An Entrepreneur’s Guide to A Real Vacation

There are so many benefits to being self-employed--to being your own boss(lady)--and among the top of the list when folks make the leap is having a “flexible schedule.”  One of the benefits of working within a formal structure (i.e., for a company, organization, etc.) is Paid Time Off.  You may be thinking, “well, duh.”  Here’s the thing about PTO--even if you don’t take it, it’s a structure that’s there for you.  People within your organization know what it means when you are OOO.  There’s a culture inherent in the organization about how people behave when they are OOO.

All of that is up to you when you are your own boss.  You have to create your own culture, your own structures.  And to be honest, this kind of irritated me when it came to taking time off, so of course I didn’t do it super well for a long time.  Finally, I gave myself a pep talk and tackled the problem the way I would for a client, I analyzed the pain points and came up with a plan.  And you know what?  It worked.  Here’s what I did.

Part 1:  The planning ahead part

This may be the tough part.  You’ll need to lay some groundwork way ahead of your actual vacation.  This looks like anticipating and blocking off time on your calendar months in advance.  If you have a team, include them on that calendar invitation when you block the time and ask them to help you protect that time.  It also looks like recruiting some talented folks to serve as backup for your continuous tasks, and training and empower them to respond while you are away/offline.  Explain to them exactly what you need, and under what circumstances you want to be contacted if needed.

Part 2:  Setting expectations

This one is dependent upon your own work flow and clients.  For me, it involved a few things:

1. When a client asked me to take on a new project just before the time of my vacation, I let them know I’d be away and could start the project when I returned.  They were fine with this.

2. About a month ahead of time, I sent an out of office calendar notification to my regular client with whom I normally have daily interactions.

3. For existing clients and projects with regular weekly meetings, I gave them 2-4 weeks notice that I’d be away and not available for meetings.

4. Finally, for a client with whom I normally have daily interactions and deliverables, three days before my vacation began I sent out the following message (feel free to adapt)!:

Starting this Friday at Noon Eastern, I'll be on vacation.  In the interest of transparency, I'm sharing what you can expect while I'm out.  I'll return to work on Monday.   During this time, I won't be reading or responding to emails, Wrike tasks, Slack notifications, Monday.com tasks, or Teams messages.  I'd really appreciate it if you refrain from sending me messages while I'm away, whenever possible.

 You can expect that the tasks I normally do on a weekly basis will be completed by EOD this Thursday, with the exception of the weekly notification of registrations.  If you need something from me, please do your best to submit that request by Thursday morning so I have time to complete your request. 

 If you find you need something from, A,B, C and D all have instructions on how to do the things I normally do.  A will also know how to get a hold of me in case of emergency.  B will be covering the meetings I normally run.

 Thanks for honoring my boundaries, and for all you'll do on the work front to support this much needed break.

 Part 3:  Honor Your Boundaries and Disconnect

This part is very personal.  If you will answer or be distracted by the messages, take your email off of your mobile device.  Use the tools you have to post out of office notifications, and consider turning off your calendar notifications too.

I’ve even been known to go to a place with limited or no internet access--as you might imagine this is increasingly harder to find and not 100% necessary.  You might consider limiting your social media usage--think about what will give you the opportunity to fully rest and recharge.

Here’s the OOO message I used:

Hello!

Starting Friday at Noon Eastern, I'll be on vacation and will return to work on the following Monday.   During this time, I won't be reading or responding to emails, Wrike tasks, Slack notifications, Monday.com tasks, or Teams messages.

If you need assistance or would like to make an appointment with me, please send a note to my awesome assistant A at [insert email] and they'll do their best to help.

Thanks for honoring my boundaries, and for supporting this much needed break.

With all of this in place, I was absolutely able to disconnect from work and enjoy my vacation. Just about everyone honored the boundaries…and everything is just fine business wise.