About 18 months ago I packed my family up and moved across the country from Chicago to San Francisco when a new opportunity popped up for work. Born and raised in the Windy City, my wife and I figured that we only had one life to live and we didn’t want to have any regrets when we were old, so off we went. I had been running Capacitr, my marketing agency, for a few years at this point and I always had some sort of loft office in downtown Chicago that I could escape to during the daytime hours to hustle and get work done. I knew that moving west was going to drastically affect my daily workflow. I figured why not, we only get one life to live. Besides, there is literally an endless stream of new companies popping up in the Bay Area that would be able to benefit from the work we do, so I looked at it also as a new way to build the business.
I love putting myself in new and challenging situations and looked at it as a way to get more experience in life and further develop my own skillset, so we took our 8-month-old son and headed out west. A buddy and I drove out with my two dogs and chronicled the entire trip with a GoPro. I edited the hours of footage into a two-minute video, which you can see below.
We made the trip in two days, leaving my two-story place in Chicago for a two-bedroom apartment with my wife, kid, and two dogs. The adventure was about to begin. While the system I’ve got in place now is certainly not perfect, it allows me to get a solid 10+ hours of work time in during the day but does require some pretty crazy discipline.
My Daily Routine
My days all pretty much follow the same general structure because I feel it is important to have some sort of consistency in my schedule in order to get things done and actually be effective with my time. I usually am woken up between 6–7 am by my son, my twins crying in the other room, or my wife waking up and corralling all the little ones so I can get that extra 30 minutes of sleep. Periodically I will just hop out of bed at this time and go for a run to break through the brain fog and to get my mental juices a’flowin.
After getting up and out of bed, I head into the kitchen and am greeted by my son and wife who are eating breakfast. I grab a cup of coffee, make some oatmeal, or eat a banana, and sit down with my family until around 8 am. At that point, I go and get dressed. Some people who work from home can sit all day in sweatpants and be fine. I feel like a lazy sack if I am on the phone with my clients while wandering around in my pajamas. I head into my office right after that with a fresh cup of coffee.
I don’t like to check email until I sit at my desk. I feel that it generally has an adverse effect on my day if I do so before I am mentally prepared to respond to whatever is within Pandora’s box. If it’s a Monday or Friday, I get on a video chat with my team promptly at 9 am to run through our weekly goals and lists or debrief each other about the past week. If it’s any other day of the week, I usually have client calls at 9 am. I’ll dial into those a few minutes early and listen to the lovely conference call hold music.
After that, and depending on what is on my schedule for a given day, I will either wait until rush hour is over to head into San Francisco to visit clients or I start trying to cross things off my task list.
I generally work straight through lunch and don’t stop until around 2 pm, which is when I start to get hungry. If I don’t take a trip to the city, this is the first time during the day I’ll head out of my closed up office. I’ll greet my dogs, see what my wife and kids are doing, and eat some lunch. I usually end up bringing my lunch back into my office and closing the door. Lunch is really the only time of the day that I’ll hunt around on news websites to bring myself up to speed with what is going on in the world outside of my house. After lunch, I like to let my dogs outside, wander around my deck for a little bit to get some fresh air, and then get back into it.
The most disruptive time of my day while working at home is around 4:30 pm when my dogs start to get antsy that they are eating soon and my kids come and start banging on the door because they know I’m in there and it’s almost dinner time. Dinner generally is early, somewhere between 5–5:30 because the kids have to go to sleep at a reasonable hour. Between 5:30 and about 8 pm is usually family time.
After everyone is sleeping, Ill sit at the table with my wife for a bit talking about life and being impressed that she can handle the family on a daily basis on her own while I am busy hustling in my cave. Around 11 she heads into the bedroom to catch some Z’s and I head back into my office and generally will get in another hour of work, catch up with friends, or read. I prefer to read fiction and listen to non-fiction books on tape. I know many entrepreneurs stay away from fiction but I feel they help me continuously expand my mind and further develop my creative process. I can not fall asleep unless I sit and read a book for about 30 minutes before and let my mind shut down from the day. I wake up again the next morning and do it all over again. This has been my life for the past 18 months.
