On Your Terms®

What if the thing holding your business back is you doing too much?

Going into this year, I planned an “entrepreneur gap year” with no big launches, no book, and less pressure. Instead, I took 30+ flights, crashed and burned by summer, hurt my foot playing tennis, and stepped away from content almost entirely. And my business didn’t slow down. Leads kept coming in, sales kept happening, and I’m now having my highest-revenue year ever.

In this cozy, behind-the-scenes episode, I’m sharing what I cut, why I think it worked, and the honest part I’m s...

You could post the best Instagram post of your life and hardly anybody would see it. Meanwhile, I have more than 74,000 people on my email list, which is way more than whoever follows me on social media. And that’s not an accident.

When my parents died within the same year, I didn’t have the capacity to be on social media. So I went all in on my email list, and it became the life raft that kept my business afloat. In this episode, recorded from Kit Studios in NYC, I’m sharing exactly what’s growing...

You have an offer you want to sell. Maybe you’ve even sold a bit of it already. But do you really understand why people buy it? Or are you playing by feel?

Most business owners market their offers using the language they use in everyday life, or whatever sounded good to a few friends and family members. The problem is that your customers don’t talk like you. And if you don’t know what’s actually making them click purchase, you’re wasting a lot of time on marketing that doesn’t work.

For the 300t...

Maybe you’re about to start your online business and want to do it right from day one. Or maybe you’ve been at it for a while and, if you’re honest, your business is held together with duct tape, string, hope, and a prayer. Either way, you want the same thing: your legal ducks in a row, so you can stop wondering if you missed something and finally put yourself out there with confidence.

The problem is you don’t know what you don’t know. So in today’s episode, I’m giving you my entire free...

Maybe you’re about to start your online business and want to do it right from day one. Or maybe you’ve been at it for a while and, if you’re honest, your business is held together with duct tape, string, hope, and a prayer. Either way, you want the same thing: your legal ducks in a row, so you can stop wondering if you missed something and finally put yourself out there with confidence.

The problem is you don’t know what you don’t know. So in today’s episode, I’m giving you my entire free...

Is the legal side of your business handled? Or is it still sitting on your "I'll deal with it later" list?

Maybe you're about to start your online business and you want to do it right from day one. Or maybe you've been at it a while and you have a feeling you skipped a few legal steps. Either way, you want your ducks in a row before you take even one more dollar online.

I get it. The legal stuff is overwhelming, and most people don't know where to start or what order to...

Daydreaming about life outside your nine-to-five? Wondering if your side hustle could become your full-time thing, but not sure when to actually leave?

In this episode, I'm sharing how I knew it was time to leave my corporate law career, the financial and logistical steps I'd have in place before you give notice, and the emotional prep nobody talks about. Because being miserable at your job isn't a sign you're ready to leave. It's a sign to start getting ready.

Plus, the turbulent plane ride that finally made me say "I'm done," and the weekend...

I've sold over $10M in digital products online, and right now three things in our industry have my attention: protecting yourself from AI and the AI label changes coming, protecting your personal privacy as a creator, and the wave of ADA lawsuits hitting online business owners.

The live class has passed but you can take my free legal workshop "5 Steps to Legally Protect & Grow Your Online Business" any time. Grab your spot here

In this episode, you'll hear…

What happens when you get invited to an author mastermind with James Clear, Mark Manson, and Gretchen Rubin? You say yes, then spend days wondering if they sent the email to the wrong person.

I'm taking you inside James Clear and Nathan Barry's mastermind at Kit Studios in NYC. I'm sharing the best tactical tips I picked up from people who've sold tens of millions of books: the two-slide Instagram Stories trick that skyrockets engagement, what makes a quiz lead magnet actually convert, a genius way to turn nice DMs into public reviews, and the one thing...

If you started your business today, would you actually follow your own old advice? I wouldn't. And after over $9 million in sales, I'm telling you exactly why.

This isn't the first time I've tackled this topic either. Back in episode 28 (2022) and episode 186 (2024), I talked about what I'd do differently if I started over. Some of that advice still holds up. A lot of it doesn't anymore. So today I'm setting the record straight on what I'd keep, what I'd completely reverse, and what I think matters most for online business owners heading into 2026 and beyond.

