The interviews and the content we produce for Ways We Work is about sharing what it means to do the work you love. Whenever possible we want to share our experience of working on this project, and the challenges we have. Next week we launch a new site, with new content that we’ve been working on all summer so we thought it would be a good time to reflect on the last few months, what the highlights were, what’s been difficult and how we’re feeling about everything. What we’ve learned is that it can be hard to want to share when you’re not sure how things are going to turn out, but that’s what Ways We Work is about. So, Matt and I sat down last week over a late lunch and recorded a conversation between the both of us about what we’ve been doing, where we’re at and where we’re going.

On doing Ways We Work full-time

Matt: So what’s going on? What was it like deciding to do Ways We Work full-time? It was a few months ago now, what happened to prompt you to make that decision?

Amandah: This is a tough one to talk about openly [laughs] I still have trouble deciding how freely I want to talk about it. Basically, I left a job that I loved with the Charcoal Group - and that I was really good at - thinking that I would push myself to try and do web development full-time. To learn that skill and be forced to hone that skill because I was working on it every single day in an environment where you have to be producing at a fast pace.

And… that just did not work out, for a lot of different reasons. Relationship-wise the people I was working with, I couldn’t produce at the speed or level they expected. I think there was definitely a mismatch of expectations, that was when it became time to part ways.

So then I had this opportunity to do whatever I wanted and I was questioning “do I get another job?” or is now the time to start looking at doing Ways We Work full-time and giving that a shot and seeing if that could go anywhere. That was basically the decision, you know, I had the option to so I wanted to try. I had some money saved up for a few months runway so I just went for it.

Matt: So how’s it been? Start with the first month.

Amandah: Yeah, the first month was super exciting because that’s when you’re excited about the potential of getting sponsors, you’re figuring out how that’s going to work, and how the project is going to make money. How you’re going to support yourself and the project overall and that’s kind of when there’s endless possibilities. In the first month, you think you can do anything! The hard part is figuring out what you want to do.

The second month, with slightly less cash, you’re starting to think - “okay we don’t have ALL these options what are the options that are going to be the most viable?” So you kind of refine down from there.

Then you get into the third month and now we’re having meetings with sponsors, now we know what we’re looking for and what we need from potential partners. We just have to start getting it and selling it.

Matt: So would you say after that first month that things changed, or did it stay the same? Did it come crashing back to reality?

Amandah: No, I would say the first couple months there was a lot of optimism - and there still is a lot of optimism - but reality starts to kick in after two months, because they flew by. I mean two months has flown by and you run out of money a lot faster than you were expecting to. You look back at how much actual progress you’ve made in terms of the site being able to sustain itself and that’s when reality hits. Now we just have to push and sell and get something OR I need to take on more freelance work so that I can give the project more runway. That’s when there’s a bit more pressure.

Matt: Yeah, I feel that too, a side-project takes over and all you want to do is work on it. Then you have all these other responsibilities to take care of as well. It’s finding that balance between the project and making sure you’re not dropping the ball somewhere else. I didn’t go at Ways We Work full-time, so I have to keep multiple balls in the air at the same time. I could definitely see if I was relying on it to be my sole source of income there would be a different type of pressure.

Amandah: I sometimes wonder, I know I have to try so I know it was the right decision, but I sometimes wonder if putting the pressure on it to make that kind of money was a bad call and could potentially make me like it less. That’s never been a worry before, but now it has this job to do.

Matt: You’ve had a couple of months to feel it out, do you like it less?

Amandah: I definitely do not like the project less. I was thinking about this the other day and I don’t know what else I would care about more. The whole mission behind the project is about bringing down barriers between what people want to do when it comes to meaningful work and then how they can do that as a living. I don’t know if that’s ever something I’ll not care about. This project seems to be a really good way to explore that and tell those stories.

It‘s the logistics behind the project, like trying to get sponsors and trying to make it work and growing the audience because those are all things that you should do - it’s the “shoulds“ that wear on you and that you like less. I don’t think I will ever like what the project is less.

Matt: Yeah, I agree, and that’s the main reason I joined the project; discovering what makes people tick and what makes people persevere through those hard transitions to doing the work they really love to do. Almost everyone goes through these periods of time where they’re in a job they hate or they don’t feel like they’re fulfilling their potential that they know they have. I love learning what the difference maker is for someone who says “I want to pursue what I love to do, and here’s how I’m going to do it or here’s how I did it”, and then “now that I’m doing it, does it live up to my expectations, is it everything I imagined in my head?” Of course, I think 99% of the people would say, “no it doesn’t match the fantasy in my head but it’s pretty damn amazing.” I love hearing those stories and I love hearing people talk about how they did it and it fires me up to keep wanting to do it more myself.

