Quitting my Day Job: Being Ambitious vs. Being Realistic

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4 min read

I currently have three income streams:

Dividend income.

Blogging income.

Day job income.

The dividend income is a real beauty. Each month I receive dividends in my brokerage account without doing anything to earn them. Even better, the companies that pay me these dividends often increase the payments each year. This income requires no time commitment on my part.

The blogging income is a complete joy. If I made zero dollars per month from this site I would still sit down and publish an article each day. I look forward to waking up early and writing something to share with the world. The fact that I make any money from blogging is almost too good to be true. This income requires time commitment, but I love doing it.

The day job income is the most bland of these three. It’s not a real beauty. It’s not a complete joy. This income requires a time commitment and it’s not something I love.

One of the greatest feats a human can pull off is earning income solely from doing stuff they enjoy. I haven’t quite reached that point. Two of my income streams are wonderful. One of them is not. 

Thus, I’m on a mission to replace my day job income.

The Nature of Corporate America

When I started my first job out of college I genuinely had a blast. I learned an incredible amount about Excel, programming languages, and analytical tools. My skill set grew by leaps and bounds each day. I was a learning machine. I felt like I was growing.

Unfortunately that growth didn’t last. After the first six months, I slowly stopped learning new skills and I had mastered all the analytical techniques that my job required. I stopped looking forward to going into the office. My projects stopped feeling like exciting adventures and started feeling like chores. I began to dread team meetings. I spent more time staring at the clock than I care to admit.

I needed a change. I needed to start learning and growing again.

Fast forward several months. I landed a new job with my current corporation. This same cycle began to repeat itself. The first few months I was a learning machine, picking up new coding skills left and right. Each day flew by. It was actually enjoyable. 

But in the past two months I have learned very little. I haven’t picked up new coding skills or pushed the boundaries of my knowledge in analytics. In fact, there have been fewer projects to work on and I haven’t felt needed. I have started to lose the feeling that I’m contributing to a bigger mission. This position is starting to feel like a job again.

I need a change.

My Love of Growth

I have come to realize that I love growth. When I’m growing – learning new skills, gaining knowledge, increasing my productivity – I’m happiest. Conversely, when I’m in a place where I have hit the upper limit of what I can learn, I become dissatisfied.

This is why blogging is so appealing to me. Blogging has no upper limit of growth. On any given day I can decide to create a financial app from scratch like this one. Or I can learn a new programming language and create an interactive visual like this. Or I can write an entire post in response to a comment left by a reader

I can pick and choose exactly what skills I want to focus on – writing, coding, SEO, design – and spend time creating something meaningful to share with the world.

I love having the autonomy and freedom to work on whatever I want. I haven’t experienced that feeling in Corporate America.

Mixing Ambition with Reality

This all leads to my current struggle: how to replace my day job in a smart manner. I can’t see myself working in a traditional 9-5 role at a corporation long-term. Instead, I want to be my own boss. The tricky part is figuring out when to leave my current job.

On one hand, I have the ambition to pursue a different lifestyle and branch away from a traditional job. On the other hand, I am trying to be realistic. 

In an earlier post this week, I explained that my apartment lease is up in nine months. This will be a pivotal moment when I will have to decide to keep my job or move on. If I do move on, I have to decide if I want to pick up another 9-5 job or become my own boss.

If I was 100% ambitious, I would become my own boss and live off a combination of dividends, blogging, and freelance writing. That’s the unicorn scenario. I would be able to earn money doing what I love while being my own boss.

If I was 100% realistic, I might instead stick it out at a corporation for another 8-10 years and become a millionaire. That would eliminate all my financial concerns, but only through sacrificing a decade of my life sitting at a cubicle.

I’d like to think there’s a way to blend being ambitious with being realistic. Thus, I have a plan.

My Tentative Plan

My end goal is to quit my day job in nine months and cover my expenses solely through income streams that bring me joy. It’s an ambitious goal, but a realistic one if I can do the following:

Increase my net worth to $100k or higher.

Increase my monthly dividend income to $250 or higher.

Consistently earn monthly blog income of $500 or higher.

Pick up freelance writing gigs to earn $500 or more each month. 

My future net worth and dividend income are actually fairly easy to predict. I should hit those goals over the next nine months. The blogging and freelance income goals are much harder to predict. If I can manage to hit all of these goals, there’s a good chance that I’ll quit my day job and work for myself. 

It’s hard to predict how this will all work out. Perhaps another work option will reveal itself. Time will tell.

