Maureen Wiley Clough: Aging Out of Corporate, Career Reinvention After 40 & Why Honesty Comes at a Price | Be Yourself Podcast

Maureen Wiley Clough

Host of It Gets Late Early — on ageism in corporate, going all-in on your side hustle, why honesty costs you, and career reinvention for women in their 30s and 40s

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36 minutes

Ageism · Career Reinvention · Personal Brand · Podcast

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About the Guest

Maureen Wiley Clough — Host of It Gets Late Early, Midlife & Career Empowerment Creator

Host of It Gets Late Early, a podcast consistently in Apple's top 20 for Careers — she started in broadcast journalism, spent years in tech business development, and launched her podcast while still employed at a youth-oriented startup, which promptly laid her off for it

Rather than return to corporate, she went all-in on her platform, partnering with brands and speaking on career reinvention and ageism — building a community of midlife professionals navigating a system never designed to keep them

Podcast

It Gets Late Early — Top 20 on Apple Podcasts in Careers, dedicated to breaking the silence around ageism in the workplace

Background

broadcast journalism, then tech business development building channel partner programs, now a full-time podcast host and creator

Why She Started

called a "dino" at 37, she noticed nobody was talking about aging out of corporate — launched the podcast while employed, and was laid off within weeks

What She Does Now

brand partnerships, speaking on career reinvention and ageism, guest co-host on the Chad and Cheese podcast, and creator-economy advocate

Key Quotes

“

What keeps me going is the thought that I don't want to be told that I become less valuable with every day I continue to breathe.

Maureen Wiley Clough

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I just couldn't live with the regret of not knowing what could have been. And that was the main number one reason I did it anyway.

Maureen Wiley Clough

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You should care much more about what you think about you than what other people think about you.

Maureen Wiley Clough

Episode Chapters

0:00 In This Episode 0:48 Why It Gets Late Early 3:16 The Problem Behind the Podcast 6:50 Side Gig vs Full Commitment 9:20 Visibility and Its Consequences 13:04 Can Employees Be Friends? 14:05 Values in Life and Work 22:34 International Men's Day 24:15 Career Advice for Women in Their 30s 29:24 Your Circle During Transformation 30:42 Building a Distinct Personal Brand 34:32 Mo's Message to the World

Full Transcript

BTW: This episode of the Be Yourself Podcast is produced by Beverly Media. Also on the show:
Roman Pikalenko — LinkedIn Growth for Climate Tech Founders & Why Newsletters Convert 7x Better →

0:00 In This Episode

Maureen What keeps me going is the thought that I don't want to be told that I become less valuable with every day I continue to breathe. And I don't want my kids' future to be hampered by this gray ceiling where people are like, "Dude, you're a has-been." I don't want them to have to race through life feeling like they have to quote make it by like 30 or they don't get on the Forbes 30 under 30 list and they're done.

Sergey Hey everyone, welcome to the Be Yourself podcast, the podcast on expressing our true selves. Today my guest is Maureen Wiley Clough. She's a midlife and career empowerment content creator, brand partner, speaker, and podcast host. Maureen, welcome to the show.

Maureen Thank you so much for having me. I'm so happy to be here and it's great to actually meet you, you know, well, not in person, but one day, right? I'm really grateful that you found the time.

0:48 Why It Gets Late Early

Sergey The first question I want to ask you is about the name of your show. A pretty successful podcast that's called It Gets Late Early. Why does it get late early, Maureen?

Maureen Because we get old real quick and time goes really really fast. When I was 37 years old at work, a younger colleague referred to me as a dino when I did not know how to put a gif in Slack. And I was like, "Hey, that's rude." And then I was like, "Wait a second. Actually, he's kind of right. Like, where are all the older people around here? Like, how am I one of the oldest people at this company? That's really messed up."

Maureen And then I started thinking about it and I was like, "Oh, wow." Actually, over the course of my career, even in different industries — because I started in broadcast journalism — that was very much the case. I thought why is nobody talking about the fact that there seems to be this sort of aging out of corporate. There are only so many rungs on that career ladder. And I sort of instinctively knew if I didn't get myself up that ladder quickly enough, I'd be a has-been. I'd be done for and I'd be pushed out altogether.

