EPISODE · Mar 4, 2026 · 35 MIN
Freedom, Flexibility, and Financial Reality — Succeeding as a Solopreneur with Elaine Pofeldt
from Thinking Solo · host Ryan Derousseau, CFP®, EA
On this episode of Thinking Solo, host Ryan Derousseau, CFP®, EA, sits down with author and freelance journalist Elaine Pofeldt to talk about what it really takes to succeed as a solopreneur.Elaine has been running her solo business since 2007 and is the author of Tiny Business, Big Money and The Million-Dollar One-Person Business. She shares how building a solo business allowed her to be present while raising four children, and why she considers that flexibility one of the greatest rewards of working for yourself.Together, Ryan and Elaine dig into the less-glamorous realities of freelance and solo work: uncertainty, discipline, financial resilience, taxes, health insurance, and the constant need to balance client work with business development. They also explore why so many people (at every life stage) are choosing the solopreneur path in search of freedom.In this episode, you’ll learn:• Why solopreneurs rarely feel “fully comfortable” — and why that’s normal• How recurring clients and retainers build confidence and stability• The importance of discipline, planning, and managing multiple roles• Why living below your means creates resilience when clients disappear• Smart ways freelancers can prepare for taxes and avoid surprises• The biggest financial hurdle Elaine faced as a solo business owner• Why “freedom” is the common thread driving people toward solo work• How AI and technology are powerful tools for solopreneurs without capital• Why freelancers often report better health than corporate employees• The value of non-screen outlets and trusted “freelance buddies”This conversation is a grounded look at solo business ownership… The trade-offs, the rewards, and the systems that make it sustainable over the long term.---Connect with Elaine Pofeldt:LinkedIn: http://linkedin.com/in/elainepofeldt/YouTube: http://youtube.com/UCr5VUkqfMpz_JPGnnXu3F8aWebsite: https://www.elainepofeldt.com/Connect with Ryan Derousseau, CFP:Email: [email protected]: https://www.linkedin.com/in/ryanderousseau/ Website: https://thinkingcapfinancial.com/
What this episode covers
On this episode of Thinking Solo, host Ryan Derousseau, CFP®, EA, sits down with author and freelance journalist Elaine Pofeldt to talk about what it really takes to succeed as a solopreneur.Elaine has been running her solo business since 2007 and is the author of Tiny Business, Big Money and The Million-Dollar One-Person Business. She shares how building a solo business allowed her to be present while raising four children, and why she considers that flexibility one of the greatest rewards of working for yourself.Together, Ryan and Elaine dig into the less-glamorous realities of freelance and solo work: uncertainty, discipline, financial resilience, taxes, health insurance, and the constant need to balance client work with business development. They also explore why so many people (at every life stage) are choosing the solopreneur path in search of freedom.In this episode, you’ll learn:• Why solopreneurs rarely feel “fully comfortable” — and why that’s normal• How recurring clients and retainers build confidence and stability• The importance of discipline, planning, and managing multiple roles• Why living below your means creates resilience when clients disappear• Smart ways freelancers can prepare for taxes and avoid surprises• The biggest financial hurdle Elaine faced as a solo business owner• Why “freedom” is the common thread driving people toward solo work• How AI and technology are powerful tools for solopreneurs without capital• Why freelancers often report better health than corporate employees• The value of non-screen outlets and trusted “freelance buddies”This conversation is a grounded look at solo business ownership… The trade-offs, the rewards, and the systems that make it sustainable over the long term.---Connect with Elaine Pofeldt:LinkedIn: http://linkedin.com/in/elainepofeldt/YouTube: http://youtube.com/UCr5VUkqfMpz_JPGnnXu3F8aWebsite: https://www.elainepofeldt.com/Connect with Ryan Derousseau, CFP:Email: [email protected]: https://www.linkedin.com/in/ryanderousseau/ Website: https://thinkingcapfinancial.com/
NOW PLAYING
Freedom, Flexibility, and Financial Reality — Succeeding as a Solopreneur with Elaine Pofeldt
No transcript for this episode yet
Similar Episodes
Feb 8, 2026 ·26m