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A conversation with Ways We Work: Part Two

Reflecting on a year of working together and lessons from making a creative project your main gig.

It's coming up on a year since I started working on Ways We Work in a more full-time capacity. It's also been a year since Matt joined the project. So we figured we were due for a good sit down to reflect on what we've done and where we want to go. Matt and I obviously talk regularly about the site and are constantly working on different things but we wanted to really dig deep into how we're both feeling after the last year, what we've tried, what has worked and what has flat out failed. So we got together this week at a local coffee shop, recorded ourselves interviewing each other and took some photos of us talking with our hands.

In the last year we've done over 10 features on teams like Facebook, Medium, Photojojo, Bloc, Thoughtbot, Pivotal Labs and Igloo. We've interviewed 50+ people and experimented with a ton of things behind the scenes to keep Ways We Work alive and thriving. While we'd like to share our own experiences more often that usually becomes less of a priority with everything else we're working on. But, we're here now to share everything we've tried and learned over the last year and what it's like working on Ways We Work. We've had a few successes with weekly sponsorships, larger sponsorships, we spent a few months exploring a video series that didn't work out, we spent a couple months exploring the idea of becoming a recruiting platform and we even tried our hand at advertorial content. And while we're still learning, what has come out of the last year is that we both understand exactly what we want and what we need to continue growing Ways We Work.

We want to produce engaging content focused around how people do the work they love. We want to become a resource for people who are figuring out what work they find meaningful and how they can pursue it, and we want to partner with others who support that goal.

Matt: It’s been a year since we partnered up and you’ve got a year under your belt now of doing Ways We Work mostly full-time. Can you give us the general view of what the year has been like?

Amandah: It’s been strange, that’s the best way to describe it. It’s certainly been a series of ups and downs. The entire year has been trying to find the balance of pursuing creative freedom while also being able to financially sustain myself, and Ways We Work. It’s been about trying different things, and going step-by-step. I think it’s strange to hit the one year mark because this was never the plan, I mean none of it was planned. I just love doing this so much that I want to keep doing it, however I can. That’s the motivation. As many times as I’ve thought “I should really get a job or do something more steady for income,” it feels like giving up. Despite how many moments I’ve had where I feel like I want to give up, I really don’t. I sometimes think that most reasonable people would have by now [laughs]. In my mind, I have to try everything before I do that.

Amandah: It’s been a year since you joined the project, I’d love to hear what you’ve learned in this last year?

Matt: I’ve learned, or more confirmed, that these projects are really challenging. They're really hard and if you put pressures on them that they're not able to handle or you put expectations on them that maybe aren't fair, they can start to crumble. I've done a number of projects and the ones that succeed are the ones that just have this life to them. No matter what happens, you just keep going and going and you love the process and the core of it stays true to itself. Whereas the projects that fail are the ones that get too business too fast. Expectations ramp up and pressures are placed upon the project that ultimately buckle it in on itself because it's just not ready to hold what it's been made to hold. The dream scenario is expected to happen too fast or something. I've had that happen a few times where if the dream scenario isn’t met right away and the team gets impatient, the project fails. I'm super careful about that now.

What I've learned over the past year is that I completely fell in love with the project and I love everything about it and it's offered me some really great experiences and unique opportunities. What I've learned to do is just to not place expectations on that are too large because if I do, I know what happens; things start getting out of alignment. When I do these projects I try and do them with a humble attitude, or try not to make unrealistic expectations. As soon as I put them up there, I get into the wrong head space. I remind myself that I need enjoy the process of making content and have a vision and of what I want to see happen and then, however fast it goes, just ride the wave.

Looking back, last summer, we were like, "No, let's just be a publication. We're a community and we're small." Then we were like, "No, we've got to make money." And, "Let's be this big thing, this big platform." Then we were like, "We don't want to get VC money and be a platform." Then we stepped back and asked, "Okay, let's really think about this. What do we actually want to be?" It's good, I think, that we zig and zag because we test the waters along the way and get a better understanding of what we actually want out of our careers.