Maureen When I started talking to people about it, they're like, "Oh, yeah. Ageism is a big thing. Yeah, I'm worried about it." I'm like, "But why aren't we discussing it?" So I decided to hop on the bike and create the show. And especially in an age where we were talking about all the various benefits of having diversity and inclusion at organizations, I was like, "Dude, this is the literal one thing we all share. There's like a perverse beauty in the fact that we all will face ageism if we are lucky enough to live. So let's band together and let's figure this out."

Maureen I started the show and it's been wonderful. I mean, as you well know, growing a podcast is a long laborious process, but it has been immensely gratifying and I've met the coolest people.

3:16 The Problem Behind the Podcast

Sergey Just like a startup founder — the best startup is the one that solves his own problem. And it seems that your podcast was born out of this unfair thing that you were struggling with or you noticed. Why was there not enough people who were talking about it?

Maureen I believe that one thing that we as humans do is we think that aging is something that happens to other people and not ourselves. So I'm like I'm 29 obviously forever — like that's how I feel. That's how I kind of present myself in the world. And then suddenly you look in the mirror and you're like, "Oh yeah, I'm not that anymore." And it's a weird feeling — people start recognizing you as older than you feel, right?

Maureen I was actually working at a tech company when I started the podcast and I knew there was a risk because it was a very very youth-oriented startup. Literally when I logged in for the first day of work, I was scrolling Slack and I came across this picture in a general channel — it was a picture of a dude mooning the camera standing next to another dude cheersing with a champagne flute on a mountainside in a ski town. And I was like, "What? Who put this up?" Oh, it's the co-founder and president of the organization. Tell me without telling me that you have a culture that I'm not going to be a part of at some point.

Maureen And sure enough, within like a couple of weeks, I was out. A layoff of one. With ridiculous reasons — because I hadn't had any sort of performance situation, I didn't even have goals set. It was very blatant. I always knew there was a chance that would happen, it happened, and then I just had to make a choice.

Maureen I was doing business development in tech, creating channel partner programs, which I was really good at and liked. But there's a ceiling unless I hit VP or something really soon. And so I decided I was just going to go all in on the podcast. Health insurance — huge in the United States, huge. So yeah, I was able to just throw all my weight behind it, but it was not the way I envisioned it coming out. It was supposed to be my side hustle that was funded by my paycheck.

6:50 Side Gig vs Full Commitment

Sergey Super interesting to see so many people who take a leap because they pretty much have no other choice. We all want to have a safety net. We all want to start something as a side gig and then have it blossom into our full-time business. But if you don't go there fully, if you don't immerse yourself fully, if you don't invest all of you into this thing, it's not going to become a thing that's going to support you.

Maureen I do agree with that. I think it also is dependent on you specifically. If I were a systems-oriented person and I had all of my ducks in a row — maybe I would just need to carve out time on the weekends or time in the morning. So for some people I think it is possible. For someone like me with this bizarre creative brain who's very scattered and neurodivergent — there's just no way.

Maureen You have to be very dedicated. You have to be very driven. It's hard to do that when you have a variety of other things on your plate. But I do think there's a way to chip away at it over time, lower your expectations, right? Like have the runway be longer. It's not going to be an overnight success. Almost nothing is. And you see people who go viral overnight or whatever and then they don't even have the scaffolding to support that and so it's almost like a waste. It's going to be a long-term project. Buckle up.

9:20 Visibility and Its Consequences

Sergey You said that honesty comes at a price and it's not a meritocracy. Your podcast was rated in top 20 on Apple Careers. So with visibility there comes something else. Can you talk to this matter?

Maureen Yeah. When I wrote that answer about meritocracy not being real and about it being a risk to be honest, I really mean it in even very banal boring situations. If you're in a corporate organization and you publicly disagree with someone who's your superior, that is actually inherently dangerous for you. A lot of these people say they want public opinion, they want disagreement and all that, but they don't mean it. They want to hear themselves speak. They want to hear how great they are. There are so many egotistical people in those positions of power who just want to be propped up.

