The 4 Challenges Parents Face When Re-Entering The Workforce — And How To Tackle Them Head-On

Taffi Dollar
4 min readMay 30, 2019

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Every year, millions of parents who’ve stayed home with their kids for several years make the decision to re-enter the workforce.

It’s an exciting decision, and one that often leads to pleasant surprises. I know when I went back to work — around the time when my children were entering school — I found I had more wisdom than I had at the beginning of my career, and that my life experiences had made me a better employee. Specifically, I found I was a better listener and that I was more understanding. I had more empathy, so I could better discern when the clients, customers, and colleagues with whom I worked with were disgruntled or confused, and I could work more purposefully with them to rectify that.

This, no doubt, was a product of skills I’d honed over years of being a caretaker. It broadens your perspective and enriches your capacity for sensitivity.

Yet, at the same time, re-entering the workforce after a long time off comes with its own unavoidable challenges — especially when your kids are still at home.

Here are a few of the most burdensome, along with how in your day-to-day life you can combat them.

1) You’ll likely find that you sometimes still want to be home.

This was the hardest one for me. I found, when I reverted back to working in an office every day, that as I sat at my desk and glanced for a moment out the window into the street, there felt like an unmistakable need to leave work and go be with my kids. To make sure they were safe. It was a compulsion that felt inherent and undeniable.

All parents feel this, no doubt, especially when your kids are still young and you’re hyper-sensitive about missing their more defining developmental moments.

What helps alleviate this pain inside you — what helps you overcome it so that you can focus 100% on your work when you’re in the office — is establishing expectations with your boss or within the culture of the company. You should have the peace of mind that if an emergency pops up, or if for whatever reason you need to dash home, you have the flexibility to do so.

Additionally, I found that spending time with other women in the office who were also working mothers and experiencing the same things I was proved calming. It made me feel less alone and reiterated the fact that being a working parent was normal. To communicate, relate with others, and work together, in a sense, helped me conquer my guilt.

2) The workforce will likely look very different from when you were last in it.

Technology is evolving faster and faster all the time.

Because of that, it’s only natural to expect that the tools, platforms, and processes with which you were familiar when you last worked will have likely changed somewhat during your time off.

And depending on your industry, those changes might, in fact, be drastic. The expectations for what you as an employee will need to be proficient might strike you as intimidating. There may be expectations that you understand the ins and outs of social media, for example, or that you can use Microsoft Excel.

The key here, if you’re struggling to master your company’s new technical demands, is to surround yourself with people who’ve already achieved that mastery. Then, rid yourself of any hesitancy you might feel about asking them for help and support. You’d be surprised how willing your colleagues are to help.

3) You probably won’t feel rested.

Surprise, surprise: Parenting is tiring work.

Guess what? That doesn’t change when you go back into the office. In fact — another surprise — with your increase in workload, you may be even more tired than before.

If it’s possible for you, it helps immensely to hire someone who can assist you around the home — someone who can help pick up your kids after school, even, can be a big help. It also pays to empower your children with the ability to take on domestic responsibility early. I was surprised, personally, by how even my youngest kids were able to learn how to do their own laundry, prepare their own lunches, and get themselves ready for school each day without my direct oversight.

Whether you’re the CEO of a company or back at entry-level, any little bit of responsibility that you can outsource to your “little” team will go a long way toward alleviating your stress. It might allow you a few more minutes of sleep each night, too.

4) Maintaining work-life balance will be tough.

Finally, we arrive at this unfortunate truth: For female parents who work, especially, the predominant expectation is that you need to be a multitasking superhero who cares for your loved ones and succeeds at the office. In overseeing all the variety of tasks and people we’re responsible for, we’re expected to be mechanical.

Of course, we’re not machines nor superheroes. We’re going to experience anxiety and frustration A) because we’re human, but also because B) working and parenting are both hard work.

It’s important, then, to invest as much as you can into yourself. Don’t be afraid to vent when you need to, or ask for help either at home or at the office when you need it. I know that, for me, this required me to check my pride at the door, so to speak, which was hard, but worth it.

In spite of all I’ve listed out here, though, it’s important to remember that if returning to work is something you want to do, you owe it to yourself to give it a try. And although they can be challenging, the obstacles of returning to the workplace as a parent are not insurmountable.

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Taffi Dollar

Gender strategist, pastor at World Changers Church International, CEO of Arrow Global Entertainment, author, and motivational speaker.