On Your Terms®

By Sam Vander WielenBusiness Entrepreneurship Marketing

On Your Terms® episodes

October 05298. I Spent a Week with James Clear, Mark Manson, and Gretchen Rubin. Here's What I'm Changing in My Business.
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 about Instagram almost everybody agreed on.
Plus, I get honest about what it feels like to be the smallest one in the room, and why you won't feel like you belong before you're invited in. I also grab Dan Go and Steve Kamb in the hallway to share their biggest takeaways.
👩🏻‍💻 REGISTER FOR MY FREE LIVE LEGAL CLASS --> https://www.samvanderwielen.com/live-legal-workshop (Replay included!)
In this episode, you'll hear…
How a decade of tiny, unglamorous decisions landed me at a mastermind with James Clear, Mark Manson, and Gretchen Rubin
What makes a quiz lead magnet actually work, and why treating your results page like a "hostage situation" is costing you subscribers
A genius (and totally free) way to turn nice DMs and emails into public reviews and testimonials
What it's really like to be the smallest one in the room, and why you won't feel like you belong before you're invited in
Hallway chats with health coach Dan Go and Nerd Fitness founder Steve Kamb about fighting for your own art and doing things your way

Click here to find the full show notes and transcript for this episode.
EPISODE RESOURCES:
Save your seat for the FREE last live legal workshop of 2026, How to Start an Online Business Legally Before 2026 Ends, on Monday, October 19th (Replay included!)
Sam's book, When I Start My Business, I'll Be Happy: A Practical No-BS Guide to Successful Online Entrepreneurship
Check out KIT & get your first month free (affiliate link)
Craft and Commerce recap episode
Sam's previous mastermind recap episode from earlier this year
Dan Go: https://dango.co & Instagram
Steve Kamb: https://stevekamb.com & Instagram
If you have a question you’d like Sam to answer on a future podcast episode, you can submit it here.
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
Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER
1 hr 2 min
September 28297. If I Started My Business Today, I'd Ignore My Own Advice (Here's What $9M Taught Me)
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.
In this episode, you'll hear…
Why I still believe there's no secret formula for building your business (and why copying what's "working" for everyone else can actually box you in)
The one social media strategy I'd keep exactly the same, plus how I use AI tools to repurpose one cornerstone piece of content instead of creating from scratch everywhere
Why I'd ditch a "social media first" approach entirely and build an audience-first business instead
What I wish I'd done sooner when it comes to getting comfortable charging for my content and expertise
How I shifted from "post everywhere, all the time" to focusing on fewer, bigger tasks that actually move my business forward
Why "pace" today means being reactive and in the conversation, not just pumping out volume

Click here to find the full show notes and transcript for this episode.
EPISODE RESOURCES:
👩🏻‍💻 REGISTER FOR MY FREE LIVE LEGAL CLASS --> https://www.samvanderwielen.com/live-legal-workshop
Get Sam's weekly newsletter, Sam's Sidebar
Subscribe to Sam's Substack
Episode 280. How I Got My First 1,000 Subscribers on Substack
If you have a question you’d like Sam to answer on a future podcast episode, you can submit it here.
Click here to be notified when new episodes of On Your Terms® come out

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

DISCLAIMER
32 min
August 31I Planned a Year of Doing Nothing. I Took 19 Flights Instead. [Summer Read-Aloud]
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…
Why I planned a year of "blank space" and ended up busier than ever, just in a totally different way
The real difference between being chronically online and busy versus chronically offline and busy (and why one feels so much better than the other)
What happens to my brain, my relationships, and my sense of reality when I spend too much time online
The moment I realized what I was actually feeling wasn't guilt about overcommitting. It was judgment

Click here to find the full show notes and transcript for this episode.
EPISODE RESOURCES:
Subscribe to Sam's Substack
👩🏻‍💻 REGISTER FOR MY FREE LIVE LEGAL CLASS --> https://www.samvanderwielen.com/live-legal-workshop
Read today's essay My gap year was supposed to be boring
Get Sam's book When I Start My Business, I'll Be Happy
Get Sam's weekly newsletter, Sam's Sidebar
If you have a question you’d like Sam to answer on a future podcast episode, you can submit it here.
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
Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER
13 min
August 24I Built a Multi-Million Dollar Business to Avoid Feeling Anything. [Summer Read-Aloud]
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 losing both of my parents.
In this episode, you'll hear…
The moment I went down mid-shot at a tennis clinic, and the very reaction that followed (spoiler: it involved refusing to stop playing)
Why I instinctively downplayed the injury and tried to keep going, even with blood involved
The connection I draw between forcing my body to heal on it's own timeline

