4 Steps to On-Ramp Back Into the Job Search After Taking a Career Break

Feb 13

Episode 441 | Author: Emilie Aries

Start your next career search strong, even if it’s been a while.

In a recent Office Hours, the live call I host monthly for members of the HIRED Job Search Accelerator community, a participant posed a very important and relevant question: how do I get back into the job search after years away?

Whether you have been caring for an elderly loved one, raising your kids, or are back from a stint traveling the world, chances are you’ve wondered the same thing. In this episode, I share four steps to help get you prepared and feeling confident when you’re gearing up to launch back into the job search melee.

#1: Job searches take longer these days

If you can, start preparing for your re-entry as early as you can. In addition to the mental prep inherent in any big life transition, studies are suggesting the job search timeline has stretched in a big way.

I talk more about this in my recent episode on dealing with low-ball job offers, but suffice it to say that the average job search is taking 6 to 12 months nowadays, and searchers can expect to send out up to 100 applications within that time. The hiring process has become overwhelming for employers and applicants alike, so it’s best to plan ahead!

#2 Get the first one out of the way

You’ve probably experienced the freeze response that sets in when you start overthinking something important, like a cover letter or a resume rehash. To get past job search paralysis, you just need to get that first application out the door.

Draft your first-and-therefore-worst cover letter (and sure, use AI if it helps you get going), tweak your resume, and then send them off without overthinking it. Don’t expect a response—it likely wasn’t perfect, and also, see the stats from point #1—but usually, that release will lift the floodgates and you’ll feel much more capable tackling the next (and next, and next) application.

#3 Leverage your network

You still have a network, even if your primary social outlet for the past five years has been other full-time caregivers. The people in your orbit don’t have to be high-ranking corporate types and recent coworkers. Think former bosses, university professors, and yes, even your family and friends. Trust me—most people are more than happy to help you however they can, whether that’s making an introduction, practicing for interviews, reviewing your resume, or listening to you vent about how many applications you’ve already shipped.

If you still feel like your network is too small, now’s the time to start rebuilding it. My recent episode is chock full of tips for authentically expanding your professional relationships, too!

#4 Get your story straight

“So, what have you been doing for the last [2/5/12] years?”

This looming question might be contributing to the knot in your stomach when you think of re-entering the job market. Even though there is absolutely no shame in taking time away from your career for literally any reason, we know our capitalist society doesn’t always see it like that. It grossly undervalues care work and departures of any kind from the grind and hustle of the 9 to 5. Women bear the brunt of this because we’re the ones most often accepting (or being thrust into) these alternative roles.

Practice your response to this inquiry ahead of time, so you aren’t caught off guard when it inevitably comes up in your interviews. Remember: you are not required to offer any kind of explanation—and certainly no excuses or apologies—for your time away. However, this is your chance to control which box they place you in, right off the bat, so figure out what you want to say and internalize it. Say it in the mirror, tell it to your partner, and regale your friends with it over coffee.

Here’s how I’d recommend approaching this one:

Lean into your agency. Take responsibility for the decision to “prioritize your health” or “take on the care of a loved one”. Note the reason, then move right along.
Lead with your strengths. How much experience do you have in the type of role you’re interviewing for? When you got that experience is beside the point. If you were in project management 15 years ago, you have a ton to offer to a present-day PM position, too.
Focus on the future. Don’t dwell on the past. Segue smoothly into how your experience makes you a great fit for this role and how much you’re looking forward to the opportunity.

Transitions are always scary and come with a ton of moving parts. Recognizing this and diving into these aspects as soon as you start pondering your re-entry is the best way to keep it manageable, even if the final goal takes a while to achieve.

Do you know someone preparing to dive back in? Share this episode with them, as well as the one where I chat about marketing yourself after a career break with Kelley Biskupiak and Susan Rietano Davey, the co-founders of Prepare to Launch U, which provides “instruction, inspiration, and community to women navigating work–life transitions along the continuum of life.”

My LinkedIn Learning course, Career Strategies for Women Re-Entering the Workforce, is another great resource if you’re on this life trajectory. It’s full of step-by-step guidance on identifying your skills, crafting that explanation, and figuring out what type of work is the best fit for you.

