Hey Guys, just listened to this, identified with so much here from both of you: long sabbatical, old career losing lustre, embracing a new chapter of life, wanting a more meaningful existence. Great interview!
always of fan of your stuff michael. For #5, do you feel like the need for the identity shift is only "possible" because both you and Rick have achieved some level of financial/career success?
Another way to put it is, would you even be contending with this question if you left your previous ventures without any big financial wins?
That's a great question, and it’s something I think about often. Financial and career success definitely provide a certain level of freedom that brings these kinds of reflections to the forefront.
I’ve also noticed that this type of questioning isn’t limited to those with financial success. It’s common among people in their mid-to-late 30s and 40s, but I’ve also seen it happen with people in their 20s.
It often occurs when the external success they’ve worked so hard for doesn’t bring the fulfillment they expected. Some end up raising the bar, continually chasing the next milestone, while others pause to ask why they’re doing it at all, reevaluating whether their goals actually align with their values.
It’s something that can surface as a quarter-life or mid-life crisis. Mine just happened to coincide with my 40th birthday.
I think the financial/career success ACCELERATED the questioning and shift.
As in, the questions were coming anyways, they just came a lot sooner by achieving success + taking time away. It would have hit me in a big way later in life. So in a way, I front-loaded my existential crisis!
A lot of what I feel like I'm doing is telling people behind me what may be coming around the corner...
As someone who hasn't achieved the financial success (yet), and ALSO dealing with the questions, I think it's easy to feel shitty about myself, but there's a bit of solace in hearing how you guys are working through it all.
Just want to send some encouragement your way. You are not alone. Michael, Rick, and I are probably 10-15ish years older than you and we're still trying to figure out the meaning of work. In some ways these answers are never final, as every season of life brings new questions. When I was younger I was always looking for the "universal answer" or the "one right answer" to things. As I got older I realized there are very few such answers. Every person has to answer the questions for themselves, at every stage of life, in a way that works for them.
Most people deal with these existential career questions at some point, regardless of financial situation, or sometimes because of their financial situation. A startup exit, a mid-life crisis, getting laid off, or simply being disillusioned with one's job can all be catalysts to trigger thinking about it, but you don't need any of those things to ponder the questions, in fact it might be even better if you think about them proactively.
So it's good that you're dealing with these questions now, while you're relatively young in your career, and have time to make alterations. The worst possible time to deal with them is late in life, when it's too late to change anything, and all you're left with is regret.
I would also encourage you to do all you can to stop comparing your situation to others who have financial success or seem to have figured more things about. Asians seem to be born with this trait so I know how hard it can be. I assume that's maybe part of why you feel bad. You have a unique path to walk in the world, that won't look like anyone else's. It may or may not include massive financial success. It might include moderate financial success. Or even struggle. At the end of the day your life is unique to you. Embrace who you are, how you're wired, what you're capable of doing, and the unique path the universe has laid out for you. It'll help you feel a little less shitty.
thanks Dave, appreciate this! Been working a lot on how to rethink my own life regardless of outcome, what kind of work I want to do, and I feel that I'm making progress. Will be dope to catch up on this thread in a year or two :)
Rick's great! Looking forward to this episode!
Hey Guys, just listened to this, identified with so much here from both of you: long sabbatical, old career losing lustre, embracing a new chapter of life, wanting a more meaningful existence. Great interview!
always of fan of your stuff michael. For #5, do you feel like the need for the identity shift is only "possible" because both you and Rick have achieved some level of financial/career success?
Another way to put it is, would you even be contending with this question if you left your previous ventures without any big financial wins?
Thanks so much!
That's a great question, and it’s something I think about often. Financial and career success definitely provide a certain level of freedom that brings these kinds of reflections to the forefront.
I’ve also noticed that this type of questioning isn’t limited to those with financial success. It’s common among people in their mid-to-late 30s and 40s, but I’ve also seen it happen with people in their 20s.
It often occurs when the external success they’ve worked so hard for doesn’t bring the fulfillment they expected. Some end up raising the bar, continually chasing the next milestone, while others pause to ask why they’re doing it at all, reevaluating whether their goals actually align with their values.
It’s something that can surface as a quarter-life or mid-life crisis. Mine just happened to coincide with my 40th birthday.
I think the financial/career success ACCELERATED the questioning and shift.
As in, the questions were coming anyways, they just came a lot sooner by achieving success + taking time away. It would have hit me in a big way later in life. So in a way, I front-loaded my existential crisis!
A lot of what I feel like I'm doing is telling people behind me what may be coming around the corner...
As someone who hasn't achieved the financial success (yet), and ALSO dealing with the questions, I think it's easy to feel shitty about myself, but there's a bit of solace in hearing how you guys are working through it all.
Hey David,
Just want to send some encouragement your way. You are not alone. Michael, Rick, and I are probably 10-15ish years older than you and we're still trying to figure out the meaning of work. In some ways these answers are never final, as every season of life brings new questions. When I was younger I was always looking for the "universal answer" or the "one right answer" to things. As I got older I realized there are very few such answers. Every person has to answer the questions for themselves, at every stage of life, in a way that works for them.
Most people deal with these existential career questions at some point, regardless of financial situation, or sometimes because of their financial situation. A startup exit, a mid-life crisis, getting laid off, or simply being disillusioned with one's job can all be catalysts to trigger thinking about it, but you don't need any of those things to ponder the questions, in fact it might be even better if you think about them proactively.
So it's good that you're dealing with these questions now, while you're relatively young in your career, and have time to make alterations. The worst possible time to deal with them is late in life, when it's too late to change anything, and all you're left with is regret.
I would also encourage you to do all you can to stop comparing your situation to others who have financial success or seem to have figured more things about. Asians seem to be born with this trait so I know how hard it can be. I assume that's maybe part of why you feel bad. You have a unique path to walk in the world, that won't look like anyone else's. It may or may not include massive financial success. It might include moderate financial success. Or even struggle. At the end of the day your life is unique to you. Embrace who you are, how you're wired, what you're capable of doing, and the unique path the universe has laid out for you. It'll help you feel a little less shitty.
thanks Dave, appreciate this! Been working a lot on how to rethink my own life regardless of outcome, what kind of work I want to do, and I feel that I'm making progress. Will be dope to catch up on this thread in a year or two :)