Freelancing, Self-Employment, and Mental Health

Talking about Self-Awareness and Anxiety (with Hello Monday’s Jessi Hempel)

MORRA AARONS-MELE: I’m Morra Aarons-Mele. This is The Anxious Achiever. We look at stories from business leaders who have dealt with anxiety, depression, or other mental health challenges, how they fell down, how they picked themselves up, and how they hope workplaces can change in the future. Today, freelance work and managing anxiety and depression. I’m a small business owner, which means I work from home a lot. I’m responsible for bringing in income. My income can fluctuate from month to month, or even year to year. If I don’t sell, I don’t earn.

What I experienced is familiar for lots of small business owners and freelancers out there. Even during the best economic times, depending on only yourself for your paycheck can be stressful. While life untethered to an employer can bring freedom, it has some really big stressors – money, for one. Freelancing or working from home can feel lonely and isolating. Many of the traditional milestones by which we measure our career and our professional growth just don’t exist. There’s no promotions. Instead, you’re actually in almost constant job interview type of situations in which you have to try to prove yourself.

Trying to manage all these stressors, while also dealing with a diagnosed mental health issue, can be hard. Sure, you can sneak out for a therapy appointment in the middle of the day, but sometimes, it can feel like the world is collapsing, and you just don’t have a safety net. Later in the show, we’ll hear from the writer, Ada Calhoun, about her strategies for managing anxiety as a freelancer, but first, Chris Brogan. Chris is a New York Times bestselling author and business owner. He created the StoryLeader system and is someone who suffers from clinical depression. He wrote, and I’m going to quote here, “People with depression can be successful.”

Now, read that sentence again. I’m not saying successful people can be depressed, although that’s true. I’m saying that people who suffer from depression can be successful, even though they are depressed. A, I couldn’t agree with you more. B, why, Chris, did you want to sort of reframe the sentence to say that people who have depression, who are depressed, who may have chronic depression, dah-dah-dah-dah-dah, can be successful?

CHRIS BROGAN: Well, I deal with a minor case of major clinical depression. My diagnosis is major clinical depression, but I have kind of the lower end of that scale. I’m a person who has done all kinds of work as an entrepreneur, as an author, as a keynote speaker. I do a lot of consulting with big companies. These two things coexist. I guess a lot of what I do, sort of as a way to help people figure out who they want to be when they grow up, is I try to look for excuse removal systems. I’m always looking for what excuses are in somebody’s path. Someone will say, “Well, I can’t be this. I deal with clinical depression.”

Clinical depression differs from feeling down in the dumps, or depressed, or whatever. Clinical depression, it’s just a chemical thing. It’s the same as diabetes. Some people take medicine for it. Some people take, specifically, insulin for it. Others just try not to eat too much cake. With depression, it’s the same sort of thing. You have to deal with some meds, most times. You have to deal with some lifestyle changes. Then, beyond that, you can actually live whatever life you think you need to live.

MORRA AARONS-MELE: I mostly agree with you, but hasn’t there surely been a time when you’ve been in a more severe clinical phase where just getting out of bed has been hard?

CHRIS BROGAN: Absolutely. The same with anyone with any kind of a medical difference, or whatever. Someone with diabetes can go through a bad bout because something changes, or they don’t get their food in the right time frame, and whatever. With depression, there are definitely days where the bed is the best place for me to be. It doesn’t mean you can’t have your career. It just means that you have to take extra steps, and there’s things that happen.

Driving around with the brake on is kind of how I like to explain depression, sometimes. Sometimes, when I’m dealing with depression, it’s like ripping that parking brake up as high and tight as you can go and then still trying to drive your car. It groans, and it barely gets anywhere. You’re like, “Well, that’s how it is.” With depression, what happens is, everything is a lot harder to do. Everything is slower to do, etc. You can still get it done.

I’ve given keynote speeches in the midst of some bad depression. What’s happened is, I didn’t sleep very well the night before, and I didn’t go to every one of the meet-and-greets. I’ve become the absolute best person in the universe at the Irish Exit. Sometimes, I’m so good at it, I don’t even enter. People just think I was there.

MORRA AARONS-MELE: You use the hashtag, right? If people see you tweet using the event hashtag, you were there.

