Anna, the below words are so true and should be freeing and inspiring for many because one thinks you have to have everything figured out, when really you just need to figure out that you want to start.
"Begin, even though it may be confusing or uncertain or unclear.
Begin, even if you have no clue.
Begin, even if no one in your life understands it.
Begin, even if you don’t understand it yet.
Begin without fear or knowledge of what comes next.
Anna, I'm just starting out a new career path. And it feels scary some times. Stories like yours are what that inspires me and keeps me rolling. Your ideas on structure are very useful and I'm going to try them for myself too. Thank you for this letter.
Thank you Shanjitha, fortunately I’m almost back to 100%! Congrats on taking the first step, it’s always the hardest 🩵. What new career path are you walking down?
I am talking about working in the medical communications niche which can be writing consumer health content, continuing education, website content, white papers too. I also have experience with research article writing but prefer the above more.
How lovely! I would love to get in touch with you - hit me up here ishita.singh@freyrsolutions.com with some writing samples/CV please. I might have something for you.
Anna, I really enjoy the candour and clarity of your writing. I’m looking forward to reading the remaining parts of this ‘portfolio career’ series.
So what stops me putting things in motion? I always have lots of ideas but then as I begin to research and look at other people doing similar things, I begin to pick holes in my own concepts. I seek the problems before I’ve really got started and effectively undermine myself.
Thanks Julia and you make a great point. I know that the message “just start!” can be reductive and sometimes really annoying to hear, because starting is bloody difficult and there’s always a reason (self doubt, lack of confidence etc.) that we don’t. I’ve been there, many times 🥲. I think it’s important to remember that any new idea can be ripped apart, and every new idea has holes in it. Even the ones that go on to completely change the world. The fact that your idea doesn’t seem “perfect” isn’t a signal that you shouldn’t pursue it. It’s actually a signal that you should give it a go, and see if you can stitch the holes back up.
Ahh I see, so perhaps I need to shift my perspective? Holes in new projects are all part of the process and resolving them, a positive step towards making the idea better.
I am sorry to hear you are sick. This sucks - especially while traveling!
And still you managed to get Part III out. I am eagerly following them all and try to apply them myself. I love how you structure your week, too! I also like bunching meetings together on one or two days. Well, there are a lot of changes going on in my life right now, so having a fix weekly schedule might not be purely in my hands, but it is something I am looking forward to build - at least around the writing aspects of my "portfolio career". And I think I need some better structure again once we are back from our next trip.
Thank you! Getting sick on holiday sucks but I’m almost back to normal, thank god 😂.
I think it’s important to note that figuring out what my ideal weekly structure looks like has taken about 12 months of experimenting. I first tried no meeting Wednesdays (which didn’t really work for me) and then when I realised no meeting Mondays were the best, it took a couple of months to completely clear my Monday schedules and set boundaries with clients that I wasn’t available to meet them. I guess my point is that it’s always a process and I’m still evolving and working towards mine too!
I totally get that and there will always be things coming in where you have to divert. But I like the general approach or attitude of taking control of what your ideal schedule / week looks like and then taking active decisions on where to divert from it 🙂
Do you think a “portfolio career” is obtainable by everyone? Or do you need to be at a certain place in your career (e.g. skills, reputations, experience, etc.).
I’m actually writing a post about this in a couple of weeks but my initial thoughts are that it’s achievable for anyone but for some people it may take some more time to work towards. Personally, I’ve benefited hugely from having 12+ years of working in business under my belt, and I think the experience I’ve had has been hugely valuable in helping set my portfolio career up this way. I definitely think experience helps, but in saying that, I also know some young guns who are operating in a similar way to me. More thoughts on this to come!!
All I can say is hella yes! Identifying who I now 'am' in the career space after leaving legal practice has been challenging - particularly as I pivoted 180 degrees. This Gen X'er was taught that I needed one solid career label. My heart didn't think so and wondered what a multi dimensional career could look like in the real world. Then I found Anna. My heart thanks you Anna for breaking this down into chewable chunks of doable.
Thanks for sharing Anna. I'm interested in building a portfolio career, and you've made the idea feel a little less intimidating. I’d love to know more about how you started landing regular freelance writing work. In particular, if there are any freelance groups/communities you joined, what publishers to approach and what they’re looking for?
