Quitting My Day Job: What I Learned the First Year

 Hi Friends!

I get a lot of questions about supplies, training etc. but by far what I'm most often asked is how I quit my day job.

I get it! Having a plan is key. But don't expect a one-size-fits-all strategy, as reassuring as that would be. I remember in my most desperate moments I'd  google "how to quit your day job" as if there would be a blueprint for me to follow. Yes, I really did this! Someone had to have a how-to guide for what I needed to do to achieve this goal! I wanted steps. I wanted instructions. I wanted a check list.

Well I don't have a check list. But I do have some things I've learned along the way that have worked for me over the last year. (Notice that this post is not titled HOW TO QUIT YOUR DAY JOB because unfortunately I just don't know how you should quit your day job. There are too many variables-- we're all different, our personal circumstances are different, our day jobs are different, our budgets are different and our ability to tolerate eating ramen night after night differs too.)

1. KNOW YOUR NUMBERS. I've heard all sorts of quitting your day job stories that involve winging it. Just taking the leap. And believe me this was a fantasy I coveted for a long time. For some people that strategy might work but being that I'm 45 and have a husband and daughter in college and grad school, and a mortgage, the idea of winging it just wasn't for me. So by "knowing your numbers" you:

  • know precisely how much money is coming in and how much is going out and can estimate how much you will need to make to cover your expenses when you quit your day job
  • know what you'll do when you lose your day job's benefits
  • know what in your budget is necessary (food, shelter, ridiculously expensive coffee) and what is negotiable (cable TV, clothes, ridiculously expensive paint)
  • know how quitting your day job would affect your ability to pay off debt, buy a house, manage your retirement, grow your savings, etc
  • know exactly to the penny what your costs are for producing your product and then price it accordingly

2. BE REALISTIC. I have a wonderful house in the woods that makes me really happy. I do not however have a Pinterest-worthy art studio with enough storage space. Having most of my shipping supplies in my bedroom is not ideal but this is what I have right now and I make it work.

When I envisioned quitting my day job I needed to be completely realistic about what I *needed* vs. what I *wanted* in order to be self-employed.

  • Do you need to have a custom studio before you quit your day job or can you work at your dining room table?
  • Can you work at home or would you prefer working in a space outside of your home? What would this mean for your budget?
  • Can you tolerate having your shipping supplies in your bedroom or do you need to renovate your garage before quitting your day job?
  • Are you sure you can do without ______________. In my case my husband gently suggested that I was not being realistic about all the things I could cut from our budget in order for me to quit my day job. i.e food....

3. INVEST IN YOUR SUCCESS. Every year I splurge on a big ticket investment for my business. This was significantly easier when I still had a day job because I invested much of my art (extra) income towards getting strategic guidance for how to set up and then grow my business. The longer I hung on to my day job, the more money I had to spend on these services.

Here are some folks who have helped me along the way. (And I plan a more detailed blog post on this subject soon!)

4. MAKE SURE. My least favorite recommendation before going for it is to.... reconsider. It's important to do, even if you feel sure about what you want. Is quitting your day job really necessary for you to be happy? Because the idea of quitting one's day job has been romanticized a bit in my opinion.  I have a friend who is happy with two jobs and has no intention of quitting her day job. I cut my hours back at my cubicle job until they wouldn't cut them anymore. Would your employer let you go part time instead of quitting altogether?

5. BE FLEXIBLE AND PREPARE TO LEARN AS YOU GO.  If you do decide to quit your day job then go for it 100%!  And then don't beat yourself up if after the first week the transition doesn't go as smoothly as planned. You aren't a horrible business person if you spent your whole first week on Pinterest or rearranging your laundry room. Maybe you thought you'd wake up at 5am and workout before starting your day (ahem, me...) but you find that you work better at night. Maybe you thought you'd have a structured schedule but prefer a more fluid routine.


  •  I am a list maker. Some people have their special way of crafting their to-do list. Just find a way that works for you. I write out my day's to-do list the night before so I'm prepared to get to work first thing in the morning.
  • Put your pants on. And shoes. And for me, add make-up and a bra. I get ready the same way I did when I headed to an office every morning. It changes how I see the day and how I approach my work. Nothing says we're having a lazy day like sweatpants and fuzzy slippers.
  • Hide your phone.
  • Keep your environment consistent.
  • Honor the schedule you create but take advantage of the flexibility self-employment offers.

7. BALANCE IS RELATIVE. I don't strive for work/life balance because I don't think my life needs to always be in balance. When I'm passionate about a project I work on it 13 hours a day and on weekends. And I love it! And then I am religious about taking a good long break. So, balance for me can have long and short cycles. I do make time for the things that fuel my work: being in nature, reading poetry, travel, museum visits, etc.

8. CREATE EVERY DAY. Even if it's just for a few minutes a day. It helps me not put too much pressure on myself.  If it's been weeks since I painted than there is a pressure that the next thing has to be GREAT.  I try to paint a doodle every day just to keep the momentum going.

9. EAT THAT FROG. Have you heard this before? Basically it means do the thing you most DON'T want to do first thing in the morning. For me this means processing and packaging orders in the morning so I don't procrastinate and end up doing them at 10 o'clock at night. Whatever it is you're dreading, get it done FIRST.


  • I read and re-read this post on how Kate from The Dapper Jackalope set up her work schedule. It's still what I aspire to!
  • Read this book! Very helpful in figuring out how to get the most from your workday.

Well I hope this has been helpful! I would love to hear from you! Are you still balancing two jobs? Self-employed? What strategies are working for you? Any gems of advice we should know about?



Photography by Kate Schwager 



Very well written & yes, very helpful. My current position that I climbed the ladder I’d unfortunately no longer the best for with my health (several autoimmunes). I follow a couple of life coaches who are very good but the message is always the same…just quit. Ironically, these same people come from backgrounds that afforded them the luxury to leave their day jobs in pursuit of their dreams. And if I hear one more time, focus on manifesting money & the money will come…I am going to scream. Thank you for your advice!

May 30, 2018


I laughed when I read you’re not willing to give up ridiculously expensive coffee, but can go without ridiculously expensive paint :)
And eating that frog…I’ve learned this many times in farming and writing. So necessary, and makes everything else feel easier!
Cheers to making the transition, and thank you for sharing your journey!

Jan 05, 2018

Laura Bray:

Excellent post Lori! Thanks for sharing. I completely agree with the getting dressed advice. If I stay in my pajamas it can sometimes put a halt to my work because I might need to run out and get a supply for a project I’m working on. If I’m in my pjs, I tend to put the entire task off because I would have get dressed etc. to go out and get what I need. Sounds ridiculous, but it really does make a big difference.

Jan 04, 2018


Thank you for this post! I’m not quitting my day job because I’m not actively creating or growing any ideas for what I could produce on my own, but I sure do romanticize the idea of quitting my day job. Even so – there was a lot of little petals for me to gather from this post on what I can do to switch a few things to make my days happier and to let in a little room for creativity. The idea of ditching the “work life balance” really calls to me because it’s something I’ve never been able to achieve anyway so it’s just a guilt anchor!

Jan 04, 2018

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