On Second Thought with Jackie Pfeifer

Jackie Pfeifer

Welcome to On Second Thought with me, Jackie Pfeifer, a podcast for ambitious women and mothers who built a life doing everything "right," and are now questioning whether it's actually the life they want to keep living. Nothing has to be falling apart for you to question what comes next. You can be grateful for your life and still change your mind on the direction you want to take. Through honest conversations, new perspectives, and practical tools, this podcast will help you feel brave enough to question yourself, honest enough to get real clarity, and capable enough to explore new directions without blowing up everything you've built. Because sometimes creating the life you want starts with one honest realization: "On second thought, I want something different."

  1. 4d ago

    17: Money Fear vs. Money Facts: How Successful Women Get Clear on Their Finances with Michelle Jacobik

    Have you ever had your best year yet and still had no idea where the money went? You make good money. You worked really hard to get here. And yet there's this quiet feeling that you're one bad month away from panicking, and if you're honest, that feeling gets a vote in every big decision you're trying to make about what comes next. In this episode of On Second Thought, Michelle Jacobik and I talk about why so many successful women feel broke even when the numbers say otherwise, and why you can't make long-term decisions about your life while you're drowning in fear about money. We get into finding your real number (not just the bills with due dates), why mindset work can't cover up a money problem you're avoiding, what to know before you leave the stability of a paycheck to build something of your own, and how to choose the right mentor for the stage you're actually in. Michelle Jacobik is a bestselling author, national speaker, and financial strategist whose work has been featured on ABC, FOX, CBS, Thrive Global, and in Entrepreneur magazine. With over two decades in financial services, she grew her own property and casualty insurance business in Connecticut from $600,000 to $12 million in annual sales and from 1,100 customers to more than 7,000 before exiting to mentor others. She is the author of The Path to Profits and Prosperity After Divorce and the creator of The Path To Profits Framework™. What's Discussed: (19:23) Why you can make good money and still feel like you're one month away from panicking. (21:53) The question to ask yourself before you decide you're broke. (26:05) Why you can't make long-term decisions while you're drowning in money fear. (31:11) The difference between your bills and your real number, and why most of Michelle's clients are off by 70%. (42:33) Going back to work four days after her daughter was born 10 and a half weeks early, and the money story that was driving her. (51:15) Why her next business took three years and two pivots to come together, even with decades of experience behind her. (1:03:43) The biggest mistake people make when choosing a coach or mentor. If you've ever made more money than you thought you would and still lie awake wondering why it never feels like enough, this one is for you. Come sit at the table 🤍 The conversation does not end when the episode does. My Substack is where the rest lives: my raw, unedited thoughts on every episode, free, every week, plus the world I am building around style, beauty, travel, and the questions we are all actually asking. And when you are ready for the decisions, what I actually bought, booked, and believed, names and prices included, listeners get 20% off your first year prettybigthoughts.substack.com/777 Start free: prettybigthoughts.substack.com  See everything inside the community: PBT Sales Page   Learn more about Jac Pfeifer: Instagram: @officially.jac   Learn more about Michelle Jacobik: Website: michellejacobik.com Instagram: @michellejacobik LinkedIn: linkedin.com/in/michelle-jacobik-267724 Substack: @michellejacobik The Path To Profits Podcast: bio.link/pathtoprofitspodcast The Path to Profits Book: a.co/d/0imlGFFf The 7 Financial Mistakes Entrepreneurs Can't Afford to Make: michellejacobik.kartra.com/page/7-financial-mistakes Financial Foundations Program: michellejacobik.com/financialfoundationsprogram

