Why I’ve Quit My ‘Dream Job’

“Are you sure this is what you want?”

I had just revealed to my boss that I needed to make a change and I was planning to start looking for other jobs, but his question really caught me off guard.

Up until that moment, I had felt one hundred percent confident in my decision.

It had taken me several weeks to work up the courage to start that conversation, but it took mere seconds to tear my wall of bravery down.

My voice was trembling and I choked back the tears as I murmured, “I don't know.”

There was a brief moment where I changed my mind and desperately wished that I could take it all back – the phone call, the conversation, my desire to leave.

But this was what I needed, even if making the change terrified me.

How did I know?

For at least five years it was a fantastic job, a dream job, and right for me in many ways.

No matter how much you may love something, it's important to recognize when it's no longer right.

Additionally, I felt that I was moving in a different direction professionally. I wanted to pivot my focus toward digital marketing and technology, neither of which are a priority at my company.

It was truly the perfect storm of reasons to leave a job, even if the thought of leaving the company I had spent most of my twenties with scared me.

Tough decisions

Approximately one week after telling my boss that I wanted to leave, I decided to give my two weeks notice.

I decided that what I truly needed was a break.

While I had already been offered another job, and had been in conversations with two other companies, I really needed some room to breathe.

I recently shared why job burnout no longer scares me.

I'd be lying if I said that thought of no longer having income after August 8th doesn't freak me out, but I know that this is the right decision.

What's next?

I'm going to spend a week in Massachusetts with my family starting on Wednesday.

After that, I'm not entirely sure.

My priories are leaving on good terms with my co-workers, finishing as much as my work as possible, and finding a way to share the news with the hundreds of people I've done business with over the past seven years.

While I'm not expecting to stay unemployed for long, I'll be sharing my strategies for coping financially during this this transitional time in the coming weeks.

I'm confident that brighter times are ahead.

Readers: Have you ever been unemployed? How did you handle the transition between jobs?

Like what you've just read? Stay on top of Cashville Skyline by following me on Facebook, twitter, Google+, and Pinterest!

Related Post


Discussions — 70 Responses

  • Tonya@Budget and the Beach July 28, 2014 on 8:22 am

    Wow big decision! I hope everything works our great for you! I left jobs before without having another one, but it was a different time (in the 90’s) where you could always easily get temp work of find another job very quickly. Not sure what it’s like now. Of course I wish you nothing but the best and hope you get some rest and some relaxation!

    • Addison Cash Tonya@Budget and the Beach August 1, 2014 on 9:00 am

      Thanks, Tonya. I am at my folks’ house relaxing right now 🙂

  • Stefanie @ The Broke and Beautiful Life July 28, 2014 on 8:44 am

    Unemployment has never really freaked me out because it’s part of the reality for actors. Every job we get is only a few months long- if that, so it’s only a matter of time before becoming unemployed once again. I’ve always been optimistic, which it seems you are too, and that’s really all I’ve ever needed. Everything really does work itself out when you are taking smart actions.

    • Addison Cash Stefanie @ The Broke and Beautiful Life August 1, 2014 on 9:03 am

      Thanks for sharing this, Stefanie. That’s a great point. Your positive attitude has undoubtedly helped you through all of these transitions.

  • Kassandra July 28, 2014 on 8:49 am

    Congratulations on decided to follow your instincts Addison. That takes courage.
    I have been where you are. I did the same by actually taking an entire summer off. When I did resume my job search I was quickly offered three positions and I choose the one that was the best fit for me. I never regretted that decision. As a result of taking that initial position and through various opportunities, I transitioned into a new career and being happy with where I am now.

    • Addison Cash Kassandra August 1, 2014 on 9:09 am

      Wow, a whole summer off sounds amazing. I haven’t done that since I was thirteen. Thanks for sharing your story. It’s great to hear that everything worked out well for you.

  • Shannon @ Financially Blonde July 28, 2014 on 8:55 am

    Congrats for having the “balls” to make a big leap like this!!! I did something similar with my first job where I told my boss I was leaving without knowing what I was going to do next. He actually took the news surprisingly well and helped me secure my next job in the city where I wanted to move. Leaps like this are scary as all get out but really help you grow in so many unexpected ways.

