24 Comments
Oct 1·edited Oct 1Liked by Tim Denning

Tim, this essay didn't blow my mind. For a good reason. I'm going all in. I can't afford to quit my job yet but my free time is spent writing online. The longer I do it, the more interesting things happen to me.

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I love when people disagree. Your plan sounds solid Denis. What's the next step.

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Send more emails, get more clients, and post threads on X to get more email subscribers.

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No. Just no. The best feeling in the world is gazing at the stars in the woods. Maybe in the category of "getting paid" it's not bad though.

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Tim, I love your writing. And evermore folks need to read this. You made me realize I have work to do (still) to turn my passion for helping others into an obsession for grant writing. Thank you for this.

I do have a couple of quibbles; I have no idea what peculate means, and I had honors English from one of those $100,000 college degrees (so long ago it cost me $10k) that you describe. And I know the reference to Tommy Tucker, but I betcha few others do.

Finally, I would say to the world your year-long Masterclass is so worth it. Not just because it forces a discipline on me I didn’t know I would enjoy, but also because you and I both know that writing well is the key to success in any endeavor. AI will never replace a well-written piece like this, nor should it.

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Ah, so, grasshopper. I was genuinely stumped

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Perhaps speculate?

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Good stuff. It’s making me think. I’m adjusting my mindset and giving myself permission.

Thank you for that. ❤️🙏🏻

This very post is probably what makes you love your work. Love it.

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Hahaha Tim, my son literally gets paid for playing video games!! He is a software developer and works for a company that makes games. His job is to actually play to test the new ones and to make suggestions for improvement.

On another note: there were times in my life when I was obsessed with something, and although it might look like I still am (well, I am an artist, first of all a singer, and artists are all crazy, obsessed folks, no?, and people admire me for that I still keep singing, after all the difficulties I have gone through) but I keep losing the Big Spark that I used to have.

So this is exactly what I am working on.

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If you aren't obsessed, it's going to be real hard to beat the person in your field who is.

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Can you become obsessed by itineration?

As in I’m obsessed with wanting to live in Spain (UK is terrible) but I don’t jump out of bed of a morning excited and I still watch Netflix every evening because I’m not yet obsessed with my business that’s going to get me to Spain.

Instead of looking forward to going on holidays or weekends I want to wake up excited to work on my business. I guess it could be because I’ve procrastinated since I launched the idea and haven’t signed a client therefore it’s worn off.

So the question is can I become obsessed after I’ve done the work or does it need to be something you’re obsessed with before.

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I've been reading a lot of Charlie Munger recently and this reminds me of what he says about how he and Warren would spend all their time reading about companies. Obsessed.

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I'll smash you a beer when I see your face Mr. Denning.

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Imagine waking up excited every day because your work feels like play. What if the real glitch in the matrix is the 9-5?

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Value growth more than you value safety.

That's where I currently struggle. That's now my goal.

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Great article, Tim. Thanks. For me my obsessions and the resulting drive to earn a living on the internet have been like owning and driving around in a steam locomotive. You remember the coal car behind the locomotive and the guy regularly shoveling coal into the engine to keep it going? Every step along the way has been constantly shoveling more money into the engine, yet it doesn’t ever really go anywhere. With every piece of equipment or gear or software or website or class purchased there’s the time spent learning, and like you said, mastering it.

In my case particularly, I had spent over 2 years in development to get to the point that I was already engaging the next step and hiring out the professional help I needed (particularly traffic and funnels). I had quit my job as a food server a year before during Covid, and I was surviving and investing with the little unemployment I was receiving and working an odd-job here or there. Then the locomotive smashed into the brick wall of the station. The money I had been issued through unemployment was seized by the State of Hawaii. You know so that the then Governor David Ige could keep paying himself the third highest salary in the country with the third lowest population. I mean why would anyone want to help an entrepreneur create a business that would export products, generating state revenue outside of the tourist industry that our fair islands have been in the grips of since WW2?

So forced back to work months earlier than was on schedule, I spiraled deeper into poverty, the whole project was scrapped, and I had to shift gears again. So 3 years later I’m still waiting tables, still dependent on tourism, still impoverished. But now I’m completely homeless, rather than living out my Cherokee like I had been. Tim, if you want to talk about working for and with stupid people, you should come here to Hawaii Island! It’s pure torment.

So great things do come out of colossal failures. I really tuned into your processes of improvement. Now evident in my years of study, the Grand Master of self improvement is Kirk Hammett of Metallica. I too never stop progressing. So during that time period I created a visual art language and critical pieces that will lead to the long term solving of social justice. Again, why would anyone want to support that?

So now for years after, I’ve still been producing art and music at a prolific pace. I’ve just been able to adapt and find ways to do all my work on iOS and without expensive websites. Still not a penny earned, yet I’ve pushed forward and contributed to the arts and sciences, while being even further marginalized.

So at least with Substack I’m not shoveling money into the locomotive. Just time, which is more valuable and therefore more costly. But just like you said, I work when and where I want and need. No one tells me about what to write or how much. Now how I could earn a modest income from Substack is another complete mystery that may or may not ever be solved. The truth is that it’s through renunciation and un-attachment that we are free.

XX

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Family, friends and relationship are a massive part of life that should never been "given up" or "dumped." Does the internet provide you enough purpose and support that a partnership and relationship is not needed? Would love to hear your take on how you think an average reader that reads your blog and generally respects most of your takes is OK with the statement: "In my case it meant dumping my ex-girlfriend so I could get rid of all BS distractions and focus on online writing." This comes across narcissistic and incapable of empathy and emotion which are massively important to living a successful life. Does your wife feel like you could just "dump her so you can get rid of the BS distractions?" Most of your work is motivating. This is anti-motivating and unrelatable and I imagine for a lot of people. It is not weak to be multifaceted. You are a father, a husband and a writer. Can you re-write this post wearing all three hats please?

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for the avoidance of doubt, when i use the term "average reader", i am referring to what the readers of your work are "on average" - not describing the reader as mediocre or average!

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Yes, someone needs to write a book about this idea of play. It’s a huge concept and a better guideline for people seeking their passion. Instead of looking for your passion, look for what you do for fun, what you're good at, and what you would do if money weren’t an object.

Search for your play instead of your passion. Then, create an educational product or brand around your play and get paid for it.

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The reason I look forward to reading Tim daily is because he does something to my world view. Writing online is gathering tons of micro skills along the way that will put you 100x ahead of others and succeeding.

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Best one from a long time! It will, surely, give some thoughts to a lot of people!

I live about the same kind of life and you made me salivate today !

Thanks!

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