Can’t quit your job? Start up a business on the side!

If you want to start your own business but can’t afford to quit your job, what do you do? You start up a business on the side, that’s what! Here’s how.

Moonlighting FTW
Moonlighting FTW
The story of how we got started in building our own business is so frustratingly irrelevant to other people’s situations that we can’t ever point to it and say: “That. Do that.”

We had savings, we had limited responsibilities, and we had naivety on our side. But if you don’t have those things, how on earth do you go from your 9-to-5 to working for yourself and building a business you love?

Here’s how:

Start up a business on the side

Although we didn’t start up any dedicated businesses while we were in paid work (because we didn’t realise we actually wanted to), we still found the time for lots of money-making side projects… and this post will show that you can too – whatever your situation.

Below are some ideas for how you can get started. Firstly though, a few caveats:

  • This isn’t about starting up a billion-dollar business while in your 9-to-5. This is about starting very small. It’s about gradually improving your skills and making enough money to the extent that you have the confidence to quit your day job.
  • This won’t be successful without effort. You need to be up early and willing to forsake after-work drinks with colleagues.
  • For all the suggestions below, you’ll need to assess whether there’s a conflict of interest with your day job. If your boss finds out, will you be put on gardening leave faster than you can say “Cubicles make me antsy”?

So, let’s get into these ideas…

Write an ebook

Self-publishing means that anyone can write a book today and sell it on Amazon tomorrow. We don’t know anything about the fiction market, but we know that non-fiction can be pretty lucrative – and it can open you up to many more money-making possibilities in future.

You don’t even have to be an expert in the field you’ve chosen – you just need to be interested in it. To give a couple of examples:

Haggadah Good Feeling About This: Passover guidance for confused Jews: A few years ago, I decided to rewrite the Haggadah – the book used during the Jewish festival of Passover. Every year my family would read the original Haggadah at the festival meal and not have a clue what was going on. So I decided to use my weekday mornings and evenings to do the research and rewrite it in a fun, easy-to-understand way.

Rob convinced me to self-publish it, so I got a Jewish woman on Elance to proofread and fact-check everything, and I found a Sri Lankan man on Elance to create some illustrations. I did it for fun and from the position of being completely clueless. And while I’d never advise you to go into such a seasonal niche, I now sell a hundred or so books every February/March (before the festival).

Property Investment for Beginners: Rob wrote a book called Property Investment for Beginners. He knew a fair amount about property investing from his direct experience, but wanted to expand his knowledge and clarify his thinking on some subjects – and figured that explaining the subject to someone else would help him do that. That book now makes over $1,000 a month on Amazon (paperback and Kindle combined).

First steps

1: Figure out which niche to write about

2: Write the book

  • You can just write the book in Word, and the formatting required to make it work on Kindle is pretty straightforward. Amazon’s official guide is here… or you can just hire someone on Fiverr to do it for you.
  • It doesn’t need to be long. Between 12,000 and 15,000 words is long enough for a self-published book. If you can solve someone’s problem through what you’re writing (see above), they’d rather you did it in 12,000 words than 100,000 because you’ve saved them reading time!
  • Look at the reviews of books in those categories on Amazon to see what people like about them and what they’re unhappy with – and make sure your book “fixes” what people are unhappy with. For example, many readers are fed up with the amount of “filler” in books – the unnecessary repetition or irrelevant information – used to increase the size and perceived value of the book.

3: Publish the book

Everything’s quite self-explanatory and easy to follow:

  • Get a really great front cover designed – something that will stand out among a sea of other thumbnails, even at the tiny size displayed for search results. People do judge books by their covers, so this is an area worth spending a little more on rather than going to Fiverr.
  • Create a paperback version too: it makes your Kindle version look like better value, and builds trust because “proper” books have paperback editions too. Use CreateSpace for your paperback version.

Ways to make more money from the book

Encourage people to register their email address with you

The problem with Amazon is that you don’t get to know anything about your readers – apart from if they leave reviews. An email list is one of the most important things you can have in this game; here’s why:

  • You can email your list about other related books you’re bringing out.
  • You can upsell them on special packages – which they can buy from your website. (These are things that would complement your book. E.g. if your book is about healthy eating, the upsell could be a healthy eating plan.)
  • You can ask them (very nicely) to review your book if they’ve enjoyed it.
  • You can email them to let them know about coaching/consulting work you’re doing in the field related to your book. Then they might hire you!
  • You can email them to find out what other pain points they’re experiencing – which will give you ideas for future books.

So how do you go about it?

Here are a couple of ideas:

  • At the front and end of your book, tell people that if they register on your site, you’ll give them X for free (something related to the subject matter of the book). Then before you publish the book, create a VERY simple site with a form where people can enter their email address.You can then email these people (not too frequently!) when you have a new book out in the same niche.
  • At some stage you could create extra “special packages” on your site, and then you can email your list about them. Here’s an example of Rob’s page, which contains a bonus package for existing buyers:

More books!

