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 almost begged for my job back.👩🏻‍💻 REGISTER FOR MY FREE LIVE LEGAL CLASS --> https://www.samvanderwielen.com/live-legal-workshop (Replay included!)In this episode, you'll hear…Why "just take the leap" can be financially irresponsible adviceHow much savings I recommend having before you leaveHow I started paying myself (hint: $500 a month)What to know about health insurance when you go self-employedThe backend setup to do while you're still getting a paycheckHow to tell if you need a business or just a different jobWhy fear after the leap doesn't mean you chose wrongClick 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 EntrepreneurshipCheck out KIT & get your first month free (affiliate link)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 outCONNECT:Get Sam's weekly newsletter, Sam's SidebarFollow Sam on InstagramFollow Sam on YouTubeSubscribe to Sam's SubstackTake Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"DISCLAIMER

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.→ Register free for my last live legal workshop of 2026 called "How to Start an Online Business Legally Before 2026 Ends" on Monday, October 19: https://www.samvanderwielen.com/live-legal-workshopCan't make it live? Sign up ^ and I'll send you the replay.In this episode, you'll hear…What's changing with AI labeling, and what it means for how you create and postWhy your personal privacy matters more than ever when you're the face of your businessWhy ADA lawsuits are on the rise, and how to get ahead of themWhere we'll dig in together: my free live workshop on Monday, October 19EPISODE RESOURCES:Save your free seat at my live legal workshop on 10/19: https://www.samvanderwielen.com/live-legal-workshop (Replay included!)In my live legal workshop, I'll share the easy ways to navigate these legal changes, and teach you how to start an online business legally before 2026 ends. See you there!CONNECT:Get Sam's weekly newsletter, Sam's SidebarFollow Sam on InstagramFollow Sam on YouTubeSubscribe to Sam's SubstackTake Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"DISCLAIMER

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 RubinWhat makes a quiz lead magnet actually work, and why treating your results page like a "hostage situation" is costing you subscribersA genius (and totally free) way to turn nice DMs and emails into public reviews and testimonialsWhat 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 inHallway chats with health coach Dan Go and Nerd Fitness founder Steve Kamb about fighting for your own art and doing things your wayClick 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 EntrepreneurshipCheck out KIT & get your first month free (affiliate link)Craft and Commerce recap episodeSam's previous mastermind recap episode from earlier this yearDan Go: https://dango.co & InstagramSteve Kamb: https://stevekamb.com & InstagramIf 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 outCONNECT:Get Sam's weekly newsletter, Sam's SidebarFollow Sam on InstagramFollow Sam on YouTubeSubscribe to Sam's SubstackTake Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"DISCLAIMER

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 everywhereWhy I'd ditch a "social media first" approach entirely and build an audience-first business insteadWhat I wish I'd done sooner when it comes to getting comfortable charging for my content and expertiseHow I shifted from "post everywhere, all the time" to focusing on fewer, bigger tasks that actually move my business forwardWhy "pace" today means being reactive and in the conversation, not just pumping out volumeClick 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 SidebarSubscribe to Sam's SubstackEpisode 280. How I Got My First 1,000 Subscribers on SubstackIf 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 outCONNECT:Get Sam's weekly newsletter, Sam's SidebarFollow Sam on InstagramFollow Sam on YouTubeSubscribe to Sam's SubstackTake Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"DISCLAIMER

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 wayThe 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 onlineThe moment I realized what I was actually feeling wasn't guilt about overcommitting. It was judgmentClick 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 boringGet Sam's book When I Start My Business, I'll Be HappyGet Sam's weekly newsletter, Sam's SidebarIf 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 outCONNECT:Get Sam's weekly newsletter, Sam's SidebarFollow Sam on InstagramFollow Sam on YouTubeSubscribe to Sam's SubstackTake Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"DISCLAIMER

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 involvedThe connection I draw between forcing my body to heal on it's own timelineClick 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 downGet Sam's weekly newsletter, Sam's SidebarIf 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 outCONNECT:Get Sam's weekly newsletter, Sam's SidebarFollow Sam on InstagramFollow Sam on YouTubeSubscribe to Sam's SubstackTake Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"DISCLAIMER

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 confidenceWhat 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 perspectiveHow coming home to Long Island turned into an unexpected obsession with birdwatchingWhat robins, swans, and bald eagles taught me about noticing the seasons changing, even when I couldn't feel it yetWhy paying attention to the small, local, unglamorous things is what's actually helped me feel rooted and connected, more than anything online ever hasClick 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 offlineGet Sam's weekly newsletter, Sam's SidebarIf 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 outCONNECT:Get Sam's weekly newsletter, Sam's SidebarFollow Sam on InstagramFollow Sam on YouTubeSubscribe to Sam's SubstackTake Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"DISCLAIMER

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 meHow my 2026 "gap year" backfired into more batching and pressure instead of the spaciousness I wantedThe real cost of optimizing everything, and why productivity can quietly kill creativityWhy AI is making the content arms race worse, not betterWhat actually refills my creative well, and why living your life is the best content strategy there isClick 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 creativityGet Sam's weekly newsletter, Sam's SidebarIf 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 outCONNECT:Get Sam's weekly newsletter, Sam's SidebarFollow Sam on InstagramFollow Sam on YouTubeSubscribe to Sam's SubstackTake Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"DISCLAIMER

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 anywayThe real reason I keep reaching for my phone, even when I'm trying to unplugWhat my brutally honest friend said that made me realize my "time off" looked exactly like workHow grief shows up in the smallest, most random moments, and why distraction feels easier than sitting with itWhy I'm learning to be kinder to myself about the blurry line between resting and being restlessClick 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 thisIf 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 outCONNECT:Get Sam's weekly newsletter, Sam's SidebarFollow Sam on InstagramFollow Sam on YouTubeSubscribe to Sam's SubstackTake Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"DISCLAIMER

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 decisionsWhy I think over 80% of Instagram-hyped restaurants aren't even worth the hypeWhat my no-buy Amazon year has taught me about slowing down and shopping with intentionThe conversations with local shop owners that ended up meaning more than any five-star reviewHow I'm working to reclaim my own preferences, both in New York City and in my everyday lifeClick 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 SubstackRead today's essay Field notes from NYC: reclaiming my own tasteIf 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 outCONNECT:Get Sam's weekly newsletter, Sam's SidebarFollow Sam on InstagramFollow Sam on YouTubeSubscribe to Sam's SubstackTake Sam's free legal workshop "5 Steps to Legally Protect & Grow Your Online Business"DISCLAIMER