"On The Internet, Everyone Looks Rich" with Jenny Blake

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0:42Morra Aarons-Mele: There's a business book that you really need right now, and it's called Life at the Speed of Play. Launch Products People Love by Mark Pincus. He's an entrepreneur's entrepreneur, known in Silicon Valley as one of the most prolific idea generators. I guarantee you've played one of the games that he has invented. And he's going to give you his book, two for the price of one. If you go to getmarksbook.com slash anxious, he will send you a second copy for free. If you're thinking about starting an online business, launch before Black Friday, a time of year when more people are already shopping and ready to buy.

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1:27Jenny Blake: I like figuring stuff out with other people, and that's why I like Notion.

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2:18Morra Aarons-Mele: That's all lowercase letters, notion.com slash achiever and try Notion today. And when you use our link, you're supporting our show.

2:31Morra Aarons-Mele: I'm Maura Aarons-Mele and this is The Anxious Achiever. The title of this episode is On the Internet, Everyone is Rich. Now, of course, that's not literally true. It stems from a conversation that I had a few years ago with a friend who is also a professional content creator. I guess you could call her an influencer. And she said, you know, I just feel like compared to everyone else I follow, I'm doing so much work and I'm making so little money. And I actually knew the person she was talking about. And I knew that that person also wasn't having a very good year. And while I didn't spill the beans on my friend, I did say, you know what?

3:19Morra Aarons-Mele: On the internet, everyone looks rich because that's what we do, especially if we work for ourselves, right? We have to eat what we kill. And so we want to present a certain kind of image. We all look like we're killing it. But when it comes to the actual revenue we're bringing in, things get a lot more opaque. And today is a really frank and open conversation between I mean, two self-employed people who have definitely killed it at times, but have been having, you know, in Jenny's case, a rough few years and in my case, a rough year. And I really love this conversation because it's very honest about money and revenue and also how we as people who work in the field of leadership development and personal growth try to thread the needle between believing the sometimes toxic positivity that we all spew about hope and resilience and rebirth and regrowth and pivoting with the fact that you don't know.

4:28Morra Aarons-Mele: You don't know if it will get better. You don't know if your business will turn around. This could be a failure, or as Jenny calls it, a flop. And that's something that we have to deal with. And how Jenny deals with it is with art and creativity and writing and putting one foot in front of the other, and her very special Mad Libs and Permissions Libs. So this is a great conversation for anyone who's been just having a rough year. And I know many of you are. Jenny Blake.

5:08Morra Aarons-Mele: Jenny, I'm so excited. I inhale your substack and I'm really happy to have you here.

5:16Jenny Blake: Oh, thank you. And as I told you before you record, I've been a longtime listener and admirer from so far away. And the day I saw you subscribe to Rolling and Doe, I squealed with glee. And I just thought, I must be doing something right if more I was reaching out. So it's really a treat. It's like a culmination of many, many years of loving this podcast and what you do. So I'm thrilled to be here.

5:40Morra Aarons-Mele: Oh, gosh. Well, thank you. I mean, I'm struck in reading your body of work also. So just I feel like we might be the same person. But that's really a little bit of what I want to touch on today is you write so openly and so beautifully about the creative journey of not knowing as an entrepreneur and the stakes. and one of the things that I like about your writing and where I think we are not the same person is that you are very hopeful and you look to art and nature and lived experience to inform that hope in your writing which is so wonderful but I have a question for you which I want us to sort of explore today, as well as you can share your story and your thinking with the audience, which is, what if it doesn't all work out?

6:49Morra Aarons-Mele: It's something that I have been wrestling with myself in the past few months. I've had just a terrible year in my business. And, you know, I'm turning 50 this year. And I was like, what if I'm done? What if the pivot that I have embarked upon since 2022, when I sold my business and tried to do sort of workplace mental health full time, what if it's failed? And it struck me to be like, wait a minute, Maura, it can't fail because you're resilient and you're strong and you meditate and you do all the right things. And then it was sort of like, well, who says like people deal with failure every single day?

7:34Morra Aarons-Mele: Why are you so special? So I kind of want to explore that a little bit, your own thoughts, where you are in your journey. But let me start with a question that I like to ask people, which is what is your relationship with anxiety right now?

7:51Jenny Blake: Oh, that was so many good questions in there. And I'm sorry to hear that it's been a tough year. I just want you to know you're not alone in that. I for sure have been going through a wilderness and what my friend Jen Smith calls a winter. She's all about your career seasons and it's not just age-based. I feel like so many of us were catapulted into the wilderness and not necessarily right in 2020, although for some that was it. For me, it was like the years of fallout that resulted afterward and that's what sparked rolling in dough. So we'll come back to that and we will come back to because I started to get very angry at the platitudes that I had grown up hearing.

8:33Jenny Blake: Like do what you love and the money will follow. Yeah, if you love agentic AI, great, you know. And I do now, I'm like, I'm all in on that scene. But for years, I felt like I was in the desert, the wilderness. I'm using all these metaphors because I could not get traction no matter what I tried. and the only thing I could do was write and share my frustration on rolling in dough and I can look at you from the outside and just know that it's not the end it's really the start of something much bigger and yet when you're in it it's almost enraging when somebody says oh just chin up and it used to piss me off I kind of like lost friendships over rolling in dough because I kept wanting me to cheer up already.

9:18Jenny Blake: And I wasn't there. And I was single for a very long time in my 20s. And I remember people would say, you'll find the one. And I just thought, but what if I don't? You cannot guarantee me that. My life path, my soul may have different plans for me. And you cannot tell me, you cannot guarantee me that I will somehow find the one, this magical one. And I think that sometimes, I think after now these last six years, We're no longer as patient with these like meaningless platitudes about life and work because we've all been through such a ringer. So, yes, I have many more thoughts on that. My relationship to anxiety has turned a strange corner.

