Managing Through The Millennial Career Crisis

If you’re disillusioned with your current job, you’re far from alone. Turns out, a whole generation is looking for a better road to career “success.” In the face of all this well-deserved disillusionment, I sought out the person behind the trending “millennial career crisis” hashtag to really get to the bottom of what the phenomenon is and why it seems to be affecting my generation especially.  Janel Abrahami is a career coach whose background in organizational psychology and corporate HR, and her own career crisis, make her the ideal advisor and spokesperson for forging a better path. Janel argues that, thanks to a heap of daunting factors, a “successful career” looks a lot different than it did in our parents’ day. She joins me to break down her six pathways that help us take back ownership of our careers in the face of despair and disillusionment Retake control and design your own success: Six pathways that let you choose your own adventure; Why career dissatisfaction seems to be hitting millennials hard right now; The importance of resting before we jump and strategizing before we build; The broken social construct facing everyone working today. Related Links: Connect with Janel on LinkedIn - https://www.linkedin.com/in/janelabrahami/ Learn more about Janel - https://janelabrahami.com/ Follow Janel on Instagram - https://www.instagram.com/janelabrahami/ Subscribe to the weekly newsletter, “Going Places” - https://janelabrahami.beehiiv.com/ Episode 535, “The Women’s Ambition ‘Gap’ is a Myth” - https://www.bossedup.org/podcast/episode535 Episode 538, “Rebalance Your Career Portfolio” - https://www.bossedup.org/podcast/episode538 Episode 528, “Start Planning Your First Mini-Retirement” - https://www.bossedup.org/podcast/episode528 LinkedIn Learning Course, “Get Unstuck: Make a Plan to Move Your Career Forward” - https://www.linkedin.com/learning/get-unstuck-make-a-plan-to-move-your-career-forward HIRED: A Job Search Accelerator to Land Your Dream Job - https://www.bossedup.org/gethired “The Art of Gathering” by Priya Parker - https://bookshop.org/p/books/the-art-of-gathering-how-we-meet-and-why-it-matters-priya-parker/6cf339d7407925e3 Jim Carey’s story about his father’s career choice - https://youtu.be/FSY-hDlx5yk?si=0PupcGJzx2LCNBLu&t=19 Bossed Up Courage Community - https://www.facebook.com/groups/927776673968737/ Bossed Up LinkedIn Group - https://www.linkedin.com/groups/7071888/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

How could you diversify your income streams by pursuing your interests? Anyone who knows me knows I have a lot going on—I run Bossed Up, I have a corporate day job, I’m a parent…and that’s not even half of it. But I firmly believe that expanding your career portfolio is a wise move, for your finances and your energy sustainability.  Especially in the current wildly unstable job market, why focus all your time, energy, and interest on a single job? By doing so, you run the risk of being left at loose ends if, heaven forbid, your job falls through. In this episode, I share my own exciting new business venture, along with some helpful tips for exploring your own side hustles and hobby monetization. If you’ve ever considered becoming a multi-hyphinate—or know someone who’s on that path—you’re going to love this one. Mitigate your income risk and diversify your time and energy: The two pie charts that sum up your career portfolio; How to find more time for your side hustle without exhausting yourself; Three ways you can start to explore doing more, safely and strategically. Related Links: Matt Schumer’s essay “Something Big is Happening” - https://x.com/mattshumer_/status/2021256989876109403 Episode 536, Strategic Detachment: A Trend for Surviving and Thriving - https://www.bossedup.org/podcast/episode536 “The Lean Startup” by Eric Reis - https://bookshop.org/p/books/the-lean-startup-how-today-s-entrepreneurs-use-continuous-innovation-to-create-radically-successful-businesses-eric-ries/3cb6bdcf8f1bebc2 My NEW LinkedIn Learning Course: Get Unstuck: Make a Plan to Move Your Career Forward - https://www.linkedin.com/learning/get-unstuck-make-a-plan-to-move-your-career-forward-30720060 Bossed Up Courage Community - https://www.facebook.com/groups/927776673968737/ Bossed Up LinkedIn Group - https://www.linkedin.com/groups/7071888/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

