#13 Making Things Happen with Karen McGrane



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Paul McAleer: Hi. You’re listening to Designing Yourself. This is Paul McAleer.

Whitney Hess: And this is Whitney Hess.

Paul: On this episode we’re talking about work and effort. Whitney and I discuss this topic and touch on how it feels to be doing something you want to do, as opposed to something you have to do. Then we’re joined by the great Karen McGrane. Karen’s been working hard to make the Web better for 20 years. And her talks and book are highly respected.

Her 2013 Dare Conference talk, “I Suck and So Do You” was a brave, personal and really inspirational speech. So we’ll chat with her about that talk as well as the fluidity of her work and her life. That’s all coming up on this episode of Designing Yourself. Stay tuned.

So, today I thought we would talk about something we have danced around before, and that is the topic of work. I have ideas about work, and I bet you do too. And I bet our listeners do too when we just say that word. What do you define work as?

Whitney: It’s a tough one for me because when I went independent in 2008, one of the things that I was determined to do was feel like I wasn’t working every day because I was getting so burnt out on work. And work meant a lot of things at the time. It mean that place that I used to go to that I had a negative association with and I did not want to go there anymore.

It had to do with the time that I was spending away from the rest of my life. And ironically I had been freelancing on the side for three years. And I was building that business. And work was getting in the way. And it’s funny how the work that I was doing for my side business didn’t feel like work enough to actually not be able to differentiate between the two. So, I don’t know. I think it’s a super-tough one. And I’m glad we’re tackling it today. 

Paul: Yeah, me too. For me work is something that I can do and I can get paid for. But sometimes and oftentimes I don’t get paid for it. There are a lot of people who do a lot of hard work or just work in general and don’t get paid for it. We've talked about how working on yourself is work. All of this stuff that we’ve talked about over time, this is all hard work.

But it’s very different. I mean, it’s worlds away from a day job where you go to an office. And in the case that you mentioned it ended up getting in the way of the other things that you were doing. And that in turn is very different than any kind of manual labor. So there’s all sorts of different shades of work.

But there’s something that you said already that I want to dive into a little more. And you said that there’s a feeling that goes with work. So there were things that felt like work to you. What are those things? Where does it go from not feeling like work to feeling like work?

Whitney: Yeah. You know what? It’s really too bad that we don’t have another word for this, because it ends up giving work a bad name. This precise thing, this feeling of doing something that isn’t really who you are, doing something only for the money, doing something for someone else that benefits somebody else but doesn’t really benefit you, we call it work. We call that place work. We call it doing work.

And we, as a result, end up with this negative connotation of what work is. But I think we all feel as if there’s really nothing wrong with hard work. And oftentimes the more effort that you put into something the more rewarding it is. So there’s this natural kind of tension there. So, when I was going to this place called work and I started to have bad experiences there, it took so much work to get out of bed in the morning. It took so much work to get on the Subway and go there. And it didn’t feel good.

But meanwhile I could pull an all-nighter doing my own side work happily. It was the best feeling in the world to be really working hard and working long hours and being tied up in my work. And a lot of times I’ve been accused of being a workaholic. And I don’t like thinking of myself that way because it makes me feel as if I don’t have a societally-accepted separation between my life and my work.

But I have some very strong feelings that those two things are not opposites, that work is a part of life. And I have a sense that we all feel that, that the question of what would you do with a million dollars, and I’d never work again kind of thing, I don’t think that anyone would really be happy never working again.

So, over the last several years for me, it has been a journey of transforming what that word “work” means to me, going from work as that place that I go to and do the stuff that I don’t really enjoy with people that I don’t really like in a subject matter that doesn’t really matter to me, or really matter to anyone else, for that matter, and transforming that into life’s work.

Paul: So, how do you think it differs then when you are going to a place where you like the people and you like the work and you’re doing something that’s rewarding and they’re also paying you for it?

Whitney: Exactly. It’s still work, right? It’s still that place, work. You’re still doing work. You’re still going to work. That’s why it’s kind of crappy that we don’t have another word to use for it, because it has different connotations in so many different contexts. And oftentimes you don’t know what the word means until you understand more about the person who’s using it.

Paul: Yeah, that makes sense. I mean, one thing I can think about with relation to work is that for every job that I’ve had there’s always - and I’m going to guess you’ve had this, too, and probably some people listening - a honeymoon period, where you start a new job and everything is glorious and everything is just the most amazing experience ever.

And you’re like, wow, they have coffee here and it’s great. And some people, they have dry cleaning and they have massages here, and the chairs or comfortable, or the chairs are really terrible and I can pick my computer. And all these things come kind of flooding at you. And then at some point after that there’s - something changes and it turns - it becomes work. It turns into work.

And it’s not necessarily any one thing, but it may be some of the things that you mentioned - for instance, going to a place, having a commute, more likely having to do something that you would not choose to do yourself if it was totally up to you. There are things associated with work that we don’t have a choice in. It’s not up to us. But we need to do it anyway because it’s part of our jobs.

Or it is something that we’ve been entrusted with doing. And for me that’s kind of when the honeymoon period starts to fade a little bit. It’s like, oh, this is not my business. Right. This is somebody else’s business.

Whitney: Yeah. And I think what you’re describing pretty much everyone experiences. But that period of transitioning from total excitement and energy around this new thing that you’re doing to suddenly it feeling like work, I think that it always was work. You know, you always had to get out of bed in the morning and take a shower and have breakfast and get dressed and go.

And you may notice that I’m, like, struggling to actually remember what those things are because it’s been so long since I’ve done them. I had this moment of, like, am I going to make a faux pas by saying something like maybe people actually don’t do this in the morning? I don’t know.

Paul: Nobody goes to work every morning.

Whitney: Those things that you people do in the morning?

Paul: You people, you people with your working day jobs.

