This is really good Maddie...over the past year, I have chosen to take on a lesser workload in my solopreneur business.
At times, I have struggled with calculating the amount of $ I am leaving on the table (especially when calculated over the course of a calendar year).
Other times, I am "okay" with leaving money on the table for the trade-off of less stress, an actual "day off" during the work week, etc.
My best friend asked if I will continue taking this lesser workload moving forward or not (he asked because he knows that I am focused on savings and increasing our household's investments / net worth)...it's a question that I think I know the answer to, but still wallow back and forth depending on the day (darn Type A brain) 😉
Thanks for sharing what this tension looks like in your life right now, Jordan. I always appreciate getting these insights into your story!
Every path we choose comes with a tradeoff...but as you know, the tradeoffs are rarely easy to make. One benefit of being a solopreneur, I hope, is that you have more flexibility in switching between paths, if/when you want or need to. 🤞
"Revisiting that map is important because the act of walking any path teaches us things we didn’t know at the outset." I agree, Maddie. The past is full of lessons for us, including our own past and pathway.
I'm enjoying the climb. I'm not sure I'm using a map, though. 🙂
Oh man, I revisit it "all" all the time! One important lesson I've learned is to pay attention to the little niggles that pop into your head (or heart) in the midst of each day - even when something is going well there are often tiny signs that it may not always be right or last forever. And that's exactly the info you need when it comes time to make a change...
This is such an excellent reminder, Amelia...I'm filing this lesson away. In the past, I've drowned out some of the smaller niggles with logic and reason. Seemed like a smart choice at the time—but of course they always come roaring back with a vengeance!
Every 7 years or so, I reassess:-) I didn't plan it that way. Just so happened. I'm in a pivot now with a ton more experience in what I want and don't want and a life fully lived. Cheers to your next season!
Thanks, Nneka—and cheers to *your* pivot, to living a full life, and to knowing what you do and don't want! If that's what the seven-year itch looks like, sign me up. 🤗
Gosh, it has been a while since I've revisited anything ha! I was in a way forced to when I had all these grand plans on a recent vacation and my husband/son didn't want to. It did give me time to reflect on how far I've come to even able to afford the money time off to be able to go somewhere for a week. It ended being such a refreshing trip and I'm reinvigorated.
I'm so happy you're feeling reinvigorated, Sarah! Even though you were forced to revisit your vacation plans (I've been there, ha), it sounds like you turned it into a beautiful opportunity for gratitude. I love it! 🥰
Oh, I love this question, Maddie. It reminded me of something I heard on a podcast once, where the host said he'd heard the question: "Am I still enjoying being [your name]?" Am I still enjoying being Cait Flanders, the author, etc.? Yep! If anything, I only want to be more of her. Thanks for helping to prompt that reflection—and for mentioning AIOO! That was fun to see ☺️
Oh, what a fabulous question...that's one to file away and return to, for sure.
I'm happy that you're still enjoying being Cait Flanders the author, because lots of us are, too (me obviously included!). But as you well know, it doesn't matter how many other people want you to stay on a given path if *you* don't want to walk it!
I think almost all your points apply to me and my career right now. I’m a teacher and I’m ready to leave. But there where to is proving the difficult part! I’m not a teacher who is paid all holidays, but I do get the summer off (unemployed but still off). I can’t imagine going back to non-school calendar job after over so long.
That’s it, although I should probably learn to the discomfort of the not knowing. One day I hope I’ll know and will move forward.
I like the way you worded it ‘allows you to embrace that quality of seasonality in your work’. I think it’s rephrasing like this will help me find that next step.
"I should probably lean into the discomfort of not knowing"—you and me both! That's the whole reason I started this newsletter 😅
I just finished reading Cal Newport's new book Slow Productivity. It has a whole section about working at a natural pace, so the idea of seasonality is top-of-mind lately!
It’s so uncomfortable though right!! I love that’s why you started the news letter. Perhaps I should write more about the discomfort in an attempt at leaning into it.
How are you getting on with the book, would you recommend it?
Gosh, I love this framing—reassessing the route. I could even see this commitment to doing so being helpful at the beginning of choosing a route in the first place.
