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Eight months ago my girlfriend (now fiance) quit her corporate job, created a profile on a freelancing website and ran off to travel the world with me. Now she has more offers for contracts than she can handle, is able to work from anywhere in the world and earns over double her old per hour salary.

And she did it entirely off her own back. Before quitting she knew nothing about freelancing or working online, I didn’t push any jobs her way and this is the first time I have ever mentioned her on this blog.

Let me tell you her story.

Not Convinced

Ever since I first met Emma, I have been trying to convince her to quit her job and work for herself. But she was having none of it. There were all the usual excuses:

“It’s a good job, I’m lucky to have it. So many of my friends are struggling to find a job at all.”

“I’m on the ladder for promotion. In 20 years I might have made partner. If I leave the system I will never get back on the ladder.”

“I’m not earning enough to save any money, if I leave I’ll be broke”

“If I quit I won’t be able to come back”

“I invested so much in my education and I’m the first person in my family to go to universtity. It would be such a waste to leave it all now.”

They’re not bad excuses and they’re all true. It’s never an easy decision to change your life, you have to weigh up the pros and cons and there will always be some cons. It’s just that in this case there was half a million pros and only a handful of cons.

Emma was working in marketing at PwC, a large professional services firm, while living in a flatshare on the opposite side of London. She was commuting an hour each way and spending far more than her contracted hours in the office.

She didn’t have a particularly unpleasant job. In fact, her story so far is pretty much the same as any other twenty-something working in corporate London.

But in my opinion, standard corporate life is pretty awful.

Finally, after sending her hundreds of pictures of paradises around the world and bragging about my lie-ins and three-hour lunch breaks, she cracked and we came up with a plan for her to escape.

Growing A Nest Egg

“It’s impossible to save and live in london. Our generation is screwed” – Emma pre-trying to save.

The plan was pretty simple. We would choose a date to leave and then she would enter frugal mode and try and save as much money as she could. She had a promotion coming up so a combination of that extra earning and a cut back on eating out and should do it.

We set the escape attempt for March 2016, about seven months away. Enough time to get promoted, spend a bit of time in the new role and most importantly – stack up some savings.

In August 2015 I told my business partner Ben our plan:


Emma holds a pretty similar opinion to most of our friends: our generation is screwed. We don’t earn enough and cost of living is too high. It’s impossible to save, so I’m not even going to bother to try.

We sat down and went through all her spending and put together a budget that would allow her to save £300 a month. I said she entered frugal mode, but I doubt anyone else would describe three meals out a week as frugal.


She tells me that she followed the budget, I’m not sure I believe her. But what did happen was that she got the promotion. With her new higher salary starting in October she was able to transfer all the extra income straight into the savings account.

The months ticked by, the 1st March got steadily closer and apart from a slowly bloating savings account nothing much changed.

Choosing What To Do For A Living

We floated quite a few ideas of ways she could make money online. I suggested she should do some food-related video blogging. She said she knew nothing at all about that and wanted to do something she was sure she would be good at.

At PwC Emma had worked in marketing and was pretty awesome at it. So it made complete sense to try and start something that used the same skills. Freelancing was the obvious choice.

She dug around and found some freelancing sites (Upwork, Freelancer, People Per Hour) all of which were full of people trying to sell their marketing skills.

But that’s the thing about these freelancing sites. There are thousands of people on there, but often it is hard to find any quality among all the terrible profiles. I have posted jobs before and got absolutely zero replies from anyone who seemed competent. Lots of copy and paste responses, or ‘teams’ out in India who couldn’t speak English. But nothing I would want to spend money on.

Here is a screenshot from the last job I posted – it was to do some small SEO work on this site. There were 27 applications and not a single one had even looked at the site!

Emma’s strategy would be different. She wouldn’t compete on price, she would compete on quality. She would only apply for projects she thought she would be well suited for and then in the application she would write something that made it clear she had read the posting. Then if she got the contract she would do an awesome job.

She set her hourly rate at £50/$75 with the plan to raise it once she had built up a decent portfolio and client network.

The only issue was that she couldn’t start right away. It would be a breach of her contract to start doing marketing for anyone else before she had officially left PwC. All she could do was wait.

Escape and Burnout

The 1st of March arrived. Emma launched her Upwork profile, turned on her website and updated her LinkedIn. And even before we got on the plane she had been offered a job.

