517: After Quitting My 6-Figure Job to Launch My Own Business Here’s What I Learned

Side Hustle Pro

Nicaila Matthews Okome | Side Hustle Pro Media

Blackpodcast, Sidehustlepro, Blackwomenownedbusiness, Entrepreneurship, Nicailamatthewsokome, Blackentrepreneurs, Sidehustleshow, Smallbusinessshow, Smallbusinessowners, Smallbusinesspodcast, Marketing, Sidehustle, Blackownedbusiness, Blackwomenentrepreneurs, Business, Sidehustles, Businesspodcast, Blackwomen

4.7 • 1.8K Ratings

🗓️ 5 June 2026

⏱️ 26 minutes

🔗️ Recording | iTunes | RSS

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Summary

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In this solo episode, I'm pulling back the curtain on my entrepreneurial journey and sharing the six most important lessons I've learned since leaving my corporate job in 2017. Most people assume that quitting was my biggest risk, but the truth is, the scariest steps happened long before I ever turned in my notice.

I take you all the way back to 2015, when I graduated from business school without a job after not receiving the full-time offer from my Google internship. From studying abroad in Barcelona to avoid reality, to moving back to DC and starting a blog with no plan, this episode is about what really happens in the messy middle before success shows up. I share how rejection led me to NPR, how my experience there became the foundation for Side Hustle Pro, and how I earned my first $4,000 sponsorship contract from a cold email to a customer service inbox.

This episode is for anyone who is waiting for a sign, a plan, or the perfect moment. Spoiler: that moment is not coming. What is coming is everything you need to build, but only if you start. I break down exactly how I got here and what I want you to take away from this milestone journey.

Main Takeaways

Rejection is redirection: Not getting the Google offer was the push that led Nicaila to build Side Hustle Pro.
You don't need the whole plan: Taking one next step, even without knowing where it leads, is how clarity is built.
Clarity comes from action: The idea for Side Hustle Pro did not come before the action; the action revealed the idea.
Bet on proof, not hope: Nicaila didn't quit her job out of fearlessness, she quit because she had consistent data showing her business could grow.

Highlights Include

[00:02] I share the real biggest risk I took, and it wasn't quitting my job
[00:24] The Google internship story: expecting the full-time offer and not getting it
[02:45] Graduating from business school with no job, no plan, and moving back to DC
[04:40] Lesson 1: Rejection is redirection, and what that looked like in real life
[07:16] Lesson 2: You don't need the whole plan, just the next step
[00:02 segment 2] Lesson 3: Clarity comes from action, not waiting for an aha moment
[03:11] How Side Hustle Pro's concept was born out of a boring blog pivot
[07:26] Lesson 5: Bet on proof, how I earned my first $4,000 sponsorship
[11:37] The real reason I quit: not fearlessness, but evidence
[12:19] Lesson 6: The life you want is built before you leave, not after

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Transcript

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0:00.0	There's no one day a business will just fall into your lap or one day your next move will just come into your lap.
0:06.3	Anything you want to do, the clarity comes from the action, y'all.
0:10.5	You have to take action some way somehow to get some more clarity.
0:14.4	So if you ever feel confused, if you ever feel like I don't know what to do next, I'm telling you, take a next step.
0:21.2	That is what's going to get you closer.
0:23.8	You're listening to Side Hustle Pro, the podcast that teaches you to build and grow your
0:29.2	side hustle from passion project to profitable business.
0:32.9	And I'm your host, Nikaela Matthews Okome.
0:35.5	So let's get started.
0:36.6	Thank you. host, Nikaela Matthews Okome. So let's get started.
0:49.1	So I quit my corporate job in 2017 almost 10 years ago. And most people think that this is the biggest risk that I took. But it actually wasn't. The biggest risk that I took was starting to take steps towards my
0:55.9	future before I knew where it was leading me. Here's what I mean. So in 2015, I graduated with my MBA
1:03.9	from business school with no job. I had interned between my first and second years of business
1:09.8	school at Google over in their
1:12.1	Mountain View campus.
1:13.9	And it was really exciting.
1:15.2	I worked in ad sales.
1:16.6	And for most people, when you go to business school to get your MBA and you do what's
1:22.0	called your MBA internship, you are expected to get the full-time offer.
1:27.0	You are expected to come back with a job. That's
1:30.0	just a given. And so for me, I had done really well. I'd gotten peer recommendations. I, you know,
1:37.1	really enjoyed my summer, worked with a wonderful team, and expected to get that offer, but it didn't
	...

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