What happens when you get everything you worked for and it still isn't enough? That's exactly where this week's guest, Sam Vander Wielen, found herself. Sam spent years building a career as an attorney, only to discover that the title, the salary, and the respect that were supposed to make her happy left her miserable instead. So she walked away and built a business from scratch — one that's since made over $10 million from a single digital product. In this episode, Sam and I dig into what she calls "the happiness trap": the belief that once a certain thing happens, we'll finally feel happy, worthy, or at peace. We talk about why that belief rarely holds up, even when the thing you were chasing actually comes true, and what to do instead if you're waiting for "someday" to start feeling better about your life.

If this conversation has you thinking about finally starting the business you've been sitting on, my free Small Business 101 course walks you through exactly how to get started: https://gillianperkins.com/free-training-small-business-101/

In This Episode, I Cover:

What the "happiness trap" is, and why almost all of us fall into it without realizing it
Sam's story of chasing a law career for the status and security, only to find it made her miserable
Why even wild success in her own business didn't automatically deliver the happiness she expected
The reason we tend to revert to the same baseline of happiness no matter how much our circumstances change
How negativity bias explains why one nasty comment can undo ninety-nine kind ones
The "arrival fallacy," and how it can trap you twice — once chasing a career, then again chasing the business meant to replace it
Sam's practical steps for building happiness now instead of waiting for "someday," including her "five-second rule" for trying new hobbies
Why Sam believes it isn't your job's — or your business's — job to make you happy
Her advice for anyone sitting on a business idea right now, and how to find out if people actually want it before you build it

Connect with Sam Vander Wielen:

When I Start My Business, I'll Be Happy: https://www.samvanderwielen.com/book/

On Your Terms: https://www.samvanderwielen.com/podcast/

Instagram: https://www.instagram.com/samvanderwielen/

Free live class (her last one of 2026, Monday, October 19) on how to start an online business legally, plus what's changing with AI disclosure policies and ADA website lawsuits — sign up for free access and the replay here: https://samvanderwielen.samcart.com/referral/oct-live/rOhbxf8KbgOnMbqq

Free Resources to Grow Your Online Business:

$100K Method (free audio course): https://www.gillianperkins.com/100k-method-signup

Small Business 101 (free course): https://gillianperkins.com/free-training-small-business-101/

Work with Gillian Perkins:

Startup Society: https://startupsociety.com

$100K Mastermind: https://gillianperkins.com/100k-mastermind

Connect with Gillian:

Website: https://gillianperkins.com

Instagram: https://instagram.com/gillianzperkins/