Creativity can change the world | nonprofit leader

Kimberly Howard Wade
I always thought that I would end my career as a Cabinet member in the president's office. And the Cabinet position doesn't exist. It was Secretary of Culture. That there was actually like a secretary of culture that managed and coordinated with the NEA and the NIH and the National Endowment for Humanities, as well as work sort of cross culturally across the globe with other countries around arts and heritage and humanities.

Dave Weich
Hi. I'm Dave Weich, and you're listening to Work-Shaped Life.

When young people are given access to creativity, they can change their world. That was Dan Wieden’s thinking when he and his family established Caldera. Every day, you can create who you want to be. Caldera, a nonprofit based in Portland, programs year-round in-school classes and weekend intensives, and an overnight summer camp where kids gather on 120 acres near Sisters in Central Oregon. Since 1996, more than 15,000 middle school and high school students have participated. Kimberly Howard Wade is Caldera’s executive director.

Kimberly Howard Wade
I've been at Caldera four years going on five. So I'm in the beginning of my fifth year.

Dave Weich
I met you, fifteen years ago? You were the Trust Manager at the Oregon Cultural Trust. You did that job for a while. Was it five years or more?

Kimberly Howard Wade
It was five, yes.

Dave Weich
At the time, I knew you as this person who had been an actress before that, so let's just rewind. What do you think of as your first professional job? As in, the arc of a career maybe was getting started.

Kimberly Howard Wade
Well, there's two things. There's a start and then a stop, and then a start again. So my first job out of school, out of undergrad, was as a production manager—project manager, let's call it, project manager for an advertising merchandising company. So companies that basically put logos on things. It was called Red Sail Advertising. It was in San Francisco, and our biggest client was the Hyatt. And so I was constantly putting the Hyatt logo on like pins and hats and like notebooks.

Dave Weich
Okay, so you did that post-college, fresh out of getting a political economic history degree.

Kimberly Howard Wade
Exactly, exactly. There's no tie. I studied political economic history to make my parents happy. My dad was at that time, had an MBA, a master of business administration in management. My mother had a law degree and her law firm was growing in family law; had been a lovely history teacher before that. And so I had business and history, and they both wanted to see me have a job that was going to pay the bills. And so when I was in college, I thought, well, what can I study that's gonna show them that I have that intent? Meanwhile, I was running a theater company in my college. I started a little theater company. We created a business model and everything. We called it Dramatic Art Society, and we produced three shows a year. All we had was a faculty sponsor.

Dave Weich
So at the time, I guess, you just didn't…did you not see a career path, a viable career path, certainly one that would make your parents happy but maybe one that wouldn't even support you in theater at the time?

Kimberly Howard Wade
Not at all. I've always been this sort of bifurcated brain. I've been very left brain and analytical about survival and very right brain and creative about solutions. And so I couldn't think of my way of surviving in the theater at that time. So my solution was if I go to graduate school, I'll get a Master of Fine Arts so if I can't get work, I can always teach. And that was my logic. So I went and got my grad degree. And then my first professional job after that was as a college professor. I maybe manifested that on accident.

That's when it went back to something that is very central to who I am today and probably was growing even before that, which was really wanting to give these young people that I was teaching their own creative voice.

And so I worked really hard to make sure that these young people that I was in charge of at this time, even if they were going to go off and become a doctor or an engineer or a social worker, that they were learning something from theater that was going to go with them in terms of the human experience.

Dave Weich
What did you learn from theater that went with you?

Kimberly Howard Wade
The thing that's biggest to me that keeps resonating today is that it's not about me. That theater, acting is not about mask; it's about revelation. So for me to be the best possible performer, I need to get out of my own way to take my ego and put it over there, literally off stage in the green room in a box so that when I walk on stage, the voice of the playwright, the voice of the character and what the character needs in relationship to the other people on stage is what the audience sees and hears and comes to understand.

And I just recently, in thinking about Caldera, had to make a similar decision where I'm like, this is not about me. It's not about my vision and what I want from my own personal career. It's about what's right for this organization, if this organization is to continue on for the next 30 years making the impact that we're making with middle school to high school youth in this seven- year cohort model.

And so I said, okay, take my ego, put it off stage in a box and let the legacy and the purpose of this organization speak to me about what the decision is that we need to make.

I hope that's not too woo woo. You can edit that part.

Kimberly Howard Wade
No. No, no, no, that's great. I mean, one way that I often think about work that I think does apply to you very directly is that there is the oft-told Malcolm Gladwell, ten thousand hours, he wrote about that—it was someone else's study, but he talked about Michael Jordan putting ten thousand hours in to become expert. How I always sort of interpreted and synthesized that was that, sure, if you're to be a professional basketball player, you need to focus on a task that deeply.

