How to take a career break — Jocelyn Caithness

Featuring Justine Chiu, Photographer, Content Creator, and Freelance Software Developer who believes in making the web more accessible for everyone :)

I can hardly believe I’m writing this, but as of 2023 it has been ten years since I graduated from university, and 9 years since I started my corporate career.

Like many of my thirty-something peers, I’m starting to re-evaluate what success looks like to me, and how my career plays a part. I think the combination of trying to overachieve for too many consecutive years coupled with the cataclysmic realizations the pandemic brought on, has left us asking “Do I really want to do this for the next thirty years?”.

Some of us are still grappling with the question, but others have already adjusted their lives to pivot or change direction.

One of these people is my friend Justine, who I admire and look up to very much. She’s navigated a lot of change in recent years, both personally and professionally, and I think we could all learn a lot from her :)

I wanted to share more about her recent decision to take a career break – leaving a comfortable corporate career with a likely upward trajectory – to focus on her interests and go freelance.

I had a lovely conversation with Justine in which she explained how she took the steps to make this change, but we also discussed the importance of listening to that inner voice, and why taking a career break should be seen as a milestone – one worth celebrating as much as getting married, having kids, or buying a house!

Read on to for more of our conversation:

We’re basically a decade into our careers now! Can you walk me through what’s changed in that time?

Justine told me that she felt like she had a very limited view of what success looked like when she first entered the working world, and that the goal post kept moving every year. When she graduated with her degree in Human Resources, she began her career in that industry…but realized rather quickly that it wasn’t what she had been expecting.

She had assumed that she would stay in HR for her whole career, but the thought of that felt heavy.

Nevertheless, she stayed for several years because she felt like she needed to make the investment in her university degree worthwhile – both to herself and to her parents. This notion helped her get through it, even though she knew what she was doing wasn’t making her happy.

She also started networking with people outside of the HR industry. She felt drawn to those working in the creative field and was exposed to people who really loved their jobs. She began to realize that jobs are like any other relationship – you put work and energy into them, and they should “love you back”, in a manner of speaking. It shouldn’t feel like a one-way relationship where you’re getting nothing in return.

When her friend introduced her to the world of coding, everything changed.

Justine started watching a lot of YouTube and learned more about coding from creators and influencers like Wes Bos and by watching “how to” videos. She knew this was something she enjoyed, and at the same time, she knew she didn’t want to stay in a career that left her feeling so unfulfilled.

It was an honest one-on-one meeting with her manager that eventually helped her make the decision to leave HR. She opened up about how unhappy she was and admitted that she felt stuck in her career because of family and societal pressure. Her manager helped her see her situation for what it was, and after four years sticking it out in HR, she took the leap and enrolled in coding bootcamp.

How did you decide to take the risk and leave your career in HR to go back to school?

Justine didn’t have an epiphany and dance her way out of the office – instead, she carefully assessed the situation and weighed the pros and cons. She was in her mid-20s, didn’t have a mortgage or dependents, and had saved up enough to take the risk that leaving her job would entail financially.

She also knew coding was something she was inherently interested in, because even as a child she was curious about it. It also felt easier to make the leap and go back to school, and a nine-week program felt very doable.

What happened next?

Justine completed the bootcamp and launched a successful career in software development for six years. She was enthused to become the best in her field, but eventually, because she felt like this was her “second chance”, she put a lot of pressure on herself to make it work no matter what.

The fact that she had already pivoted once in her career led her to feel as if she couldn’t course correct again – and that led to burnout.

But Justine knew herself better this time around and realized that she needed to hit the pause button before that burnout got any worse.

The first time she pivoted, her inner voice was struggling with the feeling of “I don’t know what I want to do with my life”, but the second time it was “I don’t know why I want to do this”.

How has your career break turned out so far?

It was hard at first for Justine to have taken another leap into the unknown – she talked about the guilt she felt about being burnt out, and the guilt that accompanied the decision to leave her comfortable career during an unstable economy. But ultimately, she knew she would learn from this decision and that it would be worth it.

After about a month, she realized she was going to be ok. She put the wheels in motion to do freelance jobs, and the work started rolling in. In fact, more opportunities have arisen than she can take on and she’s had to actually turn down jobs. The universe is funny that way :)

The key, she feels, was to get really crystal clear on what she wanted to do next.

Once she made the decision to take a break from her traditionally corporate career, she knew that she wanted the next chapter of her life to be about web accessibility. Like kismet, an opportunity to coach other software developers about software accessibility fell into her lap.

She notes that after knowing what you want, it’s important to talk about it out loud to other people. It plants a seed in their minds and – even if it’s subconsciously – there will be a network of those who support you keeping their eyes and ears open for opportunities.

Another habit that Justine found helpful for gaining clarity was writing. She wrote not just about what tasks or responsibilities she likes and dislikes, but the feelings (ex. “I don’t want to feel like I have no breaks in between meetings”, “I don’t want to feel like I have to do the same thing over and over”). She would also revisit these thoughts and continue to check in to make sure there was still alignment between that inner voice and what her life looked like.

Has it been difficult to adjust to this new way of life after being in the corporate world for so long?

Justine shared that taking a career break has left her feeling a little more isolated, since she has fewer opportunities to exercise those social muscles. She’s also found it important to stick to her routine with a set time to wake up and go to bed (having a dog helps!). She’s more careful about how she spends her disposable income, but besides that she has more time to pursue her hobbies like photography and keeping up with her travel vlogs and blog.

Her mindset has also changed from “the work I’m doing now will be my career for the rest of my life” to “I wonder what I’ll do next” – personally, I love this outlook because it completely tears down the ominous (and quite useless) question “what do you want to be when you grow up?” – a demand I’ve never felt I’d be able to answer.

What has surprised you the most about being on a career break?

One good thing is that there’s a mental liberty that comes from taking a career break. She no longer has the feeling of being tethered to a team or company, or of having to be always available via email or Slack. She was also pleasantly surprised at her self-discipline and how productive she’s been – she’s learned that she can trust herself :)

On the other hand, Justine shared that she’s in her own thoughts more often. Without the distraction of a workday or externally imposed deadlines or tasks, she has more time to overthink things. To help her focus, she dedicates time to one of her passions – photography. She makes time to go outside and take a few photos every day.

What advice would you give to someone who wants to take a break and try freelance work?

Justine stresses the importance for us to shift our mindset on career breaks. Taking a career break should be something we value as highly as buying a house or starting a family. There’s just as much risk involved to have achieved those milestones, but for some reason, we don’t pop the champagne when someone decides to quit their job to take care of themselves.

She also notes that it’s important to let bad advice roll off you. Often the people who give bad advice (“You should stay in your role! You’re so close to that promotion!”) have the best of intentions – but if you tune into yourself, you know what’s best for you.

She also thinks it’s helpful to remove the pressure of monetizing hobbies. She talks about how while she was working, she was also trying to “make it” with her photography. She felt like she had to justify how much time she spent on her hobby, and that kept her wheels spinning. But it’s so much more fulfilling to focus on how much fun it is, rather than turning it into a source of income. In a weird way, changing the goal to having fun sometimes brings in opportunities that wouldn’t have happened if the focus was on the hustle :)

Thank you so much, Justine!

There were so many nuggets of wisdom I picked up from my interview with Justine, and I feel absolutely inspired by her ability to follow her inner compass – even when it came with great risk and uncertainty.

I completely agree that taking a career break should be seen as a milestone worth celebrating, and applaud my friends who have been self-aware enough to know when to make that leap.

You can keep up with Justine on her blog or YouTube channel :)