Ultimate Guide To Returning To Work After A Career Break

Let’s Get Back To Work

Returning to work after a career break can be a really exciting new chapter in your life. It can also mean that you are entering into a job search that might be challening. If you’re looking for that first job after being out of the workforce for a period of time, you are not a typical job-seeker. Therefore, you should not be conducting a typical job search process that relies mostly on applying to jobs.

As an outside-the-box hire, you’ll need to focus primarily on connecting with people where you’ll have the chance to explain your unique value proposition. Your resume may not tell your whole story, so you’ll need to get out from behind your computer and make personal connections. 

This is an exciting transition in your future. It may seem like a daunting task, both the personal aspects of shifting from being a stay-at-home mom and the fact that your family will also have to adjust to the new order at home. Read on, but also be sure to check out my blog on how to get your job search started.

Let’s walk through the process of restarting your career together.

Find Your Focus As You Return To Work After A Career Break

You’ll want to invest some time before you dive into a job search to find your focus. For some of you with highly specialized skills and a shorter career break, this step might be easy. If your career break has been longer than a few years, you don’t want to return to your previous field, or you simply aren’t sure yet, this is important. It will be critical to take an inventory of your skillset, your interests, and your motivation for returning to work to help you determine your focus.

Start by listing your most job-relevant skills

Don’t limit yourself to skills you have been paid for using. If you’re the volunteer who has raised tons of money for organizations, then fund-raising is a skill you possess, even if you weren’t being paid to do that. 

List soft skills such as leadership, people management, communication and collaboration. Don’t overlook the importance of soft skills in the hiring process, but do be sure you have an example that proves you possess each skill you are listing.

Include your hard skills such as any technical or job-specific skills you have. Don’t edit yourself during this stage, just get all of your skills into a list without worrying about your competency level just yet.

What Interests You?

Next, come up a list of your interests. What do you enjoy doing? Are there things you can completely lose track of time while you’re doing because you enjoy them so much? Consider previous jobs you’ve held – what were the parts of those jobs that really lit you up?

What Motivates You? 

Think about why you are returning to work after your career break and get that down on paper. Do you need to earn income to support yourself or your family? Are you excited by the idea of contributing to a company with a mission you believe in? Do you yearn to put your education and experience to work again and miss the feeling of accomplishment that comes from full-time work? We’ll want to capture your motivation because this might help you decide between jobs down the line.

Every transition or new job involves making trade-offs and you’ll be in a better position to determine if the trade-offs you’re making are ones you can live with if you’re clear on your motivation. For example, if you’re returning to work after a career break for financial reasons, it might make sense for you to pursue higher-paying jobs even if that means you are working longer hours than you’d ideally like.

Add It All Up

Take a good look at your lists of interests, skills, and motivations. What does it tell you? The magic in finding your focus lies in determining where there’s an intersection of your skills and interests with a need in the job market. Start reading your local business press or industry publications/blogs for jobs you are considering. You’ll want to understand where the need in the market is greatest. 

Make A List Of Your Career Break Activities

This can help give you some clues about what you really enjoy doing. It may also provide insight into the skills you’ve developed or sharpened since leaving the paid workforce. I’ve got a whole blog on developing your list of career break activities here.

Focus Doesn’t Mean Just 1

While having direction for your job search is important, at this stage I will encourage you to have multiple paths in mind. Having more than one idea about where you can effectively plug back into the workforce can help you stay flexible. If you’ve determined that your skillset could be applied in a few different contexts in the workforce, then map out these parallel paths for yourself rather than discarding one. Keep in mind, 5 parallel paths may be too many, but 3 could be just the right number.

Prototype Your Job

This next step is fun! Once you’ve found a direction (or two or three), come up with some ways you can prototype this new career for yourself. You’ll want to learn all about it and even try it on if you can. Here are some ways you can do that:

  • Find people doing that job or working in your field and talk to them about it
  • Check YouTube for videos that give you the inside scoop on the job by searching “a day in the life of a (insert profession here)”
  • Read job descriptions for your ideal job to understand the expectations and the requirements 
  • Search for the job titles you’re considering on LinkedIn and read through the career paths of people who are doing that job now to notice how they got there and what their key skills are; connect with them and ask them if they’d speak with you so you could learn more
  • Find LinkedIn groups, MeetUps or professional associations for people in the job you’re considering and join them – sometimes these groups have mentoring opportunities

Prepare Your Family For Your Return To Work

Let’s take a time-out from your job search activities here to think through preparing your family for the changes that will occur when you return to work. It’s never too early to give your crew a heads-up that things are going to be changing around here!

Start shifting responsibility for some of the tasks that you’ve taken on to others in your household. Nobody can do it all, and trying to is a recipe for burnout. If you’ve got kids still at home, remember that they will benefit from the responsibility of being contributing members of the household. Chores are beneficial for kids.

Preparing early for your transition back to work gives you time to conduct that Saturday morning session on how to use the washing machine or how to empty the dishwasher. Be sure to enlist the support of your spouse as well – marriage is a partnership and yours can withstand the redistribution of responsibilities that comes with a spouse returning to work after a career break. 

Make a Target Company List

You probably thought the next step was going to be applying to jobs. But I’d rather orient your job search around specific companies where you’d like to work and the people who work there, rather than just let you loose to flood the internet with blind job applications that you’ll never get a response from.

