On Your Terms®

It’s mid-February (or honestly… March… or April… or whenever you’re listening), and if your New Year’s goals already feel like they’ve floated off into the abyss — you’re not broken. You’re just human.

In this episode, I’m breaking down why January 1st is kind of a terrible time to set goals, especially if you’ve been navigating grief, uncertainty, burnout, or just… life. I’m sharing how I actually set goals now using a monthly goals method that’s way more realistic, flexible, and supportive — and yes, you’re absolutely allowed to steal it.

In this episode, you’ll hear…

1. Why January 1st isn’t actually a clean slate (and never has been)
2. How grief, uncertainty, and burnout affect goal-setting more than we admit
3. The monthly goals method I use instead of New Year’s resolutions
4. How to set goals when you don’t feel clear or motivated
5. Ways to bring “new year energy” into any month of the year
6. How to stay present and profitable without rigid long-term plans

Click here to find the full show notes and transcript for this episode.

RESOURCES:

• Leslie Stephens' Substack Note
• Listen to EP 274. 4 Tiny Shifts I Make Every Winter (so I feel cozy, not crushed)
• Listen to EP 251. How To Leave Social Media without Losing Your Clients
• Click here to be notified when new episodes of On Your Terms® come out

CONNECT:

• Get Sam's weekly newsletter, Sam's Sidebar
• Follow Sam on Instagram
• Follow Sam on YouTube
• Subscribe to Sam's Substack, Beyond Business
• Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"
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DISCLAIMER

There’s this moment in business where you keep thinking, okay… when does it get easier? When does the stress chill out, the money feel steadier, and you finally get to enjoy what you’re building?

Here’s the sneaky truth I wish someone had told me sooner: the “someday” version of your life isn’t where the joy starts. The rise is actually the fun part.

In this episode, I’m sitting down with the version of myself from five years ago (hello, 2021 Sam) and sharing the six lessons I wish I could’ve handed her in a note. These aren’t fluffy business platitudes — they’re the real, lived-in truths that only come from building a seven-figure business, navigating massive personal loss, and realizing the mountaintop doesn’t feel the way everyone promises it will

In this episode, you’ll hear…

• Why the rise is actually the best part (even when it feels messy)
• The hard truth about the “carrot” always moving in business
• How chasing someone else’s version of success can quietly wreck your joy
• Why you don’t need to be “one of them” to build a wildly successful business
• How to stay confident being a leader — especially when new platforms and trends pop up
• The simple mindset shift that helped me finally loosen my grip on control

Click here to find the full show notes and transcript for this episode.

RESOURCES:

• Get Sam’s free weekly newsletter, Sam’s Sidebar
• Get Sam's book "When I Start My Business, I'll Be Happy"
• Click here to be notified when new episodes of On Your Terms® come out
• Click here to watch the free workshop so you can get legally protected right now!

CONNECT:

• Get Sam's weekly newsletter, Sam's Sidebar
• Follow Sam on Instagram
• Follow Sam on YouTube
• Subscribe to Sam's Substack, Beyond Business
• Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER

In this episode, you get to hear my full live training, “How To Legally Protect & Grow Your Online Business in 2026.” I’ll give you the five steps every entrepreneur needs to take. We’ll cover shifting your mindset, registering as the right business entity, protecting yourself in case of a lawsuit, getting your contracts and policies in place, and staying within your scope of practice.

Whether you’re a coach, course creator, service provider, or product-based entrepreneur, I’m walking you through the five simple legal steps you must take to set up your business, protect your content, and get paid confidently.

No law degree (or stress spiral) required.

In this episode, you’ll hear…

• 5 things you must have in place before accepting even $1 (more) online
• Exact steps to form your business
• Should you become an LLC or sole prop? 
• Why you NEED to have business insurance (it’s so worth it)
• An actual method for figuring out what you can (and cannot) do online or when you’re NOT working under your professional license

RESOURCES:

• The Ultimate Bundle® is on sale through February 13th.

CONNECT:

1. Sam on Instagram
2. Sam on Facebook
3. On Your Terms® on Instagram

DISCLAIMER

When it gets dark before you’ve even wrapped up work for the day, winter can feel like it shrinks your whole life. Suddenly everything feels harder, heavier, and honestly… a little bleak. And while part of you might want to hibernate until April, another part of you knows that doesn’t really work when you’re running a business and trying to live a full life.