Create more books on related topics if your first one was successful. You can also email your list about these new books.

Speaking gigs, punditry, events, etc.

The opportunities are endless.

Do you want more detailed information about book-writing (upsells, pricing, book blurbs, niches…)? Let us know if it’s something you’d like us to write more about.

Start a podcast

As a podcaster, iTunes – not Google – is the search engine through which you’re most likely to be found. This gives you three big advantages when it comes to finding an audience:

  • You’re more likely to be found because there’s less competition: there are far fewer podcasts on each topic than there are blogs. There might only be one or two other podcasts in your niche, compared to thousands of blogs.
  • People browsing iTunes are looking for a show to subscribe to, based on one of their interests. That’s very different from Google searches, which are often just about looking for an immediate answer to a specific question – meaning you have to work hard to convince them to stay longer than they intended.
  • Because people browsing iTunes are looking for content based on their interests, that’s what your podcast should give them: content, rather than any sort of sales pitch. Which is good for you, because at the moment, you have nothing to sell!

Again, it doesn’t matter if you’re not an “expert” in your niche – you just have to be interested. Rob started The Property Geek Podcast because he wanted to better understand property investment. He invited experienced property investors onto his podcast to be interviewed – which provided him with the information he was after, and them some exposure and much-needed love: they rarely reach celebrity status in the real world.

The result? Heaps of other people wanted to know the same sorts of things as Rob, so the podcast blew up… and heaps of other opportunities developed from it (including a second podcast – this one as a co-host – as well as a forum, a book, and soon a new rental agency).

Bear in mind: Unlike all the other side-job ideas in this post, podcasting itself doesn’t make money – instead it creates opportunities to make money. As a result, the financial rewards might be a bit slower to arrive than the other side jobs.

First steps

1: Read Rob’s blog post about creating a podcast

It’s aimed at business owners, but the tips are applicable to everyone.

2: Think about the niche and the angle

  • Don’t worry about competition: if someone loves photography (for example), they’ll happily listen to three photography podcasts per week. But you do need to know who else is in your space so you can find a unique angle and not accidentally copy someone exactly.
  • Do you focus on travel photography, when all other podcasts are discussing big bulky equipment? Are you all about “the best camera is the one you take with you”, or are you more about weighing up the minute differences between cameras? Think about what view on your subject people will get from you that they can’t get from anyone else.

3: Map out the show

  • How often will you put out a new episode? Weekly is best, but it’s important to be regular and reliable – so if you can only do monthly, monthly it is.
  • What will the format of your show be? Will you be interviewing guests? Will it be just you talking? Banter between co-hosts? There are pros and cons to each – think about what’s most appropriate, and what’s unique in your market.
  • What will the structure of your show be? One person rambling for 25 minutes is booooooooring. Listening to two people talk isn’t much better. You need discrete segments – like news/main topic/tips – to keep things moving and give the listener something to look forward to.
  • What will the call-to-action at the end of the show be? You can only ask your listener to do one thing or they’ll get confused and do nothing. So choose wisely.
  • Write down ideas for 20 episodes. Each episode needs a main topic, and generating 20 before you start is a great way to prove to yourself that there’s enough to say and you won’t run out of ideas.The only exception is if your podcast is strongly news-based – but this is only really recommended if you’re podcasting about a very fast-moving industry where you could fill up a whole episode with important developments even if your show was on daily.
  • Decide on a name for the show. Keep it simple – “The Travel Photography Show” – unless there’s a really good reason not to.

4: Record the show

You just need a microphone, recording software and audio hosting. Outsource the audio editing and REALLY don’t get hung up on the techie stuff. Here’s what Rob suggests:

Microphone: Logitech USB Headset H530
“Serious” podcasters will laugh at you for using a Madonna mic, but that’s fine: you’ll already have recorded 20 episodes and made a bunch of sales while they’re still debating the best EQ settings. Don’t know what an EQ setting is? Keep it that way.

You won’t get the best audio quality in the world, but you won’t be paying $thousands for it either – and all you need to do is plug it into the USB port of your laptop.

Rob’s recorded over 150 podcasts with this mic, and no one has ever complained about the audio quality.

Recording software: Audacity (free)
You could also use Garageband if you’re a Mac user, but Audacity is simpler and it works on Mac and PC. Even if Rob’s laptop died five minutes before recording an episode, he could just grab a friend’s, install Audacity, and be recording with minutes to spare.

Skype call recording (optional): iFree Skype Recorder for PC (free); ecamm Call Recorder for Mac ($30)
If you’re interviewing people on your show, you’ll need some way to record the call (assuming you’re not with them in person). The easiest way is to call them through Skype, and use one of these two pieces of software to record the audio.

