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Can Entrepreneurs Take Time Off?

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One of the downsides to being an entrepreneur is finding the time to get away on a vacation and recharge. When you’re working for yourself, it can be hard to set boundaries. Most entrepreneurs I know are working pretty much all the time. Working from home can be a detriment in this case because you don’t even have to take your work home, it’s already there.

My parents owned a small Thai restaurant and they worked 7 days/week for years. They rarely took a day off and I don’t remember them taking a weeklong vacation at all. Before they had a restaurant, they were hourly employees and I remember taking trips to Yosemite and other national parks. Once they became business owners, vacations were a thing of the past. It’s tough when you’re working for yourself because you’ll be missing out on the income if you take time off. After they quit the restaurant business, they finally had time to take a 3 month road trip around the US.

I’m just a part time blogger and even I’m not getting enough sleep these days. I spend most of my days being a stay at home dad to our 3 year old son. He’s very active these days and requires constant attention. It’s been tougher recently because he’s not doing what I want and Mrs. RB40 has to keep reminding me that he’s only 3 years old. It’s easy to get mad at him even when I’m trying hard to be calm.

Hawaii, travel , entrepreneur

Can’t wait!


Anyway, we are heading off to the Big Island and we really need this vacation. We haven’t taken an across-the-ocean vacation since 2009. We have been taking it easy on the vacation front since 2010 when we first learned we were going to be parents. We took a few trips to visit my brothers and other family in California in the last few years, but this will be the first time we’ll fly so long. The flight will take about 5 hours and we’ll see how our guy handles it. Probably not too well…

We love traveling and RB40 Jr. is about the right age to accompany us. We can communicate and he can follow instructions (somewhat).  We don’t have to pack a huge bag and a stroller so that’s nice. This is our first time visiting the Big Island and I’m looking forward to experience a few new things with my family. Oh yeah, my brothers and mom are coming with us too so it’ll be a big family trip with 8 of us.

Here are a few things that I want to do on Hawaii.

  • See Kilauea and Volcano National Park
  • Take a helicopter ride (first time!)
  • See sea turtles
  • Relax on the beach and snorkel
  • Hang out with my family

Hard to take a vacation

Let’s get back to the subject. Even a micro business owner like me finds it hard to step away. Over the last couple of years, I have taken my laptop with me and worked at night when we visited California. It’s really hard to step away these days because the internet is everywhere. I’m still going to take the laptop with me on this trip, but I resolve to avoid working as much as possible. So this week we won’t have many  updates. I might post a few pictures, but that’ll probably be it.

I would like to take a good look at the Big Island and see if it is a feasible retirement location for us. I love Hawaii, but we probably won’t make a move until Jr. is done with high school. The cost of living in Hawaii is pretty high, so I’ll check that out thoroughly. I think the Big Island has more affordable houses, so I’ll probably pop into some real estate agent offices as well. Anyone currently living or lived in Hawaii? What are some disadvantages?

Alright, that’s it for now. Here is a question for you – do you find it difficult to step away from work and take a vacation?

Photo credit: flickr paul bica

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{ 25 comments… add one }

  • Clarisse @ Make Money Your Way April 28, 2014, 3:35 am

    My aunt owned a small restaurant and grocery store since 1995 until now. They rarely take a vacation and their restaurants are always open. Even on holidays and special days they’re still working, they have a few workers, but still they choose to work daily.

  • Despina April 28, 2014, 5:09 am

    Dear Joe,
    I am 62 years old and
    I have been living in Greece for the last 23 years. I stumbled across your blog and have been reading it for about 6 months. I have always tried to practice frugality with meaningful living. I am so glad that there are people out there who value meaningful living and family above making money in a lifeless job which does not build but only erodes both family and interpersonal values. I am happy to see that you have a compatible relationship with your wife and that her needs are acknowledged and tended to. As for your son, one word-PATIENCE. In any case,I will continue to read your interesting blog.

  • Amy K April 28, 2014, 6:06 am

    Videos make traveling with a 3 year old easier. We bought a full season of Curious George and loaded it on the tablet. Now that you can use electronics gate-to-gate on most airlines, it’s a total lifesaver.

  • Stefanie @ The Broke and Beautiful Life April 28, 2014, 6:26 am

    I just got back from two weeks in Europe, and even though I did all my freelance work ahead of time and scheduled a whole bunch of posts on my own site while I was away, I admittedly had trouble stepping away while I was gone. I felt compelled to get on social media and share, respond to comments, etc. I noticed a significant drop in traffic the moment I became less active. Just goes to show that blogging is NOT passive income. It’s VERY active.

