“Hope is not a plan:” How to manage ADHD at work

ADHD can create all kinds of challenges in the workplace. Like a list of infinite things to do and to remember. A busy, ever-changing schedule. And co-workers who don’t always know what’s going on in your mind. 

There’s a lot to figure out. But recently, Rae Jacobson found herself wondering what it’s like on the other side — to manage someone who’s neurodivergent and still figuring it out. 

So, Rae called her former boss, Caroline Miller, the editorial director of the Child Mind Institute. 

On this episode of Hyperfocus, Rae and Caroline go over this question and Caroline shares some advice on ADHD at work — for employees and managers alike. 

We love hearing from our listeners. Email us at hyperfocus@understood.org.

Related resources

• “Masking my ADHD at work was exhausting, so I stopped”

• Workplace supports: A guide for employees 

• 3 big myths (and truths) about workplace accommodations

• How to ask for a workplace accommodation 

Timestamps

(03:49) Caroline’s first thoughts on working with Rae

(09:16) Neurodiversity initiatives: Trends vs. real support

(17:04) “Hope is not a plan”

(22:05) Caroline’s keys for hiring 

Episode transcript

Rae: Caroline Miller is the kind of person you want to impress. She's the former editor-in-chief of New York Magazine and Seventeen, she's the editorial director of The Child Mind Institute. She teaches journalism at NYU. She started entire magazines from scratch and she raised three kids. And she was also my boss and my first-ever office job.

People throw the term imposter syndrome around, that creeping sense that you're not really the capable, responsible adult you're pretending to be, that you're just faking it, bound to be found out, because how long can this charade really last?

Everyone feels it sometimes, but for the most part, it passes. You settle in, pick up the rhythm of the job, you shake off the doubts, and get to work. Or that's what I assume happens anyway because for me and for a lot of people with ADHD, that's not always how the story goes.

My early retail or service industry jobs regularly found me scrambling to be on time, trying to remember what the tasks were, and how to do them. Trying and failing to work cash registers, count money, remember the code for the lock, or even if I'd remember to lock up at all.

Later, as a freelancer, I was spared the stress of showing up on time but pulled endless all-nighters like the college kid I no longer was. Deadlines looming, unsent emails nibbling at the edges of my brain. Like with school, I'd start strong, slip on my own lack of executive functioning skills, and skid right into failure. Let's fake it till you make it more fake it until you can't. Until I met Caroline.

Caroline hired me as a writer, something I could do. And when things started to go off the rails, instead of saying, "Here's the door," she said, "Here's what you need to know." What she taught me was something I hadn't known you could learn, what to do when the road runs out, how to stop the slip, find your feet, and actually succeed.

I don't work for Caroline anymore, but over the years, I've wondered what it was like from her perspective. Working with people like me, people who are neurodivergent and still figuring it out. So, I asked. And as ever, she had some very good answers. I'm Rae Jacobson and this is "Hyperfocus." Today on the show, my old boss, Caroline Miller.

Caroline: You know, I hired you for a couple of different reasons. One thing was that I knew you were a good writer because you had writing experience and I'd read it. And I knew you were a very smart person. And I knew you had this experience and I thought, "Here's somebody who is going to be able to write about this with authenticity and without being condescending or offensive in any way."

I mean, I just thought it was going to be great and it was, you know. So, I think we were able to write about this at a time when there was very little writing about girls, women with ADHD. There's a lot more now.

Rae: There's a lot more now. But, you know, if you ask me, it's still not enough. But it's true. It was a new thing then, and I remember being so proud to put that stuff out and so excited that I was allowed to do it. I also remember that when I started, I didn't fill out any of my HR paperwork for six months. They sent you a lot of emails about it.

Caroline: It's a good thing you were there earlier because as the organization has grown, it's become much more formal and you wouldn't have made it past the first day now without filling out all the paperwork. It's true. And, you know, so, some people are more tolerant of that kind of thing. And I'm not a particularly bureaucratic type of person, so it didn't bother me.

