Thanks for this piece David. I love your honesty and transparency.
The idea of trying to pick the right path reminds me of something from the book 4000 Weeks by Oliver Burkeman. He talks about decision making and how the awareness of the finitude of our lives affects our ability to make decisions. Knowing we've got a limited amount of time makes us aware that any path we take means closing down an infinite number of alternative paths.
I loved your clear breakdown of monthly hours worked and annual revenue. Using a revenue per hour metric sounds like a useful way to understand which path to choose. The added question for me is also about the quality of experience of each of those hours. 4 hours a month on Talent Collective sounds great given the annual revenue it generates but if those 4 hours are painful then could your time be spent more enjoyable (and creatively)? Just a thought to illustrate the point that it isn't just about revenue per hour worked.
One of the ways that I've found useful in terms of making choices is finding out how it meets my core needs. For instance 3 of my core needs are learning, play and friendship. If the work that I do helps me grow as a person, gives me space to experiment without having specific goals and I do it in the company of people I care about then it's definitely worth considering. I call it Leading with Needs.
I'd love to have you join us on our Friday Fireside webinars to talk about your sabbatical and your current space of not knowing (living a liminal life) and how you're tackling choosing the next path. Would you be up for that?
Nice to see all of these potential paths :). I’m in an eerily similar place. A next step I might explore is asking which of these paths do you still have the most questions about. Rather than “pick” one I might try to prototype a few (I.e. make a personal investment before raising a fund, try building an mvp of one of the micro saas products, etc). Good luck!
Excellent post, David! Thanks for going deep and being honest. I've been exploring similar themes at my current career stage. I've realized for quite a while I want to give back to and mentor the next generation of community builders, connect and collaborate more with other fellow senior community pros like yourself, and step outside the community industry to inspire and challenge organizations senior leaders in other sectors to leverage the power of community within amd outsode the organization. Part of my journey lately had been the realization that it's time to begin to write a book about the historical impact and potential power of community on business. Keep up the great writing and open exploration. You're inspiring us all!
the talent path seems like a no brainier in terms of the cash-gain:time-input ratio, it could even become a side thing whilst you're pursuing writing more
i appreciated your candid reflections on being another white man leading a fund, that said i feel like there are lots of underrepresented community-builder operators you could tap into for potential partners, i could help you build a list as a few folks come to mind
as compassionate as your views are, the systems that oppress aren't going away in the near term, it could be good for representation in the long run to have someone with your optics AND progressive views to be in the ecosystem as an investor. as you say building on the amazing legacies arlan and lolita have started 💪🏾
Financial independence for me has come investing in various strategies, I don't think it all has to come from one source.
For me this looks like a rental property, I (co)own one business, I do small consulting, I've done some seed investing, I run a paid membership, I experiment with community training/cohorts, I created a side community for indie founders, I'm now also exploring the idea of creating a product.
My main strategy is to follow what I love doing, the less it feels like work, the better. But also, everything is really interconnected. Relationships in my indie world definitely support me in my community world. I love being a part of them both and as a result my work community work has a big hint of 'indie' in it.
Also, whilst I do things that don't scale (like consulting), I find these things a great way to get paid to do even more learning which in turn influence my other work. I guess the trick is to take on work that aligns with where you think you want to head.
I have on several occasions wondered to myself, "how in the world does Rosie do it all?!" I'm consistently impressed with how much you're able to put out into the world.
I've functioned similarly in the past. I like to add lots of pieces together. I'm kind of curious what it would look like for me to focus on just one thing for a while. It feels unnatural for me, so just trying to stay aware of how I'm feeling, when I want to add something, and make sure it's contributing to my goals and priorities.
Love the transparency, thanks for sharing these paths and your underlying thoughts David.
For what it's worth, here are some ideas and questions that came up as I read your post:
- In the AltMBA, we work on a process for decision making where we lay out all of the options (e.g., "doing nothing" to "conquering the world" and everything in between, and the criteria you have to meet to be happy (or achieved). Very similar to what Carlos Saba suggested.
Then list out the criteria about the things you care about and grade each option against these things you care about.
Matthew Encina did something similar in this post, and it's really inspiring to see how to decide his next career path:
- And to pull on the core needs thread, if we zoom out, do you have a vision of where you see yourself in five years? Where would you like to be, what would you like to have accomplished? Where do you see the industry potentially heading, and what does it need to get there? What sucks? Are there things you could offer in there that also align with your achievement and happiness criteria?
- Are there things that light you up, want to research late in the night and tell your friends or community?
- What do you care about enough to build something about it and care for a long time?
Not sure these questions make sense, but I hope anything here helps. :)
and tbh there's not a ton that really lights me up right now
the one thing I'm enjoying is writing here on the newsletter, and have already started working on some pieces that have been in my head for a long time, that I've never written down. So while the newsletter isn't likely to be the moneymaker, it's where I feel drawn to spending my time right now.
TLDR is you only need to make 4 (arguably less) great decisions a year. This means to take your time with it, and not make a decision just because you feel like you must do something and take action. Going for walks without headphones could be more “productive” than choosing something just to do something.
You probably know this well based on your decision to take time off and think/journal about several different paths. Wishing you the best of luck. ❤️
Thanks for this piece David. I love your honesty and transparency.
The idea of trying to pick the right path reminds me of something from the book 4000 Weeks by Oliver Burkeman. He talks about decision making and how the awareness of the finitude of our lives affects our ability to make decisions. Knowing we've got a limited amount of time makes us aware that any path we take means closing down an infinite number of alternative paths.
