Unplugging from Work: 5 Key Learnings from Career Break

I’ve been back to a full-time job for three months now. From July 2023 to April 2024, I took a career break to explore different paths. Initially, I planned to pivot to product management, but I realized it wasn’t for me and decided to return to digital marketing.

During this time, I organized many events, travelled for nearly three months, met lots of new people and reconnected with friends around the world. I also faced many rejections in job hunting and had concerns about my future.

Even though the job-hunting process was challenging at times, I’m very happy I took this time to explore. Personally, I’m happy with where I am now. And would like to share five things I learned during my career break. These lessons will stay with me for the rest of my life.

#1 Be a creator, not a consumer

When running events, working on side projects, and writing this newsletter, I see the ideas in my brain come to reality, I see I am creating something new. The creation process excites me. I get much more satisfaction from creating than consuming things.

You will get a lot of by-products from creating things. You will think more clearly, meet interesting people and open the door to new opportunities.

During the break, I wrote a total of 7 blog posts, including breaking down community building into a simple formula, structure of a memorable event, purpose of travel, and more. They all stem from my thoughts and experiences. When re-reading them now, I can still recall the memories of my career break and the moments I got inspired.

Looking back at my event calendar, I realize I hosted more than 8 events. There is a profound joy in my heart when I create something new that brings my friends and acquaintances together and makes the event happen in real life. Jamming ideas with different co-hosts during the preparation process, conducting research, and discovering common interests among participants.

#2 Talk to strangers, meet new people and catch up with old friends

Inspiration can be found everywhere, which is one reason I enjoy reading. Talking to people outside your usual social group and from different countries can be even more enriching. During my career break, travelling alone provided countless opportunities to converse with strangers and find new inspiration.

Interesting conversations often start in the most random places. Some of my most memorable discussions have occurred in a jazz bar in Malaysia, on a plane, and in the common room of a hostel in Japan.

• I met an Indian jazz bar owner in Kuala Lumpur while attending a big band jazz performance at Jao Tim (a live house in KL). He is passionate about jazz music and shared his story of how his jazz bar in India survived during COVID.
• A friend of mine in Singapore was deciding whether to leave her job and focus on her side business. We discussed strategies for business growth, our perspectives on work, and her plans to operate the business in the Philippines.
• In a Tokyo hostel, I met a Russian guy who happened to be my roommate. He works in the oil industry and follows a unique schedule: 45 days of work followed by a 45-day holiday. This lifestyle allows him to dedicate a significant amount of time to travel during his breaks, a new way of living I hadn't encountered before.

When I am back in Hong Kong, I also have many coffee chats with people I connect with on LinkedIn. Some of them even became my friends.

• A community manager turned service designer, both of us are in a transitional phase in our careers. She even became a co-host for Casual Tech Meetup. We ran our first LEGO Serious Play Workshop together. All participants visualized our ideas and shared our points of view through simple LEGO models.
• I met a startup founder of a sports event management app and another startup founder of a dating app. Both are amazing community builders. It is always interesting to hear startup stories and understand their thoughts about the problems they are trying to solve.
• I spoke with a corporate trainer who is also starting her agency. Before, I had no idea this type of career existed. It is similar to freelancing, with lots of flexibility, but she also needs to manage client expectations, run the business, and work with other teams and trainers to conduct the training.

Reflecting on these conversations, I realize that many people are not living a typical 9-5 job but are still living well and enjoying their time.

Reach out to people in your network who your online presence but haven't met you before. Ask if they are interested in talking. Most of the people are kind and willing to chat.

#3 List out the worst-case scenario and what I can get

Most of the time, our worries don’t come true. It was unsettling to see no income coming in, I also questioned myself a lot during the middle of my break, wondering what would happen if I didn’t get a job. How should I respond when interviewer asks about what I did during my break?

Listing out the worst-case scenarios won’t remove all your stress and worries, but at least you will have better control of your mind. You will realize it is not that bad and it gives you faith that you can rebound from it.

The Downside

• Money: Taking a career break for 6 to 12 months means no steady income. Luckily, I didn't rent a house. But it will also use quite a lot of my savings.
• Career: The worst case is that I would take more time job hunting (which was true) and end up with a job similar in scope and package to my previous one.

Another thing I noticed during the career break was the importance of listing out things you did that can’t normally be done when you have a full-time job. This also alleviates stress.

The Good

• Travel: I travelled for 3 months. No trip longer than 2 weeks had been taken during my university. But this time, there was an escape from work deadlines and pressure, allowing me to fully immerse in travel.
• Learning: There was lots of free time to learn new things. With an interest in pivoting to product management, I spend time on growth marketing and PM online courses. In the end, I didn't switch careers, but did learn things that I can apply to my current job.
• Exploration and Clarity: New ideas were explored and thoughts became clearer. I created a list of random ideas while travelling and discussed them with people during numerous conversations. Surprisingly, I wrote more on my personal blog and occasionally on LinkedIn.

#4 Spend more money and get used to it

I was afraid of spending money when I was taking a break. Whether it was an occasional dinner out with friends or getting a gym membership, I worried about using up all my savings and still not finding a job. Even though I knew rationally that this wouldn’t happen, I couldn’t shake the concern.

Looking back now, travelling more and spending more money during the break would have been a better choice. Perhaps a summer in Europe instead of Southeast Asia, enrolling in a spinning studio for daily cycling, or getting a monthly membership at a co-working space to stay focused and creative could have enriched the experience.

Towards the end of my career break, I read a book called “Die with Zero.” It introduced me to the idea of investing in experiences while we’re young because they provide compounding returns through our memories. Previously, I thought spending money on experiences in my 20s was a bit frivolous. Shouldn’t we delay gratification and invest in stocks so we can enjoy life in our 40s or 50s?

The book changed my perspective. It taught me that good experiences from the past give us a “memory dividend” each year. The longer we wait, the less time we have to earn this compounding interest.

I’m generally cautious with money, so spending more on experiences wasn’t likely to harm my finances significantly. Building the habit of spending money on worthwhile experiences takes practice, much like exercising a muscle.

Since returning to full-time work, I’ve been exercising my “money-spending muscle” by focusing on experiences I truly enjoy, like jazz, classical, and indie music concerts, art exhibitions, spinning classes, squash, buying CDs and books, and exploring new interests.

#5 Figure out things I want to work on

During my career break, I had more time to understand myself, what I’m really good at, and what I’m interested in doing. I also read a post by Paul Graham on how to do great work, where he shared common patterns among people who have produced great work.

The process involves four steps: choosing a field, learning enough to reach the frontier, noticing gaps, and exploring promising ones. This is how almost everyone who has done great work—from painters to physicists—has approached their craft.

I noticed that people are generally drawn to or want to participate in great experiences, whether it’s travel, a fine-dining experience, a well-thought-out and structured event, or even a great dinner party. However, when I observed the events and experiences in the market, I felt they weren’t fulfilling enough.

Are there ways to create experiences that leave a lasting impact? Human connection is essential in events and experiences, but can we go beyond that and design experiences that change participants’ perspectives through open dialogue, spark curiosity about specific topics, or inspire them to take action?

These are the questions I explored while co-hosting events during my break and talking with others. I’ve realized there’s a significant gap in the quality of experiences being offered. What I want to do is curate transformative experiences and gatherings for participants. I want them to leave the experience not only feeling connected but also experiencing a subtle change within themselves.

Ideally, these experiences would be integrated with products and services, creating a business impact and generating monetary returns.