WISE ADVICE SINCE 1992
You’re not alone.
The doubts, feeling overwhelmed, burnout and worrying if you’re “good enough.” We’ve been there. But now we’re here to share stories, lessons, helpful tips and tools to help all of us chart a new path.
CATEGORIESConfidence Dating Money Productivity Travel
GUIDE
Want to run your own BFF board meeting?
This tradition helped my friends and I build workout routines, finish drafting a book, heal relationships with family and much more. Turns out, the difference between just saying the goal and getting it done were in a few tweaks.
This guide will walk you through how we set up our BFF Board Meetings, questions to ask each other and what made the difference in us actually following through so you can make the same leap. (And the guide has a bonus for those who don’t currently have besties to Board Meeting with so you can get started solo if needed!)
For the people pleaser, perfectionist, overachiever eldest daughter who’s ready to trade hustling to prove herself for more peace, confidence and calm
Because let’s be honest, being everything for everybody, caring what other people think, anxious attachment and hustle culture is really exhausting.
We get it.
Recent Posts
The Nantucket Guide
There is nothing like summer on Nantucket. It is truly my happy place. A lot of Nantucket charm is the insider spots, the hard to find beaches and the unfinished moments, so I absolutely recommend not trying to overschedule your time on the island. Time is supposed to slow down on the island - enjoy it!
The most common sign that you care too much what people think
The number one sign that you care too much what other people think is if you spend a ton of time trying to predict what they’re thinking and feeling. In short, trying to read minds. Now before you click away, you might be thinking - “uh, yeah, stating the obvious, if I care what other people think, I spend time trying to figure out what they think.”
And there, my friend, is the issue.
I started enforcing way stricter boundaries. This is what happened next.
If you hear all this talk about why boundaries are important but want to really understand what it means to set a boundary and what might happen when you start communicating boundaries in your friendships, relationships and work life, this post is for you.
Behind the scenes: my favorite journal prompts as a former people pleaser
Do you wonder whether journaling can help mental health? This will talk through why it’s so beneficial if you struggle with overthinking, anxiety and people pleasing and detail the actual journal prompts a mindset and confidence coach uses for her own reflection (and why they’ll help you move towards more confidence).
Why you should start asking for more perks today (and how to get started)
If you want access to the network of free stuff, rewards and benefits, it all comes back to cultivating your ability to ask for what you want. Getting over your fears around rejection or what people will think is the key to more confident, a more luxe life and more ease day-to-day
On being messy (Behind the scenes of the mindset challenges of entrepreneurship)
I’ve been thinking a lot over the past few weeks about my business, my lifestyle, what I want for myself long term. And I will admit that there were a solid weeks at least where I was considering shutting this business down and starting from scratch. But I realized I’d be doing y’all a disservice if I wasn’t open about what’s been going on in my head as I’ve navigated the last 9 months and the biggest learning I’m working through personally because I know that you probably need to hear it as much as I did.
Is this deadline stressing you out? Unpacking the pressure around turning 30.
Society puts enormous pressure around our thirtieth birthday. Expectations around getting married before thirty or what you should be earning by thirty can be debilitating. I’m breaking down on my thoughts on the deadline and what to do about it.
The secret ingredient to having successful conversations
Because we cannot control the entire world around us, in order to be successful (i.e. have the lifestyle, love, income, schedule, etc. that we desire) we have to learn how to work WITH a world that we do not control, not struggle AGAINST it. So how do you get the world do what you want it to do?
4 Reasons You Keep Getting Overlooked (and How to Start Getting the Attention You Crave)
Unpacking the common reasons why you might be being overlooked for promotions, dates and generally not getting the attention you desire. If you are tired of being the good girl, helper, dependable one but don’t know what you’re doing wrong to be so invisible to your coworkers and men, read this to figure out how to get people to pay attention to you more.
How to stop letting overachieving from making you miserable
If you are an overachiever that’s tired of feeling burnt out and exhausted, you need to understand that the way to stop people pleasing and how to find a partner who will carry his half of the bargain is in looking at the danger of overacheiving.
Are you playing it safe?
This is a question I ask myself, and often clients, fairly regularly. But before we dive in too deep on it, let's clarify one thing: there's a helpful and unhelpful kind of safe. The helpful kind of safe is more like “supported.”
This might be what's making it harder to be confident!
If you want to be confident, at some point we have to accept that we will face hard things in life. Setting expectations of what things feel like will help us feel more confident when we face the inevitable challenges.
My biggest reflections from finally taking a week off
Some in-depth, honest reflections as I ease back into business as usual after taking a week.
You have already been admitted to the club of “good enough.”
This was something that had been explained to me over and over again but now I was living it in real life. It was my freshman year at Yale University. We were all living in buildings that looked like castles, navigating living away from home for the first time, looking around eagerly at the people who people had said may be “friends you'll have for the rest of your lives.” And all around us hung a question: What made each of us good enough to be accepted here?
The lie we’ve been told about feeling better about yourself
But here's the thing we need to talk about: the idea that transformation requires some external magic - whether that's the perfect partner, the right opportunity, or even the ideal self-help program - is actually what's keeping you stuck. Which is why today we're diving into why you already have everything you need to create the confidence, dating success, and career fulfillment you're craving, with a little fairytale storytelling along the way!
What to do if you’re overthinking your text messages
When you're in the early stages of dating (we're talking dates 1-5), do you find yourself constantly analyzing the text conversation, thinking in great detail on the right thing to say, how frequently to text, etc.?
Dating is not a test to pass
Dating is not a test to pass. Why does dating seem to be such a kryptonite for the confidence of high-achieving women?
The Dallas Guide
A list of some of my favorite spots from my hometown! An often underestimated city in the US for food, culture and much more.
Dating advice to stop giving and what to say instead
Nobody wants to give bad relationship advice but sometimes, we can be speaking from our current feelings - good or bad. So we're going to do a quick recap of dating and relationship advice to stop giving and what to say instead.
The stigma of solo
While solo travel can help you get comfortable being alone, its most powerful benefit is learning to be comfortable with being challenged. And in this way, my philosophy toward solo travel and dating converge.
QUIZ
Which type of eldest daughter are you?
Regardless of whether you were actually born first, you’re probably here because the eldest daughter archetype feels so friggin’ real to you.
But here at Eldest & Co., we’ve come to realize that there’s actually a couple of different types of eldest daughters and that figuring out which one you are can be key to figuring out how to unlock your next big phase of growth!
FEATURED TOOL
A game changer for finally releasing those stubborn limiting beliefs
You know what your patterns are, you know what the fears are but how do you actually go about shifting those subconscious beliefs that dictate how we act when we’re triggered or emotional?! Turns out, it’s not about understanding as much as it’s releasing emotions from when you picked them up in the first place. There’s so many tools out there that claim to do this, but honestly, this is the one I keep coming back to. It doesn’t hurt that it can fit in pretty much anybody’s budget. (Plus the code SAMANTHA gets you an extra 15% off!)
Your simple plan to stop living to please.
Whether you’re on day 1 or 1000 of your recovering “good girl” era, the no brainer place to start is my mini-course, “Debunking the Need to Please”.
Every day for the next 6 days, I’ll drop a juicy email in your inbox with some of my biggest aha’s, some of the practices that have helped me and the important reminders, specifically for the overachiever type, to help you really understand what it’s going to take to tackle that people pleasing and stop caring so much what other people think. The best part, it’s totally free.
WHAT OTHER GIRLIES SAY
“Samantha was instrumental in helping me change my thoughts about myself and my self-worth. These are techniques that I'll be using for a long, long time!”