Whitney: You know, those same motions had to occur on your first day and on your thousandth day. And it was really - it’s very similar regardless. But I guess our attitude about it shifts. And when our attitude shifts from energized, excited to bored, perhaps, or angry in a worse case, then suddenly it feels like more effort. And I wonder if that word “work” has effort wrapped up in it. And maybe that’s part of what we’re trying to distinguish here.

Paul: Yeah, that may be it, because like you were saying, and I’ve had this experience as well, when you are working, lower-case w, working on something outside of your day job, for instance, and then you realize, wow, it’s 2am and I’ve been doing this for six hours straight or what-have-you, you just get so wrapped up in it. And you get so engrossed and excited about it that it doesn’t really feel like work.

And for some people it may not feel like there’s the same type of effort at play there. Surely there’s effort in whatever we do, right? Some things will feel more effortless just because we become better and better at them. But it may feel like more of an effort in part because of all these other things that go along with working a day job.

So there is the physical space change which usually happens for people. There’s the commute which usually happens for people. There’s the work environment which is not really under your control. All these other things go into it. So that may make it feel more of an effort than if it is you at your desk or on your couch working on something that you are choosing to do. It’s your entire choice to do that, right?

That doesn’t mean that if you go independent suddenly you’re getting to choose every single thing you do. And there are realities that go along with that. There’s the reality of running a business which - like, in my current job, I don’t have to worry about that. That’s my boss’ job. That’s what he does. That’s his job, is to kind of keep it going, in a way. I contribute to that, but it is his business, and I recognize that.

Whitney: Yeah, I think you just pointed out something really important, though, which is that money is tied up in all of this, too.

Paul: Absolutely.

Whitney: And so there’s a sense that what you’re getting paid to do isn’t what you would choose to do. And I think for the vast majority of people that’s true. I mean, let’s be real. We are privileged, very privileged, to do something that we love. And even though we’re doing something that we love, we don’t love all of it all of the time. I mean, that would be nearly impossible.

Whether you’re full-time or independent or anything in between, it would be very hard to construct a living around doing only things that you love at all times. It’s just not reality. But there is this sense that once you’re getting paid for it, that the nature of the thing shifts. And I’ve experienced this myself, which is a little hard to admit. But that’s what we do here on this show, so I’m going to do it.

In the past, there have been times that prospective clients have approached me. I’ve been over the moon excited about working with them. We go through a whole scoping and negotiation process. We end up agreeing to move forward. I receive my initial payment and almost immediately lose interest in the project.

Paul: Oh, wow.

Whitney: And I know that for me that is because money is, like it is for most people, a tricky thing. I have a lot of history and emotions and perspectives on it that end up coloring my experiences when money is involved. So suddenly when the check clears, now it’s work.

It wasn’t work to write the proposal or to negotiate or to sit at my desk imagining how much fun it would be to do this work and how grateful I am that I get to do it. But suddenly money is there. And now it’s not just my excitement that’s fueling me. But now it’s an obligation. Now there’s no way that I can’t do this work. There’s no way I can just change my mind or wake up one morning and say I’m not in the mood and just not do it. I am obligated to somebody else.

And suddenly it makes it feel like work in a way that it didn’t before. And for a while I noticed myself saying to others, like, oh, I have to work, or I have a lot of work to do, or I’m busy with work. And I didn’t like that I was referring to work in that way as kind of this thing that I had to do that was getting in the way of the other things that I really wanted to be doing.

And I realized that a big part of what creates, what gives it that connotation or that perspective or that attitude, is that money is wrapped up in it. And the beginning of this year I spent a lot of time working on personal projects. And they’re all having to do with user experience and coaching. And the work that I do for my business, with my business, what I’ve done my entire career of coming on 10 years.

And yet because there wasn’t anyone paying me to do it, I never once referred to it as work. I just came up with other language to describe it. And I think it’s interesting that there is somehow a negativity that is implied once money is involved.

Paul: Yeah, that’s a good point. I am recalling a discussion we had at IA Summit about money and work, because we were talking about something else. And I think we were discussing just kind of the field in general, the UX field. And you had asked me if I thought there were people in our field who were only doing it for the money. Is that right? That’s right. You asked me that.

Whitney: I did, and what led me there was that I often feel that what differentiates us as a community is that we’re called to do this work. And I kind of take that as a given. And I was talking to some folks about a totally different topic, topic for another show. And I kind of came to the table with this notion of, well, we’re all in this because of our life missions to do X, Y and Z. And a couple of people sitting around the table were like, huh? Life mission? I’m here because this is what I get paid to do. I don’t know how to do anything else. This is my work.

And that’s why I brought it up to you and we had this discussion around, is it possible that there are people in the field of user experience that are doing this work for the money, because that’s what pays? And that really boggled my mind. I guess it sounds naïve now, but it had never occurred to me that people would be in this for the money.

Paul: Right. And when you asked me that my answer was, yeah, of course, right away, like without hesitation.

Whitney: I know how you knew this. I mean, these people have evaded me for the last decade. I didn’t know.

Paul: Yeah, that’s fine, I suppose. And I have had some experience with folks like that, not really at IA Summit. I can say that pretty soundly. But yeah, just in my day-to-day stuff there are definitely people who are like, yeah, I’m here punching the clock and I’m going to do this work and then kind of turn around and that’s it.

I can understand that because in almost any field, it seems, there are always people who are very passionate about what they do, it seems, right? There are people who geek out about this stuff. We geek out about this stuff a lot to the point where we’re like, hey, we can take these things and apply them to life and other things. And isn’t that so cool? We’re totally geeking out about it, and I love it. And I love to do that.

But, there are people in our field and others who don’t see it that way. And maybe they don’t geek out about it, but they know how to do their jobs. They know how to do it well. They know how to do it well enough to have a job or clients or both and continue to get paid. But that’s not where they really put all their chips or even a fair number of their chips, maybe. For them it is a job in kind of the capital J sense of the word and not necessarily something that they’re thinking about after they leave the job at the end of the day.

