Leaving The Nest: How to Know it’s Time to Quit your Day Job

This contributor post was written by Vanessa of Thrift Core.

You just can’t do it anymore. Every time you clock in at the day job, your soul dies a little bit more. I know because until last week I was right there with you, working as a writer in a cubicle. Now I’m a freelance writer, PR assistant and artist and I want to give you advise of leaving the day job, too.

I wasn’t too hasty, you shouldn’t be, either. Here are 5 Ways to Tell You’re Ready to Quit the Day Job and become a full time Creative:

1. You’re Making Money From Your Creative Efforts

Do you have a steady revenue stream coming in from your creative endeavors? Are you positive that you can make more if you were able to transition to it completely? If so, you’re ready to go!

2. You Can See Yourself Doing Your Creative Self-Employed Work for Years

Turning your crafty hobbies into full time work could take the magic out of it for you. You need to be able to see yourself doing your creative job for years without it losing its allure.

3. You Already Have a Five-Year Business Plan Ready

A business plan is essential before you fly free. If you need help writing a business plan, I highly recommend Brittni’s Track This if you need help writing a business plan.

4. You’ve Already Put in Years of Hard Work

I didn’t blindly quit my day job without a safety net in place. I’ve been working hard at networking in the art community, building up clients, and building up my side-business for almost as long as I’ve been employed as a webmarketer. Sometimes it took working 80 hour work weeks (50 at the office, 30 more at home!) to make this happen, but it was all worth it in the end.

5. You Can’t Focus at Work; All You Think About is Your Creative Job

This is a big one. Sometimes it will get to the point that you just CAN’T cut your day job anymore. If your creative work is all you can think of, you need to put that energy into it so you can move forward.

If the five above facts apply to you it’s time to move on to becoming a full time creative. I know how you feel, you’ve completely outgrown the “nest” that was your work. It’s time to fly free.

Good luck, and remember to tackle your new creative career with the same dedication you gave to your former boss!

image Quit your Day Job

Vanessa wrote this post. She is a full time copywriter and webmarketer with a passion for art, creativity, and thrift. She writes about thrifting, creating, and saving money every weekday on her blog, Thrift Core.


17 comments | Click here to reply

RT @papernstitch: is it time to quit your day job? http://t.co/EUrWqBE1

Kirsten Löser (@FleurDeBoheme)

Hopefully! RT @papernstitch: is it time to quit your day job? http://t.co/PToMSLkv

Mariah Danielsen (@mariahdanielsen)

[…] Leaving the Nest: How to know it’s time to quit your day job. […]

Oprah on Surrendering – Wonderful Wednesday » Alex Beadon Photography

Thanks for the great post! I have a day job I’m not fond of so I’ve been thinking about this a lot lately. It can be hard not to jump the gun and quit early.


My last day of work is this friday the 14th, and it´s been a hard desicion but I can´t help to think that if I had the time I will creatve beautiful things. So I decided to quit.
It´s gonna be very hard, but I know that I will make it.
My sister and I have this business of selling bows for little girls and this 2 years have been amazing.
I can´t belive what I read this morning in my mail, “How to Know it’s Time to Quit your Day Job” perfect timing thanks / from México 🙂


I like my day job so I don’t plan on quitting any time soon, but balancing a blog and creative work along with a full time position is definitely difficult. I really enjoyed this post and I agree with some comments above that thinking about taxes and health + life insurance and having a solid savings to fall back are definitely things to plan for and consider.

Down and Out Chic

Matt: Thank you for sharing your inspiring story, ups-and-downs included. It’s not the easy route, not by far. But it’s the most rewarding.


This is a great article and should be very eye opening as people approach this question.

I quit my day job about 2 years ago. My wife still works part time at the hospital to get our family insurance, but her take home is about $150 per week so I am the primary bread winner.

The biggest wake up call going from full time employment to full time self employment are the ‘minor issues.’ Taxes, which used to take about 20 minutes a month is now a couple hours a week. Supplies went from about $1,000 per year to well over $15,000.