There’s this motivating factor to see people be successful at transitioning and knowing that when they get up in the morning it’s not a chore. Work becomes more like playtime. That’s how I want look at it; I want to make my work like playtime, like how my kids look at play. Play to my kids is just part of their life, it’s not something they have to do. If you love the work you do it becomes more like being a kid at play. That’s another reason why I love working on this project together.

Amandah: I think what always brings us back to that vision is when we do interviews with people and we talk to them. It’s so easy to get caught up in all the other stuff that goes along with the project to forget about that and that’s the most important part.

Matt: It takes one great interview and you think “man this is awesome, I love talking to these people.” That’s another reason I wanted to do this project as well, I want to meet really interesting people. I love the idea of having that 1-on-1 conversation with people, it’s such a fun thing to do and being able to dig deep and asking them interesting questions that you wouldn’t normally be able to ask at like a networking event or something like that.

On the highlights

Amandah: So what have some of the highlights of the last few months been for you?

Matt: Oh, I mean going to California was awesome. That was just a taste; going to California was a taste of what’s to come. I think that set the tone, maybe even pushed us to want to do this more because it was the epicenter of where these people - our people, designers and developers - are running at their peak game. It’s so exciting to make that leap in a big way, going from locals in Toronto to San Francisco and all you have to do is ask people. Everyone was so cool about it and excited. That was a big highlight.

For me, I just love starting side-projects, like I’m such a side-project guy. If I could do nothing but side-projects I’d be happy. This project especially because I’ve been wanting to do something like this outside of web development and design. I find in that space it’s easy to get caught up in buzz and the technology and it’s nice to step outside of that and realize I’m still human and I’m doing these creative endeavours. If nothing else, this project just adds to my ability to be a better designer and better developer because it gives me a different context.

Note: In June Matt and I travelled to San Francisco and spent 4 days travelling to 5 different teams and offices to conduct interviews, and shoot photos for upcoming pieces on some incredible teams.

Matt: What about you, what’s some highlights?

Amandah: I would say they’re pretty close to the same. California was awesome because like you said, it was a taste, this is what a project like this can do. I just remember thinking “this is perfect, I could do this every week, every day, if we could get paid for it on top that…”

The other highlight was making the decision to do the interviews over Skype or phone call or in person. There is so much more of a connection that you make to the people you’re talking to than when you just send them questions over email.

On the different challenges of the last few months

Amandah: What about challenges, what’s most challenging right now?

Matt: I think for me the challenge is there’s a drive to want to do this project. It pushes me to be outside my comfort zone which I always love - to a degree - sometimes it’s terrifying, but it’s a good terrifying. I’ve never had to put myself out there socially, so it’s nice to take that on which is really cool. So that’s a good challenge. I think the hard challenge is just trying to mix it in with my daily life. I feel like I’m attacking on a lot of different fronts right now and it’s hard to juggle all the different balls at the same time. I just need to be smart with time-management and make some sacrifices where sacrifices can be made. I don’t have the most amazing social life right now [laughs] but at the same time too, that comes with parenting so you just kind of have to roll with it. It’s weird because I don’t have this active social life but at the same time I’m going out more than I ever have in the past so take that for what it is I guess.

The challenge is just not being able to focus 100%. I think a lot of creative people have this issue of wishing they could do their creative work without having to worry about where the next paycheck is going to come from, and it might be a bit naive. It’s hard to have to put the creative hat on and then have to take it off and think “how the hell are we going to make money with this?” Like you said, it can change things; it can maybe make you not like the project as much - so that’s challenging.

Amandah: Yeah I think for me, having done it a year and half now, but really taking it seriously in the last 6-8 months, the challenges have been a lot different and there’s a lot of different kinds. The one difficult thing for me has been, so if we compare the size of audience from this time last year to this time this year it’s amazing. It’s grown incredibly so that puts you in a really good perspective. It’s hard though when over the summer you see numbers going down or staying the same and you can’t help but start to have some anxiety around it. “Are we doing enough, are we growing it fast enough, are people just not interested anymore?” I think it’s all in perspective though, the kind of months we have now I would have been thrilled about those 6 months ago, or a year ago. It’s important to keep perspective and not letting things like that bog you down. I try to remember that we‘re doing something that lots of people find valuable and those things just take time.