ACCESS CAREER STRATEGIES FOR WOMEN RE-ENTERING THE WORKFORCE ON LINKEDIN LEARNING NOW:

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EMILIE: Hey, and welcome to the Bossed Up podcast, episode 441. I'm your host, Emilie Aries, the founder and CEO of Bossed Up, and today we're talking all about how to on ramp back into the job search after taking a career break.
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This episode is inspired by one of our hired members who joined me for a recent office hours conversation. I host a monthly live group coaching call called Hired Office Hours for all of our hired job search accelerator members. You can learn more and gain instant access to my hired job search accelerator, which is a video based course helping you navigate the modern job search at bossedup.org/gethired recently on our last office hours call, one of our members mentioned that she hadn't really been job searching for the past two years because, in fact, she had an unforeseeable circumstance that involved becoming a full time caretaker. Not an easy job by any means, but one that our society as a whole, does not value or compensate anyone for.
So after two years of serving in this role, feeling like she's lost herself in this role, and feeling like she's really in a vulnerable position financially and professionally, she was asking a big question of how do I even begin to get back in the saddle? And the first thing I said to her and want to say to anyone listening to this is, this is not your fault, right? Like, the reason any person, but particularly women, find themselves having to provide full time care in an uncompensated form to loved ones is due to a systemic failure in our country and in our world. This is a result of not having a proper care economy. We don't have a lot of options. And in fact, our capitalist society runs on the backs of predominantly women, unpaid caregivers who provide a valuable service that is not even quantified in our GDP or in our economy whatsoever. So the first thing to note here is, if you're feeling behind, do not allow this systemic failure to make you feel like a personal failure. This is not your fault. That being said, I want to get straight down to it with four specific steps that I would think about when re approaching the job search after some time away from the paid workforce.
My first piece of advice is to start before you're ready. I was so delighted that this member joined our office hours call about two to three months before she was looking to start a job. The fact of the matter is, the modern job search takes longer than it used to, Randstad found back in the pre pandemic days so 2019, that it took the average job seeker five months to land their next position, and I guarantee you that duration has only increased. Recent studies post 2022 have found that job seekers today are sometimes submitting up to 100 applications before sealing the deal. The fact of the matter is, this process is overwhelming for both employees and employers, and the hiring process today just takes longer than it used to. Not always, but often. So start before you're ready.
My second piece of advice is to just get that first application out, get it under your belt, because the first is the worst. You might be overthinking your resume, wrestling with every single word in your cover letter. Just get what writer Anne Lamott calls your sh** first draft out the door. Right, the first is the worst. Rip that bandaid off, get the first one under your belt, and I guarantee you, you'll get a little hit of dopamine. You'll have the progress principle, creating a little sensation of momentum that will propel you forward. And once you get that first one out the door with, by the way, zero expectations. Right, like, you send that out, you don't expect anything will come from it. If something does, wonderful. It's a happy, great bit of news. But just get that first one out the door, and you'll prevent yourself from overthinking and ruminating to the point of inaction and familiarize yourself with what's changed about the job search today. Get it done and you will feel so much better for it. And then iterate as you see fit.
My third piece of advice is to leverage your network. Now, I know what you're thinking. You're thinking, Emilie, I've been out of the workforce for 2, 5, 10 years. I don't have a network. To which I say, bullsh**, we all have networks. Maybe it's the other parents at the school drop off line. Maybe it's the other caregivers that you met in the hospital while caring for an aging parent, right? Maybe it's that boss that you worked for who you really admired 20 years ago, or that professor who your child had in college a few years ago. You can think broadly about your network, including your personal network. If you feel like you don't have a robust professional network.
Our personal relationships can and should be leveraged. Ask for help wherever you can get it, and people are more likely than you think to want to support you in navigating this transition. It is a vulnerable and courageous act to ask for the help you need from your network, even if it's just someone to bounce ideas off of, or someone to get another pair of eyes on a cover letter, or resume, ask so that others in your life can show up for you. And remember, even if you don't have a very robust network today, you can always grow your professional network. Just listen back to episode 435, Grow Your Professional Network in the new year for practical tips for how to expand your reach and establish new relationships that you can then leverage in service of this transition.
