Preparing for your Holiday as a Freelancer

The foreign holiday: the only thing I look forward to more is Christmas. The excitement of visiting somewhere new, experiencing food and culture, or even visiting somewhere I’ve been before on a well-earned break is a highlight of my year. About this time last year, I went to the Greek island of Rhodes.

This year, I visited somewhere I’d never been before but still in Greece: Chania in Crete. Let me show off my not-as-good-as-I’d-like Greek skills and write that in its mother tongue – Χανιά. To avoid frustration, getting pestered and all the other things that remind you of work, this is how you can prepare for a stress-free holiday as a freelancer.

Client Early Warning System

Let your ongoing clients know as early as possible and send multiple reminders. With every first communication this September, I let each client know the dates I would not be around. A month is a good period of time with a reminder of two weeks before. Let them know when you leave, when you are back, and what you are likely able to produce for them up to and straight after these dates. Keep reminding them if you need to but I find that 2-3 reminders are enough.

Plan, Plan, Plan and Plan Again

By now, you should know what you can manage in a typical week. Planning your work before you go and after you return (particularly if the holiday begins mid-week as mine did – we had a Tuesday 1pm flight) will save you stress. Fail to plan, plan to fail and nobody wants to fail at taking holidays. Split work, refuse work and renegotiate deadlines. Also, don’t forget to schedule time for all the last minute preparation. You are always going to overestimate what you can do. The packing I did on Monday meant I could not do as much work which I had to reschedule for my return.

Don’t Take on Too Much

Work that needs doing, needs doing… and by you. That’s one of the downsides of being a freelancer but it need not be that way. If like me, you have multiple clients, it’s prudent to go against your natural instinct to keep looking for new work right up to your break and earn as much money as possible ahead of it. The problem is, you will give yourself too much. Focus on consolidating what you have. If you find you have spare time to do more, do extra work for an existing client rather than seeking new work. We get into the mind-set of being away from our desk means a client will seek new freelancers (permanent ones) but it’s not true. Any client who does probably isn’t worth the relationship anyway.

Upwork Specific #1: Set Unavailable Status

This should go without saying, but if you don’t want to receive the email ping of an invitation to interview while you’re sunning yourself on a beach or taking in the breathtaking view of an archaeological site or natural landscape, set your status to unavailable. You’ll thank yourself later.

Copyright MG Mason 2017

Upwork Specific #2: Stop Applying for Work

Similar to the “don’t take on too much” point above which was more about existing clients, you should get yourself out of the habit for a couple of days of scouring the Upwork jobs list. Don’t get sucked into FOMO, or you’ll stress yourself out for your holiday.

With that, let me wish you a wonderful break no matter where you are heading!

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