I'm Back and Baby I Brought Context

I’m writing this week’s episode of What Sheridan Said, whether I’m ready, you’re ready, the world is ready, or not…and I already know it needs context. This is the first episode of season two, and I haven’t written to you since just before my birthday (December 20th, put it in your calendar and send me flowers). The following Wednesday was Christmas Eve, then the next one was New Year’s Eve, and then the week after that, I didn’t write at all because I was mentally spiraling, something we will get to later. There are reasons for the gaps, I don’t want to pretend there aren’t, but I also don’t want to rush past them just to arrive at something cleaner or more convenient.

So, my birthday.

As you know, my birthday sits right next to Christmas, which is one of those things that sounds minor until you live it year after year. People are busy. Plans are already made. Everyone is traveling, exhausted, or mentally checked out, and you learn early not to expect very much. This year, though, something different happened. I went out with new friends I’d made at work, and we actually went out— drank, laughed, celebrated— in a way that felt normal, grounded, and human. That might sound small, but it isn’t. I can’t remember many birthdays where I wasn’t working, navigating unexplainable chaos, or simply surrounded by people who weren’t really available or my friend. Christmas birthdays will do that to you. So will a life that has never stayed still.

It felt good— genuinely good. I don’t want to overstate it, but I also don’t want to minimize how much it mattered to feel present on my own birthday instead of treating it like something to survive, a day to make it through.

New Year’s Eve happened in Atlanta. I don’t need to spill the juicy details to you publicly. If you know, you know. If you don’t, you don’t need to.

The first season, the last season of What Sheridan Said began on what felt like a real high. My career was moving in the right direction. I was working as a business and startup advisor, lining up opportunities, and living in a home I genuinely loved. I had friends. I had routines. I had a sense that I was growing into myself instead of constantly shapeshifting to fit whatever environment I was in. It felt like momentum; I felt like I earned it.

And then everything fell apart, slowly, then all at once.

My safety became a question— not metaphorically, not emotionally, but practically. Logistically. Enough that I had to make fast decisions that weren’t dramatic so much as necessary. I ended my lease. I packed everything from my three-bedroom house into storage. I left my city. I bounced between friends and family while trying to keep my nervous system regulated enough to think clearly about what came next. There was no grand plan, only running into a fire with triage.

I’ve talked before about sexism in business and about the way pretty privilege operates as a double-sided sword that people love to oversimplify. Yes, it exists. Yes, it opens doors. But those doors are rarely free, and the cost is seldom acknowledged by people who benefit from pretending the tradeoff isn’t real. When things are handed to you because of how you look, they come with strings attached—expectations embedded, assumptions baked in. You’re expected to be easier. More agreeable. Less complicated. Your competence is often treated as optional, your struggles as unlikely, your boundaries as negotiable. There’s an unspoken belief that attractiveness should insulate you from hardship, that if life is generous with your exterior, you have no right to be messy, exhausted, or affected. Emotions soon become inconvenient. And when you fail to live up to that projection, when you have real problems, real limits, real consequences, you are met not with empathy, but with confusion and resentment. That kind of distortion can be isolating and dangerous. And it can make you profoundly lonely in ways that’s hard to translate unless you’ve lived inside the contradiction of being both highly visible and fundamentally misunderstood.

At the same time, I don’t want this season to live entirely in that space. What matters now is that I’ve found my way back to my creative self— not in a nostalgic way, but in an honest one. Creativity was never something I discovered later in life. It was always there, even from the beginning. As a kid, I won awards for my drawings, and my teachers encouraged me to write history essays as poems instead of forcing them into MLA format. Creativity wasn’t extracurricular for me; it was my natural state.

That instinct eventually took me into fashion. I modeled and worked with small brands and magazines. I loved it, but the industry was brutally narrow then. I’m petite by fashion standards, and even when I lied about my height (somehow managed to sell the fib that I was 5’8” and not 5’6” to my agent), it still wasn’t enough. Mind you, this was before body inclusivity, before flexibility, before any meaningful conversation about expanding what was allowed in the modeling and fashion industry. About 90% of casting rooms were closed to me before I ever walked in, even with my lie of two inches (that’s what he said).