...

My gap year was supposed to be boring. Instead I've taken 19 flights before summer even ended, and somehow I still feel more rested than I have in years.

This episode is part of my summer read-aloud series, where I'm sharing personal essays straight from my Substack. This one's about what happened when the "spacious, do-nothing" gap year I planned turned into a calendar full of tennis lessons, swim classes, and last-minute flights, and why I had to stop judging myself for it.

In this episode, you'll hear…

I got forced to slow down, and it's the lesson I need to learn over and over again.

In this episode, I read a personal essay from my Substack about a tennis injury that took me out mid swing. One minute I'm making an incredible shot down the line, the next I'm on the ground with my knee twisted and my foot throbbing.

But this episode isn't really about the injury. It's about what happens when your body forces you to stop, and what that stillness makes you face, including grief I've been carrying since...

Have you ever had a moment so small (a bird, of all things) crack open something so much bigger about how you're living your life?

This week's episode is part of my summer series where I'm reading personal essays straight from my Substack. This one's about a very ornery bird I met on a hike in Patagonia, the bird I accidentally trapped in my bedroom when I was 10 (yes, really), and how a string of small, strange bird encounters slowly nudged me toward paying more attention to the world right in front of me.

If...

We've lost the plot when it comes to creating content. In this week's summer read-aloud, I share a personal essay on how my own productivity systems, batching, optimizing, and keeping up with an AI fueled content arms race, ended up killing my creativity.

So kick back, pop in your headphones, maybe go for a walk, and let's talk about why being productive and being creative aren't always the same thing.

In this episode, you'll hear…

What happens when you give yourself an entire year off and can't actually take it? That's the question I'm sitting with in this week's essay. I declared 2026 my entrepreneurial gap year. I did not stay off.

Instead of a regular episode this week, I'm reading you this essay straight from my Substack, the place where I write about grief, overconsumption, overworking, and learning to actually be present in my life.

My full slate of regular On Your Terms® episodes will be back on September 14th, but until then, here's the honest, slightly humbling truth about w...

I recently stood in a long line for pancakes I wasn't even sure I wanted. And it made me realize how much of what I consume, eat, buy, watch, isn't actually chosen by me anymore. It's chosen by whoever posted about it first.

This summer, I'm taking a little break from our regular episodes so I can rest, recharge, and come back to you on September 14th with a full slate of new content. In the meantime, I'm sharing a few of my favorite essays from my Substack, Sam Vander Wielen, right here on the podcast. Today's...

One of the strange gifts of your life completely burning to the ground is the fertile soil it leaves behind for you to begin again. That's where I found myself after losing both of my parents in the same year, recovering from brain surgery, and realizing that being "extremely online" wasn't actually serving me or my business.

This week I'm continuing my summer series, where I'm reading you essays straight from my Substack while I take a little break before we're back with full-force episodes on September 14th. This one's about the health, digital wellness, and business...

Everyone's obsessed with the getting off social media part — deleting the apps, doing the digital detox, bragging about their screen time going down. But almost no one talks about what's supposed to happen once you actually log off. Because here's the thing: stepping away from Instagram only to fall into a Substack doom scroll isn't really progress. It's just a softer-feeling version of the same problem.

In this episode, I'm doing something a little different to celebrate summer — I'm reading you one of my recent essays straight from my free Substack, where I get real about what it's...

I'm taking a little summer break, not just from the podcast, but from working in general. And yes, my friends are already cackling about that one, because as my friend Steve put it, he can't wait to watch me be the most productive person he knows this summer. Fair.

So in this episode, I'm pulling back the curtain on what a summer break actually looks like for a business owner. What I'm doing, what I'm not doing, and the honest truth about whether you're ever really "off" when your name, face, and voice are all over your...

If you've ever wondered what it's actually like to attend one of the best conferences in the online business space, I'm bringing you along this week. Every June, I pack my bags for Boise, Idaho to attend Kit's Craft + Commerce Conference, and this year I recorded real-time clips along the way so it would feel like we were just hanging out in the hallway together.