I’ll let you know in nine months how this story plays out. 🙂


My favorite free financial tool I use is Personal Capital. I use it to track my net worth, manage my spending, and keep an eye on my monthly cash flow. It only takes a few minutes to set up and it makes tracking your finances simple and easy. I recommend trying it out.

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21 Replies to “Quitting my Day Job: Being Ambitious vs. Being Realistic”

  1. Dear Zach…don’t quit your day job….yet. We have been self employed since 1994. It is not for the faint of heart. You seem in a great position just not challenged enough. I would say that our number one expense thru all these years has been health care…and we are healthy! Please take a look at absolutely everything you are receiving from your employer. Talk with your higher ups about advancing or taking on new projects. How much money you make for your company will equal your value to them. Just showing up is not enough. Over the years we have been both employees and employers, owned rental property (still do), and anguished over our stocks during crashes. My number one advice: do not EVER use credit cards unless they are paid off each month. Appreciate your employer and help your coworkers. If you can’t …no joy…move on…but have lots of savings…it goes fast. Kate

    1. Thanks for the insight, Kate, I really appreciate it. You bring up a good point about all the benefits that come with working for an employer, healthcare being one of the most important. At the end of this nine months it will all depend on what type of income I’m earning outside of my current job…if I’m still only earning a few hundred bucks per month outside of my 9-5 it would be foolish to quit my job. But if I can ramp up my dividend, blogging, and freelancing income then my decision will become much more interesting.

      Thanks again for the advice, it’s great to hear the perspective from someone who is actually self-employed.

  2. Kate just provided you great advice. I concur, don’t quit your day job for a different reason; Timing.
    It’s probable the next bear market/flash crash/market top will occur or at least begin within 9 month’s, which is precisely when you want to quit!
    I have a distinct feeling that financial bloggers everywhere will be swept down the stream as most of them have very high equity allocations, having not taken gains nor raised cash.
    Take this advice, don’t quit your day job.

    1. Agreed with Kirk’s comments on Kate’s advice. Keep going as long as possible with your day job – especially with your current savings ratio. You’re going to make tremendous progress.

      As Kirk also mentioned, a downturn in the market at some point (no one knows when for certain) will come, and you’ll potentially be able to have opportunities that might not have been available if you quit your day job.

      Balanced Dividends recently posted:
      https://www.balanceddividends.com/landless-landlording-how-and-why-we-use-reits/

      1. It is tempting to stick with my current job for longer than just nine months because my savings rate is so high and I am building my net worth so quickly. I may very well stick it out for longer and continue to work on my side projects and side hustles in my free time, I’ll just have to see what position I’m in after nine months. Thanks for the feedback, Mike 🙂

    2. I appreciate the advice, Kirk. You bring up a good point – market prices are extremely high right now and a possible crash could be looming on the horizon. Then again, people have been saying that for the past three years as well. I will certainly keep that in mind once it comes time to make my decision, though.

  3. The idea that you could learn everything you needed to know about a job in six months makes me smile young one. I worked as an engineer for 38 years and barely scratched the surface of the universe of knowledge available in my field. I’m frequently retained as an expert in retirement because of my recognized and proven expertise but I still feel like a neophyte and am still constantly growing and learning. I worked from entry level to running the company and never once felt like I had mastered my craft. Now being self employed may well be your best option, but whatever you do don’t ever let your job limit your growth, that is an artificial limit. Striving to learn more than your job requires is what separates corporate drones from the people that win regardless of whether you work for the man or for yourself.

    1. Thanks for the advice, Steve. I certainly don’t think I have learned everything there is to know about my field in only six months, but specifically the types of tasks and projects I have been doing have been repetitive and all required the same skill set. I completely agree with you that I must take it upon myself to strive to learn more; I can’t just sit around waiting for a project to come along that challenges my skills. With that said, I have learned a ton about my field through this job and I am beginning to see what I do and don’t like about the job, so if I do switch roles I feel like I have a better idea of the type of work I would enjoy doing.

  4. Oh my gosh! I was just thinking about all this earlier today lol. It’s crazy how you leave a comment on my blog which leads me to your blog and this post. I too was thinking that I don’t feel challenged enough. When I started my current position two years ago, I was excited. I was learning new things I haven’t done before. But now that I have learned everything to do my job, it got boring.

    When I look at blogging. It’s an exciting challenge that I can’t wait to work on when I have the chance. The excitement never fades and I look forward to the possibilities that a blog could possibly bring me.

    I would love to have my blog replace my day job. It would be a dream come true that I hope to see one day become a reality. 🙂 Great post!