Click here to find the full show notes and transcript for this episode.
EPISODE RESOURCES:
Subscribe to Sam's Substack
👩🏻‍💻 REGISTER FOR MY FREE LIVE LEGAL CLASS --> https://www.samvanderwielen.com/live-legal-workshop
Read today's essay I got forced to slow down
Get Sam's weekly newsletter, Sam's Sidebar
If you have a question you’d like Sam to answer on a future podcast episode, you can submit it here.
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
Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER
9 min
August 17How I Stopped Doomscrolling and Started Watching This. [Summer Read-Aloud]
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 you've been feeling stuck in your phone, disconnected from your neighborhood, or like you're moving through life without really noticing it, this one's for you. It's not really about birds. It's about presence.
In this episode, you'll hear…
The story of the bird who followed me on a brutal hike through the Andean Mountains and seemed to be personally attacking my confidence
What happened when I accidentally let a bird into my childhood bedroom (and what I found six months later)
Why standing somewhere as vast as Patagonia has a way of putting your entire life in perspective
How coming home to Long Island turned into an unexpected obsession with birdwatching
What robins, swans, and bald eagles taught me about noticing the seasons changing, even when I couldn't feel it yet
Why paying attention to the small, local, unglamorous things is what's actually helped me feel rooted and connected, more than anything online ever has

Click here to find the full show notes and transcript for this episode.
EPISODE RESOURCES:
Subscribe to Sam's Substack
👩🏻‍💻 REGISTER FOR MY FREE LIVE LEGAL CLASS --> https://www.samvanderwielen.com/live-legal-workshop
Read today's essay How being attacked by a bird in Patagonia forced me offline
Get Sam's weekly newsletter, Sam's Sidebar
If you have a question you’d like Sam to answer on a future podcast episode, you can submit it here.
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
Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER
11 min
August 10How My Productivity Killed My Creativity [Summer Read-Aloud]
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…
Why I'm running low on content ideas for the first time in a decade, and what that taught me
How my 2026 "gap year" backfired into more batching and pressure instead of the spaciousness I wanted
The real cost of optimizing everything, and why productivity can quietly kill creativity
Why AI is making the content arms race worse, not better
What actually refills my creative well, and why living your life is the best content strategy there is

Click here to find the full show notes and transcript for this episode.
EPISODE RESOURCES:
Subscribe to Sam's Substack
👩🏻‍💻 REGISTER FOR MY FREE LIVE LEGAL CLASS --> https://www.samvanderwielen.com/live-legal-workshop
Read today's essay How my productivity killed my creativity
Get Sam's weekly newsletter, Sam's Sidebar
If you have a question you’d like Sam to answer on a future podcast episode, you can submit it here.
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
Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER
11 min
August 03I Declared a Gap Year. Then I Turned It Into a Full-Time Job. [Summer Read-Aloud]
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 why I can't stop working, and what it's taught me about rest, distraction, and grief.
In this episode, you'll hear…
Why I declared 2026 my entrepreneurial gap year, and how it turned into a full time job anyway
The real reason I keep reaching for my phone, even when I'm trying to unplug
What my brutally honest friend said that made me realize my "time off" looked exactly like work
How grief shows up in the smallest, most random moments, and why distraction feels easier than sitting with it
Why I'm learning to be kinder to myself about the blurry line between resting and being restless