CHRIS BROGAN: Yeah, exactly. It’d be like, “Hey, I’m over by the dips. Where are you?” “I’m in my bedroom, rocking back and forth.” You can do it. I guess I just wanted to point that out to humans, because I think, a lot of times, we’re looking for somebody to come and stamp us somewhere with “You don’t have to do this because you are somehow flawed or dented.” I just think we can all operate with a little bit of dent in us.

MORRA AARONS-MELE: I agree with that. I think that one of the things that I always try to convey to people, because I have anxiety and depression, I think you do, too, is I’m a professional, damn it. How I feel on the inside is not how you will get me if you’re paying for my time. I have mostly learned over the many years to fake it.

CHRIS BROGAN: A lot of the best comedians and entertainers have some level of depression in their life. They have clinical depression. Robin Williams famously did and passed away from that. Most of the people you think are the funniest people in the world also deal with that. One of the things that you kind of get free of charge with depression and anxiety is a lot more self-awareness, a lot of self-deprecation.

There’s a lot of opportunity to kind of look down at your belly button and explain to the world the ways in which you’re flawed. Let me tell you all my flaws. They’re free. I think these can all be superpowers, though. I think that we can operate with these. People who don’t deal with depression don’t understand how to get up from failure. People with depression, we feel like every day … You might as well just keep going, because you just kind of expect it, and you’re just going to keep going. It’s a yes and not a, “Oh, wait a minute. I’m going to stop there.”

MORRA AARONS-MELE: I’m going to reframe that, because I don’t want a bunch of haters to email me and be like, “What? You’re saying that everyone who doesn’t have depression, they’re a bunch of wimps?” I’m with you that I think that mental illness, like any disability or difference, gives you a resiliency. That is really important.

CHRIS BROGAN: Sure. I don’t disagree with that.

MORRA AARONS-MELE: I’m just so there with you on so many levels. Sometimes, performing when you’re in a bad state is actually the easiest thing you can do. Going out to dinner with a friend is the hardest.

CHRIS BROGAN: That’s a very good point, too, that really intense one-on-one interaction is a lot more challenging than standing around onstage somewhere and blurting out your dumb things. There’s just so many of our jobs that we can do on autopilot. We can kind of chug through them and get through the discrete tasks. Sometimes, it’s human interaction that’s really tricky. Other times, for me, when I’m dealing with depression forms, I’m looking over at the mail that just came in today that probably won’t get opened for a few days, just because, for whatever reason, that’s not going to work. Bills aren’t that helpful when you’re kind of down in it. Work, work is the thing that we do.

MORRA AARONS-MELE: Have you always been depressed? Can you remember when you had your first bout of depression, even if you didn’t know that’s what it was?

CHRIS BROGAN: I don’t know when I really caught up to the diagnosis of clinical depression. It was much later in life. I don’t know if I was just lucky before then, or what. Pretty sure, I probably had the black dog for a lot longer. The first anxiety instance, I was pretty sure I had a heart attack. I don’t remember. I was on public transit somewhere, I forget, where I felt a cold sweat just shoot down the inside of my body. You hear people say that it was a cold sweat, and it came out of nowhere.

Legitimately, this felt sort of someone took a cup of water and poured it down the inside of me. I went, “That’s weird.” I went to the doctor, to the hospital actually, to the emergency room. It was really weird. The reaction I got was like, “You didn’t have a heart attack, you big stupid idiot.” I was like, “Well, that’s not really good.” That’s when someone taught me what anxiety attacks were. I was like, “Oh.”

After a little while, when I finally went and saw a shrink, you do some diagnosis work and all that, and they’re like, “Nope, you get it. You get depression.” When we sort of went through a whole bunch of questions, and it was like, “Well, kind of a severe one, but you have sort of the lower end of that.” I guess they sort of split it into two. I don’t ultimately know, because there’s no numbers that go with it. It’s a little bit of-

MORRA AARONS-MELE: It’s not blood sugar. It’s funny because I was going to ask you about that later. I’m going to bring it up now. You say a lot, “I have mild clinical depression.” You’ve already said that twice in our interview. It’s almost like you’re minimizing your depression.

CHRIS BROGAN: 100%. Downplaying it, absolutely.

MORRA AARONS-MELE: You’re kind of funny about it. You have silly names for it. Why?

