How to Know When It’s Time To Quit Your Job

Some links included here may be affiliate links, meaning we may earn a small monetary bonus from referring you to them. In no way does this increase the price you pay.

Since late 2014, a few months after I started Bright Cents, I knew I was on a journey bigger than just paying down my student loans. I could feel that this was like the gates to something bigger, but I didn’t know what or why.

I was reading and learning about financial independence, retiring early, being debt free, and was feeling so energized by everyone I learned from. I woke up excited to learn more and teach others what I was finding.

Then I discovered podcasts.

I started off listening to the Dave Ramsey show (a recommendation from my coworker at the time – thanks Nicole!) and was loving it. I learned a lot but after a month or two was getting kind of bored with what his show was providing.

I looked around the iTunes/Podcast store to see if another financial favorite of mine, Suze Orman, had a podcast version of her show, and of course she did. I listened for a few weeks but then got bored again (an hour commute each way gives you a lot of time to consume podcasts).

I did a search for something related to money, and I then found the podcast that would change everything for me: Smart Passive Income.

At the time, podcasts were big, but they weren’t as mainstream as they are today. I had never heard of passive income and was curious what that was, so I downloaded an episode.

It was episode 3 of the Smart Passive Income podcast and it seemed pretty interesting from the description.

This episode was all about how Glen Allsop of ViperChill had built a ton of affiliate and niche sites and was making a gobs of money.

At the time, my brain could barely comprehend this. I had never considered the fact that a regular person could make money online like that. 

It sounds bad, but I hadn’t really thought about there potentially being another path for people like me. I was average, boring, and felt I had no over-the-top skills to start something of my own— it just never really crossed my mind.

My Journey Into Online Business

I was doing dishes at the time I listened to episode 3 of Smart Passive Income and got chills immediately. Something about this felt so right.

I listened to the episode again and then started doing some research.

This niche site thing seemed fun, but I didn’t know if it was exactly what I’d be good at. But I was definitely interested in this whole online business thing.

I stopped listening to everything else and consumed only this podcast. Pat Flynn, all day, every day.

I started learning more about niche sites and blogs, and decided to start my own. A few months passed and I decided I wanted to write about my student loans and how I was paying them off.

No one I knew was talking about this stuff in public. With friends, we’d get on the topic of being broke, laugh, and throw out numbers of what we owed for our degrees, but that was it.

I also felt like having all of my information out in public would force me to work harder towards paying off my loans and stop spending mindlessly.

I knew money was a taboo topic, and most people don’t talk about the nitty gritty details over drinks, so I felt this was the next best way. I just wanted to talk about this and help my friends in any way I could.

I started the site and wrote consistently there every week for about 2 years. I published debt reports on how much I had paid off each month and how I had done that.

Before I knew it, family, friends, and even strangers were reaching out for advice on how to get out of their own debt faster. I loved helping wherever I could.

From Blogging to Business

As time went on, my podcast listening habits switched from Pat Flynn to more mindset/business type stuff, Achieve Your Goals with Hal Elrod, then Fizzle, and then the one that changed me: Gary Vaynerchuk.

Gary has impacted my life in many ways. Most importantly, he helped me realize that I didn’t want to be working the same job for someone else the rest of my life.

I wanted to do my own thing, and take my skills outside of the workplace to help more people. Especially people I cared about vs. one larger organization.

I started helping family and friends with marketing work and building websites.

They started to pay me.

And then they started to refer other people to me.

Sidenote: The personal finance blogging community has been especially helpful in getting the word out. Such an amazing group of people right there. 

With all this extra work meant a lot more time was needed to keep up.

Before I knew it I was working 3:30am to 9pm. My schedule looked like this:

  • 7am-8am — Take the train to my day job (write, listen to podcasts, read)
  • 8am-12pm — Day job
  • 12pm-1pm — Walk outside and listen to podcasts, or work on client stuff
  • 1–4pm — Day job
  • 4pm-6pm — Commute home (write, listen to podcasts, read)
  • 6–9pm — Work on client stuff
  • 9-9:30pm —Go to bed and do it all over again

People thought I was insane, and rightly so – it was tough, but I flung out of bed (once I got over the 3:30am thing) excited to get started. And a short Gary V podcast in the morning re-energized me even more.

Saving Every Dollar I Could

With this new schedule and new goal of leaving my day job, I changed my money focus quite a bit.

I started saving money instead of using it to pay off my student loans faster. And then I realized I couldn’t write my debt reports anymore, and I stopped writing for Bright Cents audience altogether.

I wrote a few posts about money but it didn’t feel right because I wasn’t being completely honest anymore with my audience.

I felt terrible about it because I knew I was helping people learn about their finances, but I also knew that I couldn’t write about what I was actually doing.

My coworkers and boss were reading the site so I couldn’t exactly post about how I was saving money to eventually quit my job.

But that’s what I was doing. I even had a goal date in my head: June 1st.

And over the course of 12 months, I had saved up $22,000 as an 8 month “runway” — i.e. money to have in case everything I touched turned to crap.

I started getting more clients to the point where 3:30am to 9pm wasn’t cutting it anymore.

I had to make a decision — stop taking on clients, or leave my day job.

I was almost at the point of having enough money saved up, and once that happened, I knew that I had no more excuses. I was going to actually quit my job.

My comfy, secure, day job. June 1st was becoming a reality.

I wrote out my resignation letter, but didn’t print it out. But once I did that, it made me extremely uncomfortable to even sit in my chair at work.

It was scary, exhilarating, and made me question my sanity.

Every. Single. Day.

May 1st came and I had enough money saved to live off of for 8 months if I didn’t make a single dollar after I left.

I handed in my resignation letter shortly after.

My boss and I both cried when I gave it to her. I loved the people I worked with and for, but it just wasn’t healthy anymore to keep living like I was. Something had to give.

My Last Day as a W-2 Employee Had Arrived

My final day came and went, and it was like a wave of relief fell over me.

All of the hard work, saving money, stress, anxiety, the tears, the laughs, and the long hours of that commute were worth it.

I published this on Facebook two weeks before I left my job – this is my “I’m terrified but am going to try my damnedest to make this work” face 🙂

3 Months After Leaving My Job

It’s been almost 3 months now since I had my last day with that job. I’ve made mistakes and dumb moves, but I’m learning every day.

I’m finding new ways of getting things done and meeting lots of new people. It’s great and I wouldn’t change that decision at all.

The biggest thing I’ve learned so far, is that you can take that big scary goal and turn it into a reality. All you need is a plan, and the support of your loved ones, but most importantly, yourself.

You can’t do this without you, I promise you that much.

3 thoughts on “How to Know When It’s Time To Quit Your Job”

  1. Thanks, Jay! Honestly, the hustle of trying to learn and blog about money/budgeting will cement it better than anything I could ever say. Although, the number one thing is to be consistent. Don’t quit. Write every week (or whatever your schedule is) and even if you finish at 11:59pm the day you said you’d write, do it.

    • Thanks for the tips Chenell! With $800,000 in debt, I’m hoping our story can inspire someone else who might be thinking they are in too deep or not know where to start.


Leave a Comment