09/22/2026
What if the dread you feel every morning is data — not weakness, not anxiety to push through, but your body telling you something your brain isn't ready to hear yet?
Jess spent 10 years building a tech career she never planned on having. She was the sole provider, a divorced solo parent half the time, and someone who had tied her entire self-worth to the career she'd built from scratch. Then in 2023 she got sick — over and over — colds, sinus infections, a sore throat that wouldn't quit — until a perfect storm of professional chaos and a manager who didn't approach her with care forced her to take medical leave.
And on that leave, she finally gave herself permission to stop.
This is Jess L. — founder of Not Working in Tech, where she helps people in corporate tech navigate their company's leave policies, take the break they need, and figure out what comes next.
In this episode we talk about how to tell the difference between productive discomfort and the kind your body is screaming to move away from, what the year of not working actually looked like — watercolors, solo hikes, road trips to see people she'd lost touch with, why dread is one of the most useful data points you have about your own life, how work isn't working in America and why that's a systemic problem not an individual failure, and what it means to surrender to the not knowing.
If you've been waiting for permission to stop — this one is for you.
🎁 Free resource for when you're in the messy middle → https://itsboth.kit.com/873c6c3733
⏱️ Chapters
00:00 Who she was before — neglecting her own needs while providing for everyone else
01:19 Ten years in tech when she only planned to stay for a stop
02:47 Waiting for permission that was never going to come from the outside
05:19 The line in the sand — getting sick over and over
06:10 The manager who had it in for her and the moment everything broke
07:38 Taking medical leave — and telling her doctor the full truth
08:40 The first Monday of leave — the shift she felt immediately
10:41 The fear underneath the relief
11:16 How long it took to give herself permission not to go back
13:13 How to tell the difference between growth discomfort and "hell no" discomfort
15:27 Why being open to discomfort can also get you into bad situations
17:49 Dread is data — what it's actually telling you
19:12 The meeting she dreaded that turned out to be everything she wanted work to feel like
21:55 What the gap year actually looked like — watercolors, hikes, reconnecting
24:59 How Not Working in Tech was born
27:24 Work isn't working in America — and it's a systemic problem not yours to fix alone
29:44 Take your leave, use your PTO, read your benefits package
31:46 What to do when you don't have a year's savings to take a break
38:00 When she finally felt at peace with her new life
40:56 What to say to someone in the liminal space who doesn't know what comes next
42:06 Surrender to the not knowing
43:55 Stillness, solo hikes, and why being with yourself is so uncomfortable
45:57 Looking at the horizon — the literal science of it
47:42 Why birds regulate your nervous system
48:45 Ridiculous or relatable — saving tinfoil for the dishwasher instead of buying rinse aid
👤 Jess L. — founder of Not Working in Tech
• Website: https://www.notworkingintech.com/
• Instagram: https://www.instagram.com/notworkingintech
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🙋🏻♀️ I'm Nikki P. — therapist turned storyteller, host of It's Both — Living in the Messy Middle. A top 5% podcast globally for people navigating anxiety, life transitions, and the space between who you were and who you're becoming. No toxic positivity. Just real language for living through it.
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