Loved this! Not a 2nd time founder, but was on the founding team of a few startups, now starting my own. Reading PG’s how to do great work always helps me stay grounded :)
Is obsession born from interest? Or is it born from perseverance?
The "obsession > obligation" framing creates a false dichotomy that could lead founders to abandon viable businesses when they hit inevitable difficult periods. Building anything significant involves seasons of both inspiration and perspiration.
This mindset creates a trap of constant dissatisfaction. The deeper lesson is learning to detach from outcomes while reframing challenges in ways that help you keep going. The founder journey – whether you're at $100K or $1B in revenue – inevitably includes periods of stagnation, setbacks, and comparison. Someone will always appear to be moving faster, raising more capital, achieving better margins, or attracting more prestigious investors. This reality never changes, regardless of your level of success.
Look at any enduring, successful company in the market today. Most took at least FIVE years just to get "something that works" and another 5 years to scale that solution. The companies we admire, the ones worth being "your life's mission" as you put, have typically been around for 10+ years. They didn't achieve that by founders jumping ship when passion temporarily waned.
Constantly questioning your level of "obsession" creates harmful thought patterns. You train your mind to focus on what "should" be rather than appreciating what is. This weakens your resilience and provides a convenient excuse for quitting when things get tough. By using "lack of obsession" as your escape hatch, you never develop the grit required to reach those breakthrough moments where genuine passion ignites.
I wonder if you've noticed that even your 'acceptance of blank white space' still shows signs of discomfort with directionless time. Your immediate pivot to structured hobbies – machine learning practice with daily posts, documented basketball training, Network School – suggests you're substituting one form of measurable productivity for another. Perhaps the deeper work isn't finding new activities to be excellent at, but developing comfort with periods where you aren't visibly progressing at all.
I disagree with you though ... there's a level of perseverance that's required to uncover if the idea will ultimately work out in the end (ofc). IMO, this shouldn't take years though.
A founder that quits after 3 months is different from a founder that quits after 4 years. There's no exact formula for success, but IMO the most important thing is organic pull towards the company.
I think Steve Jobs captures this sentiment well
"I have looked in the mirror every morning and asked myself: "If today were the last day of my life, would I want to do what I am about to do today?" And whenever the answer has been "No" for too many days in a row, I know I need to change something."
If you've been saying "no" for months and a year, then it's time to change because something is off about the idea. This is different from traction or revenue or success of the company, it's an organic pull, mystical energy that captivates the founder. Experience in entrepreneurship gives you the tools to locate that energy quickly while working on your startup and to determine if it's really there or not.
I pivoted to hobbies that had an organic pull. I believe if I'm able to dedicate hours to working on those hobbies for months, then that's a good sign it's real and authentic. Then the next step is to figure out how to structure those hobbies into a sustainable career which is the problem i'm trying to solve now!
That Jobs quote looks different when you examine his actual work. NeXT was a commercial failure that became the foundation for Apple's rebirth. Pixar nearly bankrupted him before succeeding. His return to Apple involved unglamorous work on supply chains and retail strategies.
Jobs contradicted this philosophy when he told teams "real artists ship" – he himself acknowledged that creation demands commitment even on days when the mirror would have told him "no."
The quote is a makes for a clean narrative when cherry picked from a Stanford commencement speech, but ignores a messier truth: Apple itself exists today precisely because Jobs ignored his own advice. Had he truly abandoned every pursuit that gave him consecutive "no" days, we'd have no Pixar, no iPhone, no Apple renaissance. The company you're using to read this post survived because Jobs rejected the seductive simplicity of his own quote.
When you say ideas shouldn't take years to validate, that reflects short-term thinking. I strongly prefer a long-term mindset. Any durable business, regardless of initial passion, takes years to truly unfold. Consider this: the average S&P 500 company is 33 years old, with giants like JPMorgan Chase (226 years), Citigroup (213 years), and Procter & Gamble (188 years) demonstrating extraordinary staying power. If their founders had abandoned ship when their "organic pull" waned, our economic landscape would look dramatically different. Building something meaningful requires thinking in decades, not quarters.
The "organic pull" or "mystical energy" framing creates unrealistic expectations about daily work. It suggests that without constant magnetic attraction to your work, something's fundamentally wrong. This perception stems from Silicon Valley's romanticized narrative of entrepreneurship that distorts what meaningful work actually feels like.
