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Article: How I asked my boss for a career break to start my business

How I asked my boss for a career break to start my business

Flashback Friday (oops it's Tuesday.. Take me back Tuesday) to the day that I mustered up the courage to tell my boss that I wanted to pursue calligraphy & lettering full-time. These were my thoughts that I'd written down at the time.


Today I asked my boss whether I could take a career break for a year.

I had scheduled a meeting with him to do some 'career planning' but when the moment arrived, the whole speech I had planned went out the window and I blurted out, "I'm thinking of taking a career break." I was so nervous that I actually felt sick. I was so worried that he'd say no and I'd be staring down the barrel of unemployment. 

Looking back on my four years of working in Corporate, I'd spent 2.5 years doing tax work, 0.5 years on a secondment at the client's company, and 1 year on secondment in the data analytics & digital product development team. I hadn't exactly displayed unwavering dedication to a career path. I was, as they say, a typical, restless Millennial flitting from position to position. He might as well fire me then and there.

He didn't, luckily, and I'm truly grateful to have such a supportive boss, because having an option to return to my old job is a safety blanket that I won't take for granted. His biggest concern was actually just about the company's policy on employees who seek employment whilst on a career break. I realised he was worried that I could be hunting for a job at a competitor's boutique consulting firm but no, I reassured him that I was actually wanting to pursue my creative venture - my calligraphy! I saw the relief and some surprise on his face, because it's pretty much the polar opposite of tax accounting. 

Usually I have no problems speaking about my calligraphy business dream with others, and have strong convictions about why I want to do it, I'll admit that sometimes that fear of judgement still gets the better of me. I actually rehearsed how I thought the meeting with my boss might play out, in my head, many many times. It usually ended up with the worst case scenario of what I would say if I didn’t get his approval/ support.

During the actual meeting, I was surprised that the words came quite naturally to me, and I didn’t have any reservations about expressing what I wanted to do. I guess the more you speak about something, the more you feel comfortable hearing the words come out of your mouth, and the more you really start to believe it.

Thinking back to all the perfect things that I could’ve said in that meeting but didnt, I realise that it doesn’t really matter, because the outcome would've always been the same. I would've forged on ahead with my calligraphy venture regardless. And plus, people forget things. They return to what they were worrying about before you opened your mouth, the minute you are gone.

As I left the meeting, I remembered to savour the moment. The feeling of relief that washed over me as I returned to my desk made me fee light, and free in a sense. It hasn't really sunk in yet, but it started to when people started saying that they’ll miss my presence around the office. It was a really warm feeling.


That day was a defining moment in my career. The memory of it is encased in a bubble. To all of you who have experienced something similar, here are my parting words (until the next post).

For the difficult times ahead, you have to remember the conviction that you felt when you decided to embark on this journey. How you chose your own path, carved it, and consciously and actively made choices based on your knowledge that it was the right decision at the time. Don't forget that real sense of excitement; of knowing that you're pursuing something that you could really find fulfilling. And most importantly, don't give up on all the potential that you know you have.

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