I see a lot of clients in my practice have a hard time with indecision because making any decision at all can feel permanent. I’m often reminding clients that they can always make another decision down the road if the path no longer serves them. The language you use here is really clarifying and reassuring.
This means a lot coming from you, Kaitlyn—thank you! It's especially cool to hear your professional take as a psychotherapist.
I can totally relate to your clients, which is why I've intentionally adopted a spirit of experimentation as of late...it's definitely helped my decisions feel less permanent and high-stakes!
Yes totally! I love that. I do that a lot with new behaviors or habits I’m interested in trying. “This is an experiment or a theory. Let’s see what happens.” Rather than “This is what I’m gonna do and this will be the outcome.” Because lolzzzz it never goes that way anyway.
I reassess my route about 5 times a day. It's a constant struggle to stick to a path! I get discouraged very easily...but at least I know that I wouldn't enjoy a shadow career. I have a good internal BS detector.
What a lovely post, Maddie! Thoughtful as always. I’ve been watching a lot of curling lately and professional athletes, to me, have a fascinating decision process behind when to retire. Do you go out when you’re at the top of your game or wait until your body forces you to quit or somewhere in the middle?
Isn’t it fascinating how many people become financial planners when they what they crave is financial security? Yet it’s not the most lucrative career out there. In some ways, I feel like I got bored of spreadsheeting my own finances, so now I do that for others.
So often I feel like people just continue along in life without stopping to ask themselves “Do I want to be here now that I’m here?” Every day is a pivot and choice point in our lives. I’ve been getting better at that lately, more frequently pivoting and adjusting than I used to.
I’m so excited to see you flourishing now, building something for yourself instead of for someone else.
Jamie, this was such a lovely, heartfelt comment. Not surprising coming from you, but still. Thank you! ❤️
"Isn’t it fascinating how many people become financial planners when they what they crave is financial security?" Ooh, so this wasn't just me?! But that makes complete sense—folks in all kinds of "helping professions" wind up there after doing similar work for/on themselves first.
Having spoken with you about some of your own recent pivots, I'm not surprised to hear that you've gotten really good at checking in with yourself consistently. Three cheers for that! Can't wait to see all the cool places your clarity ends up taking you. 🚀
The part about getting stuck in a shadow career resonates! I've seen this many times with women I've mentored over the years. I just signed up for your Substack. Love it!
Phew—such a helpful reminder that I'm not alone in that experience! Fran, I'm so delighted to see your name here today. Thank you so much for reading *and* subscribing!
This conversation is smack in the middle of my awareness, Maddie—thanks so much for your writing on it! I have the great honor and pleasure of coaching people through major life decisions and transitions, and often (very!) have to remind myself to do the exact same work: taking stock of and appreciation for the road already travelled.
Looking forward to reading more of your beautiful wisdom and writing!
Bree, I'm so happy to make your acquaintance! 🤗 Your work is so important—it must feel like a huge honor to meet and support people at big, transitional moments in their lives. Please know that your kind words made my day!
Same, Maddie! And yes it is, and a huge responsibility too. What I love so much about this community is how we all seem to be here, writing and sharing, with similar goals in mind… helping our fellow humans in deep and sustainable ways. Thanks for the work YOU’re doing!
As always, Maddie, I find your wisdom resonant. I am finding myself needing to reassess my route more often lately than I have in the past. And that feels right.
Holly, thank you so much! I love hearing about how this idea lands for you in this chapter of your life. And I agree: there are times for pushing forward and times for reassessing—it's all seasonal. Something I'm sure you've encountered in your travels!
I'd love to hear from you! When’s the last time you stopped to reassess the route you’re traveling?
This is really good Maddie...over the past year, I have chosen to take on a lesser workload in my solopreneur business.
At times, I have struggled with calculating the amount of $ I am leaving on the table (especially when calculated over the course of a calendar year).
Other times, I am "okay" with leaving money on the table for the trade-off of less stress, an actual "day off" during the work week, etc.
My best friend asked if I will continue taking this lesser workload moving forward or not (he asked because he knows that I am focused on savings and increasing our household's investments / net worth)...it's a question that I think I know the answer to, but still wallow back and forth depending on the day (darn Type A brain) 😉
Thanks for sharing what this tension looks like in your life right now, Jordan. I always appreciate getting these insights into your story!