CHRIS BROGAN: Again, I never say I’m depressed. I say I deal with depression. I just interviewed a guy who was in his last few days with cancer. I had no idea that he was in his last few days, because the last time the doctor said he had a few months to live, he lasted another whole year. This time, they said it. They said, “Well, we really mean it this time.” He said, “Well, we’ll see.” When I interviewed him, I put the whole interview up and called it, “I’m dying.” He sent me a message. He goes, “Hey, can you do me a favor? Can you change it from ‘I’m dying’ to ‘Facing death’?”

I was like, “Oh, my gosh.” He’s a super-Buddhist. I was like, “That totally makes sense.” He’s dying, and he’s throwing a label on you. I’m not depressed. I just deal with depression. I downplay it because I don’t want it to be given a bigger role in my life than me. My ego won’t allow that. I think I’m much more successful than my depression. My depression has stopped me far fewer times than my ability to fight with it has let me get to where I need to go.

MORRA AARONS-MELE: Say more about that, because I truly believe that my anxiety has made me who I am and that I am awesome because of my depression. It’s truly a gift in my life, mostly, except when I’m at the ER, thinking I’m dying. How has learning to fight with your depression or negotiate with it made you better?

CHRIS BROGAN: See, negotiate would be closer. I carry it with. I’ll tell you, there’s an example of this.

MORRA AARONS-MELE: Yeah, you travel with it every day. It’s part of who you are, right?

CHRIS BROGAN: Oh, my gosh. I wish I could leave it somewhere at the bus stations, everywhere. There’s a book by Dr. Matthew McKay called “Self-Esteem.” It’s a really old-timey book. It’s worth reading, even though it’s much bigger than it has to be for a book. In “Self-Esteem,” he talks a lot about the inner critic. He basically kind of labels this concept of the inner critic that we all know. We just didn’t know it had a name. Inner critic is the person that says, “I don’t know why you’re going to start this new thing. You always quit.” That’s the inner critic. It’s a phenomenon that … We can’t touch a part of our brain and find that critic, but it’s in there.

He said, “What the inner critic is, best anyone can tell, what the inner critic is trying to do, it’s trying to save you from feeling bad or dumb or stupid, or some other negative thing. It thinks it’s protecting you.” This part of your brain that we call the inner critic, or this part of your programming or operating system, is saying, “I’m going to make you feel bad before someone else does, because we think that’s a better idea.”

MORRA AARONS-MELE: I thought that was my parents’ job, but okay.

CHRIS BROGAN: Also true. Well, our inner critic is always looking for people to back it up to. Dr. McKay says, “The only way to beat it is not to fight it.” He says, “You have to thank it. You have to say, ‘Ah, man. Thank you so much. I so totally get what you’re trying to help me with here. That’s so good. Thanks. I’m going to do my own thing, but thank you so much for that.’”

MORRA AARONS-MELE: Talk us through what your depression is, not day-to-day but, sort of, what work life looks like. Like, you don’t show up at an office that someone else owns and report for duty at the same time every day. What does your work life look like?

CHRIS BROGAN: Thank the sweet Buddha. No, I’m fairly unemployable at this point. I run my own company. I run two different companies. One is called Owner Media Group, and one’s called Chris Brogan Media. In my roles, the one real challenge that I’ve put before myself is that all the things I do professionally require an immense amount of creativity. I do business advisory work. I do digital marketing work, content marketing work. I do lots of content creation work.

When it comes to that creative stuff writing, sometimes when you’re down in it, that’s the thing that you feel a little tapped about. Creatives have different ways that they kind of interact with people when it comes to what their output is. Money, for sure, is probably my number one trigger for outward things that made me feel depressed. I just keep reminding people, it’s chemical. I don’t get a choice. Some days, everything’s great, and I still am feeling it. I’m still going to feel it. Kind of circumstantial things, money is one.

The other is you get a lot of opportunities as a creative person to feel like a kid at their seven-year-old birthday where no one came. You would send all the invites to all your classmates, and no one shows up. You get that feeling a lot when you make creative stuff. You asked about my day. My day is mostly creating stuff. My days are never super full and busy, on purpose. I schedule my days to about 40%.

That’s a skill that I put together. I advocate for this to people who don’t deal with depression. I think everyone over-schedules themselves immensely, so that they run into these weird, crazy situations, or they’re all talking about how busy they are.

MORRA AARONS-MELE: How did you learn the hard way? Did you learn the hard way about what worked for you and what didn’t, in terms of managing your time running your business as someone who gets depressed?

