How to Quit Your Job – 5 Steps to Transition Into a New Career

While travelling in Dallas for work, I picked up a book titled One Person/Multiple Careers by Marci Alboher. It spoke about how wearing many hats and not being tied down to a full-time job can work for you. In the first few chapters,I made an instant connection: There were a lot of people with dynamic careers out there in the world — just like me — who wanted to know how to quit their full-time job!

I’m a Corporate Banker/Real Estate Agent/Writer/Board Chair for my local Boys & Girls Club. For a long time, I was my biggest critic about these several slashes. I thought to myself, “Okay, Cat, you’ve proved that you can do a lot. . . now pick one. . . one!”

Then, after some further contemplation, I realized there’s absolutely nothing wrong with being the slash careerist, as long as maintaining health and balance were always at the center of my values: 7 hours of sleep; 6 days a week workout; quality time for family and friends; feeling good from the inside out.

There is a direct relationship with a healthy home life, as there is with a healthy career life. As long as these five are in check, my slashes are always thriving.

Maybe you’ve heard stories of people who just switch gears into another career – and they did it oh, so seamlessly. On the outside, it appears they went to sleep as a corporate rat-racer and woke-up as a successful entrepreneur.

Here’s the reality check – it typically doesn’t happen that way.

Usually, there’s some planning that has been bubbling behind the scenes.

More than ever, and more openly than ever, people work a full-time job to collect a paycheck and then part-time dabble with a passion that may eventually take over.

It took three years of toying with real estate on the side before I realized that the entrepreneurial spirit side of me really could embrace the industry as a full-time career, and provide the flexibility to spend more time freelance writing.

Now, I’m running with real estate faster than ever.

Eventually, I’d love to shed the corporate title and just have three slashes: Real Estate Broker/Writer/Non-Profit Volunteer.

A decade ago, working two careers might have seemed less than glamorous – but it’s no longer viewed as a second job or a slave-driving way to make ends meet; instead, it’s seen as a well-rounded fulfillment. A smart, secure Plan B. An alternate route to a more promising future.

How to Quit Your Job

If you’ve been contemplating switching careers by creating a slash, here are 5 steps to start the part-time gig and eventually replace your full-time career.

1. Start

“I don’t know what I want to do though,”is something I often hear from people who are unhappy with their full-time job. There’s this unwillingness to expand, be creative and explore, in order to uncover new possibilities; and this willingness to settle into the comfort, feel stuck, and repeat each day with the current, bland, monotonous circumstance.

Just start. Dabbling in an area of interest can often transform into a full blown opportunity.

My husband is in the education industry – his employer has been a great company to work for; however, he knows this is not his authentic expression or unique contribution to the world.

Instead of waiting for an epiphany to hit him one morning where he can discover his calling, he went about his weekend by being open-minded, trying new things, and meeting new people.

In the past two years, he became very involved with meditation – taking courses locally and out of state.

Recently, his meditation teacher mentioned to him a business opportunity with her meditation center. Perhaps this will blossom into something more. Or perhaps it’s still in an infant stage.

Either way, the point is this: When we whole-heartedly pursue our interests or participate in activities that foster our growth, the Universe is awesome in its return.

2. Set Incremental Goals

Now that you’ve found an inkling of what you may want to do, it’s time to upgrade it from hobby to a job or a entrepreneur venture by establishing a business plan with goals.

For example, maybe you want to become a Social Media Manager. Some incremental goals would be to reach out to 3 local businesses a week for the next two months to promote your Social Media talents to grow these small businesses.

Additionally, you might sign-up for a Twitter following of Social Media Gurus and Managers to stay abreast to the latest hot tech trends.

3. Surround Yourself with Industry Experts

Since I was a child, I loved writing. When I talked to my dad about become a journalist in college, he told me writers made very little money and it’d be a difficult living – and that instead, I should pursue business. So I did.

I went to school, graduated with a degree in Finance and became a banker.

Ten years into the industry, I realized that my first-love is still writing – and my fulfillment meant more than a nice, corporate paycheck – but I was clueless where to begin as a writer.

I put myself out there by finding self-development websites, a topic I feel passionate about. I started sending in blog submissions and eventually met Tina via Think Simple Now (also founder of WorkAwesome).

This meeting opened my online world to a brilliant circle of like-minded writers who I highly respect.

