“I Wish I Would Have Worked More” – On Being a Time Tyrant

“I Wish I Would Have Worked More” – On Being a Time Tyrant post image

“Then there is the most dangerous risk of all– the risk of spending your life not doing what you want on the bet you can buy yourself the freedom to do it later.” — Randy Komisar, The Monk and the Riddle

Vague social pressure– social inertia– was a problem for me in my 20’s. I found it difficult to identify the things I wanted to spend my time on. Instead, I’d often go with the flow and be disappointed that me and my group of friends weren’t ‘doing more.’ Not cool!

I’m mostly over this now. I have clearer ideas on how I want to spend my time, and I don’t mind expressing my priorities to others.

Although pretty rare in the normal population, protecting time is common amongst people committed to their work and art. It’s rare to meet people like this, and I treasure every time I meet or read about somebody who gets energy from their work.

Stephen King, who has managed to write a lot of books, wrote that he wakes up everyday and works until he puts 2,000 words to paper. With very few exceptions, he’s done this every single day. He’s set up his environment and relationships to support his routine.

Ernest Hemingway, who also wrote a lot of books, hired a large man to stand outside the gate of his Key West home. The man used to say to visitors, who were hoping to meet the famous writer, “I’m mista Hemingway!” 

Steve Jobs, who is known for putting the sum total of human knowledge into your pocket, is famous for calling vendors, co-workers, and journalists at any hour of any day. Anytime, it seems, was a good time to be changing the world.

99% of people aren’t entrepreneurs. 99% of people don’t write novels. 99% of people don’t have a mission. 99% of people have different ideas on how time ought to be spent.

The cliche goes that nobody has ever been on their deathbed saying: “I wish I would have worked more.” And I’m sure that’s true if they were doing something just for the money.

But imagine if somebody’s work was their passion, their energy, their life and mission. But instead they sat around at bars. Or they got a job they hated. Or they went back to school to get a degree they didn’t need. Or they got guilt-tripped into an overbearing community group. Or they picked up the phone every time and said “yes.”

“I wish I would have worked more” might be exactly what they’d say.



PS, check out Stephen Fry: “the work is more fun than the fun.”

PPS, if you’d like to get on my private mailing list, just put your email address in to the form below:

Published on 01.09.12
  • Benjamin Washington

    Great stuff! I’ve saved the Stephen King text, it compounded what you said in a recent podcast, through pure quantity you can get quality. Keep posting dude!

  • Simplypools

    That’s great stuff dude. Love the 99% part. Because 99% won’t read this post. But that’s what your trying to change right? Keep up the great work.

    San Clemente, CA

  • staceyjamie


  • Jdcooper1999

    A good read for a Monday morning filled with questions about my goals for 2012

  • Ian

    Another great way to break social inertia is to leave the country. :) It’s tough to be influenced by your peers when your on the other side of the planet. Thanks for the motivation! I’m a big fan of your blog.

  • Bali Bro! In the six months or so that I’ve known you your writing just keeps getting better. Very impressed man. 

    Interesting concept here about getting pushed and pulled by the tide of friends, family and other commitments coming our way constantly. I still fight this instinct to go follow the crowd everyday. 

    I grew up as the kid that wanted to please. The oldest of four kids, I started off pleasing my parents. Then in high school, college and beyond it was pleasing friends and saying “yes” to every social opportunity that came down the pike because “I might just miss something you know”.

    It wasn’t until much later in life (my late thirties) that I started to realize that it’s not about everyone else. I decided to get my s$#% together and find something I was passionate about. I “thought” I was passionate about running a company and making lots of money. Don’t get me wrong, that is important to me, but I thought that this was my mission. I found out after owning and running my own company for eight years that for me its got to be something more important than just the money.

    If I am not creating something and adding value to either my life or someone else’s, it’s really not worth it. I must know that the products I develop or the things I write are useful for people. Building interesting products that either make people more productive or keep them engaged – that’s my passion.

  • Elisa

    GREAT post Dan – can definitely relate to this one and actually looking forward to moving West to reduce some of the distractions… is it mean that I call it that??