    • Addison Cash Shannon @ Financially Blonde August 1, 2014 on 9:12 am

      Hahaha, thanks Shannon! In this situation being honest and upfront with my boss was absolutely the best decision. Thanks for sharing your story!

  • Natalie @ Financegirl July 28, 2014 on 9:40 am

    Congratulations! It sounds like that although this was a tough choice, it was the right one. What a huge step – congrats again. Personally, I was unemployed after I took the bar exam for about three months. I knew I would get hired, as it is a common in between time for recent law school grads. I can’t imagine being unemployed for long. I always find a way to make money one way or another.

    • Addison Cash Natalie @ Financegirl August 1, 2014 on 9:13 am

      Thanks, Natalie. Yes, I’m not expecting to be unemployed for long. First, because I enjoy working. Second, because I like making money.

  • Kipp July 28, 2014 on 10:01 am

    I hope all works out well for you Addison! I only had a brief less than a half year period during college that I was not working. I did not desire to get a job somewhere only to quit in 3-4 months as I expected to have an internship lined up for the winter (and I did get one lined up). Looking back I probably should have tried to get employment during that time, but it was fun and the only time since I turned 16 where I was not working for a period of time (or have something lined up directly afterwards). It made me a bit nervous at first, but it was enjoyable to be able to just spend time on college and with my then Fiance (now wife).
    But, with that said, you need to do something now that you can live with while trying to reach FI. I would imagine my FI life would be something like that period where I did not work for 3-4 months, but still work on doing something productive (but maybe not full time 🙂 )

    • Addison Cash Kipp August 1, 2014 on 9:15 am

      Great point, Kipp! It’s definitely important to have a livable job while working toward financial independence. Great reminder.

  • Income Surfer July 28, 2014 on 11:14 am

    I hope things work out great Addison. I’m glad you assessed your situation and decided it was time for a change. Many people get up every morning going to the same job they hate, just because they did the day before. About 5 years ago, I stayed at an engineering job too long. I loathed it, and it was very unhealthy. You’d never believe how much better I felt when I left.

    I’ve been unemployed three times, in a 4 year period actually, and it’s never fun……but if you embrace your new possibilities/flexibility it doesn’t have to be bad. Best of luck!

    • Addison Cash Income Surfer August 1, 2014 on 9:16 am

      Thanks, Bryan. I’m feeling extremely optimistic. Thanks for sharing your journey.

  • Andy@artofbeingcheap July 28, 2014 on 12:21 pm

    Wow! That is something. I haven’t been unemployed in so long I really don’t remember what it is like, so I will just wish you good luck.

    • Addison Cash Andy@artofbeingcheap August 1, 2014 on 9:17 am

      Me either, Andy. Thanks for the kind words!

  • Debt and the Girl July 28, 2014 on 12:36 pm

    Wow! You have got guts, girl! I hope you get what you are looking for and that you will find something great. Good luck to you!

    • Addison Cash Debt and the Girl August 1, 2014 on 9:18 am

      Thanks, lady! One week later, I’m feeling really good about my decision.

  • J. Money July 28, 2014 on 12:45 pm

    Wow, that’s pretty ballsy indeed – especially without having something lined up? I took the plunge myself years ago but I was also a) planning on the next step for months to come and b) fired – thereby forcing me to do what I truly wanted, haha…

    Either way, big changes like that are always exciting – so hope your next one is even better, brotha!

    • Addison Cash J. Money August 1, 2014 on 9:21 am

      Thanks, J. I really appreciate the encouragement! It’s an exciting time.

  • Ryan @ Impersonal Finance July 28, 2014 on 1:24 pm

    Ahhh! I’m glad to see you did it. I’ve been unemployed, but never on purpose, and I never had a plan to deal with it. Enjoy Mass, and like you said, I’m sure you won’t be unemployed for very long. Congrats 🙂

    • Addison Cash Ryan @ Impersonal Finance August 1, 2014 on 9:22 am

      Thanks, Ryan! Me too! Once I made the decision to quit, I knew I had to take the plunge. Thanks for the encouragement.

  • E.M. July 28, 2014 on 3:48 pm

    Congratulations on making the leap! I’m sure there are good things ahead for you. I think it’s great you’re taking some time to breathe and spending it with family. The few times I’ve chosen to leave jobs, I made sure to have hefty savings just in case. The transition can be a challenging one, but it sounds like things will fall into place for you soon. Best of luck!

