133: From Weight Shame as a Child to Food Freedom as an Adult: Lindsay’s Journey with Drop It Club

In this episode, I sit down with the amazing Lindsay for a real, honest, and super inspiring convo about her journey with food, weight, and self-love.

If you’ve ever struggled with yo-yo dieting, shame around eating, or just trying to “figure it out” when it comes to health, this episode is for you.

Lindsay opens up about her childhood trips to Weight Watchers and rigid food rules to investing in an expensive nutritionist who asked her to treat hunger like a math equation (hard pass). For years, she searched for answers and tried everything from rigid diets to rigorous exercise. When she noticed we were offering a plant-powered weight loss program, she was all over it. 

That’s when everything shifted.

With the help of Drop It Club,  Lindsay discovered losing weight doesn’t have to be about restriction and guilt—it can actually be joyful, empowering, and delicious. Since starting Drop It, she’s down over 25 pounds, feeling amazing, and her whole family is loving the plant-powered meals, too (including her husband, who’s down 60 pounds!).

We hope this one leaves you feeling hopeful, fired up, and hungry for a big ol’ plate of badass loaded fries.

Helpful Links:

• ⁠⁠Join Drop It Club⁠⁠ Use code PODCAST at checkout for $100 off your first 3 months if you purchase by June 1, 2025.
• ⁠⁠Sweet Potato Stuffed with Creamed Spinach⁠⁠
• ⁠⁠Breakfast Porridge ⁠⁠
• ⁠⁠Sesame Ginger Baked Tofu⁠⁠
• ⁠⁠Caramel Pecan Cheesecake⁠⁠
• ⁠⁠Badass Loaded Steak Fries⁠⁠

Transcript (auto-generated, may have grammar errors)

Molly (00:01.678):
Hey there, and thank you for listening to this episode of the Clean Food Dirty Girl podcast. Today, I have Lindsay, who has been in our Drop It Club since we started in January. We’re going to talk today—you’ll listen, get inspired, and maybe even have some aha moments.

Lindsay Oakes (00:19.627):
Yes.

Molly (00:31.074):
I’m super excited to talk to you, Lindsay. Thank you for being here.

Lindsay Oakes (00:39.265):
Thanks for having me. I’m really excited.

Molly (00:42.218):
What made you sign up for Drop It when you saw we were doing it?

Lindsay Oakes (00:49.575):
I was so excited when I got the email before the holidays. I had been working with a nutritionist, unsuccessfully. I’ve been vegan for years and struggled with my weight. I saved up money, worked with the nutritionist, but wasn’t losing weight. There were rules but no backing: eat five times a day, eat every few hours, only eat until hunger is a 7 out of 10—I didn’t even know what that meant.

When I got your email, I thought, this is great. I was looking for someone vegan and support from a group who eats plants. It came at the perfect time. I could go into the new year with people who eat like me and know how to do it in a healthy way.

Molly (01:54.604):
Yeah, it’s such a niche thing. I’m so happy you joined us. This is a plant-powered approach. Anyone can join, but it’s not for everyone. If you eat plants and struggle with your weight, you don’t have to compromise or educate someone on how you eat.

Lindsay Oakes (02:41.129):
Right. I believe in these plant-based principles. Being told to eat a couple of treats each week didn’t work for me. Once I eat a little treat, I want a hundred. Nothing was aligning with who I am.

Molly (03:04.876):
That’s such a good point. It’s important that the change feels right. Some people talk to nutritionists and aren’t sure, but I say: go with what feels right in your gut.

Molly (03:32.896):
When you started, did you have a goal in mind? I think there was a vacation?

Lindsay Oakes (03:46.837):
Yes. My daughter, the youngest of seven, is graduating. She wanted a spring break trip with just mom and dad. Early on, I started losing weight and aimed to lose 25 pounds by our trip to the Caribbean. I’m down 23.3 now. I only weigh monthly, but it’s consistently gone down. I don’t have to worry about my suitcase—it’ll all fit.

Molly (04:43.988):
Hell yeah. And your vacation is April 15th, right?

Lindsay Oakes (04:50.717):
Yep. And we’re going away again in July. My goal is to lose another 20 pounds by then.

Molly (05:03.414):
It sounds like it’s been easy, but I know it hasn’t. Tell me about past weight loss attempts and how this has been different.

Lindsay Oakes (05:26.325):
I’ve tried everything. I’ve always struggled. My mom took me to Weight Watchers in elementary or middle school. There was so much shame. I remember not eating enough or starving while trying to make everything healthy. As an adult, it continued. I’d gain and lose weight, exercise, get divorced, stop exercising—cycles that never ended.

