Redefine Success. Redirect Ambition. Find Your People.
A small group coaching program that helps ambitious people go from feeling scared of "backsliding" in their careers to finding more space and joy—so you can finally rewrite your success story with values and priorities that truly feel like yours.
If you’re secretly wondering if you're the only ambitious person who wants to get off the career treadmill, you’re not.
And, this is why I want to get us all together!
You've tried to stop working at night, but find yourself checking email in dark mode and while getting a judgey side-eye from your dog. 👀
You've looked for permission to downshift by reading articles about people who quit corporate to start a microfarm in Upstate NY, but you don’t know what your version of a farm is and you’re still stuck worrying about the loss of high-quality health care and retirement contributions. 🚜
You fantasize about being a barista, taking a pay cut and stepping away from a higher title, but the fear of regretting it or being seen as "giving up" by Tim on LinkedIn stops you every time. ☕
Somehow, no matter how many times you think to yourself “it doesn’t have to be this way,” you still feel the constant pressure to be the professional person you think you should be, not the person you actually are. 🫤
And if you're being honest, you worry that one day it will be too late to actually live your life. 😖
Join The Intentional Backsliders Club!
You don't need another productivity hack or a new job title - you need a new way to define success and a community that gets it while you do it.
The Intentional Backsliders Club (IBC) is a 12-week small group coaching program led by me, Lindsey, where you will:
Rewrite Your Success Story: Guided conversations and curated content will help you separate what you actually want from what you've been taught you should want, focusing on your values and priorities.
Confront Your Biggest Fears: We dig into the real fears that stop you from making a change…like regret, financial insecurity, and the judgment from family and peers - and give you practical strategies to navigate them.
Find Your People: Connect with a small cohort of like-minded, ambitious backsliders who are also making intentional choices to prioritize their life, identity, and time outside of work. You'll finally have a safe space where your decisions are validated, not questioned.
The Fee, Dates, & Structure:
🛝 Duration & Cohort Size: 12 weeks of coaching and community, starting January 19, 2026. Enrollment is limited to 8–15 participants to ensure a high-touch, intimate experience.
🛝 Your Investment: $300 for this initial cohort.
🛝 Format: A blend of self-paced content (delivered via a dedicated portal) and live group coaching and discussion on Zoom.
What the 12 Weeks Look Like:
Self-Paced Content: Every other week, you will receive new content in your private portal. This includes curated readings, podcast episodes, reflection prompts, and practical tools designed to spark deep insights and prepare you for our discussions.
Live Group Sessions: We meet every other week on Zoom for 75 minutes of guided discussion, light coaching, and meaningful connection with your cohort.
Time: 7:00 PM EST
Upcoming Zoom Dates:
Thursday, January 22, 2026
Thursday, February 5, 2026
Thursday, February 19, 2026
Thursday, March 5, 2026
Thursday, March 19, 2026
Thursday, April 2, 2026
Logistics Handled: You'll receive a reminder email and a calendar link for every Zoom call, so you never have to worry about missing a session.
The Content & What We'll Explore
This program goes beyond career talk. We're digging into the fears and deep-seated beliefs that hold you to the traditional path.
Over 12 weeks, you'll be guided through handpicked content—readings, reflections, and tools - the same kinds of things I leaned on while redefining success for myself. We’ll also have powerful group discussions and light coaching to help you rewrite your definition of an ambitious and successful life.
We will lean on my 11 years of coaching experience to address the complex intersections of work, money, and identity.
Deconstructing "Workism":
We'll explore where your ideas about ambition, success, and self-worth actually come from. You'll learn to distinguish between what you truly want versus what you’ve been taught you should want by society, parents, or LinkedIn.
Navigating the Tradeoffs:
We'll dig into the very real concerns you have about stepping back, including the financial fears, loss of high-quality benefits, and retirement savings. You'll develop practical strategies for making intentional, sustainable choices.
The Identity Shift:
We address the toughest emotional fears: the loss of identity that comes with letting go of a high-status role and the constant worry about what other people will think of your choices.