In this episode, I’m sharing how I’ve learned to actually work with winter instead of fighting it. After moving from Philly to the north shore of Long Island (where winter is colder, darker, windier, and somehow five degrees colder just to be rude), I had to build a real winter toolkit — not just cozy socks, but mindset shifts, routines, and intentional rituals that make this season feel supportive instead of soul-crushing.

In this episode, you’ll hear…

• Why your relationship with winter might be making it harder than it needs to be
• The mindset shift that completely changed how I experience winter
• How I intentionally design winter to feel cozy, grounding, and even enjoyable
• Why winter is actually essential for creativity, energy, and long-term sustainability
• Simple routines and rituals that give you something to look forward to all season long

Click here to find the full show notes and transcript for this episode.

RESOURCES:

• Get Sam’s free weekly newsletter, Sam’s Sidebar
• Learn about The Ultimate Bundle® on Sale
• Get Sam's book "When I Start My Business, I'll Be Happy"
• Click here to be notified when new episodes of On Your Terms® come out

CONNECT:

• Get Sam's weekly newsletter, Sam's Sidebar
• Follow Sam on Instagram
• Follow Sam on YouTube
• Subscribe to Sam's Substack, Beyond Business
• Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER

Re-shooting all the videos for a product that’s generated over $8 million sounds like a straightforward business upgrade… until it isn’t.

In this episode, I’m taking you behind the scenes of what it was really like to re-record every single video inside the Ultimate Bundle®. Spoiler alert: this was about way more than lighting, scripts, or batch recording. It cracked open a lot for me — about grief, seasons of business, fear of slowing down, and the pressure we put on ourselves to constantly “improve” things that are already working.

If you’ve ever felt overwhelmed by a big project, nostalgic for earlier seasons of your business, or quietly scared of what might happen if you let yourself rest, this episode is for you.

In this episode, you’ll hear…

• Why re-shooting the Ultimate Bundle® felt more like reliving the bar exam than a simple content update
• What building an MVP actually looks like over eight years of growth
• The hidden cost of having a wildly successful signature product
• How grief, loss, and survival mode quietly shaped my business from 2020 on
• Why “easy” seasons of business can feel surprisingly uncomfortable
• What early-stage hustle teaches you that success sometimes takes away
• How I approached updating a proven product without burning it all down

Click here to find the full show notes and transcript for this episode.

RESOURCES:

• Get Sam’s free weekly newsletter, Sam’s Sidebar
• Get Sam's book "When I Start My Business, I'll Be Happy"
• Kit :what I use to build my email list, send emails to my list, and create opt-in forms & pages (affiliate link)
• Register for my free LIVE legal training “5 Steps to Legally Protect & Grow Your Online Business in 2026”
• Click here to be notified when new episodes of On Your Terms® come out

CONNECT:

CONNECT:

• Get Sam's weekly newsletter, Sam's Sidebar
• Follow Sam on Instagram
• Follow Sam on YouTube
• Subscribe to Sam's Substack, Beyond Business
• Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER

We all know that moment. It’s Sunday. Your phone buzzes. And suddenly you’re staring down your weekly screen time report wondering… how did THAT happen?

For me, those little reports started to feel like a mirror I didn’t really want to look into. The number on the screen didn’t line up with the life I said I wanted to be living—more present, less irritable, doing deeper work, and actually enjoying my days instead of scrolling through them.

So I decided to stop ignoring it and actually take my screen time seriously. In this episode, I’m sharing what happened when I did just that—for 30 days.

This isn’t about deleting every app or pretending your phone isn’t a major part of your business (because let’s be real… it is). It’s about creating a healthier relationship with your phone so it can be a tool instead of an appendage—and building a business that doesn’t require you to be glued to it 24/7.

If you want to be more present in your life and more profitable in your business, this episode is for you.

In this episode, you’ll hear…

• Why your screen time report can reveal way more about your life than you think
• How I reduced my screen time without shame, guilt, or extreme rules
• The difference between “productive” screen time and the kind that quietly drains you
• The app that consistently sends me into a doom-scrolling spiral (and what I do about it)
• How to find your personal tipping point with screen time—without comparing yourself to anyone else

Click here to find the full show notes and transcript for this episode.