10:02Jenny Blake: It's kind of relating to that. I've always loved new technology. I grew up in Silicon Valley. And now that I'm seeing what's possible with agentic AI for small business owners, my third book is called Free Time. It's all about setting your time free through smarter systems. My second book, Pivot, did better with like big companies. And that's all about if change is the only constant, let's get better at it. For the first time in six years, I feel like my whole career has been preparing me for this. And I feel that my body went from a dial up internet these last three years to now there's a fiber optic cable running through it of energy and ideas and learning and I'm engaged.

10:45Jenny Blake: It is almost so good. This is what had been missing the last few years that I'm afraid. So now my anxiety is the memory of how hard the last several years were and just thinking, really, like when is the other shoe going to drop? So I'm trying to take it one day at a time, just from the other side of the coin of breathe. It's one day at a time. It's one day at a time when things are horrible and I feel hopeless and helpless. And it's one day at a time when they're exciting and thrilling and I can barely sleep and I dream of prompts and electric sheep. And so I'm trying to expand while being so afraid to just end up back curled in a ball, no energy, nothing to give, not shining, absolutely wondering the same thing that you opened to this with.

11:36Morra Aarons-Mele: Okay, well, let's start. Let's give listeners some orientation around what rolling in dough is. You went to UCLA. I know you were in a sorority. Yes. And take us through the trajectory a little bit and warts and all to this day.

11:57Jenny Blake: Yeah, well, I loved writing and I loved computers since I was little. I started a family newspaper when I was 10. And I sent it monthly all through high school. I was always into technology. I did go to UCLA. I left a year early to work at a startup company in Palo Alto as the first employee. It was a political polling company now acquired by YouGov America. after two years there when I hit a plateau I moved over to Google I was doing AdWords product training and even teaching not just teaching Google Analytics and HTML to Googlers but I started a side hustle teaching small business owners HTML and CSS so that they could be empowered to update their websites even when they wouldn't have to hire someone expensive and so what's weird is that little teeny side hustles coming back right now in this moment after five and a half years at Google, I just, there was too much bureaucracy for me, like too many meetings and emails and approvals.

12:53Jenny Blake: And I just felt I had started a blog on the side, of course. And so I left in 2011, moved to New York City, where I had been trying to get since I was nine, when I first came here. And I would say that the first 10 years of self employment, I thought I was pretty good at it. and only recently I look back and I think, and I also got really lucky. I was kind of riding the economy wave of 2011 up until 2020. When the pandemic hit, what was your business? Oh, coaching, speaking and licensing. So when pivot came out in 2016, that really took off. And I did a lot more keynote speaking, I started licensing the IP to companies like Google and Chanel.

13:40Jenny Blake: And I even built out a coaching team because I couldn't handle the one all the one on one. So 2019, my business peaked, I actually felt I had momentum. And unbeknownst to me, it peaked because I also bought an apartment that year, got married the year prior and brought home a puppy in December of 2019. So I was kind of and I was maybe mid 30s, when all that was happening. So I got married when I was 33. And when the pandemic hit in the first two weeks, I lost 80 % of my slated income for the year. So that was very shocking. But I had a lot of energy. I thought, well, I wrote a book called Pivot.

14:20Jenny Blake: I can jump in, I can help people. I started podcasting every single day for three months on the Pivot podcast. And when I realized that all my corporate work, it was almost like I call it when the financial tides recede. When the corporate financial tides receded, and I wasn't running around serving corporate clients, what washed up on the shore was really my passion for small business owners. And I had had a community for almost, I don't know, eight or nine years. But it was always behind a paywall. It was always behind the scenes. I felt almost imposter syndrome, like who am I to talk about how to run a business?

14:55Jenny Blake: but when toward the end of 2020 I was so exhausted my husband's Lebanese there's been so much tumult in Beirut and Lebanon that I just wanted to do something for me and that's when the seeds of free time sparked and I thought you know what the corporate clients they've all canceled on me why am I chasing them and and I made a really big bet on the next iteration of my business and still today, Pivot and FreeTime are the two skis, if you will, the two topic skis of what I do. But my heart is really with the solopreneurs and the creatives, I have to say.

15:31Morra Aarons-Mele: And how has it been for you economically and business-wise since 2019?

15:40Jenny Blake: Can I just say like abysmal? I mean, I don't want to be ungrateful. I think if I was not married and the sole breadwinner and having an apartment mortgage and a dog, a German shepherd, it's he's not small. He eats a lot. He has vet bills. I don't know what I was thinking. Like, that's the Delulu that just had me thinking, yeah, do it all at once. Like business was booming. I can afford this apartment that my dream, it was my dream to have an apartment someday in New York city. And I, you know, and I love my husband and I love my dog, but I wasn't prepared. It was almost like then to have all my income wash out at the same time.

16:19Jenny Blake: I mean, not all, but most of it. Suddenly I was absolutely drowning and I was already drowning in just householding. I never thought I would get married. So I was already drowning in just cohabitating with someone and having a dog and how my life had to change with a dog and a husband. And, and again, being the soul breadwinner my husband's a fine artist and I'm totally at peace around that because I love building my business but the last six years have been so difficult and I have not been able to out earn all this responsibility and as I was saying the reason I started rolling in dough is because in the summer of 2023, I lost a six figure licensing client that had been with me seven years.