Putting It Into Practice, Imperfectly:
Stepping off the treadmill is one thing; staying off is another. We'll transition from discussion to action by helping you create a sustainable, imperfect plan for your next step.
Beyond Regret:
You'll hear real stories from people who have successfully chosen a different path—what pushed them to change, how they handled the tradeoffs, and what their life looks like now—to help you move beyond the fear of regret or failure.
Defining Your New Success Story:
You will be guided to rewrite your own success story with language, values, and priorities that are authentically yours, allowing you to be ambitious about the things that truly matter, like rest, creativity, and deep friendships.
Want in?
Join the January 2026 Waitlist
I’m limiting the group size to ensure a high-quality, intimate experience, and spots for this initial cohort will fill quickly.
Click below to secure your spot on the waitlist and be the first to know when enrollment opens.
FAQs
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Then this is the place for you! There are sooooo many things in life to be ambitious about. Cultivating community and friendships, having hobbies, resting, I could go on and on…
And if you want to be ambitious in your career, what if you also got ambitious about work boundaries so you don’t burn out?
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Absolutely not. Unless you ask for the encouragement, this is a no pressure zone.
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Nope! This is not secretly a “become a freelancer or entrepreneur” program.
Unless that’s what you actually want to do. :) -
I’m working on the timing of the Zoom calls right now. (If you haven’t weighed in, do so here.)
If it turns out that you’re unable to make the time, that stinks and I’m sorry. 🥺In my opinion, the community and new friends you’ll make during this program is the magic sauce.
If you’re unable to make 2 or more of the six Zoom calls, I recommend holding off on signing up.
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Good question! Every other week, you’ll get content centered around a theme. It will be a mix of different resources that have been helpful to me.
I encourage you to peruse what’s there and decide what you want to dive into, so how much time you spend is up to you! We’re backsliders, after all. 😉
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Not at all. This program is for anyone rethinking ambition/success, not just job-switchers.
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We address the fear of financial impact head-on, but this is not a personal finance program. I will give you a framework on how to run your numbers, but that’s something you can do on your own, between Zoom calls.
Many people are stopped by the anxiety around money, so we dedicate time to:
Confronting the worries about pay cuts, losing high-quality benefits, and affecting your family budget, providing you with ideas on how to navigate those conversations.
Giving you the resources and a framework to figure out what your next intentional step needs to look like financially. I can help you organize your thoughts and identify the right financial professionals (like a financial planner) you need to consult for personalized, expert guidance.
Meet Your Facilitator
Hi! I’m Lindsey. I never thought I’d be starting a club with the word “backsliders” in it, but here I am. I’ve been chasing gold stars for as long as I can remember.
I chose the word “backslider” because that’s what we tell each other (and ourselves) when we take our foot off the career gas pedal.
“I’m scared I’ll backslide in my career.”
I can’t tell you how many times I’ve heard those words in the last 11 years of coaching calls. Or how many times I’ve said these exact words to myself.
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My Story: Why I Started The Intentional Backsliders Club
For the last four years, I've drastically changed how I approach my career, business, and ambition. My life is so much better for it: I've deepened friendships and finally feel connected to the "whole me," not just who I thought "career me" should be.
The Catalyst
On the outside, I was performing - laughing, smiling, and succeeding - but inside, two things became impossible to ignore:
My Own Burnout: I was working way too much (often at night, too), had very little energy left for my partner and friends, and couldn't kick the terrifying feeling: "Is this what the next 25 years are going to look like?"
A Wake-Up Call: My best friend, a successful medical professional and administrator, became disabled due to complications from Long Covid and career burnout. Watching her lose her career has forced her to redefine her sense of purpose and identity and I’ve been along for the ride. To be honest, I took it as a personal warning.
The Shift
I realized the true risk wasn't "backsliding" - it was continuing to do life the same way I was doing it.
So, I did something about it. I got off the WORK > LIFE treadmill and found a new way to be ambitious.
I created the Intentional Backsliders Club because I want to share the resources that helped me make this shift and build a community with like-minded people.
This program is for anyone ready to explore being ambitious about the things that truly matter—not just what they do for a job.
I hope you join us!