  2. Oct 13

    16: Outgrowing the Life You Built in Your 20s with Brandie Campbell

    What happens when you finally build the life you spent your 20s working toward, and then realize it isn't what you want anymore? Nothing dramatic has to happen. You can have the marriage, the house, the business, and the picture-perfect life everyone else can see, and still be lying awake at night wondering if you'll feel exactly like this ten years from now. In this episode of On Second Thought, my hairstylist and friend of almost ten years, Brandie Campbell, and I talk about what it means to outgrow a life you once chose without treating the woman who chose it like she got it wrong. We get into becoming a mom at 19, choosing hair school when everyone assumed stylists were broke, ending a marriage that looked perfect from the outside, falling for a woman for the first time, and the one question Brandie asked herself a million times before she finally made her decision. Brandie Campbell is a hairstylist and the founder of Hair + Company, a full-service salon she opened in Edmond, Oklahoma in 2019 that has been voted Oklahoma's best hair salon five times. She became a mom at 19, spent five years as a single mom to two boys, went to hair school, and has spent the last decade building her career and business in the beauty industry. What's Discussed: (03:51) Becoming a mom at 19 and chasing the "white picket fence" life she never had growing up. (07:15) Why choosing what's best for you can create a better life for the people you love, too. (13:00) Refinement over reinvention, and the fear that changing your life means the old you was fake. (16:52) Going to hair school when she believed stylists were broke and working every weekend, and why it was the first decision she made for herself. (29:46) Why a marriage doesn't need one big, terrible reason to end, and why that can make leaving even harder. (35:54) The unexpected relationship that showed Brandie what it actually feels like to be seen. (1:05:13) Three questions to ask yourself if what you wanted in your 20s is not what you want now. If you made your biggest life decisions before you really knew who you were, and you're starting to admit you've changed, this one is for you.   Come sit at the table 🤍 The conversation does not end when the episode does. My Substack is where the rest lives: my raw, unedited thoughts on every episode, free, every week, plus the world I am building around style, beauty, travel, and the questions we are all actually asking. And when you are ready for the decisions, what I actually bought, booked, and believed, names and prices included, listeners get 20% off your first year prettybigthoughts.substack.com/777 Start free: prettybigthoughts.substack.com  See everything inside the community: PBT Sales Page   Learn more about Jac Pfeifer: Instagram: @officially.jac   Learn more about Brandie Campbell & Hair + Company: Instagram: @brandie.hairandco Hair + Company: hairandcompany.co Hair + Company Instagram: @hairandcompany.salon

  3. Oct 6

    15: What My Solo Trip to France Actually Taught Me

    I went to the French Riviera thinking that eight days alone might help me figure out what was next. I had just left my job and was in that messy space between an identity I knew well and whatever I was becoming next. I thought that somewhere between Saint Tropez, Antibes, Monaco, journaling, reading, and having actual space to think, I might come home with some answers. That's not exactly what happened. The trip was beautiful, but I was also more anxious and lonely than I expected to be. And while I didn't come home with a perfectly clear vision of what comes next, I learned a lot about myself along the way. In this episode, I'm sharing what eight days of solo travel actually taught me: where I feel most like myself, why I'm so uncomfortable when I'm not moving something forward, why I don't want to experience certain things alone anymore, and how a place can look absolutely perfect and still not feel right for me. In this episode I discuss: What solo travel taught me about my relationship with productivity and rest. Why I felt lonely during an objectively incredible trip. Where I realized I feel most like myself. The difference between what looks incredible and what actually feels right for me. The beliefs I'm starting to question about success, happiness, and "having it all." Why I stopped expecting the trip to answer every question about what comes next. I didn't come home knowing exactly what I'm going to do next. But I did come home knowing myself a little better.    Come sit at the table The conversation doesn't end when the episode does. My Substack is where the rest lives: my raw, unedited thoughts on every episode, free, every week, plus the world I'm building around style, beauty, travel, and the questions we're all actually asking. And when you're ready for the decisions (what I actually bought, booked, and believed, names and prices included), listeners get 20% off your first year: prettybigthoughts.substack.com/777 Start free: prettybigthoughts.substack.com  See everything inside the community: PBT Sales Page   Learn more about Jac Pfeifer: Instagram: @officially.jac

  4. Sep 29

    14: The Inherited Life vs. the Designed Life: How to Redefine Success in Midlife with Ameera Virani

