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Okay, I’ll admit it: I believed the freelance hype.

I thought that when I worked for myself I’d be in the office just a few hours a day, take long breaks and earn big bucks.

Well, that never happened.

Instead it’s been a sometimes painful walk down struggle street, with long hours, zero holidays, and a bank balance emptier than Donald Trump’s soul.

Until now.

“I just had to have a stern word with my boss and make her understand the break was achievable and would benefit my business in the long run.”

Why? Because I’m about to embark on a break from business: 49 client-crisis-clear days; seven sweet, work-free weeks; two months away from my cage desk.

In this article I’m going to share how I made it happen:

1. Diversifying

As a copywriter, I provide a service that relies pretty much on me and only me.

So when I don’t work, I don’t earn money.

At the start of the year I decided it would be sensible to create some products I could sell all year round.

I set up a now highly successful ecourse that runs four times a year and tops up my income for several months, as well as a shop selling virtual products to provide regular income.

There was a huge amount of work involved in setting these up, but now I’m reaping the rewards.

2. Outsourcing

I’ve always loathed managing big teams of people, so as a solopreneur I’ve never wanted to employ staff.

Instead I outsource the work to other solopreneurs.

Accepting the need to delegate is a tough change.

But now I happily hand work off to others, including a designer, accountant, proofreader, editor, developer and digital assistant.

They’re experts at what they do, so they work through things faster than I ever could, leaving me to focus on what I do best.

During my seven-week break, I’ll be asking my digital assistant to keep an eye on things, tackle some housekeeping style tasks, and get in touch if anything big crops up.

3. Automation confessions of a misfit entrepreneur with Kate Toon

This year I’ve made the move to automate and simplify my processes using applications.

Yes, I took a hit on the initial investment of these subscriptions, but it’s paying off in buckets.

I use Xero to manage my accounts in a few clicks, Basecamp to keep projects on track, Mailchimp to send autoresponders, and a veritable army of plugins on my five websites to ensure everything happens without much need for human intervention.

4. Scheduling

I spent some serious time creating social media updates to see me through the next few months.

I also worked back through all 200 or so of my blog posts to refresh and revamp them so they’re ready for republishing.

I use Hootsuite to schedule posts ahead of time.

All this will keep a steady flow of traffic to my site while I’m away, and provide a fresh crop of potential customers when I come back in January.

5. Referring

Obviously, while I’m away I may still get enquiries.

So rather than ask them to wait until my return, I’ve set up a referral network of other copywriters through a low-cost, paid community.

I can pass the leads on to great newbie writers while also earning a little cash as they sign up for community membership.

6. Financial planning

It’s been a good year. With my regular copy-writing work, passive income sources and large upsurges in cash from my e-course, I’m already pretty set.

But I’ve also planned out some client payments as well.

Since I charge a 50% deposit with a further 50% due after delivery, I’ll have some juicy down payments and some welcome final payments plopping into my accounts while I’m on holiday.

7. Hard work

I’ve worked damn hard in the run-up to this break.

I’ve been pushing myself to squeeze in a few extra hours wherever possible and motivating myself to keep going, even when I’d rather slump on the sofa and pour wine down my neck.

But for me the payoff has been worth it.

The fact I’m giving myself this long break makes me feel like I really am now living the freelance dream.

To get such a long break in a real job would require some kind of long service slavery agreement.

But I just had to have a stern word with my boss and make her understand the break was achievable and would benefit my business in the long run.

The challenge ahead will be to actually step away from my computer.

I’m hoping the longer break will give me some much needed de-stress time, perspective and renewed energy.

No doubt I’ll sneak in a few hours here and there. But that’s fine, because I truly love what I do.

I promise to report back after the seven weeks to let you know how it went, and how it benefited my business.

And now, over to you: Have you ever managed to take a long break? How did you make it happen?

Did you like this post?

confessions of a misfit entrepreneur with Kate Toon

You might like my book ‘Confessions of a Misfit Entrepreneur | How to succeed despite yourself’ – buy it online here.


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This post originally appeared on The Flying Solo website.

I’m taking a seven-week break from my business. Here’s how. was last modified: by