Career Reentry Tips: Bounce Back with Confidence

Re-Entering the Workforce After a Career Break: Insights from a Career Conversation

Returning to work after a career transition—especially following a break—can be daunting, particularly with a diverse resume or short job stints. In a GoCrackIt Career Conversations session, career transition coach Siddhartha Banerjee advised a professional on restarting their career through networking, freelancing, and strategic planning. Their insights, rooted in effective coaching for career transition, are invaluable for job seekers navigating this challenging phase.

Excerpts from the conversation:

Candidate: I’m targeting CSR, program management, and impact consulting roles, but I’m not getting shortlisted, even at top firms.

Siddhartha: Landing roles at top firms may take time due to your short stints and break. Start with smaller startups or freelance gigs to rebuild momentum. Larger opportunities will follow.

Siddhartha, acting as a career coach transition expert, proposed freelancing as a practical way to gain experience. He connected the candidate with a platform tailored for professionals undergoing a career shift, especially after a break.

Siddhartha: I’ll share your resume with a platform offering remote freelance gigs, typically six-month contracts paying modest salaries. Some companies may offer permanent roles. Are you open to this?

Candidate: Yes, I’m open to freelancing to gain experience.

Siddhartha: The platform will contact you. For in-person roles, I’ll check with management institutes for startup connections.

Networking was a key focus of their career transition services. Siddhartha encouraged leveraging past connections and exploring startup ecosystems to facilitate the candidate’s re-entry.

Siddhartha: Reach out to former colleagues for job leads. Check startup hubs like co-working spaces or institute incubation centers. Take on projects, even at lower pay, to rebuild experience.

Candidate: That’s new advice. I hadn’t considered startup hubs.

To address potential skill gaps during a career transition, Siddhartha emphasized practical experience over standalone certifications.

Candidate: Are there skill gaps I should address, maybe through online courses?

Siddhartha: Your frequent job switches are the main barrier, not skills. Pair certifications with startup projects to show commitment. Tell employers you upskilled to deliver better results—it’s impressive.

For long-term stability, Siddhartha advised aiming for a 3–5 year role, a crucial step in a successful career transition.

Siddhartha: Your next job should last three to five years. If you take a short stint, don’t include it—extend the career break. For CSR roles, consolidate social work under a “Program Management” heading, with a career timeline at the top. Keep the resume to one page by summarizing education and removing internships or interests.

Candidate: I heard timeline templates might not be ATS-compliant.

Siddhartha: A simple timeline and skills diagram is ATS-compliant. Avoid excessive graphics.

The candidate’s lengthy CV needed trimming, and Siddhartha provided clear guidance as part of his coaching for career transition.

Candidate: Should I remove certifications or awards to fit one page?

Siddhartha: Yes, prioritize education, summarize it in 3–4 lines. Remove internships, interests, and awards if needed. Include a concise skills diagram if space allows.

Siddhartha concluded with encouragement and next steps, highlighting the ongoing support available through GoCrackIt’s career transition services.

Siddhartha: I’ll share my email for updates. Let’s schedule a follow-up session to refine your resume. Keep me posted.

Candidate: Thank you. I’ll stay in touch.

The candidate’s journey underscores the value of patience, networking, and practical experience when re-entering the workforce after a career transition. Check our previous blog on crafting a standout resume and LinkedIn presence for more tips.

Re-Entering the Workforce After a Career Break: Insights from a Career Conversation

Excerpts from the conversation:

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