Is It Time To Quit Your Day Job?

Who doesn't dream of quitting their day job? Every day, countless hours are spent in corporate cubicles daydreaming about lives of adventure, creativity, and play — lives spent doing what you love.

Last month, I took the leap. I quit my day job to write full time. Now I'm sitting in Buenos Aires writing while my kids play with their grandparents nearby. And I'm getting paid for it.

To say this is the achievement of a dream would be a vast understatement; I've wanted to be “a writer” since kindergarten. But I didn't just want to be a writer — I worked hard and planned for it.

Should You Quit Your Day Job?
Chasing a dream isn't for everyone. There are plenty of people who prefer the stability and security of a job. Many creative, interesting, passionate people like the advantages of a steady paycheck, good benefits, and the ability to leave work behind at the end of the day.

Before you consider quitting your day job to follow your passions, ask yourself:

  • How comfortable am I taking a risk with my livelihood?
  • Am I willing to maintain a business?
  • How will I handle the business management aspects of my new career?
  • Do I want to do this all day, every workday, or will that strip the joy from it?
  • Will my family and friends support this move?

If you still think you might want to go after your dream, some preparation can make the risks easier and the rewards greater.

Take Your Dream For A Test Drive
It's a big leap from karaoke night at the local bar to American Idol. See if you can find a way to test-drive your dream life before you leap into it all the way. This will give you a chance to be sure it's what you want. You'll also get to fine-tune the details of how you want to go for it.

You may discover that you don't want to do turn your passion into your career. That's fine. One of the most talented singers I've ever known makes her living in psychiatry. As the daughter of two musicians, she knew firsthand singing wasn't the right career for her.

Many people test-drive their dream jobs by freelancing on weekends or evenings. This works for creative fields like writing, photography and music. It's harder if your dream is to open a restaurant or become a civil rights lawyer; some things, you can't just dabble at. But you can still try some jobs on for size by taking a class or finding a mentor. Take a law class at a local university. Cook meals for family and friends. Pick up some night shifts as a chef's assistant.

J.D.'s note: When I was a boy, I not only loved writing, I loved computers. I thought I wanted to be a computer programmer. In the late 1990s, I took classes and read books to learn C++ and various scripting languages. I got my dream job as a computer programmer. I hated it. Sierra's right: It's an excellent idea to test-drive your dream job before you buy into it all the way.

Do What You Love
Yes, it's useful to network and gain experience. But don't sacrifice your time and energy to do things you're not interested in.

When I started freelancing, I had friends and relatives offer me gigs writing ad copy for their businesses or editing their thesis papers. Those are jobs that use the skills I've built up as a writer, but they're not my driving passion.

Since I wasn't depending on my freelance business to support me, I turned those jobs down. I focused on what I wanted to do: creative essay writing and blogging. Staying focused helped me joy out of the work and brought me more opportunities to do exactly what I most love.

Fake It ‘Til You Make It
Play make-believe with yourself right from the beginning. Don't say, “I want to be a singer someday.” Say, “I am a singer.” You may feel a little dopey at first, but you'll slowly condition yourself to believe it.

J.D.'s note: Sorry to intrude on Sierra's article again. I remember the first time I responded to the question, “What do you do?” by saying, “I'm a writer” instead of “I'm a box salesman.” It was liberating. I felt like I'd escaped from a straight-jacket. And after saying it out loud, I began to find ways to make this a reality.

The most important aspect of “faking it 'til you make it” is to be professional. That means setting aside time to work at your vocation, even if it means turning down other fun stuff. It means following up on leads, keeping commitments, and presenting yourself like a pro.

Growing up, my mother told me over and over again, “Writers write.” That's true. But any “dream life” has more working parts than the dreamy bits. Writers write, but they also network, edit, invoice clients, build relationships with editors, brainstorm ideas, and read other writers.

Find out what professionals in your chosen field actually do — maybe through an informational interview — and start doing those things. Right now.

Does your dream require a portfolio? A credential you don't have? A new website? Make sure you have the professional tools to do your work, and then do it. Don't spend a lot of money or time getting set up, though; you'll learn more about what you need as you go.

Make a Road Map
Simply saying “I want to be a writer” was like trying to catch the moon in my hands. Clear goals helped me work. I knew what I was working towards, and I could break down the steps to get there each day.