Great question! When I started pitching to publications I really didn't have any leverage because I didn't yet have a Substack or any other published work, and so I had nothing to show for myself.
I started by identifying a couple of publications I wanted to write for in the business and lifestyle space. Then I connected with their editors on LinkedIn and Instagram, and found their email addresses online.
I then started pitching to their email addresses whenever I had an essay to share. In the body of the email I'd share:
- The title of the article
- The context (why I'm writing it, and why it's important now)
- The content (what's in the article)
- The conclusion (what's the reader going to take away from it? A new idea? A lesson?)
- Why it's relevant for their readership
I'd then attach the fully written article to the email. This was important to show the editors that I could write and had something valuable to say, because I couldn't direct them to my writing anywhere else. This was really important. As I started building relationships with editors I started pitching just ideas rather than fully written essays, and they'd pick them up if they liked them. I'd then write the essays.
I didn't join any groups or communities, and I'm not sure how valuable it would have been anyway. The most important thing for me was actually writing the pieces and consistently emailing them out to editors. It required quite a bit of work upfront cause I had to write my pieces before knowing if they'd get accepted, but it was really effective.
Hi Anna - I have another question on this one! If you're willing to share, interested to know what % of publications pay for contributed articles, and what the rate generally looks like?
I'm really enjoying this series Anna! I went self-employed almost three years ago and have also ended up with a portfolio career - not necessarily by design but because I have a mix of experience (content strategy and copywriting) and interests (creating a space for me - i.e. my Substack - and taking on clients).
I've gone down different paths during the past few years. Some things worked, some things didn't, some things massively exceeded my expectations. Trying, pivoting and moving with what feels good has helped shape what I do day-to-day and I can imagine it will only continue to evolve as I do. That's what I love about working for myself. I'm not in a box, and that feels so freeing.
Taking on projects I'm not particularly interested in doesn't work for me - even if they pay well. I've taken on a few things in the past that didn't inspire/compel me and they always felt like a chore, even if the monetary reward was there. It's tricky to make the decision sometimes (especially in this economy) but my priority now is only saying yes to projects and clients that feel good in my gut. That's when I enjoy my work most, and produce my best stuff!
That’s a great insight. I definitely took on projects that weren’t the best fit in the beginning to get some momentum, but I’m similar to you in that these days, I’m much more discerning.
This is what I needed to read this week. I've been stuck in that rut you describe as a generalist who's not sure what to do. I'm lucky I have a full time job, but I feel like my mental energy is so low when it comes to my portfolio career activities. Your advice about just getting going, putting in some reps whether it's writing or meeting people etc, is great.
Sorry it's taken me a while to come back to your comment Joseph, I've been travelling and just got home.
The rut is real, isn't it?! I struggled in the beginning with how to position myself as a generalist, but the more clients I've worked with and the more mentoring and advising I've done, the more I've come to recognise it as a strength, not a weakness.
I'm also a massive believer in doing the smallest possible thing in pursuit of a larger goal, even if you don't know what that goal is yet. All you need to do is to get the ball rolling! Daily writing or sending one cold email/DM per day is how I started, but I'd do whatever feels natural for you.
Loving your series Anna! I’m on a similar journey at the moment and I’m at the very beginning of it. As scared as I am, I’m also trying to savour the excitement, nervousness and exhilarating moments of clarity as I optimise for execution. 🤙
Anna, the below words are so true and should be freeing and inspiring for many because one thinks you have to have everything figured out, when really you just need to figure out that you want to start.
"Begin, even though it may be confusing or uncertain or unclear.
Begin, even if you have no clue.
Begin, even if no one in your life understands it.
Begin, even if you don’t understand it yet.
Begin without fear or knowledge of what comes next.
Just begin."
Thank you 🤍. It’s the greatest misconception of all time, that everything needs to be figured out before you start. The complete opposite is true!!
Anna, I'm just starting out a new career path. And it feels scary some times. Stories like yours are what that inspires me and keeps me rolling. Your ideas on structure are very useful and I'm going to try them for myself too. Thank you for this letter.
