Career Reboot: My Journey Back to the Workforce After an 8-Year Break for CaregivingFeatured

In 2013, working mothers were coached to "Lean In" to their careers. That was the year I chose to lean out. At the time, I was the Director of Hedge Funds for Willett Advisors, the investment office for the personal and philanthropic assets of Michael Bloomberg. I enjoyed the job and the tremendous opportunities that came with it. So it was a surprise to many when I left that job for one with longer hours, no benefits, no pay, more demanding clients, and a much less esteemed job title: stay-at-home mom.

As a new mom in a highly competitive field the choice felt binary: full-speed ahead or slam on the brakes indefinitely. At the time, the path back to the workforce after a career break for caregiving was not well-worn. A step off the career ladder was a precipitous plunge. Extended resume gaps were insurmountable. LinkedIn was still eight years away from releasing a feature that would allow users to even mention this choice on their profile. Formal returnship programs were rare. Despite this, I chose to leave the traditional workforce and “lean in” to the role of full-time caregiver.

I am grateful that I had the choice to be a full-time caregiver. I tried to be present and appreciate everything (including the challenges) that those early years brought. I also accepted that eventually, my days of adventuring through early childhood with my kids would give way to sending them off to school for most of the day. I knew I wanted to return to the workforce when that big yellow bus arrived, and was keenly aware that was going to be an uphill battle.

When students are choosing a career, they’re asked to reflect on what they enjoy doing and what they’re good at. I chose finance because I liked doing math and the jobs were lucrative. Many of us select an industry or role early in our lives and then follow an inertia-driven trajectory despite the fact that our interests, skills, and priorities evolve. Stepping away from the workforce allowed me the opportunity to reexamine my path and be deliberate about why and how I wanted to return to the workforce.

I began crafting a return-to-work strategy long before I was ready to return to work.

The first step was to develop a clear vision of what I wanted: the type of work, the location, and, most importantly, the company culture. I settled on the type of work I’d like to do relatively easily.

Aside from a few Excel macros and Matlab scripts, I had never written a line of code. It was a skill I had a desire to learn but never had the time to pursue.

Early into my career break, I enrolled in MIT's online course Introduction to Computer Science and Programming through the edX platform and worked through the material during my son’s naps. That was the first of many online courses I ended up taking and it solidified my new trajectory. I liked writing code and resolved that was the type of work I’d like to do upon returning to the workforce.

I envisioned working remotely for several reasons related to work-life balance (this was pre-pandemic), but also because we were no longer living in a major metropolitan area.

Finally, I envisioned working for a company that considered the non-linear career path I’d taken through finance and caregiving an asset, not a liability. I recall at one point speaking to a well-intentioned resume expert at a women in tech meet-up who advised me to hide the fact that I had taken a career break for caregiving. I politely responded that if I needed to hide that from a potential employer it probably would not have been a good fit anyway.

With the vision set, the next steps were creating and executing a plan to maximize my odds of realizing that vision. One significant element of this plan was returning to school. I had taken several online courses and explored various programming languages and technologies before zeroing in on artificial intelligence and machine learning.

Formal education might not be for everyone, but based on my goals, it appeared to be the best route for me. My undergraduate degree was in finance and economics, so that journey started with taking computer science prerequisites at a community college and ended with the completion of a Master's in Computer Science focused on AI/ML.

I had the support of my family, but since I was an extreme outlier in my program, it’s hard to put into words how lonely that path was. I didn’t feel like anyone could relate to the unique challenges of context-switching between a rigorous course on the mathematical foundations of machine learning and managing a toddler’s meltdown.

Fortunately, I did eventually find people who could relate to those challenges through the other significant element of my plan: cultivating a network. Organizations dedicated to supporting caregivers returning to the workforce, specifically Path Forward, Women Back to Work, and iRelaunch, were an invaluable part of my return-to-work journey.

Connecting with and hearing the stories of others who had successfully relaunched careers after 2, 12, or 20+ years out of the traditional workforce was inspiring. Seeing companies eager to hire returners, specifically those with relevant technical skills validated the educational path I had chosen. I also came to appreciate how the non-technical, soft skills I had gained during my years as a stay-at-home mom could translate into valuable skills in the workplace. I was more patient and organized. I was more generous with praise and direct with feedback. I had a better appreciation for how we all learn in different ways and at different paces.

I returned to the workforce in 2021, as a Lead Data Scientist at Stanley Black & Decker through a "returnship" facilitated by Path Forward.

My advice to anyone who wants to relaunch their career or pivot, is to start by envisioning the end goal. Ask yourself, what skills do you need to do that job?

Starting at the finish line and working backward can help you develop and execute a plan of action. Conducting this process demonstrates to employers that you have the relevant, in-demand skills required for the job you want. It also signals you have the discipline necessary to continue to upskill as that set of in-demand skills evolves. Your career doesn't have to be a linear climb upward. It can ebb and flow in response to your other priorities. However, setting yourself up for long-term success requires being intentional about what you want to do next and the specific steps you need to take to put yourself in a position to achieve it. Then surround yourself with people who understand the path and can help you navigate the road it takes to get you there.

Today, I am a Machine Learning Engineer at Pluralsight, a company whose mission is advancing the world's technology force. My path to tech has come full circle, leading to a job that empowers others to acquire technical skills. It is uncanny how closely my current situation resembles the picture I envisioned many years ago when I was in the earliest stages of planning a return to the workforce.

There is a lot of discussion across the industry about how to improve the diversity of our technical workforce. I recall many times during my career break, feeling like the effort I was putting in would be a waste. No one, especially in tech, would ever want to hire someone with my unconventional background. In reality, companies can improve the diversity of their workforce by casting a wider net and opening the top of the recruiting funnel to non-traditional candidates. Companies that value diverse life choices and experiences will inevitably benefit from the varied perspectives and skills these candidates bring to a team.

Last year, a friend in Silicon Valley texted after seeing the update to my LinkedIn profile announcing my new role at Pluralsight. He wrote, "Congrats on the new job! You have willed your way into a career in tech".

Wonderful post. Returning after an absence is such an important topic. Your post does a great job showing "It is possible."Bravo!
What a beautiful jorney! So proud of you and thank you for sharing this!
Thank you for sharing your journey! I resonated with so many things you said as we had very similar paths!
Fantastic and well-written post! Thank you for sharing your journey and articulating it so clearly! How did you manage going back to school and taking care of young kids? Did you do a part-time or remote program?
Yes, I was part-time! I was in-person and took most of my classes at night or lined up classes for when my kids were at preschool, since finding part-time babysitters during the day is very difficult.
Wow, that is amazing!
Thank you for this post! I love that you took that time to re-evaluate and head back to corporate with a new vision and a refreshed mission. I am also a returner and struggled to get a foot in the door upon return. Unlike you, though, I wanted to go back to what I was doing before and was out of options for formal education reboot (I already had a PhD). One afternoon during my search I went to a women in tech virtual event and mentioned my issue in the chat. That was when someone said the magic word, “Returnship”.Returnship programs are a game changer and rocketed me back into my career. Granted I did start back in a lower position than I left (that was anticipated), but with a promotion year over year, I am close to being back at my pre-break level. My company was so supportive in those first six-months of getting my footing and I now mentor other women going through Returnship programs.
Congratulations on reaching the destination and sharing the journey with us! I hope you continue to share more tidbits on how your got through the tough days and balancing the career to-dos with kiddos.
Wishing you great success on your journey! You're doing great!
Thanks for sharing your story and resources. Such an inspiration. I'm working on my return to work now. It's been 15 years. This post is just what I needed.