And I don’t know if I want to put any kind of value judgment on that because there are people who - tons of people who need money and will work for money, obviously. That’s kind of how our system works, right? So, I understand that. That’s not where I am with it now. And I don’t think that’s where you are.

But it’s very different to think about that perspective on it where people just essentially are not as enthralled with this idea, perhaps. Or they just don’t - it just doesn’t apply to the rest of them outside of their work day.

Whitney: Yeah. But, Paul, you just made me realize something really important, which is that I do this work for the money. I don’t do it only for the money. I don’t do it primarily for the money. But if I couldn’t make money doing this I wouldn’t be in this field because I wouldn’t be able to survive. And this is what called to me, yes. But 10 years later I don’t know that I’m all that qualified to do anything else.

I was looking at the local jobs, back of the local newspaper kind of thing, seeing what are the jobs that are advertised in my area, out of curiosity. And pretty much everything that was there, even though they were hourly wages and pretty entry-level and requiring few skills, they are certainly not skills that I have.

And, yes, I have developed these skills over a significant period of time. But at this point if I didn’t do this for the money I don’t know what else I would do. So, you know, you’re right about not making a value judgment about it because we’re all in this for the money. Unfortunately, as of 2014 and maybe one day when this podcast is in a time capsule and they come back and listen to the things that drove our society then, they’re going to be in shock and awe. But guess what? In 2014, the thing that drives our society is money.

And that is what we use to get what we need. And that’s what we get paid with for our contributions. That’s just how it works. So, if there were no money involved in this, I don’t think any of us would be doing it.

Paul: Oh, that’s interesting. That’s very interesting. First of all, if there are any time travelers listening, thank you for listening. And please join us somehow in person at IA Summit 2014 in San Diego. That would be very cool and may have already happened.

Whitney: That is hilarious. Oh my God. I think it’s awesome that you immediately went to time travelers, because I was thinking of like a time capsule, like our podcast is going to be buried somewhere, and then like 100 years from now - 

Paul: They’re going to dig up the podcast?

Whitney: They’re going to dig it up. Yeah, that’s what I was thinking. But anyway - 

Paul: What media is it going to be on, for goodness’ sake? Let’s put it on a - you know, we’ll put it on a record. Records have survived everything. Let’s put it on a record.

Whitney: That is precisely right. That’s what we’re going to do.

Paul: This is our double EP. Anyway, so nevertheless, yes, so I am not sure. Would I be doing this if I was not making money at it? Maybe, because there is the people element that I love so very much. And when you’re saying “this” I’m still thinking about UX work and not really the podcast, although it’s slightly meta. It’s also slightly applicable because we don’t make money on this.

Whitney: Oh my God. Can you believe, people, that we don’t make money on this?

Paul: Yeah. We make zero dollars.

Whitney: You have now shocked the audience.

Paul: Well, we have a raft of advertisers, because that’s how you do. We haven’t heard from the four companies who sponsor every other podcast on Earth. We love them very much, I’m sure. Nevertheless, so would we be doing this type of work if we were not getting paid for it? I’m not sure that I can easily say no. I think it would still be very interesting to me.

Would I devote, though, 40, 50, 60 hours, whatever, a week to it? Probably not because much like you I do UX work because it pays and it’s a very nice benefit and a privilege, really right now that it pays really well and it’s very much in demand. But it may not be and probably won’t be in 30 years or 40 years. So, what am I going to be doing in 30 years? I don’t know, but probably not the same type of work.

But, along those lines, too, this is also a subject that I’m passionate about - reality television. So, did you watch Food Network Star at all? Do you know about Food Network Star?

Whitney: I have many guilty pleasures. TV is among them. I grew up in a TV-watching family. And I don’t personally see anything wrong with reality TV, though some of the shows are better than others. But Next Food TV Star or whatever it’s called, I have seen early seasons. But I’ve definitely not seen anything recently.

Paul: It is not the beast reality show. But it’s almost kind of a self-perpetuating thing. Like, they’re on Food Network, and they’re trying to find the next person to be on Food Network. So there’s something very lovely about that and kind of Ouroboros, so it’s just going in on itself all the time.

Nevertheless, last season there was a contestant named Rodney Henry. And his shtick was pie. He was big on pie, and he had a couple of restaurants where he served all manner of pie. And his show, if it was going to happen, if he won, was going to be all about pie. And I remember I wrote about this last year because I thought it was interesting.

When he was on the Alton Brown podcast - and Alton Brown is the guy behind Good Eats, and he has a lovely podcast, actually - he was talking about how he really loved pie and he loved doing it. But what he was really passionate about was music. Music was the thing that he loved. And the way he saw his life was that he did this work in restaurants - and he had multiple restaurants - and that’s hard work. I can’t imagine what goes into that. And based on television I’ve seen, it’s a lot of work.

But I can’t even imagine what goes into owning a restaurant and operating a restaurant and being the head chef at a restaurant and all those finer details that you have to worry about. It’s such a different field. He was doing all that largely because he loved music so much and he wanted to support his band and his livelihood, in a sense. Music was really what he loved doing more even than making pie.

So, we’ve talked about identity and what you become known for and kind of the balance and all that before. But what I’m interested in with this was really seeing, like, wow, this guy was essentially seeing his work as fueling everything else he could do in his life. That was the gate that helped him, probably in large part because of money.

Because of that, I’m sure he worked long hours. He owned restaurants. But he was then able to do the things that he was extremely passionate about and extremely good at and extremely talented at as well. And I find that really fascinating.

Whitney: I love that. And there are definitely people in my world in similar situations. And I find that those kinds of things do often happen to people in the arts. I mean, let’s get real. A lot of people who are artists have to support themselves through other means. But I think you’re bringing up something that had been on my mind prior to us talking but for whatever reason we haven’t gotten to yet, which is that the way in which you choose to make your money, if you are so privileged as to have a choice, which I need to recognize - 

Paul: Absolutely.

