On Second Thought with Jackie Pfeifer artwork

Personal Journals · Jackie Pfeifer

On Second Thought with Jackie Pfeifer

by 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."

Latest episodes

Showing 17 · updated from the feed

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 h

Oct 13
1 h 13 min

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 identi

Oct 6
27 min

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 nothin

Sep 29
1 h 20 min

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

Sep 22
1 h 23 min

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 ju

Sep 15
43 min

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 c

Sep 8
1 h 11 min

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 su

Sep 1
1 h 00 min

9: The Cost of Saying Yes to Everything with Dr. Tiffany Moon

From the outside, Dr. Tiffany Moon had built the kind of life a lot of women are told to want. She was a successful anesthesiologist with a family, friends, travel, a car

Aug 25
1 h 24 min

8: What Survival Mode Is Doing to Your Brain and Body with Robina Abramson-Walling

For a lot of women, the problem is not that they cannot handle pressure. The problem is that they have been handling pressure for so long that their body has started trea

Aug 18
1 h 15 min

7: Why Peace Can Feel Uncomfortable After Survival Mode

Have you ever made it through the hard season, only to realize your body still feels like it is waiting for the next thing to go wrong? Maybe the pressure has eased. Mayb

Aug 11
43 min

6: What Hard Seasons Can Teach You About the Life You're Building with Kayla Hale

From the outside, a woman can look like she is winning while privately carrying a season that feels impossible. She may have the business, family, reputation, growth, and

Aug 4
1 h 15 min

5: 5 Things I Wish More Women Knew About Having Second Thoughts

Have you ever looked at something you once wanted so badly and wondered why it no longer feels like a prize? Maybe it is the career path, the title, the relationship, t

Jul 28
18 min

4: How to Lead Without Carrying Everything with Annette White-Klososky

A lot of women do not realize they are over-functioning because it looks so much like leadership. They are the ones adding value, holding things together, staying highly

Jul 21
1 h 57 min

3: What Happens When the Life You Built No Longer Fits with Dr. Susan Miele

Most women do not leave the conveyor belt because things fall apart. They leave because somewhere underneath all the success, the titles, the house, the bag, the perfectl

Jul 14
1 h 23 min

2: The Success Trap That Keeps You from Trusting Yourself with Melanie Watson

For a lot of ambitious women, the hard part is not admitting they want something to change. The hard part is figuring out what is actually driving that desire. Is it intu

Jul 7
1 h 43 min

1: Why You're Allowed to Rethink the Life You Built

For a lot of women, the hardest part is not realizing something feels off. The hardest part is giving yourself permission to question it when everything still looks fine

Jul 7
21 min

Welcome to On Second Thought

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

Jun 29
3 min

Chart positions

Where On Second Thought with Jackie Pfeifer ranks today in each Apple Podcasts chart (US, Oct 15, 2026).

#102 ▲ 88 Personal Journals US

What listeners say

A curated, balanced selection of Apple Podcasts reviews.

Do you ever listen to a podcast think “how does she know me and what I am going through?” Well, that is exactly how I feel listening to Jackie. I love this show and can’t wait for more!!

hhh💕 · Aug 2026

Jackie is incredibly authentic and has a gift for going deep with her guests. Every episode creates a sense of community, makes me feel seen, and leaves me feeling empowered. Whether you’re navigating a major life change or simply looking for inspiration, this podcast will leave you feeling energized, supported, and full of female power.

Calendar issuess · Aug 2026

What a great listen as a working mom of young kids. Jackie’s voice, insights, questions and guests have me thinking about my everyday, and my future. She gives such a great perspective on what we are all capable of-even if I’m not looking to change my world. This podcast is a great reminder of the power of women, because…at least for me…I forget sometimes.

smreynolds719 · Jul 2026

Jackie and I connected on Instagram and instantly I knew she was my kind of woman. The more women like Jackie we can get in the world the better, the ones who question the script we have been given, the inner nudge that there is something more, the desire to make an impact in the world. This podcast is your weekly dose of realizing there is something more out there, and even though you might be scared, it is ok to take the leap of faith, because we are all right here with you!

Melaniewatson888 · Jun 2026

We strive to present a balanced view by showing a diverse range of reviews from Apple Podcasts.

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About On Second Thought with Jackie Pfeifer on Reason.fm

Here you find the Apple Podcasts chart positions of On Second Thought with Jackie Pfeifer, its latest episodes to listen to directly, and reviews from listeners. Rankings are updated daily for the United States.

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