17:09Jenny Blake: And with all the keynotes gone, because events were gone, or for the most part, I mean, little little ones here and there. That was really the last straw. Like I had tried to be resilient through 2020 and even 2021. By the summer of 2023, when that last kind of big contract domino fell, And all of a sudden, not only was, I'll just say it, 150K income instantly gone. That organization also used to hire me for sub events. So another 50K, then another proposal fell through that would have been 100K. And I just like saw it all go away. And that's not the kind of income that you can replace overnight with like$5 subsec subscriptions.

17:49Jenny Blake: I'm grateful for every single paid subscriber I ever had. You can't even replace it with one-on-one coaching. And that's where all I could think to do was write. And I knew, I felt very passionately that nobody was saying out loud how hard it really was. Because for small business owners, it's also a catch-22. We don't want to be a self-fulfilling prophecy. If I talk about how hard it is, I'll scare future business away, future clients. And I'm sure I did. But for me, for those two and a half years, because rolling a dose paused at the moment, we can get to that. I just felt I don't give a shit anymore.

18:26Jenny Blake: Someone has to say this. Somebody has to say it out loud on an ongoing basis and not when they say I had$5 in my checking account and now I make eight figures a year. Right now I'm a millionaire. Yeah it's like I was so sick of that too and I didn't want the shiny story on the other side. People always say right from the scar not the wound. Yeah, but then you forget what the wound is like, and you forget how hard it is. And you forget that you're not alone when it's hard. And I purposely learned the skill of personal essay because I didn't want to be the expert anymore. I felt I had nothing more to say as far as how to do something.

19:07Jenny Blake: I could only say, here's my experience. I hope there's something in here for you. Or as you said, here are the resources and books and quotes giving me life. I hope you take something but as my writing coach taught me I had to learn not to tie the post in a shiny bow at the end and like and now here's the five-step process that you too can get your laundry done

19:33no um I know I know I have so much to say I mean I had one of my favorite conversations ever

19:41Morra Aarons-Mele: with a with a fellow content creator once and I was like you know on the internet everyone looks rich. And, you know, that's shiny hair, with shiny hair. That's part of the game. And I so relate to what you said. It's, you know, preaching from, I actually, I guess taught at Harvard Divinity School about boundaries in public speaking when you talk about sensitive topics. And, you know, one of them pastors in training said, you know, I was always raised with preach from preach from your scars, not your wounds, because you don't want to hurt anyone's boundaries, right? You don't want to make them feel uncomfortable.

20:19Morra Aarons-Mele: But I think when you talk about the truth, especially about money, it's the opposite. People feel so seen. It's something I've been struggling with this year because I'm still out there as a speaker. I'm still out there as a coach, as a leadership trainer. But the truth is not shiny. And, you know, in June, June 30, 2025, I lost over$400 ,000 in revenue one in one day. And then at the beginning of this year, another 200. So these are big numbers that we're throwing around. We're really lucky to have been able to bring in big numbers, but it's, it's in my experience, humiliating. That's the word that, that I want to use.

21:09Morra Aarons-Mele: I was, um, unlike you, I had an incredible pandemic because I, I owned a business that really benefited from the pandemic. Um, and then my mental health speaking business was on fire, just on fire. Um, and my work until I would say about the end of 2023. And then it started as the world changed a little bit to dip. But I did really well for a really long time. And I thought I had it all figured out. And the lesson in both humility, but also humiliation of this past year,

21:49Morra Aarons-Mele: it's something, I don't have the word for it. It's definitely unresolved.

21:53Jenny Blake: Well, those are two good ones that I felt so much too humiliated I felt humiliated amongst fellow, like my peers, entrepreneurial friends who were kind of, I felt just looking, watching me flail. And I started to feel like I didn't even belong at these events, masterminds. And the humbling. The humbling. I have come to think of it as the great humbling. It's like, and I think the author, Elizabeth Strout, says at least once in our lives, we will go through a great humbling. She said something like that, that I now keep with me. I'm curious for you. Yeah, like when you lost the second one, because it's the first one is shocking.

22:36Jenny Blake: And yes, they're big numbers. And also, you know, 30 % for taxes, operating expenses, people, staff, lawyers, agents, all of it. There's a lot baked in to the big numbers. And we don't have salary and benefits and health insurance and a lot of stuff. My mom to this day tells me I should still go get a job. I'm 15 years in. She just doesn't care what I'm doing. It's like, go get a job, you know, to her. That's scary. Trust me. But for you, when you lost the second one, and it sort of truly initiated the dark night at the soul, at least dark night at the business soul.

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27:41Jenny Blake: My phrase of the year is ego death.

27:48Morra Aarons-Mele: I realized somewhere along the way that I, and I wrote a book called The Anxious Achiever, so this is very on brand. I had become so addicted to achievement and so ego driven that I hated who I was becoming. And I loved earning a lot of money and I was proud. I built a business. I sold it. I built this other business. It was doing so well. Like I started to feel like I really was better than a lot of people. And I was always looking around my shoulder. Everything was a competition and social media only made it a billion times worse because everyone looks rich on the internet. And this sort of big humiliation and great humbling, I love that, sparked in me something which I didn't want to face in myself, which is that I had to kill my ego for a bit.

28:51Morra Aarons-Mele: I wasn't doing the work that I had said I wanted to do to help people, because my mission in life is to make work work for everyone and to help people enjoy better mental health and well being at work, no matter how their brain is wired. That got lost somewhere in the like, stupid LinkedIn metrics. And, oh, wow, she has four keynotes, and I only have one. So ego death. And I want to talk about your neck, because what, what I what I had this, this was only a few weeks ago, but I've had this horrible pinch nerve in my neck for years now. Terrible pain in my neck that won't go away. And I was in a Reiki session this past summer and I saw a dragon.

