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Time Out and Time Off: How to Transition Back to Work from a Leave of Absence

Four creatives share lessons learned during time off and insights for a successful transition back.

As I typed “leave of absence from work for…” into the Google search bar, a variety of scenarios popped up: mental health, stress, surgery, school, family reasons, medical reasons, pregnancy, and so on. During our careers, most of us will elect or be required to take time off work. The reasons vary. According to Pew Research Center, about one in four U.S. workers have taken leave to care for a seriously ill family member. In the UK, stress, anxiety, and depression now account for half of all workplace illness absences. Depending on the country you reside in, you might — or might not — take substantial parental leave after the birth or adoption of a child. What happens when we take time off and how can we best prepare to return to work? I spoke to four creatives about what they wished they’d known and what helped them transition back to work.  


Take care of yourself first. 

Canadian designer and illustrator Darren Booth, was forced to drastically cut back on work after suffering from recurring migraines, which led to a mild depression. At first, he tried to work through the pain, but his migraines worsened. He says he felt down and would cry for no reason. Knowing he needed help, he worked with his family doctor for a year, trying different pain medications and antidepressants. Finally, he found relief when he saw a neurologist who discovered pinched nerves in his neck. With chiropractic care and anti-inflammatory medication, his migraines disappeared after several months of treatment. 

Now completely off medication and back to work, Darren’s health issues helped him re-evaluate his career. He made a decision to prioritize health: “Nowadays, I take care of my health first and the rest seems to fall into place. Home life is better. Work is better. Life in general is better. Although I’m still in the same career, my focus has shifted to growing my work in ways that make me happy and only taking on client projects that I’m excited about. Maybe I earn a bit less, but I can provide so much better now.”

google search results for "back to work"

Just try googling “leave of absence from work.”

It’s okay to not be okay. 

In 2016, after a sudden, severe allergic reaction to corn at the age of 30, writer and therapist Kate Aldridge went into anaphylactic shock and went to the ER. She reflects on her journey, “I was working 50+ hours a week and had to go on FMLA. I quit my job because of malnutrition due to not knowing what I could eat. That’s when I transitioned to a private therapy practice and slowly grew a caseload to accommodate my medical condition.” 

“Once I accepted the fact that I wasn’t okay, that was the first step in turning the corner.” 

Kate used the time off to sleep, recover, and plan the next stage of her career. That’s also when she began to develop her creative writing business. Writing gave her an opportunity to process her situation and ask questions. Now, it’s part of her business and her first manuscript is being published this November. As Kate builds a new chapter of her career, she says what she wished she’d known: “It’s okay to freak out. It’s okay to be scared. It’s okay to feel the things you’re feeling. Give yourself time to process.”  

Be open to change. 

For London-based designer and educator Silvia Grimaldi, both of her leaves from work were planned as she grew her family. She took twelve months off with her first child and nine with her second. Of her first, she recalls, “I was always a lecturer, but before my leave I was teaching in a university outside of London and commuting. That was no longer practical. I desperately needed to return to work to avoid bankruptcy. It dawned on me how expensive childcare was going to be, which spurred me to apply for a role as course leader at my current university. I didn’t think I was qualified, but I got it! I returned to a more senior role and earned substantially more.”

“Put value in things that are valuable for your career and the direction you want to go in. Everything else can take a backseat.”

When she transitioned back to work, she changed how she uses her time as well. Incentivized to get her work done to spend more time with family, she says she became better at saying no as well as being strategic about what she takes on: “Culture needs to embrace the idea that women also deserve a career and we’re not just there to do tasks that others find annoying — we’re there to actually grow our own careers.”

Find fulfillment beyond work. 

Another individual who planned time off was Jojo Giltsoff, a former theater producer who moved from Bristol, England, to Brooklyn after her husband agreed to relocate for work. For Jojo, meeting people in New York who didn’t know her meant she wasn’t defined by her past work. Now she employs her experience and skills of collaboration and organizing in her role as Product Manager at Oak Studios

Black and white image of woman looking into camera.

Image courtesy of JoJo Giltsoff.

Back to work, but no longer consumed by it, Jojo reflects, “I’d wanted to work in theater since I was a kid, but it wasn’t fulfilling me as I’d hoped — it took over my life and didn’t pay well. Re-entering work in tech gave me perspective that my self-worth wasn’t tied to a job. Having time off without my work identity allowed to integrate my non-work identity too.” 

Insights for a Successful Transition Back

1. Find support within your community.

Designer & illustrator Darren Booth didn’t feel comfortable sharing his health issues online, but knew several friends in similar situations. He spoke with them one-on-one, which helped normalize his experience: “Once I accepted the fact that I wasn’t okay, that was the first step in turning the corner.” 

2. Create a plan that works for you.

Writer and therapist Kate Aldridge knew she wouldn’t be able to return to her demanding, full-time job after recovering from allergy-related medical issues, “I wasn’t ready to be fully in private practice, but also knew I couldn’t have a regular 40-hour-per-week job.” So she forged a new path. She applied for her license to practice independently and balances that work with her growing creative writing consultancy. 

3. Identify your priorities.

Designer and educator Silvia Grimaldi found clarity on what mattered when returning to work after maternity leave: “Put value in things that are valuable for your career and the direction you want to go in. Everything else can take a backseat.”

4. Phase back in slowly (if possible).

Product manager Jojo Giltsoff did a trial run with Oak Studios and went into it ready to learn. After the two-week contract wrapped, it was clear it was a good fit for everyone and that gave her confidence to really invest in the role. She says, “It was a big, scary leap for me and it felt like I had less pressure to ease in.”

Whatever the reason we take time off, getting back to work requires flexibility, openness, and patience as we move forward into a new season of our careers that may look similar or altogether different. But for many of us, transition will require letting go of our expectations, as Jojo put it: “It was a process of grieving. I don’t know where I’m going to be in ten years and I think that’s great. If I’m still enjoying things and loving what I’m doing, that’s success.” With every transition, we have the opportunity to care for ourselves, reprioritize what matters, recognize opportunities, and even refine our definition of success. 

More Posts by Tina Essmaker

Tina Essmaker is a New York City-based coach, writer, and speaker.

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