I love this series so much! I had the secret dream of becoming a full-time youtuber for a while until I took a 6-month sabbatical and tried it out. I realized it doesn't fulfill me enough to be my main thing. I still love it as a side thing and now I feel a lot more satisfied with how much time I have to put towards it. Before that, I was always frustrated with not having more time for making videos.
Now, I wonder if sometimes we even know deep down that our dreams aren't what we really want but we don't have a better idea yet, so we are scared to challenge it by trying it out, at which point we would be forced to face the fact that we have no idea what to do with our lives. I think that might have been true for me. But since I have tried that and realized that destroying your dreams is not that bad (it was actually exciting to think up and try out some new ideas), I have less fears around just trying things out on a small scale or on the side or for a limited time - and at least it gets me closer to finding my path every time.
Anna - thanks for sharing. What you said is profound.
How great to make that conclusion earlier... rather than holding onto that woulda-coulda-dream your whole life. And who knows, maybe you return to videos again later, but now you do it with more intentionality (imagine waiting, then finding out later it WASN'T that great of a dream?!? Yikes!).
I think a lot of it comes down to thinking that achieving a dream = finding "the answer." It's having the ultimate control over life, a sense that we conquered it. But we'll never have that feeling, despite our efforts.
Thanks Rick! Yes, making videos is actually still a big part of my life, now I just see it more as a marketing strategy for a different business rather than being the main thing I do and I enjoy it much more that way. And I'm sure this will evolve over time, as you say!
Excellent post. I think you hit all the major pieces. I am at the end of a two year sabbatical after selling a company, and at the precipice of jumping back in. This really crystallizes many of the issues foremost in my mind such as the “perfect day” that I’ve built up over two years off, and the focus on process required (boundaries and means) that would entice me to return to the world of startup building in a saner way.
Thanks for sharing your story Ben. I think that coming at a venture with that attitude in mind, versus the typical "what's the opportunity" (that usually completely disregards the impact to ones' personal life) is the way to go.
I’ve spent my whole adult life grinding hard to get here, with “here” being financial freedom. Now that it’s here I’m lost. So many people ask me why I’m leaving a great career at 55. I can’t say “because I’m rich”. So, the answer becomes muddled. I wonder if they think I got run off. I agree with the founder who said, that there are obvious things we should do: non-profit, sitting on Boards, etc. but none of it fulfills me. I agree. It turns out after grinding my ass off, the most daunting thing I face is the fear of unlimited free time. Good problem to have, but it’s still a problem. (BTW, my newsletter link is below)
Thanks Tom for sharing your story. Sounds like your story resembles many of the people who I interviewed. And what can make your situation hard is that you can feel like you're all alone - no one around you is doing the same thing, no one understands your pain, everyone thinks your life must be great. That's what makes this topic so compelling...
I love this series so much! I had the secret dream of becoming a full-time youtuber for a while until I took a 6-month sabbatical and tried it out. I realized it doesn't fulfill me enough to be my main thing. I still love it as a side thing and now I feel a lot more satisfied with how much time I have to put towards it. Before that, I was always frustrated with not having more time for making videos.
Now, I wonder if sometimes we even know deep down that our dreams aren't what we really want but we don't have a better idea yet, so we are scared to challenge it by trying it out, at which point we would be forced to face the fact that we have no idea what to do with our lives. I think that might have been true for me. But since I have tried that and realized that destroying your dreams is not that bad (it was actually exciting to think up and try out some new ideas), I have less fears around just trying things out on a small scale or on the side or for a limited time - and at least it gets me closer to finding my path every time.
Anna - thanks for sharing. What you said is profound.
How great to make that conclusion earlier... rather than holding onto that woulda-coulda-dream your whole life. And who knows, maybe you return to videos again later, but now you do it with more intentionality (imagine waiting, then finding out later it WASN'T that great of a dream?!? Yikes!).
I think a lot of it comes down to thinking that achieving a dream = finding "the answer." It's having the ultimate control over life, a sense that we conquered it. But we'll never have that feeling, despite our efforts.
Thanks Rick! Yes, making videos is actually still a big part of my life, now I just see it more as a marketing strategy for a different business rather than being the main thing I do and I enjoy it much more that way. And I'm sure this will evolve over time, as you say!
Excellent post. I think you hit all the major pieces. I am at the end of a two year sabbatical after selling a company, and at the precipice of jumping back in. This really crystallizes many of the issues foremost in my mind such as the “perfect day” that I’ve built up over two years off, and the focus on process required (boundaries and means) that would entice me to return to the world of startup building in a saner way.
Thanks for sharing your story Ben. I think that coming at a venture with that attitude in mind, versus the typical "what's the opportunity" (that usually completely disregards the impact to ones' personal life) is the way to go.
I’ve spent my whole adult life grinding hard to get here, with “here” being financial freedom. Now that it’s here I’m lost. So many people ask me why I’m leaving a great career at 55. I can’t say “because I’m rich”. So, the answer becomes muddled. I wonder if they think I got run off. I agree with the founder who said, that there are obvious things we should do: non-profit, sitting on Boards, etc. but none of it fulfills me. I agree. It turns out after grinding my ass off, the most daunting thing I face is the fear of unlimited free time. Good problem to have, but it’s still a problem. (BTW, my newsletter link is below)
Tom
https://witwisdom.tomgreene.com/subscribe
Thanks Tom for sharing your story. Sounds like your story resembles many of the people who I interviewed. And what can make your situation hard is that you can feel like you're all alone - no one around you is doing the same thing, no one understands your pain, everyone thinks your life must be great. That's what makes this topic so compelling...
Outstanding breakdown. I had this epiphany during Covid (I think a lot of people did - the one good thing that came out of it) https://open.substack.com/pub/beyondsurvival/p/the-cult-of-work?r=40ir&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false
Thanks for sharing. Will check it out.
Great stuff Rick. Love #5
Thanks Ed. "Expose your dreams to air" almost was my title for the piece!
Ventilate those dreams!
😂 or how bout “undress your dreams” for something a little more spicy