  • “social inertia” I had to google that to figure it out, I have done more than my fair share of following the crowd.. I think around 40 you get to a point where you just say f{*^ it and start doing what you want. Kinda makes me think of the bathroom example on one of your podcasts.

  • Just as Arnold says….work 18 hours a day and sleep for 6. Need more sleep?
    Sleep faster. Whats up Dan, long time…. 

  • Once again, another awesome post.

    I recently got let go of my job out here in Midwest (after 5 months, first time in corporate world). Can I say, super relieved. The team I was working on there was essentially “poison” to me, so it is nice to breakaway from that. This experience really helped me out with understanding what I don’t like. Thankfully, I didn’t get sucked into that job for more than 1 year, let alone, 5 or 10 years. Never will I move away from the coasts, for one thing (love surfing, and realized how much I missed the oceans).

    I’m on my way with collaborating with designers and writers from all over. It’s great. Now, it’s just deciding where home will be for me, haha.Happy 2012 to yea Dan!

  • Btw, is that a shot of NJTransit train with your header photo?

  • Dan


  • Dan


  • Dan

    Thanks a lot for that Cam! Appreciate that. I’m curious my impression was you are still running your company, do you worry that your employees would find out that you are losing your passion for running the biz? 

  • Dan

    Can feel ya on the poison situation. I once told an entrepreneur that I never wanted to deal with a lame team again and he said “not possible…. you need to put up with lame-folks” and I thought… “um…. no….” and I walked.

    Happy 2012 Harrison.

  • Dan

    haha. :D

  • Dan

    hopefully google will return this blog post!! :D

    can’t remember that example! 

  • Dan

    cheers!! :D   

    not mean in my book! 

  • Dan

    yeah man very good point there. i’ve often said that’s one of the benefits of bouncing. especially here in SEAsia lots of like-minds. very open and entrepreneurial.

  • Dan

    you too!! !

  • Dan

    don’t know! never thought of that… :)

  • Dan

    will do ! thanks…

  • Actually it’s quite the opposite. My passion is providing a better user experience than we have in the past. That passion, as well as encouraging more open and honest conversations between team members seems to be helping to improve our overall culture. We are attempting to be more objective about our products – honestly evaluating the good and the bad. The team is really getting behind an Agile development framework and the idea of short iterations geared to help us learn what customers like and what they don’t like.

    Furthermore, I encourage my team to start side projects that they are passionate about whether its blogging, building software, running a non-profit, etc. We have one guy on my team who is a great PC-based game developer. He is doing this on the side and if a collaboration opportunity arises, we are open to looking at it.

  • The secret for me is to create at least one niche site every day. If I do that then at least I’m doing something. Sometimes it’s a good site. Sometimes it’s a dud, but at least I’m doing something.

  • Dan

    damn. that’s not bad at all! 

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  • Gordon

    Dan, got to say, this post really made me look into a lot of things. It really lit the fuse to change in my life. Hopefully I’ll be able to return the favour one day.

  • Dan

    well cheers thanks for saying that! 

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  • Jorge

    In my view, “fun” as a motive is just immature and unintelligent. It takes much more self-knowledge and savvy to find something to do that both offers real value and that you enjoy doing for its own sake. For instance, real painters love to paint; real writers love to write. The money is a by-product. What can be more dreary and soulless than just wanting money?

    Business aside, searching for “fun” reveals a rather shallow and cultureless individual. Too many people run around the world searching for who knows what because essentially they are voids, without any depth of awareness or refinement. They look for place that are still “unspoiled” by people like themselves! The idea that these places are simply normal perhaps escapes them, and even more so the idea that happiness is something that wells up from inside you and cannot be plastered on to a basically vacuous and narcissistic soul. “Tourist” places all over the globe are filled with just the same shallow and pathetic individuals, who would find life intolerable without alcohol, “partying,” and the like. Decadence and degeneracy are everywhere and they pass for “cool,” and “fun.” They have “spoiled” a good bit of the planet along with the incessant search for profit and “opportunity.”

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