Behind the Press | Tips on Taking Time Off for the Self-Employed

Vacations For The Self Employed | Sycamore Street Press Blog | Photos by Jacinta Moore

Behind The Press is a blog series by SSP’s owners: Eva and Kirk Jorgensen. In it, we share our experience with letterpress, paper goods, running a small business, and work/life balance in the form of tips, how to’s, and more. We hope you enjoy! – K&E

The other day, I posted about some of my hits and misses in taking time off since I started Sycamore Street Press. I’m interested to see how other small business owners take to the issue, so I wrote a few of my friends and family members who work for themselves, and asked for their thoughts or tips:

Kris Pollock (my dad), owner of Jupiter Electric, an electrical contracting company in Heber, UT:

So many people can just walk out the door at the end of the day and not have to worry about work until the next morning. Or at the end of their vacation. But you and I and Kirk can’t do that. It’s something that we always have to think about. I lose sleep over work. It’s always with me. Even when I went to Norway, I was on the phone bidding jobs. But I do it for my family, I love my job, and I wouldn’t change what I’m doing, that’s for sure. 

Julie & Matt Walker, owners of Tiger in a Jar, a film production company based in Salt Lake City, UT

1) Since we are pretty exhausted between our shoots we aren’t really up for running across town to hit up a major sight, so instead we try to take walks around the part of town we are in. We often stumble across really amazing bakeries, shops, or landmarks and we love that it is our own little adventure that doesn’t leave us worn out.

2) We try to make travel time like flights, train rides, taxi rides, etc. as productive as we can so that when we get to our destination we have a bit of extra time to explore.

3) Mostly we feel like it boils down to attitude. If we constantly keep our eyes open to appreciating where we are we end up having a wonderful trip, even if we do end up behind the camera most of the time.

Brittany Watson Jepsen, stylist, designer, crafter, and founder of the House That Lars Built, a design and lifestyle blog from Copenhagen (soon to be Provo, UT):

I don’t think I ever take a real “vacation” where I’m not doing at least some type of “work”, whether that be checking emails or taking pictures for the blog or thinking about a blog post. I think it’s a part of the job of a freelancer because social media is like interest: it never sleeps. There’s always something going on that you need to be aware of. That said, the beauty of being a freelancer in that I can plan my own schedule, but it’s also the downfall because there’s always something to do. I think the best advice I can offer is to plan ahead so that you can schedule your work around the specific time period. Make sure your clients know your schedule and stick with it.

Erin Austin Abbot, owner of Amelia, an brick and mortar (and online) shop in Oxford, MS:

When I decided to open up my brick and mortar, I knew I wouldn’t have anyone giving me days off anymore. It was going to be up to myself to find the balance of work and knowing when to slow down and take much needed time off. Closing means a loss of sales, but without rest, what good are you? So, from the beginning, I established that I would be closed two weeks after Christmas and two weeks in the middle of the summer. My customers know that the online store is up and running then so they can still shop and I’m able to relax and focus on my family. And maybe even get out of town for a real vacation.

Leland Rowley, owner of Rowley Press, a letterpress studio in Provo, UT:

Vacation? Huh? I think for me a lot of the time my vacation comes split up throughout the year. Sleep in one morning, go hiking while all the other suckers are at their 9-5 (of course I will be working till 11pm, but whatever…), or spend a day foraging. The flexibility of schedule on a day-to-day basis is like living everyday on vacation. Well, sort of.  When large blocks of time do arise, I most assuredly end up working. I have to focus on the fact that I may be working, but I am working from Disneyland or wherever. Sometimes I try to just turn off my phone and not check email, but that can be dangerous. Unhappy customers would make for a very unhappy vacation. 

Sarah, owner of Sarah Jane Studios, a children’s lifestyle brand based in Provo, UT:

1) Have very clear expectations with you are traveling with. Is this a family getaway?  A business trip? totally makes a difference. Here’s my 2 cents: 

FAMILY TRIP: set clear expectations with your traveling partners. Have a set time when you will work, allow for ample play time, and make sure that when you are not working, you aren’t thinking about working. My father was self employed for 10 years and he always worked at 5am every morning until 9am when every one else woke. We never knew he was working while on vacation. It meant the world to us as a family. As for me, I’ve tried to do big blitzes where I try and get as much done as I can in a big chunk, and then remain care free the rest of the time. 