    Have you ever looked at your life and thought, I have a good life. So why do I still feel like I want something different? That is such a weird place to be because nothing necessarily has to be wrong. You can be grateful for what you built, proud of how hard you worked, and still have this little voice asking whether the version of success you have been chasing actually feels like yours anymore. In this episode of On Second Thought, Ameera Virani and I get into the difference between a life you inherited and one you actually designed. Because somewhere along the way, a lot of us picked up ideas about what a successful woman is supposed to look like from our families, our culture, our careers, and the people around us. And when those ideas stop fitting, how do you figure out what you want without feeling like you have to blow up your entire life to find out? Ameera is a Certified Life Coach who spent more than 15 years helping build one of the biggest stages in personal development, working around speakers including Oprah, Tony Robbins, Richard Branson, and Maya Angelou. She also knows what it feels like to have life completely interrupt the plan. After a major loss, a health crisis, changing careers in her late 40s, and then being laid off at 50 while carrying six figures of debt, she had to decide what success was going to mean for her next chapter. What's discussed: (09:36) The subtle sign that you may be outgrowing a version of yourself. (10:15) Why success can start feeling wrong when you are measuring it by someone else's standards. (22:31) The family and cultural messages Ameera inherited about hard work, security, education, and what a successful life should look like. (36:53) What it felt like to be 50, unemployed, and carrying six figures of debt while deciding whether to go back to the "safe" path. (48:10) Why so many women in midlife are afraid of making the wrong choice when they are ready for something different. (1:06:29) Where to start when you know something needs to change but have absolutely no idea what that change is yet. (1:25:06) Why being grateful for your life and wanting more from it can both be true. If you have done everything you thought you were supposed to do and are starting to wonder, Okay… but what do I want now?, this one is for you.   Come sit at the table 🤍 The conversation does not end when the episode does. My Substack is where the rest lives: my raw, unedited thoughts on every episode, free, every week, plus the world I am building around style, beauty, travel, and the questions we are all actually asking. And when you are ready for the decisions, what I actually bought, booked, and believed, names and prices included, listeners get 20% off your first year prettybigthoughts.substack.com/777 Start free: prettybigthoughts.substack.com    Learn more about Jac Pfeifer: Instagram: @officially.jac   Learn more about Ameera Virani: Website: ameeravirani.com  Instagram: @ameera.virani LinkedIn: linkedin.com/in/ameeravirani  Substack: ameeravirani.substack.com The Design Table: ameeravirani.com/the-design-table   The Designed Life Weekly Edit: ameeravirani.com/links  The Designed Life Podcast: podcasts.apple.com/us/podcast/the-designed-life/id1832982040

  5. Sep 22

    13: How to Stop Living the Life Everyone Else Thinks You Should Want with Joy Errico

    Have you ever looked at a life you worked really hard to build and thought, Wait… do I even want this anymore? That can be a brutal thing to admit when you did everything you were "supposed" to do and became the person everyone around you expected you to be. And when everyone else still thinks you should be happy there, it is easy to question yourself before you ever question the expectations.  In this episode of 'On Second Thought', Joy Errico and I get into that very weird in-between, when the expectations you grew up with, the career you chased, the roles you took seriously, and everyone else's opinions have been in your head for so long that it is hard to tell what is actually yours anymore. And when something starts feeling off, how do you know whether you are truly ready for a different chapter or just tempted to blow up a perfectly good life? There was one question that finally cut through that noise for Joy, and it changed the way she looked at everything. Joy is the Founder and CEO of Maven Row Communications and a communications strategist and image consultant with 25 years of experience across companies including Rite Aid, Macy's, Staples, Avery Dennison, and BIC. Her work now brings strategic communications and personal presence together, helping leaders become clearer on who they are, how they want to be known, and how to show up in a way that actually feels like them.  What's Discussed: (06:31) The first clue that you might be living by someone else's standards. (12:17) The version of burnout that caught Joy completely off guard. (21:00) Why changing your life and staying exactly where you are can both come with a cost. (37:39) The question that made Joy realize she was giving herself very different advice than she would give someone she loved. (42:42) How to start separating what you want from what you were taught to want. (48:54) Why Joy stopped believing in the traditional idea of "executive presence." (1:32:03) The belief about other people's approval that she is finally trying to leave behind. If you have been doing everything you thought you were supposed to do but still feel that pull toward something different, this episode is about figuring out whose expectations have been making the decisions with you.    Come sit at the table  The conversation doesn't end when the episode does. My Substack is where the rest lives: my raw, unedited thoughts on every episode, free, every week, plus the world I'm building around style, beauty, travel, and the questions we're all actually asking. And when you're ready for the decisions (what I actually bought, booked, and believed, names and prices included), listeners get 20% off your first year: prettybigthoughts.substack.com/777 Start free: prettybigthoughts.substack.com  Learn more about Jac Pfeifer: Instagram: @officially.jac    Learn more about Joy Errico & Maven Row: Website: mavenrowcommunications.com  LinkedIn: linkedin.com/in/joyerrico/ Free Consultation + E-book: mavenrowcommunications.com