CHRIS BROGAN: Like, a lot of things I’ve done in my life, it’s error and error. I don’t know if there’s any trial. I think it’s just … I just fail all the time. What I figured out was, when I say “yes” to somebody when I’m feeling, let’s say, neuro-normative, to make it sound scientific, when I feel like a normal human being probably does, I just do the thing. When I don’t feel like that, here’s a real-world example from this week.

Three days ago, someone pings me and says, “Hey, can you record this video? All of these people are going to get together. We’re going to make a little virtual conference, and we’re going to do it right now, and I just need 20 minutes.” I’m like, “Yeah, sure. Go ahead.” I went over to start to do it. They say, “One thing, we need it to have a white background.” I’m like, “I have a studio, and it has a blue background. It has a bookshelf and stuff. It doesn’t look like that.”

I’m like, “Now, I’ve got to go find a thing.” Depression is everything you think right after I was just supposed to push “record” and be done shortly after. Depression is like, “Now, I’m going to have to do this thing.” I write back this little whiny email, “White? Why does it have to be a white background?”

MORRA AARONS-MELE: This is so hard.

CHRIS BROGAN: Yeah, exactly. I gave them what they wanted, but I complained the whole way and felt grumpy about it the whole way, because of depression. That’s how it works, for me. What I learned was, if I can do more of the things that I really want to do … I’ll give you one super … It’s not a secret, because everybody can know it. The thing that gets me out of depression faster than anything in the world is just helping other people do something.

If I help other people and lift them up in some way or make them feel better, that gets me out of depression. Let me put a little asterisk and a warning. You’re going to go read the bottom of this label. It’s not the same as love. You have to love yourself before you can actually love other people. It just doesn’t work the other way. You can help other people while you’re still depressed. It’s okay.

MORRA AARONS-MELE: I tend to be a pretty reclusive and introverted person on a good day. When I’m feeling really depressed, I will totally withdraw from people. I will be mean to the people who love me, so that they get angry at me. Then I will just disappear from my work world. If the people that I work with closely didn’t know that I had depression, I could be in real trouble, because there are days sometimes and, again, I run a business, I drive business development and sales for this small company that pays for a bunch of people.

If I’m in bed, not able to do something really small like answer an email, that has ripple effects, not to mention the fact that I’m a parent. I have found it necessary for my team to know. It doesn’t happen often, but there have been times where I have had to say, “I’m sorry. I’m really depressed right now.” They know to say, “Can I take this over?” I’ll be back to them in two, three days because God bless antidepressants. I’ve had to employ that level of radical transparency. I’m curious how that works for you.

CHRIS BROGAN: I see stuff like that all the time. I don’t have any sense of self-preservation when it comes to any of that, I don’t think, and I could be totally wrong, maybe. The entire business world has a little asterisk next to my name. Disney says, “Well, we worked with him in the past. Now, we know he deals with depression. We won’t call him this week.” Maybe, that’s happening. I don’t know. There could be a secret blackball list. I don’t feel like it’s true.

I feel like every time I tell people I deal with depression, the only thing I end up having to do is sort of explain to them what that really means, because the side challenge is that they accidentally think it means like “I’m saying I’m down in the dumps.” I don’t mind telling anyone I deal with depression. What I always say is, “I very, very quickly rattle out. It’s a lot like diabetes for me. I just have to take my meds and do smart things, and I’m good. If I slow down, I’m going to let you know I’m slowing down. It happens about once every 16 months, in any kind of way that anyone else will really notice it.”

MORRA AARONS-MELE: What routines keep you on track when you’re in a down cycle?

CHRIS BROGAN: None. I have none. I probably need a better routine for business development. That’s for sure. I have a system that I created. It was one of the courses that we built called the 20-minute Plan Jumpstart. In that thing, I have a system where I work three hours a day, every day, on my business. I guess that’s the closest I have to a routine. That’s three hours.

MORRA AARONS-MELE: That sounds pretty methodical and good.

CHRIS BROGAN: Well, except there is no specific time of day. It is essentially nine checkboxes every single day. It’s like, if you drew kind of a flattened wide side of a Rubik’s Cube, it’s nine squares. Basically, those nine squares account for 20 minutes each. Those three hours are broken into three sets of three 20-minute blocks. Make sense? I book those three hours to grow my business in some way or develop the stuff around my business in some way. They can happen anytime. Every now and again, I can fudge one and just say, “You know what? The way the day is going, I think eating a sleeve of Oreos, instead of the entire package, is going to be a win.”

