Aug Recap: Wild Imaginings of Second Chapter Careers


My monthly newsletter sent at the end of every month, to stay connected and inspire reflection for creating meaningful work and a purpose-driven business.

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Hi Reader,

August in Bali is our "winter" in the tropics, which means I've actually been able to spend a lot of days outdoors without melting into a pool of sweat. I've been spending a lot of time hiking and having walking dates with friends to soak up the cool days and breezy weather.

This month's highlight was a little picnic gathering I hosted with a cozy group of friends. I called it "Wild Imaginings of Second Chapter Careers" (very on brand, I know ๐Ÿ˜„).

A few of my friends are going through their own version of a work transition right now, and I thought it would be fun to explore together how our skills, wisdom, and experiences could be used for imagining new ideas for projects, careers, and hobbies if we weren't pigeonholed into what's on our resumes.

I myself have been secretly fantasizing about fun projects I would love to create that may have nothing to do with my business.

It's a great exercise to flex our creative muscle and expand our thinking on passions and interests that can sometimes sit on the back-burner. And also way more fun to do this with others!

Here's how it worked. Everyone filled out four columns of questions.

  1. Skills you've been paid for or known for
  2. Things you geek out on, hobbies, rabbit holes you go into
  3. Lived experiences you've overcome, "hard knocks" wisdom
  4. Ideas that's been on the secret back-burner but haven't acted on because you don't think you're capable/ready enough

Then, one by one, we'd focus a 10-minute "wisdom circle" on one person. That person would turn their back to the group so we could free flow "gossip" about them behind their back (lovingly, obviously). It went something like this:

  • What we see in your reflections that you're not seeing (the combinations, the through-line, the skill that's actually rare, the thing you dismissed that we all lit up at)
  • Where we hear the limiting belief doing the work (you said "I could never charge for that" - we noticed that, and here's what we see instead)

It was so fun...and revealing.

With your back turned, people talk about you more honestly. They start connecting dots you can't see yourself. They notice themes in your life story and your interests that you've never linked together. And they name your gifts out loud in a way that makes your "crazy ideas" feel a whole lot more grounded and realistic.

That collective courage is so important when we're rethinking our body of work. Sometimes we need other people to believe in the new direction before we're brave enough to move toward it ourselves.

I even got to have a turn at it. Having people look at my wild ideas and passions that aren't directly related to the current business I have was kind of awesome.

Here's a few of the ideas the group wouldn't let me dismiss. They took my brainstorm, linked it back to my life story, and started mapping out how each one could actually become something real:

๐Ÿ’˜ A "Hinge" app but for finding forever friends. For people who are building chosen family because their family of origin didn't meet their needs, or because they're childfree, living abroad, or just in a season of life where the old friendships don't fit anymore.
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๐Ÿฅพ Walking pilgrimages for people exploring who they are beyond the identity they inherited from their family, culture, or place of birth.
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โ€‹ ๐Ÿ‘จโ€๐Ÿ‘ฉโ€๐Ÿ‘งโ€๐Ÿ‘ฆ A "rent a family member" matching service. For people who didn't grow up with the family members they needed, and want to experience those relationships with people who aren't bloodline.
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โ€‹ ๐Ÿ An "Amazing Race" style adventure retreat, but for identity discovery. Getting to know yourself through play and adventure instead of another yoga-and-journal setup.
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โ€‹ ๐Ÿก Co-living and retiring-together communities for people growing old with their chosen family, with shared ownership of land and homes.

Oh, and someone said I should write a book about how to find love when you live abroad. I've spent over a decade living abroad and somehow figured out how to find partners who want this kind of untraditional life too, and apparently that's a skill worth sharing ๐Ÿคท๐Ÿปโ€โ™€๏ธ.

You can see the themes, right?!

I got so excited seeing other people get excited about how these could become real initiatives that link to stuff I care about way beyond my business. If any of those ideas sparked something for you too, I'd love to hear it. Let me know which wild idea matched something you've been thinking about too.