  6. Sep 15

    12: 7 Questions to Ask When Your Job Becomes Your Identity

    Have you ever cared so much about your work that a hard day, a piece of feedback, a mistake, or a moment of uncertainty started to feel personal? Maybe your job is not just a job anymore. Maybe it has become the place where you prove that you are capable, responsible, valuable, needed, and enough. On the outside, it looks like ambition. It looks like drive. It looks like high standards, commitment, work ethic, and caring deeply about what you do. And a lot of that may be true. But somewhere along the way, work can stop being something you do and start becoming the place you go to understand who you are. In this solo episode of On Second Thought, I'm sharing the 7 questions I'm asking myself as I learn to separate my identity from my work. I talk about why your job is not stable enough to hold your entire sense of self, why work anxiety can sometimes be tied to fear, validation, control, or belonging, and why there is a difference between caring deeply about your work and needing your work to prove something about you. I also talk about financial safety, performance pressure, feedback, perfectionism, being needed, feeling valuable, and what it could look like to care about work without carrying everything on your back. Come sit at the table: The conversation doesn't end when the episode does. My Substack is where the rest lives: my raw, unedited thoughts on every episode, free, every week, plus the world I'm building around style, beauty, travel, and the questions we're all actually asking. And when you're ready for the decisions (what I actually bought, booked, and believed, names and prices included), listeners get 20% off your first year: prettybigthoughts.substack.com/777 Start free: prettybigthoughts.substack.com What's Discussed: (01:33) Why I'm still in the middle of untangling my identity from work. (03:53) How ambition, drive, responsibility, and commitment can quietly turn into over-identification. (07:06) Why work is not stable enough to hold your entire sense of self. (12:19) Question 1: When did my job become more than a job? (16:03) Question 2: What am I afraid would happen if I loosened my grip? (23:40) Question 3: Am I proud of my work, or dependent on it for validation? (28:13) Question 4: What parts of myself have gotten quiet because work became so loud? (36:16) Question 5: Where did I learn that being needed means being valuable? (42:18) Question 6: What would it look like to care without carrying everything? (47:37) Question 7: What do I want my relationship with work to feel like moving forward?   Listen to This Episode If You've Been Thinking… "Why does work feel so personal to me?" "Am I proud of my work, or do I need it to prove I am enough?" "Why does feedback make me spiral?" "Why do I feel guilty when I am not being useful?" "What would it look like to care about work without carrying my whole identity through it?"   Learn more about Jac Pfeifer: Instagram: @officially.jac

  7. Sep 8

    11: Mom Guilt and People Pleasing: How to Stop Saying Yes Out of Obligation with Carla Greenan

    How many times have you said yes before you even stopped to ask whether you actually had room for it? At work, saying yes can feel like proof that you are ambitious and committed. At home, it can feel like proof that you are a good mom, partner, daughter, or friend. And when you are the woman everyone knows they can count on, saying no can bring up enough guilt that taking on one more thing somehow feels easier than disappointing someone. On second thought, maybe being capable does not mean every request deserves access to your time and energy. In this episode, Carla Greenan and I get into why ambitious women can become so used to saying yes that overcommitment starts to feel normal, where the pressure to "do it all" actually comes from, and how to figure out what deserves a place in your life before guilt makes the decision for you. Carla Greenan is a former CPA and Professional Certified Coach with 18 years of experience coaching leaders, working parents, and ambitious women through personal and professional transitions. After a 23-year career at a Fortune 500 company, where she became a founding member of its Internal Executive Coaching Team, Carla launched 3Be Coaching to help working parents move from simply surviving everything on their plate to creating careers and lives that actually work for them. What's Discussed (08:17) Why ambitious women can start believing they have to keep saying yes if they want to keep getting opportunities. (15:55) How the "good mom" standard can quietly become an impossible combination of everything we see other women doing well. (21:26) How much pressure can come from assumptions about what other people might think, even when nobody has actually asked more of you. (40:37) Why thoughts like "they will think I am less committed" can change the choices you make at work before you even know whether they are true. (49:29) The questions to ask when you know you are overloaded and need to decide what actually deserves your time right now. (56:43) How to slow down a request instead of automatically saying yes, and create room to negotiate what is actually realistic. (1:00:32) How to say no without apologizing, overexplaining, or accidentally taking responsibility for solving the problem anyway. If saying no still makes you feel selfish, difficult, or like you are letting someone down, listen to this episode of On Second Thought with Carla Greenan.   Come sit at the table  The conversation doesn't end when the episode does. My Substack is where the rest lives: my raw, unedited thoughts on every episode, free, every week, plus the world I'm building around style, beauty, travel, and the questions we're all actually asking. And when you're ready for the decisions (what I actually bought, booked, and believed, names and prices included), listeners get 20% off your first year: prettybigthoughts.substack.com/777 Start free: prettybigthoughts.substack.com    Learn more about Jac Pfeifer:  Instagram: @officially.jac    Learn more from Carla Greenan & 3Be Coaching: LinkedIn: linkedin.com/in/carla-greenan Carla Greenan's 3Be Coaching: https://stan.store/3BeCoaching   Website: 3becoaching.com