What are the leadership qualities that inspire people to follow you? There is no shortage today of people in power leading through force and intimidation. This frightening reality should serve to remind us how essential it is that the people we choose to follow lead with empathy and compassion, not coercion.  Tamra Ryan is a nationally recognized speaker, author, and leadership expert who redefines what it means to lead with purpose and care. In this episode, she and I discuss how leaders can inspire a following through courage and conviction, as well as compassion. Tamra has a long history of empowering others to lead, and her perspectives and recommendations for what that requires are what we need to keep pushing for a better world, right now. Build your own “followship” with the virtues that really make an impact: Why it’s just as important to give grace as it is to speak your mind; The four elements of leadership that capture hearts and minds; And how to stick to your convictions as a leader, even in today’s delicate climate. Related Links: Learn more about Tamra - https://www.tamraryan.com/about Connect with Tamra on LinkedIn - https://www.linkedin.com/in/tamraryan/ Learn more about Women’s Bean Project - https://www.womensbeanproject.com/ Learn more about the Common Sense Institute - https://www.commonsenseinstituteus.org/colorado/about/fellows/tamra---ryan Episode 352, “Self-Advocacy Hacks for a Toxic Workplace” - https://www.bossedup.org/podcast/episode532 Episode 536, “Strategic Detachment: A Trend for Surviving and Thriving” - https://www.bossedup.org/podcast/episode536 Episode 525, “Resisting Despair: Coping Tools For A Declining Democracy” - https://www.bossedup.org/podcast/episode525 SPEAK UP: A Live Assertive Communication Course -  https://www.bossedup.org/speakup Bossed Up Courage Community - https://www.facebook.com/groups/927776673968737/ Bossed Up LinkedIn Group - https://www.linkedin.com/groups/7071888/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

What would change if you stopped agreeing to take on everything at work? If you have perfectionist and overachiever tendencies like I do, it’s possible this question has never even occurred to you. In the race to the top, it can feel like everything is urgent and our responsibility. But there’s a better way. A new trend floating around social media recently caught my attention, and it’s called “strategic detachment.” In this episode, I take a look at a more thoughtful approach to workload management and delegation, especially as it applies to team leaders. The professional landscape is transforming so rapidly in so many ways—this might just be the trend we need to survive 2026.Hop off the overachieving hamster wheel and onto your true career trajectory. Tune in to learn:The unintended consequences leaders create when they won’t step back;What strategic detachment really means (and what it doesn’t);Why you might need to examine your fear to avoid burning out.Related Links:Episode 403, How First-Time Managers Can Embrace Coaching - https://www.bossedup.org/podcast/episode403Episode 368, What Quiet Quitting Can Help…or Hurt - https://www.bossedup.org/podcast/episode368LEVEL UP: a Leadership Accelerator for Women on the Rise - https://www.bossedup.org/levelupBossed Up Courage Community - https://www.facebook.com/groups/927776673968737/Bossed Up LinkedIn Group - https://www.linkedin.com/groups/7071888/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

How often have you heard the rhetoric that if you want success badly enough, if you work hard enough, you’ll find success? As women, we grow up with a promise—from little girls who can “be whatever we want to be” to full-grown “girl bosses,” the world is our equal-opportunity oyster. But the data doesn’t prove this out. It’s that data Stefanie O’Connell breaks down and picks apart in her new book, The Ambition Penalty, and in our honest and research-backed conversation. As her book’s tagline says, “corporate culture tells women to step up―and then pushes them down.” Whether this feels all too real to you or you’re skeptical, Stefanie’s exploration of the metrics and the myths will get you thinking about how you challenge inequality in every environment where it still thrives.Stop blaming yourself and start challenging the status quo:Why prioritizing self-optimization can backfire;The systems we should be holding accountable for the ongoing inequality;The problem with the male victimhood narrative;What happens when we model healthy power and gender dynamics to our children?Related Links:Listen to Episode 408, Women and the Ambition Penalty - https://www.bossedup.org/podcast/episode408Connect with Stefanie on LinkedIn - https://www.linkedin.com/in/stefanieoconnell/Pre-order The Ambition Penalty - https://bookshop.org/p/books/the-ambition-penalty-how-corporate-culture-tells-women-to-step-up-and-then-pushes-them-down-stefanie-o-connell/bf6de978036a09ffSubscribe to Too Ambitious on Substack - https://tooambitious.substack.com/Follow Stefanie on Instagram - https://www.instagram.com/stefanieoconnell/TAKE ACTION with Bossed Up - https://www.bossedup.org/takeactionBossed Up Courage Community - https://www.facebook.com/groups/927776673968737/Bossed Up LinkedIn Group - https://www.linkedin.com/groups/7071888/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

