I say this every time but it is literally like you are in my head! In 2017 when I lost my passion for my corporate career, I remember standing in my kitchen and saying "I feel like I've climbed this ladder and turned around and realised I climbed the wrong one." It can be so destabilising and I felt lost for a long time. Finding people like yourself made me feel less alone on this wild ride of finding an intersection of career and meaning.
I renamed my newsletter to "Wandering the Grey" two years ago to explore this theme of forgoing an unconventional path after five years of engineering in Big Tech. The skepticism and the sneers you faced in your journey sound all too familiar. I created a little group with two other post-tech brave souls called "sabbadie hotline" where we share all the ups, the downs, the wins, the worries, but it's a very supportive group, and it helps having people who understand what you're going through. I wish you the best luck!
Anna, your journey resonates deeply with me. Society often pressures us to follow a linear, "safe" career path, and deviating from that can be met with skepticism and raised eyebrows. Your story is a testament to the courage it takes to step off that well-trodden path and forge your own. It's not just about embracing the "grey" but about painting it with the colors of your own values and aspirations. Thank you for reminding us that true fulfillment often lies in the undefined spaces where we get to create our own definitions of success.
independence, meaning, adventure, connection and financial security - are you my secret twin? I love reading your posts on how you established your portfolio career as I’m in the early stages of thinking about and designing my own. For now lots of experimenting next to my day job, but looking forward to one day be in the grey.
Twins! I love it. How are you currently experimenting on the side? I’m always curious about people’s pathways and what some of the big challenges are in the early days.
I’ve been hosting women’s circles for two years now, started my substack one year ago and I’m finishing up my embodiment coaching certification, starting to coach individual client this fall. I think my biggest struggle is gaining clarity around what it is that I’ll be offering and how this can possible tie together with my government career in the energy transition. There are snippets of ideas floating around in my head but I find it very hard to define for example my ideal client or a product I can sell. For now, I’m trying to take off the pressure to figure it all out by giving myself permission to start before I know what I’m doing. But it keeps nagging at the back of my mind..
This is such a common challenge that portfolio people face - how do you a) identify your unique value, b) package it up in a way that people understand and that you can sell, and c) find the thread that allows you to tie it all together into a clear story.
I’ll be writing a post on this in the next month or so, I might even turn it into a series given it’s the #1 struggle that people face.
Hi! I just found you yesterday. I went to your site (I think you have a couple?), your Insta..semi stalked...I even created an Are.na. I hadn't heard of it.
What is your core skill set. I've been doing this kind of portfolio thing in a caveman version for a while, but I'm starting to envision something different. I'm more producer than designer. Trying to figure out how that translates. Looking forward to more of your writing and your podcast thing. (I lived in Bryon Bay for a few years, so your accent kinda took me back).
Hey! Nice to connect with you here. Haha I am on most of the different platforms but Substack is by far my favourite.
I have a pretty broad skillset across Strategy, Operations, Brand, Marketing and Product but my sweet spot is working with startups launch and build in their first 1-5 years. I'm going to start writing a bit more about my consulting work cause I get this question a lot 😬
More fun. My value seems to more important than I was allowing. I’ve had a paycheck job once in life. In this new environment, I’m looking to learn it a bit and see if I can carve out something that makes me feel better. I’m redoing my one production studio and starting a nonprofit…and trying to fit in other interesting bits. Nice to meet you!
This is fantastic. I've listened to it twice! I left my prestigious tech job almost a year ago. I don't think independence is all that high on my list. I find constraints to be helpful and grounding. I love teaching (I teach part-time in a grad school program), running workshops, and collaborating with kind people. I'm working with my first consulting client now and learning a lot. Still figuring out the right mix for me :)
That's great! Finding the right mix takes time. I'm 5 and a half years into being self employed and I'm still on that journey, learning more about what I enjoy and what I don't as I test and experiment, and work with lots of different types of start ups and clients. It's fun!
I started working with an Executive Coach last year and one of the biggest takeaways from our time together has been learning my values. Prior to working with her I assumed values were something that didn't connect to my work. Wow was I wrong. I now look daily at how any decision I make regarding business and work align with my values. What a game changer it has been!
I also found it really interesting to do a values exercise and learn what truly matters to me- I expected something other than what my results were. In my mind I views values as things like 'honesty, integrity, family' and I was wildly surprised to learn what my true values were and how much I wasn't living in them. It was really helpful to hear you speak about your values and how you infuse them into your work, thank you Anna for showing up the way you do.
I’m a bit like you - up until about 3 years ago I hadn’t spent any time thinking about my values. I started doing this work when I was going through a really tough time personally, and they have been foundational for my decision making ever since.
My 19 year old daughter who is in her first year of uni, has just quit a very comfortable role in hospitality because she knows she’s stuck. I’d love to introduce her aligning her next role with her values. Can you please share the values exercise you undertook?
Please do write that post around money and how you structure/handle that, would love to read this! I'm always interested how other women who do their own thing in life structure and approach money.