Audio hosting: Blubrry ($12/month)
You need somewhere to host your audio so that other people can stream it – and Blubrry is a good deal at $12 per month. The cost includes a useful stats package for you to obsess over how many downloads you’re getting. People also recommend Libsyn, but we haven’t tried it.

Audio editing (about $25 per episode)
This is where everyone goes wrong. Why would you spend literally hours editing your own audio (two hours to edit a 30-minute episode on a good day) when you can outsource it for $25 per episode?

That’s what Rob pays, and he found his editor on oDesk. The oDesker has now edited over 75 episodes, and never done anything less than a stellar job.

Does all this sound like a big time suck?
It takes Rob 90 minutes per episode – that’s 90 minutes per week if you decide on a weekly podcast.

Ways to start making money from podcasting

Start a forum for people who are just as fanatical about your topic as you are.

Rob did! He now has 800 members, including 80 members in the “Plus” section of the forum who pay a monthly fee for extra content and features. (We open up “Plus” membership every few months and then close it again to let new members bed in.)


Listen to this podcast interview with John Dumas from Entrepreneur on Fire about how he negotiated colossal amounts of sponsorship. (Admittedly his podcast series was a full-time gig from the start, but there’s no reason why yours needs to be.)

Start to consult in the industry in which you’ve been podcasting about

When you start a podcast and you get popular, your listeners will come to you and ask to pay you for your advice or guidance.

Create a product that you know your listeners will love

You can learn a lot about your listeners’ needs if you ask them to email you, leave a voicemail, etc. You can then create a product that will help them. If, for example, you do a podcast about property investment and everyone’s particularly intrigued by your episode on “paperless property management” (this happened to Rob), you can then create a whole video course about it and sell it to them.

Do you want more detailed information about podcasting (equipment, getting on “New and noteworthy”, etc.)? Let us know if it’s something you’d like us to write more about.

Get yourself on Fiverr

Before we’d quit our jobs, we were doing jobs on Elance and Fiverr. There really is potential to make decent money even on the Fiverr platform, and it’s a great way to sharpen your skills.

First steps

1: Find your niche and start selling gigs

Look through the Fiverr gigs and discover which seem to be heavily in demand, and which you think you have the skills to deliver.

Create a few different gigs around the same niche and follow their progress closely. See which gigs get the most traction, then dispense with the other gigs and focus solely on the successful ones.

Consider having a video for each gig. Fiverr favours gigs with videos for some reason, so you’ll appear higher up the search results if you record a 30-second video talking to camera about what you can do for customers. For any gigs that involve writing, this is particularly helpful: it will reassure buyers that you’re an articulate English speaker.

Side note: make sure you have a great profile to build trust.

2: Upsell upsell upsell!

For an example of just how profitable upselling can be when done in the right way, check out this podcast interview: This podcast gives some really handy pointers on how to get good reviews – which are essential for earning more money on the platform.

Below are some examples of gigs and upsells (known as “Gig Extras” on the platform) that we found on the site; they might give you some inspiration for your own:

Gig 1: I will teach you how to create backlinks and learn SEO yourself for $5 [this is a pre-created course – it already exists. The the seller just needs to send it out when people buy the gig]

Gig Extras:

  • I will create a few backlinks for you, to help you get started: $10
  • I will review your website using my knowledge and SEO tools then give you tips on how to increase ranking: $5
  • I will enjoy an extra cup of Dunkin Doughnuts coffee, thanks to a satisfied customer: $5

Gig 2: I will turn You Into a WordPress NINJA for $5

Gig Extras:

  • I will include my course on how to optimize WordPress for speed and security, great for safety and for SEO: $10
  • I will include my 56 minute video on how to use WordPress and FREE plugins to setup a paid Membership Site: $20
  • I will turn you into a master of cPanel, the engine powering your WordPress installation, domain and email: $5
  • I will deliver this order in just 1 day: $5
[Note how every item in Gig 2 is pre-created – and he still charges extra for delivering quickly even though all he needs to do is send a link!]

Once you rise up the levels of Fiverr, you’ll be allowed to charge more and more for your Gig Extras. Check out this guy. And this one.

Ways to make more money from Fiverr


Upselling via “Gig Extras” is the way to take your average transaction from a puny $5 to $20, $40 and beyond. As you saw from the examples above, it doesn’t even need to involve that much extra work on your part.

Consider taking your clients OFF Fiverr

If you find yourself with some dedicated, trusting clients who really like your work, you could suggest doing work for them offline too. Fiverr frowns on this so you shouldn’t suggest it openly in a message on the site. Instead, attach a file (PDF, DOC or TXT) which explains what you’re proposing to them.