Don't be afraid to aim high. If you want more than anything in the world to be a contestant on American Idol, write that down and then draw up a plan to get there. Even if you don't wind up singing on TV, the work you do pursuing while pursuing this goal will take you somewhere good.

And you may surprise yourself. When I made my list of dreams and goals, being published in The New York Times seemed like a pipe dream. When it happened, it was just one more step forward with a writing career that was beginning to pick up its own momentum after a year of hard work.

Bank Your Success
By the time I started making money writing, I was sure I wanted to do it full time. So I banked my paychecks in a savings account. My intention was to save up enough money to cushion the ups and downs of freelance income.

Even more important, I wanted to avoid “lifestyle inflation“. I realized that if I simply added my freelance income to my household budget, I'd risk gradually increasing my spending until I depended on my day job and my freelancing just to stay afloat.

So I hid that money from the household budget in its own savings account. I've appreciated having those savings this month while I'm traveling and unable to collect or cash my writing paychecks.

Do the Work
A dream job is still a job. Let me repeat that: A dream job is still a job. When your passion becomes your day-to-day grind, you have to be willing to show up for it just like you'd show up for a factory shift. Be on time, be ready to work, be respectful of the needs of the job. You need to do the boring bits as well as the fun parts, and you need to do it even when you're uninspired or tired or distracted. Just like a real job.

Know When to Quit
How do you know when it's time to quit your day job and go full force into your dream job? Sometimes the date is chosen for you. You've gotten into law school, or been hired as an English teacher abroad, and your new contract spells out the dates.

But if you've been running a side business, you'll need to choose a date and leap. You're probably ready to take that step if:

  • You have substantial savings built up to cover the financial risk of quitting your regular job.
  • Your “side business” is demanding more time from you than you can give it without harming your current career and family obligations.
  • You have ongoing relationships with other professionals and with clients, so you know where your next paycheck is coming from.
  • You can reliably expect to make enough money to cover your living expenses.
  • You've been doing this on the side for awhile, and you still love it.

If you've built up a professional life doing what you're passionate about and you're ready to take the leap, go for it with love and joy. Be happy. I'm incredibly grateful to all the readers, editors, and publishers who've made it possible for me to have this career.

It's hard work, but worth every second of it.

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LauraElle
LauraElle
10 years ago

I am a writer!

Mrs. Money
Mrs. Money
10 years ago

Congrats, and happy birthday Sierra!

I too dream of one day I can quit my day job. I feel like I’m selling myself every day I go to work… It’s not that I have a bad job (not at all) it’s just not my passion.

Van
Van
10 years ago

This post is very timely for me. I work full time as a writer which is a dream itself, but I’ve been slowly building up my side career. I blog about thrift, I’m collecting true vintage treasure to re-sell for a profit online, and I’m researching how to make a full-time living as a reseller. I like my current job and plan to stay here a while longer, but freedom from a 50+ hour work week/setting my own hours would be another dream come true… I’ll keep this post in in mind as I slowly continue toward my goals.

Rob
Rob
10 years ago

I cannot wait for the day until I can completely quit my day job. I am so much less stressed when working on my own business than when working for someone else.

Chickybeth
Chickybeth
10 years ago

Happy Birthday Sierra! Have a great day 🙂

mmeetoilenoir
mmeetoilenoir
10 years ago

Are you sure you’re not starting a career as a psychic, because this is eminently topical in my life right now. I’ve been at the point of taking the jump before, but I always sell myself short and don’t see things through. Thanks for this article.

Happy birthday, too!

Jen
Jen
10 years ago

I feel the same way as Mrs. Money. I have a great job right now but I’m just not passionate about it so I spend most of my days dreading it. My dream is to be a freelance graphic designer…now if I could just get there.

Molly On Money
Molly On Money
10 years ago

I quit my job this spring and before picking up my next gig I ‘tried out’ one of my passions that had just been a hobby- chicken farming! It is a ton of work but I can now say I love being a chicken farmer.

sir jorge
sir jorge
10 years ago

this is a great idea, in theory don’t get me wrong, i love to believe that it’s possible and it’s obvious that people are out there living the dream but there’s never a plan B in these things when emulating the tips, and moving forward, what happens when it collapses? fails? and you don’t make it? i’m in a position where i took the risk and now am floundering in a writing market that isn’t getting me nearly as much money that I need to live on, not only that, i haven’t even been able to find a job…i’m considering… Read more »

Brian C.
Brian C.
10 years ago

At what point can you start “faking it?” Is it when you get the idea to be a writer, when you’ve written in a journal for a few weeks straight, when you’ve posted a blog post, when you’ve published an obscure article, etc…? Or is it just up to you and how much you own it when you say it?