Every path we choose comes with a tradeoff...but as you know, the tradeoffs are rarely easy to make. One benefit of being a solopreneur, I hope, is that you have more flexibility in switching between paths, if/when you want or need to. 🤞
"Revisiting that map is important because the act of walking any path teaches us things we didn’t know at the outset." I agree, Maddie. The past is full of lessons for us, including our own past and pathway.
I'm enjoying the climb. I'm not sure I'm using a map, though. 🙂
Three cheers for the mapless adventure. It sounds delightful! 🤗
Oh man, I revisit it "all" all the time! One important lesson I've learned is to pay attention to the little niggles that pop into your head (or heart) in the midst of each day - even when something is going well there are often tiny signs that it may not always be right or last forever. And that's exactly the info you need when it comes time to make a change...
This is such an excellent reminder, Amelia...I'm filing this lesson away. In the past, I've drowned out some of the smaller niggles with logic and reason. Seemed like a smart choice at the time—but of course they always come roaring back with a vengeance!
Every 7 years or so, I reassess:-) I didn't plan it that way. Just so happened. I'm in a pivot now with a ton more experience in what I want and don't want and a life fully lived. Cheers to your next season!
Thanks, Nneka—and cheers to *your* pivot, to living a full life, and to knowing what you do and don't want! If that's what the seven-year itch looks like, sign me up. 🤗
Gosh, it has been a while since I've revisited anything ha! I was in a way forced to when I had all these grand plans on a recent vacation and my husband/son didn't want to. It did give me time to reflect on how far I've come to even able to afford the money time off to be able to go somewhere for a week. It ended being such a refreshing trip and I'm reinvigorated.
I'm so happy you're feeling reinvigorated, Sarah! Even though you were forced to revisit your vacation plans (I've been there, ha), it sounds like you turned it into a beautiful opportunity for gratitude. I love it! 🥰
Oh, I love this question, Maddie. It reminded me of something I heard on a podcast once, where the host said he'd heard the question: "Am I still enjoying being [your name]?" Am I still enjoying being Cait Flanders, the author, etc.? Yep! If anything, I only want to be more of her. Thanks for helping to prompt that reflection—and for mentioning AIOO! That was fun to see ☺️
Oh, what a fabulous question...that's one to file away and return to, for sure.
I'm happy that you're still enjoying being Cait Flanders the author, because lots of us are, too (me obviously included!). But as you well know, it doesn't matter how many other people want you to stay on a given path if *you* don't want to walk it!
It feels like such a simple but profound check-in question, to be asked at any moment in life (not just related to work)...
I think almost all your points apply to me and my career right now. I’m a teacher and I’m ready to leave. But there where to is proving the difficult part! I’m not a teacher who is paid all holidays, but I do get the summer off (unemployed but still off). I can’t imagine going back to non-school calendar job after over so long.
Such a good point, Sheila—sometimes it's easy to know you must leave the path you're on, but hard to identify the next right one.
I very much hope you're able to find a professional path that allows you to embrace that quality of seasonality in your work!
That’s it, although I should probably learn to the discomfort of the not knowing. One day I hope I’ll know and will move forward.
I like the way you worded it ‘allows you to embrace that quality of seasonality in your work’. I think it’s rephrasing like this will help me find that next step.
Thank you for your reply 💚
"I should probably lean into the discomfort of not knowing"—you and me both! That's the whole reason I started this newsletter 😅
I just finished reading Cal Newport's new book Slow Productivity. It has a whole section about working at a natural pace, so the idea of seasonality is top-of-mind lately!
It’s so uncomfortable though right!! I love that’s why you started the news letter. Perhaps I should write more about the discomfort in an attempt at leaning into it.
How are you getting on with the book, would you recommend it?
Yes, I'll cheer you on in that practice! Whether or not you write publicly, it's such a useful tool in times of uncertainty.
I absolutely churned through the book and would highly recommend it!
I’ve added the book to my want to read list and look forward to getting into it.
Let’s see what writing comes up with the guide of sitting in uncertainty 💚✍️
Gosh, I love this framing—reassessing the route. I could even see this commitment to doing so being helpful at the beginning of choosing a route in the first place.
