issue #199 - the re-entry issue

Julia & Jessica on returning to work

There are a number of reasons why you might pause and re-enter the workforce. Returning to work can be challenging and often comes with stigma (both internal and external), and it’s a frequent question asked in our weekly AMA sessions. I’ve tapped two of our contributors - Julia Lynch and Dr. Jessica Wilen - to share their wise advice on returning to work with clarity and confidence.

First of all, extend yourself some grace. Understandably, I’ve found that those re-entering the workforce harbor a ton of anxiety around their pivot.

It can be scary. But approaching re-entry from a place of confidence rather than fear will help you immensely—and get you closer to your ideal role.

As you walk through the re-entry process, repeat the following two mantras.

1) I have a rich skillset with a lot to offer a future employer.
2) My institutional knowledge, connections, and work ethic were not diminished by my time off.

Keep that grounding language in the back of your mind as you network and tackle applications.

Now, let’s get tactical.

1) Define what success looks like to you. Taking a career pause often coincides with major life moments. You may have become a new parent, endured health challenges, or dealt with family struggles. No matter the situation at hand, it’s an opportunity to think about your ideal day-to-day. Do you want the flexibility of a 100% remote role? Do you want to pivot from being a manager to an individual contributor? Is a non-partner or non- leadership role the best fit for this stage of life? These are all key questions to consider as you move through the re-entry process. Only you can define success—and once you map out exactly the kind of flexibility and role structure you crave, you can approach your re-entry with more certainty.
2) Network, network, network. I scream this from the rooftops to all of my clients, but networking is an absolute must. While job boards with flexible, remote-first positions exist (Mother Untitled and The Mom Project are two great ones), the vast majority of my clients have found flexible positions through sheer networking. Reach out to old contacts, join digital networking groups, and be shameless about your re-entry with your inner circle—because you never know where your next opportunity will come from. In terms of digital networking groups, Each is Every, Old Girls Club, and Ladies Get Paid are three fantastic groups that are under $100 per year to join. Local Facebook groups are also a minefield for connections, even if they’re not specifically career-focused.

A sample template you can use to network in groups (edit to reflect your own career journey):

Hi everyone! My name is Phoebe, and I’m a strategy consultant with 10+ years of experience at Accenture within their cybersecurity practice. My clients have spanned the Fortune 500 and the federal government—and I’ve helped them create scalable, cost-effective cybersecurity solutions that immediately drive change.

I spent the last four years as a full-time parent, and as I re-enter the workforce, I’m looking to bring my cyber and strategy skillset to another firm.

Does anyone work in the cyber space and would be willing to chat about their role / company? I would be so grateful!

Above all, repeat step one—extend yourself some grace. After a career pause, finding the exact right fit will take some time—even if you’re networking extensively and have the best resume in town. It’s going to happen for you!

Lastly, I’m sending love to anyone currently on the job hunt. If you need some extra support / resources, you can find me on Instagram @smarterinasec (where I share about smart things and career tips every day). You can also check out my website if you’re in need of more one-to- one support.


There are several ways to think about this question, but I’m going to take more of a psychological perspective, instead of a logistical one.

First things first, get clear on your values

I start every coaching engagement by asking clients to reflect on their values. Why? Because research shows—time and time again—that people are happiest when they feel their personal values are aligned with their job. And, anecdotally, I’ve found that most cases on burnout are rooted in a disconnect in personal and organizational values. 

So, ask yourself: “What is at the heart of who I am? What do I stand for? Who do I strive to be?” Values should be relatively stable across your life and transferable across domains (home, work, community, etc.). Once you have your list, take some time to briefly define what these words mean to you.

Examples include:

Autonomy: I value the ability to act independently and make decisions on my own behalf.

Connection: It is important for me to cultivate meaningful relationships with others.

Excellence: I take pride in a job well done; I set high standards for myself and others.

Personal development: I am constantly striving to improve myself and maximize my potential.

Recognition: It’s important that I’m respected and admired for the good work that I’ve done.

Structure your search to maximize values alignment

Now that you’re clear on your values, you can begin to think about fit. Read the organization’s mission statement, scan their website, and even consider talking to current or past employees to try to find out more about the organizational culture (as a proxy for its values). Then, honestly assess whether it’s the right fit for you. For example, if you’re a person who values stability, you may find that being in a fast-paced, high-intensity, “fail fast” type of organization is draining.

Use the interview to probe deeper about organizational culture. Create a list of intentional questions to ask the people interviewing you. I love this list of questions and pulled out a few of my favorite that are specifically focused on organizational culture: 

  • What’s different about working here than anywhere else you’ve worked?

  • What do new employees typically find surprising after they start?

  • Is there anything that I should read before starting that would help me have a shared understanding with my colleagues?

