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Share How to Live a Non-Regrettable Life + Ask for What You Want (Even If You’re Scared to Fail) with Podcast Strategist & Digital Nomad, Chelsea Riffe
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How to Live a Non-Regrettable Life + Ask for What You Want (Even If You’re Scared to Fail) with Podcast Strategist & Digital Nomad, Chelsea Riffe
In this powerful and wildly relatable episode, Jess and Rye sit down with podcast strategist and storytelling expert Chelsea Riffe to unpack what it really means to live a non-regrettable life—and the fears, failures, and uncomfortable conversations it takes to get there. From asking for what you want (in relationships, career, and business) to pitching yourself like a pro, this episode is packed with tangible mindset shifts, hilarious real-life stories, and motivational gold.
✨ Key Topics We Cover:
- What living a non-regrettable life means (and why it's less about big wins and more about intentional choices)
- Learning to ask for what you want and the concept of the “third door”
- Dealing with rejection without spiraling (and building a nervous system that can handle more)
- Chelsea’s career leap from corporate sales to digital nomad & podcast coach
- Messaging and pitch mistakes to stop making ASAP
- How to start living with more confidence before you feel “ready”
- Why your “failure tolerance” may be the key to creating the life you want
- The underrated power of booking one-way flights, knowing your Human Design, and sliding into DMs
Resources Mentioned:
Brene Brown’s teachings on vulnerability and rejection
Chelsea’s program: Pitch Perfect - next round in late 2025
Connect with Chelsea:
Chelsea’s website
Chelsea’s Instagram
1:1 Podcast Coaching
Mic Drop Podcast Launch Course
Slight Turbulence Substack
Follow The Hosts:
🎧 Podcast IG → @solo2.0podcast
💜 Jess’s IG → @bodyblissbyjess
💜 Rye’s IG → @ryeburch
📩 Email Us → [email protected]
✨ Hormone Testing & Consulting → Your Hormone Balance
🧡 If this episode resonated, be sure to rate + review—it really helps us grow!
⏳ Episode Timestamps:
05:00 - Chelsea’s intro & what a non-regrettable life means to us
20:00 - How Chelsea built her dream business from scratch during lockdown
25:00 - “Shoot your shot” mindset: from asking for rent discounts to pitching podcasts
35:00 - Building confidence without a roadmap + via negativa approach to clarity
40:00 - Rejection, failure tolerance, and not dying when someone says no
50:00 - Why women struggle to ask for more—and how to break that cycle
58:00 - Passive language to cut from your emails today
1:00:00 - Tips for building your nervous system to handle more success
1:04:00 - Underrated/Overrated: one-way flights, cold emails, working for free & more
View all episodes
By Ryan Burch and Jess Suchan
4.9
8787 ratings
In this powerful and wildly relatable episode, Jess and Rye sit down with podcast strategist and storytelling expert Chelsea Riffe to unpack what it really means to live a non-regrettable life—and the fears, failures, and uncomfortable conversations it takes to get there. From asking for what you want (in relationships, career, and business) to pitching yourself like a pro, this episode is packed with tangible mindset shifts, hilarious real-life stories, and motivational gold.
✨ Key Topics We Cover:
- What living a non-regrettable life means (and why it's less about big wins and more about intentional choices)
- Learning to ask for what you want and the concept of the “third door”
- Dealing with rejection without spiraling (and building a nervous system that can handle more)
- Chelsea’s career leap from corporate sales to digital nomad & podcast coach
- Messaging and pitch mistakes to stop making ASAP
- How to start living with more confidence before you feel “ready”
- Why your “failure tolerance” may be the key to creating the life you want
- The underrated power of booking one-way flights, knowing your Human Design, and sliding into DMs
Resources Mentioned:
Brene Brown’s teachings on vulnerability and rejection
Chelsea’s program: Pitch Perfect - next round in late 2025
Connect with Chelsea:
Chelsea’s website
Chelsea’s Instagram
1:1 Podcast Coaching
Mic Drop Podcast Launch Course
Slight Turbulence Substack
Follow The Hosts:
🎧 Podcast IG → @solo2.0podcast
💜 Jess’s IG → @bodyblissbyjess
💜 Rye’s IG → @ryeburch
📩 Email Us → [email protected]
✨ Hormone Testing & Consulting → Your Hormone Balance
🧡 If this episode resonated, be sure to rate + review—it really helps us grow!
⏳ Episode Timestamps:
05:00 - Chelsea’s intro & what a non-regrettable life means to us
20:00 - How Chelsea built her dream business from scratch during lockdown
25:00 - “Shoot your shot” mindset: from asking for rent discounts to pitching podcasts
35:00 - Building confidence without a roadmap + via negativa approach to clarity
40:00 - Rejection, failure tolerance, and not dying when someone says no
50:00 - Why women struggle to ask for more—and how to break that cycle
58:00 - Passive language to cut from your emails today
1:00:00 - Tips for building your nervous system to handle more success
1:04:00 - Underrated/Overrated: one-way flights, cold emails, working for free & more
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