  • insourcelife April 28, 2014, 6:28 am

    Every time we take a vacation it’s a huge hit to our family wallet – the trip itself costs money plus I don’t get paid at work. I bill hourly so any time I take off gets expensive quick. That said, I have NO problems taking time off. Travelling is one budget category where I loosen the purse strings. Of course we still try to minimize our travelling expenses and we don’t stay at the Ritz. I don’t mind the double hit via reduced income/higher expenses simply because it helps to keep a good work/life balance. Enjoy your trip and try to unplug!

  • Chattanooga Cheapster April 28, 2014, 6:42 am

    Have fun.

    The internet will be here when you get back.

    Went to the big island in 2006. Couldn’t imagine living there. Felt very isolated, and the food sucked (except for the fruit!!!). Beautiful, though.

  • Financial Samurai April 28, 2014, 6:46 am

    It’s worth relocating! I have a house in Oahu and I think about going back every week. The weather is simply amazing. The only issue is the job market just in case the internet business goes caput. I wouldn’t have the consulting opportunity I do with Personal Capital here in SF if I lived in Honolulu.


  • Pretired Nick April 28, 2014, 7:33 am

    My last vacation I did unplug and didn’t do any work and just kept an eye on email. But if something came up, I’d have to take care of it. So, no, I don’t think you can ever get away completely, but I think the trade-off is fair these days where you can choose a killer location for living/vacation but you have to stay tethered at all times. Better than rushing back from a measly week off and not feeling relaxed.

  • John @ Sprout Wealth April 28, 2014, 7:44 am

    It sounds like a great trip! It’s nice you don’t have to take a bunch of those bigger things as that can really turn into a lot of stuff with the little ones. That said, we always struggle with really taking time off when we go on vacation. We give our clients plenty of notice that we’ll be gone and not reachable but some still struggle with not reaching out to us. I imagine part of it is us training them that we will still respond to things while gone, but others will still contact us even if we don’t respond back….as if a three month warning isn’t enough. 😉

  • IWRN April 28, 2014, 8:17 am

    I used to run my own business and had difficult time to take time off. I had to work almost every day to earn income. It was nice to be a small business owner. But it was difficult to have a vacation.

    It is nice to have a trip to Hawaii. My wife and I visited Maui exactly a year ago. We really love island life – weather, atmosphere, attitude, food, etc. We have been discussing our potential retirement location lately and listed some of the US islands – Hawaii, Guam and Puerto Rico. As everyone knows, the living cost is normally higher in the islands. As long as we remain in US and US territories, we must buy our own health insurance! This is our major concern after we both retire from work. The cost of health insurance won’t be cheap – $800 a month for both of us (we are still healthy though) and will increase every year. Obamacare means nothing for us (middle class) and will actually impact our retirement life. I am not sure how retirees deal with the broken US healthcare if they are not covered with Medicare.

  • ICL April 28, 2014, 9:24 am

    I have always wanted to visit Hawaii and the Big Island – hopefully within the next couple years. Sounds like a great trip! A helicopter ride there would be pretty spectacular!

  • Bobbi April 28, 2014, 9:25 am

    Hi Joe! I’ve been keeping up with your blog for a couple months now. I’m 28 and left my job last year to pursue my photography career. You have a ton of great info on here! Keep up the great writing. Btw I was born in Thailand and I think it’s cool to find an Asian financial blogger. Anyway, I’m going to Kauai next week! My girlfriend was born there and used to live there but moved to Boise 2 years ago so I’ll be there to meet her family. She loves it there and really misses the beach. If you wanted to move to Hawaii, what island would you move to? She worked as a sushi chef there . She said being on the mainland really opened her eyes for things to see and discover and she wouldn’t wanna move back unless she’s ready to retire.

  • Even Steven April 28, 2014, 9:27 am

    I can’t provide much on the getting away from my job, everything I run is part time and have the freedom to stop, but expect no money, so it does not run without me, besides real estate, which is pretty hands off.

    I have no problems vacation from the 9-5, in fact might be one of the easier things for me to do, enjoy Hawaii. Kaui was the best vacation I have ever had in my life, love it.

  • davidmichael April 28, 2014, 9:52 am

    Yes! Being an entrepreneur has its pluses and minuses. Since I was in the Adventure Travel field with a Dream job, it was my task to travel and seek new destinations. Only problem was the office work piled up in my absence and I felt under pressure to get back as soon as possible. However, I thoroughly enjoyed travelling about the world for 20 years despite the stress of company ownership. It wasn’t until I sold it that I had total freedom! On the other hand, there are many times that I miss the luxury of travelling first class as a guest of the airlines and hotels plus the outrageous adventures as part of that lifestyle.

    Today, in the retirement phase of life, I find that it is great fun to work for someone else for a short time (one to four months once a year), to increase our cash flow. Surprisingly, I have never had a problem finding a short term job at places like Amazon.com, the National Park system, Christmas Tree sales, etc. In and out in a short time period with no fuss, overhanging responsibilities, or undue stress.