Molly (06:25.646):
So many people have similar stories—moms taking them to Weight Watchers. It’s scarring. There’s shame that sticks. And it’s always that pattern of losing and gaining.

Lindsay Oakes (07:19.593):
Always. Just lots of changes, lots of rules. That’s what’s different this time. There aren’t many rules.

Molly (07:29.966):
Right. In Drop It, there are three phases—plus the initial prep. You go through them as needed. What phase are you in?

Lindsay Oakes (07:59.457):
I call it phase 1.5. I was struggling to give up nuts. Coconut was easy, but not nuts. So I started choosing recipes without them or substituting cashews with hemp seeds. I made it manageable—if it doesn’t taste good, I won’t eat it.

Molly (08:40.098):
Totally fair. It has to taste good. Giving yourself grace is key—it didn’t take a month to gain, it won’t come off in a month.

Lindsay Oakes (08:45.611):
Exactly. These changes are sustainable for me.

Molly (09:11.446):
There’s flexibility within this plant-powered structure. You’re doing what works for you. That’s so important mentally.

Lindsay Oakes (10:04.585):
Totally. I’m big on meditation and breath work. My teacher says, “There’s always a voice giving you another job.” I started noticing how often I’d go to the pantry—out of habit, not hunger. I’d just eaten. It’s all about awareness.

Molly (10:57.164):
Yes. Feelings are a huge part of this. We eat to make feelings go away—boredom, sadness, desire. Were you doing that before?

Lindsay Oakes (11:49.687):
Absolutely. Then I’d criticize myself: “No wonder you’re fat.” That self-judgment was huge. I had to ditch it and find compassion for that little kid in Weight Watchers.

Molly (12:45.932):
That’s beautiful. We get to give ourselves what we didn’t get back then. What do you think helped you realize this during Drop It?

Lindsay Oakes (13:15.083):
A few things. The guidelines helped give me a structure. I’m also a psychotherapist, so I’ve done a lot of inner child work. And I’m getting older—I want to move, walk up stairs, visit clients without gasping. My parents are active in their 70s. I want that, too.

Molly (14:34.156):
That’s so important. It’s not just about the number on the scale. Have any guidelines or batch cooking felt hard?

Lindsay Oakes (15:15.959):
Letting go of coconut milk was tough. Curry was our weekly lunch date. We’d have martinis and fried appetizers. Now, I still go out, but I ask for steamed veggies, no oil. I plan meals from Clean Food Dirty Girl—90% of what we eat is from there. My daughter loves the cheesy sauces. The whole family’s eating better.

Molly (17:23.32):
What an example you’re setting. You once said, “Losing weight this way is delicious.”

Lindsay Oakes (17:52.117):
It is! Last week we had badass loaded fries and I’m losing weight. My daughter was upset my husband ate the leftovers!

Molly (18:41.806):
That’s such a shift from dieting—now it’s about eating good food and being satisfied. Did that feel foreign at first?

Lindsay Oakes (18:50.741):
Yes. I thought I had to restrict. But I learned I didn’t. Now I don’t crave. I have energy. I walk my dogs at sunrise. Six months ago I hated exercise.

Molly (20:54.19):
It really is a lifestyle change. It sneaks up on you. Just one processed meal and the cravings return. Plants don’t do that.

Lindsay Oakes (21:42.441):
Exactly. I haven’t overeaten since starting. I used to shovel pizza in, drink a lot—filling a void. Not anymore.

Molly (22:18.348):
And that’s what makes this sustainable. You’re choosing what works. You’re not deprived.

Lindsay Oakes (23:29.879):
Right. 90% of our meals are from the portal. I tried to wing it—two weeks in, I needed the full plan. My daughter brings Clean Food Dirty Girl meals to school. Sunday is our taco night with tofu crumbles, beans, and cheesy sauce.

Molly (24:41.942):
Love it. You’re investing in yourself. That’s the best gift.

Lindsay Oakes (25:44.309):
It is. Even out on the road, I make smart choices. Like getting a bagel scooped out with veggies—imperfectly perfect.

Molly (26:54.988):
Yes, that’s what it’s about. Doing your best with your circumstances. You can still reach your goals.

Lindsay Oakes (26:58.485):
The hardest part of this lifestyle is watching what others eat—so much junk. Then they have health scares and go back to eating the same way. It’s frustrating because people just don’t have the knowledge.

Molly (27:23.062):
So true. Many think this is really hard or don’t want to give up bacon, cheese, etc. The transition can be tough, but that challenge doesn’t last—especially when you feel better and enjoy life more.

