What I’ve Learned While Working Remotely


We are just wrapping up our month long visit to the Big Island of Hawaii. I say visit and not vacation because the first two weeks here I worked a regular work day. I extended our trip because I wanted to experiment with working remotely, and I wanted our family to be here as long as possible. Here are some of the things I’ve learned

First, before I start, not every remote work situation is going to be the same. I was primarily running our appliance business remotely. That involves making sure there was enough work to keep everyone busy, finding appliances to buy, posting appliances for sale, handling all the sales calls and scheduling deliveries etc. This required constant access to my phone, a high speed internet connection and the work to be done during regular business hours.

1. You have to be very disciplined. I would get up at 6 am here every morning and start my day. We are two hours behind the west coast out here in Hawaii. I would work until things slowed down later in the afternoon. Normally this isn’t difficult to do, but it’s much more difficult when you are in a tropical location and you have the clear, warm, beautiful ocean tempting you to come swim.  Later in the year after the next time change I would have to start at 5 am.

2. Cell coverage and internet access are necessities. This might sound obvious, but there are many places, especially on the island we are visiting, that don’t have good cell phone coverage. You have to plan ahead and make sure you arrange to stay in a place with adequate coverage. The same goes for high speed internet. We are staying in a friend’s condo that has very fast cable internet. I came prepared with my 4g hotspot just in case because fast internet access is a must. No coverage = no work. Do your research before you go.

3. Prepare for some extra guilt.
We flew out of Portland and as if on cue the sky dumped 8 inches of snow/ice over the city. It’s one thing for the people in your business to be aware that you are in a warm tropical place, but quite another when they are experiencing extreme cold and snow. Warranted or not, this brought on some extra guilt. Instead of being able to go outside and empathize with their situation, I found myself drinking a cold beverage with my shirt off well into the afternoon.

4. Communication is key. You have to be able to communicate well with your team via phone, texts and emails. If you can’t, it will drive you crazy because there is no walking down the hall or going out into the garage and making sure things get taken care of. If you have communication issues before working remotely, they will only be magnified when working from afar.

5. You have to be able to trust your team. If you can’t completely trust those that you are working with, things aren’t going work out. If you want to be able to work remotely at some point, you have to be able to find great people to join your team. It’s one thing to feel like you can trust someone when you are always around, but quite another when you aren’t going to be present to keep an eye on things.

6. Problems get magnified. When there are problems, or business is slow, you will feel the effects more when you are working remotely. I think it mostly comes from feeling like you can’t do as much to help when you are not physically there. Being physically present to handle a problem or crisis definitely has it’s advantages. So know that there will be extra stress when problems arise. .

7. Funny story. I got a call from a guy who wanted us to deliver his daughter a dryer. At the end of the conversation he kind of laughed and said that he was actually calling from Oahu! I laughed as well when I told him that I was just a little south of him on another island in the middle of the pacific ocean. We both got a kick out of that and set up the delivery. It’s a new world we live in!

8. It’s a great way to escape for a season.
Portland is a great city, but there are often periods during the winter where you don’t see the sun for quite a while. It can be dark, rainy and cold for weeks on end. This is a major cause for seasonal depression, and it’s something I’ve struggled with often during the winters. I planned our trip out here to escape that weather at it’s worst, and it was a bonus that tickets out here are cheapest in the winter months. Hawaii is an outstanding antidepressant.

The other night I was out in our surf spot with some friends, waiting for the next set of waves to arrive. We were laughing, joking and just having a great time together, all while getting some refreshing exercise. The water was warm as was the evening air. We stayed out surfing almost two hours. Then we came in and joined a bunch of other friends for a BBQ and to hang out until well after dark. This happens every week.

It’s been this combination of beautiful community, location and general lifestyle that has motivated our family to actively pursue the the possibility of working remotely, even if just for a portion of each year at first. For others it might be to live closer to family, to save money by living somewhere more affordable (think anywhere outside of silicon valley) or to enable a season of extended travelling. Everyone is different, and no two paths are going be exactly the same.

In the end, technology is making it easier for people to add value remotely. Though working remotely isn’t for everyone, if it encourages and enables people to focus on living a healthy, happy, balanced life, it is a beautiful thing. Remember, we don’t live to work, but we work so we can live.

Have a remote-work story you would like to share? Or a situation where you wish you could have lived somewhere else and worked remotely? What would like to be able to work from?

Bonus: I took this video yesterday of a humpback whale slapping it’s tail 19 times in a row. Pretty amazing to watch!

This second video is the road down to our surf spot that I describe in the post.


  1. Thanks for the inspiration. 🙂

    I work mostly from home but rely on an employer for my main source of income and supplement that with my indie ventures.

    This summer I’m thinking about seeing if I can fund some traveling by sourcing for stuff to sell during the trips. It might be a fun challenge to write about: can I cover the costs of gas, lodging, etc with stuff I find on the trip? We’ll see if I follow up on this idea. I think my partner would be totally into it.

    • I’ve thought about doing that myself, travelling from city to city only using the money I was able to make locally in each city. Keep me posted if you do it!

  2. Hey Ryan,
    I was wondering with you being able to do what you do on Craigslist pretty much anywhere, why do you stay in a colder climate? I know you want to eventually move to Hawaii but you could probably do just as well in other cities in the mainland with warmer climates.

    • Primarily family at this point. All of our family is in the NW, but it is something we are thinking about more and more. Hawaii would definitely be the place we would move to when the time comes. We have a lot of close friends out there. We’ll see!

  3. Your kids must be ecstatic about such a great adventure!! I’m guessing you must be a homeschooling family to be able to take a month long visit in the middle of the regular school year. We homeschool and love the freedom it brings! Thanks for all the great information on this blog!

    • Thanks Jen! Yeah, the kids loved it! We are homeschooling, and though they were ahead of schedule before leaving, they still did schoolwork while we were there. Homeschooling has a lot of side benefits, and being able to take advantage of the off-peak travel season is definitely one of them! We saved almost 2k just on our airfare alone being able to travel in the winter instead of the summer!

  4. Hi Ryan, I am enjoying your website. I stumbled onto it while researching whether it would be worthwhile for me to scrap a non working 2nd refrigerator myself, (it wasn’t) rather than have it picked up by the city. I’ve sold some scrap when I’ve accumulated enough from projects to make it worthwhile and I’ve sold stuff on Craigslist here and there. I’m intrigued that you built an appliance business out of what started out as scrapping.

    You mentioned having a “team” in your blog about working remotely. I was under the impression you ran the business by yourself? Do you have an employee(s)? Wouldn’t being absent and leaving it for them to run, (picking up, delivering, buying, selling, etc.) get them to thinking, why should they work for someone else, when they could do it for themselves? After all the barriers to entry aren’t that great, provided they have the knowledge.

    Anyway, I’d like to thank you for the value you provide for free on your site and wish you lots of success. I’d also like to compliment you and your wife for the great job you’re doing with your children. Much respect!

    • I started out running the business by myself, and then took on a partner for a while, then move to working with my brother, and now I’m back to working by myself again. Different seasons in each of our lives and this is just where I am at right now.

      As far as worrying about them running off with the business if I am gone, it’s a possibility I guess. One of the most important things is hiring/working with people you really trust, and that have the opposite skills as yourself. This makes it much less likely that they will run off and try to do things on their own as the “technician” is rarely also the salesman, business development person etc. Most people can’t wear all the hats, or aren’t willing to take the risks of attempting to. Plus, it’s not as easy to do everything as it might seem. It takes a lot of work and time to learn all the different aspects of any business.


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