Now, on hobbies – let's be real. Of course they have an "organic pull" – they're literally defined as things we do for pleasure. But the moment you stake your livelihood on a hobby, everything changes. The incentives transform completely under financial pressure. This isn't some profound insight – it's practically a cliché to warn against "turning your hobby into a career" precisely because of this shift.
I don't mean to be overly antagonistic, but the dangerous aspect of your approach is that it creates a framework where temporary challenges become existential questions. By your constant evaluation of your "obsession level," you train their mind to look for exit signals.
Sounds good - thanks for your perspective - I'm sure there's not right answer and everyone has to find their own sources of energy / how to do great work. It sounds like for you it's years of grinding to see the magical result in the end - i think that's great and valid. I'm not sure everyone is built that way, but from what you're saying it sounds like some people are.
I feel what you are describing. Today is my first day after exiting the previous start-up where I spent 6 years - I wasn't a founder, but sometimes it felt like. I already had the phase of applying and exploring the next opportunities (I had an almost two-month-long notice period). Now, I'm in a similar place - genuinely exploring my own interests - reading, writing, learning.
I don't have any particular advice, but I'm keeping my fingers crossed for you 🤞
PS I do like Toby's recommendation on "How to do great work" - I always come back to this reading in moments of uncertainty.
Really enjoyed reading this Andy. I went through a lot of this with my 2nd startup after 9 years on my first. "I couldn’t bring myself to work on them unless I knew they would succeed" was very relatable. And your point on the importance of obsession made a lot of sense.
“9 years on your first” , that journey must’ve been filled with countless ups and downs , a ton of emotions - hoping the current journey is better or as good as your first one
I went through the same thought process as you during the “should I stay or should I go” phase.
I listed everything I disliked about my previous position to make sure I wouldn’t repeat the same mistakes. That was one of the most important parts of my rebuilding phase—because when you leave your former company, it feels like you’re leaving a piece of yourself behind.
I also thought about the kind of life I’d be proud of 60 years from now. That perspective helped me define goals today that would bring me closer to that long-term vision.
Ultimately, what helped me most was launching a new business quickly—without hesitating for too long. When you’re moving forward, there’s no room for doubt. Most people will tell you to take your time, to reflect, etc. But my way of operating is to always keep moving—no matter what.
As a second-time founder, I now have more ego than I did a few years ago, and I have a family (in my case). In other words, I have more to lose. If I overthink things, I’ll never take any moonshots and will probably end up joining a VC firm—which would be the “reasonable” choice given my situation.
But I don’t want to be reasonable. I want to do something great.
Just read your Substack article on your 2nd time founder journey. It really resonated with me, especially the part about starting businesses with zero knowledge. That's been my pattern across all 4 companies I've built, including my current project, making business tax compliance invisible and automatic.
One thing I've been wondering about though: what about the compound interest on all the knowledge we accumulate that we miss out on when constantly starting fresh?
Your article hit home. I've been in the same boat since selling my company 2 years ago - that first year was filled with false starts and the emotional journey you described feels all too familiar.
I was so disappointed in myself and beat myself up about not achieving anything in that first year after the exit. The self-doubt was crushing. Eventually I just focused on working out hard, playing table tennis (improved a ton!), running marathons, and leveling up my coding skills with AI.
Network School last year was a game-changer - I finally feel more at peace and blissful. I've reached acceptance and no longer doubt myself when I can constantly contend with the high-caliber people here at NS. That's given me even more space and confidence to work on the new thing.
Hey Andy, thanks for the article. Extremely acute insights into the psychology of ambiguity - and relatable (see my about page for why)! My question - assuming this is the polished, final product - what is the concrete, actionable process or algorithm by which you iteratively bring resolution to your ideas?
Loved this! Not a 2nd time founder, but was on the founding team of a few startups, now starting my own. Reading PG’s how to do great work always helps me stay grounded :)
Thank you for the love !
Is obsession born from interest? Or is it born from perseverance?
The "obsession > obligation" framing creates a false dichotomy that could lead founders to abandon viable businesses when they hit inevitable difficult periods. Building anything significant involves seasons of both inspiration and perspiration.
