What happens when the businesses you built are successful, making money...and you realize you don’t want them anymore?

Cindy Gordon built multiple online businesses, sold four of them, and chose to start over while the businesses were still working.

In this episode of She Chose Again, Cindy takes us back to the food blog that started as a hobby and unexpectedly became a real source of income. From there, she went on to build and run multiple websites, hire a team, create different revenue streams, and eventually make the decision to sell.

We talk about what that process actually looked like, including how the businesses made money, how she found buyers, what went into selling them, and what made her willing to walk away from something that was still successful.

And because Cindy has spent 17 years building businesses online, we also get into what she sees changing now: SEO, AI visibility, personal branding, getting found online, and why sounding like an actual person matters more than ever.

In this episode, we talk about:

• How a hobby food blog became a business
• When Cindy realized the income was becoming significant
• Building and managing multiple websites at once
• Hiring a team
• Why she decided to sell businesses that were still working
• How her businesses made money
• How she found buyers
• Networking, cold outreach, and building relationships
• Starting over with a completely different business
• SEO, AI, and the changing way people get discovered online
• What didn’t work along the way
• What Cindy is choosing now

Okay, Now What? is my Sunday newsletter about changing your mind, choosing again, and figuring out what comes next when the old plan doesn’t work anymore.

Subscribe:
https://letters.outofedits.com/

Website:
https://exclusivelycindy.com/

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

YouTube:
https://www.youtube.com/@cindygordon

She Chose Again is an Out of Edits interview series about women who changed their minds, changed direction, and chose something different for their lives.

These conversations go beyond the finished version. We talk about what happened next, how the change actually worked, what it cost, how they made money, what didn’t work, and the details that usually get skipped.

Out of Edits is a global publication for women who’ve outgrown the default path, exploring choice, reinvention, and the many ways women are building lives beyond the expected script.

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https://www.outofedits.com

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What does starting over actually look like when it happens more than once?

Usually, I’m the one asking the questions on What She Did Next. This time, my friend Tanisha interviewed me.

We talked about the many times I’ve changed direction...leaving corporate, moving across the country, changing careers, becoming a freelancer, traveling solo, living abroad, and figuring out the money along the way.

This is less of a clean “I changed my life and everything worked out” story and more about what starting over actually looked like for me. The plans that changed. The money decisions. The periods where I had no idea what I was doing. The times I disappeared while trying to figure things out. And why I’ve gotten so comfortable changing my mind when something isn’t working.

If you’re thinking about starting over in your 30s or 40s, changing careers, freelancing, solo travel, living abroad, or creating a life that looks different from what you originally planned, this conversation gets into the parts that usually get skipped.

In this episode, we talk about:

• Career changes and leaving corporate
• Money and preparing for major life changes
• Freelancing and alternative ways of working
• Solo travel and living abroad
• Starting over without having the whole plan
• What the messy middle actually feels like
• Changing your mind without treating it like failure

About Out of Edits

Out of Edits is a global publication for women who’ve outgrown the default path, exploring choice, reinvention, and the many ways women are building lives beyond the expected script.

Subscribe for more conversations with women who changed direction, started over, and figured out what came next.

KEEP READING WITH OUT OF EDITS

If you're figuring out what you want next, She Chose Again is my Sunday letter about choice, reinvention, and expanding your idea of what's possible.

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https://letters.outofedits.com/

After a layoff and nearly two years of living on savings, Brandy Savage moved back home at 42 and began rebuilding her life in public.

In this episode of What She Did Next, Brandy talks with host Elle Mills about starting over in your 40s, leaving corporate life, becoming a beginner again, and finding ways to earn money while figuring out what comes next.

Brandy calls this her “midlife alignment era.” We get into what moving home made possible, the pressure to follow a life blueprint, and the question guiding her now: Do you have the courage to make up the rules for your own life?

CONNECT WITH BRANDY

YouTube: https://www.youtube.com/@thebrandysavage
Instagram: https://www.instagram.com/thebrandysavage/
Threads: https://www.threads.com/@thebrandysavage
TikTok: https://www.tiktok.com/@brandysavage

Get the Sunday letter, She Chose Again: https://letters.outofedits.com/

What happens when you know your life needs to change, but you have no idea what comes next?

Ashley Langham has gone from finance and compliance to marketing, copywriting, spirituality and healing, with career changes and moves across five countries along the way.

Ashley and Elle talk about starting over after burnout, leaving corporate, finding freelance clients, building multiple income streams, transferring old skills into new work, and what happens when the plans you make keep falling apart. There’s also a startup job that lasted two months, a spiritual retreat center Ashley later came to consider a cult, and the realization that even after leaving corporate, she was still treating herself like an employee.

For anyone considering a career change, starting over in their 30s or 40s, becoming self-employed, moving abroad, or trying to figure out what comes next without having the whole plan figured out.

About Ashley LanghamAshley is the founder of Thoughtful Thorough and describes herself as a mystic mentor, strategist and psychic healer.

Keep reading with Out of Edits
She Chose Again is a Sunday letter about choice, reinvention and the different ways women are building lives beyond the expected script.

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Content note: This episode includes discussion of depression and suicidal ideation.