(03:49) Caroline's first thoughts on working with Rae

But, you know, you taught me a lot that I would not have learned about how to deal with somebody with ADHD. And, you know, and I think it would be useful for a lot of people, for instance, people with ADHD. But I'm thinking of you in particular, never did things in the time frame and in the pacing that I would have done them or that I would have anticipated.

Rae: Yeah.

Caroline: So, you know, be prepared for the fact that you'll think nothing is getting done. It's not getting done. It's not getting done. I don't see anything getting done. And then it gets done in a very short, very intense, very focused period of time. And and it's amazing. And it's as if it has to be done kind of all in one. I don't know how, what the right word would be, but, you know, it comes that whole.

Rae: Burst of stress?

Caroline: Yeah. But I just, I remember learning that if you think it's going to get done today, that might not necessarily be the case, but it will get done and it will be good when it's done. And so, you have to have, you have to be a little bit more flexible about...and I've worked with people in the magazines who were like that.

I had an art director once who just tortured us because it seemed like he wasn't laying the magazine out. It wasn't getting done, it wasn't getting done. And then you'd come in and the whole thing was done, you know? And I think he probably needed that, you know, that stress.

Rae: The panic motivation to get it going. I, you know, I wonder about that, too, because, you know, we talked when we were working together, so much about ADHD. And we had another co-worker, the wonderful Rachel, who did not have ADHD and was fantastic as a human and also fantastically efficient. And I remember working next to her and thinking like how different we were.

And we both had different skills, but like, you know, you had two people who are completely different in the way that we operated. And you've managed so many people over the years, I know. And, you know, you must have seen a million different styles of working. And now knowing what ADHD looks like at work, I imagine you could look back and be like, "Oh, that person probably had it."

Caroline: Absolutely.

Rae: But, you know, how do you keep a team together with people who have such different skill sets? Like you were so good at that.

Caroline: Well, when you know, when you say you worked next to Rachel, it would be accurate to say that we all work together. But you never were sitting next to Rachel. And this is another thing that I would say that if you have somebody really has ADHD, don't expect to see them in their seat. You know.

Rae: It's true.

Caroline: Rae had a desk.

Rae: I did have one.

Caroline: She was never in it. And so, she would be working somewhere. I knew she was there, but she would always be kind of, you know, secluded somewhere or found a quiet corner or, you know, something that just made it work, right? Something about, and I wouldn't be able to project that you could sit here, but you wouldn't want to sit there. It was just kind of you had to get comfortable somewhere and be able to tune out all the other people.

Rae: That's so true. I kind of forgot about that. Even in my current office where I'm sitting right now, I'll go and work in like this stairwell sometimes. But, you know, it's just where you find yourself. It's what works. But you were never like, "Why aren't you at your desk?" And I made it so that I could do that. And I wasn't like concerned or having to fit in and try to work while I was like, distracted.

Caroline: Well, and partly because — and I think other people, I'm sure, have observed this same kind of thing, and I don't just mean about you — but you would just be acutely uncomfortable. And it was physical and it was and it was obvious, you know, sort of squirming.

Rae: Yeah.

Caroline: And so I, you know, I could tell that it wasn't really very effective. So, it was interesting to me to see how you got things done.

Rae: No, yeah, it's one of the things now, it's like I think post-pandemic, it's a lot more accepted that people need flexible working situations or some people work from home part of the time or all the time or whatever it is. And you know, now it's in the public consciousness. But then it really was something that was pretty unusual. Like I remember kind of like sneaking around the office with my little lamp that I had that I liked and like plugging it in under a table or something.

Caroline: And then you like a couch or a chair, a soft chair. And I have somebody who has ADHD now works for me. Her name is Molly and she works from home, but partly she works from home because she works on the couch or the bed. And I do that when I'm working at home too, because it's much more comfortable.

