No office, no boss, no boundaries: The Life of a Bootstrapper

I loved this CNN article that I found courtesy of Hacker News, except for the sketchy spin on loneliness.  It captures some of the lifestyle I’d like to have, though I’m not there yet.  I have been able to quit my day job, but I’m still low enough in six figures and busy enough with the business that living continuously on the road is somewhere, um, down the road.  To give an idea, here is what my day looks like, give or take a half hour on the timings:

6am to 7am:  Wakes up, triages email, RSS Blog Feeds, and News on iPad from bed.  Decadent, I know, and a disgusting habit, but I’ve grown to like it enough I will admit to it.  I use my iPad for information consumption and triage.  I hate typing on it (methinks the Microsoft Unicorn er Surface will fix that), so at most I read the email in Gmail and either star it for futher attention on a real PC or archive it.  This is a common workflow for me and I also use it for my RSS Blog Feeds.  I subscribe to about 200 blogs at the moment, so being able to rapidly triage is critical!

7:30am:  Sit down in front of PC to do CNCCookbook Customer Service.  Order fulfillment, question answering, and site metrics monitoring all fall in this category.  Between Customers, Beta Testers, Trial Users, and other miscellaneous contacts, I am dealing with a population of about 6,000 that want a piece of my time in some way.  My tools for this time include GMail, User Voice (my Customer Portal software), a PHP BBS clone (our User Forums which I call the Customer Club), Google Analytics, and Mailchimp if I need to check status on some mail campaign.  For example, every Wednesday morning we do a big mailing of our blog digest and I like to check which articles are getting the most traction.

8:30 – 9am:  Depending on how much is going on, I am ready to progress from customer service to writing software.  It’s important that I shut down the web browser and bring up my Agile Backlog (that lives in Excel because it is just so easy and I don’t have to coordinate with a team) and Adobe Flashbuilder.  Time for heads down software development.  I take a break after every 2 or 3 Agile Backlog items are retired or every 2 hours to hour and a half, whichever comes last.  I find the breaks refresh my ability to concentrate and help stave off a stiff back and neck.  Ideally a break will consist of a walk on at my new treadmill desk and a bit of Web Grazing (it’s more leisurely than Web Surfing) on my iPad.  Of course, I will take the opportunity to do a quick Customer Service check-in on the walk and deal with any issues when I get back to my PC.  If the weather is nice, I’ll take a short walk outside.  You can see Monterrey Bay from my house.  Breaks are 10-15 minutes and I think they correspond to time in an office spent at the water cooler, restroom, or chatting with coworkers.

11:30 – Noon:  Go to lunch.  Unless I am really in a crunch mode, I want to leave the house for lunch.  I have lunch with my wife MWF and with a co-worker, friend, or other contact on Tuesdays and Thursdays.

1 – 1:30pm:  Back to work.  I do a quick Customer Service check then I am back on the coding with breaks cycle.

3:30pm:  Go offsite for coffee.  I am a total coffeeholic.  My ideal office-style work environment will be within walking distance of at least one Starbucks-or-better quality coffee establishment.  I will then proceed to take people on walking meetings for coffee, one in the morning, one in the afternoon, instead of looking them in a conference room.  Works great.  Unfortunately, I can’t really justify more than one coffee outing a day in my new Bootstrapper’s Lifestyle.  I don’t have anyone to meet with really.  Nevertheless, there are quality of life issues, and it is important to step back from the individual tree I am banging head against at the moment to review the status of the forest.

4:45pm’ish:  Back to work.

6pm:  Dinner with Family.

7pm:  Back to work.  If I am really up against a deadline (all self-imposed, but they really always are), I will keep coding.  Otherwise, this is when I do my marketing work.  The vast majority of marketing at this stage consists of writing content.  I averaged 5 blog posts a week in 2012.  To do this work, I keep a big Delicious bookmark list of things that might turn into articles.  Or they might not.  If I can’t face writing at 7pm, I will allow myself up to 1 hour to go Surf the web to research article ideas.  The rule is I have to stick to content that is relevant to my audience.  Content creation happens about 5 nights out of the week.  The other two involve setting up A/B tests, working on web design, web analytics, and grooming my Agile Backlog for Marketing.  Everything except the Editorial calendar is managed from my Agile Backlog, including all marketing.  The Editorial Calendar works better by immersing myself in ideas and seeing what ignites the Muse.  Something always does.  Ideas either come from Surfing the Web, looking at my Delicious Bookmarks, or through Keyword and other Analytics Analysis.

9-10pm:  Knock off.

I don’t watch TV except for Kindle Fire episodes after 10pm.  When I went to Windows 7 64-bit, my last first person shooter computer game quit working.  I have studiously avoided starting on another.  While I do play games, they’re simply ones that get old after 10 or 15 minutes of play.  I follow this routine religiously 5 days of the week.  On the weekend, I follow the same routine unless there is a Quality Alternative.  The QA’s include a structured activity with the family such as seeing a movie or going dancing with my wife (we love live music).  The other source of QA’s is getting time in my own Machine Shop where all of this started.  That’s what I had to do to scrape up an extra 10 hours a week to start Bootstrapping with a Day Job and that’s what I’ve kept to since leaving the Day Job.

On vacations, I bring a laptop that is equipped to do all of this work.  I have access to everything from any computer thanks to the magic of Dropbox, 1Password, and having signed up for as many Cloud/SaaS alternatives as I could.  I prefer not to write code on vacation as time is short and that’s not why I am there, but I can and do keep up with Customer Service and will even manage to write a bit of content–more like 1 or 2 articles a week instead of 5.  If I know I will be travelling, I tee up 3 or 4 articles that can be published before I leave.

That, in a nutshell, is the life of this busy bootstrapper.  From my Bootstrapping Odyssey post you can get an idea of the marketing results and deliverables that can be accomplished on such a schedule.  From a coding perspective, Github suggests I committed about 900,000 lines of code (Adobe Flex for the most part) during 2012.  I only worked full-time the last half of 2012, so hopefully I can do more in 2013.

I love the Bootstrapper’s life I have found.  It’s hard work, sure, but I’d be working just as many hours at some Venture-Funded Startup if I wasn’t doing this.  I know, because I’ve done that 6 times before.  I’ve also had the luxury of taking long periods off between gigs. It takes time to find the right position at an executive level.  Periodically, I consider whether I would be happy retired and living off the fat of the land.  Then I spend whatever money I’ve made on silly toys in a move akin to the old explorers burning their ships in the New World so there can be no turning back.  Life is empty for me without the act of creating something–products, companies, new relationships, new experiences, and new interests.  Perhaps it is my sense of mortality, but I realize after just a couple of months that I haven’t yet accomplished everything I want to in life and it’s time to get back to work.

As for the loneliness aspect, the guys described in the CNN article need to get out more or something.  I miss coffee with co-workers, but I have always been an extrovert at heart and keep friends and contacts for years and years.  I’ve made a wealth of new ones as part of CNCCookbook, so the journey continues.  I was talking to one developer friend about Bootstrapping and he wondered aloud whether it would be possible to work from Venice, Italy.  I opined as how if the company were successful enough, I’d encourage it just so I could fly there periodically to meet with him.