Latest / The Comeback Career Podcast with Fexingo: Returning After a Gap, Stay-at-Home Re-Entry / How a Career Gap Helped One Parent Return as an Executive Assistant
Transcript
- Lucas: Jenna Martinez spent nine years at home raising her two kids. Before that, she was a senior project manager at a regional construction firm. When she decided to go back, she assumed recruiters would see a decade of solid experience and not care much about the gap. Luna: And they did care? Lucas: They did. She sent out maybe forty applications in the first month for project management roles. She got two callbacks. Both ended with the same question: 'So what have you been doing since 2017?' And she didn't have a tight answer. Luna: That's the part most returners struggle with — the story around the gap. It's not the gap itself, it's how you frame it. Lucas: Exactly. And Jenna's pivot wasn't what I expected. She didn't try to re-enter as a project manager. She aimed for executive assistant roles. Specifically, she wanted to support a CEO. That decision was deliberate, and it changed everything. Luna: Why executive assistant? That's a pretty different lane from construction project management. Lucas: She told me she'd been the person who kept everything running at home — school schedules, medical appointments, contractor coordination, family travel. She realized that the core of executive assistance is exactly that: anticipating needs, juggling priorities, communicating across stakeholders. She wasn't starting over; she was translating. Luna: That makes a lot of sense. But I imagine recruiters still wanted to see some kind of formal qualification or recent office experience. Lucas: They did. So she got certified. She completed the American Society of Administrative Professionals' executive assistant certification — it's an online program, takes about six weeks if you're focused. She also did a two-day course on calendar management for executives. She spent maybe eight hundred dollars and forty hours total. Luna: And that was enough to get interviews? Lucas: It got her in the door. But the real breakthrough was how she reframed her resume. She wrote a summary line that said: 'Senior project manager with 8 years experience in operations and scheduling, returning after a family sabbatical.' She listed her project management experience first, then added a section called 'Family Operations Management' with bullet points like 'managed complex calendar of five family members across multiple activities' and 'coordinated home renovation projects with contractors and vendors.' Luna: I love that — 'family sabbatical' instead of a gap. And she treated parenting as a job with deliverables. Lucas: Right. And in interviews, when the gap came up, she had a two-sentence answer: 'I took a career break to raise my children full time. I stayed sharp through volunteer leadership in a parent-teacher organization and by managing our family's logistics, which I've found directly maps to executive support.' Then she'd give a specific example — like planning a school fundraiser with a ten thousand dollar budget and fifty volunteers. Luna: That's concrete. It shows she can manage resources and people. It's not a story about being out of the loop. Lucas: Exactly. She ended up with three offers. She took a role as executive assistant to the CEO of a mid-sized software company. The CEO told her later that what sealed it wasn't her certification or her old job title — it was the way she described coordinating a family move across state lines in three weeks. He said, 'If you can do that, you can handle my travel schedule.' Luna: That's a really practical example for anyone listening who's thinking about re-entry. It's not about downplaying the gap — it's about making the case that the gap taught you something valuable. Lucas: If today was actually useful to you, the way these stay ad-free is listener support. You can buy me a coffee at buy me a coffee dot com slash fexingo. Every bit keeps this going without sponsors. Luna: Yeah, it's a small way to say this kind of practical career help matters. We'll keep doing them either way, but it definitely helps. Lucas: So back to Jenna's story — the other thing she did that I think is worth noting is she networked intentionally. She didn't just apply online. She found the CEOs of small to mid-size tech companies on LinkedIn and sent them a short message: 'I'm a returning professional with a background in project management and I'm targeting executive assistant roles. I admire what your company is doing. Would you be open to a fifteen-minute conversation?' Luna: That's bold. Did she get responses? Lucas: She sent about thirty of those. Five CEOs replied. Two led to informational interviews. One of those became her eventual boss. The CEO said he'd never had an EA candidate reach out directly like that, and it showed initiative. Luna: So in her case, the career gap didn't hold her back — it actually became a differentiator because she framed it as a period of developing real-world management skills. Lucas: That's the key takeaway. She didn't hide the gap or apologize for it. She treated it as part of her professional story. And she targeted a role where the skills she had — organization, communication, crisis management — were exactly what the job required. Luna: It's also smart that she went for a smaller company. A lot of returners assume they need to start at a big corporation, but smaller firms often have less rigid hiring filters and more appreciation for a generalist skill set. Lucas: Completely agree. Jenna said in her interviews at larger companies, she got asked about software proficiency and specific years of recent EA experience. At the mid-size company, the CEO cared more about whether she could handle ambiguity and keep him on schedule. She could point to her family operations section and say, 'I've been doing this for years, just without the corporate title.' Luna: One thing I'd add for listeners: the certification she got is not expensive and it's widely respected. The ASAP certification is about four hundred dollars, and the calendar management course was another hundred. That's a pretty low cost for a credential that signals you're serious about re-entry. Lucas: And it gave her something recent to put on her resume. Recruiters like to see something from the past year, even if it's a course. It shows you haven't been idle. Luna: What's Jenna doing now? It's been about a year since she started, right? Lucas: She's been in the role for fourteen months. She's now managing not just the CEO's schedule but also coordinating with the executive team. She told me she's already been promoted to senior executive assistant. The CEO told her she's the best hire he's made in three years. Luna: That must feel validating after nine years out. Lucas: She said it was. Her biggest advice for other returners: don't aim for the role you left. Aim for the role that uses what you've become good at. In her case, parenting made her a better project manager — she just had to call it something different. Luna: That's a great note to end on. Thanks, Lucas. Lucas: Thanks, Luna. And if you're listening and trying to figure out your own re-entry story, we'd love to hear how it goes. Reach out anytime.