Updating the LinkedIn had sent notifications to all her connections and one of them got in contact. They were a friend of a friend that Emma barely knew who worked in the private healthcare industry and they were looking for a marketing expert on a monthly retainer. He would pay the full rate, the job looked right up her street and we were heading to a part of the world with a fraction of the cost of living.

That’s when it all fell apart.

Our first stop was a hostel in Buenos Aires. We were staying in shared dorm rooms that were full of people in their twenties or thirties who had taken a year or two off work to travel. Their only responsibility was to have as much fun as possible.

While everyone else was snoring off their hangovers on our third day there, Emma was up at 6am on the phone to a supplier who was late delivering some branded portable phone chargers. She hated it. She was burnt out from years of corporate life and her first taste of being her own boss was awful.

We soon left the hostel and moved to accommodation more conducive to getting work done. But the tone had been set.

Emma quit that first job and decided to have a holiday to create a break between finishing work and her new life. She wasn’t herself.  She was trying to get accustomed a new lifestyle and a new job at the same time, and failed.

We spent the next three months traveling around South America. I kept up with my work, taking the occasional day or two off to work. And Emma did, almost nothing…

About six weeks in she decided to start again.

She perfected her strategy for Upwork. Instead of spending ages on each application, She would use a template response but would personalise it slightly for every job she applied for. Spending a few minutes extra on each proposal but still being able to apply to loads of different jobs in a short space of time. We did a two-day binge and she got back quite a few responses.

But then we got on a plane to the desert and her laptop didn’t work with all the dust and sand and the next thing you know she hadn’t opened her laptop for another six weeks.

Here’s Emma on Mole beach in Brazil not doing much work:


The Fear – The Motivating Effect of Running Out Of Money

“I describe Freelancer as like online dating. You spend a lot of time applying for jobs and don’t hear back from most.” – Emma

Just like a university student leaving their essay to the day before it is due in, Emma left really settling into work until her credit card bill was higher than the money remaining in her account.

She left it too late. And although she actually started doing some work, it wasn’t enough and she went into her overdraft.

Her rate was quite high and her cost of living was much lower than before leaving London, but it still took a lot of time to apply for jobs. She had to wade through lots of time wasters and was held back by having no hours or reviews on her Upwork profile.

She did a few cheap job for friends and got a few clients from LinkedIn. Slowly the money started to scrape in.

Plus the tactic of sending a lot of personalised templates applications, seemed to be working:


That email was from a company that creates beauty products. Emma had looked on their Instagram and followed it. Plus she included in her application that we had tried one of the ingredients while in Brazil. Not exactly a lot of work on her behalf, but look at the result.

But even so, most applications still went ignored. She was spending more time applying for jobs than actually doing them and was left in debt.

Turning a Profit

Over the next few months, Emma and I continued traveling and in August we got engaged. We went to Spain, Hungary, Croatia, Ireland. And all the while she got more and more into her work.

This is not the engagement pick, but it is about the same level of happiness.


Emma finished some jobs, got good feedback, got repeat work. Got better at her pitches. And got offered more work.

She went from increasing her overdraft each month to staying level and finally to earning more than she spends.

The constant applying to jobs started to pay off and she got offered larger and larger contracts:


She was also working on some really interesting jobs.

Promoting a wine business from Napa Valley, a beauty range from Australia and a technology startup from silicon valley. The work she was doing was not only on her own terms but also very interesting.

Firing A Client

And then she had an experience that you can only ever get when you are your own boss. She fired a client.

She was working on a new contract she had found through LinkedIn and had only done one days worth of work. Then out of the blue, at 9pm, Emma and the other freelancers all received the same email. It said they each hadn’t worked hard enough and demanding an extra days worth of work for free.

Emma knew she had over-delivered and most importantly she knew she didn’t have to put up with such behavior. She had more offers from clients than she needed and so replied with a polite email saying it wasn’t going to work out and walked away.

When you work for a big corporate you are entirely at the mercy of whoever is chosen to be your boss. If you don’t like it your only choice is to quit. You have to start again from scratch, or suck it up and put up with it.

For Emma, that moment made the previous eight months of rejections, burnout and stress of having no money all worthwhile.

Her plan now is to work roughly 15-30 hours a week and spend the rest of the time living her life: doing wedding admin, traveling and spending more time with her friends and family.

Shameless Plug

If you want to hire Emma then you can contact her on her Upwork profile. She’s awesome at marketing and I expect she’ll be upping her rates at some point so get in there soon!

If you have any questions for Emma then post them in the comments and I’ll ask her to reply.