3208: What If I Don’t Go Back To Work by Craig Stephens of Retire Before Dad on Financial Responsibility and Freedom

Optimal Finance Daily - Financial Independence and Money Advice

Optimal Living Daily LLC

Investing, Business, Education, Self-improvement

4.4 • 1.3K Ratings

🗓️ 11 July 2025

⏱️ 13 minutes

🔗️ Recording | iTunes | RSS

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Summary

Discover all of the podcasts in our network, search for specific episodes, get the Optimal Living Daily workbook, and learn more at: OLDPodcast.com. Episode 3208: Craig Stephens reflects on the tension between staying self-employed and returning to full-time work, balancing financial responsibility with the desire for autonomy. His honest exploration of fears, healthcare costs, shrinking savings, and the limits of side income contrasts with the freedom and fulfillment he’s found in family time and entrepreneurial efforts. His story offers clarity and comfort to anyone questioning the traditional 9-to-5 path. Read along with the original article(s) here: https://www.retirebeforedad.com/dont-go-back-to-work/ Quotes to ponder: "I'm home every day. I make breakfast for the kids and take them to school. I go to the gym when I feel like it." "Going back to full-time work, in a way, says that I can’t make enough money as an entrepreneur." "But the most painful aspect of full-time work is the loss of control of my time." Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	The weather. Tomorrow, expect a... Biting cold front. Hmm, how naughty. I wonder what I'll be wearing or taking off. The night will be wild and untamed. Expect heavy, lashing rain that'll soak you to the skin. By Monday, temperatures will rise slowly but surely reaching their peak in the afternoon.
0:23.1	Not in the mood for miserable weather?
0:25.9	Fly cheaply to Turkey with Sun Express.
0:28.7	Sun Express, nonstop sunshine.
0:32.7	This is Optimal Finance Daily.
0:35.1	What if I don't go back to work? By Craig Stevens of Retire Before Dad.com
0:39.0	Around friends and neighbors,
0:42.6	I'm using the phrase in-between jobs
0:45.1	to describe my current employment situation.
0:48.4	That's a convenient euphonism to make it sound less bad.
0:52.7	Most people aren't familiar with my business,
0:55.3	so they only see a jobless dad of three kids
0:58.4	married to a non-working mom
1:00.4	dealing with a mortgage
1:01.7	and the same suburban costs they struggle with.
1:05.3	I used the term unemployed the other day
1:07.7	with a former coworker,
1:09.4	and I sense sorrow in his replied text message.
1:13.0	Oh, he wrote, in a town where conversations often revolve around employment, I'm conflicted about my
1:20.2	actual status. Yes, I'm between jobs because I left a job and intend to go back to a new one.
1:29.8	Yes, I'm technically self-employed because I work on a business that earns money. Yet, I was laid off and I'm looking for work,
1:35.8	so I'm unemployed. The way I frame my story changes depending on who I talk to. The truest answer
	...

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