I Accidentally Rebuilt the Job I Quit 😲

A rescue kayaker, a strong current, and the day I looked up and saw how far I was from the shore

Prefer to listen? There’s an audio version above.

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Yoo-hoo! I’m Caroline. I write dystopian fiction set in a flooded world — and this is where I show my work.

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I stopped this swimmer from being swept out to sea without ever touching him. How?

🌊

I was a rescue kayaker for the Escape from Alcatraz triathlon in San Francisco in 2019. The rules were, if the swimmer touched your kayak, they were disqualified.

Seems reasonable enough, since it is a race, except there was a very strong outgoing current, and I was assigned an outlier position in between the race course and the Golden Gate Bridge, which leads to the open sea.

This poor guy who drifted into my Zone of Supervision was clearly not a very strong open water swimmer. (Otherwise, why was he all the way out here with me, and not on the race course?)

The Alcatraz swim is a VERY technical 1.5 mile swim. It’s 50-58F, which leads to disorienting cold water shock upon entry, then you’re dealing with intense currents that require intentional navigation, and choppy waves impede your visual sighting.

So, back to our poor guy, who is meant to be going left, but keeps swimming right (remember the current?). I can’t touch him, so I am constantly rearranging my kayak into his line of sight and banging my oar, but swimming is NOISY, and he’s buried in waves, so for over an hour, we do the following:

• he swims and nearly collides into my kayak, which is blocking him from being swept out to sea

• he is confused, he angles left, facing shore, and swims a few strokes

• the current pushes him back toward me

• repeat

He is not happy. And now he’s tired, and embarrassed, and he’s still not accounting for the current. Finally, he gets to shore. . . a mile down from the transition area, so now he has to RUN a mile, in his WETSUIT, to join back with the race, where he will have to then do a hilly 18 mile bike ride, then an 8 mile run.

Poor dude. The look on his face when he neared the shore and realized how far off-course he had gotten?

I’ve felt like that recently.

When I quit LinkedIn in 2020, I gave myself one year to write. At the end of that year, I was hooked. I knew I could never go back to corporate. But, I needed some way to make money.

I ended up working part-time with an old college professor for his new startup. I helped him launch their 2nd facility in 2021, and now, we are launching their 27th!

The thing is. . . there’s no upward mobility there, and that’s been fine because I haven’t wanted that! I’ve stayed in this job because it’s been a stable source of income, working with someone I enjoy, on a cause I feel good about (dental surgery for low-income and special needs children) AND it supports my pursuit of writing.

It was all working out perfectly. I had just revised my first book, MAY WE PLEASE THE SEA, for my agent, we were about to go to publishers. But then my agent dropped me.

And that’s when I started drifting. . .

First, I stayed focused. In Fall 2024, I found a second agent for MAY WE PLEASE THE SEA, but their legal contract was problematic so I walked away, and I was so burnt out on that book, that I focused on writing my second book idea, MOONSHOT, instead.

Then, I sent MOONSHOT to agents in Fall 2025, and I was so tired, that I stopped writing anything new. I waited.

I was treading water, no longer racing, and the current pushed me off-course.

You see, I didn’t want to write more until I knew what would come of these two stories I’d already written. I knew that another story meant committing to at least another full year of focus and energy. And did I want to put myself through that again, when I already had two books, with no success?

So I waited for agents. And in the meantime, I took on more consulting clients. More work.

And then one day, I looked up and saw the shore, and how far away I was for the race I had signed up for.

The Job I Escaped, Rebuilt

I hadn’t written in months.

The full-time corporate job I had escaped? I had re-created it for myself, client by client.

Sure, I was working from home, and I controlled my work, and my schedule was flexible. . . but it was one day, when a client of mine was offering to refer me to other people, that I realized. . .

I don’t want more clients!

This work was only supposed to support my dream. This isn’t my dream.

And like poor ol’ swimmer guy, I popped up confused, so far from where I was originally intending to go, and feeling like I was fighting against the current just to get back to where I was.

What Will I Actually Regret?

Recently, I heard someone say, “when you’re on your deathbed, what will you regret most?”

I closed my laptop, put away my phone, and went into my hot tub, with just me and my brain thoughts and Fletcher (because he’s always there).

The one photo I have of me in my hot tub, featuring Fletcher and a pimple sticker

I made myself sit in silence and really think, beyond the should’s and the could’s and the pressure of more clients, more money, what will I actually regret on my deathbed?

I immediately thought, “well it won’t be, ‘darn I should’ve signed another client.’”

That’s when I knew. . . I had drifted.

And as I stared up at the full moon, the next thought that came to me was, so strongly: MY BOOK.

It was so obvious and yet, so random. I hadn’t thought about my books in MONTHS. My silly books that had taken so long and given me so much heartbreak.

When I told David, he asked, “Is the act of writing enough? The fact that you wrote two books? Could you put them in a drawer and be happy?”

I think I actually stepped back in disgust.

For me, it’s not the proof of “could I do it?” It’s the joy and connection of sharing it. I had glimmers of that with my beta readers and it was so special, so energizing.

But I’ve lost it since.

Angling Back Toward Shore

I had already planned my client work, and my future client work, and I easily saw a path there for how to bring in more money.

But that’s not what I’ll regret.

So, I’m proud to say, I’ve stopped taking on any new clients.

My even bigger Big Move?

I ended work with my second largest client, one who was taking up a significant amount of time. (No, don’t worry, not my old college professor and the dental surgical facilities for low-income youth, that’s still my part-time).

I am freeing up time for writing. I am angling left to get back to shore.

Next Saturday, September 12th, I’m going to share my ~ Big Announcement ~ with you. I don’t think you’ll guess exactly what it is. . . because it’s evolved.

P.S. Do you feel like you’ve drifted off-course from whatever you’re working towards?

Hit reply and tell me. I read every one.

This was back when I lived in San Francisco, with the South End Rowing Club in Aquatic Park. They judged you if you wore a wetsuit. So I became acclimated to swimming sans-wetsuit in 50F! This race was Cinco de Mayo, where we swam up to 5 laps of Aquatic Park and took a tequila shot every lap. Hence my goofy smile. I stopped after 2 laps (2 miles), freezing and drunk.

🌊❤️,

Caroline

About the Author:

Yoo-hoo! I’m Caroline, the author behind The Deep Dive. When I’m not writing, you can find me gardening my veggies and fruit trees, training my German Shepherd to talk with buttons, and training to do pull-ups. (I’m almost there!)

🌊You can also find me on Instagram.

💬 Feel free to like or comment on this newsletter so more Substack users can find it!

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