"I used to sell for a living. Now I can't even sell myself."

Oct 09, 2026

Today I’m analysing the situation of Naomi.

Naomi reached out about joining my Creative Career Level Up programme after more than two years of trying to get back into a senior partnerships role. 

Since her position at a big-name brand was eliminated, she's applied for hundreds of jobs and made it to final rounds with some exciting companies, only to be ghosted.

The little feedback she's had is always the same: they couldn't work out the scope of her role. That stings, because Naomi started her career in sales, always at the top of the leaderboard.

"I used to sell for a living. Now I can't even sell myself."

What's the challenge?

Naomi hasn't lost her ability. What she's lost is her confidence, and it's leaking into every conversation. She's self-conscious about the gap, so she rushes past it, then falls back on a chronological walk through her CV. Hiring managers leave without a clear picture of what she'd actually do for them.

How can she move forward?

Naomi needs to stop treating the gap as the headline and start leading with the value she brings. She also needs more of her applications landing in front of real people, so she can see what's working and what isn't.

My advice

1. Don't let the gap do the talking 

The gap doesn't erase the years Naomi spent doing brilliant work, and most interviewers care far more about what's on her CV than what isn't. We tend to worry about gaps much more than the person across the table does. Naomi needs one short, honest line about that time, and then a confident pivot back to the experience that makes her right for the role.

2. Get out of the ATS and back into your network 

Naomi has been rejected automatically for roles that read like a recap of her old job. That's a broken system, not a verdict on her. Reigniting her network, using simple scripts so it doesn't feel like hassling people, and getting her CV directly to hiring managers will show us what happens when a human actually sees it.

3. A good-feeling interview isn't always a good interview 

Naomi often predicted the questions perfectly, but predicting the question isn't the same as giving the best answer. Every answer should be chosen to feed the story she wants them to remember, starting with "Tell me about yourself". Once she frames herself as the solution to their problem, the scope question answers itself.

If Naomi's story sounds familiar, and you know you're good at what you do but can't seem to get that across, I'd love to help.

Check out more details, including testimonials, on our website here.

I help people in the Marketing and Creative and Tech Industries to find their next perfect role. 

If you are looking to level-up your career, use the link below to schedule some time to chat about whether the programme might be right for you.

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