    • Addison Cash E.M. August 1, 2014 on 9:30 am

      Thanks for the support, E.M. My family has been majorly supportive of my decision and it’s great to spend a few days in Massachusetts. I’m looking forward to hitting it hard when I get back to Nashville.

  • Autumn @ The Barefoot Budgeter July 28, 2014 on 6:33 pm

    Wow, that is a big change indeed. Enjoy your break and the time away. I have a feeling you’ll be looking back on this in a few months and will be so glad you had the courage to make the leap. Cheers to new opportunities!

    • Addison Cash Autumn @ The Barefoot Budgeter August 1, 2014 on 9:32 am

      Thanks, Autumn! I hope that this is the case. It’ll be nice to feel relaxed and rejuvenated around the holidays instead of complete exhaustion from months of traveling.

  • NZ Muse July 28, 2014 on 7:08 pm

    Scary, but exciting! Congratulations and good luck. As someone who also left a dream job after a few years I very much sympathise. I feel the need to write a post about job satisfaction/happiness coming on (I seem to do one every other year or so…)

    We are also entering a transitional time as my husband is about to pull the plug on a nightmare job, here’s hoping it works out for all of us eh?

    • Addison Cash NZ Muse August 1, 2014 on 9:33 am

      Wow, it sounds like big changes are on the horizon for you guys! Best of luck with that. I’ll look forward to reading about it.

  • Dan @ Our Big Fat Wallet July 28, 2014 on 7:24 pm

    I think at some point it becomes no longer worth it, no matter what the expected future benefits are. Sounds like you have reached that point. Hope it works out for you in the future as Im sure it will. It’s a time of transition but a good one and it can be very exciting to know that anything can happen in the future

    • Addison Cash Dan @ Our Big Fat Wallet August 1, 2014 on 9:34 am

      Thanks for the encouragement, Dan. Transition can be scary, but it’s also good.

  • Dividend Mantra July 28, 2014 on 7:58 pm


    Sounds like you thought long and hard about this, and it was something that was bothering you. So it’s the right thing to do.

    I quit my job in the auto industry paying more than $50k per year a few months ago, and I couldn’t be happier. Though, I already had my next move (writing, investing, moving back home) lined up. You’re kind of winging it, which sounds fun! 🙂

    Wish you luck. And I hope you get some much-needed R&R in!

    Keep us updated.

    Best wishes!

    • Addison Cash Dividend Mantra August 1, 2014 on 9:36 am

      Thanks, Jason! Your journey has continued to inspire me. Especially with the decisions you’ve made regarding family. Thanks for the support. I’m feeling optimistic.

  • femmefrugality July 28, 2014 on 9:19 pm

    Best of luck! It can be scary, but sometimes we really need that change. I’ve only ever been unemployed for a couple of months at a time. A couple of them I had planned for and had adequate savings. Once I got really sick and couldn’t keep my job because of it. That was awful. But I think if you’ve planned for it things will turn out well. 🙂

    • Addison Cash femmefrugality August 1, 2014 on 9:28 am

      Thanks for sharing your story and the reminder than unemployment can occur at any time for a variety of reasons. It’s important to remember this when building an emergency fund.

  • Melissa July 28, 2014 on 9:39 pm

    Wow, best of luck to you! It really sounds like you did need to leave the job, and you left for the right reasons. Another door will open for you, and I’m sure you’ll find another ‘dream job’ soon. I’m rooting for you no matter what path you pursue! 🙂

    • Addison Cash Melissa August 1, 2014 on 9:26 am

      Thanks so much for the encouragement, Melissa. I really appreciate the support.

  • debt debs July 28, 2014 on 10:20 pm

    Best wishes, Addison. I hope that you find something meeting more of what you are looking for. I’m surprised and not surprised, but needless to say it takes a lot of courage or possibly just being really fed up.

    • Addison Cash debt debs August 1, 2014 on 9:24 am

      Thanks for the kind words. Life is too short to continue traveling down the wrong path for too long.