I loved your clear breakdown of monthly hours worked and annual revenue. Using a revenue per hour metric sounds like a useful way to understand which path to choose. The added question for me is also about the quality of experience of each of those hours. 4 hours a month on Talent Collective sounds great given the annual revenue it generates but if those 4 hours are painful then could your time be spent more enjoyable (and creatively)? Just a thought to illustrate the point that it isn't just about revenue per hour worked.
One of the ways that I've found useful in terms of making choices is finding out how it meets my core needs. For instance 3 of my core needs are learning, play and friendship. If the work that I do helps me grow as a person, gives me space to experiment without having specific goals and I do it in the company of people I care about then it's definitely worth considering. I call it Leading with Needs.
I'd love to have you join us on our Friday Fireside webinars to talk about your sabbatical and your current space of not knowing (living a liminal life) and how you're tackling choosing the next path. Would you be up for that?
love this advice - i'll give some thought to what my 3 core needs are
how did you go about narrowing down your needs to those core 3?
I did a webinar about the concept of creating a Needs Compass. I hope you find it helpful - https://vimeo.com/673714020/89dd1d7f98
Nice to see all of these potential paths :). I’m in an eerily similar place. A next step I might explore is asking which of these paths do you still have the most questions about. Rather than “pick” one I might try to prototype a few (I.e. make a personal investment before raising a fund, try building an mvp of one of the micro saas products, etc). Good luck!
totally - whatever I do I should start simple first. good reminder
Excellent post, David! Thanks for going deep and being honest. I've been exploring similar themes at my current career stage. I've realized for quite a while I want to give back to and mentor the next generation of community builders, connect and collaborate more with other fellow senior community pros like yourself, and step outside the community industry to inspire and challenge organizations senior leaders in other sectors to leverage the power of community within amd outsode the organization. Part of my journey lately had been the realization that it's time to begin to write a book about the historical impact and potential power of community on business. Keep up the great writing and open exploration. You're inspiring us all!
the talent path seems like a no brainier in terms of the cash-gain:time-input ratio, it could even become a side thing whilst you're pursuing writing more
i appreciated your candid reflections on being another white man leading a fund, that said i feel like there are lots of underrepresented community-builder operators you could tap into for potential partners, i could help you build a list as a few folks come to mind
as compassionate as your views are, the systems that oppress aren't going away in the near term, it could be good for representation in the long run to have someone with your optics AND progressive views to be in the ecosystem as an investor. as you say building on the amazing legacies arlan and lolita have started 💪🏾
really appreciate that feedback abadesi
Financial independence for me has come investing in various strategies, I don't think it all has to come from one source.
For me this looks like a rental property, I (co)own one business, I do small consulting, I've done some seed investing, I run a paid membership, I experiment with community training/cohorts, I created a side community for indie founders, I'm now also exploring the idea of creating a product.
My main strategy is to follow what I love doing, the less it feels like work, the better. But also, everything is really interconnected. Relationships in my indie world definitely support me in my community world. I love being a part of them both and as a result my work community work has a big hint of 'indie' in it.
Also, whilst I do things that don't scale (like consulting), I find these things a great way to get paid to do even more learning which in turn influence my other work. I guess the trick is to take on work that aligns with where you think you want to head.
I have on several occasions wondered to myself, "how in the world does Rosie do it all?!" I'm consistently impressed with how much you're able to put out into the world.
I've functioned similarly in the past. I like to add lots of pieces together. I'm kind of curious what it would look like for me to focus on just one thing for a while. It feels unnatural for me, so just trying to stay aware of how I'm feeling, when I want to add something, and make sure it's contributing to my goals and priorities.
Appreciate you taking the time to comment Rosie!
Love the transparency, thanks for sharing these paths and your underlying thoughts David.
For what it's worth, here are some ideas and questions that came up as I read your post:
- In the AltMBA, we work on a process for decision making where we lay out all of the options (e.g., "doing nothing" to "conquering the world" and everything in between, and the criteria you have to meet to be happy (or achieved). Very similar to what Carlos Saba suggested.
Then list out the criteria about the things you care about and grade each option against these things you care about.
Matthew Encina did something similar in this post, and it's really inspiring to see how to decide his next career path:
https://youtu.be/Inaw4g3mBw4?t=122
- And to pull on the core needs thread, if we zoom out, do you have a vision of where you see yourself in five years? Where would you like to be, what would you like to have accomplished? Where do you see the industry potentially heading, and what does it need to get there? What sucks? Are there things you could offer in there that also align with your achievement and happiness criteria?
- Are there things that light you up, want to research late in the night and tell your friends or community?
- What do you care about enough to build something about it and care for a long time?
Not sure these questions make sense, but I hope anything here helps. :)
Looking forward to your next chapter!
this is all super helpful
and tbh there's not a ton that really lights me up right now
the one thing I'm enjoying is writing here on the newsletter, and have already started working on some pieces that have been in my head for a long time, that I've never written down. So while the newsletter isn't likely to be the moneymaker, it's where I feel drawn to spending my time right now.
I feel in a similar boat ^
I really enjoyed this piece by Nat Eliason: https://blog.nateliason.com/p/four-great-decisions-per-year?utm_campaign=post&utm_medium=web
TLDR is you only need to make 4 (arguably less) great decisions a year. This means to take your time with it, and not make a decision just because you feel like you must do something and take action. Going for walks without headphones could be more “productive” than choosing something just to do something.
You probably know this well based on your decision to take time off and think/journal about several different paths. Wishing you the best of luck. ❤️