I was emancipated from my parents and went to college early. By eighteen, I transferred to George Mason University and took out a forty-thousand-dollar loan to pay for one year of school. One year. I never really wanted to go to college, and I still believe that if you’re not sticking a needle in someone, you probably don’t need a piece of paper to prove you’re capable. That’s my personal belief. But I also understood the system well enough to use it strategically.

I looked at my modeling paychecks. I looked at the business world and its long-term potential. Then I looked at my own position— what I had access to, and what I didn’t. I had a Minnesota public education. I was advanced, sure, but I was on my own, and I understood that very early.

So I made a decision. I chose a school strategically, based on proximity to power and connections, not prestige. I got an internship, turned it into a job, and didn’t look back.

When I transferred to George Mason, the contrast became unavoidable. Suddenly, I was surrounded by peers who came from oil money, elite private schools, and dinner tables stacked with mentors and inherited access. Their backpacks were Birkins. Their cars were Lamborghinis in rotating colors. That was the moment I could see, in real time, what I was actually competing against, and how differently we had all been resourced.

I started in marketing and haven’t held a marketing title since. I’ve been C-suite adjacent or above, and that climb required edits. I deleted social media. I asked magazines and brands to take down my name in their campaigns. I curated my image carefully because I needed to survive in business spaces that do not tolerate complexity in women. It worked, but it also took something out of me.

That’s why I started What Sheridan Said. I have a bad habit of not opening up, of not letting people understand who I actually am, because I spent so much of my life making complicated decisions in environments that didn’t favour honesty. Maybe I am complicated. Maybe I want more than the world is willing to offer. Both things can be true.

What’s new is that I’m happy I am writing again. I’m getting more gigs. I’m working on scripts, a play, and a short film— my own short film! I have my team and my crew lined up, and I’m excited to refine my craft without it feeling conditional.

I do want to mention something, because people can misread me: But I hope you know, when I’m arrogant, it’s comedy. It’s actually my armor. If I’m being cocky, it’s usually because I don’t feel confident at all, and I’m turning that discomfort into humor before it has a chance to swallow me whole.

“Sheridan the Great” is a bit, but it’s also a wish. Part humor, part manifestation, part self-defense. I know what I carry. I know the walls I built to survive my business career. I know what changed when I moved to D.C. and saw power up close, every version of it, every sin, every corruption I wasn’t prepared for. That kind of exposure changes you, whether you want it to or not. Calling myself great isn’t a claim; it’s my way of hoping, a way of reminding myself that I have greatness within.

Last week, I was working nonstop on set, and when I got home with twenty minutes to spare before I normally write and publish, I didn’t have it in me. I write close to posting because I want these episodes to reflect my actual week, not a sanitized version of it. If I had written that night, it would have been a raw rant about how overwhelmed, exhausted, and emotionally spent I was. That didn’t feel useful or honest in the way I want this space to be.

So I didn’t write. Not because I didn’t care. Not because I was avoiding you. Sometimes, restraint is the more responsible choice. You don’t need every spiral in real time; you just need to know that I’m still here.

This past year, last season, has been about ripping off every possible Band-Aid. Writing to you every Wednesday has been such an incredible part of that. I know I contradict myself. I know things don’t resolve neatly. But I’m committed to staying in the process instead of pretending I’ve already arrived.

There’s also a lot happening practically. I’m putting season one together as a digital and printed book, likely hardcover, with an accompanying voiceover so you can listen to me rant on the go. I’m solidifying the location for my short film, about twenty minutes long, which is small by industry standards, but enormous to me. For most of my career, my success was measured by how well I made other people successful. This is different; this is me applying everything I’ve learned to my own work.

So here we are, Episode one of Season two. Definitely not a clean reset, but a continuation with sharper awareness. I’m still dramatizing my life, because frankly, it entertains me, and I might as well let it entertain you, too. But this season, this year, I’m doing it with clearer boundaries, steadier hands, and a deeper commitment to telling the truth as I actually experience it.

And that feels like the right place to begin again.

xo,
Sheridan Guerrette
WhatSheridanSaid.com
Life Behind the Artist: Wed at 9/8C