fold like a two dollar Walmart chair with a 400‑pound fat lady sitting in it when they come after you. You got to have some boldness to own it.


Jade: Just like that analogy, that was pretty bold.

Roy: Walmart chairs are even made for 400‑pound fat ladies.


Derek: Or a 400‑pound fat dude.

Jade: Don’t discriminate there.


Derek: I can say that, as a fat kid.

Jade: Another dimension to this is, we have a lot of people who are entrepreneurs, who are starting their business, trying to make it work, trying to grow.

There are different phases of their organizational life. Boldness is certainly required in that area. If you are looking for assurance, starting your own business is no way to get it.

Roy: Can you imagine being the boss of your own company, who are you going to ask for permission?


Clayton: There have been a lot of people that I have talked to that, based on their personality and the things that they enjoy, would be good fits for Gangplank. They’re very creative or they have the streak in them. I see them a lot, especially on social media. They’ll be talking about how they’re upset about work, they’re upset about this. They don’t have enough, whatever.

I’ll tell them, “Hey, you should go to Gangplank.” It’s amazing they can talk such a big game about all the stuff that they want to do. They talk the game of the status quo basher and the be dangerous stuff.

When push comes to shove, the litany of excuses comes out. “It’s too far. I don’t have the time. Who’s going to do this? Blah blah blah.” I always think that’s interesting that it’s very easy to sound especially bold but then the actual practice of being bold, that’s the part that’s impossible for some people.

Derek: They especially have no excuse because they even got a person on the inside, for them it’s safe.

Jade: Giving them assurance.

Derek: Right. They should be able…

Clayton: I worked with someone once. It was actually right after I left to come work for Integrum. He was still with the old company, he hated it even more. I told him, “Hey, you’ve got to come to Gangplank. You are a designer. There are all these people you can talk to.”

He showed up, we talked for five minutes, I said, “Yeah, this is over here.” I did my best to make him feel welcome. He sat on the couch for 10 minutes and then he left.

Jade: We’ve received numerous angry emails about how “I showed up here and I sat down at a desk, nobody said a word to me, how dare you guys run an operation like this?”

Derek: I think my favorite email exchanged something like that, it kind of relates a little bit to this. I made some comments about downtown Phoenix in the state of downtown Phoenix, it upset some folks.

Somebody drove all the way from downtown Phoenix, came right up to the door of Gangplank. They took pictures of the outside of Gangplank, took pictures of the sign of Gangplank. Then they drove back all the way back to Phoenix and they wrote this blog about how horrible Gangplank was, a bunch of things about the people inside of Gangplank.

It was hilarious to have almost everybody at Gangplank call them out, “Did you really just drive 20 miles to come take a picture on the outside and not come in and talk to anybody and then say how horrible we are?”

The person, they’re human, their response back was, “I came because I wanted to talk about it but then I kind of chickened out the last minute, then I just took a picture and turned around and left.”

I think that’s the status quo, that’s what we were talking about when we were not only criticizing this particular thing. It’s also the embodiment of that’s what happens when you look for assurance and you’re not bold.

If you are really passionate about it, why wouldn’t you come in and talk about it? Because you are afraid. I think that boldness over assurance is saying, look, it’s OK to be afraid. It’s OK to want to be coddled and want to have assurance. Everybody wants that when they’re afraid.

It is the difference between walking through that fear and doing it anyways and turning around and walking away instead of entering the door. That, to me, is in a nutshell what boldness over assurance is.

It’s walking through the door when you’re scared shitless instead of turning around and going away, and making some excuse why you can’t walk through.

Roy: It’s not just about walking through the door either. It’s about everything that you do inside of the space and everything you end up doing in life.

Jade: Sure, that’s the great thing about boldness is that it’s really easy to continue being bold. The hardest part is doing that first part where you just open the door and walk in.

That’s obviously a metaphor. It’s not just about coming into a Gangplank but it’s just taking that first step down whatever trail you’ve started, continuing that momentum gets easier and easier and easier.

That would be my advice to someone who is struggling with not having boldness in their life, something scary that comes up that you think, “I don’t think I can do this.” Just do it. With practice, you’re going to get so much better and be able to not worry so much about needing that assurance.

Clayton: I found that I am really good at building up in my mind all this stuff that’s going to happen or the way interactions are going to play out. The way people are going to be and how good or smart, or whatever they are.

One thing that’s helped me is, to try and remember, just assume that I am wrong. “I think I am right about a lot of stuff, but I am going to assume that I am wrong, that everyone in Gangplank is better than me, and they won’t pay attention to me.” If I assume that I am wrong, I’ll just see what happens. That’s the same thing I think you’re making a punch in.

If you take that first step, then you can shatter all those assumptions, that whole thing you built up in your mind breaks down and now you are dealing with the reality of it and it’s a lot easier than you thought.

Roy: And it gets easier every single time that you are bold because almost every single time that you are bold, you’ll get a successful reaction. Every once in a while it will fall back, it will fail. It sucks if it’s the first time you tried, that you failed.

The nice thing is you can show up at Gangplank and I can assure you that walking inside, you are not going to fail if you talk to somebody.

Jade: Even if you fail, that boldness still lives on. You still have that success of just being bold enough to try.

Derek: I guess, if up to me, if I think of this a little like perfection. I see a lot of people that don’t ship their work, or take forever to do something because they are waiting for it to be perfect like, “Oh, if I just get this one last thing, it will be perfect.”

When we look for assurance, we are doing the same thing, we’re saying, “I am afraid of something.” If only I can be assured of this, then I would do it.

I would quit my job and go do this other thing if I could be assured that I would have health care. Well, then if somebody says, “OK great, you’ve got health work.” “Oh, well, I would also need to be assured of this.” You can continue to just say, “that if only I were assured.”

When you walk and you move into boldness, what happens is, you are not any less afraid. If I am afraid of public speaking, getting up on that stage and taking about it, I am just as afraid every single time. The difference is by acting in boldness, I start to believe that, “OK, I am just as afraid but I am able to reassure my own self much quicker because I’ve got more boldness than I have weakness.”

I think that’s one of the things people think of, “Oh, if I only get to this level, I’ll stop being afraid.” The reality is the best people in the world are still afraid at some level. I guarantee you there are major league pitchers that go out to the pitching mound and they’re still afraid. The difference is they just walk through it. They have the ability to say, “I am just going to walk through it.”

Jade: I think that wraps up our discussion on Boldness over Assurance. Be sure to catch us next time on The Danger Cast. Thanks.

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