MORRA AARONS-MELE: I’m so with you. Who cares? Are there times of day that are better for you, generally?

CHRIS BROGAN: Yes. When I’m dealing with depression, late morning starts happen, whether or not I want to. I’ll wake up really early, but I won’t really get anything done until at least 10:00 a.m. When I’m not dealing with depression, I wake up early, and I get free extra hours that way. I’m not a creature of habit. I think this comes from the discipline of my writing. I write a lot. The one thing you could say that I do for sure is at least 2,000 words a day.


CHRIS BROGAN: A day. The way I do that is I make it completely requirement-proof. Someone will say to me, “I have to have this exact paper and this kind of pen and this light,” or, “I can only write at coffee shops. I can only write if no one’s making noise and all these things.” I can write anywhere. I’m like a military person, how they sleep 20 minutes here and there whenever they need it. I can do that with writing. That’s the only thing I can say is systematic. Nothing I do is time-bound. I guess that’s what I say when I don’t really have great discipline. I have nothing that’s time-bound.

MORRA AARONS-MELE: Well, I’m reflecting again, because what you’re describing to me is someone who’s really disciplined. To write 2,000 words a day, to take your little Rubik’s Cube blocks and work on your business, takes tremendous discipline. You’re totally downplaying it.

CHRIS BROGAN: Yes. I’m an unreliable narrator. I think that’s true. No, I think the reason I say that, too, is that, we hear this term “virtue signaling” a lot. You see someone standing around with their $20 bill that they’re heading over to the Salvation Army person or something. They don’t let go of that $20 until enough people see it go in, that kind of a thing. Well, I think that for people that are really, really into productivity, for instance, I call that noble masturbation, it feels good, and it seems like it’s a good idea, but it’s not the same thing as real work. I don’t tell people I’m into productivity. I’m not into productivity, I’m into getting my work done.

MORRA AARONS-MELE: I love that. The last thing I want to talk about. We talked a little bit about money at the beginning. I want to hear your advice for listeners who may find themselves freelancing, who are worriers, who have anxiety, who have occasional bouts of depression, and who are saying, “I can’t be a freelancer. I can’t pursue my creative passion. I’ve got to stay employed by someone else, because I’ll never be able to manage the uncertainty.”

CHRIS BROGAN: Well, the weirdest thing about this, and I’m sure everyone says some variant of the same, is that if you are trusting one employer. That’s the opposite of feeling certain because that one employer makes choices that have nothing to do with your merit. We accidentally think that we’re employed by the grace of our hard work, but we’re not.

We’re just employed because someone needs what we do at that point, or there’s enough money to afford something that we do, or that it’s a worthwhile expense, or whatever. Letting one human entity or one small group of people decide your future is a lot less easy to manage than having the money you need to live split across five different clients. If any one of them leaves you, you still have 80% of your revenue.

MORRA AARONS-MELE: Diverse portfolio, yeah.

CHRIS BROGAN: Well, I’ll give you an easy real-world example. My mom worked for the telephone company for 29 and three quarter years. At 30 years, you can retire. When you retire, you get your full pension. They let her go at 29 and three quarter years. They stuffed it in her face – my mom, who had been nothing but fiercely loyal to the phone company. It’s terrible. My mom thought I should follow in her footsteps and do that same kind of job, and I said, “Are you crazy? They just spit on you.”

I’ve had multiple bosses for a while. Guess what? Sometimes, I run out of money entirely, bank account down to two digits or three digits. Unlike a job job, where you only get the money you get every week or two weeks, or whatever they decide to pay you, I can just go find some way to make some more. I think that that’s the beauty. My advice is you’re a lot safer if you have the controls to earn.

MORRA AARONS-MELE: Cash flow planning is not something that keeps you up at night, I’m taking it?

CHRIS BROGAN: No, because right now, as of this interview, I’m at the bottom of where I’ve ever been in my finances, the bottom, bottom. I had a two and a half year stint of depression, just kind of draining away all my savings and me being, “Well, I still have a little money,” and I wouldn’t have to try so hard for clients. Well, now I’m at the point, it’s like, “Who do I have to kiss around here to get a job?” because I’ll do it.

MORRA AARONS-MELE: What will you do?

