How to manage a long holiday despite being self-employed

Everybody needs a break from everyday working life at some point in order to relax a little and collect their thoughts again. For self-employed people, however, holidays often present a challenge. Especially solopreneurs are afraid of being unavailable and think they will lose customers and business.

But it is also possible to take a holiday on your own. To take the first hurdle costs an effort. But with a little preparation, it is also possible to take longer breaks when you are self-employed. For example, I personally take at least 3 weeks off once a year, even though my agency provides ongoing support for many clients.

Here are a few tips to help make a long holiday possible when you are self-employed:

Include holidays in financial planning

Holiday is time in which you cannot work as a self-employed person. Therefore you should take this into account in your financial planning. For example, if you want to take 4 weeks of holiday, you only have 11 months per year that can be used to earn your annual income.

Early planning

Early planning is important if you as a self-employed person intend to take a holiday for a longer period of time and can spend it relatively stress-free. Early planning usually allows you to plan your business around your holiday. You can schedule projects accordingly, find representatives and inform customers early.

Limit availability

Take a holiday to relax. This is only possible if you don’t check your e-mails and take phone calls all the time. If your business does not allow you to be completely unreachable, then strictly limit your availability and inform your customers about it.

One possibility is, for example, that you only check your e-mails every few days while on holiday and only answer those e-mails that do not have time until after the holiday. This requires discipline. But discipline can be learned.

It is also okay to completely switch off a communication channel. For example, you can tell your customers that you are not reachable by e-mail but that they can reach you at SMS/WhatsApp in emergencies.

Inform about the holiday

If nobody knows that you are on holiday or going on holiday, your daily business as a self-employed person will continue just as you are used to. You will not be able to relax.

Therefore inform your customers. If you are going on a longer trip, you should do so 1-2 months in advance. Then send another reminder email 1-2 weeks before you are going to be away, so that you can communicate with them and find out when you can still get things done.

It is also important to set up an out-of-office message in your e-mail account and on your answering machine. Communicate how long you are on holiday and when people can expect an answer. By the way, with some e-mail services it is also possible to create separate out-of-office messages for unknown and known contacts (i.e. customers).

The mobile office

In cases where you as a self-employed person have to remain partially reachable during your holidays and also have to react when necessary, it is important that you have a mobile office.

The most important tools here are a notebook suitable for travelling, as well as a pen and notebook. A good travel notebook is small, light and has a long battery life and is suitable for regular business tasks. The following models, for example, do a good job: Asus Zenbook, Samsung Galaxy Book

When booking accommodation you should of course make sure that there is WLAN in the hotel and that it is halfway fast. You can find this out quickly on most rating portals.

If you are travelling in non-western countries and are heavily dependent on certain online services, it is essential to check beforehand to what extent access to the Internet is restricted. This could mean that you cannot access services or can only access them indirectly (e.g. VPN).

Prepare or move tasks

As already mentioned, preparation before a holiday is important. If you know that certain tasks are due during your holiday and cannot be postponed, you can already prepare them to a large extent in many cases. If you have to write a report, for example, you can already pre-formulate the report at home and then fill it with the current data and finalize it during your holiday in a short time.

In the meantime, many tasks can also be automated. This is not only useful in the regular business routine, but is also valuable during your holiday.

However, most tasks can be postponed. Don’t underestimate the flexibility of your customers – after all, customers go on holiday too.


If you already employ staff, this can be a great advantage for holidays, as you can probably delegate many tasks completely.

If you are a solopreneur, you can also make mutual representation agreements with people who work in the same field as you and with whom you have a good relationship of trust.


Taking long holidays as a self-employed person is possible. But it requires good preparation and above all discipline! In this sense: I wish you a relaxed next holiday, which hopefully will last longer than a week.

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Christian Wagner
Christian Wagner
Founder RiskPlayWin | Owner & Founder of the digital marketing agencies &