29:35And I realized that this dragon lived in my neck

29:39Morra Aarons-Mele: in the form of the pinched nerve. And sometimes it would breathe with fire and sometimes it would quiet down, but it would never go away. And all I wanted was for it to fly away, but it lived with me, like in my neck. And then recently, a couple weeks ago, I was watching The Power of Myth with Bill Moyers and Joseph Campbell, which was something I watched as a kid. And Campbell says that the dragon, such a powerful figure in literature, in Western literature, is representation of the ego and i realized that this is my bruised ego holding on for dear life and it has to go wow sorry that was that was a very that's so powerful no apologies

30:27Jenny Blake: needed that's amazing yeah these our body is so smart and there's it teaches us i mean it sounds to me too like losing those contracts was also you know depending on what you believe in god a higher power redirecting you saying you're not on mission anymore even though you have good intentions is just like a divine redirect saying or jenny is that just woo-woo bullshit and in truth i better

30:58Morra Aarons-Mele: get my ass back working because i have three kids who go through college well well we could say yes I mean, sure.

31:08Jenny Blake: But I also think our body is such a teacher and a healer. And I do think our bodies also know when we're off track and they speak up. So it's like, if we're not listening to the signals in the world, if I won't even say the universe, we're not listening to those signals that our body kicks in. I do think there is a larger intelligence at work in our bodies that know when we're off track, when the whole system is off track. And I'm sorry to hear about the nerve pain. That's what you were mentioning that I wrote about the summer after I started rolling in dough. Well, what happened was I was getting down on myself like, I'm just being lazy, I need to work harder, all these messages that I had spent a decade rewiring, especially when I wrote the book free time, that's all about operating at the intersection of revenue, joy and ease.

32:00Jenny Blake: It's arguing for, you know, working less and setting our time free through systems so that, you know, not so that we get more done. I don't care about efficiency. I mean, I care about it for my own time, but just so I can be at Central Park with Ryder, I don't care. I work 20 hours a week. And I think that's plenty. I think that's full time. But when I when that wasn't working, I kind of had that gremlin that you just expressed of like, why aren't you just being lazy and shame on you, the reason you're struggling is you're not working hard enough everyone else is get your shit together and so for a for a quarter in q1 to use biz speak of 2024 i just doubled down and i had a 50 000 tax bill that came out of nowhere because of weird stuff i had done when selling a house and investing because i hybrid published free time lots of money was flying around in 2021 I got the tax bills.

32:57Morra Aarons-Mele: Every entrepreneur is listening and being like, oh my God, the tax bills. Yeah.

33:03Jenny Blake: And it's not like we don't plan, but it's like sometimes it does surprise you. So I doubled down, tripled down, ran around like a mad woman. And all the while my neck had started hurting. Then it started to be where the dual action Advil's four hours increments wasn't working. Then by the time I was set to facilitate a half day strength scope session for this Google team in Seattle, I woke up that morning, I had been writhing in pain all night in the hotel room. I couldn't sleep. I was laying on the floor with my feet up on the bed. By the time I woke up that morning that I was supposed to facilitate, that they had flown an entire team out for it, that I had flown out for.

33:42Jenny Blake: I was so nauseous. I couldn't stand. I wasn't even done building the slides or the resources, Google Doc. I had to call my husband. He had to open the slides. In my nausea, I had to walk him through how to finish these materials. And then I had to pray that somehow, some way I would go from that state to somehow being able to fake it till you make it facilitate for four hours. And truly, by the grace of God, like, or whatever you believe in, I was able to facilitate. I got back home to New York. I had two more events to show up for. And I'm like, come on body, like, give me just this one more week, these two more events.

34:26Jenny Blake: I had a VIP day with a free time client. And then I had like a career development symposium thing, what was going to be great connections for future work. And I'm in searing pain prior to both, but I like charge through. I also don't want to let down my clients. I don't want to cancel anything at the last minute. And I need the money. and you know where this story is going sure enough two days later after I finished the last last thing of this three-month sprint working in a way I know doesn't work for me I woke up on a Sunday morning I went to take Ryder out and as I put on lip balm I couldn't purse my lips I couldn't like smack my lips together I went to take a sip from my water bottle I couldn't it dribbled out of the side of my mouth.

35:15Jenny Blake: And we get outside and we're walking. I'm like, I'm kind of dizzy. I can't, I can't see straight. I can't, I can't drink water. I'm drooling. I'm like, what is going on? I took a selfie. And when I came home, I said to Michael, like, can you look at my face? I can't do certain things. And the look of fear that washed over his face. He thought I was having a stroke. We rushed to the emergency room. They rushed us, you know, usually wait four hours. They rushed us in for triage. And my pinched nerve in my neck had created Bell's palsy, which is facial paralysis on half my face. Some people can have that for 10 years, if not forever, because half my face was paralyzed.

35:57Jenny Blake: Thankfully, mine went away with a course of steroids and a muscle relaxer. So we spent all day in the ER. And two days later, Michael said, that's it. I'm walking you to Equinox on Monday. He took took the subway because I was like, it's too expensive. No, I can work out at home. I can do other things.

36:17Morra Aarons-Mele: Equinox is a lovely fitness center, gym, spa, FYI for people.

36:23Jenny Blake: I pay for the women's executive locker, which also includes a locker, 24 hour laundry service, tea, fruit. I pay like$450 a month, like to me, the way I was raised, that is in effing sane that's insane like my mom if she knew she'd have an absolute heart attack

36:42Morra Aarons-Mele: if she knew this was my gym membership but I couldn't not do it like I had just spent five

36:47Jenny Blake: hundred dollars at the ER so which one do I choose and now I call it the spa fest because I I go I read I get a little important work done I work out I I swim I do the steam room and sauna I never would have done those kind of self-care things. Yeah. And then I come home and I really spend the whole day there. That's why I call it the spa fits. And it's cheaper than a WeWork, I'll tell you that. Well, there you go. I know. I don't even, so on the one hand, it's expensive. And on the other hand, it helped heal me. So I mean, that's a very long-winded story in response to your nerve and neck pain.