Because I would love to stop sadly telling people, “I’m a Tax Accountant,” and start excitedly telling people, “I’m a Cartoonist!”

Sarah
Sarah
10 years ago

I think the most important bit of advice here is to not let yourself get used to the second income, if the goal is to transition completely at some point. If you do that, you’ll get stuck “needing” your two jobs.

Tawra@Living On A Dime
10 years ago

Hubby quit his job to work for our website 3 years ago. With his two other part time jobs in video he has increased our income by double but he did find out that it wasn’t what he really wanted to do. He’s a video producer and out looking for something in that area now. He might even take what we’ve learned in marketing and start something online but we aren’t sure yet. I would certainly test it out first. He discovered that being a people person he hates to just sit in front of the computer by himself all… Read more »

Money Smarts Blog
Money Smarts Blog
10 years ago

Congrats Sierra!

Given that my two young kids are at home all day, I have absolutely no desire to quit my day job. 🙂

I read your NYTimes article – very good. I’m already dreading those kinds of “talks”.

Mike

Rob Bennett
Rob Bennett
10 years ago

I don’t trust the emotion that says “just hand in the resignation and make it happen.” It’s like lust. It’s a strong feeling but not necessarily a lasting one.

If you can put the effort into putting together a plan and exercise the patience needed to accumulate enough savings to make the plan realistic, I tend to think it’s a marriage, it’s the real thing.

Yes, do what you love. But first prove to yourself that you love it enough to pay some dues.

Rob

Kate
Kate
10 years ago

Sierra makes a smart point about trying it out first to see if you really enjoy treating your passion as work. It’s truly not for everyone. Last year, I began selling my handmade stuffed animals in local stores, at craft fairs and online in my free time. I was so ecstatic and flattered that people wanted to buy things that I designed and made! I started a blog, got business cards made, considered ways to increase sales and marketing, began turning a small profit – essentially turned it into a small business. BUT I quickly burned out. Demand grew and… Read more »

Financial Samurai
Financial Samurai
10 years ago

Hi Sierra, congrats for making the leap.

How long did you work at your other job before being a full time writer?

Thnx,

Sam

Katy @ The Non-Consumer Advocate
Katy @ The Non-Consumer Advocate
10 years ago

Sierra, Great article! I like the “Fake it till you make it” advice. I hadn’t been blogging for very long when an editor wanted me to write a newspaper article on drinking tap water. Until that point, I had only written blog posts, but I sucked it up and said yes. I have also been asked to do talks about Non-Consumerism, and as much as it initially terrified me, I have said yes each and every time. I just pretend that this is a normal activity for me, and figure it out. As far as quitting my day job goes,… Read more »

Nicole
Nicole
10 years ago

Good for you! Btw, I love your posts. Happy birthday!

@Kate #13- Sounds like you need to charge a LOT more for your pieces. Limit demand.

In high school I did an internship that showed me that as fun as it is to READ about genetic engineering, actually being a genetic engineer is one of the most boring jobs in existence. Now I love me some social science– moves a lot faster. I’m glad we’re not stuck doing what our high school selves thought was a passion.

Karen
Karen
10 years ago

I quit my job as a full-time graphic designer for a state university 13 years and 1 month ago. I left to start my freelance graphic design business. It was the scariest, most exciting thing I’ve ever done. It’s worked out very well for me. I’m making more money than I ever could working for someone else. It can be very stressful, too. But, I’ve never doubted that I could be successful. Prior to making the leap, I developed a good client base on the side. I worked my full-time job, plus developed my freelance business for 5 years, before… Read more »

Jeremy
Jeremy
10 years ago

Sierra,

This is an excellent post. It’s a great recommendation to try out your passion before jumping in with both feet.