4. Get Your Finances in Order

Pay off the debt; simplify; take a giant chain saw to any discretionary expenses.

The transition from a regular bi-weekly paycheck to a more erratic cash flow will be much easier with zero debt and 6 months of insulation built into your savings.

In our bedroom, we have a white board with a thermostat. At the top of the thermostat are our savings goals by June 2012. Each time we pay down debt and fill the savings account, the thermostat goes up.

Maybe get a white board with your finances spelled out for you every morning, or perhaps just start with a household budget. Do what it takes to get your finances in order by keeping it in front of you daily.

5. Be Fearless: Quit the Job

Now you’re ready to take the leap. You’re become more and morebrave as you reach business goals and insulate your bank account.

The logistics are taken care of. But you’re scared – it feels new, it feels like change. You’ve become a bit hesitant leaving the comfy, familiar territory of paycheck collector.

The antidote to the creeping feeling of fear? Work on you, as you are the only possible obstacle and variable in the grand equation.

Associate with colleagues who have made a similar transition.

Surround yourself with people that are positive and passionate about living a life that is more extraordinary and authentic, and less ordinary and mediocre.

Reach out to a life coach to keep you on track.

Read self-development books, blogs, and podcasts that challenge the norm.

Then, go after it!

What are your thoughts on quitting your full time job to pursue something new? Share with us your stories and interesting thoughts in the comment section.

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Cat is a corporate banker, real estate agent, and writer who is passionate about well-being: mind, body and financial wellness. Add her as a friend on Facebook or follow her @Cat_Stevenson


  1. STRONGside on the 15th July

    Great post! I can identify with having multiple careers and using them all for fulfillment. I enjoy my full time job in Education. I love what I do, and I enjoy my co-workers. The hours are less than 40, and the stress level is manageable. However, my passion is also writing. I have done freelance writing for over a year now, and I have enjoyed every minute of it. So much so, that I am happy to get up every morning at 5am to write. That is my most creative and productive time. I would some day love to be able to write full-time, but before I take that leap, I am really enjoying the benefits of the dual career!

  2. Cat Li Stevenson on the 15th July

    STRONGside~ It’s great to connect with fellow slashers who also have a passion for writing, too!

    In speaking with other writers, having a dual career is a great option that counterbalances the writing schedule and solitude lifestyle. Sounds like your day-job is stress-free and quite complimentary to the freelancing.

    Cheers to your 5am writing and your leap when the time is right 🙂



  3. Tracy Antonioli on the 15th July

    Love this post! I’m good with numbers one, two, and four. I’m working on five–I ‘just’ took a year-long leave of absence. And number three is GREAT advice!

    I’m constantly surprised by those who say things like ‘I don’t know what I want to do’. I know so many things that I want to do–I just need to figure out how to make income from them. And I hopefully, someday, I will.

  4. PRANAB DASGUPTA on the 15th July


    1. Great post.
    2. It requires lots of courage and discipline to
    quit the present job and jump on to the profession
    where work comes from heart.
    3. In India some years back we have seen
    a movie “3 IDIOTS” which was on similar lines.

  5. Uzma on the 16th July

    Absolutely. Just coming to the same realization, that its okay to be Jack or Jill of many traders. Why box ourselves in ? Thats just societal conditioning . As long as we truly love what we do. We have so many facets and a list of values. Sometimes one role just doesn’t fit them all. As long as our true nature , in alls its hues is being expressed . The roles can be many and can even be changing. Thank you for this reminder !

  6. sue ritchie on the 16th July

    A great post 🙂
    I have recently taken the leap and changed careers, and did it very much in the same as you write about Cat.
    I started by doing a distance course…and that’s the important word; started.
    I agree, you have to make a start somewhere. Read a book/website/magazine, talk to someone…every small step is one in the right direction.
    I also saved some money to ease the transition, and used my past career skills on a part-time basis to supplement my income in the early months of establishing myself.
    As for industry experts – Twitter is brilliant for that!
    I love reading your posts 🙂 Thank you!

  7. Cat Stevenson on the 16th July

    Tracy~ It’s wonderful that you had the opportunity to take a 1-year sabbatical — what a gift! I’m a firm believer in whole-heartedly going after what you love to do, and the rest ($ included) will work itself out.