Rae: Yeah. I wonder if it's one of those ADHD things that we sort of pioneer awkwardly and then everyone's like, "Actually, that's kind of better for me too." Like working in a loud office in an uncomfortable chair is harder.

(09:16) Neurodiversity initiatives: Trends vs. real support

One of the reasons I was so excited to talk to you about this is because I feel like this is a very hot kind of thing right now. Like, how do you include neurodiverse employees in the work? You know, blah blah blah blah, blah. And I love that that exists. But I think a lot of what's coming out about it is I'm not allowed to swear on here, but I would use a word that starts with bull and ends with, you know, an expletive.

And I think it's well-meant, but I think the reality of it is often sort of initiatives that kind of go nowhere or like you, it's hard to make that real. And so, if you have somebody like you who has this really, really thoughtful approach to working with people who have different styles of work and learning something as simple as like help somebody make sense out of the thing that they're thinking, help them explain it beyond their own mind.

That's something that is like a really wonderful thing you can actually do. And it's, you know, it's there's a lot of wonderful things. I don't mean to knock the neurodiversity initiatives that are happening. I think there's some fantastic stuff. We have a lot of wonderful places that are trying really hard, but it's the little on-the-ground things, the day-to-day things that change what it's like to be a neurodiverse employee.

Like you saying, "Oh yeah, go sit over there. If you need to sit over there, sit over there" and you don't feel weird or like you're having to do something special to move your lamp to the table or whatever it is, you know, like or like, "Hey, I don't know how to say this," and you go, "Well, let's talk about it."

That little stuff, for me anyway, made me feel, I don't know how to say this, unspecial in a really good way. Like I wasn't something that was different than the other things. And when you have a learning disability, you spend a lot of your time feeling like that one of these things that is not like the others.

Caroline: Yeah.

Rae: And I never felt like that working for you.

Caroline: Well, you know, I know what you mean, because I've read a lot of stuff about making workplaces or making things accessible for everyone. And a lot of times it becomes very rule-oriented. Don't do this. Don't do this. Don't do this. And I just think, just pay attention to this, to the person for whom you want to make it more accessible. Just pay attention. Just watch. Just listen. Just pay attention to who that person is.

And you could tell a lot about what they want and need and ask them, do you know? So, you're going to get your information from the person, not from your HR department, in my opinion.

Rae: I think that's very rational. I mean, accommodations are great and there's value in them. But it's true, if you have somebody who just understands the way you work and isn't like, "Well, why are you doing that?," you know, you don't feel kind of singled out. You feel sort of helped along, I guess, for lack of a better word?

Caroline: Well, you know, the model is kind of instead of having a whole bunch of people who have to do the same thing in the same way, and you're trying to change people into people who do things the same way. You want to look at the people you have and imagine what each one of them can do that's the most valuable and then kind of put it together.

And you were talking about Rachel, who was one of our, who we worked with years ago, and she was very, very different from you. And what she wrote was very different, so it enabled us to have a lot of different kinds of pieces. And, you know, she was very good at interviewing and she was a good writer. You, on the other hand, were just exceptional at kind of being empathetic and either knowing the experience that the person might be having firsthand or just being able to really intuit that and bring it to life.

So that we have all these articles in which, you know, one of the ones that I think about a lot was this piece that we did called something like "Why does your kid with ADHD have such a messy room?" And we did it because we heard that parents were asking that question, it was a very common question. And you just really understood why a kid had that messy room and really made me get it.

Rae: An experiential piece.

Caroline: You totally just made me feel what you felt looking at that pile of stuff on the floor.

Rae: I looked at it this morning.

Caroline: And how that was might be different than what somebody else felt and then kind of how a parent might work with that. Instead of trying to change you, the parent might be able to work with how you felt and figure out a way to make it feel valuable to you to do something about it.