Speaking of transitions, making personalized playlists is basically my love language (I used to burn CDs for friends, if that dates me appropriately!), so I made a "Transitions" playlist for one of the friends who attended. It felt right for the season we're all in. I'm sharing it here in case you want something good in your ears:

๐ŸŽต Listen to the Transitions Playlist on Spotify:

artist
โœจ Transitions โ€ข Lyds
Follow The Sun โ€ข Xavier Rudd
PREVIEW
Spotify Logo
 
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I hope you had a beautiful month,

-Lydia
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โ€‹๐ŸŒฟ Work With Me

That "Wild Imaginings of Second Chapter Careers" gathering I hosted with my friends reminded me of something I see with my clients a lot too. We can be so deep inside our own business that we can't tell the difference between "Do I need better marketing?" and "I actually don't want to do this anymore."

The reason things feel off in your business isn't just your positioning, your systems, or your marketing. It's that you've already evolved. You're a different person than the one who built this thing. Your work just hasn't caught up yet.

No tactic fixes work you've outgrown. It starts the moment you're honest about who you've already become, and rebuild around that person.

If you've been running your business for a few years and something has stopped feeling right, I'd love to talk. A clarity call is free, and we'll get honest together about what's still yours and what you've outgrown.


โญ On Building A Life & Business You Love
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Inspiring content you might've missed

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๐Ÿงฉ How to Simplify Your Business Without Starting Over

You don't have to burn everything down to make your business feel like yours again. This one walks through how to simplify without losing what's working.

โ†’ Simplify without starting from scratchโ€‹

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๐Ÿชž 2 Signs You've Outgrown Your Business

How to tell when the problem isn't your marketing or your systems. Two signs that it might be the business itself you've outgrown.

โ†’ Spot the signs before you burn outโ€‹
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๐Ÿ”’ When You've Built a Profitable Prison

What happens when you've outgrown parts of your body of work but not the whole thing? When the offer that made you your name isn't the offer you want to keep doing?

โ†’ Listen to the episodeโ€‹

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๐Ÿ’ญ Is Meaningful Work a Luxury?

The belief that you can't afford to do meaningful work because you have to keep paying the bills. What's underneath that? Maira and I unpack the fear that if you showed up doing the work you actually care about, people wouldn't pay for it.

โ†’ Listen hereโ€‹

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โ€‹๐ŸŽ™๏ธ I was also a guest on two great podcasts this month:
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I joined the Nomad CEO Podcast to talk about building a business that supports your life instead of consuming it, and jammed with Jeremy Yang on the Marketing for SMEs Podcast to talk about what happens when established business owners have outgrown the way their business operates.


๐Ÿ’ก Ideas Sparkerโ€‹
โ€‹Curated resources to spark inspiration and conversation

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I'm Reading...

  • โ€‹The Joy Formula by Mary Schiller - Mary is one of my original coaching clients from years ago when we worked together on her career transition. After, she moved to Paris from the US to reinvent her work and her life, and I just love how much wisdom she's poured into this book.
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  • โ€‹Will It Blend? by Pam Slim - Love this gem from Pam about using tiny blending experiments to test your big visions before committing to them. If you liked the Wild Imaginings energy from this newsletter, you'll love this.

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I'm Watching/Listening...

  • โ€‹Leading from the Fear of Regret - I met Laurence and Sally-Anne at the Alptitude retreat this summer. This is a great conversation they had together about using the fear of regret as a driving force instead of the fear of getting it wrong.
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  • โ€‹For The Lonely, Suffocated, or Overextended - Nedra Glover Tawwab (my new fav obsession!) talks about the silent agreements we make in relationships without ever saying them out loud, and what to do if you feel like you don't have enough friends.

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I want you to know how much I appreciate having the privilege of being in your inbox and a part of your life.

I love having you in our community and value hearing from YOU.

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Thank you for reading :)

PS: Love the content I create for you? Been a long time reader? Now you can show your support for my work by buying me a coffee โ˜•โ€‹.

Lydia Lee
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The "I Help You Create a Second Act in Your Business" Coachโ€‹
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Screw The Cubicleโ€‹

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โ€‹Work With Me โ€ข Binge Video Episodes โ€ข Say Hi on LinkedInโ€‹

Screw The Cubicle

Hi, I'm Lydia! I help solopreneurs build tiny but mighty businesses they can run in 25 hours a week or less. Every month, I share real advice on simplifying your business, reclaiming your time, and creating more freedom without sacrificing income.

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