When someone at work shares an opinion you don’t agree with, what’s your response? Do you move on with an agreeable nod, or do you push back? All too often, we take the former route. So many of us are taught not to rock the boat by expressing disagreement. But here’s my hot take: you can share your honest and dissenting opinion in a way that wins you major leadership points.In fact, I firmly believe that disagreeing shouldn’t be as rare as it is, especially from those in leadership positions. Disagreeing without being disagreeable changes how people perceive you and can open some promising doors for both your career and your team’s future. So let’s embrace these three steps to highlight your critical thinking skills and earn respect:Ask this key follow-up question that directs your dissent;Embrace an accessible hack for the hard part: sharing your hot takeAnd finally, the thoughtful structure that showcases your thought leadership.Related Links:SPEAK UP: A Live Assertive Communication Course for Women in the Workplace - https://www.bossedup.org/speakupBuy Bossed Up, the book - https://www.bossedup.org/bookBossed Up Courage Community - https://www.facebook.com/groups/927776673968737/Bossed Up LinkedIn Group - https://www.linkedin.com/groups/7071888/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

How do you rest and recharge when the world feels chaotic? After an unexpectedly hectic December, the Bossed Up podcast is back with a look at what recharging really requires—and it’s not quitting everything or carrying on as usual. I’ve come to realize that the sweet spot, at least for me, is somewhere in the middle. This episode breaks down the balance I’m seeking to find this year, and I’d love to hear how it compares to your approach to the New Year. Between seriously scary news cycles and never-ending schedules, it’s all too easy to overlook gratitude in lieu of existential dread and getting everything done. Consider this your invitation to take a beat, drop a ball (or two), and approach 2026 with a healthy dose of self-compassion.Join me in recalibrating for 2026 so we can recharge for real:How we can strike a balance between pushing forward and being present;The role gratitude plays in staying realistic about the future;When and where to decenter social media and lean into the analog;A reminder to give your personal calendar a bit of love.Related Links:TAKE ACTION - https://www.bossedup.org/takeactionGet a copy of The Husbands by Holly Gramazio - https://bookshop.org/p/books/the-husbands-a-read-with-jenna-pick-a-novel-holly-gramazio/658e8495219fe107EP 525 “Resisting Despair: Coping Tools for a Declining Democracy” - https://www.bossedup.org/podcast/episode525Try out the BePresent app - https://www.bepresentapp.com/Bossed Up job search resources - https://www.bossedup.org/free-resources/job-searchThe Definitive Guide to Negotiating as a Woman - https://www.bossedup.org/negotiationBossed Up Courage Community - https://www.facebook.com/groups/927776673968737/Bossed Up LinkedIn Group - https://www.linkedin.com/groups/7071888/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

How can you advocate for yourself when you’re operating in a broken system? We’re gearing up to face even more unprecedented times in 2026. And recent research shows, unsurprisingly, that inclusive and DEIB policies continue to be phased out while hostile work environments expand. Many of us are all too familiar with the lack of resources out there to help us cope with all this, especially options specific to Black women and Women of Color, who face the brunt of this ongoing shift.That’s the landscape that prompted Sarah Boyd to found The Formation, an app that serves up “real talk, real resources, and real tight-knit community” for Black women navigating the realities of corporate America. She joins me to break down her evidence-backed recommendations for how we should protect ourselves while we fight the bigger fight of fixing our broken systems.Start documenting everything and finding your career clarity as we cover:How corporate changes are impacting Black women and Women of Color;Why you need to keep your work receipts—all of them;How to frame your stretch work and find your ideal audience;The innate gap-filling gift so many women have, and how to maximize it.Related Links:Connect with Sarah on LinkedIn - https://www.linkedin.com/in/sarahwilliamsboyd/The Formation community - https://www.weareyourformation.com/The DISRUPT program - https://www.weareyourformation.com/our-programWomen in the Workplace 2025 - https://www.mckinsey.com/capabilities/people-and-organizational-performance/our-insights/women-in-the-workplaceLanguage Bias in Performance Feedback 2024, Textio - https://textio.com/feedback-bias-2024“Get Unstuck: Make a Plan to Move Your Career Forward”, LinkedIn - https://www.linkedin.com/learning/get-unstuck-make-a-plan-to-move-your-career-forwardBossed Up Courage Community - https://www.facebook.com/groups/927776673968737/Bossed Up LinkedIn Group - https://www.linkedin.com/groups/7071888/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

