Why putting the Out Of Office on can be SO hard

When you’re freelance or self employed, properly going on holiday is a hard thing to do.  There’s a worry that, as you do everything in your business, things might fall apart if you’re not keeping on top of messages and emails.  There’s also the more uncomfortable thing that you get validation and a small dopamine hit from emails landing in your inbox telling you you’ve gained a new client/customer or from someone looking to collaborate.  Stopping that is hard, even if for only a week.

I’ve been either freelance or leading small organisations (where funding is just as precarious) for all my working life.  It's made me a master of dealing with uncertainty but it's made me truly dreadful at using my Out Of Office email function for my businesses.

Part of me envies those gainfully employed, paid by a company the same amount every month and given an annual leave allocation.  When someone else has to OK your annual leave, it makes it easier to take it.  As does (relatively) predictable income.

A bigger part of me would not swap my vibrant, varied and exciting work life for an employed role.  Any employed role.  I LOVE working for myself.  I love being in charge of my own schedule and I delight in how few useless meetings I need to attend these days or time consuming silly bureaucracy.  But despite being master of my own calendar, booking a "proper" holiday feels an ultra risky move.

I've built a business that relishes being responsive and reactive.  Which also means it is hard to predict income more than three months in advance (sometimes only a month).  I regularly remind myself that it always pans out and I've done a huge amount of work on shifting my mindset so I don't keep panicking and spending hours scanning job pages for jobs I don't want.  In general it's fine and worth the gamble, but booking a holiday was one hell of a hump to get over.  How can I commit to that expense, plus taking time out of my business a few months in advance?

As a single mum with a successful but precarious business, summer holidays have always been hard.  They go on for ever and some years I’ve not had the funds for a decent holiday.  Also when I did have the means, taking kids away solo can also take it out of you.  It can be really hard.  Mine are 12 and 15 now, so it is much easier to go away - they can carry suitcases for a start!

With that in mind, this year, I did it.  As the schools broke up at the end of June (as they do in Scotland), my kids and I whisked off to Dubrovnik for a week and it was wonderful.  The hotel exceeded expectations (which is a very rare thing), it was gloriously sunny and we had a seaview balcony with the most stunning sunsets each day.  It was also, unexpectedly, very expensive.  Croatia gained the Euro this year and that, along with the other cost of living crisis issues and the everlasting popularity of Game of Thrones (Kings Landing = Dubrovnik Old Town) meant that prices had whooshed sky high. 

Now I'm in an interesting predicament.  I purposely made July less busy so I could go on that ever so special holiday, plus another trip to see family over in Ireland.  There are less emails in the inbox and less things on the to do list.  And it feels extremely uncomfortable.

But I chose this!

If I’m being honest with myself, it’s uncomfortable because of that buzz when I get an email about new work, or when I have a zoom with a client, or I’ve got a big juicy project on the go.  Right now (because I chose to make July quieter) I don’t have this and it’s really, really hard not to panic.

Part of that panic is because our lovely holiday cost more than I predicted, so there’s a bit of 0% credit card fun to address.  There’s 19 months to sort that out though. 

Also, the reason I’ve got time to panic and feel uncomfortable is because my kids have become much more independent.  Covid played a role in delaying the development of this, and it seems all of a sudden they are making plans and heading out to do stuff.  Which is absolutely great: they’re both at an age where they should be doing things independently and going out exploring.  But it has happened all of a sudden and has left me reeling a bit and realising that perhaps I didn’t need to slow July down quite as much as I did.  Lesson learned!

When I’m not in panic or uncomfortable modes, there is something really interesting in having more of a laissez faire attitude to work.  I am still making progress.  Things are still getting ticked off the to do list, but it feels so much more drifty than usual.  It also feels really good: like I’ve kept a bit of the holiday chilled out-ness and taken it into my business.

Whilst it’s always fab to have a bit of fire in the belly and to sometimes hit the ground running, I think there’s lots to learn about being laissez faire.  I’m giving myself a little mini challenge to keep that going as long as possible.  If I could achieve that through the summer and up until the end of September, that would be amazing!

How does my story compare with your approach to summer?  Ping me a message to let me know and we can compare notes… in a chilled out spacious kind of way!