I Paid $48K for Health Insurance and Still Owed $10K—So I Built a Solution

Tech isn’t just in a downturn. It’s in the midst of a full-blown identity crisis. As layoffs, ageism, and AI reshape the workforce overnight, Brian Pulliam joins me to break down what’s actually happening behind the scenes… and what mid-career professionals must do to stay competitive.Brian, a former tech leader who spent 23 years at companies like Microsoft, Zillow, and Coinbase, joins me to talk about a controversial topic. With tech experiencing year-after-year meltdowns, Brian offers a brutally honest look at whether anyone should still pursue a tech career in 2025–2026.He breaks down why the job market feels broken, why entry-level roles are disappearing, and how AI is replacing the very apprentice-level opportunities that used to grow workers into senior talent. He also explains why employers are pulling back on long-term investment, what the real supply-and-demand curve looks like, and why ageism is hitting harder and earlier than ever.We discuss strategies for standing out in an oversaturated market, how to approach salary discussions, and the mindset shifts every experienced employee needs to remain competitive in a chaotic and unpredictable hiring landscape.If you're feeling overwhelmed by tech layoffs, frustrated by age bias, or unsure how to pivot in today’s wild job market, this episode gives you clarity, direction, and a whole lot of real talk.Do you want Brian to help you navigate the tech job market or level up your career? Mention you heard him on It Gets Late Early and get 20% off any coaching package when you book through his site or connect via LinkedIn.In This Episode:-Should anyone go into tech in 2025–2026?-Brian's early work experience and tech background-Standing out in a saturated market-How oversupply affects both young and older workers-Navigating the salary question-Should you apply to a big company or a small one?-How Brian coaches people over 40And much more!Resources:-Get Business Protection and Health Coverage at Solopreneur-friendly Prices - https://essentlcreator.com/maureen-Free Guide to LinkedIn Job Hunting for the 40+ Crew -https://www.itgetslateearly.com/job-guideConnect with Brian Pulliam:-LinkedIn: https://www.linkedin.com/in/briankpulliam/-Website: https://refactorcoaching.com/Connect with Maureen Clough:-LinkedIn: maureenwclough - https://www.linkedin.com/in/maureenwclough/-Website: itgetslateearly.com - https://www.itgetslateearly.com/-Instagram: @itgetslateearly - <a href="https://www.instagram.com/maureenwclough/" rel="noopener noreferrer"...

With mass layoffs hitting tech, media, and corporate America, more professionals over 40 are being forced into freelance work, consulting, and solopreneur life—whether they planned for it or not. And here's a big problem with that: the moment you leave corporate, you lose access to affordable health insurance. Suddenly, you're staring down $4,000/month premiums, sky-high deductibles, and hospital bills that make you wonder what you're even paying for.In today's episode, I sit down with Crystal Jackson—also known as The Real Mrs. Poindexter—a former Intel engineer turned viral content creator with millions of followers. After 13 years in corporate, Crystal left to raise her kids, went back to work for the benefits, left again, and eventually found herself paying $48,000 a year for health insurance that barely covered anything. When she got sick and ended up with another $10,000 in medical bills, she'd had enough.So she did what any fed-up engineer would do: she co-founded EssentL Creator with her husband Chris to solve the problem no one else would touch—affordable, corporate-level health insurance for freelancers, gig workers, and solopreneurs.In this episode, we talk about:Why Crystal was paying $48K/year for health insurance and still owed $10K in hospital billsHow the "future of work" is creating a wave of involuntary entrepreneurs (and what that means for you)What a PEO (Professional Employer Organization) actually is—and how it gives solopreneurs access to corporate-level benefitsWhy leaving corporate might be the scariest—and best—thing that ever happens to youHow to protect yourself legally and financially when you go out on your own (LLCs, IP protection, contract red-lining)The mental health crisis among content creators—and why EssentL offers enhanced mental health and addiction coverageIf you've been laid off, are thinking about going solo, or are tired of paying insane premiums for garbage coverage, this episode is for you. Find a gift of 50% off the admin fee for It Gets Late Early listeners at https://essentlcreator.com/maureen.Resources:-Get Business Protection and Health Coverage at Solopreneur-friendly Prices - https://essentlcreator.com/maureen-Free Guide to LinkedIn Job Hunting for the 40+ Crew - https://www.itgetslateearly.com/job-guideConnect with Crystal Jackson:-LinkedIn: https://www.linkedin.com/in/crystal-jackson-mba-8893b72bb/-Website: https://essentlcreator.com/Connect with Maureen Clough:-LinkedIn: maureenwclough - https://www.linkedin.com/in/maureenwclough/-Website: itgetslateearly.com - https://www.itgetslateearly.com/-Instagram: @itgetslateearly - <a href="https://www.instagram.com/maureenwclough/" rel="noopener...