My fourth and final piece of advice is arguably the hardest, but it's the most important. Before you find yourself sitting down for an interview, or even really growing your relationships and growing your network through informational interviews, you're going to want to practice getting your story straight. Here's what I mean when explaining a career break. We have to be able to concisely and strategically communicate what we need to communicate for other people to put us in a box in their mind pretty quickly.
That's the thing about us humans, right? We're constantly jumping to conclusions about people. So you either create the conclusions that folks will jump to, or you are subjected to their unconscious biases and leave it up to chance. When you're up against something like taking a career break, it can feel like a very vulnerable experience because we know that our capitalist economy doesn't value things like caretaking or taking time off to be a full time parent or taking time off to travel the world is even something that raises a few eyebrows in certain circles today.
So while it's truly none of their business why you were out of the paid workforce, we need to get our story clear so that people can trust our motivations and can understand where we're coming from. I recommend being as honest as you feel like you have to be. We're not saying to lie here by any means, but you don't need to be specific either. You don't need to be too detailed. You can say after taking some time out of the workforce to provide care full time for a loved one, comma, and then move the hell on, right like that. Is all the explanation necessary. You do not need to trauma dump on them. You do not need to explain yourself or over explain yourself. And most importantly, do not apologize. Do not apologize or victimize yourself as though you had no agency in the matter and this was a terrible life circumstance that you were just subjected to. I want you to really lean into your agency here and say I made the conscious choice whether or not you did. I made the conscious choice to step out of the workforce, to prioritize my health, to provide care for my family members for the last two years. And now I'm really excited to be back in the arena when it comes to financial advising or whatever it is that you're jumping back into. So be honest, but not too specific. Don't apologize.
And then I would lead with your strengths and focus on the future. You know, I have a 20 year background in providing effective customer service in a variety of different industries and roles, so I'm really excited about the potential for me to be successful in this role, and I'd love to walk through how my past experiences connect to what you're looking for in this capacity. You are moving the conversation on. That's why it's so critical to practice this. You want to be able to concisely pivot from what the hell have you been doing for the past x years to your vision for yourself and the future of your value that you're bringing to the organization in this role.
Now, when you're connecting your past experiences to your potential for success in this role, think about what's most relevant, not necessarily what's most recent. So maybe in recent years you've served in a volunteer capacity on the parent teacher organization at your kids school, and you've got lots of labor that you've performed there, events that you've planned, money you've raised, and that's all relevant and good and sure, put that on your resume to explain that over the past ten years, while you've been raising children full time, you've been also engaging in you know, valuable, in addition to, I should say, caretaking responsibilities, other valuable roles that you've played in your community. That's all great, but if you're applying for a program management job and the experience that you had most recently has nothing to do with program management, but the experiences that you had 20 years ago does. By all means, please focus on the experience from 20 years ago. You might not want to emphasize that it's from 20 years ago, but you might want to speak with confidence about how your most relevant, not your most recent experience has prepared you to excel in this position moving forward. So don't be beholden by chronological order in your life. Okay? Give me the highlight reel and connect your past, even if it's your distant past, to your future in this role.
For more on how to effectively market yourself in the job search after taking a career break, check out episode 202 with Kelly and Susan, the co-founders of Prepare to Launch U, a learning company that provides instruction, inspiration, and community to women who are navigating work life transitions along the continuum of life. It was a great conversation we had a few years back on how to do just that and how to do so with confidence and community by your side. Oh, and if you're the kind of person who really likes learning via video course, I have a great LinkedIn learning course about this very topic It's called Career Strategies for Women Re-entering the Workforce, and you can find it in the link in today's show notes or on, um, linkedinlearning.com. Just search my name, Emilie Aries, for all of my courses there. But this one is especially relevant if you're re-entering the workforce after a career break. If this conversation resonated with you, share today's episode with the folks in your world who you think could use it.
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You can find a fully written out blog post and transcript of today's episode at bossedup.org/episode441. That's bossedup.org/episode441. And until next time, let's keep bossin’ in pursuit of our purpose and together let's lift as we climb.
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