Rae: One of the things that I think, I'm hoping is turning in the world of like mental health journalism and learning journalism, and I think part of what we're talking about now is more people are having that experience, right? More people are coming in who have these really diverse brains, and they're writing about their own experience and they're covering it from all these different angles. And, you know, I've been lucky to do this kind of work for a long time.

But, you know, when I started, it really wasn't that common to have a writer out there saying, like, I have ADHD. I have, you know, dyslexia. I have you know, it was not like a first-person type of journalist.

Caroline: Right.

Rae: And now it's more and I feel like it's making it more of that experience to like, "Oh this is what it feels like to have this. And here's what somebody who understands what that's like from the inside suggests."

Caroline: Well, you know, when we started doing this, I mean, nobody was talking about it. And, you know, you couldn't get an actor or a musician or an athlete to talk about their emotional issues or their struggles as a child. You know, it was considered career death and now everybody is talking about it. So, it's a really profound change.

Rae: Yeah.

And I think and I think it makes a big difference in terms of what the experience of someone growing up is, because it's not taboo anymore to talk about that.

Rae: It's true that a lot has changed. And one of the big positive developments, at least in the world of ADHD and mental health, is that now people actually do talk about it, in some cases anyway. I've heard people say things like "Bring your whole self to work." That said, when it comes to actually getting the support you need. It's not always that easy. Knowing you need something, and knowing what that is aren't the same thing. This is especially true for people who are undiagnosed.

Next, even if you do know what you need, communicating it is not always that easy. What do you ask for? How do you ask it? Who do ou even talk to you in the first place? And then there's the intangibles, the things that are harder to pin down. A lot of us, myself included, have felt a lot of shame about our learning differences over the years.

You might not want to tell people that you're struggling. It can feel embarrassing not to be able to do the things that other people around you seem to find so easy. You might worry that you're already in trouble and asking for something else will make them just think "She's not even worth it." And of course, this is all often much, much harder if you're a person of color or someone who has been routinely discriminated against in the past.

And then finally, even if all these things come together, you need a receptive boss who's going to take you seriously and a workplace that will care. And that is a very, very tall order for many people. I was lucky, privileged to be in a workplace that cared about mental health and where it was talked about openly. It was our literal job to talk about it. And Caroline was the kind of boss who would listen.

(17:04) "Hope is not a plan"

Caroline: So, one of the pieces that you did that we kind of, I remember working with you on, that I thought was one of the most important pieces was, it was a piece of, I think it was for back to school. And it was about, let's say you've been struggling in school.

Rae: Oh, "Hope is not a plan."

Caroline: Yes. So, I thought that was really one of the most important things you can possibly say. "Hope is not a plan." And so, when you've had trouble with something and you're going to start your next school year or just you're going back to the office the next day after something did not go well, or let's say you've made a mistake, "I'm so sorry. I'll never do that again." And if I'm the person listening to this, that means nothing.

Rae: Yeah.

Caroline: You know, saying, "I want never to do this again. I hope never to do this again" or to say "I promise never to do this again. I'm going to be better." None of those things really go anywhere unless you have a plan. In other words, and I remember talking about that article, it's like, unless you say, what am I going to do differently?

Rae: Yeah.

Caroline: What are the things that would...because, you know, my thinking is like if, a kid is really struggling or if you're struggling at work, there's a reason why you're struggling. There's something in the way you're doing it that's not working. And what can you do to set yourself up to do something?

Rae: And just believing you'll be better isn't enough.

Caroline: Exactly. Just earnestness and desire doesn't do it. So, hope is not a plan. Really struck me as an important piece of advice for anybody. Really. Anybody.

Rae: That's something you taught me, though, because the other piece of that that I knew but had a really hard time with was not only that believing you will be better is not enough. That you have to understand what went wrong, but that also feeling bad about what you've done is not enough.

Caroline: I'm so glad you said that.

Rae: That's not the right way.

