22 Comments

Some people are all in because they don't have much of a choice, like someone who recently got fired or laid off. However, you're right. If you have a relatively stable situation, it would be wise to ease into it and allow your full-time job fund your entrepreneurial venture.

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Absolutely, I think ‘all in’ is the right approach at times (sometimes to your point out of necessity) but not always, and not exclusively.

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This is smart advice! Thank you 🙏🏼

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Thanks Kristen, I wanted to share a different POV cause all I tend to hear is about how you need to go all in to do anything great, and it just ain’t true!

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Yes! There is such a strong push to either be all in, or nothing. I remember being told by an investor I admired that they only invest in companies who's founders were full-time. This often isn't possible, especially in today's economy. I wish I read this article a year ago, although sometimes I also think this is a realisation that only comes to light through a lived experience.

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Agree! I know this only through experience 😅😅

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Yeah it's a really interesting one. I certainly don't think all in is bad per se, but it's destructive to tell people that it's the only way, because it ultimately leads to so many people just not starting at all. I wish people who feel stuck knew that it's ok to take it bit by bit, step by step!!

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As someone who has always leapt, and never really thought about it being any other way, and is now discovering the value of building something slowly, over time, I also relate to this. <3

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It’s a different feeling easing in as opposed to going all in. Neither is better than the other and both can work, but these days I’m way more attracted to the slow incremental build than the frenetic meteoric rise too!

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I'm standing on the precipice of starting a portfolio career. I didn't quite know what to call it, so I owe you one for that - thanks.

After a long time at large corporates, I find myself mentally swinging back and forth - pulled between going after 'more of the same' jobs with titles and prestige and stepping fully into this new way of being.

I already know the former won't make me happy. I'm hoping a maintain the strength to push forwards into something that may be perfect for me rather than falling back into something I already know isn't.

Loved the series, glad I found it late so I could devour it all in one go. Thank you.

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I empathise heavily with where you are right now, it's a scary precipice to be standing on but if you've taken anything from the series I hope it's the knowledge that a portfolio career can be both financially lucrative and fulfilling (something that I wasn't sure was possible until I experienced it for myself). Stay strong and lead with your intuition, and you can't go wrong. So lovely to connect 😊

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Nice article Anna! I am working a 9-5 at the moment. It’s not something I hate, but I’m not excited all the time by the work I do.

I have started writing and publishing on Substack, I will see where it takes me. I definitely enjoy this much more, it feels more natural and aligned with my vision.

I will check out the other articles in the series! 🤓

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By writing online you’re absolutely on the path! 👏🏼

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Loved this and loved the voicenote!

Over the past year I’ve been taking small steps like creating a website, pitching my workshops, sharing my ideas online, which have all led to being hired for small pieces of work and making great connections.

It was all in preparation to take the leap, and my last day at my job is next Friday!

If I had gone straight into taking the leap, I don’t think I’d be where I am with the business today. Every decision would have been based on money, and in doing that I would have made some poor decisions.

By taking small steps I’ve been able to experiment, see what feels right and understand my clients.

It has been about building slower and building better.

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You hit the nail on the head, I think one of the trade offs of going all in is that you’re often solely making decisions based on money and your immediate survival, rather than focusing on what’s good in the long term. Congrats on making some big moves!! Excited for you ❤️

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That's exactly it. Thank you for your kind words!

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Loving this whole series. I left a full-time job 2+ years ago and have been creating a mix of incomes through various projects and styles of work but beating myself up for not defining 'what' I do. The portfolio career concept is giving me a nice framing to relax and understand how to work with it better. I also identify as an expert generalist and more so this setup feels super aligned for me. Your first article helped pull me out of an overwhelm spiral - thank you!!

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Yay! I’m happy this framing has helped you settle into (my words, not yours 😂) the multi passionate multi hyphenate identity, it certainly did the same for me too. I found it quite freeing when I recognised that just cause I’m doing lots of things, it doesn’t mean I’m not building something meaningful.

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I love this, It’s a podcast.

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Thank you 🙏🏽. As in the little voice note was like a podcast?

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Loved this and particularly liked the voicenote 🙏🏻🙏🏻🙏🏻

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Oh thank you Bonnie 💗

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