37:25Jenny Blake: But to me, it was my body. I've always known it keeps me on a short leash. And that was my body cracking the whip and say, don't try me. You know, if you're going to work like that again, I already you already know. I already knew that doesn't work for me. And I overrode it anyway. And once again, I was proven that that is wrong for me, even if to other people it looks lazy or entitled or any of those other things.

37:48Morra Aarons-Mele: one of the things that I've always respected about you is um I think you said I'm gonna try to I think you said in an interview that you're just not great at corporate life or at corporate working and that you you do work more limited hours than a lot of people you have a lot of systems um around it um and and I'm the same I oh my god I mean the way that I work and I I've written books. I wrote a book called hiding in the bathroom about largely how to be an entrepreneur when you really just want to hide in the bathroom and not network. But, you know, there's that extra thing of when you're what I call an atypical achiever, you, you figure out the formula that works for you, even if it's not societally sanctioned.

38:38Morra Aarons-Mele: And you kind of keep it quiet because like people are judgmental. And as long as you're doing well, great and then maybe you stop doing well and then you think is it because I only work 20 hours a week is it because I do all this stuff and I didn't for me it's if you had climbed the corporate ladder if you had worked at Google like a lot of my friends who are now like wealthy beyond belief and are like done I think what your life would have been totally everything you just said even

39:11Jenny Blake: from hiding in the bathroom, which I do all the time.

39:15Morra Aarons-Mele: I know you wrote a substack about it.

39:17Jenny Blake: Oh my God. Yeah. I'm there all the time. And I wait till someone jingles the handle and then I'm like, Oh, okay, I'll be right out. Um, yeah. And I feel bad too. I feel bad saying, Oh, my body shuts down. Um, even though that's true for me, because I feel bad because maybe

39:34Morra Aarons-Mele: in corporate who work 50 hours a week.

39:36Jenny Blake: I know a lot of people in corporate who have chronic illnesses they can't explain but I feel bad when people are like like you know working 50 hours a week or or um maybe don't have as much choice or like I took loans from my family the last few years when I need I was very privileged to be able to do that not everybody has that safety net not everyone can take the risks that I did knowing I won't end up homeless it's so sometimes I just feel bad to talk about this stuff because I know how many people not to mention not just here in the US, but like around the world, have it so much harder, are going through immense tragedy, famine, war, horrendous situations.

40:18Jenny Blake: So I have a hard time talking about any of this sometimes, because I just think, man, I'm in the lap of luxury, like, be quiet. Yes.

40:27Morra Aarons-Mele: And I think this show, it goes without saying, assumes a level of privilege. But that's okay.

40:36Jenny Blake: yeah and I love what you said about it's it's so easy to question you how did you put it you said like uh these alternate strategies you had a much better term for it atypical achievement yeah atypical achievement and yet it's something else it's like the non-typical strategies but yeah I think that's so much of the work is also reconnecting with like well this is what works for me and trying not to apologize for it. But it's really hard. I think this is part of the humbling and humiliating nature when you're down is that everybody's got advice. And it's really easy to look from the outside and sort of point to what you might be doing wrong when it also may be a question of timing, or patience or waiting for the next thing to emerge.

41:22And it's hard to

41:24Jenny Blake: refute even advice I know is wrong for me when I'm not doing well, because exactly as you said, too, it's like, oh, if only I'd stayed in corporate the last 15 years, my clothes wouldn't have holes in them and olive oil stains. And, you know, I'd have a house cleaner. And there's like so many things I have sort of bougie things, but that I have sacrificed. Yeah, to stay on this creative path or to have freedom with my time. And with how I spend my day.

41:51Morra Aarons-Mele: Yeah, it's a it's a It feels like a tough decision. I like figuring stuff out with other people. And that's why I like Notion. Notion is the AI workspace where your team's knowledge, projects, and agents all come together in one place. Teams using Notion move faster and they cut friction and cost by consolidating tools and they stay aligned. But Notion is really good for people because you know what? You put your idea down, and you put your rough draft down in Notion, your colleague can access it, hash it out, give feedback, and it's all there and organized. Is it possible for AI to make room for more human connection, not less?

42:36Morra Aarons-Mele: Notion says yes, and it will help you do your best work. Learn more about how Notion can support your business at notion.com slash achiever. That's all lowercase letters, notion.com slash achiever and try Notion today. And when you use our link, you're supporting our show. You know, I love mushrooms. I am fascinated by them. One of my favorite things to do is in New Hampshire to go on mushroom exploring walks with a renowned naturalist, Riley McHugh. Riley has taught me to put on my seeing eyes. And when I do, I see purple mushrooms and red mushrooms, big mushrooms, gross mushrooms, cute mushrooms.

43:20Morra Aarons-Mele: And I was thinking about the holidays upcoming and, you know, how we use mushrooms as a decorative theme. Think about it. You probably have a mushroom ornament or a little mushroom figure that you may put out sometime in the fall or holidays, mushrooms. If I had an online store, I would sell all manner of decorative mushrooms. I know it sounds silly. And I would do it on Shopify. Shopify is the platform for a record-breaking, reliable holiday selling season at every stage. There's a reason why so many businesses thrive on Shopify. You can easily sell everywhere people shop, online, in person, across social media, even in AI chats.