This is officially my fifth Craft + Commerce, and in this episode I'm sharing my full recap: why I keep going back, what my week actually looked like behind the scenes, the tactical...

“Must be nice.” It sounds harmless. Like a throwaway comment, a passing thought, something you mutter when you see someone doing something you wish you could do. But I’ve been thinking about this a lot lately, and I think that little phrase is one of the most dangerous things you can say to yourself as a business owner.

Because here’s what it’s actually doing: it’s letting you off the hook. It’s a quiet way of deciding something doesn’t apply to you before you’ve even given yourself the chance to find out if it could. A...

Everyone keeps coming up to me like they're attending my business's funeral. "How are things?" And I'm standing there like... everything's actually great? My business keeps growing. But I get it. There's no shortage of people online saying digital products are dead, courses are dead, the whole thing is over.

Here's the thing: the market has changed. A lot. And if you have a digital product or course, you've probably felt it. Buyers are taking longer to make decisions, coming in with their guard up, asking more questions. But "harder" is not the same as "dead." After 10...

You know reels are one of the best ways to grow your business on Instagram. You've seen other people crushing it. You've probably even sat down to film one yourself, maybe more than once, and then... you just didn't post it. Or you did, and it flopped, and somewhere along the way, the whole thing started to feel way more complicated than it's worth.

Here's what I actually think is happening: you're drowning in advice that was designed for influencers, not for people who run a real business. Hook formulas, trending audio, CapCut tutorials, edit transitions... it...

Every entrepreneurship influencer on the internet has an opinion about what you should be doing. Six AM wake-ups. A content calendar mapped out six months in advance. Tracking every metric. Showing up on every platform all at once. But here's the thing — what successful founders say they do and what they actually do behind the scenes? Often very, very different.

I know because I'm one of those founders. And when people meet me in real life, the thing they always say is, "Wait, your business is so chill and simple. You don't do any of the stuff pe...

I recently apologized to my shower handle.

No, really. I turned off the water before rinsing out my conditioner, reached back to flip it on again, and instinctively said sorry to a cold, metal, completely inanimate faucet. And that moment stopped me dead in my tracks, because if I'm apologizing to shower handles, what else am I unnecessarily apologizing for in my life and business?

This episode is a little different. I'm reading you an essay I originally published on my Substack, Beyond Business, because I genuinely believe so many of you need to hear...

You're busy. You're building. You're making a thousand decisions a day — what to post, what to buy, what to eat, what to cut. And somewhere along the way, all of that choosing started to feel like its own full-time job.

Here's the thing: we've been sold this idea that more optimization equals more freedom. That if you just find the perfect system, the perfect routine, the perfect answer, you'll finally be able to relax. So you keep researching and refining and second-guessing. And the relaxing never actually comes.

This episode is about what happens when yo...

What if stepping back from social media was actually the thing that made it work better for your business?

I'll be honest with you: my relationship with social media has been a lot. It helped me build a multi seven-figure business. Then it became my number one addiction. Then it turned into a coping mechanism I reached for every time life got hard. And then, after losing both of my parents, I basically wanted to throw my phone into the ocean and never look back.

In this episode, I'm sharing the full, messy truth of...

Have you ever wondered why people in your audience don't think of you when they're ready to buy — even though you've been showing up, creating content, and putting offers out?

Here's the hard truth: it's probably not your audience size. It's not your content. It's not even your offer. The real problem is that nobody knows what to associate your name with. And the good news? That is a very fixable problem.

In this episode, I'm diving into why so many online business owners stay invisible — and what it actually takes to become the "McFlurry" of y...

I just got back from three days in Atlanta with some of the most impressive people in the online business space, and I am still processing all of it.

We're talking New York Times bestselling authors, YouTubers with millions of subscribers, book agents and editors, SaaS founders, and high-level consultants serving Fortune 100 companies. All 40 of us crammed into rooms, hot seats, and late-night fire pit hangs for what turned into one of the most valuable professional (and personal) experiences I've had in years.

I walked away with pages of notes on pricing psychology, LinkedIn strategy...