    This summer I will work as a Campground Host by one of the country’s most beautiful trout streams in Central Oregon. That’s the beauty of having a solid income for life, whether it’s from Dividend Paying stocks, Real Estate rentals, Social Security, from whatever. If the job doesn’t work out, just walk away. Freedom of choice! Gotta love the retirement lifestyle.

  • Bob Digiovanni April 28, 2014, 9:54 am

    I have a condo on the Big Island. My plan is to retire there in a couple of years. For great weather and good prices, check out Waikoloa Village. Basic necessities are available in the village, grocery store, gas, bank, restaurants etc. Home prices are comparable to the west coast. Costco and Target are available in Kona and prices are generally the same as home. Farmers markets are another good way to keep expenses down. Waikoloa village is also close to the best beaches on the island, Hapuna and Mauna Kea Beach Hotel’s beach. By careful shopping, I manage to keep expenses down to west coast levels.

  • Done by Forty April 28, 2014, 2:25 pm

    Have a great time on your vacation, Joe! I highly recommend Broke Da Mouth Grindz and Da Poke Shack over on the Kona side, and Thai Thai over in Volcano (just outside the National Park).

    I can definitely see how being a business owner makes it very difficult to take vacation. I wonder if there’s a clever outsourcing solution that might make it easier to step away. Training would be key, but if you had someone abroad who could just handle communications and then touch base with you once a day for a 30 minute debrief, that might make a vacation possible for not too much cost.

  • Justin @ Root of Good April 28, 2014, 3:11 pm

    I started my blog right after I retired. I treated it a bit too much like work and spent too much time on it initially (when I didn’t really need the money). I’ve found a happy medium now. I write when I want and don’t feel bad about it when I drop the writing for a couple of weeks. I get busy, life gets in the way.

    If I was dependent on the blog for income, I’d have a lot harder time stepping away from the keyboard.

  • Lamar Buys Houses April 28, 2014, 5:48 pm

    I love what I do for a living and in the past I rarely took vacation. As of 2014 I’ve decided to take 3-4 day weekends and travel. This way I feed my passion for my business but take time to recharge and decrease burn out.

  • C. the Romanian April 28, 2014, 11:35 pm

    Indeed, it’s very difficult to take time off when you’re on your own. Many of my friends envy me for being self employed, but they don’t realize that if I stop working, I’m not making money. However, vacations are a must in my opinion – or at least some time out, because otherwise you will eventually burn out and not be able to do anything. I too take “working vacation” as I still have to check things and approve stuff, but usually I try to keep it under 2 hours per day with weekends completely free when I’m on vacation. Not the ideal situation, but it has to be done.

    Have fun in Hawaii and post A LOT of photos!

  • Little House April 29, 2014, 7:07 am

    Enjoy your vacation! I love Hawaii, but have never visited the Big Island. I hear it’s beautiful. I hear you with taking time off. For years, Mr. LH and I worked weekends, rarely taking a day to ourselves. A few years ago, we decided to start taking short trips and would tell customers that we’d get back to them in a few days. Thankfully, we didn’t lose any clients that way and now take a couple of short trips throughout the year. It was difficult at first, but became easier the more we just let go.

  • Money Beagle April 29, 2014, 7:41 am

    It’s hard to take time off as an entrepreneur for the simple reason that nobody cares about your business and will tend to it as well as you would. That being said, if you have people you trust and you manage your time away effectively (leaving as little to chance as you can), it can be done.

  • Martin April 29, 2014, 10:40 am

    It’s very tough, but needs to be done! You have to just turn everything off and get away. Don’t think about anything on your trip. You’ll always return more refreshed than ever. Your business can wait.

  • Jackie August 18, 2014, 7:22 pm

    Wish I had discovered your blog a few months sooner! I live In Kailua kona (born and raised) am self employed and have decided that my goal is to be retired by 45! Its a little tricky with the high cost of living, but I am determined and learning a ton right now. Great blog!

    • retirebyforty August 20, 2014, 9:39 am

      Good luck with your retirement journey! I love Kailua. We just went to visit earlier this year. I’d love to retire there. We’ll see how it goes in the next 20 years. 🙂

  • Jesse Gernigin May 27, 2015, 11:08 am

    I’ve always felt that having the freedom to come and go as you please is a great thing. As an entrepreneur I never feel like i’m working. I do however feel a duty to my customers. My mentor always told me ‘You’ll know success when you worry about giving your best service and less about where your next payment will come from’.
    I do a lot of writing and coaching but I spend a lot of time climbing and hiking. I know you have posts previously about having problems sticking with hobbies but my hobbies help me define when and what kind of freedom I like and am working for. I don’t know if i’ll ever completely retire but I do feel that knowing what you want for free time makes it easier to take time off.


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