How I Stay Organized
There are so many SaaS apps now that can run your entire life and working from home and while staying organized is a tough thing, I still rely mainly on my Field Notes Steno Pad and a pencil. Specifically a Rotring mechanical pencil or a Palomino Blackwing. I hate pens.
To me, a pencil embodies the life of an entrepreneur because it’s messy, unrefined, and raw.
I sketch out designs and wireframes a lot and like to reorganize things on my list regularly so I like having the eraser. I also use sticky notes all over my walls and on my computer monitors for brainstorming, user flows, or important reminders that I can’t trust Alexa for. We use Google Apps, Slack, and Notion pretty effectively and it allows us to communicate with each other and stay on top of everything that pops up on a given day.
There are a few physical gadgets that I could not live without. Top of that list is my Plantronics Voyager UC headset that is connected to both my computer and my cellphone. I despise holding phones and this is a very comfortable and flexible headset that can easily run through an entire day without needing to be recharged. [2020 update: Replaced by Airpod Pro headphones] My walls are not soundproofed, so I do hear yelling, barking and crying regularly and I can easily block all of that out with my trusty Beyerdynamic dt770 headphones. These are amazing, have an incredibly long cable and despite the fact that they are not “noise cancelling” successfully block any and all distracting noise from entering my mind.
I’ve got a custom-built PC and a wired keyboard and mouse because i don’t like having to deal with interference, dead batteries, and I come from the land of PC gaming even though I have zero time to play anything these days. When I am on the go, I’ve got my trusty rMBP 15” as an effective sidekick that can handle just about anything I throw at it.
My wife is the unsung hero of my business. Without her, I would not be able to get anything done while working from home because I would be too busy playing with toys or changing diapers. When you hear someone say that behind almost every entrepreneur is a supportive wife, I know first hand, there is not a more truthful statement to be made. She successfully navigates my toddler and boy/girl twins like Luke piloting his X-Wing through the Deathstar as if she uses the force to control the 3 kids and 2 dogs. I cannot say enough good things or communicate how fortunate I am to have this dynamic, it makes it possible for me to work from home and actually get shit done.
I am pretty much an all or nothing type person, I either do something 110% or I don’t do it at all, I don’t really have time for half-assing things and I knew I was going to have to learn to tune things out or I was going to be screwed. For that reason, I’ve got some pretty specific habits that allow me to ensure I get the most effective work done that I can while I’ve got a million things going on around me. I don’t have a television in my office nor do I have any stimulating “device” that will take my attention away from my work. I personally do not buy the idea that people can just “have the tv on in the background” — your brain can only accept so many stimuli at once. The key here is minimizing those inputs so you can focus. Besides, daytime television is garbage and I’m not into sports
I happen to be by far the most productive in the morning with my attention/effectiveness fading pretty strongly throughout the day. For that reason, I will generally schedule phone calls in the afternoon and try to get work done in the morning. Outside of the internal video calls and the regular 9am check in calls with clients I pretty much have my headphones on and am incredibly focused on moving through my task list. I have a daily goal of crossing 2 things off my check list per day. I can often complete way more but as long as I can knock off 2 things, I consider it a useful morning. The door to my office is also quite heavy and my son isn’t really able to open it yet so i don’t generally have to worry about him trying to come in. If you’ve got a door that is easily opened, I’d suggest getting something that makes it more difficult. Just so that anyone looking to come in and disturb you has to go through 1 additional step to do so. I also keep mixed nuts, dried apricots and a filled Nalgene bottle in my office so that I don’t have to disrupt my flow by walking out into the kitchen for a quick bite or a drink if I am in need.
Find What Works For You
While everything I have listed here works for me, it might not be what is most effective for you. Some of our team likes to get out of the house and go to the coffee shop or library to work. I avoid that for the same reason I avoid extraneous stimuli during work, it’s just more new information in a new location for your brain to process. I find shutting everything out and forcing blinders on myself to be the most effective way to get real work done.
I also realize that some of you might not be able to shut yourself in an office with a heavy door or have a wife who stays at home and is able to manage the kids and four-legged critters on her own — so your mileage may vary here.
All that really matters is that you’ve got the discipline to be able to wake up every day and put forth the same (or more) effort into your day than you did the day before.