And I'm sorry that you are sick. Get well soon.
Thank you Shanjitha, fortunately I’m almost back to 100%! Congrats on taking the first step, it’s always the hardest 🩵. What new career path are you walking down?
I'm looking for medical writing opportunities.
Hey @shanjitha, can you shed some more light on Medical writing opportunities? Are we talking research papers / white papers or something else?
I am talking about working in the medical communications niche which can be writing consumer health content, continuing education, website content, white papers too. I also have experience with research article writing but prefer the above more.
How lovely! I would love to get in touch with you - hit me up here ishita.singh@freyrsolutions.com with some writing samples/CV please. I might have something for you.
Sure, Ishita. I’ll get back to you.
Anna, I really enjoy the candour and clarity of your writing. I’m looking forward to reading the remaining parts of this ‘portfolio career’ series.
So what stops me putting things in motion? I always have lots of ideas but then as I begin to research and look at other people doing similar things, I begin to pick holes in my own concepts. I seek the problems before I’ve really got started and effectively undermine myself.
Thanks Julia and you make a great point. I know that the message “just start!” can be reductive and sometimes really annoying to hear, because starting is bloody difficult and there’s always a reason (self doubt, lack of confidence etc.) that we don’t. I’ve been there, many times 🥲. I think it’s important to remember that any new idea can be ripped apart, and every new idea has holes in it. Even the ones that go on to completely change the world. The fact that your idea doesn’t seem “perfect” isn’t a signal that you shouldn’t pursue it. It’s actually a signal that you should give it a go, and see if you can stitch the holes back up.
Ahh I see, so perhaps I need to shift my perspective? Holes in new projects are all part of the process and resolving them, a positive step towards making the idea better.
That’s my personal belief ❣️
I am sorry to hear you are sick. This sucks - especially while traveling!
And still you managed to get Part III out. I am eagerly following them all and try to apply them myself. I love how you structure your week, too! I also like bunching meetings together on one or two days. Well, there are a lot of changes going on in my life right now, so having a fix weekly schedule might not be purely in my hands, but it is something I am looking forward to build - at least around the writing aspects of my "portfolio career". And I think I need some better structure again once we are back from our next trip.
Thank you! Getting sick on holiday sucks but I’m almost back to normal, thank god 😂.
I think it’s important to note that figuring out what my ideal weekly structure looks like has taken about 12 months of experimenting. I first tried no meeting Wednesdays (which didn’t really work for me) and then when I realised no meeting Mondays were the best, it took a couple of months to completely clear my Monday schedules and set boundaries with clients that I wasn’t available to meet them. I guess my point is that it’s always a process and I’m still evolving and working towards mine too!
I totally get that and there will always be things coming in where you have to divert. But I like the general approach or attitude of taking control of what your ideal schedule / week looks like and then taking active decisions on where to divert from it 🙂
Do you think a “portfolio career” is obtainable by everyone? Or do you need to be at a certain place in your career (e.g. skills, reputations, experience, etc.).
I’m actually writing a post about this in a couple of weeks but my initial thoughts are that it’s achievable for anyone but for some people it may take some more time to work towards. Personally, I’ve benefited hugely from having 12+ years of working in business under my belt, and I think the experience I’ve had has been hugely valuable in helping set my portfolio career up this way. I definitely think experience helps, but in saying that, I also know some young guns who are operating in a similar way to me. More thoughts on this to come!!
Thanks, looking forward to it.
All I can say is hella yes! Identifying who I now 'am' in the career space after leaving legal practice has been challenging - particularly as I pivoted 180 degrees. This Gen X'er was taught that I needed one solid career label. My heart didn't think so and wondered what a multi dimensional career could look like in the real world. Then I found Anna. My heart thanks you Anna for breaking this down into chewable chunks of doable.
This note made me smile and tear up a little at the same time. I’m so happy this has resonated so deeply for you ❤️
Thanks for sharing Anna. I'm interested in building a portfolio career, and you've made the idea feel a little less intimidating. I’d love to know more about how you started landing regular freelance writing work. In particular, if there are any freelance groups/communities you joined, what publishers to approach and what they’re looking for?