Once you have a relationship off Fiverr it makes it easier for you to charge higher prices, as well as move to a monthly retainer model – which just isn’t possible on Fiverr.

Become a consultant

Would you make a great project manager for a web development project? Do you know how companies can become more efficient? Are you a whiz when it comes to car financing?

As long as you’re not doing anything that contravenes the contract you have with your employer, consider getting paid to help others with those things!

How do people find out about you in the first place?

  • Start a podcast. See above


  • Write a book. See above again!


Start a blog as a way in to consulting

With consulting, you can take on more or fewer clients depending on how much time you have available outside of your job.

Here are some tips on getting started:

1a: Answer questions on forums, Quora, Reddit, etc.

  • Scour Reddit for subreddits about the niche you can provide expert advice on. If you’re unfamiliar with Reddit etiquette, read this before you answer any questions.
  • Do some searches for blog posts to do with your niche and start commenting at the end with useful information.
  • Find out if there are any forums or communities around your chosen niche, and start contributing regularly. Don’t sell your services though! On forums and Quora, simply have a “signature” or profile that includes your name, “job title” and a link to your site. For Reddit, you can’t have a “signature”; instead, you should very occasionally provide a link back to your site within your answer. Be sure to read about Reddit etiquette before you do this though.
  • If you haven’t already, set up a profile on Disqus – lots of blogs use it as their commenting system. This means that every time you comment, the comment links back to your site.

1b (at the same time as 1a): Create a REALLY simple website

Your site just needs to have two main pages: the blog, and a “services” page – where people can book a consultation with you. When you include a link to this website in your “signature” when you reply to questions on Quora /forums/blog comments, people will click on this link to discover other gems of information you can provide!

The blog should be on the homepage. For blog post content ideas…

  • Scour other blog posts about the topic, and see which ones get the most questions/comments at the end. Then write a much better blog post, which includes way more information and also incorporates any questions/comments the other readers had. (I.e. become THE authoritative source on the subject.)
  • Repurpose your Quora/Reddit/forum answers into blog posts.Don’t be afraid of “giving it all away” – i.e. giving away lots of detailed and useful information about your niche. It’ll prove you’re a trusted authority, and people will still want to hire you because they’ll want advice that’s specific to their situation.

Someone who’s nailed the whole “use a blog to show off expertise and get work out of it” is Tom Albrighton, a British copywriter. On his website, he has a highly influential blog in which he discusses everything to do with brand copywriting. The blog is fascinating, and it’s clear that Tom really knows his stuff. He also has a services page, so that you can hire him (or tell your friends about him if they need to hire someone).

2: Get even more traffic by guest posting on blogs and appearing on podcasts in and around your niche

Write really compelling emails to blogs to explain what you’d like to write a post about, why you’re in a position to do so, and what their readers will gain from it. Make sure the emails are personalised and full of your personality.

3: Get bookings through your site

By this stage you’ll have needed to figure out what questions you’ll ask people when they book your service, as well as a structure for the entire consultation process with them.

4: Get feedback from clients

Find out what they liked/didn’t like about your service, which information they valued the most, etc. This will help you provide better work for future clients.

Do you want more detailed information about consulting (pricing, productising, etc.)? Let us know if it’s something you’d like us to write more about.

Some parting thoughts

For the love of goodness, think hard about your target market

Will your audience spend money?

This is very much tied in with picking the right niche. If you’re starting up a podcast aimed at helping people who are severely in debt, good luck getting them into a paid membership forum – or even paying for your follow-up book.

Another example is travel bloggers. Want to write a book for travel bloggers? Travel bloggers try to get everything for free, so here’s what will happen: they’ll ask for a review copy, and then they’ll write a wonderful review of your book on their site. And then what happens? Well, the majority of people who read travel blogs are other travel bloggers, and they’re not going to buy your book either.

You don’t have to create huge businesses out of these

For us, Elance and Fiverr were ways to start making a bit of money on the side while in our day jobs, and to give us confidence in our abilities to find jobs and do high-quality work for clients.

Although we could have tried to build a hugely successful business through Elance or Fiverr (like this guy and this guy), we just used it as a jumping-off point to start up our own business. Likewise, writing books is just a fun hobby for us that happens to make money. These ideas can be the start of something big, but they don’t have to be – it’s up to you.

There are plenty of other “on the side” jobs

These are just the ones we have experience in.

You don’t need to be an expert in your chosen niche, but you DO need to have an interest in it

Getting up early, or working on your side gig when you’re exhausted after your day job, is never easy – but it will be even harder if you couldn’t care less about what you’re working on.

What do you think?

Are you doing any work on the side at the moment? Do you want to? Do any of these ideas appeal to you – or do you want to know about any others?

Let me know in the comments!