In this series I interview people who were able to transition their office job to a remote work position. In the first article, I introduce Veronica, who turned her dream of full-time travel into reality. You can read that story here.

In this article, you will meet Craig, husband and dad to four kids…and a dog. I met Craig through his wife Bryanna, at the RV Entrepreneur Summit.

Bryanna and I hit it off at the Summit and ever since, collaborating on many projects. In addition to their family travel blog, Crazy Family Adventure, she runs Virtual Power House, a virtual business solutions company, specializing in social media strategy and web design. When I learned that Craig devised a plan to take his job remote, I had to know more. So here’s Craig.

1. Tell us a little about yourself, your background, what you do for fun, work, etc.

My name is Craig Royal and I am currently RV’ing North America with my family which includes my wife, Bryanna, four kids and our dog Indy. We’ve been on the road for over three years and are really enjoying it!

Before hitting the road, we lived in a beautiful 2500 sq ft house that Bryanna and I designed and had built. It was a total family house that we planned to live in our entire lives. After about four years of living in the house and dealing with all that comes with home ownership, a career, and a young family, we realized we didn’t have time to enjoy our lives and young kids. We were either maintaining the house (even though it was new), working or running between activities with the kids.

It was then that we started looking into full time RV’ing and found many families who were RVing full time and loving it! We also saw that it was possible to earn money in a remote work position.

If you want to learn more about our family and adventures, check out our Crazy Family Adventure here. https://www.crazyfamilyadventure.com/start-here.

2. How did you get into your current line of work?

I was a Computer Science major in college and got a really great internship my junior and senior year. That internship turned into a full-time position once I graduated and I excelled in the workplace. I’ve always liked computers and enjoy coding, so it was a good combination of career and passion.

I have been in I/T for about 15 years. This has ranged from applications development to database administration to management. Most recently I worked at a small university in southeastern Wisconsin where I was able to transition my job to a emote work position.

3. What made you decide to travel full-time?

Bryanna and I saw our kids growing up so fast. We really wanted to be present in their lives and enjoy life with them rather than going from activity to activity–everything becomes a blur. We also wanted to see new places and experience new cultures with them, as well as share the amazing places that we have already been with them.

4. Were you worried about keeping your employment? What worried you the most?

I was definitely worried about keeping my employment once we decided to hit the road. We relied on my salary as our main income source and weren’t prepared to lose it. However, it was so important to Bryanna and me to make this lifestyle a reality that I put aside my fears and went for it.

5. How did you approach your employer about a remote work position?

Unfortunately for me, the university I worked at didn’t have a telecommuting policy and no one really did it. Everyone came to the office every single day. Fortunately though, my boss was previously a consultant who did remote work in his prior positions, so he knew it could be done effectively.

Before approaching my boss with the idea of remote work, I put together a solid plan of how I would be able to still accomplish all that I do everyday without being in the office. I was a manager of five employees, so the biggest challenge was making sure my team was productive without me being there.

The second biggest challenge was how I was going to attend meetings. Being at a place that wasn’t conducive to remote work, meeting rooms didn’t have the equipment to run a remote meeting.

I put a plan together of how I could manage my employees and still attend meetings without impacting others. I planned to have weekly Skype calls with my employees for project updates, and I made sure I kept in contact with them every day of the week, whether through email or phone.

I also checked on equipment for me to attend meetings and was able to make that work as well.
After doing all the groundwork, I approached my boss with this plan and he was definitely open to it! One reason that he was open was because he didn’t want to lose me as an employee. He knew there were plenty of remote work opportunities that I could pursue but he wanted to keep me on his team.

I knew that one meeting wouldn’t be enough to address all of his questions and concerns. So we worked through it together over time and created a plan.

6. What did you say and what concerns did they have?

My boss’s main concern was how this would affect other employees in the department and across the university. I didn’t have any student interaction, which is our main customer at a university, and I already had an answer for how I’d handle my employees as well as meetings.

My boss was also concerned with how his superiors (Chancellor and Vice Chancellors) would react to this news. Since I worked with most of those people already I decided to meet with them individually and explain what, why, and how this would work.

As compassionate human beings with families of their own, they understood my reasons.

7. How did you overcome any concerns?

After getting the proper approvals from my boss and his bosses, we set up a test run which was working remotely for three weeks a month and being in the office for one week. This wasn’t ideal as we couldn’t go too far, but it was a start.

The first month went great and there wasn’t any change in my performance or my team’s. This gave my boss some confidence that it could work. After doing the test run for a few months, I asked if we could extend the remote time. We agreed upon being remote for about seven-eight weeks then back for a week. This was much better and allowed for us to venture a bit further from Wisconsin.

8. How do you like traveling and working from the road?

Working from the road is fantastic, although there are some challenges. I was able to work right from our kitchen booth in the RV or from our picnic table outside, or even from a lawn chair on the beach. As long as I had internet, everything was great.

When I didn’t have internet, however, it was a problem. Our travel plans now include checking Verizon coverage and when that isn’t available, finding a backup internet plan. For the most part, the US has great coverage, but the places we really like visiting (like National Parks) usually have very limited cell coverage. We have always been able to find a backup solution, whether that be sitting in the lodge at Yellowstone paying for their internet or driving to a Starbucks.

The traveling part has been great, but it’s not all sunshine and rainbows as Bryanna likes to say. There are some definite challenges being with your family 24×7. There are also a few things that we didn’t really expect when we first hit the road, but quickly found them out. Here’s an article on a few of those things https://www.crazyfamilyadventure.com/10-things-about-living-in-a-rv-full-time/.

9. What advice would you give others about talking to their employer about setting up a remote work situation?

I recommend putting together a solid plan that addresses all concerns that you can foresee. Then find someone who is great at playing devil’s advocate and see where they can poke holes in your plan and address those. Also talk to people at your company or other friends that you know that have done something similar, and find out how they approached their employer.

It’s important that you show that you are taking a remote work opportunity very seriously and professionally.

10. Anything else you’d like to share?

As with any career or job that you value, make yourself indispensable. If your employer can’t afford to lose you, they will do anything they can to keep you happy and employed with them. This was a critical for me getting the approval I needed and was even told this by a Vice Chancellor.

If you are critical to their success, they’ll want you even if you aren’t physically there.

Also, always have a backup plan. Your employer may decide that remote work isn’t working and require you to be back in the office. Our plan B was to have Bryanna start a virtual business that we would eventually use as our full time income. Here’s how she did it and since then has really grown it into a successful business https://www.crazyfamilyadventure.com/how-i-started-my-online-business/.

Thanks Craig! I love a good plan and wow, you are my new hero for planning!

You can follow Craig and Bryanna, and their Crazy Family Adventure at https://www.crazyfamilyadventure.com.

Next up: See how Robert and Jessica from Exploring The Local Life have structured their remote work arrangement.

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