Hey Emma,
Great question! When I started pitching to publications I really didn't have any leverage because I didn't yet have a Substack or any other published work, and so I had nothing to show for myself.
I started by identifying a couple of publications I wanted to write for in the business and lifestyle space. Then I connected with their editors on LinkedIn and Instagram, and found their email addresses online.
I then started pitching to their email addresses whenever I had an essay to share. In the body of the email I'd share:
- The title of the article
- The context (why I'm writing it, and why it's important now)
- The content (what's in the article)
- The conclusion (what's the reader going to take away from it? A new idea? A lesson?)
- Why it's relevant for their readership
I'd then attach the fully written article to the email. This was important to show the editors that I could write and had something valuable to say, because I couldn't direct them to my writing anywhere else. This was really important. As I started building relationships with editors I started pitching just ideas rather than fully written essays, and they'd pick them up if they liked them. I'd then write the essays.
I didn't join any groups or communities, and I'm not sure how valuable it would have been anyway. The most important thing for me was actually writing the pieces and consistently emailing them out to editors. It required quite a bit of work upfront cause I had to write my pieces before knowing if they'd get accepted, but it was really effective.
I hope this helps 😊
I hope this helps!
Hi Anna - I have another question on this one! If you're willing to share, interested to know what % of publications pay for contributed articles, and what the rate generally looks like?
Hey Emma, happy to share some more info in the DMs if you like!
Super helpful, thanks Anna!
I'm really enjoying this series Anna! I went self-employed almost three years ago and have also ended up with a portfolio career - not necessarily by design but because I have a mix of experience (content strategy and copywriting) and interests (creating a space for me - i.e. my Substack - and taking on clients).
I've gone down different paths during the past few years. Some things worked, some things didn't, some things massively exceeded my expectations. Trying, pivoting and moving with what feels good has helped shape what I do day-to-day and I can imagine it will only continue to evolve as I do. That's what I love about working for myself. I'm not in a box, and that feels so freeing.
Isn't it so freeing! I'm curious - what things have worked well for you? And what totally sucked?
Taking on projects I'm not particularly interested in doesn't work for me - even if they pay well. I've taken on a few things in the past that didn't inspire/compel me and they always felt like a chore, even if the monetary reward was there. It's tricky to make the decision sometimes (especially in this economy) but my priority now is only saying yes to projects and clients that feel good in my gut. That's when I enjoy my work most, and produce my best stuff!
That’s a great insight. I definitely took on projects that weren’t the best fit in the beginning to get some momentum, but I’m similar to you in that these days, I’m much more discerning.
This is what I needed to read this week. I've been stuck in that rut you describe as a generalist who's not sure what to do. I'm lucky I have a full time job, but I feel like my mental energy is so low when it comes to my portfolio career activities. Your advice about just getting going, putting in some reps whether it's writing or meeting people etc, is great.
Sorry it's taken me a while to come back to your comment Joseph, I've been travelling and just got home.
The rut is real, isn't it?! I struggled in the beginning with how to position myself as a generalist, but the more clients I've worked with and the more mentoring and advising I've done, the more I've come to recognise it as a strength, not a weakness.
I'm also a massive believer in doing the smallest possible thing in pursuit of a larger goal, even if you don't know what that goal is yet. All you need to do is to get the ball rolling! Daily writing or sending one cold email/DM per day is how I started, but I'd do whatever feels natural for you.
So happy to connect 😊
Thank you for writing this.
It will help me shape my approach to the next stage of my career.
I look forward to your next piece :)
So glad it’s helping bring some clarity and direction! Mission accomplished 🥰
Such great info balanced with a lot of comfort for us freelancers in similar positions 💌
Thanks Katie, you’re certainly not alone ❣️
Loving your series Anna! I’m on a similar journey at the moment and I’m at the very beginning of it. As scared as I am, I’m also trying to savour the excitement, nervousness and exhilarating moments of clarity as I optimise for execution. 🤙
Thanks Ishita! Feeling scared is totally normal when you’re starting to build and create something new. It’s all part of it!
Loving this series so much, Anna, as I, too, am a generalist in pursuit of the “portfolio career”! ☺️
Glad you’re on the mend!