Let's Talk Wellness: Pivots & Permission

Happy May! We are almost halfway through the year. Which depending on the day, that can feel like a victory lap or a bit of a panic attack.

I’ve realized that when I feel “behind” it’s usually because I’m measuring my progress against an “expected path” rather than the one I actually want to be on.

I just hit my 10-year milestone of graduating from college (still can’t believe it), you can read my quick reflection here.

Looking back, it's so crazy to see how my path has changed.

I’m so glad my life looks nothing like I had planned.

Last month, we talked about the clutter in our heads, and this month, I want to talk about what happens when we clear that space and start building a life that feels like ours.

I met Kelsey Shipman in a coaching program earlier this year, and was inspired by her life story.

Kelsey is a Writer, Book Collaborator, and Award-winning educator (to name a few!) who currently lives in Mexico with her family. I loved learning more about the career path that led her to where she is today.

We talked about big dreams, pivoting when life shifts, and how to stay connected to your own voice.

So let’s get into it!

Shaina: Before we dive in, I’d love for you to introduce yourself: who you are, what you do, and what kind of work lights you up right now?

Kelsey: I’m a ghostwriter and educator. I work mostly on cookbooks and memoirs, and I also co-run an online community called Write Up with Hannah Howard for writers working toward traditional publishing for their first book. 

I love working on cookbooks because they’re some of the most beautiful books out there, and more and more, they’re also becoming vehicles for memoir, which I love. 

I do my own writing too, and have the most fun publishing my Substack, Cheese Toast with White People, where I write satirical recipes and memoir pieces. 

Shaina: Was there a moment where you realized you didn’t want to keep following the “expected” path anymore? What did that shift look like for you?

Kelsey: After I had a baby, everything changed. I’d been teaching in schools for almost fifteen years, and I suddenly felt like I couldn’t go back. 

Kelsey Shipman, Writer, Book Collaborator, & Educator

With my own child at home, I didn’t have the patience or emotional bandwidth for other people’s children in the same way anymore.

Like a lot of educators during the pandemic, I left traditional education and started looking for what came next: something that gave me flexibility, allowed me to be with my baby, satisfied my need for creative expression, and could earn more than a part-time income on part-time hours.

That’s how I moved into ghostwriting and started building a career working on books for other people.

Shaina: A lot of people were taught to follow the “right” path: good grades, stable job, checking all the boxes.

Was there a moment in your own life where you realized that path didn’t feel aligned anymore? What was that like for you?

Kelsey: Oh, yes. I was definitely a good girl striving for perfection for most of my life. I still have some of those tendencies, but I really love being my own boss.

After I had my daughter, I just couldn’t imagine asking permission from a boss to stay home when she was sick. 

I think for most entrepreneurs, once you get a taste of freedom, it’s really hard to go back. I can’t imagine having to ask permission to leave work early or take a vacation. I love being in charge of my own working life, even when it’s hard or scary.

Shaina: Oof, I feel that! That good girl label hits home; it’s like we are programmed to wait for that gold star. You mentioned you love being in charge even when it’s scary.

When you think about “big dreams,” in that context, what does that actually mean to you in real life?

Kelsey: I think the biggest dream for most writers is being able to make a comfortable living doing what you love — and, ideally, only what you love. Most of us want to spend our days writing.

That’s why I love ghostwriting so much. I mostly just want to write, and I care less about the ego part, so I’m very happy being paid to write other people’s books. 

It isn’t the same dream as living entirely off my own books, but the big thing for me is that I get to spend my work time writing, which is what I want more than anything.

Shaina: I love that perspective, that the “dream” is the doing, not necessarily getting the credit. But taking that leap to write for yourself (or others) is a big move!

When you started thinking about going after something bigger, what came up for you emotionally or in your personal life?

Kelsey: I’m married, and there have definitely been moments where I found myself having to convince both of us that this was the right path. My income isn’t just for me anymore, so starting my own business was a risk for our whole family.

But I’m really happy doing this work, and I think my husband sees that. We’ve both worked hard to find ways to make it work.

Shaina: What’s a belief about success or productivity that you’ve had to unlearn in your own journey?

Kelsey: I’ve had to unlearn the belief that you have to work all the time, every minute of every day, to be safe or make enough money.

That’s an old belief for me, and it really doesn’t get me anywhere.

Rest is just as important to my creativity and workflow. I often come up with my best ideas or best writing when I’m relaxed.

Shaina: How do you know when it’s time to pivot versus “push through”?

Kelsey: I’m still figuring this out! For me, I have to be making a lot of money to continue with a difficult client or stay on a project that is falling apart.

But even then, I sometimes get to a point where no amount of money is worth feeling miserable doing something I love. 

It’s usually an emotional gut decision for me, and unfortunately, it’s often one I wish I’d made earlier.

Shaina: You talked about unlearning the need to work 24/7 and leaning into your “gut” for pivots. For someone who isn’t ready to quit their job tomorrow or even just wants to feel more connected to their dream, what’s one small shift they can start today? 

Kelsey: Block off time every week to do it. It can be just one hour a week, but I suspect the more you do the thing you really want to be doing, the more clever ways you’ll find to keep doing it.

I make time for my own writing in between client work because if I don’t, things get out of balance and I start to feel my own voice get emaciated. 

I know I have to do my own writing in order to keep writing well for others, so I prioritize it at least once a week.

Shaina: If someone feels stuck or like they’ve let their goals slip, what’s one thing you hope they take away from this conversation?

Kelsey: Get into community. The best thing you can do is find other people doing what you want to be doing and start talking to them. 

That’s why I started my online community for writers pursuing traditional publishing for their first book. I wanted a place to share notes, brainstorm, and learn with other people who want to do what I’m doing. 

It has made all the difference in staying motivated. Find a community for yourself, and you’ll realize we’re all figuring it out together.

Final Takeaway:

Thank you so much, Kelsey! My biggest takeaway from our conversation is that “The Dream” doesn’t have to be a shiny, perfect destination. It’s the freedom to choose how we spend our hours and who we spend them with.

It’s about finding little ways to support what we actually like to do before our voices start to feel emaciated.

Your May Wellness Challenge:

This week, I invite you to take Kelsey’s advice: The One-Hour Block. Pick one thing you love: writing, gardening, researching that business idea, etc., and put one hour on your calendar for it.

No permission asked, no “productive” goal required. Just do the thing that lights you up.

If this conversation resonated with you, be sure to follow Kelsey’s Substack or join her community here.

Here’s to dreaming big dreams and actually making time for the things that really matter!

Love these monthly deep dives? This Q&A is part of The Wellness Edit, a monthly series where we explore the intersection of mental, physical, and emotional health. If you want these insights (and exclusive challenges!) delivered straight to your inbox every month, join the community here.