I also love the concept raised in the earlier comment by Tawra (#10) about diversifying your income stream. Although it didn’t turn out to be the right situation the concept of diversifying income helps a lot when launching a passion. This means your passion doesn’t have to 100% support you on day 1.

Thanks.

Jeremy

Tracy
Tracy
10 years ago

I loved this article. I completely agree with everything you said. 5 years ago I decided to follow my ‘dream’ of being a self employed personal trainer. I tested it out on evenings and week-ends while I still worked full time in a finance role at a large company. Over the following 4 years, I slowly worked from full time at my corporate job, down to 2 days a week, and then finally realized I needed to make the ‘leap’! It was the most liberating feeling the first time I said “I’m a self employed personal trainer” and knew that… Read more »

Ryan
Ryan
10 years ago

Most “how to quit your day job” articles sell the dream without going in to detail about what is required. This is bad advice, because readers need to understand exactly what they are getting in to. Thankfully, this article avoided that hype. However, like most of the other articles on the subject I have read, the opinion expressed about those with a steady day job was subtly negative. It’s like you need to guilt us in to becoming an entrepreneur or something. To prove my point, I’ll quote you: “Chasing a dream isn’t for everyone. There are plenty of people… Read more »

Ash
Ash
10 years ago

@Rob (#12): I really like your comment and totally agree.

I also like the Sierra’s line “ a dream job is still a job “. That’s a really good point to remember.

Happy B-Day Sierra!

Barb
Barb
10 years ago

Its worth noting that many people LIKE their so called regular jobs, and not everyone has the dream to quit-lots of people dont fall into the “whose never dreamed”. Many of us choose our careers because thats what we really wanted to do, after all. Its also worth noting, that its much easier to quit that job and play a bit when one as a spouse who is keeping the regular job. Im going to assume that Sierra got to take her leap because her hubby is willing for whatever reason to stay at the job he is in, regular… Read more »

Tyler Karaszewski
Tyler Karaszewski
10 years ago

Online finance writers constantly caution about stocks as being risky, yet advocate starting your own small business, which is much riskier. We saw caution about stock risks here on GRS as recently as yesterday, but today the only caution in this article about starting your own business is that you might not like it. I have a story that’s not unique. A woman I know started her own business. She was divorced, and so was doing this on her own, she didn’t have a spouse’s income to fall back on. To open her store she needed some investment money —… Read more »

Tyler Tervooren
Tyler Tervooren
10 years ago

Way to go Sierra. I saw your interview over at IWTYTBR and it all rang very true.

Solid advice for anyone playing the “Is it time yet???” game.

Kent @ The Financial Philosopher
Kent @ The Financial Philosopher
10 years ago

I enjoyed this article, Sierra.

No matter who you are or where you work, however, the first goal to accomplish is to have a healthy relationship with the present moment.

If quitting the day job is a means of doing this, great. But if you are not able to find contentment now, it is possible you won’t ever find it.

Chasing dreams is not unhealthy but it can keep you far away from now.

“Every one rushes elsewhere and into the future, because no one wants to face one’s own inner self.” ~ Michel de Montaigne

Ely
Ely
10 years ago

To answer your question, me. I don’t dream of quitting my day job. I’m not a writer or an artist or an entrepreneur, and I have no desire to be. I’ll keep my steady 9 to 5 with benefits and a raise every year, thank you VERY much, and I’ll leave it behind me every day when I leave the office and go live my life – the life made possible by having a steady job.
Also, I love the double-take people do when I tell them I’m an accountant. I guess I don’t fit the stereotype. 😀

Tami
Tami
10 years ago

My husband opened a restaurant 6 years ago (after being in the business of managing restaurants for over 15 years). The first few years went fine. He didn’t make much more money that he was making managing restaurants, he worked crazy hours, but he loved it and the business was doing OK (able to meet all business obligations). When the economy started to go down the business tanked. Things went very bad very quickly. We went through all savings, got behind on business taxes, and there were many months when he could not pull a paycheck at all. If I… Read more »

Money Reasons
Money Reasons
10 years ago

Congratulations on taking the leap!!!