Ever wondered why AI thinks you need to look younger? In this episode, Gretchen Andrew, a former Google employee turned artist, exposes the disturbing truth about how beauty filters are literally reshaping our faces—and our self-worth.We kick things off with Gretchen's bold pivot from Silicon Valley to the art world, where she's using robots, oil paint, and yes, glitter to reveal what beauty filters actually do to us. Her groundbreaking "FaceTune Portraits" physically apply AI beauty standards to paintings, creating violent scars and marks that show the hidden damage these "harmless" filters inflict on our identities.Gretchen breaks down the dirty secret of AI training data—how algorithms learn beauty from the most biased corners of the internet and create a feedback loop that makes everyone chase the same impossible standard. Even Miss Universe contestants aren't "good enough" for AI filters, and men in their 50s are rescheduling meetings just to use Zoom's "touch up my appearance" feature!From Hollywood actresses getting the same face-altering procedures to look good on small screens, to the shocking reality that social media may have incentivized us to provide facial recognition data for free, this conversation will change how you see every filter, every app, and every "enhanced" photo you encounter.Whether you're tired of the algorithmic beauty trap or just want to understand why everyone's starting to look the same, this episode is essential listening. Gretchen's insights will make you question everything about digital beauty—and maybe even inspire you to embrace what makes you uniquely human.“The question is: Do you want to look old and like yourself, or do you want to look like everybody else and look younger?”&nbsp;~ Gretchen AndrewIn This Episode:-Leaving Silicon Valley for art-AI vs. beauty standards-The homogenization of beauty-Gretchen's partnership with Andreessen Horowitz-The real story behind AI beauty filters-Ageism in the art and tech world-How Gretchen uses social media for her workAnd much more!Resources:-Free Guide to LinkedIn Job Hunting for the 40+ Crew - https://www.itgetslateearly.com/job-guideConnect with Gretchen Andrew:-Website: https://www.gretchenandrew.com/-LinkedIn: https://www.linkedin.com/in/gretchen-andrew/-Instagram: https://www.instagram.com/gretchenandrew/Connect with Maureen Clough:-LinkedIn: maureenwclough - https://www.linkedin.com/in/maureenwclough/-Website: itgetslateearly.com - https://www.itgetslateearly.com/-Instagram: @itgetslateearly - https://www.instagram.com/itgetslateearly/-YouTube: <a...