44:03Morra Aarons-Mele: If you launch your store before Black Friday, a time of year when more people are already shopping and ready to buy, you can take advantage of the extra online traffic. If you're ready to launch your business before Black Friday, go to shopify.com slash anxiousachiever and start your free trial. shopify.com slash anxiousachiever to hear your first. You know, the other day I was talking with my friend who is both certified financial planner and a financial therapist. We were talking about money and emotions. Money is way more than dollars and cents. It's emotional, right? And I'm trying to teach my kids to have healthier emotions around money than I did.

44:47Morra Aarons-Mele: But I'm getting better every year. And part of it is that I use Monarch. Monarch simplifies, identifies, and helps me have a plan for my money. Monarch is like having a financial advisor in your pocket. It has easy-to-read diagrams that help me visualize exactly where my money goes each month. And it has investment views so I can compare my portfolio, say, to how the S &P is doing. all kinds of great tools that help me frankly take some of the emotions out of money and make it more practical and working for me. Most apps only tell you what you've already spent, but Monarch helps set goals, map out big purchases, and see if you're actually on track before it's too late to adjust.

45:34Morra Aarons-Mele: You can write your own money story with Monarch. Use the code achiever at monarch.com and get your first year of Monarch Core at half off just$50. That's$50 off your first year at monarch.com with code achiever. Okay, so I want to get to your Mad Libs because I want to talk a little bit about, I do want to talk about AI at some point, but I want to talk about what gets you through the day. You, it seems to me, are so good at building in, and you wrote a whole book about this, but like building in strategies and inspiration that works for you to get through a hard day. Spoiler alert, I'm not good at it.

46:21Morra Aarons-Mele: I have depression. I spend many days just being like, I have to check out for four hours, especially when career is tough. It's like a double whammy. Like I'm very triggered. My depression is very triggered by career failure. And then when I have depression, I find it hard to get out of my own way. I'm working on it. I'm getting better. I exercise a lot. But you have some strategies. And I want to start a little bit with your less than ideal day Mad Lib, which was inspired by your ideal day Mad Lib, I think. Yes. Talk us through the idea. I'll link to it in the show notes. But talk us through how you get through a less than ideal day.

47:04Jenny Blake: Well, I can so relate to that feeling of just barely able to get out of bed, like barely able to function. For several years, the last few years, I felt I was just literally just hanging on by my fingernails. And that was triggering for some people. I remember saying that to a class of Stanford GSB students. And they gave the professor feedback. They were like worried about me and that that was very concerning and activating that I said that. Oh, interesting. yeah that was really interesting so I'm like oh should I not maybe I say too much but I guess I just want to be real and shouldn't students know that like it's not always up and to the right

47:46Morra Aarons-Mele: in life my friend Kate Woodson would say that's a trauma response they can't it's it's activating

47:54Jenny Blake: for them and yeah and um part of rolling in dough is the study I would like to teach a class on this someday. I have dreams of like teaching at Columbia, a class on flopology, which is like a prolonged, I define it as a prolonged failure to pivot. And I have already a syllabus and everything. But I love it. What gets me through the day, just like you, I mean, exercise helps something even 20 minutes of movement, even when I don't feel like it. But when I'm really down, I can't even get myself to do that. Writing morning pages, either written, I use a remarkable tablet or with voice dictation. My husband gave me that idea on Otter or I use granola now.

48:38Jenny Blake: I love granola for my notes. So morning pages helps kind of just a shower for your psyche, for one's psyche. Swimming has been really healing.

48:51Jenny Blake: and a lot of free time was about permission slips it's just like you have permission to do nothing today or you have permission to be bad at email for as long as you need to after I had bob the next bob the neck throb that led to the bell's palsy for the first time in 20 years I did not care a lick about my email inboxes I simply didn't care anymore I had been guilty I call micro guilt for 20 years, constantly people pleasing in my inbox and fawning and apologizing that I was late and slow to respond because I always wanted to put so much care. And that phase following the Bell's palsy was so clarifying.

49:32Jenny Blake: I didn't care anymore. My job is to heal period, end of story. Nothing will function if I don't go to the spa office every day and put myself first. and rolling and dough is really I think rolling and dough itself was triggering for people because it's really studying the shadow of life but specifically small business it's studying failure flops regret guilt um all these things like ego death and for 10 years when I was coaching career coaching, I gave clients this ideal day Madlib. And that's one of my favorite exercises. It really still is to this day to help someone set a vision. What does success look like one year from now?

50:17Jenny Blake: But I realized with rolling in dough.

50:19Morra Aarons-Mele: And what's on give us some questions that are on the ideal Madlib just to give us a sense.

50:24Jenny Blake: You roll out of bed at blank o 'clock, and you fill in your ideal wake up time, you stretch your arms and look out the window and see blank. You put on your favorite blank item of clothing and head downstairs where blank is waiting for you. You know, so I found as a...

50:45Morra Aarons-Mele: This morning for me, it was dog diarrhea, but okay. Oh my gosh, yes.

50:49Jenny Blake: That happened to me on New Year's Eve 2020. And I thought, is this going to be a bad sign for the year? And surely it was. When I was even doing career programs at Google, I noticed that people had a really hard time identifying what they did want, what success looks like. And so the Madlib is a way to just ease you into what does a really great day feel like? And so the one I created on rolling in dough is like, what if we could just say out loud, what's not working? You know, just give people a template to put language to maybe a hard era, a flop era, if you will. A flop era. Yes.

51:29Morra Aarons-Mele: I'm going to, my year, this is your Mad Lib of rolling in dough. Nearly one year ago, I hit a major dip when blank. I didn't know what else to do. So I started action step. I had a hunch this could help ideal outcome. So despite the obstacle, I began verb.