Great job identifying the critical elements needed to make the jump for us non-jumpers! 🙂

Nancy L.
Nancy L.
10 years ago

Tyler, excellent reply. When I was a child, my mom started a business with two other women. The financial and emotional shadows that were cast upon our family as a result of the eventual failure lasted for more than a decade, and I would not wish those experiences on anyone. Ironically enough, the problem her business faced was being ill-prepared to handle success–all three partners had weaknesses that didn’t mesh well together, and the larger their business got, the more the weaknesses caused problems. What I took away from witnessing the failure first hand was that you need to be… Read more »

Christina in NM
Christina in NM
10 years ago

I have to agree with Tyler. While I find these types of articles inspirational,I think they’re incomplete. Yes, it’s awesome to have a “dream job” but I think the reality of life is that work is, well, work. Sometimes your job is wonderful, sometimes it’s awful regardless of whether it’s your passion or not. Also, self-employment seems really limited. Who is going to be a self-employed biochemist? There are a lot of jobs where you rely on the support of a larger entity, such as a company or university, and striking out on your own is just not possible. Many… Read more »

Nate
Nate
10 years ago

A couple things: – Sierra, your interview @ IWTYTBR was fantastic – I really enjoyed it. – Those of you who are saying that starting a small business is super risky – you are missing an important part of the article. Start SMALL – while you have your day job. Find out if you like doing it as a business and IF IT CAN MAKE MONEY. If you can grow revenue to a point that meets your needs and some of your wants, then take the jump out on your own. This scenario is much less risky than just jumping… Read more »

Budgeting in the Fun Stuff
Budgeting in the Fun Stuff
10 years ago

Happy Birthday! I don’t hate my day job, but it is mediocre at best. I LOVE BLOGGING. Love it. Love the writing. Love the commenters. Love the spam (yes, it makes me smile that my spam has picked up). Love the ad negotiations. I love blogging. Until my blog brings in enough to replace what my salary provides, I’m going to do both. Stick with my mediocre job with benefits and enjoy blogging everyday…even when I’m tired or an advertiser turns down my rate…I figure that this balance may not be the pure happiness equation, but it offers me stabilitiy… Read more »

KarenJ
KarenJ
10 years ago

It is very often easier for women to start their own businesses, as they have husbands working and bringing in a steady paycheck, and maybe they bowed out of the work force for a while to raise children, so it’s a natural fit to have that work/life balance. I attempted a business when I lost my semi-full time job in March of 2007. When my husband also lost his job a couple of months later, it was decided (by both of us) that he would pursue his dream of being a commercial realtor, and I would bring in the steady… Read more »

Lefty33
Lefty33
10 years ago

@ Tyler K- Excellent post, it truly is 100% the truth.

Way too many posts on this site about this topic make it sound way too free and breezy and most definitely cut out the details and any explanation about the likelihood that your business will fail and what to do when that happens.

J.D. Roth
J.D. Roth
10 years ago

Lefty33 (#36) wrote: Way too many posts on this site about this topic make it sound way too free and breezy and most definitely cut out the details and any explanation about the likelihood that your business will fail and what to do when that happens. Well, that’s not true. I’m well aware of the risks involved with running your own business. I come from a long line of entrepreneurs, and I’ve seen businesses fail all the time. When I write about this subject, I temper it with a dose of reality. But just because you might fail at something… Read more »

bethh
bethh
10 years ago

Thanks for the sobering balance, Tyler. I agree that for us Americans, health insurance is a major factor to consider when thinking about leaving employment for any reason (which I find super depressing). Since I’m single and don’t have a fallback support system, or access to someone else’s benefits, it seems almost lunacy to quit employment. Fortunately I’m one of those who is willing to put in a 40-hour workweek for someone else, am reasonably well paid, and love walking out the door at 5 with nothing stressing me out. I am not sure I believe the stat quoted above… Read more »

chacha1
chacha1
10 years ago

Some personal experience to share. DH worked in the rehab department at a very famous university hospital for fourteen years. At the end of that time, despite having qualified for and received a Physical Therapist Assistant license, he was only being paid $14/hr. After we were married, he decided to strike out on his own. He got a high-quality Personal Trainer certification and went freelance as a therapist and trainer. Within a year, thanks to his connections and client referrals – he has never advertised a day in his life, a good network is ESSENTIAL – he was making twice… Read more »

Tawny
Tawny
10 years ago

Great post! This is something I daydream about quite often, and it’s good to consider the reality of it.