CHRIS BROGAN: Just earn money. I’ll just go find people I can help. It’s the way of business. Business is, “I know something that you don’t know. I’ll help you do it. I can help you set up the thing. I’ll help you do it.” There’s a lot of people suddenly thrust into working remotely and marketing remotely, who I’ve been teaching one form of podcasting or another since 2006.

Now, they want to be podcasters. Fourteen years after I started doing this, they’re like, “How do you do that?” I’ll show them. There’s just always ways. There’s always things you can do. People forget that the thing that they do easily is the thing that’s really hard for someone else, and that’s where money comes from.

MORRA AARONS-MELE: Chris Brogan, thank you so much.

CHRIS BROGAN: It was so much my pleasure. Thanks for having me on.

MORRA AARONS-MELE: Someone else who understands the trials that come with the freelance life, even when a certain level of success has been reached, is Ada Calhoun. I sat down with Ada to talk about the pros and cons of self-employment and working remotely and what it means for your success and your mental health.

I wanted to start, because I think you talked about this. We both were the same age. We both grew up working in media. I think that we both worked for powerful women older than us in media and observed them, certainly. I don’t know if this was true for you. They seemed to have it all. I was the executive assistant, my very first job out of college for a film company, very chic job, paid nothing. I was the executive assistant to the Vice President of Publicity and Marketing. Sarah Eaton, she was a great boss. I admired her so much. She went to screenings. She had lunch with The New York Times. She got her hair done at a very fancy salon. I booked it all. I just was like, “Wow, this is who I want to be.”

That’s what I thought I would be. When I was starting out as an executive assistant, that path forward just seemed pretty clear. That world just sort of vanished. Those VPs certainly don’t have executive assistants anymore. It’s much harder to get a great job with great benefits and have lunch with The New York Times, or have lunch with anyone in media. What’s your experience been? Does that resonate with you?

ADA CALHOUN: It does resonate with me. I started out as an intern and then worked my way up. I became editor-in-chief of an online magazine. It was about, I guess, 15, 16 years ago. That was what I expected. There were these very clear things. You go from assistant to associate, to editor to senior editor. I don’t see those jobs existing anymore. That ladder, I feel like, has totally collapsed.

Now, it’s like everyone is doing everything. It’s all from home. It’s all freelance. There are no benefits. There’s no ladder, definitely nothing that takes you into a place that has any kind of security net. I don’t think I know one person. I know a lot of people in media who have an office with a door you close, and then the phone and the assistant, all of that, and health insurance and dental insurance. It just feels like it’s like a Mad Men-era relic almost, that idea. Everyone’s just on their own in their own little bubble, taking care of everything. It’s a little scary.

MORRA AARONS-MELE: One of the things that you were very brave in talking about was the embedded fear and the fear that sort of didn’t go away, even though people can look at you and your name … you’re a bestselling author. You’re very open, I think, still that there is a fear that goes along with the freelance life of a writer, the freelance life of anyone, frankly. Can you talk about that? Are you still scared, even though you just had a really successful book come out?

ADA CALHOUN: I’m less scared this minute about that. There are many other things in this world right at this moment to be very scared about.

MORRA AARONS-MELE: Well, indeed.

ADA CALHOUN: It feels very surreal, just to be talking about anything else. I do feel really lucky that I had that book happen when I did, because I never had money in the bank before the last couple of years. I never was not paycheck to paycheck. I’ve actually gotten rid of credit card debt and all that. It feels much better. I know that sounds really obvious. There is some comfort in it. I don’t feel that far away from it. I feel like in a year, stability on the cushion code, that’ll be gone.

That was really what the book came out of. I had this summer where I had three freelance gigs fall apart for different reasons, all in a very short period of time. That was the money we were going to use to pay off our credit card debt and get us through the next six months, and it just wasn’t there.

Suddenly, we had all this debt, and I had no way to make any money. I asked my editor of my previous two books, which had done okay for a kind of indie or independent publisher, and all that. They had, I thought, done pretty well. They got a lot of press. He said this thing. He said, “Sales track is sales track. We love you. Of course, we’d want to do something else. The last book didn’t really do what we thought it would.”

Then I was, “Great.” My plan was to sell another book. It’s like, “Now, I won’t be able to do that. I don’t know about this ghostwriting thing. If I freelance, it’s $200 a piece.” Really, I thought it was over in that moment. That was 2017. I thought my career was done.