“I think it’s strange to hit the one year mark because this was never the plan, I mean none of it was planned. I just love doing this so much that I want to keep doing it, however I can. That’s the motivation.” —Amandah

Matt: You say if you go get a job you'll be giving up. What are you giving up?

Amandah: I think the focus. For me, at this point in my career it’s difficult to be doing freelance full-time even. I’m at the beginning of my career and so it’s not as if freelance work is even at the point that it’s a steady income. I’m learning how to balance that and Ways We Work at the same time and neither one is easy, neither one is steady. So all the alternatives to funding Ways We Work and funding myself through Ways We Work, mean taking away focus from it, giving up the opportunity to grow it. It means doing things like spending a day with teams, or travelling to San Francisco to create team features just can't happen.

Matt: What are one or two big takeaways you've learned over the past year? Something you maybe wouldn’t have learned if you hadn’t been doing it full-time?

Amandah: At the beginning of this year I thought it was about figuring out how we monetize Ways We Work, and literally doing whatever those options were. Doing whatever we had to to make money. What I’ve learned is that it’s far more important to determine how you want to make a living doing it. There’s a thousand ways to monetize a site like Ways We Work, we could scale it up into a recruiting focused platform, slap advertising on every page just to scrape dollars together, let anyone and everyone pay us to write a feature on them. But, the reason people pursue self-employment and their side projects is so that they have the freedom to decide how they should be run. If I just want to make money I should go and apply for jobs right now. I’ve learned what it is I love about Ways We Work, and the potential it has, and now I feel like I have a grasp on how to move it forward.

Amandah: From your perspective, what’s been the biggest challenge so far?

Matt: I originally came on board as a content producer; someone who will make things and help with the formation of the creative aspects of the project, like the vision or what we're trying to do. Helping shape that with you has been super awesome. Having to put that on hold while we tried to monetize content has been a challenge for sure. I have this energy but it had to be put on pause. I completely understand that you can't just continually do this for free, you know what I mean? Even though I kind of want to, I get it. To be a business and to sell this stuff, you kind of have to put a price tag on it. You have to sell it.

The holding pattern is definitely the challenge and sometimes you ask questions like, "Are they going to buy it? Are they not going to buy it? Then if they don't buy it, do we open it up again for free?" If people aren’t buying what we’re selling, then I’m not making new content. That, for me, is the biggest concern. Then I'm like, "Do I even add value to the project if we're not making content?" It's like, "Okay well, what are we doing? Should I just wait? Maybe I'll just wait and see what happens.” The problem is, I don't like to just wait. I want to be proactive and I want to make stuff.

“What I've learned over the past year is that I completely fell in love with the project and I love everything about it and it's offered me some really great experiences and unique opportunities. What I've learned to do is just to not place expectations on that are too large because if I do, I know what happens; things start getting out of alignment.” —Matt

Matt: Can you talk about a moment where you wanted to quit?

Amandah: Just a few weeks ago I was going through some pretty real burnout. I think with a project like this there’s always ebbs and flows. One day you might have an interview that is really engaging and you really connect with that person. That hypes you up and you’re totally psyched about it again. Then you’re stressing about money; about how many page views an interview got; how engaged readers are. It’s like juggling, making sure everything is staying up at once. Then I think you go up and down about how you’re feeling about it and how excited you are about it - especially after two years. It’s not new anymore, so you have to make sure you’re staying fresh, finding new perspectives and keeping yourself motivated.

I think there was a period a few weeks ago where I hadn’t really felt like I’d been connecting in the interviews, readers didn’t seem particularly engaged, we had a bit of a down month and were closing in on using up our sponsorship money. To use the juggling analogy, it was like all the balls were down. I’m lucky to have a lot of support in my life and a lot of people saying “if you’re still enjoying it, you should keep doing it.” I wasn’t enjoying it, so I thought “why am I still doing it?” I think in those moments, you can feel like you’re not cut out for what you’re doing.

