This one resonated a lot. Definitely feeling the pull to simply work for myself and put an end to the crazy expectations others demand of leaders in a company.
This resonated a lot with me I am exactly in the same boat where I also feel I am too old to grind and too young to retire.
I think one of the things that people struggle with with starting a business is that generally there is so much societal pressure to make a business really big that unless you aim for a big business, you don’t think that you are successful, which is a mindset that needs to be changed and I love that you wrote the article that even if the business is small but financially sustainable and let you do what you want to do is still a very good option.
We need more more write ups like this in the world to show people that you don’t have to be have to go to corporate life or you don’t have to like not doing anything. Thank you so much for writing.
This spoke to me at this stage of my life. I still want to create, contribute, and build something meaningful, but no longer believe that success has to require constant expansion or consume the rest of one’s life.. A smaller, intentional way of working feels less like compromise and more like clarity..
All of this! I’m in my mid 50s. And even though I started my first business when I was 30, I do everything so differently now. And I look at these 20 and 30 somethings that are hustling, grinding, and all that stuff, and I think, “just you wait…” 😂
Big doesn’t mean success for me anymore. It could be of course…but it also could be not. It took me time to understand what “success” mean for me specifically
I have the exact same philosophy. I say that there’s a “world in between” leaving work and retirement. And we are the first generation to have the luxury to be able to explore that world as pioneers.
I have done something similar. I retired at 43 from Big Tech. Then my Side project. Code Like A Girl became my main thing. But I do it on my own terms.
Spot on. I left the grind to start my own passion travel tour company at 50. The hardest thing has been keeping the desire to grow it in check. I wanted small and no employees and for 15 years it's been an amazing run. Small and manageable is wonderful.
I’m in my 70s, and this may be the best way to describe where I am.
Too young to retire in my mind. Too old to waste my remaining years on the grind.
I still want to build. I still want to teach. I still want to matter.
I just no longer believe any of those things require sacrificing my time, my health, or the people I love.
Maybe the Third Act isn’t retirement. It’s ambition with better boundaries.
This one resonated a lot. Definitely feeling the pull to simply work for myself and put an end to the crazy expectations others demand of leaders in a company.
This resonated a lot with me I am exactly in the same boat where I also feel I am too old to grind and too young to retire.
I think one of the things that people struggle with with starting a business is that generally there is so much societal pressure to make a business really big that unless you aim for a big business, you don’t think that you are successful, which is a mindset that needs to be changed and I love that you wrote the article that even if the business is small but financially sustainable and let you do what you want to do is still a very good option.
We need more more write ups like this in the world to show people that you don’t have to be have to go to corporate life or you don’t have to like not doing anything. Thank you so much for writing.
This spoke to me at this stage of my life. I still want to create, contribute, and build something meaningful, but no longer believe that success has to require constant expansion or consume the rest of one’s life.. A smaller, intentional way of working feels less like compromise and more like clarity..
All of this! I’m in my mid 50s. And even though I started my first business when I was 30, I do everything so differently now. And I look at these 20 and 30 somethings that are hustling, grinding, and all that stuff, and I think, “just you wait…” 😂
Thanks for sharing your experience Rob 🙏🏻
Big doesn’t mean success for me anymore. It could be of course…but it also could be not. It took me time to understand what “success” mean for me specifically
I have the exact same philosophy. I say that there’s a “world in between” leaving work and retirement. And we are the first generation to have the luxury to be able to explore that world as pioneers.
You just wrote a story mirroring my last 18 months. It started as a vague Substack idea, then grew into a 12-person firm.
Yes I completely agree, it makes perfect sense to have something that fits into your life.
I have done something similar. I retired at 43 from Big Tech. Then my Side project. Code Like A Girl became my main thing. But I do it on my own terms.
I feel like this is refreshing to read from someone who builds business not to become the next big thing but to focus on building things that matters.
Also validated because knowing that someone out there chasing what I always wanted and strive with that life.
Aspired to be like you someday.
the bit about not rebuilding all the complexity you spent a career learning to navigate
Spot on. I left the grind to start my own passion travel tour company at 50. The hardest thing has been keeping the desire to grow it in check. I wanted small and no employees and for 15 years it's been an amazing run. Small and manageable is wonderful.
We (talented individuals and communities) need more small businesses that are about the work and the people, not the scale and the money.
I really love how you articulated this. It resonates