Brainstorm a list of companies that you’re interested in. Then build on your list by searching  LinkedIn for them and noticing which companies pop up in the right sidebar labeled “People Also Viewed”. These are companies that are similar to the company you searched on and you may not have heard of them – wonderful! You are broadening your horizons! For additional ideas, be sure to check those famous lists such as Fortune’s Best Places to Work list.

Find People To Talk To As You Return To Work After a Career Break

Now that you’ve got a list of companies you’re interested in, the next step is to research them and find people who work there. Tap your own network and ask people if they know anyone at your target companies they can introduce you to. Getting a warm introduction to someone is much better than doing cold outreach, so lean heavily on your network in this stage. Remember, you are in information-gathering mode, so you’re hoping to speak with people who can share their experience with the company and provide insight into where they might be hiring.

If you’re coming up empty, go back to LinkedIn and search on the company using the People filter. Find people who work in the department you’re interested in joining. Or find people in Talent Acquisition and send them a connection request with a very brief personalized note noting your interest in the company and asking if they’d be willing to spend 15 minutes speaking with you about their experience. Then follow this guide to conducting informational interviews to get the most out of your meeting.

This step is tricky, because to be completely honest, you are not going to get a lot of people who are willing to chat with a total stranger. Don’t take silence or rejection personally, just keep plowing ahead. These conversations and connections can be so valuable for a job-seeker that it’s worth making the ask even if only a very small percentage of your requests receive favorable responses. 

OK, Now Apply!

You’ve gotten clear on your direction(s) for your job search, put together a company list and talked to people in your field. I know you have learned a lot and made some good connections, and now it’s time to apply to jobs.

Set up job alerts in LinkedIn and Indeed and make sure your profile is built out completely on both of these sites. Let’s make it as easy as possible for recruiters to find you! Be sure you’ve set up alerts for multiple variations of the job title you’re interested in to increase your chances of getting sent the right jobs. 

Write a cover letter that speaks to your interest in the job and is personal. Nobody likes getting a form letter, so use your research to make sure your cover letter is targeted for the job at hand. Customize your resume also – it should mirror the language of the job description you are applying to in order to increase your chances of being noticed. Pro tip: ChatGPT writes a good cover letter in just a few seconds!

Get That Referral

If you’ve got a contact at the company you are applying to, reach out to them before you apply to let them know you’re applying. In the event that the company has a referral system, your contact might be able to give you a special link to use when applying to the job. If you’ve already applied, however, a referral link is unlikely to be valid. Lots of companies pay their employees a bonus for referring candidates who get hired, so if you’re asking for a referral you might be doing both of you a favor!

Now Find An Insider

For those job you applied to through a referral link, you can skip this step. But let’s say you’ve applied to a job and you don’t know anyone at the company but you’d really like to get your application noticed. Head back over to LinkedIn, find someone who works there in the department you’re applying to and send them a connection request with a message. Your message should say: “I am applying to the Project Manager role in your department and I’m really excited about it because (tell them why you’re going to be able to make a big impact there). I hope to have the opportunity to speak with your team about my interest in this role.”

Note that you’re not asking for anything, just hoping that your expression of interest will help shine a light on your application. This is a step most job-seekers don’t take, which means it’s a real opportunity for you to stand out among the pool of candidates.

Now Do It Again

One of the most frustrating things about applying for jobs is that you simply won’t get any response to many of the applications you put out. Recruiting is a broken system in many organizations, which I think is completely avoidable given our ability to automate tasks. Still, the take-away is that you can’t just apply and then wait around, because you might be waiting forever. 

After you apply and you send your follow-ups via LinkedIn, find more people, more companies and more jobs and repeat the process. I’m not a big fan of applying to a million jobs and thinking that it’s just a numbers game. But the truth is that you have to put yourself out there many times in order to be successful with a job search. This is hard, but it’s going to be worth it when you land that job. And everything worth doing is hard. I know you’re up to the task, though. 

Nothing Is Wasted

In job search, nothing is wasted because everything that happens is an opportunity to learn. Not hearing anything back from your applications? Revisit your resume and the types of jobs you’re applying to and give them a critical look to see what you need to adjust. Having lots of interviews but no offers? Get some coaching on your interview skills and prepare your answers to commonly asked interview questions.

Winging it during interviews is not a set up for success. Ask yourself what you can learn from every step in the job search process, and be flexible enough to pivot when the market is telling you that you need to make adjustments.

Own Your Break

As a non-traditional job-seeker, your difference is your strength. Don’t be afraid to own your career break and talk about what you learned during that time out of the paid workforce that will make you a better employee. Proactively position your career break as a positive thing and control the conversation around it – if you don’t respect your career break, potential employers won’t either. For tips on how to talk about your career break, download my Own Your Career Break Talking Points here.

You Can Return to Work After a Career Break

You aren’t alone as a woman restarting her career. Find a friend who is also returning to work and commit to meeting for coffee once a week to encourage and support each other. Support like that will really keep you going when things get tough and the job search starts to feel long. Just remember that you can totally do this – and I am here rooting for you every step of the way!

Look Behind You

Once you get that job, don’t forget to look behind you and notice the other women who are trying to make this same transition back to work. We need to help each other out and advocate for each other.

Until taking a career break is regarded as a normal part of a long and successful career, we’re going to have to encourage our employers to consider candidates who have non-traditional resumes. Let’s do this together!


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