You've watched other people's launches from the sidelines. The big revenue numbers, the sold-out offers, the "We Hit Our Goal in 24 Hours" Instagram stories. You want that too. And so you try. You do all the launch things. But something's off. The sales trickle in slower than you hoped, or it's just... crickets. And you start wondering if it's your emails, your offer, your timing, or honestly, if it's just you.

Here's the truth: it's probably none of those things.

The real issue is happening way before launch week ever starts. In this episode, I'm...

Automation is great — until it makes people forget there's a real human behind your business. In this episode, I'm pulling back the curtain on the tool I've been quietly using to generate content ideas, boost webinar show-up rates, and collect testimonials, all while making my audience feel personally connected to me. It contributed to a $500K launch, and I'm walking you through exactly how I use it for content, sales, and social proof.

In this episode, you'll hear…

If you've ever opened a blank document to write your newsletter and immediately closed it again, this one's for you.

I've been sending my weekly newsletter, Sam's Sidebar, consistently for years, and in this episode, I'm pulling back the curtain on exactly how I decide what to write every single week. Including the time I scrapped a completely finished email the morning it was supposed to go out, wrote something raw and real in about five minutes, and watched my inbox light up with replies all day long.

This is the behind-the-scenes process I use...

Q1 is officially in the books — so before you barrel headfirst into Q2, let's actually stop and take stock of how it went.

In this episode, I'm walking you through the end-of-quarter check-in I use in my own business — one that covers both your stats and your vibes — so you can go into the next quarter with one clear focus, a simple plan, and a lot less "why does running this business feel so chaotic?" energy.

We'll talk about how to look at your numbers without spiraling into a shame spiral, how to figure out whethe...

Sam pulls back the curtain on her biggest launch ever — $500K in revenue in just four days. She's sharing the real numbers: 11,000 webinar registrants, a 5% conversion rate, and exactly what she spent on ads to get there. But this isn't just a brag fest — Sam gets honest about what's actually behind a launch like this, why you can't just copy someone else's formula, and what entrepreneurs at every stage can take away and apply to their own business.

Whether you're planning your first launch or looking to scale, this episode is packed with practical strategy on webinars, emai...

Everyone's talking about Substack — and maybe you're curious, a little skeptical, and 100% wondering if you actually need to add another platform to your already-full plate. (Spoiler: you don't need to. But you might want to after this.)

In this episode, I'm pulling back the curtain on exactly how I grew my Substack, Beyond Business, to 1,000 subscribers using only organic strategies — no importing my 60,000+ person email list, no fancy custom design, no team of people building it out for me. Just consistent writing, a growth mindset, and a few simple (but powerful) tactics I wish I'd known earlier.

If you’re trying to grow your audience for your online business, you’ve probably heard advice like “build the audience first” or “you need followers before you can launch.” But what if that’s backwards?

In this episode of On Your Terms®, Sam shares the real foundation of sustainable audience growth—and why focusing on followers, email list size, or social media metrics too early can actually slow you down. Instead, she breaks down how mastering your craft (whether that’s writing, podcasting, video, or your core service) is what truly builds an audience that sticks.

You’ll hear…<...

Have you ever heard a quote at exactly the moment you needed it? Like it practically reached out and grabbed you by the shoulders?

That happened to me recently when I heard this line from The Artist’s Way: "perfectionism isn’t a quest for the best… it’s a pursuit of the worst in ourselves.

Oof. Holy cannoli. That one knocked me flat.

In this episode, I’m sharing the simple exercise that helped me see my burnout in black and white—and how you can use it to finally exhale.

You’ll hea...

If you’re building a business, doing “all the right things,” and still feel exhausted even after a full night of sleep… this episode is for you.

So many entrepreneurs think rest is something you earn later — after the launch, after the revenue goal, after things finally feel “stable.” And that belief keeps you stuck in a cycle of pushing, white-knuckling, and wondering why you’re burned out even though you technically love your work.

I’m breaking down the 6 different types of rest, why sleep alone won’t fix burnout, and how I’ve been intentionally wea...

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...

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 no...