MORRA AARONS-MELE: I’m just pausing because I’m feeling that anxiety. I’m feeling that anxiety with you. Were you still the breadwinner?

ADA CALHOUN: Yes. I have a wonderful husband. He’s really supportive and fantastic. He is also a performance artist, a musician. He has many jobs. He teaches. He works as a box office manager. He does front desk stuff at other places. He has many, many jobs. None of them pay very much. They’re all freelance. It was sort of … I’ve been the one who’s brought in most of the money every year.

MORRA AARONS-MELE: Did you ever feel like you needed more structure in your work life? Was that at ever part of the motivation to look for a corporate job? Is that something you just never needed?

ADA CALHOUN: Every once in a while, I would daydream about it. I would have these fantasies of going into the break room and getting a cup of coffee and going back to my desk and sitting at the desk and having my landline phone and my desktop computer. I would dream about it, having coworkers you’d banter with. It’s been so long since I did those things. I still remember them in a fond and romantic way, much as one might look back in an idyllic childhood in the countryside or something. It doesn’t feel real. It doesn’t feel like it’s actually something within reach.

MORRA AARONS-MELE: If you don’t mind me asking, because you’ve been open about your anxiety and your mental health, as a freelancer, you don’t always have the best insurance, right?


MORRA AARONS-MELE: How do you handle therapy, mental health, paying for self-care, when you are a freelancer? How has that been?

ADA CALHOUN: I did therapy for a while, 15 years ago. Then I’ve gone back for short periods of time. I’ve said because it’s, of course, not covered by insurance for me. I’ve said, “I can’t afford to come five times. Please help me try to fix this major problem as best as you can in less than five times.” Fortunately, I have the most wonderful therapist. I love her so much. She really gets a lot done in a short period of time. I’ve gone back more recently, and she’s been great.

I pay for my own insurance. We have the bronze plan from the State Exchange. It’s $1,200 a month for the whole family. It’s not great. There’s a high deductible, and it doesn’t cover things like mental health care. Again, it’s been pretty catch-as-catch-can, where if I have a little money, I squirrel away money for something like therapy. Self-care stuff, I actually just wrote a piece about self-care and how it doesn’t actually work a lot of the time. A lot of it feels rather lonely to me.


ADA CALHOUN: What really helps me the most is being with other people, helping other people doing things that feel kind of slightly virtuous. That, to me, actually, is more of a mood booster than getting a manicure or whatever.

MORRA AARONS-MELE: I want to talk about midlife, because the real thrust of your work is new. We hear a lot about how difficult it is, and it is very difficult, for young people just starting out to get their footing financially and career-wise, for all the reasons we’ve talked about – the gig economy, the lack of security. I do a lot of work in my day job with AARP.

There’s also tremendous data about financial security for seniors. There aren’t pensions like there used to be, etc., etc. You and I are both Gen-Xers. We’re in our early 40s. We get ignored. We’re often called the stunted middle children of the generation.

ADA CALHOUN: Jan Brady Generation.

MORRA AARONS-MELE: What is your position on, and I want to zoom in on anxiety, about the effect of our current financial highwire acts on our mental health? What did you learn in your reporting journey, talking to so many midlife people?

ADA CALHOUN: Well, I talked to a couple hundred middle-aged women around the country. Almost all of them had anxiety about money and anxiety about work. They just felt like the pressures on them to take care of other people were massive. They had the pressure on them to bring home enough money without a lot of support or, I guess, help.

I feel a lot of them talked about their employers not offering flextime or benefits or just kind of any sense that they were safe or could rely on the company to have their back, if there was an illness, for example, or if they had to take leave to go have a baby or take care of an aging parent, or whatever it was. There was so much fear.

It was sad to me to learn that, actually, a lot of the fear was very well-founded, looking at the numbers, looking at what employers were offering. We’re not crazy, if we feel like there’s no stability in our jobs or if we feel like there’s a ton of pressure on us. There just is.

MORRA AARONS-MELE: I think that there’s a tremendous psychological component here. You actually talked about ACEs, Adverse Childhood Events. Again, in my day job, I run a calls marketing firm. We work with the CDC and the American Academy of Pediatrics on trying to socialize this term, ACEs. It’s a mouthful, but the basic idea is that adverse childhood events have far-reaching effects. ACEs are everywhere.