Caroline: I am really glad you said that because the other thing people do is they apologize and apologize and apologize. And my son used to do that. He's like, he has a master's degree in apologizing. And it just, it doesn't solve the problem, you know. And so, instead of apologizing and feeling bad and beating yourself up, you know, it's really, it's just so much more effective to think: what's the thing I could change?

Rae: Yeah.

Caroline: You know.

Rae: I remember having, I, you know, some mistake I made at work. I didn't turn something in on time. There was something that had happened, one of these tumbledown ADHD things. And it's a groove you get in that apology, promising, wanting it to be better. And I remember you stopped me and you said, "This isn't how you want to do this," and that, it was like one of those moments where you can look back and think like, I did things one way, and then I did them another way after that.

Caroline: And I think, and it isn't, it's also important in the way you think about it is that it's not like there's something wrong with me, that I am going to change, because you are who you are. You're not going to change. But you need to set yourself up so that mistake happened because there's a there's a hole in your plan.

Rae: Yeah.

Caroline: You know, there's, you know, and you need to figure out how to fill that hole, you know, how to stop yourself from making that mistake again because you're not going to be different. You're going to be the same. But there's a way you can, you know, if there's a way to fix it.

Rae: Well, people always say "Set yourself up for success." And to me, it's like, "Set yourself up not to be completely screwed."

Caroline: Yeah.

Rae: It's very similar, but it's a much smaller thing. It's not a, it doesn't have to be shiny. It just has to make it work.

Caroline: Right. And anyway, it's very, it's so down to earth and it's so practical and it's so not about your character. It's not about your character. It's really about kind of having these practical, like, setups, you know, around you.

Rae: And I like that you say that, though, because I think I know for me and for a lot of people I know who have learning disabilities or ADHD, you feel like it is your character, you feel like you are your failure. You are a failure because you failed. Something went wrong, "What's wrong with me? Why did this happen? God, I can't believe I did it again." And that loop is not easy to break.

Caroline: Right. Well, and that's why I like the notion that there is something external to you that's a plan that will kind of make it...it's a guardrail. Yeah, that's what it is. It's a guardrail.

Rae: Thank you, Caroline, for everything, for being a great boss, for being a great interviewee.

Caroline: Thank you.

Rae: And I'm sorry I was late, which is power for the court.

Caroline: Well, while you were late, I was thinking about it, and, you know, I think I've hired a lot of people over the years at many magazines and at TMI.

(22:05) Caroline's keys for hiring

And I've come to think there's two things that I've really decided about hiring people and helping people do a great job, and they apply to everyone, but even more, I think, to people with ADHD.

And one of them is that whoever you hire, you really want to find out what they're really good at and what they're less good at and what they really like to do and what they like less to do. And then you really want to make sure they get to do those things and enable them to do the things they're really good at. And that's for everybody.

Rae: That's so sensible. And that's what I remember from working with you as you were so interested in the people who worked for you. You actually wanted to know who we were.

Caroline: That's actually my idea of fun, you know, which is to have a group of people who are talented and smart and can do a lot of things and then figure out how to really, you know, enable them to do the best work they can and to have a good time.

Rae: Yeah.

Caroline: Because I want to have a good time, too.

Rae: Thanks for listening to this episode of "Hyperfocus." If you have any questions or ideas for future topics, write me an email or send a voice memo to hyperfocus@understood.org.

"Hyperfocus" is made by me, Rae Jacobson, and Cody Nelson. Our video producer is Calvin Knie. Our music comes from Blue Dot Sessions and Justin D. Wright mixes the show. Ash Beecher is our supervising producer. Briana Berry is our production director and Neil Drumming is our editorial director.

This show is brought to you by Understood.org. Our executive directors are Laura Key, Scott, Cocchiere, and Seth Melnick. Understood is a nonprofit organization dedicated to empowering people with learning and thinking differences like ADHD and dyslexia. If you want to help us continue this work, you can donate at understood.org/give.