5 Things I’ve Learned During My 20 Year Work from Home Experiment

“How do you do it?” I get that question quite a bit, but I recently got it again from my neighbor since he and his family are housebound with the current lockdown status that many of us are dealing with. How do you work from home full-time and how have you been successful at it for almost 20 years? After working in our San Francisco office for a few years in the early 2000s, I summoned up the courage to ask my boss if he’d be open to allowing me to work from home in Los Angeles.

At that time, there weren’t a lot of people working full-time from home. However, being in a sales role, my boss was comfortable with running an “experiment” of me working from home. What that experiment meant was I either hit my numbers or I didn’t. And I knew what would happen if I didn’t. Given that I wanted to keep my job and be able to work from home, I was extremely motivated to prove I could be as productive as working in the office, if not more so. Here’s how I did it:

1. First and foremost, I treated my job no differently than when I was working in the office. It was of the utmost importance that I made this work. My boss took a chance on me and he valued my contributions to the team, so I did everything I could to make sure I was successful out of the gate. I made sure that I woke up at the same time as before, showered, got dressed, ate breakfast, grabbed my coffee, and was at my desk by 7:30 in the morning.
2. I spoke with my boss often. Video conferencing was in its infancy at the time, so we didn’t do much of it in the mid-2000s. However, my boss and I would be sure to meet every week to discuss what I was working on, what hurdles I was encountering, and how I could improve my skills even though I was 500 miles away. Today, my boss and I have at least one video conference a week.
3. I was vocal and I managed up. If there were friction points, I made my voice be heard. It wasn’t always easy, but it was important to let my team know if I wasn’t able to use certain software because the VPN wasn’t connecting or my phone system wasn’t working. The benefit to the company was that I was beta testing what it would be like to have a remote workforce and, 15 years later, over 25% of our employees work remotely.
4. I visited the home office. Yes, I was hitting my numbers consistently, so the “experiment” was working out as I had hoped and expected it would. However, being remote meant we had new employees who had no idea who I was. And I wasn’t continuing to build relationships with the people I had worked with when I was in the office. This was a very real concern for me. Would my co-workers wonder what I am doing? Would they be resentful of the fact that I was able to work from home? The solution was simple: I visited the home office once every three months for several days. This allowed me to build great relationships with my co-workers, some of whom I never worked with in the office. Some of these co-workers are people I now consider lifelong friends, even though I don’t see them day in and day out.
5. I set up a home office. Not an area in my living room or bedroom, but in a separate room where the sole purpose was to be a quiet place to do work. I am on the phone or in virtual meetings most of the day, so it was critical to have my own space where there was no background noise and I could concentrate. Not everyone is able to do this, but if you can, I highly recommend it. I know that when I walk into that room, it’s time to get work done. It also means I can get away from work when I need to by leaving my office.

Are there downsides to working from home? You bet there are. There are times I feel forgotten or not part of the team. I’m not able to go to happy hour and I don’t feel as plugged into the inner workings of the company because I’m not there every day. However, there are so many benefits to working from home, and I’m not talking about working in your pajamas.

The first thing I noticed right away when I started working from home was how much work I could get done in a standard workday. I would estimate that I was about 125–150% more efficient working at home. If you add up all the time spent getting caught up in a conversation at the water cooler or being pulled into a meeting you might not really need to attend, it’s significant. I can also put my head down and make calls for an extended period of time without being interrupted. For the most part, I get to decide which are the most important items that will make me successful in my job.

After a couple of years of living in Los Angeles and proving that the experiment was working, I was ready to take an even larger leap. Before I began working at ClickTime, I lived in the mountains in Colorado and, after being away for a few years, I was really missing it. I wasn’t happy living in San Francisco or Los Angeles (no offense if you live in SF or LA). It just wasn’t for me. Colorado was where I was happiest. I knew that moving several states over and to a more remote location would be a bit of a concern for my boss, so I actually created a presentation on how it would benefit the company! I got up the courage again, opened up my PowerPoint deck, and my boss said, “Is this where you ask me if you can move to Colorado?” He knew what was coming, and after discussing what it meant for everyone on the team, he was open to it. Yes, I was very fortunate I had a boss who understood that keeping good employees is so important that sometimes you need to make concessions.

One of the biggest benefits of working from home is that it doesn’t put limits on where you can live. I had a job I loved, I had invested years of learning how to do my job better, and I had relationships with co-workers that I didn’t want to lose. And now I was getting the best of both worlds. After I was done working for the day, I was able to hop on my bike and go for a ride, or just go for a quick hike. It was fantastic.

Fast forward a few years, and I’m married with one son, then a few years later, another. When my boys were young, I was able to have lunch with them every day. For a family man like myself, you can’t put a price tag on that. Those years were some of the best of my life, and I will be forever grateful that I worked for a company that facilitated that.

There are other benefits, like being able to squeeze in a quick home workout, the fact that my commute is two flights of stairs, and being able to save a ton of money by not eating out five days a week. The time savings and the freedom that working from home provides means that I won’t ever work in a traditional office again.

If this is your first time working from home, give it some time. Try to get into a routine, and give yourself breaks throughout the day. Get up and go for a short walk, otherwise, you’ll stay chained at your desk for eight hours without even realizing it. Enjoy the time with your family if you have one. You might have to go back to an office at some point. Or maybe after this experiment, you can convince your boss to let you work from home too.