Loved listening to your values and how you structure around these too. I've done something similar with the check-in around, 'will this take me closer to myself and what I'm wanting for myself right now, or further away?' and committing to only saying yes to the stuff that brings me closer. That's always led me well, but at times, it's been tough to say no to opportunities.
I remember when I was initially freelancing, I'd take jobs for the money because I needed to at the time. A few years in of doing this and building things up a bit, getting more experience etc., I remember having a moment of when a client came up that would have been good money but I wasn't a yes to it.
It wasn't that I didn't need the money at the time - I think I was covering my expenses but just barely, or close enough - it was more that with the extra security covering my expenses was giving me, I felt I had more space to feel into what was true for me, what felt good, and to make decisions based on this rather than, "Can I pay the bills this month and next month?" I'm still noticing some discomfort in me (uncertainty, maybe) around my having money and security as one of my values, yet alongside independence, it's become/is one of mine and is becoming more so now.
It’s so tough to say no to money and I absolutely took on clients and projects for cash in the early days of working for myself, even if I knew deep down they were distractions or taking me away from my values and where I was headed. But in the early days before you’re established in your business, sometimes you have to make decisions for short term survival vs. the long term vision. I’m grateful I’m no longer in that place and have the luxury to say no if something doesn’t align, but I definitely had to wade through the mud to get here!
I'm currently sitting in the uncertainty of grey. The noise of other voices and expectations are so hard to bat off when you're not secure in your choices yet yourself.
Turning to values is something that feels too simple when you've been doing the work for a while. But as they say, sometimes going back to basics is best.
I do believe in grounding yourself in the basics (values being one of them), but every person’s situation is different and perhaps it doesn’t resonate with everyone. The other thing that’s helped me develop conviction in my odd career choices is being really clear on my purpose and the impact I want to have in this lifetime. Do you have a sense of your own mission or why?
Funnily enough, I sat down and reminded myself of what my mission was last weekend. It can sometimes change along the way but I realised...it hasn't. It's simply to shine a light on another way to do life. That's not following society's 'shoulds'. To help others follow their unique curiosities and to pursue their own needs and fulfillment. This then really helped me decide my next steps ♥️ the how has changed a little but it aligns with my own needs and values better.
I say this every time but it is literally like you are in my head! In 2017 when I lost my passion for my corporate career, I remember standing in my kitchen and saying "I feel like I've climbed this ladder and turned around and realised I climbed the wrong one." It can be so destabilising and I felt lost for a long time. Finding people like yourself made me feel less alone on this wild ride of finding an intersection of career and meaning.
Haha. I think we were twins in a past life!
Yours isn't the only head she lives in! 😉😂
Haha, sorry team 😬
I renamed my newsletter to "Wandering the Grey" two years ago to explore this theme of forgoing an unconventional path after five years of engineering in Big Tech. The skepticism and the sneers you faced in your journey sound all too familiar. I created a little group with two other post-tech brave souls called "sabbadie hotline" where we share all the ups, the downs, the wins, the worries, but it's a very supportive group, and it helps having people who understand what you're going through. I wish you the best luck!
PS, I've written a lot about this stuff e.g.
1) Unshackling from golden handcuffs: https://www.tobiwrites.com/p/unshackling-myself-from-golden-handcuffs
2) How to design a sabbatical https://every.to/p/how-to-design-a-sabbatical
3) So you're a writer now?: https://www.tobiwrites.com/p/so-youre-a-writer-now
Love the idea of this hotline! How can I dial in? Hehe
haha we'd love to chat with you, i'll DM you here
Anna, your journey resonates deeply with me. Society often pressures us to follow a linear, "safe" career path, and deviating from that can be met with skepticism and raised eyebrows. Your story is a testament to the courage it takes to step off that well-trodden path and forge your own. It's not just about embracing the "grey" but about painting it with the colors of your own values and aspirations. Thank you for reminding us that true fulfillment often lies in the undefined spaces where we get to create our own definitions of success.
Absolutely, you get the metaphor! ❤️
independence, meaning, adventure, connection and financial security - are you my secret twin? I love reading your posts on how you established your portfolio career as I’m in the early stages of thinking about and designing my own. For now lots of experimenting next to my day job, but looking forward to one day be in the grey.
Twins! I love it. How are you currently experimenting on the side? I’m always curious about people’s pathways and what some of the big challenges are in the early days.
I’ve been hosting women’s circles for two years now, started my substack one year ago and I’m finishing up my embodiment coaching certification, starting to coach individual client this fall. I think my biggest struggle is gaining clarity around what it is that I’ll be offering and how this can possible tie together with my government career in the energy transition. There are snippets of ideas floating around in my head but I find it very hard to define for example my ideal client or a product I can sell. For now, I’m trying to take off the pressure to figure it all out by giving myself permission to start before I know what I’m doing. But it keeps nagging at the back of my mind..
This is such a common challenge that portfolio people face - how do you a) identify your unique value, b) package it up in a way that people understand and that you can sell, and c) find the thread that allows you to tie it all together into a clear story.
I’ll be writing a post on this in the next month or so, I might even turn it into a series given it’s the #1 struggle that people face.