51:49Morra Aarons-Mele: My friend or family member reacted by saying, and then, um, you go through your magical thinking you go through trying to be grateful even though things

52:01Jenny Blake: are really hard why aren't you enlightened why aren't you enlightened what you admitted

52:05Morra Aarons-Mele: you realized you had a lot of ambiguous grief around waves of insecurities I I love it I love

52:14Jenny Blake: it so much and um thank you it's so fun hearing you read it I haven't even read these in two years Oh, they're so good.

52:24Morra Aarons-Mele: You have to read it. I think one of the last questions is so good. It's, it seems around the time that you're sort of like coming to a bit of realization and you say, there was one thing I forgot to say to my career these last four years, blank. What does that mean? Oh, bless you.

52:46Jenny Blake: Thank you. Well, I think for me, I had not said thank you. Like I wrote a dope post, the one thing I forgot to say to my speaking career. And I show my trip at travel stats absolutely tanking just the way my revenue chart did. And I really forgot to say thank you. What a beautiful time that was. What a rewarding era of my life and my career. And I also felt like this may never come back. Like my glory days might be behind me. I even interviewed a mentor about, do you ever feel sad if you feel like, are you a one hit wonder? Because his second book, The Coaching Habit has sold over a million copies.

53:31Jenny Blake: And I, and for me, Pivot has sold less, but like many more, you know, maybe Pivot has sold 60 ,000 copies and Free Time has sold, I don't know, 7 ,000, which is still remarkable by most book sales standards, but not nearly what my first two books had sold. And I was having a hard time thinking, is my biggest success behind me? And just like you started this podcast conversation, you know, maybe the platitude of the pat on the head is, no, it's not. You're destined for much greater things. But I kept thinking, well, what if it is like, there's a lot of one hit wonders, they do their one thing, and they never, they spend the whole rest of their lives trying to surpass it.

54:13Jenny Blake: And I really started to feel like I was high school quarterbacking my success era. And like you said, maybe not as even grateful or recognizing how incredible that really was. So that I guess that's what I wanted to say to my career was just thank you for those experiences, because I keep focusing on having lost them. And what if I never get them back. I still don't sit here and say, but my next book will surely sell 100 ,000 copies or a million like, nope, it might not. And now my framework for embarking on any next project is am I willing for this to flop? Would I do this anyway, if it's a flop?

54:57Jenny Blake: And then to me, that's a freedom. Go right ahead, because I won't be going into it with any Delulu thinking that this next project is going to be the one or this one's going to save me. No, it might not. It probably won't. Especially a fourth book. Like we know that. I mean, I love books. I cherish them. They're everything to me. But books every year seem increasingly harder to sell if you don't have $500 ,000 to throw at your launch, which like that's what I get compared to spare around.

55:25Morra Aarons-Mele: Did you fill in any of the Madlib?

55:26Jenny Blake: I want to know what your, what would you say to your, What would you say to your business these last six years or the duration of it?

55:37Morra Aarons-Mele: 20 years.

55:39Jenny Blake: 20 years.

55:40Morra Aarons-Mele: So I would say, well, not 20. I mean, I would say that I was an accidental. Yeah, my career. I was an accidental entrepreneur. I started freelancing in 2009, incorporated my business in 2011, sold it in 2021, finished with it in 2022. and then these past four years have been really working in workplace mental health and leadership advisory. What I would say to my career, starting at when I was, I thought about this when I read your Mad Lib this morning, is that there was a phase of my life, probably 35, 36, 37, 30, yeah, where I was doing really well and I invested so much in how I looked. I had beautiful clothes.

56:31Morra Aarons-Mele: I had beautiful handbags. I flew to New York to get my hair done because God forbid I got my hair done in Boston. And the way that I was raised made me feel like I had finally made it But what I really felt proud of was the rooms that I was invited to be in. And I can even smell how I used to smell when I would always take the shuttle. I live in Boston. I'd always take the shuttle to New York or D.C. and be in these incredible rooms. And now I sit home in my sweatshirt, and I'm like, I'm grateful for those times. I'm sad but I'm really grateful and I think if it never happens again I will be okay my dear friend and mentor you mentioned one of yours

57:26Jenny Blake: my Callie Yost you know she like me does kind of you know Callie I love Callie what a dream the two of you oh I didn't know that okay Kelly is the wisest I mean she's been on the show

57:43Morra Aarons-Mele: listeners but like you know and she's the world's expert in high-performing flexible workplaces but she's been doing it for 30 plus years and it's been lonely and now it's not lonely obviously and she just tells me like what you do really does matter and someday maybe people will cotton on and if they don't are you still willing and and I sort of I'm like I'm still willing you know I have very real financial concerns because I do have three children to put through college like you I have a big mortgage.

58:26Morra Aarons-Mele: But my choice this year is to kill my ego and lean into the work. If the work a year from now is still not remunerative, then I have to figure this out. I don't know. But I'm not quite willing to give up yet. And I love my career. I'm proud of it. I feel like I feel like I did a lot and if it's over you know it's over. Wow that's beautifully said and thank you for sharing that and I love I think we have been

59:08Jenny Blake: doing this long enough to also trust our gut and it's like me too even as bad as it ever got my gut always just said, keep going, find a way. Like I still wasn't willing to give up. And so I just love hearing that in you, like that grit and perseverance, even though of course, grit, you know, there's the bad sides to that too. Yes.

59:34Morra Aarons-Mele: Grit can be glamorized, you know,

59:36Jenny Blake: grit is a bit like, it's a bit like resiliency. It's a bit like authenticity. It's words that we say, but we don't really mean. And it's so annoying when you're like, what if I'm not? I don't know. I didn't. Yeah, I don't love the word grit. Even as I said it out loud, I knew like, wait a second. It's not that but it's just a patient persistence. And trying to find like, I love how you're just noticing this ego death. And it does ego death, it does have to happen to even have a chance of the next phase of you and your life and your career to emerge. And it's also saying, okay, and there's financial concerns.