Lindsay Oakes (27:59.125):
It feels effortless now. My energy is through the roof. I used to sleep nine to five. Now I get up, walk my dogs at sunrise. A 10-minute walk becomes 45. I love it. The changes feel good, not forced.

Molly (28:27.724):
You’ve really found your flow.

Lindsay Oakes (28:29.717):
I love it so much. I’m so grateful it came at the right time.

Molly (28:37.804):
It’s been joyful witnessing your transformation. It may have started with a weight goal, but it’s morphed into something bigger. That weight is never coming back.

Lindsay Oakes (29:32.117):
Exactly. I follow a few key guidelines—no more fried food. I speak up about food needs when going out. I focus on the experience, not just what I eat.

Molly (30:04.142):
Have you felt more confident advocating for yourself with food?

Lindsay Oakes (30:18.939):
Definitely. I speak up more in general now. At restaurants, I ask for what I need or choose something else. It’s more about the experience than the food.

Molly (30:48.46):
That mindset shift is huge. The food might not be perfect, but you’re there for the connection.

Lindsay Oakes (31:32.439):
Totally. I used to think oatmeal was boring—now I’m excited about millet porridge with buckwheat. Even my husband eats it and loves it.

Lindsay Oakes (32:00.863):
He’s had health issues and resisted going vegan. I got him to agree to 30 days. He lost 60 pounds eating Clean Food Dirty Girl meals and never went back.

Molly (32:47.916):
That’s amazing! It shows the power of good recipes. I’ll toot our horn—we’ve got the best WFPB recipes out there.

Lindsay Oakes (33:07.351):
Hands down. There are 50 types of cheesy sauces! It’s unreal.

Molly (33:24.622):
And now millet porridge is normal, not weird. I grew up with it thanks to my hippie mom. I love sharing it with others.

Lindsay Oakes (34:06.519):
My husband now buys me nut milk makers and tofu presses for Christmas. I make a hemp latte with cacao and dates when I want something sweet—it’s indulgent but healthy. A few months ago, I would’ve doubted I’d be here.

Molly (34:54.478):
So this has been a surprise for you?

Lindsay Oakes (35:01.023):
Totally. I’d tried so many things. A nutritionist wanted $12,000 to tweak every meal. Who has time for that?

Molly (35:25.23):
Exactly. It shouldn’t be hard or unsustainable. This is the opposite.

Lindsay Oakes (35:33.783):
She said eat until you’re 7 out of 10 full—I don’t even know what that means!

Molly (35:50.996):
Right! With us, there’s no counting or calculating. Just eat until satisfied.

Lindsay Oakes (36:01.993):
Exactly. When I’m busy, I do component cooking: rice, potatoes, sauces, chopped veggies. I come home, microwave for two minutes, and I’m good. No more chips or granola bars for dinner.

Molly (36:43.618):
Yes! I do that too—some weeks I follow the meal plan, some I just batch components. It’s still so satisfying and quick. It’s crazy how good and easy this is.

Lindsay Oakes (37:44.759):
Same. I had a 5 a.m. meeting today, cooked an eggy casserole with sunny side up sauce, tempeh bacon, veggies. Took some on the go—came home, it was gone. But it’s worth it. It’s easy with the right tools.

Molly (38:33.762):
Yes! And we have to eat anyway. Why not make it nourishing?

Molly (39:05.198):
Your hemp cacao drink is a great comfort swap. This way of eating still lets you indulge—just in a better way.

Lindsay Oakes (39:39.953):
People think it’s just broccoli and water. But I get my protein! I’m in the Rancho Gordo Bean Club—always stocked. I never feel deprived. We make caramel cheesecake from the portal for holidays. I don’t feel the need to cheat or “take the night off.”

Molly (40:31.566):
Exactly. You’re not relying on vegan junk food anymore.

Lindsay Oakes (41:07.049):
Totally. I had to ride out cravings early on—used the craving jar and haven’t needed it in a while. The options are endless.

Molly (41:19.362):
Yes, the craving jar is a great tool. At first you use it a lot, then less and less.

Lindsay Oakes (42:12.971):
I wasn’t going to do it, then I did—and it helped. I still haven’t emptied it. I don’t go to the pantry anymore. I see my success right there.

Molly (42:41.954):
That’s so powerful. The alcohol, too—many people turn to it for stress. But now you’re getting that satisfaction from walking, nourishing food, and connection.

Lindsay Oakes (43:15.455):
Exactly. I used to want to park right outside. Now I gladly park two blocks away to walk more.