Matt: That’s honestly one of the hardest challenges I’ve had with any startup; everyone wants results quickly. I remember I had one project that I worked on and it took time. It grew slowly and organically and then it took off, but it took a few years. This idea that people have a startup and all of a sudden a year later they’ve worked hard and they’ve got a huge user base and everything’s flying high - it’s just a pipe dream. There might be a few anomalies but for the most part, it takes awhile. Sometimes it takes a few iterations, or pivoting. Things just take time. I built this audio player with my brother and we just kept focusing on making a great product. We just kept pumping in things that we’d want and we kept making it and making it better and the user base grew and eventually it got over a million people using it. It just takes time and that’s one of the hardest parts to reconcile.

Amandah: One of the things about choosing to do the interviews via Skype is that it made the interviews a lot longer. Which I personally love because I think we get a much better quality out of them. People have noticed that, people have commented on the quality becoming better which is amazing. However, being in the world of creating online content I can’t help but wonder if that contributes to not having as many views on a piece. Not that it‘s really comparable but, you see sites like Buzzfeed and a listicle that probably took 5 minutes to produce is getting hundreds of millions of views and your in depth interview that took a week or more to conduct, transcribe, edit, produce and schedule out - you’re fighting for eyes. When you’re working in this space it can get to you, if you’re comparing yourself against others, which you want to do to a certain extent to have some sort of benchmark as to how you should be doing. So that’s a big challenge - but I would never go back to having shorter interviews because I just think the quality outweighs having a shorter, more concise interview.

Matt: It’s hard to judge things by looking at a short-term calendar. August was a rough month traffic-wise compared to our previous months but we won’t know if that’s an anomaly until time goes by. We did that survey and received some fantastic feedback. However, you’re not going to get the people with major criticism writing in “wow, this website’s really boring”, on the survey so it can be hard to gauge. Although at this point that negative feedback is probably what we need most of because it would show us where we’re making mistakes and where we could fix them. So maybe that in itself is a challenge - just knowing where we can improve. When everyone is telling you what you’re doing is awesome it’s hard to see the truth behind it all.

On paying the bills

Amandah: Definitely. Another challenge - just on a personal level - is that Ways We Work isn’t at the point where I can do it full-time and not have to do anything else to pay the bills. That’s okay, but the place where I’m at right now is I either get a full-time job and have to take focus away from it (which I don’t want to do, I’m only three months in I’m not ready to quit or give up yet), or I get a part-time job or keep going at freelance and get more freelance clients and buy myself more time. I think continuing with freelance is definitely the best option but the thing about doing freelance versus having a job is you are still fighting for every paycheck. You’re fighting for money with your side-project and you’re fighting for money with freelance clients and there’s no source of regular income like when you have a full-time job. There’s nothing you can rely on, you never know when money is coming in and that can make it hard to prioritize.

Matt: That’s exactly where I am. I mean doing the freelance work is awesome but it’s not consistent and it might go away for a month and that’s when I panic and realize you need to get my shit together. Then things will change and I’ll have a ton of work. Then I’m so busy but all I’ll want to do is work on this side-project that I love so much. I think through these experiences you get a good sense of where the project is at.

I’m realizing now that we’ve taken a really good swing at the first round of trying to get sponsors and feeling businesses out, if Ways We Work is something that they see value in. We’ve gotten at least a glimmer of it being something that people want but it also seems like the audience might not be big enough yet, and they want bigger bang for their buck.

Amandah: Yeah, finding the alignment with sponsors I think is going to be more challenging than I expected it to be. Especially to get to the level that we want.

Matt: It’s standard business modelling too. Your business needs to be making enough money that you can deliver on what your value proposition is. If you can’t make enough money to cover your expenses with the model you have then it’s not necessarily a business yet. Until you have customers who are willing to give you the money you need to do the job right, you need to try harder.

Amandah: I guess it’s that question of do you go at it as a business first or do you go at it as “let’s get our side-project funded.”

Matt: The hard part is that businesses that give us money are going to want us to be able to focus. They want some sort of idea that something will happen with that money. If we put our price too low, we might get a lot of interest but it won’t sustain us, so we’re in a hard spot where we can’t deliver on promises. We have to make the numbers big enough that we can take a small sigh of relief and focus on producing great content.

I think if we just continue to move forward and focus on what we really love about the project, the rest of it will just fall in place. We just need to make sure that our intentions are known that we do want sponsorship and we do want to do this on a regular basis. Magic will happen - I’m convinced.

We're looking for 4 or 5 title sponsors for the year. If you love Ways We Work and want to support us and be part of our growth over this next year, we'd love to start a conversation: amandah@wayswework.io.