1:00:19Jenny Blake: So I'm giving it a year. And if nothing has changed in a year, I'll reevaluate. But for now, I'm going to be patient. And I find that to be really helpful too. And that is why I did pause rolling in dough because I was putting so much creative energy into writing these two essays every week. the money wasn't coming in and I had I had just run out I was out I was out of every last drop of savings I had sold oh my last cord was like google stock that I had held on to for 14 years after leaving and I still regret that I sold that I still regret that I had to let it go but I felt like I was maybe still corded to that part of my identity almost like an umbilical cord um I had to cut it had to move on I had to have this hope maybe delusional as you've said that oh there's more out there for me I can't I cannot just grip squeeze everything so tightly and be so afraid that nothing new will come in um but but ultimately as of December like I didn't have another dollar's worth of time to wait because I was not, I was going to rent out my apartment, try to find a tenant starting last July.

1:01:37Jenny Blake: We couldn't. So we had to take it back off the market over the holidays. So that meant I had six more months of this mortgage over my head. And that's when I decided, okay, kind of like you're saying that what my time was up. Time's up now. I need six more months of this, of, of really high income. So I just announced I'm going back to business basics on rolling and dough. And And I was really sad to do it. I felt actually like losing a cherished connection and community. But I couldn't. I couldn't put my energy into writing when I couldn't pay the bills in my house. So I had to do the responsible thing and refocus on my core business.

1:02:14Jenny Blake: And I'm just grateful to have any iota of energy to have been able to do that. And now, you know, I do have momentum. It's not magical momentum. It's just the showing up and redirecting my energy. and maybe it was cathartic to have rolling and dome. So glad it exists. You know, I don't know if I'll post there again, but I'm so grateful that it helped me build the bridge through this, the void, really.

1:02:40Morra Aarons-Mele: It was a season.

1:02:41Jenny Blake: Through the abyss.

1:02:43Morra Aarons-Mele: Yeah. Through the abyss. So I have two questions then. I want to hear about what you're doing, but I think what listeners might be asking is, my sister actually said this to me. She used to be a recruiter. She said, because I said, like, I'm out there. I'm hustling. Everything I've done for 20 years that always worked isn't working. And she said, it's not going to work right now. Let it go. Come back later. Don't spend the social capital. Don't don't waste it. No one's hiring. And I thought, oh, I think that's good advice. So so talk to a listener who's sort of like at their wits end because they are hustling and they are trying, give them permission.

1:03:29Morra Aarons-Mele: You're so good at that. And then we'll talk about, we'll go out on what you're doing now.

1:03:34Jenny Blake: Well, it reminds me of a Zen phrase, don't push the river. You have permission to lift the oars. I'm now mixing my Zen, favorite Zen phrases. Lift the oars, like stop pushing the river. There's a flow, there's energy channels and actual market demand channels. And it's effing chaos right now. So I mean, one permission slip is you have permission to just stop beating yourself up. I mean, that's not permission, but an encouragement. Another Buddhist phrase I love, nothing is perfect, personal or permanent. But I think most importantly, you are not alone. Everyone, if someone is not in chaos right now, they just don't know what's coming.

1:04:21Jenny Blake: like I my assistant was out of office for two weeks on vacation and I automated 90 % of what she does while she was gone and now we're talking about how we both reshape our roles and that's because agentic AI developments started releasing while she was on vacation like I wasn't doing it on purpose I was just oh we can do this we can do this we can get this done and I thought oh my god this is coming and the people who aren't already at their wits end and uprooted like may experience it later, kind of like I went through it. Some people, you know, the stay at home moms with young kids went through it in 2020, when they were losing their mind, not stay at home, sorry, working moms, and people work from the home, let's be real, like, there's no such thing as stay at home, you're working in the home, maybe some had a full time job while raising small kids, they hit their wit's end in 2020.

1:05:11Jenny Blake: I hit mine in 2023. When all the tech companies that used to hire me started tightening the belt, you're hitting yours now, some are going to hit it next, Like we are still going through this collective upheaval and whoever's out there with it, you're not alone. And nobody knows what's next. Not even the people inventing all this tech. So we're all in it together. And that's it. We're not in it. We're all in it together. And you cannot force a solution out of thin air where it doesn't exist. So it does require some patience.

1:05:43Morra Aarons-Mele: It's like a radical acceptance. Yes. You know, I think we entrepreneurs are used to it because that's the nature of our lives. I have good friends who worked at the State Department for almost their full tenure, who gave their lives to making this world more peaceful, and they got fired by a madman.

1:06:08Jenny Blake: So I think - Instantly, with no respect, and they can't pivot into another world. The roles were eliminated all at once. Right.

1:06:16Morra Aarons-Mele: And it's unfair and it's out of their control. And so I think you're right that there is this. And those of us who've walked through life so privileged and like, I went to a good college. I did all the right things. And now you're telling me I'm useless. How could we not burn and grieve all of that? Jenny Blake, I want to thank you so much. Thank you for your wisdom.

1:06:42Jenny Blake: Thank you so much for having me. It's been a real joy to be here. and huge thanks to everybody who's here listening.

1:06:51Morra Aarons-Mele: That's it for this week's show. If you like the show, follow us and tell your friends and please leave us a review. It really helps the anxious achiever get found by people just waiting for our content. I'm your host, Maura Aarons-Mele. Lots more to come in the next episode. Thank you.