What if everything you thought you knew about startup success was wrong? In today’s episode of It Gets Late Early, I’m breaking down the myth that young, hoodie-wearing entrepreneurs are the key to successful startups. Spoiler: the data proves otherwise.&nbsp;According to MIT research, the average age of a high-growth startup founder is 42 — not 21. The top 1% of founders are even older, typically around 45 years old. Yet, venture capitalists continue to invest in young, inexperienced founders, ignoring the seasoned leaders with decades of experience.I also tackle the growing age discrimination in tech, where older workers are pushed out despite having the experience and connections that drive success. Companies that embrace diverse ages and experiences in their teams are the ones that succeed.&nbsp;Let’s flip the script on startup success. It's time to stop assuming that youth equals innovation. It’s never too late to go after your dreams, and age is an asset, not a liability.“So just why is it that older workers tend to be more successful? Two words: life experience.”&nbsp;~ Maureen Wiley CloughIn This Episode:-Research from MIT: the truth about successful startup founders-The age bias in venture capital and tech hiring-Why older founders have an advantage over younger ones-The challenge to venture capitalists: stop funding failure-Encouraging older tech workers: your experience mattersAnd much more!Resources:-Free Guide to LinkedIn Job Hunting for the 40+ Crew - https://www.itgetslateearly.com/job-guide-EEOC Special Report - https://www.eeoc.gov/special-report/high-tech-low-inclusion-diversity-high-tech-workforce-and-sector-2014-2022-MIT Research on Age and High-Growth Entrepreneurship - https://mitsloan.mit.edu/shared/ods/documents?PublicationDocumentID=6212#:~:text=Our%20primary%20finding%20is%20that,growth%20new%20ventures%20is%2045.0.-Ageism in Tech Hiring - https://www.linkedin.com/posts/maureenwclough_tech-ageism-hiring-activity-7369769952683171841-u7zS?utm_source=social_share_send&amp;utm_medium=member_desktop_web&amp;rcm=ACoAAACPAV4BMEaPyyLI0T1Hayp_eLtXH5AO5-4-iPhone unveiling with Steve Jobs - https://www.youtube.com/watch?v=x7qPAY9JqE4-Workplace Age Discrimination Cases Grow Nationwide - https://gbsbenefitsgroup.com/workplace-age-discrimination-cases-grow-nationwide/#:~:text=The%20Equal%20Employment%20Opportunity%20Commission%20(EEOC)%20has,Act%20(ADEA)%20as%20in%20fiscal%20year%202022-Late-Career Job Losses Are Blurring What Retirement Looks Like in America - <a...

Meetings. Ugh. We’ve all been there, right? And the price tag is bigger than most people realize. We estimate that the cost to organizations of these unproductive meetings is approximately $259 billion in the United States and $64 billion in the United Kingdom for professional staff alone (LSE report). That’s a jaw-dropping drain on productivity—yet it’s largely preventable.In today’s episode of It Gets Late Early, I’m joined by Dr. Daniel Jolles, a behavioral scientist and psychologist at the London School of Economics, who’s back for his second appearance. Dr. Jolles and I go deep into the world of generational diversity in meetings, exploring how getting it right can significantly boost productivity and reduce wasted hours.We’re also tackling the elephant in the room: AI in the workplace. With organizations now mandating the use of AI, how can we, across all generations, navigate this technology without falling victim to bias or further exclusion?We cover the shocking stats about how unproductive meetings cost businesses billions each year and how companies can make sure that no one, especially older workers, gets left behind in the AI race.Trust me, this episode is a wake-up call. If you’re looking to fix your meetings, ensure inclusivity, and stay ahead in the AI-driven future, you don’t want to miss it.“We find that there's a huge lack of generational diversity happening in our meetings. Our research suggests that that's hurting productivity because there are diversity benefits to be gained by having voices from the younger and older employees present in meetings, especially when it comes to big-decision meetings.”&nbsp;~ Dr. Daniel JollesIn This Episode:-Why employees are not that fond of meetings-The impact of generational diversity on meetings-The cost of unproductive meetings-AI’s potential to revolutionize the workplace-The impact of the proliferation of AI recording toolsAnd much more!Resources:-Free Guide to LinkedIn Job Hunting for the 40+ Crew - https://www.itgetslateearly.com/job-guide-LSE Report: When Generations Meet by Dr. Daniel Jolles and Dr. Grace Lordan - https://www.lse.ac.uk/tii/assets/documents/When-Generations-Meet.pdfConnect with Dr. Daniel Jolles:-LinkedIn: https://www.linkedin.com/in/danieljolles/-Website: https://www.danieljolles.com/Connect with Maureen Clough:-LinkedIn: maureenwclough - https://www.linkedin.com/in/maureenwclough/-Website: itgetslateearly.com - https://www.itgetslateearly.com/-Instagram: @itgetslateearly - <a href="https://www.instagram.com/maureenwclough/"...

Ever applied, interviewed, and…silence? You’re not alone. In this episode, we crack open the hiring black box: the rise of ghost jobs (roles that never close or never existed in the first place), the avalanche of AI-boosted applications, and why 31% of rejected candidates never even get an email.&nbsp;My guest Ariana Moon, VP of Talent Planning &amp; Acquisition at Greenhouse, a software platform managing the hiring process, explains how their Greenhouse Verified badges reward employers who actually walk the talk—communication, fairness, respect, and preparation—so candidates can spot companies that treat people like people.We also get real about what great hiring actually looks like: structured scorecards, clear rubrics, and leaders who blend experience with fresh perspectives. Ariana shares lessons from a very millennial workforce moment (when ~10% of the company went on parental leave at once!) and how Greenhouse supports parents with thoughtful leave, re-entry, and caregiver communities—without letting careers evaporate.Whether you’re job hunting or leading a team, this episode is a playbook for a fair, respectful, and effective process—because employer brand is a long game, and candidates remember how you made them feel.Update: Since this recording, Ariana has given birth to a healthy baby boy! Both mom and baby are doing great.“Greenhouse Verified is a way that we can signal to the talent market that we are a company that prioritizes things like good communication, being prepared in how we run our interview processes, being fair in how we think about our interview processes, and being respectful when we're interacting with candidates. ”&nbsp;~ Ariana S. MoonIn This Episode:-What are ghost jobs?-Greenhouse Verified initiative-Improving internal processes in the workplace-Experiences with ageism in the workplace-ERGs and supporting parents in the workplaceAnd much more!Resources:-Free Guide to LinkedIn Job Hunting for the 40+ Crew - https://www.itgetslateearly.com/job-guideConnect with Ariana S. Moon:-LinkedIn: https://www.linkedin.com/in/ariana-s-moon/-Website: https://www.greenhouse.com/Connect with Maureen Clough:-LinkedIn: maureenwclough - https://www.linkedin.com/in/maureenwclough/-Website: itgetslateearly.com - https://www.itgetslateearly.com/-Instagram: @itgetslateearly - https://www.instagram.com/itgetslateearly/-YouTube: @itgetslateearly - <a href="https://www.youtube.com/channel/UCGrHwk-y7ERaq7bCSjZYf1A?sub_confirmation=1" rel="noopener noreferrer"...

Marketers love chasing Gen Z. But here’s the trillions-of-dollars blind spot:Gen X and Boomers control nearly 70% of U.S. disposable income and outspend younger generations in nearly every major category — alcohol, beauty, travel, finance, and more.So why are brands still ignoring them?In this episode, I sit down with Brent Rivard, founder and CEO of Geezer Creative, an agency built on a radical idea: the “forgotten generation” isn’t just relevant — they’re the growth engine brands are missing.We unpack how the ad industry’s obsession with youth culture has aged itself out of opportunity, what’s at stake for marketers, and how Gen X and Boomers are reshaping the creative economy.You’ll also hear shocking stats about how the industry treats its veterans, the challenges older professionals face in a rapidly evolving gig economy, and why AI is becoming a make-or-break skill for creative professionals of every generation.Because if brands keep underestimating us, that’s on them. But if we underestimate ourselves? That’s on us.The creative economy is shifting fast — from AI to the rise of the gig economy — and this conversation will give you a fresh (and dare I say slightly rebellious?) perspective on where your experience fits next.“The last thing the world needed was another ad agency, so we opened one. But we didn't just open one–we opened one that has a point of view.”&nbsp;~ Brent RivardIn This Episode:-Ageism in the advertising industry-Why Gen X consumers are crucial for marketing success-Geezer Creative’s approach to Gen X-centered marketing-The advantage of intergenerational marketing teams-Adapting to the gig economy in the creative space-Shifting client priorities and how agencies can adapt-AI and its impact on the creative industry-Encouraging older professionals to embrace new opportunities-Creative solutions for dealing with layoffs and market shiftsAnd much more!Resources:-Free Guide to LinkedIn Job Hunting for the 40+ Crew - https://www.itgetslateearly.com/job-guide-The Gen X Career Meltdown - https://www.nytimes.com/interactive/2025/03/28/style/gen-x-creative-work.htmlConnect with Brent Rivard and Geezer Creative:-Brent Rivard LinkedIn: https://www.linkedin.com/in/brent-rivard-7ba8b37/-Geezer Creative LinkedIn - https://www.linkedin.com/company/geezer-creative/-Website: https://www.geezercreative.com/Connect with Maureen Clough:-LinkedIn: maureenwclough - https://www.linkedin.com/in/maureenwclough/-Website: itgetslateearly.com - https://www.itgetslateearly.com/-Instagram: <a href="https://www.instagram.com/maureenwclough/" rel="noopener noreferrer"...

Why is it terrifying to present to just four people? According to Will Greenblatt, it's because our brains still think the tribe might "club us over the head" if they don't like what we say.Will's journey from Canadian child actor (yes, a self-proclaimed "nepo baby") to sought-after corporate speaking coach is anything but typical. After working with Anne Bancroft as a kid and nearly getting swept up in the Hollywood machine, a family tragedy and toxic theater school experience led him to completely reinvent himself.But here's what makes this episode essential listening: Will discovered that the same skills that make great actors also create breakthrough leaders. The difference? It's not about performing—it's about finding emotional truth and connecting authentically with your audience.The game-changing insight: When Will's clients embrace just 10% more vulnerability in meetings, they see measurable career improvements—better performance reviews, more influence, and stronger professional relationships. Because while everyone else is playing it safe, that small dose of authenticity makes you unforgettable.We dive deep into why mentorship is broken in today's workplace, how to spot genuine people in interviews, and Will's three-act framework for storytelling that builds instant trust. Plus, he shares the uncomfortable truth about why taking career risks, like leaving acting or corporate, might be the safest move you can make.“You give somebody the opportunity to destroy you, and you hope that they won't, and they might. But you can't love without that risk. And it's the same kind of thing when you tell your boss what you really think.”&nbsp;~ Will GreenblattIn This Episode:-The real difference between performing and authentic communication-Why our fear of public speaking is literally prehistoric&nbsp;-The 10% vulnerability rule that transforms careers&nbsp;-How to build trust through authentic storytelling&nbsp;-Will's childhood-to-adult-choice framework for connection&nbsp;-Why the "speaker-writer-coach-creator" career is the future&nbsp;-How to network without being transactional&nbsp;And much more!Resources:-Free Guide to LinkedIn Job Hunting for the 40+ Crew - https://www.itgetslateearly.com/job-guide-Supercharge Your Speaking Skills by Will Greenblatt - https://www.youtube.com/playlist?list=PL2esQpzqZUUYD8Nxp9lKe05K1aYMpsNwUConnect with Will Greenblatt:-LinkedIn: https://www.linkedin.com/in/willgreenblatt/-Website: https://www.skool.com/speakingheroes/aboutConnect with Maureen Clough:-LinkedIn: maureenwclough - https://www.linkedin.com/in/maureenwclough/-Website: itgetslateearly.com - https://www.itgetslateearly.com/-Instagram: <a href="https://www.instagram.com/maureenwclough/" rel="noopener noreferrer"...