Click here to find the full show notes and transcript for this episode.
EPISODE RESOURCES:
Subscribe to Sam's Substack
👩🏻‍💻 REGISTER FOR MY FREE LIVE LEGAL CLASS --> https://www.samvanderwielen.com/live-legal-workshop
Read today's essay Why I can't stop working (even during my gap year)
Sam's Substack Essay on saying sorry: I'm sorry, but I had to write this
If you have a question you’d like Sam to answer on a future podcast episode, you can submit it here.
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
Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER
10 min
July 27How I Stopped Letting the Algorithm Decide What I Like [Summer Read-Aloud]
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 essay is all about a day I spent in New York City trying to unlearn the habit of letting algorithms and influencers decide what I like, and how I'm working to reclaim my own taste instead.
In this episode, you'll hear…
The pancake line that made me question everything about how I make decisions
Why I think over 80% of Instagram-hyped restaurants aren't even worth the hype
What my no-buy Amazon year has taught me about slowing down and shopping with intention
The conversations with local shop owners that ended up meaning more than any five-star review
How I'm working to reclaim my own preferences, both in New York City and in my everyday life

Click here to find the full show notes and transcript for this episode.
EPISODE RESOURCES:
Get Sam's weekly newsletter, Sam's Sidebar
👩🏻‍💻 REGISTER FOR MY FREE LIVE LEGAL CLASS --> https://www.samvanderwielen.com/live-legal-workshop
Subscribe to Sam's Substack
Read today's essay Field notes from NYC: reclaiming my own taste
If you have a question you’d like Sam to answer on a future podcast episode, you can submit it here.
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
Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER
11 min
July 2015 Habits that Rebuilt Me After I Lost Everything [Summer Read-Aloud]
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 habits that helped me rebuild after burnout and loss, some I learned the hard way, some I'd skip again, but all of them helped me feel better inside and out.
In this episode, you'll hear…
Why grief changed what actually felt worth my time and energy, in business and in life
The health habits (starting with what I eat first thing in the morning) that have made the biggest difference in how I feel
My digital wellness rules, including why I brick my phone every single night
The business habits that protect my creative energy and keep me from chasing everyone else's version of success
Why I still believe in "them" focused content, but why "you" content matters too

Click here to find the full show notes and transcript for this episode.
EPISODE RESOURCES:
Get Sam's weekly newsletter, Sam's Sidebar
👩🏻‍💻 REGISTER FOR MY FREE LIVE LEGAL CLASS --> https://www.samvanderwielen.com/live-legal-workshop
Subscribe to Sam's Substack
Read today's essay Healthy Habits that rebuilt me after burnout & loss
The Brick, the phone-blocking device Sam uses to disable apps (affiliate link)
Cometeer, the half-caff coffee Sam switched to (affiliate link)
Grab Sam's Book When I Start My Business, I'll Be Happy
If you have a question you’d like Sam to answer on a future podcast episode, you can submit it here.
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
Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER
12 min
July 13More Memories of Other People's Lives Than Our Own [Summer Read-Aloud]
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 actually like to run a seven-figure business while also trying to build a life off the very apps I used to build it. This particular essay gets into something I don't talk about all that often: how losing both of my parents within a year of each other completely cracked open the way I think about time, attention, and what I actually want my life to look like — phone down or not.
In this episode, you'll hear…
Why getting offline isn't just about swapping one app for a "better" one
The unsettling stat about our generation and other people's memories that I can't stop thinking about
How losing both of my parents within a year of each other changed my relationship with my phone, and with my life
What it actually looked like for me to start rebuilding an offline life on purpose, not by accident
Why the more offline I get, the better my online business actually does

Click here to find the full show notes and transcript for this episode.
EPISODE RESOURCES:
Get Sam's weekly newsletter, Sam's Sidebar
👩🏻‍💻 REGISTER FOR MY FREE LIVE LEGAL CLASS --> https://www.samvanderwielen.com/live-legal-workshop
Subscribe to Sam's Substack
Read today's essay How I Got (More) Offline
Grab Sam's Book When I Start My Business, I'll Be Happy
If you have a question you’d like Sam to answer on a future podcast episode, you can submit it here.
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
Take Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"

DISCLAIMER
12 min

About On Your Terms®

From the publisher's feed

A podcast for online business owners who refuse to choose between revenue and a real life. Most business advice tells you to hustle harder, post more, and "always be on." I'm here to tell you that's BS—and I have the multi-seven-figure business to prove it. I'm Sam Vander Wielen, and I've built a thriving online business while protecting my mornings, unplugging at night, and actually living the life I built my business for.