Whitney: But the way that you choose to make it, while it may not be your life’s work, your job may be different than your passion. There’s still a sense of doing something that matters and doing something that’s ethical and doing something that is beneficial to the world that really solves a problem but that is aligned with your values even if it isn’t squarely within your passion.

And what you’re describing about this baker is that he loved to bake and he knew he was good at it and he thought he could really gain a lot of fame and recognition and earn a good living by being a baker because he wanted to support his music. But what he chose to do was something that’s still from a place of love.

He wasn’t choosing to harm anyone. He wasn’t choosing to do something that’s maybe on the darker side of society. And I think when we talk about work, there is also this sense that regardless of how much we enjoy it or how much effort it requires, the work that we choose still needs to be from an ethical place that we won’t be ashamed to call our legacy if in fact that’s what our legacy becomes.

Paul: Absolutely. We would be hard on ourselves if we were allowing that type of - essentially that conflict in our lives. Now, for some people it may need to happen. But I’m thinking about what if Rodney the pie guy, instead of pie he was a big old tobacco farmer or what-have-you? That’s something that could - and maybe not today but in the recent past - have made him tons and tons and tons of cash. And then he could have gone and done music.

It really is on us to see where these things line up with each other and how we feel about them and also if they are something that we deem in line with our morals and our beliefs. And when I started my current job one of the things I talked with my boss about was really how we pick and choose clients.

And I’m not here to reveal the secret sauce, but I asked him, well, how do we really decide who not to choose? Because design, of course, is all about saying no. And he had some clear answers on that. He gave examples of companies and industries that we would not work with. We would choose not to work with these industries. And he was very clear about it. I said, OK, that’s great. That’s what I wanted to know.

So, I found it refreshing that he understood, like, hey, there are limits, and there are things that - we will not take on clients in these industries because that’s not in line with our values. And that is true for people as well. We always have - we have values. There may be desperate times when we have to make incredibly hard decisions between values and surviving, though. And that needs to be recognized, too. But I would - I mean, ideally we get to a place where people don’t have to make those types of choices, not to be too idyllic or anything.

Whitney: No, absolutely. And I think that your example of Rodney the pie guy is a great one because he came to terms with the fact that music at the moment for him wasn’t going to be the money maker. And he realized that he wasn’t going to be able to sustain his music without an income. And he chose the right work for him.

He didn’t choose any work. He didn’t, you know, choose bad work, if we can make a value judgment on it that way. He chose something that was right for him even though it wasn’t his passion, necessarily. And I think that you brought up a really important point earlier - and I know that I’m guilty of this - that I see the UX field as being filled with people that are living their passion and are exploring their lives’ work in the field of user experience.

And that might not be the case for everyone. And we have to be cognizant of that. And we have to be accepting of that, because regardless of their motivation to be in the field, it is the right work for them. That is what they’ve chosen. They’ve chosen it because it is their right work for whatever reason they’re doing it.

And so, I think that that really gives us a basis for better understanding the effort that we described before and the job aspect and the money aspect, these things that are wrapped up in that word “work”. When it’s the right work, it’s OK if it’s effort. When it’s the right work it’s OK if it’s still a job, a place that you have to go. If it’s the right work, it’s OK that you’re profiting off of it. That’s not a bad thing.

And I think that just being conscious of whether the work is right or not is ultimately what, you know, determines how it feels when you're doing it.

Paul: Agreed.

Whitney: So, tell me, because you have started a new job within the last few months, what is the difference that you experience now when you get up and you do your morning routine and you go from the same place to a different place and you have still a job that you’re getting paid for that requires effort? How do you know that you’ve made the switch to work that’s more right for you?

Paul: Well, first of all I’ve been there eight months now. It hasn’t even been a few months anymore.

Whitney: Oh my gosh. That’s crazy.

Paul: I know. It goes by quickly. The honeymoon period is over, but that’s quite all right. So, that’s a great question. And, what I feel is something that we’ve discussed a little before. But one of the things that I noticed was that this is the job where I’ve been able to be the most me so far. This is the one thus far where I have not had to be super-compartmentalized and have a very different work persona or anything of that sort. I can bring a lot more of me into this job.

And I credit that with just my coworkers and how tight we all are. I mean, it’s a good small team. So, that was one of the things that I noticed right away. And for me that was a big sign. Another was that just the work itself is generally more rewarding. There is design and research work here that is ultimately directly helping people. And that right now is my guiding principle, in a way.

The work that I want to do, I want it to help people genuinely and not it’s going to help people buy things faster or it’s going to help people play Flappy Bird better, although that would be a great side goal. I genuinely want to help. And not every project has that attribute. But a majority do.

And what I find is that when I am doing user research, talking with people about what their needs are, understanding, then, how this could be manifested in design, that’s pretty darn close to ideal because then I am helping people, helping identify needs that they have and then coming up with one way they could be solved. And that, to me, puts it squarely in the, hey, this is the right big bucket area.

Whitney: And so, when you’re doing something that is in line with your principles, does it feel less like work?

Paul: I have to pause and think about that a little bit. It still feels like work, but it’s very different, right, because if I feel that - hmm. It’s work with a different kind of effort. It’s less effort, in a way. That’s how I’ll qualify it, because then I have a very clear sight of what the goal is. It’s to help this person or this group of people that I spoke with or what-have-you.

But it feels like there’s a more direct impact, so all the work that goes into it - our standard process on conducting research and doing analysis - feels a lot more lightweight even though it’s the same process we do every time, because it’s a good one. But it definitely feels more lightweight and more manageable and more beneficial, in a way, than if I was doing it for a project where I didn’t really have a good sense of where it was going or who I was going to be helping, ultimately.

Whitney: So it sounds like it’s still work but you’re happy to be doing it.

Paul: Yes. I’m happy and fortunate, for sure. That is for sure.

Whitney: Well, that certainly is something we are all trying to achieve, so bravo to you for finding it.

Paul: Thanks.