I see a lot of clients in my practice have a hard time with indecision because making any decision at all can feel permanent. I’m often reminding clients that they can always make another decision down the road if the path no longer serves them. The language you use here is really clarifying and reassuring.
This means a lot coming from you, Kaitlyn—thank you! It's especially cool to hear your professional take as a psychotherapist.
I can totally relate to your clients, which is why I've intentionally adopted a spirit of experimentation as of late...it's definitely helped my decisions feel less permanent and high-stakes!
Yes totally! I love that. I do that a lot with new behaviors or habits I’m interested in trying. “This is an experiment or a theory. Let’s see what happens.” Rather than “This is what I’m gonna do and this will be the outcome.” Because lolzzzz it never goes that way anyway.
OMG it sure does not!! Only took me three and a half decades to figure that one out 😅
I reassess my route about 5 times a day. It's a constant struggle to stick to a path! I get discouraged very easily...but at least I know that I wouldn't enjoy a shadow career. I have a good internal BS detector.
Having a strong internal BS detector is the most important thing, I think. Almost everything else in life can be learned!
What a lovely post, Maddie! Thoughtful as always. I’ve been watching a lot of curling lately and professional athletes, to me, have a fascinating decision process behind when to retire. Do you go out when you’re at the top of your game or wait until your body forces you to quit or somewhere in the middle?
Isn’t it fascinating how many people become financial planners when they what they crave is financial security? Yet it’s not the most lucrative career out there. In some ways, I feel like I got bored of spreadsheeting my own finances, so now I do that for others.
So often I feel like people just continue along in life without stopping to ask themselves “Do I want to be here now that I’m here?” Every day is a pivot and choice point in our lives. I’ve been getting better at that lately, more frequently pivoting and adjusting than I used to.
I’m so excited to see you flourishing now, building something for yourself instead of for someone else.
Jamie, this was such a lovely, heartfelt comment. Not surprising coming from you, but still. Thank you! ❤️
"Isn’t it fascinating how many people become financial planners when they what they crave is financial security?" Ooh, so this wasn't just me?! But that makes complete sense—folks in all kinds of "helping professions" wind up there after doing similar work for/on themselves first.
Having spoken with you about some of your own recent pivots, I'm not surprised to hear that you've gotten really good at checking in with yourself consistently. Three cheers for that! Can't wait to see all the cool places your clarity ends up taking you. 🚀
The part about getting stuck in a shadow career resonates! I've seen this many times with women I've mentored over the years. I just signed up for your Substack. Love it!
Phew—such a helpful reminder that I'm not alone in that experience! Fran, I'm so delighted to see your name here today. Thank you so much for reading *and* subscribing!
LOL. I'm still on flat land. xo
It's the best place to sit back, crack open a cold beverage, and enjoy the view without breaking a sweat. Cheers to that! 😂
PS/forgot 👉🏻 that Steven Pressfield quote is SUCH a gem!!!
Ooh, I'm glad I'm not alone there—it's one of my favorites, too!
He’s sooo super awesome. A gem from a gem.
This conversation is smack in the middle of my awareness, Maddie—thanks so much for your writing on it! I have the great honor and pleasure of coaching people through major life decisions and transitions, and often (very!) have to remind myself to do the exact same work: taking stock of and appreciation for the road already travelled.
Looking forward to reading more of your beautiful wisdom and writing!
Bree, I'm so happy to make your acquaintance! 🤗 Your work is so important—it must feel like a huge honor to meet and support people at big, transitional moments in their lives. Please know that your kind words made my day!
Same, Maddie! And yes it is, and a huge responsibility too. What I love so much about this community is how we all seem to be here, writing and sharing, with similar goals in mind… helping our fellow humans in deep and sustainable ways. Thanks for the work YOU’re doing!
I feel the exact same way about everyone I've met here. We're so lucky to have this space to connect! ❤️
As always, Maddie, I find your wisdom resonant. I am finding myself needing to reassess my route more often lately than I have in the past. And that feels right.
Holly, thank you so much! I love hearing about how this idea lands for you in this chapter of your life. And I agree: there are times for pushing forward and times for reassessing—it's all seasonal. Something I'm sure you've encountered in your travels!