Molly (43:24.142):
Yes! It doesn’t suck to live like this.

Lindsay Oakes (43:45.355):
It really doesn’t. A big part is letting go of control. There’s so much we can’t control—but we can work on ourselves. Meditation is my non-negotiable now. I sit, check in, and process. I’ve evolved into a whole person.

Molly (44:30.636):
That’s amazing. It helps not just with food, but with relationships and how you show up in the world.

Lindsay Oakes (45:08.319):
Yes, people say I’m more present. I used to eat the whole pizza and say I’d start again tomorrow. Now I remind myself—this isn’t the last time I’ll eat it. I don’t have to eat it all now.

Molly (45:38.57):
That’s a huge shift. And the presence—that’s everything.

Molly (45:59.126):
If you’re present and patient, it’s so amazing what you’ll discover about yourself. You never know what you’ll uncover through this process.

Lindsay Oakes (46:14.113):
If I could go back to myself in Weight Watchers, I’d tell that little girl she was good enough. I think the message I got was that I wasn’t enough. Now, I try to operate from a place of—what if nothing is wrong? What if this is just the way it’s supposed to be? I’ve learned to be okay, even when I’m not okay. I give that little version of me the love and support she needed.

Molly (46:59.116):
Yes. You can love and accept yourself and still have a goal to lose weight. That’s a big misunderstanding—that self-love and growth are mutually exclusive. They’re not.

Lindsay Oakes (47:34.679):
Exactly. I see people happy in larger bodies, and that’s fine. I love myself. I have boundaries. I’m successful. But I want to feel even better. I want more—not to settle. A lot of weight issues come from childhood when emotional needs weren’t met, and food was the comfort. I have a loving marriage, my family accepts me, but I want to evolve. Why shouldn’t we want to become better?

Molly (49:00.942):
Yes, for the experience of it. For becoming someone who eats millet and walks more and feels joy in that.

Lindsay Oakes (49:40.585):
Right. And giving yourself grace. No one’s perfect. You can always start again in the very next moment. I’m not saying I’ll never eat a chip again, but right now, I’m not. I’m not following rules—I’m just loving myself more, and that makes me better for everyone around me.

Molly (50:22.35):
That’s so powerful. You really embody what this program is all about—compassion, love, sustainability. Not shame.

Lindsay Oakes (50:57.495):
I’ve never been skinny—that’s not my frame. But I can be healthy in the body I choose.

Molly (51:09.344):
Yes. It came to you at the right time. You trusted the process, put in the work, and look at the results. I’m so happy for you and your family.

Lindsay Oakes (51:38.113):
Thank you. It’s also about stopping and recognizing the wins. That’s something I never did before. I’d always revert back. But now, I see it. My jeans are a size down. I can pull them on without unbuttoning. I look at my body and I see change.

Molly (52:23.51):
Yes! And the towel moment!

Lindsay Oakes (52:28.413):
Yes! I hadn’t wrapped a towel around me in years. One night I did, and it fully closed. My husband thought I was nuts because I was so excited. But it’s these little wins that mean everything.

Molly (52:53.87):
We love celebrating both scale and non-scale victories. Those little things are what build your confidence and help you stay on track.

Lindsay Oakes (53:31.755):
Totally. Someone else in the group is walking to work every day—that’s amazing. We’re all in this together. That camaraderie helps. Even if we have different lives, the struggles are similar. You’ve built something that supports the whole person.

Molly (54:16.492):
Thank you for saying that. That makes my heart so happy.

Lindsay Oakes (54:19.647):
I’m so grateful. I dreaded meetings with my old nutritionist because nothing was working. But here, everything has clicked.

Molly (54:32.48):
You’re not alone in that. I’ve heard that from others too. There’s definitely a secret sauce to this. And watching replays of our connection calls helps because the themes are universal—even if the details differ.

Lindsay Oakes (55:37.237):
Exactly. We don’t need the same trauma to be relatable. That’s the beauty of this group.

Molly (55:44.59):
So true. Thank you, Lindsay. I’m so glad you joined me today. People need to hear this—it is possible to lose weight in a compassionate, empowering way without feeling deprived.

Lindsay Oakes (56:17.557):
Right. And it’s worth the investment. I can skip one mani-pedi a month for this. And when I lose the 100 pounds, you’ll have to bring me back!

Molly (56:37.434):
Deal! You’ll definitely be back for a follow-up episode. Enjoy your vacation and please post pictures. Thank you for sharing your journey.

Lindsay Oakes (56:46.455):
I sure will. Thank you.

Lindsay Oakes (56:53.195):
Bye.