Whitney: That’s awesome, so awesome. Well, you’ve definitely given our listeners something to aspire to and me as well. This is what I’m always trying to do is get closer and closer and closer to the work not feeling like effort and feeling as if it’s the right thing to be doing with my life and spending my time on. So, it’s a process, and that’s what we’re here talking about, designing ourselves and getting to a point where we can really achieve our goals.

Paul: That’s exactly right. Well, I’m glad we talked about work. I really like this topic. And thank you so much for sharing your thoughts on perspectives on it, Whitney. It was great.

Whitney: And thank you, Paul. I’m very inspired now by what you’ve been able to find. So, onward and upwards for the rest of us.

Paul: All right. That sounds great. Thanks.

Whitney: Bye-bye.

Whitney: Hello, everyone. This evening we are going to be speaking with the lovely Karen McGrane. Karen has been making the internet more awesome for nearly 20 years. You might know her from her seminal book, “Content Strategy for Mobile”, her work at Bond Art + Science, or one of her many, many articles in publications such as A List Apart.

Last year, Karen spoke at the Dare Conference. Her talk, “I Suck and So Do You” was shortlisted for Conference Talk of the Year at the 2014 .NET awards, a well-deserved honor. Karen, thank you so much for joining us today.

Karen McGrane: Yeah, thank you for inviting me. It’s a real pleasure to be here.

Paul: Thanks. So, I thought we’d kick things off with talking a little about your employment and you job situation, believe it or not. It’s not going to be an interview, though, I promise. So, you’ve been independently employed for a long time. And I’m curious, what kind of a role does work play in your life? And how do you find balance with that?

Karen: That’s a good question. I’ve always described my work-life balance as being a very porous balance. So, to me it seems like a luxury to not have to have particularly well-defined boundaries between work and life. Those should just seem like the same thing, and then you don’t have to worry about drawing a hard boundary between the two.

And I know plenty of other people who take a very different approach to that where they like to have very clearly-defined, I’m doing this at this time and that at a different time. But for me it seems like a better balance is just to say, what do I feel like doing today? And some days I’m deeply engaged with my work and I feel lucky to get to say that. And other days if I want to take a Wednesday and go do something else I’m perfectly free to do so. It’s a nice balance.

Paul: That’s pretty cool. I’m curious, too. How do you get things done, then, when you have that type of fluidity with it? Because I feel that if I were in that situation I’d be really tempted to do things on Wednesdays and then maybe Thursdays, too.

Karen: You know, people say that to me all the time. And part of me wants to be like, no you wouldn’t.

Paul: OK.

Karen: It’s just like there’s enough, I don’t know, social pressure, enough - I mean, maybe I’m just - maybe one of my problems is that I’m just an anxious person at heart. But there’s always a certain sense of, oh, I’ve got to get up. I’ve got to do something. I’ve got to make something happen. I traveled 170 days last year.

Paul: Oh, wow.

Whitney: Whoa.

Karen: I know. I’m not doing that again this year. And so, come January I had pretty much what was going to be the longest uninterrupted stretch of time. I was going to be in New York for, seriously, years. I had three straight months with the exception of one tiny little trip to Tokyo. But that was not a big deal. It was just like one week.

Whitney: Only the other side of the world.

Karen: Only one trip to Tokyo, though. And so I had like three months where I was here in New York. And I totally went into it like, yes, I’m going to relax and it’s going to be glorious. And two days into it I was like I need a project. What am I going to do? I have to repaint my apartment. I have to rearrange my apartment. I have to buy new furniture and new artwork.

I think there’s just this deep-seeded sense of I want to do things. And whether those things are professional or whether those are personal objectives doesn’t - to me, categorizing them doesn’t make any sense. I also have never understood people who maintain a budget by categorizing what their expenses go to. Like, I’ve heard people say things like, well, I don’t have any money this month to go out for more restaurant meals. But I do have money to buy - I can go to a movie. What kind of sense does that make?

So I kind of feel the same way about work and life. It’s like you have things you want to do, and some of them make you money and some don’t. And you should make sure you make money, and the rest of the time have fun.

Paul: Wow, that sounds really simple. I like that a lot. I love it.

Whitney: So, it seems like you like to take action. You don’t just like to sit around and think. But when you’re in motion, when you’re doing stuff, is when you’re most satisfied. So, is that the case?

Karen: You know, I might even say there are - I definitely like to have projects where the project is go think about this thing. Like, right now I have - I’ve been really deeply kind of poking at this problem like how do you separate content from form, or what does that mean? What are all the different dimensions of that?

And lately I’ve been having so many interesting conversations with people about that. I’m lucky enough to be working with Ethan Marcotte right now, and he and I have had many interesting discussions about that. My friend Jeff Eaton and I, we could pretty much spend our entire lives debating that subject. And I’ve been thinking about it so much that I just said to them recently, I’m like what if I were to make some slides that I was just going to show you? And I would like - where we could have a conversation where we might be able to discuss some specific examples and kind of noodle on things.

And those kind of - that kind of like taking action or thinking about things, there’s not a very clear boundary to that either. I spent a lot of time kind of running over things in my mind. And sometimes I take notes about it. And sometimes there’s some benefit to being like, you know what? If I made that tangible in a slide, that might help. But I don’t know if I make a firm boundary there between what’s action and what’s not action.

Whitney: Yeah, I get that. But it sounds like even your version of thinking is concerted effort. I mean, I hear you saying I’m going to take these notes. I’m going to create this deck. Even if it’s not necessarily for public consumption, it sounds like there is a concerted effort behind what you are involving yourself in. I’m trying to look for a word that isn’t work, what you’re working on. It does sound like effort is involved.

Karen: I like to poke at things, you know? I like to - or I like to turn things over in my mind. And that isn’t - yeah, I think you’re probably right. I think the idea of there being some purposeful effort, like I would like to go deeper into this subject, that seems very real.

Whitney: Yeah. So, with all of this freedom that you seem to have, and ability to decide how you spend your time, how do you decide what to work on, where you spend the effort and where you don’t?