Most of us, however, do not have careers that are so deep and narrow. So the idea of doing ten thousand hours at any one thing is probably not that relevant to a typical person. And so the question that I always ask and what I tend to sort of share with people who are asking for advice of one kind is what are your ten thousand hours? Because that's what makes you and that is how you bring value to any given organization or task at hand.

So you decided at a certain point to pursue something on the management side. How did you wind up at the Oregon Cultural Trust as the Trust manager after being an actress?

Kimberly Howard Wade
It really comes down to a question… The ten thousand hours for me is: How can I make a contribution? How can I do something for the world? What is the... Yeah, what's my contribution? What is my service? What am I giving back? And I'm constantly asking myself that question. Is what I'm doing in service to something bigger than myself?

Dave Weich
Right. And that seemed more likely to be something you could achieve if you were in a role not on the stage directly with the audience. How were these ideas or values instilled in you? Maybe growing up by your parents. Where did this come from? These ideas and this sort of desire to pursue them.

Kimberly Howard Wade
The art part, I'm not sure, to be honest. Like I said, my mom's an attorney and my dad was a businessman. However, they both gave back. I was raised in a very faithful home and we went to a regular church on Saturdays. We were Seventh-day Adventists. I don't know if you can keep that or not. I don't wanna alienate anybody by talking about that, but…

Dave Weich
It's just your story.

Kimberly Howard Wade
They were youth pastors. And so they volunteered every Sabbath, or that's what we called it, every Sabbath, with the young people. That was their favorite. They were in their 20s, so they thought it was kind of fun. They took them on ski trips. They went backpacking and camping. And they would take me along, right? Because I was their baby, and I was like three or four years old. And then my sister came along, and we'd all go. But I saw them mentoring young people on a regular basis. And that continued even when they stopped being married and when they stopped being involved with the church. They still, my mother mentors still young attorneys that are up and coming and hired into her firm attorneys that she could mentor. My dad, when he owned his own business, would also mentor physical therapists who were looking at in home health. So they both, I watched them do that. My mom is always adopting random people into our family and being like, look, I've got a new person that we're bringing in. I think that's where it comes from. They both were community builders before that was a term, and they both were nurturing youth development without a formal title.

Dave Weich
So from the Trust, you went to the PGE Foundation. And now, of course, you're the director of a nonprofit. While all this is happening professionally, you had twins.

Kimberly Howard Wade
Yes.

Dave Weich
What does the Kimberly, who is now a mom of two twins, who are now how old?

Kimberly Howard Wade
Ten and a half.

Dave Weich
Ten and a half. What does that person think about work that the person who had not yet had those children maybe didn't know or didn't think?

Kimberly Howard Wade
It has to have the outcome. If it doesn't have the outcome, it's not worth it. I've spent a lot of years now here at Caldera—not a lot, but it's been a challenging work environment, and it's taken a lot away from my family. And so part of my aspiration now is to see this through to the success point where I can say, Caldera has landed, right? We are now an organization that's gonna live 30 years and beyond. There's some key indicators that this organization is going to thrive beyond my leadership.   

Another way of putting it is that the aspiration that I had in my youth, because I'm now middle-aged, has turned more into a striving. I'm striving to make something happen that doesn't cost too much in terms of what I lose on the other side.

Dave Weich
It's a big lifestyle change and it changes things. But what would I not understand that you actually bring to work now that maybe you didn't. Like maybe you're a little bit more divided, but what do you bring now that the younger Kimberly didn't? Maybe that is actually helping.

Kimberly Howard Wade
Mmm. Ah, that's a good...I do think that I bring balance. I do think I bring balance. I didn't do anything on Sunday, for example. It was really hard to not do anything on Sunday. And it partly because I wanted to model to the twins, what it looks like to do nothing because they are constantly looking for something to do, right? Entertain me, entertain me, or if you won't entertain me, then I'm going to be on my screen and we take that away, you know, we're like, don't. So what does it look like to do nothing? So I bring that, I think I bring that now.

This winter, I took off every Friday. I just blocked it off and I told everyone every Friday for the winter, I'm gone because the twins don't have school on Fridays. And so even though the snow was like on the mountain, we still took advantage.

And we were there on some of the good days and we were there on some of the bad days. They started calling me ski mom because I would invite a couple of friends, you know, in the third row and put the skis up on top. And so we skied every Friday, and I got to be in like the most beautiful part of the, to me, I love the mountain. I love snow. I love a clear blue sky day with snow. And I love skiing with my boys. They're awesome.