  • How has the company changed since you joined?

Once you have an offer, make sure it’s a good fit

Beyond an alignment in values, I like to tell clients that potential jobs should meet at least two other criteria: 1. Do you have something to offer in this position? 2. Do you have something to learn in this position? Essentially, there must be a clear “value add” for both of you. 

When you’re confident that a job is a good fit, consider negotiating for things that will make you happy and prevent burnout long-term. For example, would you like to work from home two days a week? If the salary offer is lower than you hoped for, perhaps they can compensate by allowing you to only work half-days on Friday? Think broadly and creatively, and then advocate accordingly. Good luck!

"Advice for getting back to the workforce after a 2-year career break?"

“Ditto” to everything I said above. But also…

I might be making an assumption, but I’m wondering if your 2-year career pause was related to caregiving work (either for a baby/young child or an aging parent). If this is the case, I would encourage you to reflect about what you’ve learned during this period—because even though you were out of the paid workforce, you undoubtedly learned important lessons and developed useful skills during this time.

Harvard Business Review recently published a study on the unique value that caregiver employees bring to their organizations. Through the course of their survey, the  authors found that employees who provided unpaid care to a loved one described improved management skills that fell into three broad categories: humanity (empathy, teamwork, and emotional intelligence), productivity (efficiency, persistence, patience), and cognitivity, a term they used to describe “the wide range of mental and emotional work necessary for the organization to maintain culture, connect people, and ensure smooth operations” (prioritization, anticipating needs, and multitasking).

Reflecting on these skills can help you synthesize all that you’ve learned during your career break and increase your confidence as you start the search. Plus, you may even have the opportunity to highlight some of these skills during your interviews.

Jessica’s newsletter, A Cup Of Ambition, is an excellent resource for the work-life juggle. She also offers coaching, if you’re looking for 1:1 support.

Smart Snacks

I’ve been on the hunt for a cricket vest and this one is perfect (and on sale!) - good things happen in Philadelphia (go Birds!) - this facial tool does it all, but the facial massage & heat/cold therapy is especially amazing for my migraine and TMJ friends - if you love Christmas movies, you’ll want to bookmark this - headed to DC this week and am nerdishly excited to stay at this hotel - how to remember people’s names - these bras are the best (and this tape keeps the cups in place without stitching) - the quiet powerhouses behind the Kardashian retail empire - these chips have the flavor of Doritos, the heft/texture of Siete, and 20 grams of protein

What We Read This Week

The Shadow Cabinet by Juno Dawson - this is the best witchy series I’ve read in ages, and the sequel to the stellar first book exceeded by already high expectations. What I love about Dawson’s writing is how humanely complex every character is - even the supposed villans (and they are pretty despicable, to be sure). Like HRMC, this book ends on an insane cliffhanger that has me stalking Dawson’s social media for news about the third and final book in the trilogy.

The Unmaking of June Farrow by Adrienne Young - June Farrow is in her early 30s, taking care of her grandmother as she suffers from an illness that has plagued all the women of the Farrow family - a kind of madness. But June has been hiding the symptoms of the same madness for nearly a year now.
this book is very ethereal. If this were a movie there would be a lot of soft focus imagery
set in a fictional rural town North Carolina
go into it blind, it’s better that way

Lovelight Farms by B.K. Borison - A very cute Holiday story where a woman decides to fake date her best friend in an attempt to win a contest to save her Christmas Tree farm!! I listened to this as an audiobook but I think this may be one that’s better to read.
set on a Christmas tree farm
friends to fake dating lovers
most of this book is from her POV
all the cozy vibes
🌶️: a little

Please Don't Go, Girl by Naima Simone - This is book 3 in a novella series, and you don't need to read them in order, but all 3 books are under 150 pages, so they're all quick reads. I started this whole series just to get to this book and it didn’t disappoint - this one is about the drummer in a band and a school librarian who fake date (for romance reasons) and I want SO MUCH MORE of Lena and Kade! Naima Simone is an absolute MASTER of her craft.
rockstar-normie romance
fake dating
🌶️: obviously yes.

This Week’s Tops Reads:

The Rest of This Week’s Reads:

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Things I Shared This Week

Follow me on Instagram for tips and general musings, on LinkedIn for professional advice (thanks to Break An Egg - a great content prompt newsletter), and on Twitter for mostly Philadelphia Eagles and politics posts and reshares.

I want to conclude Jessica and Julia’s advice with holding space for pauses - the micro-pauses in our day that help us recharge, the longer pauses in the form of vacations and unplugged weekends, and pauses we take in our career to care for others and ourselves.

Rest is not something we need to earn, though society and our own internalized narratives leave us feeling this way. Consider this your permission slip to take a break and do something restful and enjoyable for yourself.


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