43 Comments

I am so grateful I found you and your words. I love everything you are doing and since being tagged in your substack I have gone down the Anna rabbit hole and want more! Let's be try-hards together because like you, I think there is a way have an 'unconventional' career that gives us meaning and lights our souls on fire!

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Maybe we can start a girl group called the 'try-hards' and invite all our try-hard friends, and then collectively try so hard we overthrow the system and take over the world.

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So inspiring, thanks for sharing Anna. Got goosebumps listening to that last line, loved the audio! I didn't think about doing this but will try recording myself in the future, it's a nice touch. Fun fact, I used to work on Curb Your Enthusiasm as a sound editor back in the day. This hit home.

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You worked on Curb!? Oh my gosh I bet you have some stories. Major jealousy, it's one of my favourite shows 😂. So grateful that you listened the audio and got the goosebumps!

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It’s one of the funniest shows ever 💯

Stories for days.. good times indeed. Look forward to following your journey here.

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Cannot tell you enough how much your words read like my thoughts these days. Think how crazy we’re going to drive everyone with our non-niche niche portfolio careers - they truly won’t know what to do with all of us 😉

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I'm more than comfortable driving everyone crazy if it means we're spreading good ideas and living lives on our own terms. Go us!

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💯💯💯

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Short and sharp!

Anna, that was lovely. I've found that when these human errors we call fears, like "other people's judgements", come nagging, I look at a quick video zooming out from a street view to a galaxy view and the fear dissolves like the sugar in my coffee.

Keep up keeping up.

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Totally! I posted this the other day on LinkedIn and it's something I try and remind myself of when I get stuck in the weeds:

If you ever feel like you’re not making progress fast enough, remember that you’re a set of temporarily organised atoms in an infinite universe that will soon be split apart in the literal blink of a cosmic eye.

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I chuckled at how you answer the “what do you do?” question, as I find myself doing the same mental gymnastics and fumbling over it. Really digging the “portfolio career” concept, and love the audio note you included. Feeling inspired to state my own mission, own it, and really go after it 🙌

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"What do you do?" is the trickiest question to answer, after "how are you, really?" haha. I heard someone explain themselves as a 'creative multi hyphenate entrepreneur' the other day and I kinda liked it, although it's a mouthful to say.

So happy to hear this inspired you to work on your own mission and go after it! All power to you.

And thanks for your feedback on the audio, I'm still playing around with it and trying to gauge whether people find it valuable.

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I really do enjoy the audio. I probably wouldn’t have read it if it weren’t for the audio, actually, as I had my hands full at the moment but was able to listen in. Plus, it’s fun hearing your voice, as if you’re talking directly to me. So, it’s both convenient and makes it more engaging

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Great post, Anna✌️

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Thanks Tim, appreciate your support as always ❤️

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Reclaiming the word try-hard is going to be one of those things that sticks in my mind for a very, very long time. Paradigm shifting.

Try hard? Damn right I am. Wouldn't want to be anything else

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Welcome to the club ✌🏼

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The “what do you do for work?” question has been the most confronting for me. I tend to make myself small and adjust the answer depending on the person - what they’d understand or see more value in. To some I say I do business consulting, to others I say I work on some local projects. Do you feel like you’ve reached a point where you would answer with describing a portfolio career?

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Yeah it's a hard one isn't it? I don't think I'm clearly able to articulate all the things I do yet. One word that seems to encompass it is 'builder', as in I help founders build startups, individuals build fulfilling lives, and I'm also building my own thing around this newsletter. Another phrase I'm playing with is "creative, multi-hyphenate entrepreneur" but it's kinda a mouthful. I'm confident that how I communicate what I do will evolve over time as I become clearer, as I'm sure it will for you too :)

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thanks for the thoughtful reply! Helpful to hear your examples and experience. Thank you for all you have shared!

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Excellent post ❤️

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Thank you 🙏🏽

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Yes please! I am such a Labrador energy person. I have to remind myself not to jump sometimes. This is lovely reassurance that it is okay to be enthusiastic

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I think being enthusiastic is an amazing quality! It only can become dangerous when it’s overplayed, and you become so enthusiastic and drawn to shiny objects that you never get anything done 💆🏻‍♀️

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Something I’ve learned - the hard way - now I’m training myself to stay on guard rails, habits and routines that serve me but I bring along my joy - why not?

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Brilliant post, Anna! I very much relate.

Have you found Brad Montague on here yet, and his Substack, The Enthusiast? One of my favs. I think you might enjoy his writing too.

And another thumbs up for the audio. I notice I always look for your audio at the end now, after I listened the first time and really enjoyed it.

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I haven't!! He looks great, I can't wait to dive into his Substack. Thanks for the rec! And thanks for the audio feedback too, it's incredibly encouraging ❤️

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❤️🙂

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I feel like the best solution to the “what do you do?” question is to not care about it at all. Give up trying to impress people.

If I don’t want to get into detail with the person, I’ll just say “consultant” and hope it ends there.

If they seem interesting, I’ll tell them the full story, even starting with “well, it’s complicated…”

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For me it's not about impressing anyone, it's more about my ability to clearly articulate the value that I offer.

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Why would you need to articulate the value you offer at a social setting?

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I’m loving this for you! Sometimes the whole fake-it-til-you-make-it mindset works. It feels like you’re teetering between authenticity and impostor syndrome, but over time you start to claim who you are and can truly believe it! It took me over a year to get comfortable calling myself an “artist”, but once I started telling people that’s what I do, it became easier. More power to you and excited to see where things take you!

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Thank you ❤️. I've always been solidly in the identity of a founder or operator, so it's nice to start to acknowledging the more creative side that sits alongside my business-brain. Exciting times for both of us, it seems!

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Really like your writing Anna.

This was motivating and this line/s is great.

"I try not to be a try-hard, all while trying very hard because I refuse to let the fear of other people’s judgements win. Wondering ‘what if’ for eternity is a price I’m not willing to pay.

So here I am. A try-hard."

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Thank you so much, that means a lot 🥹

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THIS! This really hit me where I'm at these days (a freelance consultant / writer / etc after running a creative agency). Thank you for once again putting my subconscious feelings into words. :)

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It's so easy to default back to playing small but I am hereby declaring with this post not to do it anymore! (And neither should you 💗)

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Just redid my LinkedIn this afternoon and definitely felt like it looks and reads awk. Come on LinkedIn, catch up to the mutihyphenate future!

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Can someone please submit a ticket to the LinkedIn design team and tell them they need to update their UX to align with the future of work? Kthxbai

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