I love seeing them on the mountain from far away, and they'll be like, “Mom, look at me!” It's like the best thing that you can do as a family, I think, because you're active, you're outside, everybody's having a good time and you're really tired at the end of the day. And we have quality time in the car both ways. My younger Kimberly would never have thought to do something like that. It would have been like, I'm just working.

I've got stuff, I've got goals. We've got to meet this goal, we've to meet that goal, I'm just going to keep on working. And no, you've got to stop and just be in space with your peeps.

Now, the flipside of that is, I read something that Warren Buffett said about good CEOs allow for time and brain space away from the work. And the first day that I went skiing, I didn't even actually take the twins. It was like the best powder day. And I was just like, Well, I'm going to go on my own. They have school. I'm going. And there was like long lines, but it didn't matter. It was beautiful. And I was on the lift, and there was that quiet that snow makes. And it was a blue sky day, fresh powder. And my brain just was like, pffft. And I thought, This is what Warren Buffett was talking about. You have to step away from it. You can't always be looking at it. Because I came up with like three or four solutions that had been really weighing on me while sitting on that ski lift.

Dave Weich
Yeah, I mean, I buy that 100%. And I think it's funny because it speaks to creativity on a lot of different levels. We work with clients of all kinds. And I think, yes, we bring a lot of experience in communication and in different applications of it to solve various problems. But on a different level, there are organizations, and the people inside them tend to be very, very, very stuck inside those organizations in their mindset, particularly if they've been there for a long time. And we just come in as a third party and probably ask questions and consider ideas or perspectives that they just haven't because they're too deep in what they're doing. And so, yes, our experience and our quote "expertise" pays off. But honestly, sometimes it's just a fresh perspective. And I think everybody needs to do that with their own work, in order to stay engaged for one thing.

Kimberly Howard Wade
Yes. And I love how you brought it back to creativity because that's exactly—not to make a sales pitch about Caldera, but that's exactly why the young people go away for those eight to 10 days during the summer. That moment where you step off the bus and you are back at Caldera and there's the crystal blue lake and there's the dirt and there's friends and there's a camera and a paintbrush and a journal, your mind does exactly what happened to me on the lift. It goes, pffft. And when you think about how much young people, especially middle school, adolescence is like such a time of…there's so much coming at people these days, these young people, In fact, one of our youth called it "soul expansion." And I just love that. Caldera is soul expansion.

Dave Weich 
There you go. Make him an intern, or her, immediately. 

Do you think it's fair to say that you have the career and probably just the brain of a systems thinker? I mean, you're really like finding gaps in your experience within the larger world that you want to impact   and filling those gaps. I mean, that's what it feels like from the outside. Is that the way that you see it?

Kimberly Howard Wade
Yeah, yes. ⁓ It's a nice proper term, systems thinker, dot connector.  I was watching a really bad television show called The Lincoln Lawyer and I was watching him sit at the board, right? There's always a white board in some mystery where there's like string going from photos or whatever and he's just staring at it. And I was like, that is exactly what I do every single day. The only way that I can feel effective in my work is when I can sit back and stare at the problem like this board or something and just stare at it.

Dave Weich
It's a good Post-it noteboard you've got behind you.

Kimberly Howard Wade
Because at some point there's a pattern that's going to appear and that pattern is the answer. It's just like there's something that if I can just sit and see it. And so yes, if that's called systems thinking, then yes, that's me.

Dave Weich
I mean, were you conscious of saying like from the Trust, I want to go work for a private foundation. And then after that, were you conscious of, you know what, I want to just get in it. I want to go to a nonprofit.

Kimberly Howard Wade 
When I left PGE, yes. When I left PGE, I was very conscious that I had gotten to the point where I was developing programs within PGE for PGE to implement that PGE had no business implementing because it was a corporation, it wasn't a nonprofit. We were using nonprofit partners and we were providing backbone systems thinking so that the nonprofits could just develop and get paid for it. But ultimately it was a programmatic idea. And I thought, I think I'm missing programs. 

I didn't look for Caldera, though. I didn't necessarily even look to be an ED of a nonprofit. I just looked to see, How could I do something different? And Caldera called me three times, the recruiter. The first time I asked a bunch of cool questions, apparently, and so she called me back.

And then I said, I'm really not interested, but thank you. And then she called me back and she was like, I just have another question. And then I was at the same time interviewing somewhere else. And so I told her, you know, this is not the right time for my family. And I'll never forget this. And I use this story every once in a while. I got the call from the other place. I had been a finalist. They were checking references and everything, so I thought it was a done deal. And they said they'd gone with the internal candidate. 