There aren’t certain kinds of families that have ACEs. When you wrote about a lot of us growing up in the ’70s and ’80s, growing up with ACEs that went on acknowledged, I went back to my numerous ACEs from the time, that I was sent off on my own to summer camp at age eight by my parents who were not speaking to each other and molested on a train-


MORRA AARONS-MELE: … to a van blowing up at another summer camp, to just numerous things. Frankly, even though my childhood was technically fine, there was no conscious uncoupling, back then. My parents waged war with me. Just, parenting was different.

ADA CALHOUN: Yeah, it was.

MORRA AARONS-MELE: I think kids were often collateral damage. My father would just not send money to my mother when he hated her. Today, as someone who runs my own business, I guess I’m not technically a freelancer anymore. I own a small business. Today, with something like coronavirus, where half of my contracts dry up, even though I’ve done lots of therapy, there is that feeling of, “Dad’s not paying the mortgage this month.” Is that unique? The risk of sounding like a stereotype of a whiny, white middle class, middle-aged lady-


MORRA AARONS-MELE: … is that unique to us? Is it something we carry? How do we work through that? I can’t stop coronavirus. I can’t change my childhood. I can try to absorb it and work with it.

ADA CALHOUN: I think we can acknowledge that all of us, and this goes for all people, every race and every level of income, and all that, it doesn’t mean that you didn’t experience trauma in your childhood.

MORRA AARONS-MELE: ACEs are everywhere. I’m going to do a PSA for the CDC. ACEs don’t discriminate, right?


MORRA AARONS-MELE: Every family, often, or any kind of family.

ADA CALHOUN: The study that this came out of was done at Kaiser Permanente. It was done with people who had enough money to have jobs in this area. No one had health insurance. What they did in the study, as you know, is they looked at these Adverse Childhood Experiences against the medical records. It’s 10,000 people, some huge number that they studied. These were mostly middle-class people.

If they had more than four traumatic experiences, their rates of things like diabetes, heart disease, depression, suicide, all of this went up and up and up exponentially. With more than four ACEs, I think you’re 1,200 times more likely to commit suicide. It’s not because people can’t handle it or that they’re weak or something. It’s because these things take an actual physical toll on your body and your brain, and they rewire things when they happen.

It’s something like having been sexually assaulted, or that sense of, “We don’t have any money,” or divorce, or fire, or whatever it is. I just think we have to acknowledge that that is playing a big part in every aspect of our lives in middle age, that that lingering trauma, it doesn’t just go away. It’s haunting.

I think it’s especially haunting, sometimes, with money. I remember my mother used to say, very second wave feminist type of thing, she used to say, “You have to make your own money. No one else is going to help you.” It was not bad advice. She didn’t want me to rely on a man for money. She felt like she’d had to learn that lesson herself. She’d made her own money. She was proud of it. She wanted that for me. The message that I got was that if I didn’t make my own money, I was just doomed. I was doomed.

Then, once I had a family, I was like, “They were doomed, too. My baby was going to starve. Everybody was going to wind up on the street if I didn’t get enough freelance work that month.” It just gets down into you. So many of the women I interviewed, I would ask them, “What would be enough?” They had a lot of trouble telling me what would feel like it would be enough where they would be safe money-wise.

MORRA AARONS-MELE: If a fairy godmother came down and waved their magic wand and said, “Ada, I’m going to give you that cushy corner office and an executive assistant, lunches in the Conde Nast cafeteria…” would you take it now?

ADA CALHOUN: I don’t think I would take it now. I think, ask me again in a year, and it might be different. At this moment in time, I feel like, because I’ve had to make my own life and my own career, cobbled together from all these different things like freelancing and ghosting and teaching and writing my own books, I feel like I’ve been able to say all the things I want to say in the world in one form or another. I feel that’s a great gift as a writer, to have those outlets and to feel heard and seen. I get messages every day from people who read things I write. Most of them are grateful. That’s all I could ask for.

MORRA AARONS-MELE: That’s it for today’s show. Thank you to my producer, Mary Dooe. Thanks to the team at HBR and to our guests, for sharing their experiences and truth. Thanks to our advertisers and to you, the listeners. I’m so grateful for your feedback. You can always email or tweet me @morraam. If you love the show, tell your friends, or subscribe and leave a review. From HBR Presents, this is Morra Aarons-Mele.

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