Maureen I've been hired expressly because of my experience and how I had achieved something in the past, hired by people who haven't done those things. They're like, "We need you to come in and do this because we don't know how to do it." Well, then you come in and you do it and you're like, "We need to change this direction." And they don't like hearing that, man. They do not like having that push back, even if that's literally what they hired you for. And so I found myself pushed out of rooms, kept from meetings. And it's because I was willing to go against the grain.

Maureen When you start something like that — you're going to have a shadow audience. You're going to have people who are rallying behind you who will never ever engage with you. They won't throw you a like. They won't send you a message. They'll do nothing, but you're still making a difference. And so I wish I'd known that in the beginning because I was like, "Dude, is this thing on? Can anyone see me? Like, does anyone give a shit?" You have to power through that in order to get to the other side.

13:04 Can Employees Be Friends?

Sergey I have very small experience in the corporate world. Everything you're saying is like a foreign language for me. I try to be a leader who invites criticism from my people — if I underpay them, I say don't hesitate to ask more. I just feel like people are your friends. And who says that your employees cannot be your friends, right, Maureen?

Maureen I mean, I'm with you there. That is also a slippery slope though. I've seen that too — it's super weird when you're friends with someone and then suddenly you're their boss. But at least for you the situation is already kind of baked into your employment arrangement with people. But yeah, I believe it should be possible. It should be possible to do the right thing and also do well.

14:05 Values in Life and Work

Sergey We're podcasters, and one of the fastest growing podcasts right now is Diary of a CEO. I remember how Steven Bartlett was talking to Simon Sinek — who I adore, he's my dream to have him on my show. Simon identified one of Steven's main values: always looking for truth. Speaking of your values, something that makes you you, Maureen — what are the things that help you navigate through challenges of life and profession and get on top?

Maureen I would say developing the sort of self-confidence that I will figure it out no matter what comes my way. And that comes with time, right? Like I've failed so many times in my life, it's a joke. And I know that whatever comes, I'm going to figure it out. And so that might mean a complete pivot. That might mean quitting. But I'll always figure it out.

Maureen And so when I did this, I knew there was a distinct possibility that I might never get another corporate job again, or I might get a corporate job because I did this, or I won't need a corporate job. Right? Like this is creator economy stuff. And there will be so many companies that are born to serve the creator economy. And you know what's going to be inherently valuable to those companies? Experience as a creator — because we're going to know exactly who they want to serve or we're going to know the ecosystem.

Maureen I also just couldn't live with the regret of not knowing what could have been. And that was the main number one reason I did it anyway.

Maureen Hilariously and unfairly — if you're the person who speaks up and says the system is broken and you build a platform on such a statement, you're almost more protected against the thing you're railing against than the average person who'd go on the internet and be like, "I was experiencing ageism and I'm a random candidate still looking for corporate jobs." That's dangerous for them to say. Whereas for me, a company could be like, "Hey, we're going to hire that person and we're going to look like we care." So it's a weird perverse way this works.

Maureen He said something that I'll never forget: "Everyone's cringe until they've made it, and then everybody's going to be like, 'That person's a genius.'" And I was like, "Yes, he's right." He's 29 years old and he's never wrong. But he's so smart. I credit any version of success that I've had so far a lot to him, really.

22:34 International Men's Day

Sergey Today this podcast is going to drop on International Women's Day. It's really big in my country. Is it big in the United States?

Maureen I mean yeah. I'm sure a lot of people working in corporate environments everywhere will see some dumb public post from their CEO or something that says that we appreciate women. Meanwhile, they've been 67% more likely to lose their jobs in layoffs and are more likely to have their jobs automated by AI and all that stuff. So it's a lot of performative bullshit frankly. But yeah, women are amazing. We should be celebrated all day and every day.

Maureen And actually one day someone asked me, "Well, when's International Men's Day?" And I was like, "That's every other day, dude." Like, let us have this day.

Maureen And women — we need more female creators. We need more of us out there. It has seemed at least publicly to be a very bro-dominated space. And by the way, I love dudes. I work with the Chad and Cheese podcast. Chad Sowash has been basically a mentor to me. He brought me on the show as a guest co-host. The system is broken — it actually sucks for men too. So really let's all work together here and make the system better. We need men. We absolutely need men to be our allies or we're never getting anywhere.