Infomative
Hi! I just found you yesterday. I went to your site (I think you have a couple?), your Insta..semi stalked...I even created an Are.na. I hadn't heard of it.
What is your core skill set. I've been doing this kind of portfolio thing in a caveman version for a while, but I'm starting to envision something different. I'm more producer than designer. Trying to figure out how that translates. Looking forward to more of your writing and your podcast thing. (I lived in Bryon Bay for a few years, so your accent kinda took me back).
Hey! Nice to connect with you here. Haha I am on most of the different platforms but Substack is by far my favourite.
I have a pretty broad skillset across Strategy, Operations, Brand, Marketing and Product but my sweet spot is working with startups launch and build in their first 1-5 years. I'm going to start writing a bit more about my consulting work cause I get this question a lot 😬
What are you starting to envision for yourself?
More fun. My value seems to more important than I was allowing. I’ve had a paycheck job once in life. In this new environment, I’m looking to learn it a bit and see if I can carve out something that makes me feel better. I’m redoing my one production studio and starting a nonprofit…and trying to fit in other interesting bits. Nice to meet you!
This is fantastic. I've listened to it twice! I left my prestigious tech job almost a year ago. I don't think independence is all that high on my list. I find constraints to be helpful and grounding. I love teaching (I teach part-time in a grad school program), running workshops, and collaborating with kind people. I'm working with my first consulting client now and learning a lot. Still figuring out the right mix for me :)
That's great! Finding the right mix takes time. I'm 5 and a half years into being self employed and I'm still on that journey, learning more about what I enjoy and what I don't as I test and experiment, and work with lots of different types of start ups and clients. It's fun!
I started working with an Executive Coach last year and one of the biggest takeaways from our time together has been learning my values. Prior to working with her I assumed values were something that didn't connect to my work. Wow was I wrong. I now look daily at how any decision I make regarding business and work align with my values. What a game changer it has been!
I also found it really interesting to do a values exercise and learn what truly matters to me- I expected something other than what my results were. In my mind I views values as things like 'honesty, integrity, family' and I was wildly surprised to learn what my true values were and how much I wasn't living in them. It was really helpful to hear you speak about your values and how you infuse them into your work, thank you Anna for showing up the way you do.
I’m a bit like you - up until about 3 years ago I hadn’t spent any time thinking about my values. I started doing this work when I was going through a really tough time personally, and they have been foundational for my decision making ever since.
My 19 year old daughter who is in her first year of uni, has just quit a very comfortable role in hospitality because she knows she’s stuck. I’d love to introduce her aligning her next role with her values. Can you please share the values exercise you undertook?
It was so long ago but I’m fairly certain this is the one I did, from the great Brene Brown.
https://brenebrown.com/resources/living-into-our-values/
Please do write that post around money and how you structure/handle that, would love to read this! I'm always interested how other women who do their own thing in life structure and approach money.
Loved listening to your values and how you structure around these too. I've done something similar with the check-in around, 'will this take me closer to myself and what I'm wanting for myself right now, or further away?' and committing to only saying yes to the stuff that brings me closer. That's always led me well, but at times, it's been tough to say no to opportunities.
I remember when I was initially freelancing, I'd take jobs for the money because I needed to at the time. A few years in of doing this and building things up a bit, getting more experience etc., I remember having a moment of when a client came up that would have been good money but I wasn't a yes to it.
It wasn't that I didn't need the money at the time - I think I was covering my expenses but just barely, or close enough - it was more that with the extra security covering my expenses was giving me, I felt I had more space to feel into what was true for me, what felt good, and to make decisions based on this rather than, "Can I pay the bills this month and next month?" I'm still noticing some discomfort in me (uncertainty, maybe) around my having money and security as one of my values, yet alongside independence, it's become/is one of mine and is becoming more so now.
It’s so tough to say no to money and I absolutely took on clients and projects for cash in the early days of working for myself, even if I knew deep down they were distractions or taking me away from my values and where I was headed. But in the early days before you’re established in your business, sometimes you have to make decisions for short term survival vs. the long term vision. I’m grateful I’m no longer in that place and have the luxury to say no if something doesn’t align, but I definitely had to wade through the mud to get here!
I'm currently sitting in the uncertainty of grey. The noise of other voices and expectations are so hard to bat off when you're not secure in your choices yet yourself.
Turning to values is something that feels too simple when you've been doing the work for a while. But as they say, sometimes going back to basics is best.
I do believe in grounding yourself in the basics (values being one of them), but every person’s situation is different and perhaps it doesn’t resonate with everyone. The other thing that’s helped me develop conviction in my odd career choices is being really clear on my purpose and the impact I want to have in this lifetime. Do you have a sense of your own mission or why?
Funnily enough, I sat down and reminded myself of what my mission was last weekend. It can sometimes change along the way but I realised...it hasn't. It's simply to shine a light on another way to do life. That's not following society's 'shoulds'. To help others follow their unique curiosities and to pursue their own needs and fulfillment. This then really helped me decide my next steps ♥️ the how has changed a little but it aligns with my own needs and values better.
That's the real secret to success – being okay with not knowing all the answers.
💯