Kevin
Kevin
10 years ago

I totally agree with Tyler K. I’m glad someone said it. I think most of these “entrepreneur” articles feature a little too much “it’ll-all-work-out-somehow”, and not enough “4-out-of-5-businesses-fail-within-5-years.” What is it with Generation X being so terrified of work? Why does everything have to be about “fun” and “passion” all the time? A little hard work builds character and self-discipline. You don’t have to look far to find stories of people who took a shot at their “dream” and either failed (leaving behind a trail of ruined credit, foreclosed homes, and decimated life savings), or found it wasn’t all they… Read more »

Lefty33
Lefty33
10 years ago

“Well, that’s not true. I’m well aware of the risks involved with running your own business. I come from a long line of entrepreneurs, and I’ve seen businesses fail all the time. When I write about this subject, I temper it with a dose of reality.” Sorry J.D. but it is true. While I’m sure that you are aware of those risks the dose of reality that you attempt to convey, IMHO, is usually not strong enough and the posts from your staff writers (like this one) convey even less. “But just because you might fail at something doesn’t mean… Read more »

Jessica
Jessica
10 years ago

Congratulations to Sierra on taking a big step. I’m glad she is getting what she wants and am happy for her that she is enjoying the fruits of her years of self-discipline. I think it is important to recognize that some careers lend themselves to self employment more than others – graphic design, writing, etc. come to mind. One thing most of these careers have in common is relatively low pay when you are working for someone else and low start-up/costs of entry. So quitting the day job represents less of a risk than it might for someone making $100k… Read more »

Nicole
Nicole
10 years ago

I thought this post was a lot more measured than previous posts on this kind of risk taking, for example the “informational interview” post by April last week… where I got slammed by some of the commenters for discouraging people from following their dreams. (Note, informational interviews ARE great for gathering information… but sometimes the naysayers have good information too.) Maybe it’s because I see Sierra outlining the steps in the way that Your Money or Your Life does, so when I read it I’m also thinking about what YMoYL recommended for following your dream as a measured risk. She’s… Read more »

Gregg Pechmann
Gregg Pechmann
10 years ago

Ok…I have been self employed ever since I left college in 1992. Started a manufacturing business with some success, got bored with it because it wasn’t my passion. Started real estate investing and then took the leap into the mortgage business …..and was extremely successful…made high 6 figures with the business and and high 6 f…igures with investing……only to see it all come crashing down (check out my meltdown in 2007: http://www.pechmanncoaching.com/about/my-story) I picked myself up, kept the family together (and NO, my wife was not working), and started over again in the mortgage business to again make 6 digits… Read more »

Money Smarts Blog
Money Smarts Blog
10 years ago
Where in the article does it say “quit your job and follow the rainbow”? The post I read suggested doing the business on a small scale and part time so that you can see if it is a good business and if you enjoy it.

Yes, that advice probably doesn’t apply to a capital and time intensive business like a restaurant, but it certainly applies to many situations.

Dave
Dave
10 years ago

I have a side repair business that I thought for awhile could become my main source of income and I could quit doing full time accounting work every day. I was looking for an escape from my day job. I’ve since found that I prefer to keep the side business small/under control and pick up a new customer by word of mouth every once in awhile. This arrangement lets me spend time with my kids in the evening whenever we want as opposed to me feeling trapped in yet another job. I also can spend time learning guitar. Oh sure,… Read more »

Amanda
Amanda
10 years ago

Christina in NM: I eat a plant based diet. No cheese/beef is healthier for you anyway. =) Overall I see a lot of negative comments toward Sierra. You must all admit she says you need a supply of cash for your known expenses. I think one of the posters that said it should be enough for one year. It should be more especially if you’ve got to put cash up for risk… Maybe if you have to take out a loan it’s not a good idea… I feel I have the best of both worlds. I have a job I… Read more »

Amanda
Amanda
10 years ago

Nicole, I do think that people have to guard against hearing what they want to hear from anyone they interview!

SLCCOM
SLCCOM
10 years ago

What troubles me is that while I do see mention of health insurance I don’t see anyone mentioning the crucial need for disability insurance. What will happen to Sierra if she has a stroke and can’t write any more? How will the family fare if the serial entrepreneur can’t work any more, particularly if the spouse has no ready job skills?

Go for your dream, but do it with your head screwed on straight!

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