RESOURCES:

• Get Sam’s free weekly newsletter, Sam’s Sidebar
• Subscribe to Sam's Substack Beyond Business
• Get Sam's book "When I Start My Business, I'll Be Happy"
• Click here to be notified when new episodes of On Your Terms® come out

CONNECT:

• Get Sam's weekly newsletter, Sam's Sidebar
• Follow Sam on Instagram
• Follow Sam on YouTube
• Subscribe to Sam's Substack, Beyond Business
• Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER

If you’ve been side-eyeing Substack trying to figure out whether you should start one, what you’d even put on it, or how it’s different from your “regular” newsletter… this episode is your permission slip to breathe. Because guess what? I’ve been figuring this out in real time too — and today, I’m breaking down exactly how I’m using both Substack and my newsletter, why I treat them differently, and how YOU can create a simple, sustainable content structure that actually supports your business.

I’ll also walk you through the discovery → nurture → conversion framework I use to decide which platforms get my energy — and which ones simply get a presence without becoming a second job. Because you are absolutely not meant to create cornerstone content for 19 platforms. No thank you.

Whether you’re Substack-curious, newsletter-confused, or trying to design a content flow that doesn’t make you want to run away to a cabin in the woods, this episode will give you clarity.

In this episode, you’ll hear…

1. How I’m using Substack differently from my weekly business newsletter
2. Why your content should flow from one or two core platforms (not all of them)
3. The discovery–nurture–conversion method I use to understand where each platform fits
4. How I’m thinking about Substack as an experiment (and why that’s OK!)
5. What goes on Substack vs. what stays in my main newsletter
6. How to decide where YOUR content belongs without overthinking it

Click here to find the full show notes and transcript for this episode.

RESOURCES:

1. Get Sam’s free weekly newsletter, Sam’s Sidebar
2. Subscribe to Sam's Substack Beyond Business
3. Get Sam's book "When I Start My Business, I'll Be Happy"
4. Listen to Sam on Cubicle to CEO Episode 293. 46k List Growth Case Study: From Snooze-Worthy To Subscriber Magnet
5. Writing a Book Podcast Playlist
6. Kit - what I use to build my email list, send emails to my list, and create opt-in forms & pages (affiliate link)
7. Click here to be notified when new episodes of On Your Terms® come out
8. Click here to watch the free workshop so you can get legally protected right now!

CONNECT:

1. Get Sam's weekly newsletter, Sam's Sidebar
2. Follow Sam on Instagram
3. Follow Sam on YouTube
4. Subscribe to Sam's Substack, Beyond Business
5. Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"
6. DISCLAIMER

DISCLAIMER

Let’s talk about the thing I didn’t even realize was happening until it had already messed with my head: AI was quietly killing my creativity.

If you’ve ever opened your laptop, told yourself you’re “just getting a little AI help,” and then suddenly noticed your ideas feel watered down, your content feels off, and you’re second-guessing everything—you’re not alone. When I posted about this on Instagram, you confirmed that this little creep has been slipping into your business too… and not in the cute, helpful way we hoped.

So today, I’m getting brutally honest about how AI slowly started impacting my creativity, confidence, workflow, and even the way I approached this podcast. This episode is your reminder that your most valuable business asset is your brain—your original ideas—not a robot’s outline telling you how you should create.

In this episode, you’ll hear…

1. How AI slowly crept into my creative process without me realizing it
2. The dangerous shift from “this helps” → “this must know better than me”
3. How AI’s feedback made me doubt my instincts and dry up my idea well
4. The moment I realized AI was contributing to a huge creativity block
5. What happened when I quit using AI for outlines, brainstorming, and feedback
6. The difference between using AI as a repurposing tool vs. as a creator
7. The creative habits and practices I’m returning to in 2026
8. How to rebuild your originality in a world obsessed with shortcuts

Click here to find the full show notes and transcript for this episode.

RESOURCES:

1. Get Sam’s free weekly newsletter, Sam’s Sidebar
2. Subscribe to Sam's Substack Beyond Business
3. Get Sam's book "When I Start My Business, I'll Be Happy"
4. My Instagram Reel on quitting ChatGPT
5. Listen to Episode 140. We Need To Talk About Dupe Culture
6. Meet Your AI All Stars Course (affiliate link)
7. Grab the Ultimate Bundle®
8. Click here to be notified when new episodes of On Your Terms® come out
9. Click here to watch the free workshop so you can get legally protected right now!