What can you do to help turn the widening gender pay gap around? For 20 years, American workers watched as the discrepancy between men’s and women’s incomes slowly lessened. Then, this October, a new report showed that the positive trend is reversing. Women in the U.S. are now making 76 cents for every dollar men make—a difference of around $14,000 a year. In this episode, I’m breaking down why we’re seeing this shift and what we can do about it. Do your part to close the gender wage gap:Learn 3 powerful ways you can make a positive difference in the fight for pay equality;Hear which 36 million households bear the brunt of this impact;And what the data has to say about this shift in momentum.Related Links:National Partnership for Women and Families, “America’s Women and the Wage Gap” - https://nationalpartnership.org/report/americas-women-and-the-wage-gap/Equal Employment Opportunity Commission, “Executive Order 11246” - https://www.eeoc.gov/history/executive-order-no-11246\Bossed Up, “The Definitive Guide to Negotiating as a Woman” - https://www.bossedup.org/negotiationLinkedIn Learning Course, “Negotiating Your Compensation Package” - https://www.linkedin.com/learning/negotiating-your-compensation-packageEpisode 462, “Understand Pay Transparency and Your Rights as a Job Seeker” - https://www.bossedup.org/podcast/episode462Episode 444, “Are Pay Transparency Laws Working?” - https://www.bossedup.org/podcast/episode444Episode 422, “What Actually Creates Gender Equality at Work?” - https://www.bossedup.org/podcast/episode422Episode 317, “Making Progress on Equal Pay Day” - https://www.bossedup.org/podcast/episode317Bossed Up Courage Community - https://www.facebook.com/groups/927776673968737/Bossed Up LinkedIn Group - https://www.linkedin.com/groups/7071888/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

As managers and employees, how can we ensure that we support equitable disability accommodations for everyone? The Americans with Disabilities Act (ADA) offers a wealth of protections, but many workers and leaders are unaware of what these protections entail. Luckily, there are experts like Rachel Shaw out there to shed light on their intricacies and help educate us all.Rachel is a leading strategist in workplace inclusion and disability compliance and the author of “The Disabled Workforce: What the ADA Never Anticipated.” She joins me to add clarity to the laws in place to protect people with disabilities—including mental health and pregnancy—and ensure we have access to an equitable work environment that allows us all to be productive contributors, whatever differences of ability we might experience in our lifetimes. Understand your rights and responsibilities around disability inclusion:The most proactive and effective way to ask for an accommodation;The essential accommodation process every organization needs to develop;How much it really costs companies to approve employee requests;What’s missing from the ADA and how it’s being addressed.Related Links:Connect with Rachel Shaw on LinkedIn - https://www.linkedin.com/in/rachel-shaw-00037745/Learn more about Rachel’s work - https://rachelshaw.com/Buy “The Disabled Workforce” - https://www.amazon.com/Disabled-Workforce-What-Never-Anticipated/dp/1544708599Episode 390, How to Manage ADHD in the Workplace - https://www.bossedup.org/podcast/episode390Episode 460, Balancing Work with a Complicated Pregnancy - https://www.bossedup.org/podcast/episode460Episode 123, Pursuing a Promotion While Pregnant - https://www.bossedup.org/podcast/episode123Episode 335, What do mom-friendly Workplaces look like and how to create them - https://www.bossedup.org/podcast/episode335   Episode 311, How to Talk About Marital Status, Parental Status, and Pregnancy in the Interview - https://www.bossedup.org/podcast/episode311Episode 315, How to Talk About Disability or Chronic Illness in the Job Interview - https://www.bossedup.org/podcast/episode315LEVEL UP: a Leadership Accelerator for Women on the Rise - https://www.bossedup.org/levelupBossed Up Courage Community - https://www.facebook.com/groups/927776673968737/Bossed Up LinkedIn Group - https://www.linkedin.com/groups/7071888/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.