Lifestyle business

Love it and leave it – how to take extended leave from your business

- December 21, 2016 5 MIN READ

I love my work. But I love holidays more. Here’s how I set up my business to take extended leave in 2016 … and in the future too.

Recently, I took four month’s ‘long-service leave’ from my five-year-old micro business. It took a couple of years to get off the ground but the effort and expense were worth it. On reflection, I think the process can be summarised into six steps: dream, trust, plan, trial, leave and re-enter.

Step 1: Dream

Like many entrepreneurs, my business evolved from the skills, experience and passions I’d developed over the years. Once I took my business online, it grew so quickly I had to ask prospective clients to wait months for me to start work on their projects. A good problem to have but still a problem! So I sought other experienced writers and editors with a strong work ethic to help me out. Within a couple of years, I had five contract staff happily quoting on work under my brand for jobs I couldn’t do (either through lack of time or experience). I like them and trust them. We’ve become a loose ‘team’.

But matching five part-time contractors to the right jobs takes time; time away from the writing, editing and story coaching that I dearly love. So I began to look for someone to wrangle us. I figured this role was key to enabling my distant dream of taking long-service leave, someday.

Step 2: Trust

It took a while to find the right person. I searched the Virtual Assistant world but decided I needed a closer relationship to the person. I came across someone who seemed just right and trialled him while I took three weeks’ leave. Upon my return I discovered systems working wonderfully but some people (staff and clients) less than happy with his treatment of them. He was not right for the job.

Creating a position description and a set of criteria helped guide me towards who I was looking for. Not having interviewed anyone and rarely been interviewed myself, it took me a while to realise this could be a useful tool!

Finally, I found Alina, named her Creative and Administration Support, employed her for three days per week, and got on with the business of training her in what had become ‘writing, editing and story coaching according to Ann Bolch et al.’.

Alina dragged lots of information out of my head, set up much-needed systems and began to learn the highly personalised and specific services that we deliver. (For example, we don’t have an automated reply to initial email queries because on any given day we might be asked to quote for work as varied as editing a series of technical blogs, interviewing for a family memoir or ghost-writing a business book.)

After Alina and I had been working together for just a few months, a gap opened in my husband’s work. He could take his long-service leave in 2016! By now I trusted Alina. With such a close working relationship, we knew each other well. Indeed, we had already worked through some tricky matters. Most importantly, I was sure that the skills she still needed to develop to run the show in my absence would come.

But would she want to take on the challenge?

To my relief, she said ‘yes!’

Step 3: Plan

In mid-January, I booked a flight for Istanbul for the middle of June. Alina and I had five months to get everything in place.

By February we were starting to get used to our CRM system. (Previously the ‘CRM’ had been made up of email trails and my head.)

By March I knew what my larger clients would need from me in my absence. Graciously, they joked, ‘For you not to go!’ I started to train other staff in the work that needed to get done.

By April our invoicing ‘system’ was still a bit of a challenge and we narrowed the problem down to occasional and random intervention from me. I started to realise that some of Alina’s work would be easier with me not around!

By May Alina’s capacity to reply to initial queries was improving. She was faster and demonstrated increased understanding about what to ask when, and why she was asking it. This secured effective briefs from our prospective clients to transfer to the best staff member for the job. This, of course, helped devise a fair and accurate quote in short time.

Throughout the months, I briefed Alina on everything I could think of and asked the contractors to support her in my absence.

Step 4: Trial

During May we transferred my responsibilities to Alina with me being on hand to observe communication between her and clients or staff. She asked questions, I gave feedback and we discussed how we might improve. (And I do mean ‘we’. As a solopreneur I have largely set up this operation from scratch and am happy to learn if there is a better way to go about things.)

This trial period was a great opportunity to go through our CRM and read about every client since inception, check their notes were up to date and talk about who might come back, what for and who would be the best person to work with them in my absence. This became a sort of a test for Alina. I’d say, ‘This is what they’ve needed in the past – who from the team would service them well?’

Alina takes feedback well so learns quickly. She’s also not afraid to push back if she thinks I’ve got it wrong. She asks good questions. So by the end of the first week in June, we had completed a thorough and timely handover that hadn’t felt rushed. Which is a good thing because that last week of work and the few days’ packing before I left was rushed!

Step 5: Leave!

They don’t call it ‘leave’ for nothing. After trialling Skype, messenger, Dropbox, email, text and phone, it really was time to go!

Throughout the four-month holiday people often asked, ‘Did you find it hard to let go?’ It would’ve been fair to reply with a yes. I had nurtured the business from a thought bubble to this. In reality, however, my short answer was, no.

I’d dreamt. We’d planned and trialled, planned and trialled. Now I had to leave and let the rest play out.

And it did! We discussed the amount and timing of communication we’d both like while I was away. The truth was we didn’t really know. As a starting point we scheduled weekly calls on a Wednesday. If weekly Wednesdays were the best way to continue for the entire 14 weeks, this would be a small price to pay for my being away for that long. If, however, there seemed no need to chat on any given week, we’d let it go and see how that felt, and if that felt about right, we’d talk on an as-needs basis.

After two weeks, we were emailing, texting or speaking only as needed. And there was need. I was pleased to advise on or deal with the two incidents that Alina referred me to, even though I had to postpone dealing with the first until I’d recovered from a sorry bout of Turkish gastro!

Step 6: Re-enter, carefully

Return, if you must! But remember, the longer you’ve been away the more the business will have shifted, developed, grown in your absence.

While I was away, my business serviced over twenty new clients and maintained relationships with all existing clients. A new website was formatted. A marketing strategy began. Fortnightly blogs were written and published. Clients were invoiced. Billers were paid. Staff reported enjoying working with Alina and she felt generously supported by them.

A few commas had been used incorrectly. Some serious jargon was introduced to the marketing strategy. Post-holiday, incoming work is slow. But the latter might be due to the fact that I rushed a quote during the last days of my holiday because I had to go Le Louvre. Chatting later by phone, Alina thought I had rushed off to the loo …

Poor phone line aside, planning your return can be difficult. Here’s a tip – make the last part of your extended leave really dull so it’s easier to go back to work!


So, that’s how I managed to have four months’ long-service leave where I can truly say I hardly thought about work. I dreamt, I trusted, I planned. I trialled and left and returned. A once in a lifetime opportunity?

Perhaps not. Just imagine …  if I can average four months’ leave every five years, that’s quite a bit higher than legislated long-service leave! Hmmm, where to in 2021?

Have you ever managed to take extended leave from your business? How did you set things up?