  • Kate @ Money Propeller July 30, 2014 on 5:01 am

    I hope the best for you and I know that you made a good decision. My hubs also talked to me that these past few days he doesn’t feel like working, it’s hard for him to go to work every day. He wants to resign, but his boss asked him to stay.

    • Addison Cash Kate @ Money Propeller August 1, 2014 on 9:23 am

      Thanks for sharing your story, Kate. I’ve definitely felt a similar loyalty to my company, boss, and co-workers, but ultimately, I had to do what was best for me.

  • Have You Calculated Your Bare Bones Budget? | Cashville Skyline Have You Calculated Your Bare Bones Budget? | August 1, 2014 on 5:02 am

    […] many of you now know, I’ve recently quit my job. While I’m not planning to be unemployed for long, I’d be lying if I said I’m not […]

  • Michelle August 3, 2014 on 1:21 am

    I think that you have to trust your gut. There’s a point when you just have to do what’s best for you, take a leap of faith, and move on. I think that being optimistic vs. pessimistic also will also play into how you move forward. What an adventure. Go out there and kick some a@@!

    • Addison Cash Michelle August 3, 2014 on 12:19 pm

      Thanks for the support and inspiring words, Michelle! You are totally right!

  • US expat August 5, 2014 on 2:34 pm

    I would recommend this to everyone – save up so you can take a 2 or 3 month sabbatical at least once a decade (whether that’s an unpaid break in your existing job or quitting and taking a break before starting new job). It happened to me once in my 20’s and I’ll never forget it. I was moving abroad due to marriage, so I quit my job in US with 3 months savings. When I arrived in new country, I spent a month job hunting. Found a job where they didn’t expect me to start for 2 months. So I had time off where I could live off my savings knowing a job was lined up at a certain time. My mental attitude starting the new job was incredible – I had so much energy too. The number of people I know that quit a job and start the next day or just after the weekend immediately are missing an opportunity of taking a complete break.

    • Addison Cash US expat August 5, 2014 on 9:45 pm

      Thanks so much for commenting and sharing your story! The mental break will be amazing.

  • Maintaining Your Network is More Important Than Saving Money | Cashville Skyline Maintaining Your Network is More Important Than Saving Money | August 12, 2014 on 5:02 am

    […] I knew that I would soon be leaving my job, I wanted people to […]

  • August Link Love, TSMCP Around the 'Sphere, Side Hustle $ And Hire Me :) | The Shop My Closet Project August 30, 2014 on 10:31 am

    […] Addison over at Cashville Skyline also let’s us know Why I’ve Quit My ‘Dream Job’ […]

  • The Career Pivot: Taking a Step Back To Make a Leap Forward | Cashville Skyline The Career Pivot: Taking a Step Back To Make a Leap Forward | September 1, 2014 on 5:00 am

    […] colleagues, friends, and family members were shocked to learn that I had suddenly quit my job. I had dedicated years to reaching a certain level within the company and my career. For many, the […]

  • I quit my job now what November 11, 2014 on 4:18 am

    I get impressed from you. Not only job family is also important. Whenever you are in problem your company and boss will not come to help you. Your family will help you at difficult condition. So take a time for family.

  • Best Career Change Ideas November 26, 2014 on 1:14 am

    Qutting the job is not a bad idea. If you want to know Best career change ideas then visit “I quit my job now what”

  • Young Professionals Need a Side Hustle | Cashville Skyline Young Professionals Need a Side Hustle | December 9, 2014 on 5:06 am

    […] At the borderline geriatric age of 30, I’ll openly admit that my energy level is not quite as robust as it was in my early twenties. This has led to many recent lifestyle changes, including a career transition. […]

  • Losing My First Job Was The Best Thing To Ever Happen To My Finances | Cashville Skyline Losing My First Job Was The Best Thing To Ever Happen To My Finances | January 12, 2015 on 5:05 am

    […] protected myself from layoffs or burnouts by consistently living below my means, saving as much money as possible, and now, adding side […]

  • Holding Myself Accountable: the (Belated) July Review - Cashville Skyline Cashville Skyline Holding Myself Accountable: the (Belated) July Review - Cashville Skyline | April 11, 2015 on 4:38 pm

    […] After alluding to upcoming career changes by stating that I no longer feared job burnout and metaphorically comparing myself to the overgrown succulent living in my bathroom, I quit my job. […]