    1. I think many people feel similar about blogging – it’s just such a wide open field that has no limits on what you can do. I have found that it’s considerably harder than I thought to earn money from blogging, but fortunately I have fell in love with it so my main concern isn’t the money anyway. Thanks for the kind words 🙂

  5. Hi Zach, I came here to offer you some perspective. There are some jobs that are soul sucking but as we work more we realize that you need to find some aspect of the job that you are in agreement with. I am in the IT field but in another country and what I realize is that the sales fronting job is more exciting. the pre-sales, business development. the back office jobs after a while you might be able to figure out. most tasks are repeated.

    If you like to learn new things, it is likely you havent find a company that is hectic enough that the customer environment is dynamic enough to offer a challenge.

    Don’t think the other side is not without its challenges. there are some aspect of freelance work that you will know better when you go over the other side.

    There is also another option: get better and move up. You get to influence things and increase your remuneration.

    I am in the rough similar situation but closer to the end of the journey.

    I am in IT, my job nature has a lot of operations and repeated tasks. there are days that is a drab.

    I have divided income, blog income.

    You might be able to switch to be a tutor.

    1. Hey Kyith, I really appreciate your feedback.

      You said something that really caught my attention though – “If you like to learn new things, it is likely you haven’t found a company that is hectic enough that the consumer environment is dynamic enough to offer a challenge.” I think you may be right. Much of the work I am doing revolves around
      automating processes and I am more interested in building new models and implementing new ideas. I originally thought this role would have more innovative projects to work on, but that hasn’t been the case yet.

      I am also keeping tutoring in my back pocket as a potential way to earn more income. I’m keeping all my options open and continuing to work hard to grow my skill set so no matter where I choose to go in the future, I can earn a decent income.

  6. I think you will be wonderful at what ever you do. Why not after 9 months try to just live on other income and keep on working for 6 months and see if your estimates are good. This would mean busy weekends but you have tried and tested your assumptions.

    1. I appreciate the kind words, Subbu! I may try something similar to your suggestion, basically seeing if it’s possible for me to live purely off side hustle income. That would be a fairly safe approach. I may also stick around with this corporation for a couple more years to build up a cash buffer. My options are pretty wide open at this point, and I’m staying open-minded to all the possibilities.

    1. Haha it would be extremely early FIRE if I go through with it. My premise is that I actually enjoy working hard, just not necessarily for a corporation. So if I can quit my day job and still find ways to cover my expenses I would rather do so sooner than later. But I am also trying not to take my current position for granted because I am earning good money at a reasonable job.

      Also, I only started making money through blogging in the past 4 months or so…I have to admit it’s harder than I anticipated but it has been exciting to earn a few hundred bucks from doing something I enjoy so much!

      Thanks for the feedback, Lily 🙂

  7. I really enjoyed reading your article! Currently, I am bored with my job but I won’t quit for the same reasons Kate and Kirk mentioned above. Last Monday I interviewed for the IT department so I am hoping to get that position and learn new technology!

  8. With your lease being up, if you look to lease somewhere else or buy, they often want to see steady employment. Every aparment lease I’ve applied for they asked for my employer, and sometimes it got me a discount on the security deposit. That transition to entrepreneurship may not have enough data for them.
    My mom ran into a similar situation with retiring (a bit early), but her pension hadn’t started to pay out. Her house was taking a while to sell, but she needed to commit to the new house she was moving to, financially. Despite money in savings they didn’t want to give her a mortgage because she had no proven cash flow.
    ‘They’ in the field of psychology suggest not having multiple life transitions at a time if it can be avoided. Job change, moving out, ending a relationship, and a list of a few others. Of course a break up / divorce often also means moving out. I went through a break up, but didn’t move until I had a new job secured, but the triple issue combination wasn’t great.
    I also like to feel like I am learning new things at work, but I’m not a competitive shove someone else out of the way to get ahead person. I’ve found letting management know I’m up for whatever they have, works for me. With a coworker out, my direct boss on vacation and the next level boss having new responsibility we both learned a lot of new things last week. Having that I’ll get it done (first time I do it might take a little longer) and reliably performing I’ve found keeps that challenge coming. My bosses know they can give me almost anything and I’ll find a way to get it done.
    Best wishes in your decision and seeing how things evolve in the next few months.

    1. You make a great point about avoiding multiple big life changes at once. That can put you in a very difficult position. My ideal situation would be building up enough income outside of my day job to be confident in quitting and still being able to prove to an apartment complex / whoever else that I have steady cash flow each month. It’s tough to say where I’ll be in the next few months but I’ll be sure to share updates along the way. Thanks for the comment 🙂

  9. Hi Zach,

    I suggest you do not quit your job. You may want to consider changing job. A new job will possibly mean a bigget challenge.

    Ben

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