Jared Seidel
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371 Days with No Job

371 Days with No Job

(Not That Fun)Employment ✂️🕺🏼

Jared Seidel
November 25, 2025

371 days ago was my last day working a full time job.

I gave myself 8 months to figure things out thinking something would suddenly hit me for whats next. That did not happen.

Here's what I've learned from a full year of "figuring it out," including what I did wrong, what I wish I had done, what I actually did between then and now.

Leaving my Job

After I left, I felt the mix of freedom and panic. For six years, my identity was tied to Dexcom. Now, I had to no company affiliation and title that made me feel relevant. I had a hard time separating my work identity from my worth. In this cute little tech bubble that I’m in, we're expected to announce you left your job to start some agentic B2B SaaS tool backed by a tier 1 VC like Sequoia, Founders Fund, or YC.

(this is not real)

I did not. I left because I was burnt out and wanted space. I needed a break. But also a way to stay afloat. So, I sold off a moderate amount of stock and bought myself 8 months of financial runway. Which I believe gave me a shot at starting something. See above for how that went.

Great Advice I got (but ignored)

I got great advice from people close to me that I want to pass on to anyone thinking of doing something similar to what I did. Most importantly, don't be like me: stubborn and ignore most of it.

Take real-time off - travel and disconnect. Just don’t jump into your next thing immediately. You're going to need the time to reset. I cannot encourage you enough to completely turn your brain off from the thought of working. It’s going to feel weird not waking up every day not having to work. But by creating that gap and space it’s a great pause before getting back into hustle mode. It easy to ignore that piece of advice considering you feel like you’re against a countdown but I cannot recommend it enough.
However much time you think you'll need… double it - I thought I'd figure it out in 8 months. It took 12 months to get a rough sense for where I think I need to go now.
1. Because I was so focused on plunge party and bouncing around between idea and idea I didn't spend the time to get a single one off the ground (more on how to fix that below). It took way longer than expected. While I encourage you not to compare yourself to others I realized that this was true for most of my friends that also started successful businesses.
2. It usually tracks as follows: yay I quit my job → I don’t know what the fuck I’m supposed to do → 12 months go by → let me try this → fuck this is hard → i need to keep pushing → oh this is kinda of working → wow this works. I’m currently in the “let me try this → fuck this is hard” transition phase.
Have (some) Income once you're done with your break - the pressure of zero dollars coming in per month and watching your bank account go down crushes your creativity and ability to make good decisions.
Talk to as many people as possible - Fortunately I did follow this one. During my time off in the limbo phase I accepted every meeting that was sent my way. It opened up doors and introduced me to people i didn't even know existed. By doing this I was able to expand my surface area for luck 10x.
Do something. Yep that simple. if you sit in your room twiddling your thumbs or aimlessly wander the world traveling from country to country for 4 months the outcome will be the same. You haven’t done shit.
1. I was bouncing ideas off of people for 4 months straight seeking validation for an idea before I went after it. In reality the best way to come up with an idea is to find a problem and try to sell a solution. If they pay, build the solution. If they don’t pay, its not a painful enough problem, but make sure you talk to enough people before giving up. (P.S. “building” does not mean building software)

Me documenting Lyft bike rides

What I Actually Did

In my case I wasn't sure what I wanted to do. But I was already running Plunge Party. So I didn't have the luxury of taking time off (so I told myself). I wanted to keep growing it and the momentum it had. I did do a weeklong roadtrip down to southern California, went lobster diving, spent Thanksgiving with a friend and then came back to SF to throw another Plunge Party… not that much time off.
In my case I was thinking about what I was trying to do next. In my head I knew I wanted to start a business. Plunge party made money but it wasn't something keeping me afloat financially, so in my head that didn't count. I kept bouncing around between idea and idea without giving it enough.

Leaky bucket. Three times I thought I had “the idea,” tried to get it off the ground and go “all in” on it only to realize it wasn't going to work. While I’m glad I was able to put my full attention on something for 30 days multiple times, I lost a lot of long term thinking when I am too focused on “how can this make money 3 weeks from now” because I had no income. I quickly switched into a scarcity mindset and was unable to make good decisions.

How to Test an “idea”

If you want to know if an idea is good or not, I try to break that down into 30-day sprints, as I learned from one of my good friends, Natalia (great follow on tiktok btw).

Ask one clear question
Create one clear milestone or outcome
go heads-down on it for 30 days.

If it shows promise, keep going. If not, pivot. That could be as simple as posting a piece of content for 30 days straight (pretty hard). figuring out how to make $100 a day for 30 days in a row (do-able). Or talking to 30 different people over the span of 30 days about a specific problem (i.e. - weight loss)

What I Tried Over the Past 12 Months

Plunge Party - Kind of worked, but not enough
Drop shipping on TikTok shop - did not work because I didn't focus hard enough on it because I didn’t commit enough time to learning. This still works btw.
Sales - Helped a friend with product sales. Got really good at it and learned how to sell my own products better. Made some money here.
Consulting - did a little bit outreach, only to learn that I need to do a better job offering how I can help. (Will be doing more of this soon)
Taught myself how to code - helped get v1 of coaching tool off the ground. Realized that was not where I should be focusing my time.
Build a consumer app - got good at learning how to distribute consumer apps on TikTok but had to pivot due to time to market.
30 Day Glucose coaching - worked, then didn’t, pivoted, and found a better way to make it work (over the span of 6 months). Getting better after restructuring the offer.
Creating content - was dog shit for 3 months. One video hit 1.4M views and I thought I was a genius and I was about to be rich and famous. Had a hard time reproducing it and content has been mid since. Told myself to stick with it and it’s a VERY long game.

What did I Learn?

Be Prepared for a lot of questions that you don’t have answers too like:

whats next
why don’t you got get a job.
explaining this to your parents (hi mom)

The past 12 months taught me that not knowing is the default response. which is ok. everyone says "what's next?" and expects a clear answer, but that's not how it works.

You don't need a pitch deck, or a co-founder, or a venture fund to start figuring it out. You just need momentum and willingness to look stupid for a little while to see what sticks. That’s part of the process.

I've still got a lot more questions than answers, but at least now I know how to ask better ones, and that counts for something.

You’re Awesome,

Jared

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Things Worth Clicking

A few gems I found on the internet this week - no digging required

Building a personal brand vs building a company. Something great to remember as I attempt to do both.
My friend, Scott is starting a company called Thorne the analyzes your poop. He just dropped a TED talk on the power of taking pictures of your poop. Yep.