Losing a job is never easy, but what if it led to a more fulfilling path? Daniel Incandela, former CMO, opens up about the painful yet transformative experience of being fired in his 50s. In this episode, he shares the emotional toll it took, how he navigated the challenges, and the powerful lessons he learned along the way. Today, I sit down with my good friend, Daniel Incandela, who, like many of us, faced the harsh reality of burnout and being let go. His story is one of resilience and transformation. Despite the painful blow of being fired, Daniel reflects on how the experience helped him realign his priorities, focusing on family, health, and ultimately finding his path forward through consulting and creative work.We discuss the importance of reflection and accountability, even in the most challenging moments. Daniel’s journey sheds light on how career paths don’t always go as planned, and how the pressure to “do it all” can weigh heavily on us. From navigating ageism in a competitive job market to embracing AI as a necessary tool for today’s workforce, Daniel discusses how he’s finding purpose in his new role and working towards a future that aligns more with his values.If you’ve ever felt like your career took an unexpected turn, this episode is for you. Daniel’s story is a powerful reminder that we can find clarity even in moments of doubt.“I've been on this journey that I think I really needed in life, and it has helped me awaken from things I did not see.”&nbsp;~ Daniel IncandelaIn This Episode:-Daniel’s transition from CMO to consultant-Embracing change and realizing what really matters-Leadership in the time of AI-The reality of getting fired in your 50s-Experiencing the immense benefits of slowing down-Looking ahead: the future of work in a gig economy-Why learning how to use AI is no longer optionalAnd much more!Resources:-Free Guide to LinkedIn Job Hunting for the 40+ Crew - https://www.itgetslateearly.com/job-guide-The Gen X Career Meltdown - https://www.nytimes.com/interactive/2025/03/28/style/gen-x-creative-work.htmlConnect with Daniel Incandela:-LinkedIn: https://www.linkedin.com/in/danielincandela/-Substack:https://substack.com/@danielincandela-Newsletter by Daniel Incandela - https://danielincandela.substack.com/Connect with Maureen Clough:-LinkedIn: maureenwclough - https://www.linkedin.com/in/maureenwclough/-Website: itgetslateearly.com - https://www.itgetslateearly.com/-Instagram: @itgetslateearly - <a href="https://www.instagram.com/maureenwclough/" rel="noopener noreferrer"...

Let’s face it, whether you're looking for a new job, trying to stand out in your current role, or considering a career pivot, building a personality brand is a real game-changer (you read that right. A personality brand, not a personal one). In today’s landscape, you need more than just experience; you need a personality that resonates. In this episode, Danielle Hughes, Chief Personality Officer at More Than Words Marketing, joins me to chat about why creating a personality brand isn’t just about ‘selling’ yourself.Danielle shares tips on how to confidently showcase your authentic self in your professional persona, particularly on platforms like LinkedIn. She emphasizes the importance of not just telling your story but showing it through real examples and personal achievements.&nbsp;Whether you're pivoting careers or leveling up in your current role, branding is more important than ever. Tune in to hear how you can use your personality to stand out in the competitive job market and connect authentically with others.And just in case you're interested in working from beautiful homes all over the world, Danielle shares how she makes it happen.“Why is it a personality brand and not personal? Personal means private, so I never understand why we tell people to have a personal brand. Personality is who we are, and that's how we foster connection...with other people.”&nbsp;~ Danielle HughesIn This Episode:-Danielle's elevator pitch&nbsp;-Why personality branding is crucial in today’s world-How to connect your career story with your brand-Developing your personality brand on LinkedIn-Advice for people contemplating a career shift or facing layoffs-The need for an optimized LinkedIn profile-How to differentiate yourself in an oversaturated job market-An interesting story about Danielle-Danielle's approach to helping clients craft their personality brand-Final thoughts on using personality branding to stand outAnd much more!Resources:-Free Guide to LinkedIn Job Hunting for the 40+ Crew - https://www.itgetslateearly.com/job-guide-Swap Homes and Unlock the World - https://www.homeexchange.com/Connect with Danielle Hughes:-LinkedIn: https://www.linkedin.com/in/daniellehughes/-Website: https://www.morethanwordscopy.com/Connect with Maureen Clough:-LinkedIn: maureenwclough - https://www.linkedin.com/in/maureenwclough/-Website: itgetslateearly.com - https://www.itgetslateearly.com/-Instagram: @itgetslateearly - https://www.instagram.com/itgetslateearly/-YouTube: <a href="https://www.youtube.com/channel/UCGrHwk-y7ERaq7bCSjZYf1A?sub_confirmation=1" rel="noopener noreferrer"...