Stealthy startups: How to keep your side projects a secret from your boss

Posted on Jan 8th, 2015 | Planning

I’m a very lucky chap when it comes to moonlighting – doing the odd bit of work on the side isn’t just common amongst the Crunch team, it’s positively encouraged. After all, how better to know the people we’re looking after than walking a few miles in their shoes?

We have freelance writers, videographers, fashion bloggers, actors, and many more under our roof – and we all support one another with hot tips about places to find work and managing a business outside business hours.

Many people aren’t so lucky though. Evening and weekend work is a big no-no for some employees, and in some cases it’s legally forbidden by employment contracts. For these reasons and more, some part-time business owners choose to keep their outside interests a secret from their employers, but this can be a tricky task.

So, if an uptight employer means you need to keep schtum about your side projects, how can you juggle both jobs without giving the game away?

Loose lips sink ships

If you’re trying to keep your fledgling enterprise on the down-low, perhaps the most obvious thing is to not tell anybody about it.

Offices tend to be hotbeds of gossip and Chinese whispers, and it’s not uncommon that even idle water cooler chit-chat makes its way around the building. Although there are exceptions, the knowledge that you’re imminently checking out can sour employer / employee relations and may make your last few months at work a real nightmare. So keep your mouth shut about your new business unless you know you can trust the person you’re talking to.

Remember – the first rule of entrepreneur club is you don’t talk about entrepreneur club.

Don’t burn out

Working one job can be stressful and tiring enough, so it’s highly likely that working two will have a material impact on your physical and mental health. Combine that with the unpredictability of business ownership and you have a dangerous mix. If you go from happy and productive employee to lethargic office grouch in six weeks, the jig is up.

Overwork yourself and both endeavours will suffer. Devote too much time to one and you’ll hinder the other. What if you wear yourself out setting your new business up, only for it to fail, leaving you in a job at which you’ve been underperforming for months? It’s a hell of a balance to strike.

You have a few options here. Firstly, you can request flexible working from your employer. This right was extended to all employees in 2014 (it was previously only available to those with family commitments) – however you only have the right to request it. Your employer is still well within their rights to deny that request if they have a legitimate reason.

Secondly, you could look at going part-time. Most employers are open to the idea of job shares or reduced hours these days – it certainly doesn’t hurt to ask if you feel you’re working yourself too hard.

The third option – and the one most moonlighters trump for – is to just manage your time very carefully, and be aware of the impact on your wellbeing and productivity. The trick is to find a balance that works for you. Maybe you can devote one weekend a month to your new business, or maybe weekday evenings. Make sure you have downtime to spend with family and rest.

When should you come clean?

Many secret entrepreneurs never tell their boss about their business ambitions. They work on them quietly and, if the day comes that the business can support them financially, they hand in their notice.

If you’re in breach of your employment contract (which, of course, we would never recommend) you could be in real trouble – think sacking, employment tribunal or worse – but if you’re in the clear legally, the worst that will probably happen is your boss being a bit grumpy.

Keep in mind, though, that more and more employers are supportive of go-getter business acumen and will help employees with bigger ambitions realise those dreams. Bosses opposed to staff having side-projects are now the exception rather than the rule. As long as it’s not affecting your day-to-day work, why should your boss object?

You’ll be in good company

Some wildly successful startups have been started as side-projects of people working elsewhere. Whether it was a killer idea, an entrepreneurial itch that needed scratching, or just blind luck, these well-known businesses were all started while their founders toiled away at a 9-to-5.


Benji Lanyado was working as a journalist when he spotted a gap in the market – a website that allows photographers to sell their snaps directly to companies and consumers (rather than through traditional agencies).

With none of the necessary skills and no budget, Benji took coding classes in the evening until he could build the website himself. The early version of Picfair of the service allowed him to raise around half a million pounds in venture funding to grow the business.


Everyone’s favourite pithy social network can trace its roots back to when co-founders Ev Williams, Biz Stone and Jack Dorsey were working on an ultimately-moribund podcasting company called Odeo. Realising the writing was on the wall after Apple waded into their niche, Dorsey and two other developers came up with the idea for Twitter – then called Twttr – and presented it to the rest of the company.

Although Twitter’s early days were far from idyllic, the company has become a financial success and something of a cultural touchstone.


Fixed-fee money transfer firm Dwolla wasn’t just started while the founder was working for another company – the problems experienced in that job gave Ben Milne the idea for the whole business. As he tells Business Insider:

“I owned a speaker manufacturing company and we sold everything directly through a website. I got really obsessed with interchange fees and how not to pay them. Every time a merchant gets paid with a credit card they have to give up a percentage. In my case, I was losing $55,000 a year to credit card companies. I felt like they were stealing from me — I was getting paid and somebody was taking money out of my pocket.

“So I thought, ‘how do I get paid through a website without paying credit card fees?’”

Is now the time for you?

If you reckon it’s time for a career change and are considering setting up your own business, visit our #GetStarted homepage for free resources and advice on how to make it happen.

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Written by Jon Norris

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