I haven’t worked in non-home office in over two years. As most telecommuters will agree, the situation is a mixed bag. With working on my project, I’m a 9 hour drive away from our main office building. Learning to work remotely by yourself is a challenge. Learning to manage employees is a endeavor that is impossible to appreciate until you’ve done it. Not tooting my own horn, just reflecting on the task it has been.

What I’ve learned about working remotely:

• Have your own dedicated office space. Working from the couch in your living room where the kids play just isn’t productive. Thankfully I’m not a couch-working type of guy.
• Try to dress the part. While working remotely is stereotyped as working in your boxers, I wouldn’t advise it. When you dress lazy, you tend to work the same way.
• Get a good webcam and decent internet connection. You’ll want to video conference at least once a day to stay in the loop.
• If your main office doesn’t proactively try to support you working remotely, you’ll be the most miserable person in the group. I cannot emphasis this enough. Finding out about new hires, big features and news releases the day of isn’t enjoyable.

One of the reasons I haven’t posted on here in a while has simply been because I’m swamped with everything else in life. The last few years have been some of the most exciting, stressful, and obnoxiously busy years of my life.

Three years ago a friend of mine approached me with a simple question: would I want to help him solve his $55k/year problem? He was paying interchange fees that he’d rather keep, rightfully so. So we spent a few months going over what the ideal solution would be whenever we chatted.

Once we knew the general direction we were going, Ben took charge over the business, legal and PR side, and I was tasked with making a system capable of moving millions, or billions, of dollars in my spare time. At this point in my life, I had a one year old son, was paying wayyyy too much money on a rental house, worked at a job that didn’t pay enough to make ends meet, and had student loan repayments kicking in. Not the most opportune time for a project of this magnitude, but it was a challenge I wanted to take head on.

For the next two years, I would work 8-10 hours at my normal day job and go home. I’d sit down for a quick dinner, and then head downstairs where I’d spend the next 6-8 hours cramming away on this Dwolla project. Somehow I managed to never pass out at my day job (I actually did a pretty good job there as well. Though, looking back, I had lots to learn…) and my wife never divorced me. I wouldn’t have blamed her if she did.

While right in the midst of all of this, I bought a house that had pipes burst two days before closing. We spent the next 6-9 months in a construction zone, where I moved my makeshift office around to wherever was the least dusty.

As far as Dwolla goes, the first year I pretty much spent in proof-of-concept mode. I scrapped several different components along the way and rewrote them after finding a better way to do it. Financial service products were new to me, and I definitely had lots to learn.

One of our more interesting days was when we first moved money from A to B through the network I made. Ben’s response?

Another one was when I first set up sending money to Facebook and Twitter contacts. It was one of those ‘doh’ moments. I recall the first meetup I was able to attend in person, which was when we announced this feature. I sat in the corner of Mars Cafe glued to my laptop monitoring performance of the contact sync service. We ran into some issues earlier that day, so I was terribly nervous that the fixes I had put in place earlier in the day weren’t going to cut it. Thankfully all worked well and I was able to enjoy the rest of the night. It would have been nice to be able to announce the feature myself, but someone had to make sure things didn’t break

I’ve passed the three year mark this summer, which I’ll write about in another post. Hopefully less scatterbrained than this one.