2) If you can avoid working, avoid it. Plan blog posts ahead of time, clear your inbox, put a notice in your inbox about when you will return, etc. Being self employed means it’s REALLY hard to disconnect, which means it’s even more important to try and disconnect and just let it all go every once in a while. You’ll be better off for it. 

3) Get inspired. Getting away can revitalize you in ways you weren’t expecting. Be open to new ways of thinking, keep a journal, and enjoy the time you have to take a step away and get inspired. 

Margaret Haas, owner of Paper Pastries, a paper goods company and online boutique in LA, CA

1) Be prepared to go on vacation. Long gone are the days when I could pack up a bag and just take off on a whim. Now that I run a business, I make sure to wrap up all outstanding orders before I leave town. If a project is more involved, figure out a timeline that works for both the client and I.  You won’t be able to relax if you’re wondering “Did I get that rush order out on time?” Be sure!

2) Don’t check your email. I’d recommend putting your email on vacation mode. State the days you’ll be out of the office and that all outstanding orders have been shipped. 

3) Jump right back in. You might feel a bit guilty while you’re supposed to be having fun. To get rid of that feeling, I sometimes have to make a long list of things I’ll do when I get back. Just looking at that list makes me wish I was on vacation-and guess what- I am! Then I put the list away and get back to having fun.  But beware- it’s easy to get used to sleeping in and not checking your email. Pull out that list on your last night of vacation and think of how productive you’ll be when you return. The best motivation for me to get back to work? The more I work now, the faster the time will pass until my next vacation! 

4) Get a massage. If you’re the type of person who likes getting a massage, there’s no better time than while you’re on vacation. Because I work with my hands all day, my back aches and my arms get sore. Last holiday season, during all of the craziness I got a massage. All I did was feel guilty laying on that table- “I should be at work! What am I doing??” While on vacation, it’s the best. Because what else are you supposed to be doing but relaxing? 

Sarah Winward, owner of Honey of a Thousand Flowers, a floral company in Salt Lake City, UT: 

For me the hardest part about taking time off while self employed is…doing it!

I think that it is likely that anyone who works for themselves is driven, and in general, I think we all have a hard time putting the computer away each night (and weekend, and holiday). I’ve found that if I schedule my vacation time really far ahead of time that I just stress about how much work I will be missing on that time off.  I wish I could look forward to it! But for me it seems that when you and you only are in charge of how much work you take on and how much money you make, its hard to just decide to stop working.

So my advice…

Is to just bite the bullet, and give yourself time off.  I have such a hard time scheduling time off for myself, but when I do I always come back refreshed, inspired, and more productive than I was before. My job is much busier in the summer than it is in the winter, so I always have the winter to look forward to for some relaxation.  In the summer I work 19 hour days about 3 days a week, and regular 8 hour days for the other 3-4.  If I don’t take a bit of time mid-summer to escape, I begin to loose my mind, and I lose touch of the fact that I love my job. While I am taking time off I am often out in nature and I fall in love again with wild flowers and trees and all of the things that make me love my job in the first place.

This last one is a quote that I posted on the blog a couple of years back. I still think it’s interesting.

Chris Guillebeau, entrepreneurial writer, from his book the Art of Non-Conformity:

It’s always fun to go on vacation as a self-employed person, because a) you still have to work, and b) no one thinks you do any work to begin with. So then when you go on vacation, they say, oh, must be nice that you don’t have a job and can do that. Meanwhile on vacation I work six hours a day instead of ten. But it’s all good.

Do you have any tips for figuring out this catch-22 or just thoughts about it in general? I’d love to hear!

All Photos by Jacinta Moore. She took them while floating off the coast of Cinque Terra in Italy. Looks so gorgeous and relaxing, doesn’t it? You can purchase affordable prints of these photos and more in her shop Bawk Bawk.

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  1. Wonderful, wonderful post, Eva! Thanks for sharing these helpful tips we can all use – especially this time of year! Wishing you many vacations in the future. :)

  2. LOVED this post. laugh out loud at chris’s line at the end. so true. my friends are always sending me job listings. i’m like, dude, i work full-time! :)

    • Eva says:

      Sending you job listings?! Ha ha! I know, I think a lot of people who haven’t worked for themselves think that we self-employed people must not really be working. :)

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