This mindset creates a trap of constant dissatisfaction. The deeper lesson is learning to detach from outcomes while reframing challenges in ways that help you keep going. The founder journey – whether you're at $100K or $1B in revenue – inevitably includes periods of stagnation, setbacks, and comparison. Someone will always appear to be moving faster, raising more capital, achieving better margins, or attracting more prestigious investors. This reality never changes, regardless of your level of success.
Look at any enduring, successful company in the market today. Most took at least FIVE years just to get "something that works" and another 5 years to scale that solution. The companies we admire, the ones worth being "your life's mission" as you put, have typically been around for 10+ years. They didn't achieve that by founders jumping ship when passion temporarily waned.
Constantly questioning your level of "obsession" creates harmful thought patterns. You train your mind to focus on what "should" be rather than appreciating what is. This weakens your resilience and provides a convenient excuse for quitting when things get tough. By using "lack of obsession" as your escape hatch, you never develop the grit required to reach those breakthrough moments where genuine passion ignites.
I wonder if you've noticed that even your 'acceptance of blank white space' still shows signs of discomfort with directionless time. Your immediate pivot to structured hobbies – machine learning practice with daily posts, documented basketball training, Network School – suggests you're substituting one form of measurable productivity for another. Perhaps the deeper work isn't finding new activities to be excellent at, but developing comfort with periods where you aren't visibly progressing at all.
Thank you for the perspective!
I disagree with you though ... there's a level of perseverance that's required to uncover if the idea will ultimately work out in the end (ofc). IMO, this shouldn't take years though.
A founder that quits after 3 months is different from a founder that quits after 4 years. There's no exact formula for success, but IMO the most important thing is organic pull towards the company.
I think Steve Jobs captures this sentiment well
"I have looked in the mirror every morning and asked myself: "If today were the last day of my life, would I want to do what I am about to do today?" And whenever the answer has been "No" for too many days in a row, I know I need to change something."
If you've been saying "no" for months and a year, then it's time to change because something is off about the idea. This is different from traction or revenue or success of the company, it's an organic pull, mystical energy that captivates the founder. Experience in entrepreneurship gives you the tools to locate that energy quickly while working on your startup and to determine if it's really there or not.
I pivoted to hobbies that had an organic pull. I believe if I'm able to dedicate hours to working on those hobbies for months, then that's a good sign it's real and authentic. Then the next step is to figure out how to structure those hobbies into a sustainable career which is the problem i'm trying to solve now!
That Jobs quote looks different when you examine his actual work. NeXT was a commercial failure that became the foundation for Apple's rebirth. Pixar nearly bankrupted him before succeeding. His return to Apple involved unglamorous work on supply chains and retail strategies.
Jobs contradicted this philosophy when he told teams "real artists ship" – he himself acknowledged that creation demands commitment even on days when the mirror would have told him "no."
The quote is a makes for a clean narrative when cherry picked from a Stanford commencement speech, but ignores a messier truth: Apple itself exists today precisely because Jobs ignored his own advice. Had he truly abandoned every pursuit that gave him consecutive "no" days, we'd have no Pixar, no iPhone, no Apple renaissance. The company you're using to read this post survived because Jobs rejected the seductive simplicity of his own quote.
When you say ideas shouldn't take years to validate, that reflects short-term thinking. I strongly prefer a long-term mindset. Any durable business, regardless of initial passion, takes years to truly unfold. Consider this: the average S&P 500 company is 33 years old, with giants like JPMorgan Chase (226 years), Citigroup (213 years), and Procter & Gamble (188 years) demonstrating extraordinary staying power. If their founders had abandoned ship when their "organic pull" waned, our economic landscape would look dramatically different. Building something meaningful requires thinking in decades, not quarters.
The "organic pull" or "mystical energy" framing creates unrealistic expectations about daily work. It suggests that without constant magnetic attraction to your work, something's fundamentally wrong. This perception stems from Silicon Valley's romanticized narrative of entrepreneurship that distorts what meaningful work actually feels like.
Now, on hobbies – let's be real. Of course they have an "organic pull" – they're literally defined as things we do for pleasure. But the moment you stake your livelihood on a hobby, everything changes. The incentives transform completely under financial pressure. This isn't some profound insight – it's practically a cliché to warn against "turning your hobby into a career" precisely because of this shift.
