Thinking of Quitting? Self-Employed Lessons, 2 Months Deep

That first two months after (finally) quitting my job definitely flew by! I’ve had a successful move from New Haven, CT to Portland, OR! Life has been memorable in a gazillion ways, and the fun is just getting started.

Today I bring to you lessons I’ve already learned and that you’ll need to watch out for or can look forward to for yourself.

Self-Employed = Awesome!

So far, 99% of the time has been freakin’ fantastic. You’re probably thinking I’m exaggerating, but I can honestly say I couldn’t be happier with life right now, and I’m committed to doing every possible to keeping it that way.

I’ve gotten to meet a ton of new people out here in Portland, and not having a job to hold me back has definitely helped that. Friday afternoon Dark Knight Returns showing? Sure! Sunday bar crawl? Why not?

It’s possible that I’m still in the post-job haze, but I’m just eating it all up for now until my feelings tell me otherwise.

Having Some Income is Better Than None

Initially, I was going to make the jump from my steady income from job to zero income at all. I planned to save all along, and I ended up with about $7,000, strictly for making the transition to self-employment. But, a few weeks before getting my job, I came across a position that fit in nicely, allowing me to write freelance part-time and still be able to work on projects that I wanted and do other things that I just love to do.

While it would be nice to be 100% free to do whatever I please, having a small income that still covers most of my living expenses has been a huge relief. It’s expanded my time horizon for when I’ll run out of money if my other endeavors don’t bring in cash as soon as I hope. Right now I’m looking at least 6 months of expenses in the bank, so I’m not concerned for that any time soon.

So, I’d recommend: Unless you have solid financial backup, consider being a part-time quitter. This can even work if you don’t have much savings at all but desperately want to leave your job. Freelancing is always an option, but there are some decent part-time options, even some that offer health insurance.

Don’t Forget New Expenses

Speaking of health insurance, you’re going to need to pick up coverage for yourself and potentially your family. I went with eHealthInsurance, and I found a decent plan for about $100 a month. Yes, it’s pretty bare bones with a $5k deductible, but it’s not much worse than what my previous employer offered. Plus, I’m young and happily healthy 🙂

Also, once you have self-employed income, you have to remember to set aside money for taxes. For now, I save 30% which is hopefully a conservative amount ( and I’m overdue to meet with an accountant!)

Advice to ya: Don’t forget to factor these things into your budget before you leave your job, like health insurance and additional taxes, to get a more realistic picture for what your monthly expenses will be like.

You’re Probably Going to Freak Out At Times

I’d be lying if I said that I haven’t doubted myself already. I know it’s early, and I have momentum going for me, but the long-term path still isn’t clear and likely won’t be for some time. I’ve had a few moments of agony, for sure, although none of them had me regretting that I quit my job.

For me, the biggest tool for taking on this one has been positive thinking. It may sound silly, but I’ve gotten amazing relief telling myself “I am awesome, I can do this, and I refuse to fail.”

According to a recent talk I attended at WDS by Brené Brown, it’s our psychological inclination to believe that when things feel good, they can’t last and we wonder “Okay, I feel great, but what’s going to go wrong here? Something has to.” Thinking like that is total bullsh*t, and I’ve been doing all I can to fight any of those feelings and keep being happy.

Do this: Do your best to stay level-headed. It’s okay to use some discomfort to push you forward, but freaking out isn’t going to help you be productive.

Find a Routine as Quickly As You Can

I remember always sitting at my desk job and thinking something like “If I can just get out of here, I can easily add 40 productive hours a week to my freelance work, blogging, and other projects! I’m gonna be banging out blog posts like a boss!”

Fast forward two months: It hasn’t quite been the productive paradise that I imagined. 

Month One (June), I was pretty committed to doing the bare minimum and chilling out (had to catch up on How I Met Your Mother somehow, right?).

July, which was almost entirely in Portland, has gotten better work-wise. It hasn’t been perfect by any means, but I’m slowly discovering how and where I can be most productive.

I’ve finally put the tools from Zen to Done (a simpler version of Getting Things Done) to work to organize my weekly and daily tasks to be more productive. Creating systems has definitely been a key for me, and I think it will set you up for success much better than just randomly trying to conquer your work.

For you: Whatever you need to do to get in the working groove, find it as soon as you can.

Diversify Your Income, and Don’t Work for Peanuts

I already had one slight scare that I’d lost all my freelancing income. It was a terrifying moment (and luckily it was just a quick one), but I’m determined not to wait around for it to happen for real.

You, too, should be thinking about how you can earn your income from more than one source. To say the very least, it’s reassuring to know that your entire well-being doesn’t rely on a single job.

While you’re at it, don’t get desperate and devalue your time and your work. Sure, I’m looking for more freelance work, but I’m not going to jump at just anything, especially if it pays less than my time is worth. I’ve turned down a few opportunities already because of this. I’m not greedy by any means, but I’m not going to work for minimum wage, either.

Have questions about being self-employed? Or is something standing in your way? Let me hear it in the comments!

Note: This post does contain affiliate links, and I will earn a commission if you click on and buy from those. But hey, I recommend these products, and I appreciate your support! 