  • Why Personal Savings Rate is Important - Cashville Skyline Cashville Skyline Why Personal Savings Rate is Important - Cashville Skyline | May 20, 2015 on 9:18 am

    […] It took me several months of saving 40-50% of my income to reach a point where I felt comfortable quitting my last job. […]

  • #MoMoneyPodcast Launch & Giveaway! - Cashville Skyline Cashville Skyline #MoMoneyPodcast Launch & Giveaway! - Cashville Skyline | June 3, 2015 on 5:03 am

    […] know, I studied music in college, worked a concert promoter for several years, and strategically quit my job last summer. Six months ago, I started a new career in digital […]

  • Is Our Definition of Overtime Absurdly Low? - Cashville Skyline Cashville Skyline Is Our Definition of Overtime Absurdly Low? - Cashville Skyline | June 8, 2015 on 5:01 am

    […] probably didn’t surprise anyone when I got burnt out and eventually quit my job. However, it took a recent hourly side hustle to highlight the importance of protecting my […]

  • How I Earned an Extra $10,681.71 This Year - Cashville Skyline December 15, 2015 on 5:03 am

    […] year, after I quit my career as a concert promoter, some friends recruited me to work part-time with the coolest ticketing […]

  • What Does Financial Freedom Mean To You? - Cashville Skyline December 20, 2015 on 9:36 am

    […] my inevitable job burnout came last summer, I was able to quit my job and recharge for a few months while transitioning into my new […]

  • Cashville Skyline Turns One! - Cashville Skyline December 20, 2015 on 9:52 am

    […] read about some major life moments: losing a friend to suicide, quitting my job, attending FinCon under my real name, starting a new part-time job, attending weddings, traveling […]

  • My Dividend Portfolio is Working Full-Time Even When I'm Not - Cashville Skyline December 20, 2015 on 10:47 am

    […] many of you know, I quit my job last month and I couldn’t be happier with my decision. I snagged a sweet part-time gig after […]

  • Why Is Talking About Money The Last Taboo? - Cashville Skyline December 21, 2015 on 1:50 pm

    […] to my recent change in employment, I intentionally allowed everyone to think I earned a very low income. Despite receiving several […]

  • Roundup From the Road - Cashville Skyline December 21, 2015 on 2:16 pm

    […] Why I’ve Quit My ‘Dream Job’ […]

  • Financial Samurai February 14, 2016 on 7:25 pm


    I missed it, but what was your dream job? And how long were you working it?

    I found my dream job right outta college and lasted for 13 years. But I burned out after about year 10-11.


    • Kate Dore Financial Samurai April 10, 2016 on 9:54 pm

      Thanks for reading, Sam! I worked as a concert promoter for most of my 20s. It was amazing for most of that time, but I realized it wasn’t a long-term sustainable career path. And my body really needed me to get off the road. Sounds like we had similar burnout timelines 🙂

  • How I Made $2,228.55 Side Income This Quarter - Cashville Skyline April 11, 2016 on 7:28 am

    […] burning out in my previous career and from too much side hustling, I’ve grown fiercely protective of my time. And even with […]

  • My Ninth Net Worth Overshare - Cashville Skyline June 19, 2016 on 11:59 pm

    […] you may remember, I emptied my savings account after quitting my job in August 2014 and I’ve been slowly working on rebuilding my emergency fund since January […]

  • Free Money Resolutions Course - Cashville Skyline January 8, 2017 on 7:14 pm

    […] to save 45-50% of everything I earned for over a year. Getting my finances in order helped me quit my job and change […]

  • Side Hustle Your Way Out of Debt - Cashville Skyline January 24, 2017 on 5:01 am

    […] For me, financial freedom was the ability to quit my dead-end job. […]

  • My Favorite Free Budgeting Spreadsheet - Cashville Skyline February 16, 2017 on 6:04 pm

    […] used it to quit my job, change careers, and survive a […]

  • What’s Your Story on The Road to Financial Wellness? Part 2 - Phroogal August 18, 2017 on 3:37 am

    […] saving between 40-50% of earnings. When my inevitable job burnout came last summer, I was able to quit my job and recharge for a few months while transitioning into my new […]


This site uses Akismet to reduce spam. Learn how your comment data is processed.