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On Second Thought with Jackie Pfeifer

On Second Thought with Jackie Pfeifer

By: Jackie Pfeifer
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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."2026 Biographies & Memoirs Personal Development Personal Success Social Sciences
Episodes
  • 13: How to Stop Living the Life Everyone Else Thinks You Should Want with Joy Errico
    Sep 22 2026

    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

    Show more Show less
    1 hr and 24 mins
  • 12: 7 Questions to Ask When Your Job Becomes Your Identity
    Sep 15 2026

    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

    Show more Show less
    44 mins
  • 11: Mom Guilt and People Pleasing: How to Stop Saying Yes Out of Obligation with Carla Greenan
    Sep 8 2026

    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

    Show more Show less
    1 hr and 11 mins
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