  1. Jeffrey – I like your balanced portrayal here of both the exhilarating freedom and big challenges that come with self employment. It’s great though that there’s a big virtual, online support network out there of people who will help each other succeed.  I’m slowly but surely tapping into this myself. Cheers!

  2. Jeffrey,I really appreciate the honesty of this post!  You just quit your job, and you’re currently at the beginning stages of what could (and likely will be) and INCREDIBLE ADVENTURE — you’ve got every right to be excited!  I really liked your mention about being a “part-time quitter.”  Of course, everyone has the idealistic vision of quitting and then completely working on their own, but sometimes that’s not always the best thing.  You’ve been an inspiration to me as I have been creating my exit strategy to remove myself from corporate life, and I thank you for that.  Keep up the awesome posts!

  3. I love reading updates of your journey and how you quit your job! Thanks for being open and honest about your experience. Wow, moving from CT to OR is quite a trek and probably a much different culture to get used to. But it seems like you’re starting to fit right in the groove of everything. I especially like your advice about finding some income (part-time or freelance) to pay for a few expenses here and there. That’s a really good idea, and will help your chances of freelancing into full-time income.Not working for peanuts is a big thing too. I think a lot of freelancers start getting desperate or full of fear, so they take any opportunities that cross their path. Yes, of course we need to make sure the bills get paid, but there’s no point in panicking. Great stuff Jeffrey!

    • Carrie Smith Thanks for sharing your comments, Carrie! OR is definitely different than CT, but I’ve had no problems getting used to it. In fact, I probably fit in better here in Portland!

  4. financialsamura says

    Love the update Jeff!  Great to hear you are enjoying 99% of it!  I think that is tremendous! What’s your living situation like in Portland?  Did you bring your significant other?

    • financialsamura Thanks, Sam! I’m living in a house with three roommates. I was lucky to find a furnished place with a friend out here, so it worked out really well and was super easy. And I no longer have a significant other, so it’s just me know. Lots of freedom!

  5. Sounds like you’re getting the hang of part time quitting. 🙂 Where are you most productive? I can’t do much until the baby is in bed…Let’s get together for a beer. 

  6. AverageJoeMoney says

    Great tips. I enjoy self employment, but you’re right…having a routine is key. I have to check out Zen to Done.

  7. I know the feeling Jeff! I’ve quit on May 1st and it’s been awesome. Although I work every day from the minute I wake up until I pass out, every day is just as good as the previous days. Just knowing that if I really wanted to I could do anything makes me fee energized. So three months in and everything is superb.Unfortunately I don’t have the liberty anymore to be picky about my work. I definitely agree that you should always aim to get paid what you’re worth, and diversify your income as much as possible. I have at least 10 different ways I’m making money now. If I lose one of them, I still have the other 9. With that said, I’m still not making enough money to pay the mortgage, health insurance, car payments, car insurance, etc. I had to start being a little less picky on the jobs that I picked if I wanted to pay the bills. So while it’s never a good thing to undervalue yourself and your work, being homeless is also not fun…just be practical. Great post! This is my first stop in. I’m going to stop by more often ;).

    • Although on a side note I’d like to say that I love my house but I wish I hadn’t bought the damn thing in the first place. 

      • LizSeda Thanks Liz, and it’s great to hear more about your story, too! I can definitely understand that it’s tough, and I know I’d have a different mindset if I had to pay for all the things you do! It sounds like you’re a very hard worker, and I hope you’re able to keep moving up in income to a more comfortable level for you!

        • Jeffrey Trull Well as you say, free time is way more important than money, and, if I could, I would sell everything, move into an RV with my two dogs and hit the road (my husband can come too if he wants)! That would be ideal. You start needing less stuff the happier you are…

        • LizSeda Definitely agree after moving cross-country with just a few boxes and bags!

  8.  @Jeffrey Trull  financialsamura Good to meet up in Denver man! Perhaps I’ll attend the WDS as well and we will meet again. I enjoy the Portland vibe. 

  9. 30YearOldninja says

    Hi Jeff :). 
    This is some good content man.
    I’m in a similar situation. I actually live in Japan now. I quit my job in America, and moved here to pursue my childhood dream: to become a ninja :). Basically I came here to train in martial arts full time. One problem- when I moved here my job placed me in the countryside. There were no martial arts dojos. Plus the job was a joke – I was basically a fancy tape recorder, just speaking English words out loud. 
    So I learned the hard way that things don’t always work out as planned. So I fulfilled my contract, left that job and moved to Kyoto (where I am now). I do part time work, just enough to cover expenses and use the rest of that time to train, explore Japan, and work on generating income on my own. 
    I completely agree that it makes the transition way easier to have some outside steady work :). 
    Congratulations on the transition by the way. 

  10. Congratulations on quitting, Jeff. I quit my job as well nearly two months ago. It’s scary. I also felt that I could easily have 40 productive hours, but that is easier said than done. Even so, I haven’t looked back and don’t regret quitting, and I’ve also been able to supplement some of my income from freelance writing as well. Stay at it man!

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