Matt: How did you pull yourself out of that, can you describe that process a bit?

Amandah: I think just talking to other people. What caused it wasn't one thing and getting out of it again isn't going to be one thing. I had a couple of really great interviews with people who I think in particular are in this space as well. They understand. They could talk and relate to the challenges of trying to get a project like this to a point where it can sustain itself and sustain us. Those are really great. There was a lot of conversations with people where you leave and it's just like, "Okay. We could try this." I think the biggest thing is having a course of action. Whereas when you don't it's like, "Well. I'm not enjoying this and I don't know what to do." It's like I don't have anything to try next. There isn't a next step. So, what do we do? It's just stalemate. I think having really inspiring conversations with people and having really great interviews you feel like - maybe it's a placebo effect - but you feel like there's a next step. There's a course of action you can take.

Matt: What are some of the challenges you see - that you still have to overcome? In the coming three to six months?

Amandah: I would say the two biggest ones are securing a steady way to fund the project and then figuring out how it grows content wise. We're getting really good at interviews, we're getting really good at doing team features. How do we more of those? Also, how do we create more content and different kinds of content on a regular basis to help grow an audience? How do we provide even more value than we already do. What can we add? Ways We Work started as just individual interviews, last year we added team features. What can we add this year? That's a really big one.

In terms of funding, to me I think a natural next step is finding partners. Over the last two years we’ve connected with companies and teams and individuals who really believe in what we're doing and are super engaged and want to see it succeed. Finding creative ways we can partner with them. On the other side of that, a job board seems like a really good way to sort of just cover costs of the site, cover costs of the project. It just seems sort of natural. People are coming to the site to read about ways that people work and ways that they find meaningful work. If we can be an avenue for helping people find that work as well, that just kind of seems to make sense.

Amandah: What’s been the best part of the last year for you?

Matt: The whole thing. I love just nerding out when you're in these places and going into it with a really fresh enthusiastic perspective. I don't have to fake it. I can go to these places, like going to Facebook and I just get excited. It's just fun. I love meeting these teams.

I love turning things that are almost untouchable things, like Facebook, how do you wrap your head around what Facebook is as an entity? When you start meeting the people, you're like, "Oh, they're just ... It's just a group of people." You know what I mean? I know that sounds either simplified or cliché or something, but I think the unique thing we do is we go in places and we translate that experience in a way. It's like we distill all the media and products down into their most basic parts, which is the people that put it together. That's the part I really love.

I love knowing that there's just an engineer sitting in a chair at one of these companies, and he or she's like, "Doo, doo, doo. Uh-oh, server crashed. Shit. Better reboot." It's just the same thing that everyone else does, but with this scale. It's just like, "Oh, this is our server guy." Or, "This is our CSS dude. He just codes and puts it in GIT and we launch the site." I'm like, "Oh, it's kind of like what I do, it's just that it's at this big company." I have this youthful enthusiasm and excitement around visiting these places and is something that I really loved over the past year, and I just want to keep doing it. I want to keep meeting people and asking them questions.

One of the biggest surprises was just getting feedback from people when you've actually had an impact. When you've written something or you've told a story in a way that people actually really connect with and they tell you. They're like, "Wow, I really loved that." Or, "That really inspired me." Or, "I feel different now, after reading that, than I did before, in a good way." That's awesome.

“How do we provide even more value than we already do. What can we add? Ways We Work started as just individual interviews, last year we added team features. What can we add this year? That's a really big one. ” —Amandah

You can follow Ways We Work on Twitter, and follow myself @amandahwood and Matt @IamMattQ. We are currently looking for longer term sponsors to partner with and if you and your team love Ways We Work we'd love to talk to you. Just reach out to amandah@wayswework.io.