Karen: I think it’s like I have a steady stream of clients coming in. And that doesn’t seem to be something that changes all that much, although if it were to change I might step up my efforts to market myself or try to get new clients. But the client work fills a certain amount of time, and then the remaining projects fill the rest of it.

That’s not a very good answer, but it seems like the client stuff will take up - it could take up all of my time. But if I manage things well enough and don’t take on every single thing that comes my way I manage to keep it about 75% of my available effort. And then the other 25% goes to other things I want to do.

Whitney: And how do you decide which of those projects that come your way are worth your time?

Karen: I like all my projects. That’s the problem. I never - it’s rare that something comes my way that I don’t see some engagement in. Lately, I feel like lately I am a great testament to the power of more focus actually providing more opportunities rather than fewer. So, it’s like I’m a UX generalist. Jared Spool introduced me, or Leslie Jensen-Inman introduced me at Jared Spool’s latest conference as like this woman’s a true UX unicorn. And I’m like, thanks for that. Thanks, Leslie.

But it’s like I can do - I have credible experience in a wide variety of UX-related tasks. And lately I have been doing nothing that isn’t just like squarely laser-focused on how do you get your content and your organization ready for true digital multi-channel publishing? Like, how do you support getting your stuff onto the Web and all of these different devices and platforms?

And that’s a pretty tight niche, but you know what? It’s sort of like in that tight niche I’m it. And so, when organizations sort of recognize, like, we have this problem, I’m the person they come to as opposed to a more general point of view around, well, I could do everything. And if you do everything you’ve got a lot of competitors.

Whitney: That’s a great point. And so, how did you hone in on that laser focus of what your specialization would be?

Karen: You know, I told this story at the IA Summit last year. I was working with my friend Jeff Eaton. And we were jointly writing a presentation for this conference where the theme was going mobile. And I remember him looking at me and saying, wow, this would be a lot easier if either one of us knew anything about mobile.

And, he was trying to explain to me, because he’s a big Drupal guy. And so he was trying to explain this idea of how a content management system and an API - you could stick an API like a straw into that CMS and then use it to suck out the content. And then that API could be used to publish to other platforms.

And I just remember not getting it, like I felt so dumb. And I just felt like - I mean, I just remember having this moment of being like, mobile, not for me. Let’s let somebody else figure this out. I like the Web. I’m good at the Web. I get how the Web works. Let some other kid figure out all this mobile publishing nonsense.

And I had this real - I had this just absolute, deep flash of insight. I mean, I remember it, where I was like, wait a minute. I get this stuff. I mean, I really do. I grok this stuff, like in my bones. And it’s like if I feel this stupid and this out of my league and this clueless about how this should work, think about how everybody else feels.

And I don’t mean that to be self-aggrandizing. I just mean it like, well, if I feel dumb everybody else must be really having a hard time with this. And it just gave me such a real flash of compassion, like how much fear and this real worry that people were going to do the wrong thing and they were going to be embarrassed and they were going to make a bad mobile website and it was going to suck and they’d get fired and their coworkers would think they were an idiot.

And it just left me with the sense of, like, oh. Well, I can explain this. And that’s where the book came out of. And that’s how I wound up doing what I’m doing. And I honestly think I’m doing the best work of my life because it’s sort of rooted in this feeling of like it’s not that you’re an idiot. It’s not that you don’t get it. It’s that this stuff is hard. And I get why you don’t want to make a mistake.

Paul: I mean, that’s an extremely compassionate way to approach it as well versus saying I know this stuff and I’m it and that’s it and saying that nobody else can ever get this and just being open to that possibility of other people saying, yeah, I don’t get this but I want to understand it and I need somebody to help. And it sounds like you’ve been there, and that’s pretty incredible.

Karen: Well, I think the luxury that I hope everyone has the chance to experience, especially as they kind of mature in their career, is that ability of feeling like an idiot, feeling like you’re out of your league, feeling like, you know - I think the sense of, like, oh, wait, has the internet passed me by? Have I lost the thread?

And then the feeling of being able to grab that thread again and say, oh, no, instead I have my five years, 10 years, 15 years of experience behind me, and I’m going to be able to bring that insight to whatever new thing it is I’m trying to learn. I mean, to me it’s like that should be your career, is like an ever-widening succession of, like, I’ve learned this thing. Oh, wait. There’s this new thing. I don’t get it. Oh, wait. I’m going to grab onto that and I’m going to bring what else I’ve learned to it.

Paul: So, as you’re navigating all those things, how do you figure out what really means the most to you? How does that work? I’m very curious about that from your perspective especially because now you’ve mentioned how this whole idea of content strategy for mobile came about, essentially. Where do you find that meaning?

Karen: I’m big on intuition. I’m just big on - I feel like the times in my life when I’ve just sort of been able to tune into whatever my gut instinct is are the times when I’ve been happiest. And that’s hard. I mean, that’s a terrible answer to your question because it’s not going to help anybody answer that for themselves.

But I can say the times in my life when I’ve been able to just pick up on sort of a general vibe, like, hmm, this is interesting to me, I should explore it more, those times turn out well. And the times when I have a gut feeling of, this is not going to go well, the times when I ignore that feeling are the worst times in my life.

Paul: So where do you think that comes from?

Karen: Where does intuition come from? You know, I guess it’s like I’m a big Jungian. And I guess that intuition versus sensing dichotomy is - it seems like one of those fundamental things. Like, some people only trust the information that they can get from their five senses and they can prove in some sense, and some people have a sixth sense that they just rely on even more.

And it’s easy to - I guess it’s like it’s easier to discount the intuition. But the truth is it’s pretty easy to discount your senses, too, if you spend any time thinking about it.

Paul: Absolutely.

Whitney: Which is something that we talk a bit about quite a bit on this show, the intelligences that live outside of our brain. And I think that’s what you’re saying. I hear you say gut instinct and intuition as though they are these other intelligences that exist within our body that we just have to learn how to tune into.

