Startup Diaries: on Telling the Boss You’re Leaving

It's a moment that many entrepreneurs have experienced: telling the boss that you're leaving to start your own venture! Jules Coleman, co-founder at Teddle, found that her boss' reaction, like that of her friends and family, surprised her.

It is almost 18 months to the day since I sat my boss down and told him I wanted to take a career break to start my own business.

I was beyond nervous. I had only been with the company a year. I had just been promoted to be a Senior Manager. I had current projects underway. I had junior staff I was in the middle of mentoring. This was not going to go well.

Eventually I summoned the courage to tell him why I had asked him to meet me for lunch. Dry mouthed, stumbling over my words, I managed to rattle off something along the lines of:

"I'm really sorry and I know you and the company have been great to me but there is something I've been meaning to tell you I've decided that I really want to try my hand at starting my own business and I'm worried that if I don't do it now that I may never get the chance but I don't want you to think that I'm ungrateful but I really need to do this…"

Looking a bit bewildered and trying to assimilate my ramblings, my boss leaned back in his chair.

After what seemed like the longest silence in history, he sighed and wistfully said the infamous line: "I had an idea once... but I never had the nerve to follow it through. Good on you"

And that was that. Far from being disappointed or angry at my decision he was supportive.

Similar conversations followed over the coming weeks as I let friends and colleagues know of my plans. Almost universally the response was along the same lines as that of my boss. People commended my bravery, for putting my money where my mouth was, for believing in myself. They wished they had taken the plunge when they had the chance. But life had gotten in the way. Mortgages, kids, partners, promotions, it had never seemed like the right time to start something of their own.

It seems this world is full of 'Closet Entrepreneurs'. People with the desire and passion to start something of their own but who never seem to get over that initial hurdle. The hurdle of; What will people think? What will my boss say? What if it fails? What if I'm not good enough?

In my experience the answers were a lot less scary than I had imagined in my head.

What will people think?

People will think all different kind of things.

Some people will be supportive, some people will think you are crazy, some people will be envious and some people will be all of the above!

What will my boss say?

If you are a good employee they are unlikely to be ecstatic to lose you. But if they really care about you and your development then they would never guilt you into staying.

What if it fails?

Yep, it might. A lot of new startups do. But there is a reason why investors favour 2nd and 3rd time entrepreneurs. Unless you have your eyes shut, even a complete failure of a business will teach you so much about yourself and running a successful company that you are bound to be better next time around.

What if I'm not good enough?

I have been out of my comfort zone and my depth since I began this journey.I'm doing everything for the first time.

I make mistakes all the time. I try and learn from them and sometimes I don't even manage that!

You may find that you really don't like the realties of running a business. And that's ok too. At least you can go back to being an employee without the lifelong regret about what could have been.

Don't get me wrong, that initial leap was probably the biggest I've ever had to take. It was nerve wracking and I was plagued with doubts. Here I was, giving up a highly paid city job to start a business from scratch. I didn't know when my next pay check would arrive. I didn't know anything about building a product. I didn't know anything about raising investment. I didn't know much. But it was a catch-22. If I stayed at my job I would never get the chance to learn those things.

18 months later, I know a lot about building a product and raising investment. The first pay packet took 11 months to materialise. It's a damn sight smaller than my old one but I wouldn't trade places for anything.

So tear off that band-aid. Take the leap. Don't be the person that wonders what might have been. The water's not too cold, I promise.

Jules Coleman is co-founder of Teddle, the easiest way to book a cleaner online. Prior to founding Teddle, Jules worked as a Management Consultant with PricewaterhouseCoopers, working on performance improvement projects with global companies.

Not from a technical background, Jules bought a book and taught herself how to code in order to build the first version of Teddle. Since then Teddle won a place on the prestigious Springboard accelerator programme based out of Google Campus, London, secured £250k in seed funding and have expanded its product across the Greater London area.

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