24:15 Career Advice for Women in Their 30s

Sergey I have a lady — I'm going to call her girlfriend. She's turning 30 and she's going through this process of looking for a job. For women trying to find themselves in their 30s, or maybe if they decided they want to start fresh in their 40s — what would be your advice?

Maureen As a woman who has been both in my 30s and is now in my 40s and reinventing myself, I think I'm equipped to answer. The 30s were a really hard decade for me. I had children in my 30s. And especially as an elder millennial who was taught that I can go do anything and be anything and just shoot for the stars in terms of career — I was like, wait, what the hell? How do I balance this motherhood thing with this career thing? And no one really talks about the loss of identity and the confusion that you feel when you become a mother. It is a life-altering experience.

Maureen I had basically career FOMO when I was out on maternity leave. I was up all hours of the night with a baby and I'd see people posting on LinkedIn, or I'd look at my work email — what's happening without me? And I was like, man, I've been working so hard for this stuff and suddenly I'm not there. I'm not going on the business trips. I'm not leading the initiative. You knew what you were doing in the corporate world, and suddenly you don't know what you're doing in the world of parenthood. And it feels so bad.

Maureen As I approached my 40s, I got a little bit better at it. I was better able to balance. I found organizations that gave me more flexibility. And now in my 40s, I'm completely pivoting away from what I did in the corporate world. So I would say to her and to any other woman considering doing this — it's going to be really challenging. And when you pivot, it strikes at the heart of a lot of people who've known you your whole life. You had to have such a core belief in yourself and do it anyway through all of the doubts. Very few people were wholeheartedly supportive in a way that was honest. And that was the hardest part for me.

29:24 Your Circle During Transformation

Sergey What happens with the people around you as you go through this transformation?

Maureen Oh man, they're embarrassed. They're embarrassed by what you're doing. And the good news is I'm old enough to know that that's not a reflection of how they feel about me really. It's about what they feel about themselves. It asks them — am I doing the right thing? Have I made the right decisions? And it's much more their discomfort with their choices than their feelings about you. And they're also thinking this way because they love you. They want you to do well. They want you to be okay. And when you do something that's perceived as risky, they're worried.

Maureen And the very public nature of what you're doing is just uncomfortable. It's uncomfortable for everybody. So the thing that I love now is meeting people I've never met before, going into new communities I've never been in, and being like, "Hey, I do XYZ. This is what I do. This is who I am now." Versus having to go on LinkedIn to all of my connections from my entire career — to all of literally everyone who knows me — and being like, this is the new version of me. This is what I'm doing now. That tension is tough. It's tough.

30:42 Building a Distinct Personal Brand

Sergey This is such a great lesson for all of us if we're building our personal brand. It should be distinct, right? It should be something that makes people think different things. You shouldn't be worried if they take it the wrong way and you should put yourself out there — online, offline.

Maureen Easier said than done. Very much easier said than done. I think it's a combination now — for all of us creators, we cannot over-rely on one thing. We think of our stock portfolios and we diversify, but we don't do that for our careers. We've been banking on putting it all on that employer paycheck and it's no longer looking like the good play.

Maureen The world of work is changing. Corporate — they're like oh, how can we extract more shareholder value from everybody? Let's make people get paid a lot less, let's give them less security, let's make them all fight for their rates and put them in the market. And it's going to push it all to the bottom and then they're going to continue to win. It sucks. It totally sucks. But that's the direction that things are going. So people really do need to start thinking about that future.

Maureen And one other thing I want to call out here — we need to all become salespeople. And that sucks for so many people because it's uncomfortable or it's not their skill set. But we're entering a world where you have to market yourself. You need to go online. You need to put yourself out there. There's actually a huge gap in the market for someone to come in and teach ex-corporate people how to sell themselves.

34:32 Mo's Message to the World

Sergey Let's finish up on a strong positive note. What keeps you going, Maureen? And maybe something you want to say as a final message to our international audience?

Maureen We all have incredibly important experience across all age groups. And we just need to be given the chance to just go do that. So I just don't want people to feel hemmed in or like they're done for, because we're not done yet. We're in our prime. No one's going to tell me when I can do something. Screw that. So go do the thing. You should care much more about what you think about you than what other people think about you.

Sergey Amen. Amen. Thank you, Maureen. That was amazing.