Karen: Yep, absolutely.

Whitney: So, how would you say, then, that these senses, or your sensibility, guides you as you go throughout a project? How are you able to determine how to vary your effort at the beginning, the middle and the end of a project using the intuition that you describe?

Karen: I think that probably the number one sense that that can give you is if you have a bad feeling about your initial interactions with people or - it’s like if I’m entering into a client relationship or somebody contacts me like, hey, you want to work on this? And I don’t have a good feeling about it, I should probably listen to that feeling.

And the biggest regrets that I have of projects that went horribly off the rails or clients that just genuinely treated me badly, pretty much I can always turn them - I can always follow that thread back to my initial gut feeling of, like, that’s not going to work out. It rarely works out differently.

Whitney: I’ve had the same experience.

Paul: Absolutely.

Karen: It’s like, so I teach a design management class at SVA. And a lot of the students there are - they’re doing freelance work. They’re just kind of starting out running their projects. And we talk a lot about contracts and how to protect yourself and just sort of all of the operational machinations that go into running a business.

And the truth is none of that means anything. I mean, yeah, of course you should write a contract. But you know what that contract is? It’s a conversation. It’s a discussion between you and another human being or a bunch of human beings about what you’re going to do. And at the scale that most of us are operating on you’re never going to sue the client. You don’t have enough money to sue. How much are court costs? The scale of what you’re doing is probably not ever going to be enough for you to take on any business, certainly not a large corporation.

And that’s not to say you shouldn’t have a contract. But it’s that the larger picture there is really as those negotiations take place, as you discuss the contract, as you have the conversations about what you’re going to do, do you feel good about that? Are you getting a vibe there that that person is fair and reasonable and wants to treat you fairly? If that’s the case, then you’re fine. Then you’re going to deal with the problem as human beings.

And the situations where I have felt like this person is sitting on the other side of the table with me and they’re just looking for ways to screw me over - you know, they’re just getting their chess pieces aligned so that they can eventually screw me over someday if they need to - that’s not a relationship you want to get into, you know?

Whitney: Absolutely.

Karen: And the truth is, the contract doesn’t protect you from that. The truth is that it’s only your - the time that you spend kind of learning to trust your instincts there, that’s what pays off.

Whitney: And so, what I’m hearing you say is that for the most part you sense early on in that relationship, through the initial conversations when they first reach out to you, perhaps, through the contract negotiation process, who you’re dealing with across the table from you? So you know now from your experience not to get yourself in situations with people that your gut instinct is saying don’t trust this person.

But let’s say you do get yourself involved and you have a notion of what the effort is going to require. And how then does that change over the course of the project? I guess what I’m wondering is, you talk a lot about the sense that you have in the beginning. But what do you do to tune into how things are changing and perhaps reassessing what’s really required of you as the project progresses?

Karen: That’s an excellent question. And I think the more true independent consulting I do, like strategic consulting I do, the more that becomes the real name of the game. Like, they’re hiring you to, you want to say, achieve an objective. But in many cases it’s looser than that. In many cases they don’t actually know what they want. And they’re somehow looking to you to shape it. And they may not even be able to describe what’s going to happen.

And it really does involve a certain amount of, I think, awareness of what the group dynamics are like, what the organizational dynamics are like. And I will admit, it’s hard because in a lot of cases, especially coming at it as an independent consultant, you’re not - you’re almost like not invited into those conversations unless you figure out how you’re going to get yourself in there. It’s like layers upon layers upon layers of trying to navigate an organizational hierarchy.

And, you know, in those cases I think they have to want you there. And somebody’s got to really want you there. And I have found situations where I have a stakeholder, an executive sponsor, who really understands what I’m doing and why I’m there and is willing to partner on helping me navigate the organizational hierarchy or helping me figure out, OK, what should I be doing here? That goes a long way.

And situations where I don’t have that or - sometimes people will bring me in like I’m a magic wand, right, like I’m pixie dust that they can sprinkle on the situation and that’s going to make everything magically better. And I wish I was that, but I’ve got to tell you if I was that I wouldn’t be helping your publishing site get better. I’d be off being pixie dust doing something amazing.

Whitney: And charging a lot more.

Karen: Right, exactly. If I were magic, I would charge a lot more. So, there’s plenty of situations where it’s like, great. I got hired to do this project. And then you just start to realize, oh, there’s like walls upon walls here. And how much do you want to navigate that situation? I mean, I think a better question is like what’s the effort-reward balance?

There are certain situations where it’s like, oh, you know, I could have wormed my way into that organization if I made it my sole goal in life to, I don’t know, suck up to people and sit with them and figure out what was going on. But in some cases I’m like I just want to come in here and solve your problems. Then I want to go away.

Or not solve your problems, but it’s like I want to come in here. I want us to work together on a specific, defined problem. And then if you want to continue working with me, great. But I’m not just going to hang around.

Whitney: So, ultimately it’s about determining for yourself what you’re looking to get out of it and then sensing your way through whether that’s going to be possible? And it sounds to me like you’re willing to up the effort to the extent that you can bring greater assurance that you will achieve what you set out to achieve. But if you sense that that’s not going to be the case, then what’s the point of the added effort?

Karen: Exactly, yeah. I have some projects that there’s a real sense of like, oh, I can help you guys out a lot. You are - and what the combination of things is, it’s like the right balance of my skills, the right balance of your needs, the right balance of where you’re at as an organization sort of comes together to be like, oh, OK, you guys are willing and ready and this is a thing that I know how to do.

And there’s other situations where either - I’ve had situations where it’s like I got brought in, and I wasn’t doing anything that the team couldn’t have done themselves. Some executive brought me in to be like, well, she knows everything, so let’s hire her. And in those situations it’s like it’s almost better to be like, no, you guys, you got this. Go to town. You're great. I love you. I’m going to back slowly towards the door here because there’s no reason for me to be here.