  8. Sep 1

    10: How to Know When an Opportunity Is Worth Betting On with Katie Love

    Have you ever caught yourself thinking, "I worked this hard to get here, so why am I even thinking about doing something else?" Maybe the career is good. Maybe you are successful. Maybe other people would love to have what you have. So when something new starts pulling at you, the first instinct can be to talk yourself out of it. Be realistic. Be grateful. Do not throw away everything you already built.  On second thought, maybe we have been looking at a career pivot the wrong way.  What if the better question is not whether you should leave everything behind, but whether there is an opportunity sitting inside what you have already learned? In this episode of On Second Thought, Katie Love and I get into how she knew it was time to pay attention to something new, what made her willing to bet on an industry people were still dismissing, and what she wishes women understood about following an opportunity before there is enough proof to make it feel safe. Katie Love is a former NBC news reporter and the founder of Love Social Media, the multimillion-dollar social media agency she has spent the last 10 years building. Before becoming a founder, Katie spent eight years in broadcast journalism covering crime, missing children, natural disasters, and presidential elections. Today, she leads a team of 25 and helps women-led businesses and major brands use storytelling, content, and community to grow online. She has lived both sides of this conversation: building the career she thought she wanted and then taking everything it taught her somewhere completely different. What's Discussed: (05:25) What it can feel like when the career you worked so hard for no longer feels like the place you are supposed to stay. (11:05) How to recognize the skills you can carry into your next chapter instead of assuming a pivot means starting over. (14:09) How to spot an opportunity before everyone around you sees why it matters. (18:05) What to do with the fear that nobody will need, understand, or pay for the thing you want to build. (31:24) Why slow growth does not automatically mean you are on the wrong path, and what to pay attention to before you change direction. (37:47) How to tell the difference between something that needs more time and something that actually needs a new strategy. (49:01) What to remember when everyone else's success is making you feel like yours should be happening faster. Listen to this episode if part of you keeps thinking about a different path, but another part keeps reminding you how much you already invested in the one you are on.   Come sit at the table  The conversation doesn't end when the episode does. My Substack is where the rest lives: my raw, unedited thoughts on every episode, free, every week, plus the world I'm building around style, beauty, travel, and the questions we're all actually asking. And when you're ready for the decisions (what I actually bought, booked, and believed, names and prices included), listeners get 20% off your first year: prettybigthoughts.substack.com/777 Start free: prettybigthoughts.substack.com    Learn more about Jac Pfeifer:  Instagram: @officially.jac  Learn more from Katie Love & Love Social Media: Instagram: @katielovesocial  Website: loveyoursocialmedia.com/

5
out of 5
14 Ratings

About

Welcome to On Second Thought with me, Jackie Pfeifer, a podcast for ambitious women and mothers who built a life doing everything "right," and are now questioning whether it's actually the life they want to keep living. Nothing has to be falling apart for you to question what comes next. You can be grateful for your life and still change your mind on the direction you want to take. Through honest conversations, new perspectives, and practical tools, this podcast will help you feel brave enough to question yourself, honest enough to get real clarity, and capable enough to explore new directions without blowing up everything you've built. Because sometimes creating the life you want starts with one honest realization: "On second thought, I want something different."

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