And also, I was ready by that time, I had like gotten myself ready to take a leadership role. At PGE, I didn't have any staff. I wasn't a manager, and I was really wanting to do that. So yes, my systems thinking was I'm ready to be a leader and actually lead with authority rather than just leading with influence. How do I do that? And Caldera kind of crossed paths with that.

Dave Weich
Where you sit today, what impact do you want to have? And I guess, how do you think that you are now in a position to have the kind of impact you want to make after however long the career has gone to this point? You've you've done all the work to get here and you mentioned making sure that Caldera is in a good, stable place. But what do you think is in the future for you?

Kimberly Howard Wade 
I always thought that I would end my career as a Cabinet member in the president's office. And the Cabinet position doesn't exist. It was Secretary of Culture. That there was actually like a secretary of culture that managed and coordinated with the NEA and the NIH and the National Endowment for Humanities, all of those agencies and entities, as well as work sort of cross culturally across the globe with other countries around arts and heritage and humanities. I always thought that I would be in my 60s and I would be appointed to that position. I don't want to do that anymore. Now I think that I can be of most use to the community is to take all that I've learned in this journey of work from Red Sail Advertising to this moment, and in about eight years—that's my trajectory; I would like to stay at Caldera for another eight years. 

Maybe I'll consult. Maybe I'll start a think tank for how nonprofits can advocate better for arts and culture. Maybe I will become a backbone, for-profit organization that helps these smaller arts nonprofits. I don't want to be a nonprofit because I don't want to raise money, but I want to help them do all of the administrative back thing that can sometimes get in the way of the nonprofit getting the work done and making the impact. So that's an idea that's been floating around. But mostly, I see myself at seventy living in maybe Jackson Hole and skiing during the winter and working with horses, next to my husband who loves horses, when it's not winter. And that's what we would do. We'll just retire that way, and it'll be great.

Dave Weich 
Excellent. First of all, that's amazing. I truly wish you that future. What's the eight years?

Kimberly Howard Wade
The eight years. So thanks to a wonderful executive director who I've been watching grow and develop over the years, I came across this article by the Harvard Business Review about how organizations, not just nonprofits, but all organizations, entities, companies, once they've gotten to thirty years, how they can go from thirty to a hundred by a couple of sets of criteria. And one of the number one criteria was that their leadership, not just the CEO, but the C level, the C Suite, have been at the organization 10 years or more. So organizations that have a constant flip of CEOs or CFOs or other leadership are not as likely to be a long-lasting brand, if you will, as organizations that keep their leadership on. That's one element. 

There's some other elements too, but that was the one and I thought, okay. And so because Caldera is an organization that was founded by a family, the family is still deeply involved. And so as part of the founder transition, when Dan Wieden passed away, I sat down with the family and I said, “Let's make this organization live beyond the thirty years that we're about to see. We're gonna be thirty years old in October. How do we go beyond that?” And I said, “I'm committed. I'm committed to being here for a full 10 years, if not longer, to make sure that this organization, the legacy that Dan began, goes on.” And so it was an MOU, if you will, a verbal, it was a gentleman's agreement or whatever you wanna call it when you're not gentlemen. And I'm committed to that. 

That was two years ago that I told him that. And so at that point I said, I'll be there for 10 years. And that puts us at 2034. So that's eight years from now. That's when the boys, or the twins, graduate from high school. So that's perfect. They graduate, send them off to college, have a big retirement party. Maybe move to Jackson Hole at that point, depending on how tired I am, or consult for a few more years and then move to Jackson Hole. 

Dave
That's great. So, OK, last question. If somebody is young and inspired by what you're talking about and what you've done, but they're at the beginning of their career and they don't necessarily see all the dots connecting, what would you tell that person?

Kimberly Howard Wade
Always say yes. Don't listen to the naysayers. Listen to your own voice. And opportunities will come that you're supposed to have. And don't think about it too long. Just say yes.

Dave Weich
Thank you so much for doing this.

Kimberly Howard Wade
Thank you for asking, it was a pleasure.

Dave Weich
Work-Shaped Life is produced by the team at Sheepscot Creative. It's hosted by me, Dave Weich, edited by Bailey Cain and Michael Nipper, with production support from Benna Gottfried, Rosie Struve, Amelia Lukas and Kate Sokoloff. 

Next time on Work-Shaped Life:

What's the longest you've ever gone without working hard?

Matt Newell
I don't think ever since I went to college.

Dave Weich
What's the longest vacation you've had?

Matt Newell
Two and a half weeks.

Dave Weich
In 30 years?

Matt Newell
Yes, but we're in America. That's common.

Dave Weich
Is it? I don't know.

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