And I don’t see that as a problem. I see that as, in fact, the same sort of benefit where it’s like, let’s - we all have limited resources here, so why don’t you guys spend your limited resources on things that you don’t have as opposed to what you already do have. And why don’t I spend my limited resources working with people who need me?

Paul: Yeah.

Whitney: Right. That’s great.

Paul: So, we’ve been talking a little about this internal and external dynamic. And that was something that was a part of our Dare talk last year. I am very curious how that talk came about.

Karen: Yes. That talk, so Jonathan Kahn, who’s a friend of mine, and he told me he was going to organize this event called Dare to help people be brave together. And he asked me to keynote it, and it was one of those things where I was like, I know what you want here, Jonathan. I know exactly what you’re going for.

You’re - it’s like this kind of stuff, it’s like this is who I am. And I was really flattered but also, in a sense, very grateful that he offered me the opportunity to keynote that, because I’m like, OK. This is my shtick. This is what I am. And so, I wrote that talk. It was obviously very, very personal talk and very much came out of the experiences that I’ve had over the last couple of years.

And I was very badly betrayed by a couple of people who I loved and trusted and who deeply, deeply wounded me. And as a result it has kind of forced me to, I don’t know, just like reexamine a huge swath of my life. I got into really hardcore Jungian psychoanalysis, and it has enabled to me to kind of see things in a little bit different perspective. And I’m grateful for it, in a sense.

And so that talk was like I sat down and I’m like, OK, let me just write this thing. And I say it’s like I really wrote that talk for a very intimate, very personal stage that Dare offered. And I did not expect that talk to be all over the entire internet.

Paul: Oh, wow.

Karen: I know. I had no idea. And so, it was one of those things where I’m like, well, I guess I’ll just embrace this as one of those random things that happens to you in life. But, no, if I had known then what I know now about where that talk would go, I don’t know if I would have written the same thing.

And frankly I’m grateful. It’s like I’m lucky, in fact, that I had a chance to be very honest and very personal like that and to see the effect that it’s had on people, because I’ve had so many really warm and heartfelt exchanges with people about it. And that’s actually meant a lot to me. I should say it’s meant way more to me than all the other stuff I’ve done.

Paul: Wow. That’s incredible.

Whitney: Wow. And it’s almost a blessing in disguise that it had the reach that it does because, as you said, had you known, you may not have shared to the extent that you did.

Karen: Oh God, no.

Whitney: But your not knowing allowed you to be really raw and personal and touch such a huge audience of people who may never have benefited from seeing you in that light and recognizing that they have gone through similar things and that they’re not alone in that. So it sounds to me like being brave together you achieved spot-on just through your own self-analysis and willingness to share yourself with others.

Karen: You know, it’s like - yeah, that’s a really nice way to put it. That’s exactly how I would describe it. It’s like I never would have been that brave if I had known what would happen. But the intimacy and the warmth that that Dare conference has really gave me a really safe space to feel like I could be honest and feel like I could share in a way that - yeah, it’s like everybody has stuff.

I mean, none of us get through this life without that, you know? And it’s just so - the thing, honestly, that has meant the most to me is being able to connect with other people who have now felt comfortable to reach out to me and say, oh, I had no idea that you had things like that happening. And I laugh and I’m like, well, of course. I mean, yes, of course. It sucked, and I cried.

If something like that is happening to you, I hope that you would feel comfortable talking to me about it, because we’re all in this together.

Paul: It is. So, one last thing about that, too. I’m curious. Where do you think that idea comes from, that whole idea of the kind of surprise that people have when you’re sharing that type of thing? Because I can say that was a little bit of my experience, too, honestly, watching it.

Now, I knew, of course, it’s like, yes, I know Karen McGrane is a human being and she’s got things. And I’ve got things, too. It makes sense logically, right? But when I watched it I was - my reaction was very much like, wow. This is incredibly brave. This is a lot of stuff for her to share. So, how do you deal with that reaction? How does that work for you?

Karen: Well, I think I might say that I probably don’t have a reputation as being an over-sharer. So I think there’s this sense of people maintain a public persona, and they want to make it seem like everything is great and perfect and I am fantastic and my life is wonderful all the time, and aren’t I shiny?

And the sense that you might be able to chip away at that a little bit, you know, I’ll admit it’s like of course. I want you think I’m great. I want you to think that I have my shit together and that I’m like my business is successful and my relationships are amazing and that my life is wonderful all the time. And so, the willingness for people who maybe have done a good job of that to chip away at that a little bit, I think, just provides some balance.

And it’s like if that’s all I did, you probably wouldn’t like that either. It’s like if all I did was complain about how terrible things were I don’t think they’d be letting me give a keynote at that event. So I guess there’s just some balance in being able to say, yes, it is possible to be successful. And it is also possible even if you are successful, to deal with the same problems that everybody else has. And nobody’s free of it.

Paul: Wow. That absolutely makes sense, and it’s reassuring to hear, honestly. It totally is. Karen, thank you so much for your time today. This has been a fantastic conversation. And we’re honored that you decided to join us today.

Karen: You guys are great. I’m really honored that you invited me.

Paul: Thanks so much.

Whitney: Thank you.

Whitney: Designing Yourself is hosted by Whitney Hess and Paul McAleer and is edited by Aaron Dowd. Our theme music is “All Heroes” by Ardecan Music Productions with some rights reserved via creative commons. You can follow Whitney on Twitter at @whitneyhess. And you can follow Paul at @paulmcaleer.

Paul: If you like what you heard on this episode, stop by our website at DesigningYourself.net. You can subscribe to the show via your favorite podcasting app or via iTunes. We love to hear your feedback. So if you have an idea for a topic, a guest, or just want to say hello, you can call our listener hotline. Call 1-404-500-SELF. You can always reach us on Twitter at @designingyou, and our super-secret email address is designingyourself@gmail.com. Thank you for listening. We’ll talk again soon.