On being honest about what you have the time to do

The first time I emailed you, I got an automatic response saying something like, “I check email three times each day in order to maintain some level of sanity.” How did you come up with that idea, and has that worked? I’m curious how you manage to balance all the things you do.

It hasn’t worked as well as it looks. I’ve been incredibly lucky in that the fallout from my failures has not been huge. But I’ve had major failures based on an inability to either say “no” or “I need a break” or “I need a pause,” or to just give some indication that I was floundering and that I was not doing okay.

That note you mention—when people would get that bounce-back from my email—was written during a sort of desperate moment. It was this huge assertion for me. From the beginning, when someone would first email me, I needed them to be working under the assumption that there is a good chance my answer will be “no.” I get the opportunity to do so many cool things that I never, in a million years, thought I would get the opportunity to do. I found that nothing really prepares you for having to say “no” to things you actually want to do.

So I put up this thing on my email saying I’m only going to check my email three times a day at these times—and I never stuck to it, ever [laughs]. I was always checking it all the time. It was really just to manage an expectation, and I eventually ended up taking it off because I realized it wasn’t really helping me. Plus, it was clogging other people’s inboxes when we would have a back and forth conversation. So it was just like, “You know what, this is no longer worth it”… and I hired an assistant [laughs].

When I got that email, though, I thought, “Wow, this person is so well organized.” It’s definitely a good strategy for managing expectations.

Absolutely. Wanting to say “yes” to too many things is a product of being so many things, one of them being a woman. We’re conditioned to make sure people feel flattered; to make sure people feel that when they come to you and talk to you, they will not have to deal with anything too uncomfortable. I am also Midwestern. I’m from the land of polite apologies and niceness, above everything. On top of all that, it was really hard to believe you can become overwhelmed by doing something you like to do.

I love to write. The only thing I’ve maybe loved longer than writing is my brother, who is 14 months younger than me. I love writing, and I think when I started writing and I started getting certain opportunities that I never thought would be possible for me, I was trying really hard to rise to the occasion. I didn’t understand that learning to say no was part of rising to the occasion, and I was letting people down. People who I cared about, people who I loved. I was letting people down a lot.

Then I would feel terrible about myself; and the worse I felt about myself, the harder it was to write, and the more people I let down. I found myself in this internal struggle and spiral towards burn-out, towards a place where you’ve ruined everything. You’ve ruined your reputation. You’ve ruined your relationships. The only person who could’ve stopped it at any point was me. When I realized I was getting to that point, I put a vacation responder on my email, and I hoped that it would manage expectations. I also hoped that having that be the first interaction with people who emailed me would allow me then to feel a certain strength that I didn’t always feel in the moment.

I feel like when you put a message like that out, it immediately presents a certain strength—a confidence that you had when you wrote it. So, I knew that that version of me was always going out ahead of me, and knowing that that was happening allowed me then, when somebody emailed me, to say, “I’m sorry. I don’t have the bandwidth for this,” or “This is a really amazing opportunity. I really hope you’ll keep me in mind for something in the future, but if I do this I want to do it 100% and there’s no way I would be able to give you 100% right now.” Being able to say things like that three years ago, four years ago, would have saved me a lot of pain and anguish, and would’ve saved a lot of other people a lot of frustration.

I really do try not to take myself too seriously. I know I just gave some talk about how I had to dig into myself and figure out how to say “no” to all these amazing opportunities, but I can’t take myself so seriously that this thing I love becomes my burden. This thing I love has brought so much good into my life and I want to honor it. I think honoring it means following my curiosity and always trying to be a better writer and not looking down my nose at any publication or any writing opportunity where I get to do something I’ve never done before, or I get to learn something from someplace where I know they have something there I want to learn.

Everything I do is a learning opportunity. That’s what I want. I want everything I write to be in practice towards getting a little bit better and a little bit better and a little bit better, and honoring the gift of being able to do this work.

Do you see the creative things you do as part of the same overall practice, or do you find yourself privileging any parts of it?

I think writing is always going to be number one for me, just because that’s the thing that feeds my spirit the most. But, I feel like all the work I do is in service to this greater curiosity that I have, this fascination about people, the things that we do, and the things that are important to us. I did this branded podcast not too long ago with MasterCard called Fortune Favors the Bold, and I was really nervous about it at first. I was like, “A branded podcast by MasterCard? Am I selling out? Is this selling out?”

But I realized that I would have done it even if it were not branded by MasterCard, because I’m fascinated by money, and I like talking about money, and I like talking about the future of work. Those are really fascinating subjects to me. I’ve written about them. I’ve done interviews about them. I talk about them quite a bit in some of these public things that I do. But when I was doing that podcast I kept checking in with myself and thinking, “Would I say this and would I do this if it wasn’t branded? Would all this still be what I wanted to talk about, and would this still be how I wanted to talk about it?” The answer was “yes.” So that felt okay to me.

Now, there have absolutely been times when people have reached out to me with opportunities to do things that did not feel okay to me, so I really trust my gut on stuff like that. I don’t do it. It’s also just really weird to be at this intersection of pursuits. I am a writer, but I also give readings, and I host a podcast, and I write in different spaces and in different areas. I end up getting lumped in a lot with the idea of an “influencer,” like a brand influencer, and I don’t really think of myself that way. Not because I think there’s anything wrong with that work. I just don’t think I do that work.

You’re working on a memoir,Somebody’s Daughter. Do you find the time to work on the book every day in addition to the other things you’re doing? You have a steady Twitter presence, too.