CONNECT:

1. Get Sam's weekly newsletter, Sam's Sidebar
2. Follow Sam on Instagram
3. Follow Sam on YouTube
4. Subscribe to Sam's Substack, Beyond Business
5. Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER

You know that feeling when you come back to your desk in January and everything is a disaster? Your desktop looks like a digital garage sale, your office chair is still wearing yesterday’s sweater, and your brain feels like it’s running 42 tabs at once?

Yeah… we’re not doing that this year.

In this episode, I’m sharing the super simple, totally doable tasks I’m doing in the next two weeks—while cozied up in my pjs —to close out 2025 in a way that feels calm, grounded, and actually restorative. No “new year, new hustle” energy required. Just a cleaner home base, a quieter mind, and a business you can step back into without the chaos hangover.

This is your permission slip to put the laptop away, clean the slate, and give your future self a January that feels good.

In this episode, you’ll hear…

1. The 4 things I always do to wrap up my business before the holidays
2. Why I deep clean everything (yes, including the dreaded office drawer) before taking time off
3. How I’m approaching 2026 as a “mental gap year”
4. My end-of-year digital detox ritual
5. What I’m doing during my time off to reconnect with creativity
6. The cozy winter habits keeping me sane in an extremely dark, extremely windy Long Island winter

Click here to find the full show notes and transcript for this episode.

RESOURCES:

1. Get Sam’s free weekly newsletter, Sam’s Sidebar
2. Get Sam's book "When I Start My Business, I'll Be Happy"
3. Listen Episode 267: Before You Plan 2026, do THIS first
4. Listen to Episode 268: How to Create Your Ideal Business Year (Without Burnout-y Goals)
5. Grab the Ultimate Bundle® and use code OYTWRITEOFF to save 20% off through December 18th.
6. Read Sam's Substack Taking a Gap Year as an Entrepreneur: My Year of Letting Go in 2026
7. Click here to be notified when new episodes of On Your Terms® come out
8. Click here to watch the free workshop so you can get legally protected right now!

CONNECT:

1. Get Sam's weekly newsletter, Sam's Sidebar
2. Follow Sam on Instagram
3. Follow Sam on YouTube
4. Subscribe to Sam's Substack, Beyond Business
5. Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER

It’s that time of year again — when everyone online suddenly becomes a color-coded-notion-board-wielding planning expert. But before you map out your entire 2026 vision board, we need to do something way more important: figure out what you actually want.

In today’s episode, I’m walking you through the exact reflection + annual planning exercise I do every single year — the one that helps me make decisions based on how I want to feel, not what the latest marketing trend says I “should” be doing. This episode pairs with last week’s 2025 reflection episode, so if you haven’t listened to that one yet, go queue it up next.

PLUS — I’m trying something new today. I pulled a random question from the “More, Tell Me More” connection cards I won at a mastermind retreat (yes, I was voted Best Strategy at my table and the whole room — no biggie). I answered it… and I want you to answer it too. If you love this segment, email me or DM me and tell me to keep it!

And before you dive in, don’t forget: I created a free 2026 Annual Planning Guide that includes every question I ask in this episode and space for you to jot down your reflections and goals. Grab it in the show notes!

In this episode, you’ll hear…

1. The connection-card question I pulled — and the unforgettable story about the stranger who changed how I think about human connection
2. Why planning for 2026 means starting with how you want to feel (not arbitrary goals like “50K followers”)
3. How to imagine your ideal day next year so you can reverse-engineer what needs to change
4. Why so many entrepreneurs felt unstable in 2025 — and how to honor what actually happened before planning ahead
5. The questions I use every year to figure out what I truly need in my business and personal life
6. A guided reflection to set aligned, realistic, energizing goals for 2026

Click here to find the full show notes and transcript for this episode.

RESOURCES:

1. Get Sam’s free weekly newsletter, Sam’s Sidebar
2. Get Sam's book "When I Start My Business, I'll Be Happy"
3. Listen to the How to Grow Your Email List Series Playlist
4. Subscribe to Sam's Substack Beyond Business
5. Download Sam's Annual Planning Guide
6. Click here to be notified when new episodes of On Your Terms® come out
7. Click here to watch the free workshop so you can get legally protected right now!

CONNECT:

1. Get Sam's weekly newsletter, Sam's Sidebar
2. Follow Sam on Instagram
3. Follow Sam on YouTube
4. Subscribe to Sam's Substack, Beyond Business
5. Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER