In my first real job, I seemed to constantly have to have this same conversation. (I say first real job because I had 4 different jobs in my first year out of college which I always like to share for anybody in the early stages of their career and feeling like everybody else has it all figured out. This is your reminder that most people's reality is messier than it looks!) I would talk with my boss about what was next for my growth and we would come to the same point. I was great at pitching...
2 months ago • 2 min read
This email is years in the making, Reader! In fall of 2023, I was coming to a pretty painful realization - I wasn't very happy. I was living in NYC, had great friends, a beautiful apartment, was working for myself and traveling regularly but I was just feeling BLEGH. And that malaise, that funk, was growing every month. I had always known that I didn't want to live in New York forever (I'd just never envisioned myself raising kids in NYC and I really want to be a mom someday) so I'd known...
3 months ago • 2 min read
We're baaaack! I'm coming to you fresh in 2025 from Charleston, my potentially final stop on the "where is Samantha going to live next" (if you missed this story, there's a little more context in this video). I'm also sending love to anybody affected by the LA fires - it's been heartbreaking to watch so I know it's 100x more devastating for those affected). If you're feeling overwhelmed by what's going on, feel free to snooze this email and come back to it later - your mental health matters...
4 months ago • 3 min read
So a few weeks ago, I went scrolling. Not on social media (although let's be real, I did that too). This time I went back waaaaaay back into my archives of articles I've written since being a "creator" on the internet. And y'all... it's a funny thing, because I looked back at the very first article on my website and I learned some things. From my past self! So I figured I'd share some of the key observations (and of course, I'll link the full article down below)... Almost three years ago...
4 months ago • 2 min read
Hello from Nashville, Reader! I made it to the next stop on Samantha's world tour. If you missed it, I'm auditioning cities to be my next home base so for about the next month, I'll be living in Nashville. I can say that we're off to a great start - you know when the logistics just work and it makes you feel like a little bit of a mastermind? I had a bit of that experience in getting to my temporary apartment while here. Feels great :) But as a result of all the travel I've done in the last...
6 months ago • 1 min read
If you're anything like me, Reader, then at some point in your life (maybe right now!) that desire to shut it all off can be very real. If you're sitting here wondering, wait, who is this person in my inbox again? My name is Samantha Pillsbury. You may remember me from my coaching business helping high achieving women build more confidence in their personal, professional and dating lives. Well, after over two years of building and running that business, I decided to just stop and take a...
6 months ago • 3 min read