I don't mean to be overly antagonistic, but the dangerous aspect of your approach is that it creates a framework where temporary challenges become existential questions. By your constant evaluation of your "obsession level," you train their mind to look for exit signals.
Sounds good - thanks for your perspective - I'm sure there's not right answer and everyone has to find their own sources of energy / how to do great work. It sounds like for you it's years of grinding to see the magical result in the end - i think that's great and valid. I'm not sure everyone is built that way, but from what you're saying it sounds like some people are.
Interesting post, thanks, Andy!
I feel what you are describing. Today is my first day after exiting the previous start-up where I spent 6 years - I wasn't a founder, but sometimes it felt like. I already had the phase of applying and exploring the next opportunities (I had an almost two-month-long notice period). Now, I'm in a similar place - genuinely exploring my own interests - reading, writing, learning.
I don't have any particular advice, but I'm keeping my fingers crossed for you 🤞
PS I do like Toby's recommendation on "How to do great work" - I always come back to this reading in moments of uncertainty.
Patryk - thank you for the words! It means a lot and gave me a jolt of energy. Wishing you well on your journey as well.
Really enjoyed reading this Andy. I went through a lot of this with my 2nd startup after 9 years on my first. "I couldn’t bring myself to work on them unless I knew they would succeed" was very relatable. And your point on the importance of obsession made a lot of sense.
“9 years on your first” , that journey must’ve been filled with countless ups and downs , a ton of emotions - hoping the current journey is better or as good as your first one
Some readings that I consult for being inspired to do good work (in case its helpful for people)
Greg Brockman How to become an ML Practictioner https://blog.gregbrockman.com/how-i-became-a-machine-learning-practitioner
John Schulman Opinionated guide to ML research http://joschu.net/blog/opinionated-guide-ml-research.html
Richard Hamming You and Your Research https://www.cs.virginia.edu/~robins/YouAndYourResearch.html
Michael Nielsen Principles of Effective Research https://michaelnielsen.org/blog/principles-of-effective-research/
Paul Graham How to do great work
http://www.paulgraham.com/greatwork.html
Andrej Karpathy 10,000 hours Advice for ML beginners
https://www.youtube.com/watch?v=I2ZK3ngNvvI
I’m a second-time founder.
I went through the same thought process as you during the “should I stay or should I go” phase.
I listed everything I disliked about my previous position to make sure I wouldn’t repeat the same mistakes. That was one of the most important parts of my rebuilding phase—because when you leave your former company, it feels like you’re leaving a piece of yourself behind.
I also thought about the kind of life I’d be proud of 60 years from now. That perspective helped me define goals today that would bring me closer to that long-term vision.
Ultimately, what helped me most was launching a new business quickly—without hesitating for too long. When you’re moving forward, there’s no room for doubt. Most people will tell you to take your time, to reflect, etc. But my way of operating is to always keep moving—no matter what.
As a second-time founder, I now have more ego than I did a few years ago, and I have a family (in my case). In other words, I have more to lose. If I overthink things, I’ll never take any moonshots and will probably end up joining a VC firm—which would be the “reasonable” choice given my situation.
But I don’t want to be reasonable. I want to do something great.
Best,
Jules
Hey Andy,
Just read your Substack article on your 2nd time founder journey. It really resonated with me, especially the part about starting businesses with zero knowledge. That's been my pattern across all 4 companies I've built, including my current project, making business tax compliance invisible and automatic.
One thing I've been wondering about though: what about the compound interest on all the knowledge we accumulate that we miss out on when constantly starting fresh?
Your article hit home. I've been in the same boat since selling my company 2 years ago - that first year was filled with false starts and the emotional journey you described feels all too familiar.
I was so disappointed in myself and beat myself up about not achieving anything in that first year after the exit. The self-doubt was crushing. Eventually I just focused on working out hard, playing table tennis (improved a ton!), running marathons, and leveling up my coding skills with AI.
Network School last year was a game-changer - I finally feel more at peace and blissful. I've reached acceptance and no longer doubt myself when I can constantly contend with the high-caliber people here at NS. That's given me even more space and confidence to work on the new thing.
- Kuan Yu
Hey Andy, thanks for the article. Extremely acute insights into the psychology of ambiguity - and relatable (see my about page for why)! My question - assuming this is the polished, final product - what is the concrete, actionable process or algorithm by which you iteratively bring resolution to your ideas?