The Feminine Founder

167: {Sassy Solo} 5 Things I'd Tell My 20 Year Old Self

Caroline Pennington Season 2 Episode 168

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As we head into 2026, I've been thinking a lot about advice I would have given my 20 something year old self. In this episode I lean into 5 things I wish my 20 year old self knew. Not with any regrets, but just things I wish I would have done differently.

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ABOUT THE HOST: 

Former Executive Recruiter turned Digital Marketing Expert & Entrepreneur.  I'm here to show you that you can do it too! I help women to start, grow and scale their personal brand and business online through social media. In 2021 I launched ChilledVino, my patented wine product and in 2023 I launched The Feminine Founder Podcast and in 2025 I launched my Digital Marketing Agency called Feminine Founder Marketing. I live in South Carolina with my husband Gary and 2 Weimrarners, Zena & Zara. 

This podcast is a supportive and inclusive community where I interview and bring women together that are fellow entrepreneurs and workplace experts. We believe in sharing our stories, unpacking exactly how we did it and talking through the mindset shifts needed to achieve great things.

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Caroline Pennington (00:01.454)
All right. Today is probably going to be one of my most vulnerable episodes so far. It's only taken me 160 something episodes to get here. So thanks for hanging in here with me. But I wanted to talk about something I've been thinking about a lot this year, this quarter. For those of you that don't know, I turned 39 in December and I have really been doing a lot of reflecting of

what I wish I would have told my younger self. And I don't know, maybe it's because it's the year of the horse or we're shedding of the snake or whatever, the Chinese new year. But I really wanna talk about a couple things that I wish I would have learned or done differently and encouragement to maybe for you to do the same. So I wanted to talk about five things I would have told my younger self, specifically my younger self in my 20s, because I feel like I spent a lot of time.

doing the wrong things. And I don't know if you can relate on that, but I don't have any regrets. I'm not looking back, you know, sulking or whatever, but I do wish I spent some things or did some things differently. And I have this podcast now. I have my digital marketing business. I'm so grateful for both of those for each of you listening. I am so grateful. I wish I would have started this 10 years ago. Okay. And if you're on the fence about starting a podcast,

For sure, start a podcast. It's been one of the best things that I have done. But I wanna talk about five things that have been on my heart that I wish I would have told my 20 year old self. And number one is prioritize yourself. If you are not your best, you cannot give your best to the loved ones and people who you love in your life, okay? So that means prioritize your time appropriately. Don't let people steal your time, okay?

That is your most valuable asset and you control your time and you may be sitting there thinking like, I got kids, I got aging parents, I got whatever, fill the blank. Okay, that's great. We all have those things going on too. So make sure to protect your time. One thing that I do to protect my time is I time block. And when I time block, I do not come out of those time blocks. And sometimes the time block is only five or 10 minutes.

Caroline Pennington (02:17.592)
But if I focus on getting my tasks done in those five minutes, even if it's something small, it goes a really long way. Cause the power of compounding again goes a really long way and everybody has time for themselves every day. I don't want to hear you say, I don't have time for myself, whatever. Like I know you're doom scrolling, you're on social media. You do have the time. Okay. Or put down the Netflix or whatever that looks like, in the blank.

Also prioritize your health. If you don't have your health, you do not have anything. So make sure you feel your best. For me, I love working out in the mornings. That gives me energy. love, recently I've been doing a juice cleanse in the morning and that's been really great for me for energy levels and everything too. So make sure you prioritize your health. That is super, super important. That means getting your wellness checks, going to the doctor as needed, you know.

eating healthy, exercising, all the things because that just will help you be your best self for your work, for your hobbies, for your friends, for your family, whatever feeling that blank that looks like. But if you don't prioritize your health, you don't have anything at all. Number two, I would surround myself with people that support you. So let's say you want to start a new hobby, a new job or something different. And maybe the people around you aren't supportive of you or question you or judge you.

Those are not your people, okay? Go out and find some new people who do support you, who are on your team, who say your names in rooms when you're not there and say positive things about you, who lift each other up. I am a huge believer there's 8 billion people in this world and there is literally enough for every single person. So scarcity mindset, jealousy, whatever those fill in the blank negative emotions are, no thank you, I don't have time for it. Number three.

It's really important to have boundaries. And this is a hard one because we have people who have access to us, our family members, our friends, maybe church members, maybe people we work with and make sure that you have boundaries with these people and that's okay. Okay. And that could mean maybe you just don't spend some time with them or you don't let their negativity or whatever it is fill in the blank, their baggage.

Caroline Pennington (04:36.856)
come into your life or bring you down or anything like that at all. And again, that's hard, I know, especially with family or close friends. But again, if those close friends are not in your team or maybe talking smack about you behind your back or being jealous or catty or weird, they gotta go. You gotta find some new friends, okay? And that process is hard. I've been through that process. My friend group is completely different now in my 30s than it was in my 20s. And that's okay too. And you maybe sitting there thinking like,

Hey, I've been friends with her for 10 years. I've been friends with them, in the blank for 20 years since high school. If they are not being positive and uplifting you and supporting you, they gotta go. I don't care if they have 10 years tenure, 20 years tenure, whatever, fill in the blank, that doesn't give them the right to take up space in your life with your time, with your relationships, okay? And again, that was probably a really hard lesson I had to learn, but it's been such a beautiful thing to go through.

because now my friend group is completely different. They're completely supportive of each other. mean, the texts I receive and emails from my girlfriends now, I mean, I would have just done anything for in my twenties. Number four, stop chasing the party. When I was in my twenties, I said yes to the gala and the happy hour and those things.

Don't get me wrong. I'm not saying don't have any fun because I like to have fun too. I like to drink with my girlfriends, my husband. I like to go to the beach. I like to do fun things. So I'm not saying don't have any fun, but I'm saying stop spending your nights and weekends like onto the next party or the next time you can go do all of those things because you can find a balance there. I did that a lot in my twenties. And if I would have spent that time that I was chasing the party or chasing the next event or whatever, in the blank.

If I would have spent that time on myself, learning, growing, building like I am now, I would be 10X more than what it's currently going on. Again, not, no regrets. This is not a thing, but I'm just saying this is what I would have told my 27 year old self. Number five, and this is a hard one too. It's okay not to be the it girl. I think a lot of times we get caught up and we want to have, you know, the best looking family or the biggest house.

Caroline Pennington (06:56.282)
or the best job or the best flashy online reputation or the car or whatever fill in the blank that looks like. And it's okay not to be the it girl. Like it is okay for not everyone to like you and that's okay. And typically with me, my personality for whatever reason, people either really love me or they don't like me at all. There's no gray. And it's taken me a while to wrap my head around that.

and be okay with it, but I'm okay with it. I'm not for everybody and that is okay too. So if you're listening to this podcast and you're like, man, I feel the same way or, you know, not everyone likes me either. That's completely okay. You'll find your people and hold onto them tight. Don't let them go. Also support them in return. One thing I've learned in friendships and through my transitions in life between my twenties and my thirties is continue to give, give yourself, give your time, give your support.

give your encouragement to other people because it'll come back to you in tenfold. And I'm telling you, it is the best thing you will ever do for yourself. So thanks for listening. I appreciate you. Don't forget to subscribe and share.