Sometimes I do better than other times. There are times when I’m like, “You know what? I need to be in creative mode versus consumption mode.” During those times, I’m really not on Twitter or Facebook or Instagram. I have my moments of going dark; and then, at other times, it’s like I’m on here constantly and it’s probably a problem. And I’m like, “I gotta get out of here; I can’t get stuck in this,” because it is easy to get stuck in this. It helps to essentially have a luddite for a partner who changes my social media passwords and then, at least a couple of times, loses them.

He changes them and he keeps them and then I can’t get on for a while, and that helps me hit a healthy reset so I can get back to incorporating social media into my life. Because it’s important to me, but so is making sure it’s healthy and that I’m not getting sucked into some sort of Matrix-y experience, because that’s what he sees when he looks at me using something like TweetDeck.

I realized not too long ago, that for me it really is all about balance, but the balance isn’t between a good activity and a bad activity, or stuff like that. It’s more like you’re trying to find a balance between freedom and responsibility. So, essentially everything that I do is trying to be a little more free. Being able to do whatever I want to do.

I really like being able to do whatever I want to do. But you have to take responsibility for what freedom means. So, if I want more freedom, then that means I am also constantly responsible for making sure everybody else gets closer to having more freedom, and I have to be doing both at the same time, all the time.

Even with that finance podcast I mentioned, I’m doing this podcast because I know that there are people who will listen to this podcast just because I’m the host of it, and they are going to learn something important about their economic future. So it’s like, yes I get to do this thing I want to do, but also here’s a social benefit. I like things with a social benefit, and if I can’t find a social benefit in something that I’m taking on project-wise, then it’s just hard for me to stay interested.

When you’re not working, how do you nurture your creative side? Do you ever just take a break to catch up on reading or something?

I’m trying to do more of that. My fiancé helps. We just did a weekend upstate and stayed in a guest house out on somebody’s land, which was nice. But we’ve lived here for four years and that’s the only time we’ve ever done that. I’m trying to get better about it. I’m not good at taking breaks. I love projects, and I like to go from project to project to project to project to project to project. That’s how my brain works. That’s what I like to do.

I like to get consumed by a thing, but the projects often overlap, which I also love. I thrive in that, but—and here’s the but—there’s always limits to that stuff. I’m so much better at this now, thank god, but I have to figure out how much a project will actually require of me in terms of time, and different kinds of time. If something requires me to travel, that’s still time, but it’s not active time, and it’s time that I could be doing something else simultaneously. But, do I want to do that? Am I in the right frame of mind to do that? The thing that I would fit in there to multitask, is that a thing that I really want to be working on during layovers in airports, or in hotels while I’m waiting to do an interview?

It’s always weighing and prioritizing, and it’s really hard to streamline things about my life. I’m always weighing and prioritizing the next thing, or what I can work on at the same time. Right now I’m weighing these things really carefully. I’m trying to get that balance between freedom and responsibility. In order to do that, I have to say “no,” and I have to back up, but it’s tough. It’s really, really tough to juggle. I will never say that it’s easy, and I will never, ever, ever say here are five tips to make sure that you can do it. It’s just not that easy when you do creative things and your brain happens to work like mine.

Are you okay with abandoning a project?

I often feel like it wastes less time to just back out and say, “I’m sorry, this isn’t going to work.” That is always better than being silent, which I have done, and it was terrible. It’s terrible for the other person and it’s terrible for you. When you just disappear because you don’t know how to say, “Oh lord, I don’t have this in me. I can’t do this, or I’m finding this terrible to try to do.” It sucks. Sometimes you’ll try and back out and the other person will say, “Well, what if we did this to make it easier for you or something, or what if we adjusted it this way, then would it work?” And sometimes you’re like, “Oh, that will work, actually.” Sometimes yes, you have the ability, but it’s not what’s right for you to do right now because it will overwhelm you, and then it will ultimately not be worth it because of how bad it made you feel.

I used to be like that. Those things used to make me feel so bad that it started getting to a point where I couldn’t write. I would go to write something and I would already be anxious because it was overdue or it was behind or there was no way it was going to be as good as I wanted it to be because I was only just getting to it the day before, and how did this happen? It’s the worst. Just let people know what’s going on with you. Just have the conversation. Learn from my mistakes. Don’t do it to yourself.

I agree. Something I’ve learned as an editor over the years: It’s always best if the writer is honest. If someone keeps saying, “Oh yeah, don’t worry, I’ll get this to you,” then keeps pushing it back, it throws a wrench into everything. It’s so much better for the person just to say, “Hey, this is actually too much right now.” Be honest—it’s so much easier on everyone.

It really is, but people are terrified. They’re terrified to say they’re overwhelmed. They’re terrified to say, “Actually this took more time than I thought it would, and now I’m behind,” or “The flight was delayed,” or whatever.

Unfortunately, people with a poor work ethic who constantly make excuses, have made it impossible for people who truly struggle to feel empowered enough to say “I’m struggling,” because struggling sounds like laziness to a lot of people, and a lot of people react to it like laziness.

I have anxiety. I have a lot of stuff going on all the time. I’ve learned that I wanted to get better at juggling things, but I had to let people help me. I had to set up systems, and I had to figure those things out, because I didn’t want to be that thorn in somebody else’s side, to be perfectly honest. I have a lot of things going on, and I’m busy, and that’s okay. I like being busy. I don’t complain about being busy because I actually really do like it, but there was a time I was just not prepared to be a busy person. I didn’t have the help I needed. I didn’t have the systems I needed. I wasn’t ready for it, and I had to make sure that was in place before I allowed myself to get busy again.

Productivity is not peace. You’re never going to do enough for the doing to bring you peace. That’s just not how we actually work, but that is how our society tells us we work, and it is really hard to break out of that mode. It’s really, really, really, really hard, but I’m doing my best all the time, man.