By: Ann Caskey


Transitions are hard. I tell my kids that all the time but sometimes I have to remind myself too. And the transition back into the workforce is no exception.

I never planned to be a homemaker, but life happened. And by the time child #3 was heading to preschool, I was getting itchy to get back to work. I wanted to use my brain instead of playing Candyland (again), I wanted to be identified as something other than “X’s mom,” and I wanted to know that with all my education and training, I could be independent if I ever needed to be. I had been raised to use my brain, have a heart, and stand on my own two feet, and I needed to know all those parts were still working.

But where do you even start? And what can you expect as you try to reenter that world of work that you left so long ago? I sometimes think about the challenges I faced, and how I tried to overcome them. I don’t pretend to have all the answers but perhaps my experience can help someone else as they start out on that same path.

What do you want? 

I recently heard a graduate recruitment officer advise applicants to research not only their potential employers but also themselves. It’s great advice. Take time to figure out what you want: Money? Responsibility? Social interaction? Travel? Everyone’s goals are different, and yours are different from the person next to you, but maybe also different from the person you were when you left the working world. Listen to that person. One of the biggest advantages of a career break is the maturity and perspective that you can gain. Coming back, maybe you do not have the stars in your eyes that can prevent you from seeing the everyday realities of a job, you know better what you are getting yourself into, and what you want out of it.

One of the harder parts of figuring out what you want is balancing that with what you can realistically have. Everyone has limitations and obstacles so don’t be disheartened but also don’t set yourself up for failure. If you absolutely want to be a lawyer but you don’t have a law license, you have work to do. If you want to be a transatlantic air steward, you have to be prepared to spend nights away from home. If you have your heart set on being an astronaut, you’re unlikely to be able to work remotely. Everyone has to make choices. Find what works for you.

Updating your skillset

Even a short career break can impact your knowledge base and skillset but there are lots of opportunities to get up to date, from in-person and online courses to programs specifically intended for people returning after a career break. Some larger companies even offer internship opportunities for returnees. Depending on your field, you may also be able to practice and showcase your skills in another way – design a new website for a friend’s business, run a large event for your child’s school or offer your services to a nonprofit. Any real-world experience counts.

When I was planning my reentry, a friend in the industry advised me to get a job first, with the expectation that my employer would pay for some or all of my training. Some employers will support you, financially and otherwise, in your training because everyone benefits. But, if you, like me, did not have enough hours in the day to add in both studying AND a job, find a way to make it work. In my case, I signed up for a part-time, fully remote bar review course and studied every day before my family got up and for the couple of hours that my youngest was at preschool. I passed the New York Bar Exam and went on to do some pro bono work for an immigration organization. Not only did I get an important prerequisite qualification, but I got my brain back in action, and I had something substantive on my C.V. to show potential employers.  

Finding a way in

When you are on the outside, finding your way back into the working world can seem like the biggest obstacle of all. I don’t believe the door looks nearly as narrow from the inside. People are generally very supportive of someone who has made the conscious choice to reenter the workforce and exhibited the drive and dedication needed to do that. 

Just as everyone has different priorities and skills, everyone has a different path back to the workforce. Networking, in person and online (yes, you should be on LinkedIn,) is major. Some people have maintained a strong professional network from their working days. If you are one of these people, use it. Use it for advice, to hear about unposted job vacancies, to learn how the industry may have changed, and to make even more connections.

Perhaps you are breaking into a new industry or a new geographical area, or you simply did not maintain your professional connections. (Let’s face it, some people disappear quickly when you can’t go for Friday night drinks anymore.) If you do not have a professional network, look to the network that you do have. When I wanted to return to work, I was in a completely new city where no one even knew I was a lawyer. I made the conscious choice to chat openly about studying for the bar, which was difficult because I frankly would have preferred to do it all in secret and never have to tell anyone if I failed. I was pleasantly surprised that people were keen to talk about their careers and offer advice: A parent at the playground was a lawyer turned mediator setting up her own firm; a mom at the pool was an internationally qualified lawyer, like me, who shared advice about local LLM courses and paths to U.S. qualification; many of my “mom-friends” were also trying to get back to work pursuing former or new passions and careers. We shared advice, gripes, and lots of coffee. And that is as supportive a network as I will ever find. 

And it was how I connected with Robyn Addis, and reentered the workforce.

Time management

There are 24 hours in a day, and adulting takes more time than I ever knew. When you add a job back into your day, there will inevitably be a time crunch as you try to figure out who will do what and when. Some people choose to outsource some of their tasks to nannies, cleaners, shoppers, or household managers. Some reassign responsibilities in the household, such as giving the kids more chores or alternating the driving to school/soccer/ballet/chess/piano/gymnastics/baseball/[insert myriad kid activities.] Ask your working friends how they do it. Try, without being nosy, to get actual responses beyond the common “you just do it, don’t you?!” or “I’m a hot mess!” Maybe they spend Sunday cooking ahead for the week, get up an hour early to exercise, or hang a huge color-coded calendar on the wall with everyone’s responsibilities. You would be surprised at some of the things that people have figured out to make it work. Get some concrete ideas and figure out what works for you. One friend once asked me:

“If you could outsource one thing, what would it be?”

It was such a great moment of focus for me. Instead of being overwhelmed by ALL THE THINGS, I focused on each task individually, and I constructively considered how I could make it better (or get rid of it altogether.)

Family expectations and guilt

When you go back to work, your household routine and equilibrium will change. Transitions are hard, remember? You and your family may be used to you being available 24/7, but now you have co-workers, clients, and bosses who are relying on you too. Give yourself and your family some grace as you all get used to your new life. Communicate A LOT (no, more than that.) If you have been running the household during your career break, your family probably (1) does not realize all the jobs you do, (2) assumes they will still be done, and (3) does not deserve to get in trouble because they didn’t do it. On the flip side, you should not feel guilty telling your family that these jobs have to be done and they should no longer be your sole responsibility. Communicate.

The guilt of returning to work is hard for many parents, whether it happens after 6 weeks after birth or 6 years. When you cannot chaperone a field trip or you are not home when they get out of school, it might sting but you will get through it. Some people even find that this creates space for a spouse to become more involved or for kids to learn more responsibility and independence (“No, I can’t bring your Chromebook to school again. You should have remembered it.”)

With all the time pressure and the guilt, some people find it practically and emotionally difficult to carve out time for themselves when they return to work. There is a danger, especially for part-time, flexible, or remote workers, that your work time becomes your “me-time.” It is not. Everyone needs to make time for physical and mental wellness, whether that is Zumba, yoga, walks with friends, meditation, or all of the above. And if you are like me, your family will thank you for it when you show up a little more Mary Poppins than Wicked Witch of the West.

Reentering the workforce is challenging but it is worth it. I have no regrets about taking time off work for my family, and I am equally glad I went back. I am grateful for the people I have met, the confidence I have gained, and, of course, the money! But I am especially glad that I have had the chance to rediscover the person I was before my career break, figure out the person that I have become, and share that person with my family.

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