Self-doubt, rejection, resume gaps: A career coach’s guide to getting back on your feet

A long career break can make the idea of returning to work feel daunting – not just because industries move fast, but because life rarely slows down in the meantime.

That was the reality for Ms Kasthuri Gengadaren, a

mother who stepped away from the workforce for 15 years

to care for her two daughters, then re-entered the workforce – only to be retrenched on the day after her father was diagnosed with cancer.

Even so, she kept going: upskilling, leaning into networks and tapping into support from

Workforce Singapore (WSG)

to find her way back into work again at 50.

She says: “Reaching out to organisations like WSG is important because it is very lonely to look for a job by yourself, and they are there to help you, whether through referrals or looking for jobs that suit you.”

Stories like this also show that a career break does not erase capability. But re-entering the workforce after a break often requires one to reset expectations, seek guidance and build a career plan that fits both ambitions and responsibilities.

Here, a WSG career coach tackles the questions women most commonly ask – and offers honest, practical guidance for making the return to work, on your own terms.

1. How do I prove I am still capable after being out of work for so long?

A common mistake is

over-explaining the gap and underselling what you can do now

. This often comes from self-doubt – worrying that time away has made you less relevant. But employers are thinking about something simpler: Can this person do the job, and how soon can she contribute?

In your resume and interviews, reframe the break as a period of growth: highlight real, transferable skills you gained that match what employers need for the roles you are applying for.

For example, mothers and caregivers coordinating medical appointments, school schedules and household logistics can demonstrate planning and stakeholder management skills. Managing competing family needs and last-minute changes can show the ability to problem-solve, adapt and stay calm under pressure.

If you took on

multiple responsibilities or projects during your break

, present the skills on your CV or during interviews, but organise them around what employers care about: the skills used, the outcomes achieved and how these make you relevant to the role today.

2. There is so much to catch up on – from industry changes to artificial intelligence. How do I prioritise?

Many returning job seekers try to catch up on everything at once, which can be overwhelming. A better approach is to be job-led.

Start with the roles you want, then study their job descriptions. Look for repeated requirements – tools, capabilities, certifications and ways of working. That gives you a clearer picture of what employers are asking for now.

To stay current without overwhelming yourself, be selective: Follow a few industry leaders on LinkedIn, subscribe to one or two key publications, and join relevant communities or webinars where you can both learn and hear what practitioners are actually talking about.

You can tap WSG’s

Volunteer Career Advisors

for practical insights from industry practitioners, and

CareersCompass by MyCareersFuture

to read up on hiring trends and job demand.

WSG’s

CareersFinder

can also help you narrow your career options to make upskilling and reskilling more targeted.

3. Job hunting feels brutal – what is a smart strategy, and how do I handle rejection?

Look for opportunities across multiple channels, such as LinkedIn, job portals, recruiters and company career pages. Network directly with former colleagues, friends, industry contacts or alumni where possible. Many roles are filled through referrals or posted on company sites before they are widely advertised.

Focus on quality over quantity. Apply for roles that fit your skillset, then tailor each application so employers can quickly see the match.

After interviews, send a thank-you note within 24 hours, follow up if the timeline passes, and make one final check-in about two weeks later before moving on.

Emotionally, it helps to

treat rejection as market feedback, not a verdict on your worth

. Set weekly action-based goals so progress is measured beyond offers alone.

If rejection starts to feel personal, or you are applying randomly just to feel productive, that may be a sign to pause briefly and reset. If you are still learning and staying clear on what you want, keep going.

4. Will I need to take a pay cut or a lower role – and how do I plan my way back up?

Some women return to similar roles and salaries, while others may need to adjust expectations after a long break. It helps to see your first job back as a re-entry step, not your final destination.

A lower package may be worth considering in the short term if the role offers skills, exposure or a clearer path back to your desired level. In fast-changing fields, you may need to refresh your skills before earning what you previously did.

Contract roles and internships can also be useful stepping stones. During interviews, ask tactfully about scope, ownership and how the work supports the business.

It also helps to understand why a role is contract-based, as this can give you a better sense of whether it may convert.

5. I am worried I cannot cope with family commitments – how do I return to work without burning out or letting anyone down?

This is one of the most common and valid concerns. Many women returning to work are not only thinking about employability, but whether the move is sustainable for their family and mental well-being.

A good return-to-work plan should cover both career decisions and personal commitments – including childcare or caregiving arrangements, flexibility needs and your personal capacity.

When discussing flexibility, job seekers do not need to sound apologetic. It is more effective to frame requests professionally.

Show that you have thought through your arrangements, understand the role’s demands and are committed to delivering results. Employers are often more receptive when flexibility is presented with clarity and responsibility.

Returning to work can also bring emotional friction at home and at work, especially in the early months. Setting boundaries early – around work hours, availability and recovery time – can help prevent burnout.

From a career perspective, WSG programmes and services can support women through this transition in practical ways, from career coaching and job search strategy to guidance on role fit, confidence and return-to-work planning.

The goal is not just to land any job, but to make a return that is workable and sustainable.

Returning to work after a career break? Explore WSG’s herCareer initiative for support, from career coaching to interview training, to help you plan your next step.