I was doing so great in my job that I decided to take a break

How a product guy decides to go “Eat, Pray, Love” — with none of those things.

My story of finding something I was good at

Careers, like life, are all about growth. You try to discover what you are good at, and then try to get better at it. Occasionally, you pivot, using your skills in new ways. Finally, you reach a point where you say, “Huh, this is pretty close to what that ikigai book was saying!”.

I found myself in this fortunate situation as I landed into product management after a decade of different roles across analytics, consulting, sales, and strategy. This role allowed me to flex my creativity and problem-solving skills, while leveraging a decade’s worth of experience in my business domain of Insurtech, specifically catastrophe risk management. If those last words sound unfamiliar to you, don’t worry, it’s a pretty niche area. Think managing uncertainties around earthquakes, hurricanes, floods, fires — catering to the insurance (hence Insurtech) and risk management industries.

So, I got to the position of head of product management and marketing for a growing product company that focused on my very specific area of expertise. We were continuously adding features, expanding the market base, getting new clients. Sure, it was hard — anyone who has worked with product will tell you that it’s a demanding job — but you can’t beat the satisfaction of collaborating across teams to have something tangible materialize from your thoughts into the hands of users.

The case for a conscious pause

Well, sounds like a happy ending there, doesn’t it? Not quite yet. My role meant that I started looking for inspiration in all the great products that surrounded me, from everyday apps to complex business-oriented software. And with inspiration, came the itch to build, to explore, to experiment, to see what’s outside my specialized area of interest.

Let’s be clear, it wasn’t a case of burnout (although I did need a good nap, but that didn’t change my mind). It also wasn’t about trying to catch up to new technology. It was about stepping out of my comfort zone, connecting with people outside my immediate network, and ultimately, understanding what makes us tick.

So I decided to take a break. In fact, as I write this, it’s been a month since my last day on my job! My broad agenda was to be hands-on, picture ‘rolling up your sleeves and restoring a classic car’. However, as I proceeded, it took shape into five areas:

• Learn: Like many of us, I picked up my skills on the job. I realized that I wanted to deep dive further into psychology, design, business, growth, and strategy.

• Create: My main motivation was to build. The list included my own website, a bunch of product prototypes, and possibly a couple of apps. The list also included sharing my journey and any insights I picked along the way. In fact, this article is my first foray into writing, so I have already got a start there.

• Experiment: We have all played around with AI prompts to generate content — text, images, music (and soon videos). I’d be remiss if I didn’t take some time out to see what else I can do with the potential of AI, and tie it back to my goal of building.

• Connect: I already had a great network, but it was limited to my industry peers, college mates, and friends. I knew I had to take this opportunity to expand my circle further to find mentors and like-minded people.

• Improve: All of this can’t just be about work now, can it? It was important to prioritize both mental and physical well-being throughout the process.

As Marty Cagan said, “Fall in love with the problem, not with the solution”. I knew what questions to ask, and the answers may now lead to a pivot into a new field, a return to my previous role armed with a revitalized spirit, or something completely unforeseen.

The pre-flight checklist

All this may resonate differently depending on your current career stage. Full disclaimer here, this is not a call for you to jump ship. Taking a break is scary, and probably drastic in most cases. You can absolutely achieve your goals with the right attitude, resources, and time management.

If taking a break still sounds like a good move, you need to align certain parameters. Let’s check off the key ones here:

• Money: The most obvious aspect. The root of all evil. Our favorite thing. Yes, first off, a financial runway is mandatory. You’ll need to squirrel away enough cash to sustain you (and fund your projects) for the duration of the break, while making sure you have your investments and rainy day funds untouched. It’s ok if you are not in a position to do so, owing to your current scenario and obligations. You can always micro-dose the steps outlined in the next section. As I said, with the right mindset, you don’t even need a break.

• Support: You need to manage the expectations of your support network. This includes your partner, family, close friends — the ones that will be directly affected, and in return will impact your mindset. If you are truly convinced of your choice, they will root for your success too.

• Job: Your colleagues still have to hold the fort, so do a planned, responsible handover as you leave. Train people, document everything, optimize processes. Go the extra mile.

• Timing: Ties in to all of the above. You can always move your break by a few months here and there, so ensure that no long-term personal or professional projects are negatively influenced. Beware, though, there is no golden moment — you’ll just need to find what’s the best option for everyone involved.
  

OK, so you said goodbye to your paycheck and have become a bum. Let’s see how to approach this new paradigm.

My toolkit for a break

The most fundamental aspect of starting this break is to define an end goal. Before you begin, write a SMART (Specific, Measurable, Achievable, Relevant, and Time-Bound) goal on a piece of paper. And then chuck that paper out the window.

Although you have made up your mind, your mindset has not evolved. You don’t want to be in the same position that led you to take a break in the first place. If you plan a 3–6 months break, like myself, then the first couple of weeks (at the very least) should be for introspection. Understand your strengths and values. Broaden your thought process and think about what gets you in the “flow” state. This is where a plethora of resources — books, courses, TED talks — come into play. I’ll be sharing a more detailed list in a separate article, but don’t be too discriminating about what you consume at this point. Explore around and relax.

You will start getting an idea of how you are going to make use of your time. Now, become ruthless with it. Time management and prioritization is everything at this critical juncture. When you can literally do whatever you want the entire day, you have to structure your routine carefully and with balance.

Next, get your resources ready. For me, it was selected online courses, along with a mini-library of books, on topics ranging from business and product to life and success. Once you have identified what you want to understand and create, it’s time to learn, or relearn the fundamentals and become good at it.

It’s then time to experiment fast and early. Set weekly, fortnightly, and monthly goals. Don’t fall into the trap of perfection, it’s about getting out there. It’s not just your professional output — start writing a blog to align and share your thoughts and progress. Take my lead. This is my first article here, so why not publish yours?

This is also the best time to get out of your bubble. Find communities, forums, online groups. Once again, don’t worry about sounding right. It’s all about sharing and learning, that’s what everyone is there for.

Finally, keep yourself front and center. It’s a great opportunity to pick a hobby, exercise more, eat better, and practice mindfulness. Have some non-work fun too — a trip might be the inspiration you need!

The end goal — continuous evolution

Remember the piece of paper I asked you to throw out the window? No, you don’t have to go out and pick it back up. But it’s important to monitor your progress and refine your goals as you move along. You may start building momentum with broad ideas, but you need to convert those into tangible targets as you proceed with your journey. My fellow product chaps will recognize this as the central tenet of the ‘agile’ mindset, a popular (to the point of being groan-inducing) framework in software development.

I’ll be checking back in as I continue my journey. I also invite you to share your thoughts — Have you ever been on a sabbatical? Has the idea of a creative reset, however you define it, ever crossed your mind? What’s holding you back, or what might inspire you to try it?