How to take a real vacation when you’re self-employed

I like to take a real vacation every year. I try to book one month off consecutively, usually in August. It’s the best month for hiking and camping locally, my husband is off work (he’s a teacher) and our clients are often on their own vacations.

For some entrepreneurs this can be a big challenge, since they feel like they can never quite get away. One of the goals I set when I started Backyard Creative (nearly a decade ago!) was to design a healthy workplace for myself. I’ve learned that to stay inspired and energized, I need time away to collect my creative thoughts—time to really take a break and forget about work. Since scheduling my own breaks is one of the perks of self-employment (often envied but rarely used!) I want to share with you what I’ve learned about taking a vacation, in case you’re feeling inspired to plan your own as you look forward into the new year.

Plan ahead

Put your vacation in your calendar well in advance, and I don’t mean a couple weeks out. Try blocking out vacations at the beginning of the year. Talk to your family and decide what’s going to work for you. This is easiest to do when there’s nothing in your calendar to begin with (hence planning way in advance).

Another thing you’ll want to plan ahead are your finances. The most common thing people say to me about my being self employed is, “That must be so nice, you can take a vacation whenever you want!” Although this is technically true, in practice it’s very challenging to actually get away, especially when no one’s paying you to go on vacation. So plan to pay yourself for that month off, so your finances are not a deterrent for taking time away.

Tell everyone

Once you’ve committed to some away dates, start telling people. Share the news with your collaborators (“FYI, I’m going to be away from July 1 to July 31, we’re going to Portugal!”) and with your clients. Throw it in your email signature, or bring it up in a new business meeting.

Starting this conversation well in advance of your vacation is key. To be as considerate as possible, I think people need at least six months’ notice. Obviously, this depends on your current client commitments. Whether you decide to give people six weeks or six months, make sure everyone is clear that you’re going away, especially if there’s new work being discussed. That way, there will still be enough time to ensure the work can fit around your away dates.

Now this is the hard part: don’t feel bad about, or apologize for, your vacation! As a self-employed person, you need to create your own dream job. Waiting for natural down time might work for some people, but in my experience, it’s way too easy to get busy and forget to prioritize myself and my needs. And I also know that not putting myself first is the fastest path to burnout!

Rely on others

One of the reasons I can disconnect is because I’ve built a team of collaborators that I trust. Sometimes I’ll plan to have project work end before I leave. Or, I’ll leave a project with one of our designers or project managers and let them continue on in my absence, knowing our clients are in good hands.

This approach doesn’t work well with new creative, as I always like to be intimately involved in getting projects off the ground. However, it’s effective for a production phase, when the concept or creative direction has already been approved. Planning in advance is, once again, the key to success in this scenario, and I love that our work doesn’t need to come to a halt just because I need a break.

Go and actually disconnect

After backing up everything on our shared server and confirming everyone has what they need from me, the last thing I do before going on vacation is turn on my email auto-responder. I’ll set my away message to notify folks about my vacation dates, and provide contact details for my point person (usually Madelen) for urgent or time-sensitive inquiries. I let my point person know how to reach me if something truly needs my attention, and I turn off my computer and leave it in the office. I usually do have my phone with me, so I can jump into a Slack channel discussion if needed, or check email if something unexpected comes up.

So far, my vacations have been mostly interruption-free, since our clients and collaborators truly respect my down time, and they’ve contacted me only when there’s been an emergency of sorts (or an amazing opportunity that we needed to jump on!). Aside from that, I try to stay offline, focus on where I am and allow my brain to take a real break.

It usually takes me the better part of a week to just let go of everything, and then it’s the following three weeks that really feel like a vacation. Coming back to my work and life after a month away, I feel refreshed, reenergized and re-inspired—and that’s well worth the effort it took to go away.

I’m often so surprised how quickly that month goes by, and sometimes nothing happens on a project while I’m away. Our clients get delayed for their own reasons (maybe their own vacations!), or they get busy. This is why you truly need to disconnect. After all the efforts to plan out your work and create the space in your schedule for a break, you just need to take it. Everything always turns out okay. Trust me, you won’t regret it the next time someone says to you, “Oh, it must be so nice that you can take a vacation whenever you want,” and you’ll be able to say, “Yes, yes I can”.