There’s a moment before something great happens in your career. It’s a pause, a hesitation, a feeling of “maybe I shouldn’t do this”.
And it’s completely normal.
In every success story you’ve ever read about, there was a moment that person simply didn’t feel ready. Their success stories point to a pivotal moment where, even at their most doubtful, they said: yes.
Think of this less as a guide or a playbook and more as a reminder: if you’ve ever felt discouraged trying to see yourself through to a goal, you’re not alone.
The Writer Who Built a Website – Without Knowing How
Ashley Segura is the Director of Marketing at SearchLab Digital and a 15-year marketing veteran who founded four companies along the way. Fun Fact: None of this was planned.
And all of her success can be traced back to a single yes she almost didn’t say.
Back when she was a recent journalism graduate with no web experience, she got a request from which most people would walk away.
Her family’s insurance agent asked if she could build him a website. The honest answer? She had no idea how to build a website. Instead, she said yes, and then Googled WordPress.
By leaning on her writing instincts, she was able to figure it out, and, against all odds, the site worked.
The insurance agent was so pleased he invited her to present to the California Board of Insurance Agents and share how she did it. She had never spoken publicly before. She said yes to that too. She left with a list full of prospective clients.
That one yes, to build a website she had no idea how to build, set off a speaking career, an agency, four companies, and a seat on global marketing stages.
“100% of my success, I attribute to journalistic curiosity and the willingness to figure things out on the fly,” she said on TDMM Episode 115. “If I had said no to that website, I honestly don’t know if I would have found my way into marketing at all.”
Fear Is Not a Stop Sign
The version of this story that doesn’t get told often enough is what it felt like in the middle. Ashley didn’t build a website with confidence. She built it with determination and a search engine, learning the skill only after she’d already said yes.
She’s developed a way of reading that feeling over the years. “If saying yes to something is terrifying, that’s often a signal I’m on the right path,” she says. “I’ve learned to lean into that discomfort rather than away from it.”
This is what career change courage actually looks like: moving through the fear instead of waiting for it to disappear. The butterflies before a new career path, a public commitment, a course enrollment: those aren’t warnings. They’re signs you’re at the edge of something real. Fear in the context of growth feels different from fear in the context of a genuinely bad idea. Learning to tell the difference is one of the most useful things you can develop.
Overcoming self-doubt in a career transition isn’t a prerequisite for starting. It’s a result of starting. The entry requirement isn’t mastery. It’s resourcefulness. The willingness to find out.
Other People Who Said Yes Too Early
Ashley’s story is the most detailed, but it’s not the only one.
Fay Friedman took a CMO role in commercial real estate knowing nothing about the industry. “I was thrown in the deep end,” she said. “I knew nothing.” She said yes first and figured out the rest after. (TDMM Episode 022)
Chayale Kaufman went from seminary to selling ad space to founding the Jewish Content Network. “I didn’t know what I was getting myself into, honestly,” she said. “But once I stepped into the office, I loved it.” (TDMM Episode 037)
Sicily Dickenson was promoted to VP of Advertising at NRG, a role neither she nor the company had built before. “I usually walk into things fairly without fear,” she said, “assuming that I’ll figure out how to do it.” (TDMM Episode 047)
Tracy Murray left a decade as a rehab director for marketing with zero experience, pushing past the “who do you think you are?” voice in her head. She later completed ODEO’s Digital Marketing Fundamentals course herself. (TDMM Episode 052)
Menashe Friedman started his consulting firm with no office, no phone line, and no plan. His episode title says it best: the perfect day to start is today. (TDMM Episode 106)
Tamara Gestetner spent 18 years as a therapist before burnout led her to finally say yes to stopping, a decision that led directly to her coaching practice and an upcoming podcast. She wasn’t ready to leave a career she’d built that long. She did it anyway. On TDMM Episode 109, she put it plainly: “You’re not married to a job. Just because you’re doing something now doesn’t mean you have to do it forever.”
Maggie Segrich co-founded Sesh Coworking in Houston when she realized people weren’t going to come to her home studio. She committed to HubSpot after watching three other CRM attempts fail, a yes that eventually transformed her entire operation. She came to it without the vocabulary to describe what she needed and found her way through anyway. (TDMM Episode 111)
In episode 117, Sophie Brannon left London at 18 to pursue music journalism, fell into digital marketing when the economics stopped working, and co-founded StudioHawk US in a market she’d never worked in. Year one: $1.2 million against a $400,000 projection.
The common thread isn’t confidence or credentials. It’s that all of them said yes before they had a reason to feel sure.
The Yes That Costs You Nothing
The career pivots above sound significant because they are. But the yes that starts everything rarely feels significant in the moment. Ashley’s first yes was to build a website. One small, manageable yes that she had no guarantee would lead anywhere.
That’s the question worth sitting with: what is the smallest possible yes you could say today?
For a lot of people reading this, that yes is finally looking into how to start a new career in digital marketing. Not quitting your job. Not committing to a new career before you know where it leads. Just beginning.
ODEO’s Digital Marketing Fundamentals course is built for exactly this moment: the curious person, not yet certain.
The person who wants to understand what paid search, SEO, and social media actually mean before deciding whether marketing is where they’re headed.
You don’t need prior experience. Leaping into a digital marketing career doesn’t require you to have it all figured out first. You need the willingness to find out.
That’s what Ashley had when she Googled WordPress. It’s what Tamara had when she left therapy. It’s what Sophie had when she bought a one-way ticket to Atlanta.
You don’t have to be ready. You have to be willing.
Start Here
Saying yes before you’re ready isn’t reckless. It’s how every career worth having got started.
If you’re curious about digital marketing and not yet sure where to begin, ODEO’s Digital Marketing Fundamentals course is the structured first yes. No prerequisites. No pressure to have it all figured out.
See what ODEO students say about making that first move, or read Tamara’s story: Career Reinvention Isn’t Reckless. Tracy Murray took the same leap. Hear how she went from rehab director to marketer on TDMM Episode 052.