70 Comments
User's avatar
Edina Kalamperovic's avatar

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."

Expand full comment
Anna Mackenzie's avatar

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!!

Expand full comment
Shanjitha's avatar

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.

Expand full comment
Anna Mackenzie's avatar

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?

Expand full comment
Shanjitha's avatar

I'm looking for medical writing opportunities.

Expand full comment
Ishita Singh's avatar

Hey @shanjitha, can you shed some more light on Medical writing opportunities? Are we talking research papers / white papers or something else?

Expand full comment
Shanjitha's avatar

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.

Expand full comment
Ishita Singh's avatar

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.

Expand full comment
Shanjitha's avatar

Sure, Ishita. I’ll get back to you.

Expand full comment
Julia Jarvis's avatar

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.

Expand full comment
Anna Mackenzie's avatar

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.

Expand full comment
Julia Jarvis's avatar

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.

Expand full comment
Anna Mackenzie's avatar

That’s my personal belief ❣️

Expand full comment
Fabienne Mannherz's avatar

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.

Expand full comment
Anna Mackenzie's avatar

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!

Expand full comment
Fabienne Mannherz's avatar

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 🙂

Expand full comment
Rick Foerster's avatar

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.).

Expand full comment
Anna Mackenzie's avatar

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!!

Expand full comment
Rick Foerster's avatar

Thanks, looking forward to it.

Expand full comment
Virginia Robin's avatar

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.

Expand full comment
Anna Mackenzie's avatar

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 ❤️

Expand full comment
Goran Vinko's avatar

Right. I manage multiple social media channels, where I post my works. I started posting on Substack today! So, I don't know where all this effort will lead. But I know this will (soon) open up great opportunities in self employment (dreams). I can so much relate to your article. Because it's encouraging and inspiring.

Expand full comment
🎈Noemi Apetri 🎈's avatar

Love the hat!

Expand full comment
Anna Mackenzie's avatar

Hehe thanks!

Expand full comment
Tylney Taylor's avatar

💯 - this has been my mantra for decades now. Thank you for your boldness!

Whatever you do, or dream you can, begin it.

Boldness has genius, power, and magic in it.

Begin It Now.

Expand full comment
rei (*ᴗ͈ˬᴗ͈)ꕤ*.゚'s avatar

Thank you so much for this, Anna! I'm making a huge career shift and your story is what I need to continue being a multi-passionate. Seriously, thanks for mapping out a portfolio career guide for free! It's helping me a lot! 🙏🏻

Expand full comment
Anna Mackenzie's avatar

You're so welcome!! I'm happy you found me 🫶🏼

Expand full comment
Jen Blair's avatar

I’m so glad this post showed up in my feed. I just left a startup that I didn’t found but grew from the ground up, and relate hard to the “generalist as blessing or curse” and the love of systems balanced with creative work. I’m at a crossroads where I want to leave traditional work and do exactly what you’re doing and it’s terrifying. I’m excited to dive into all the posts you linked! Thank you for sharing, and thank the algorithm gods for sending this to me ☺️

Expand full comment
Anna Mackenzie's avatar

Hey Jen,

I feel you, I was exactly where you are about 2 years ago. I know it's terrifying but trust me, it's glorious on the other side. Here to support if you ever need ❤️

Expand full comment
Jen Blair's avatar

Appreciate that so much! ❤️

Expand full comment
Dana Textoris's avatar

This post is exactly what I needed — especially the reassurance that it’s fine not to have it all figured out in the beginning. Your tips here are gold. Thank you for this gift!

Expand full comment
Anna Mackenzie's avatar

You’re so welcome. If it feels messy, you’re doing it right x

Expand full comment
Dana Textoris's avatar

I wrote the last part of this down in my journal to really get it in my body!

Expand full comment
Castaly Haddon's avatar

This is soooo helpful. Thanks.

Expand full comment
Anna Mackenzie's avatar

Pleasure!

Expand full comment
Jane McCarthy's avatar

I love what you are saying about getting runs on the board. A really good reminder to do things, even if they don't fit perfectly - as a way to build energy and momentum.

Expand full comment
Anna Mackenzie's avatar

Absolutely! In the beginning momentum is the only thing that matters.

Expand full comment
Andjelka Jankovic's avatar

" I put my ideas out into the world and the world began talking back." Gorgeous sentence!

This reminds me of my first Substack letter, which came to me as "Beginnings are hard"

Expand full comment
Anna Mackenzie's avatar

🥹 thank you

Expand full comment
Jess Barker's avatar

This was such an encouraging read. Thank you for sharing your experiences!

Logistical question about connecting the dots between #1 to #2 - How did you go about networking without having a clear pitch or offering? I've had the occasional convo with people where it's like, "i can do this or this or this for you, or whatever you need help with" but without specificity it can fall flat. They might be kind and happy to "think on it" but no opps ever arise from that. So how did you get from that "idk what exactly I'm doing" state to securing real opportunities?

🙏 thanks!

Expand full comment
Anna Mackenzie's avatar

Such a good question! I’m actually in the throes of writing a post about this because it’s come up so many times in conversations. How do you actually pitch yourself and your skills, when you can do (or are doing) a million things? It’s a particularly relevant question for the generalists out there, and I have thoughts!!

Tomorrow’s post will answer this at a high level but I’m planning another post that goes into it more deeply. Stay tuned :)

Expand full comment
Jess Barker's avatar

Oh that's brilliant!! Really looking forward to hearing your POV on how to make it work ☺️

I know I tend to avoid the massive awkwardness of not knowing what to do or say, but sometimes I really would like to get out there more and find connections, and meaningful or (at least interesting) opportunities. So your upcoming posts will no doubt make a huge difference to a lot of us out here! 🙏💗

Expand full comment