    Uzma~ Yes, it took me a few years to settle into my own multi-faceted skin.

    The book I mention in the article has several great stories of people from around the world with different hats. I believe that as long as our values (be it family, health or other relationships) are at the center, a compilation of meaningful work is always okay 🙂

  8. Cat Stevenson on the 16th July

    Sue~ What a great testimonial 🙂 Thank for sharing with us. Congrats to you on the graceful career change.

    Pranab~ I wonder if they have 3 Idiots here in the US. Maybe I’ll watch sometime.



  9. Peach on the 17th July

    Great insights. I am currently on a multiple slashes employment system where I have a full time job, master degree, web design freelance work and startups ( The article is right where I am now so this is very helpful.

    Thanks for the article. 🙂

  10. Swamykant on the 26th July

    Wow. I am too planning to quit my day and become a Freelancer soon. This is an interesting article to achieve the same.

  11. rosario montana on the 31st July


    great post. it has given me the courage to carry out what my first love is- writing.. have some money saved so i can take time off to strengthen and use this skill for about a year…thanks for the tips and the thoughts.. it is really a great upper

    • Cat Li Stevenson on the 3rd August

      Rosario~ Congrats on having the courage to pursue your first love 🙂 Best to you on your adventurous writing journey.


  12. Brigette on the 3rd August

    After having my hours cut to part-time at my job-job, I took it as an opportunity to really pursue my goal of freelancing for a living. I’m scared at times, but pursuing with passion has allowed me to find some great freelance work that is helping me stay afloat financially. I am beginning to see and feel that “what I truly want” is doable.

    Your article is great reinforcement.



  13. SB @ One Cent At A Time on the 23rd August

    This is the way I quit my jobs, three in the past 5 years.

  14. sally on the 24th June

    I have been tinkering with steps 1 – 4 but Number 5 is the toughy. Maybe I need to believe in myself more. I know my dream and I completely believe I can do what I want to do… Finances are good right now and full time work has reached an impossible point right now where it should make it more easy for me to leave. But if that is so, why am I not doing it already? Step 5. Also I am worried I will let my family down if it doesnt work.

  15. Lola on the 13th August

    Great blog! I’ve been a slasher for as long as I can remember. I have always had SOMETHING that I was passionate about, even as I collected paychecks that at first seemed to be in line with my “true purpose,” but then I discovered the entire atmosphere of desk jobs, with someone ELSE being my boss just wasn’t for me. It took me many years to get to the point of realizing I don’t want to work for anyone else, I want to work for me! I’m a yoga teacher/music producer/writer/social media manager/webmaster/SEO-SEM-PPC specialist, and probably a few other things in there (oh yah, thai massage therapist, holistic health coach). I don’t have a husband or a rich family so financially, doing this transition is all on me! Consequently, I’m scared, but I’ve been saving money, reading books & articles (like this one) about making the transition, talking to EVERYONE about it and that I am going to do it, and figuring out a way how I can ask my job to go to part-time, so I can maintain some security while taking the big plunge. This is my next step: ask to go part-time. I feel like desk jobs are mostly soul-sucking enterprises…unless you’re really fortunate to work in a cool place with cool people. In my 15+ years working in Corporate America, I’ve realized most people are as miserable as you are going to their cube every day…and this is probably why working in these places is so unsatisfying for many.

  16. Michael on the 31st August

    fear is a natural emotion but you should never let it take over. I completed my undergraduate studies in 2008, worked for a networking firm here in Kenya with great pay for 2.5 years while always pursuing my interest in white and blue collar business on the side. eventually I won a grant to develop a software and left work as a network engineer to manage my software development firm with a relative of mine. things didn’t work out and by June last year we parted ways and I started a new firm with my partner who is also unemployed. she is great at sales and she is in charge of marketing. we have 2 young kids and business is rather slow for now. point is, never allow yourself to regret anything try your best and venture into what you want in life. challenges will always be there but you get fulfilment from knowing you can always face your fears. I hope to enrol in a masters course in computer science to increase my knowledge in software development early next year in the USA. luckily the course focuses on academia in the first eight months then allows me to work full time for 2 years while earning. If I can make it this far with all my responsibilities then everyone out there looking for self employment should.just aim at your goal and attack relentlessly. I will do it and I know you shall too!

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