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 advice
- How much savings I recommend having before you leave
- How I started paying myself (hint: $500 a month)
- What to know about health insurance when you go self-employed
- The backend setup to do while you're still getting a paycheck
- How to tell if you need a business or just a different job
- Why fear after the leap doesn't mean you chose wrong
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)
- 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"