The selling cycle is very eccentric. I made over 3/4 of my money in 3 months. My first year, I was not ready to stretch that money for the rest of the 9 months and went into debt buying raw materials. I’ve corrected that mistake, and I’m looking for ways to balance the selling cycle.

There are reasons not many people go this route. Examine yourself and understand if this is a day dream or a career move. Look for support, both business and personal. It’s ok bootstrapping your business while you develop. It was my goal to do this without debt, and I almost succeeded. I’ve recovered from last years debt, but it did cause a few sleepless nights.

When you’re ready, buckle up and get ready for a fun but lively ride.

I strongly urge people as they reach for self-employment in the artisan fields to create a few core products. Something that can pay the bills and you wouldn’t mind doing for 10 hours a day 6 days per week. Then also make sure you take time to let your creativity flow. The fun projects will keep you fresh and happy while the core products keep you fed.

Matt Beaudoin

Great post, and good advice as well from the comments. I am a full time creative, and it’s very helpful to plan ahead when you know you are going to take the leap – chart out those living expenses to savings ratio – especially if you are in a “ramp-up” phase. Also, place some “deadlines” on yourself for the amount of incoming work / income you’ll need to support you and your family. Don’t be afraid to hit that deadline and go back to work if you need to (make sure to schedule in time for the job hunt) You might find something in the way of consulting, part time, or work from home that still allows you the freedom to continue your passion. The road will not always be paved as you envisioned, and you may hit tough times. Have the resilience to do what you must do to survive, even if some of your dream goes on the back-burner. I’ve found that even “time-away” has brought tons of perspective on the direction of my work and brand. Never give up, and remember that there very well may be hiccups along the way. Be willing to be flexible, and always keep the dream alive!


Jenni: Excellent point! Having support helps immensely. I’m starting my brick & mortar with a group of people, and this helps tremendously. Networking with other freelancers and arranging dates when you can work together and help each other is a good way to get things done; you feed off each other’s energy.


Christine: 5 hour commute! I can see why you took the leap and decided to quit. It’s never easy, but the hard work is always worth it!

Hannah: You’re right, that was another point I wanted to bring up. People wait and wait for the “right time” to leave their day job, but there’s never a “right” time, it’s always a risk even with ample planning and money in savings. But when you’re prepared, it’s a risk worth taking.


Thanks for this! Working for myself is all I have ever wanted to do, and I am taking slow and steady steps to achieve this in 2012.

I think planning is vital. However, I also think there comes a point where you just have to do it. You’ll always be leaving a secure job with good benefits and that will always be scary. Sometimes you just have to know that you’ve done everything you can and that they time is now and just do it!

Hannah @ Sparrow + Spark!

I had a 5 hour daily commute before I quit my day job. There was absolutely no way that I could transition like that. I had a few dollars in savings when I quit my job in June. It hasn’t been easy but I have had no regrets!


Thanks for telling your story Jenni. The process was gradual for me too (over the course of about a year). Another great post Vanessa. Thanks for sharing!


A big part of the transition to work independence for me was having the support of my family. A supportive husband and kids made it possible for me to build a successful business. It was more of a life change than a career change–and it wasn’t one big step, but a series of small steps over years.

For me, it wasn’t a question of just switching from working a job to running my own business, it was gradual, and I am still working on building it, 20 years since I “started”. Always learning, always moving up a step, still pulling all-nighters…

Jenni Bick

Alexandra: All good points. It’s important to have income coming in when you make the transition. You have to pay the bills!


i think the one of the biggest things is the business plan if someone is really serious about quitting their day job. it takes into account the whole picture – money, market, demographics, growth.
but i also think people need to consider a whole lot more – how will you pay for your health insurance? do you have dependents & how will you provide for them? and the real biggie – how will you make money if you suddenly can’t work?
it’s a really big step!

alexandra keller
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