I Am 9 Months Away from Making Some Serious Financial Decisions

maldives.PNG
5 min read


“You can’t connect the dots looking forward you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something: your gut, destiny, life, karma, whatever.”

-Steve Jobs


Three months ago, I moved with a roommate into my first apartment. Nine months from now, our lease will be up, my roommate will be moving to a new city, and I’ll be faced with some very real and very tough decisions:

Do I stay in Cincinnati and keep my current job? Do I move elsewhere in the U.S. and get a new job? Do I abandon a traditional job altogether and focus on freelance work? Do I move somewhere overseas and attempt to be a digital nomad?

These are all possibilities for me. For the first time in my life, I have to admit that I don’t have a definite plan for the future. Yet, whether I like it or not, I have to make a decision once August 2018 rolls around.

Crossing $100k

Based on my current monthly savings, my net worth should cross the $100k threshold before August 2018, which will put me in a financially flexible situation. 

I recognize that $100k isn’t enough for me to be financially independent.  Yet, because I always plan on doing work that I find interesting, I don’t need to save up enough money to never work again. I’m not shooting for early retirement.  I just need enough money from a combo of passive and active income to ensure that I don’t have to rely on a traditional 9-5 job for income. 

Between my dividend income of $100 a month and blog income of $500 a month, I can cover about half of my typical monthly expenses of $1,200. Over the course of the next nine months, I expect to be able to cover nearly all of my monthly expenses through these two income streams.

Hypothetically, this means that I could quit my day job and survive just fine without a 9-5 paycheck. If I chose to move overseas, I could live even more cheaply in a place like Thailand. However, there are more factors to consider.

The Family Factor

If I planned on being single forever and living on $15k a year for the rest of my life, I wouldn’t even be facing this dilemma. I could just quit my 9-5 job and work for myself indefinitely without worrying about running out of money.

Unfortunately, there’s no guarantee that my expenses will remain so low. More than likely, I’ll have a wife and kids some day in the future, which could increase my annual expenses closer to $40k or higher. 

My biggest fear is that I don’t save up enough money to live off a combination of passive income and freelance income to support a family and will one day need to go back to 9-5 work. That’s the main reason I am considering saving closer to $200k – $300k before leaving the 9-5 world.

Facing the Unknown

I realize I’m privileged as hell to even be faced with this decision and that it’s not actually a real “problem” at all.

The problem isn’t whether or not I want to work for myself or for a corporation; that decision is obvious. I would much rather work for myself and make a living from blogging and from freelance writing for other sites.

The problem is that I don’t know how much money I need to save to avoid working at a 9-5 ever again. This means that I don’t know long I should stick it out in Corporate America. 

Another concern of mine is that I may dive head first into the “digital nomad” lifestyle and end up liking it less than I anticipated. Would I miss all my loved ones? Would I dislike being my own boss? Would I become unproductive with all of my free time? Would I come to realize that I prefer stability over wanderlust?

The only way I could possibly answer these questions is by actually quitting my job and attempting to work for myself.

There is No User’s Manual for This Situation

There doesn’t exist a user’s manual titled “What To Do Once You Save Up $100k by Age 24, You’re Single, You Want To Be Your Own Boss, You Don’t Know How Expensive a Family Will Be, and You’re Not Sure How Long to Stick It Out in a 9-5 Job”

I might have to write that exact book ten years from now once I see how this situation plays out.

In the meantime, the only way for me to move forward is to follow my “gut, destiny, life, karma, or whatever,” as Steve Jobs said.

My gut is telling me to leave Corporate America in nine months and become my own boss. But that might be too soon. A better idea may be to keep my full time position and continue saving for a few more years.

“Follow Your Passion”

Growing up, I heard time and time again that the way to lead a good life is to simply “follow your passion.”  However, the more I read, the more podcasts I listened to, and the more life experiences I had, the more I realized that this advice is dangerous. 

I have realized that those who quit their day job too soon, without enough savings and without enough aptitude, often fall flat on their face in an attempt to “follow their passion.”

I recognize that it takes time to build up skills, experience, and savings in the bank to truly start working for yourself and to earn an income from your passion. I understand that earning money by working for yourself is considerably harder than most people think.

At the same time, I also realize that the flip side of the coin is equally dangerous. Sticking it out in a comfortable job because you’re scared of working for yourself and of potentially failing can lead to regret. I don’t want to spend too much of my one life on this earth in a 9-5 job that I feel no emotion towards just because I’m too timid to quit and see what else life has to offer.

There’s a fine line between being courageous enough to quit a job and being naive enough to think that you can survive just fine without a paycheck.

The fantasy dream of leaving my job and of becoming a digital nomad sounds great in theory.  But I don’t want to be the person who strikes out on his own too soon and loses all of his money in 3 years, only to come crawling back to Corporate America to find work.

The Paradox of Choice

The fact that I will have choices on how to live my life in the near future is both a blessing and a curse. Up to this point in life, I haven’t actually had to decide what direction to go. I have always had a guide to follow.

From ages 0 to 5, my parents helped me figure out how to live.

From ages 5 to 18, primary and secondary school told me what classes to take and how to spend my time.

From ages 18 to 23, I had a college curriculum to follow. 

For most people, there’s also a guide for adult life: get a starter home, buy a dog, get married, upgrade your car, buy a better home, get more stuff, climb the corporate ladder, and continue on with 9-5 life until you’re old enough to retire.

I, however, have already decided that’s not a path I want to go down. I want to live a life with less stuff and more freedom. It just so happens that this lifestyle choice is rare and that the only way to navigate through it is to figure things out as I go.

Nine months from now, I will have to make some tough decisions. That’s both scary and exciting to think about. 

Once I do figure out my next steps forward, I’ll be sure to blog all about it. Until then, stay tuned…


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.

You can also sign up to have my most recent articles sent straight to your email inbox for free ?

Full Disclosure: Nothing on this site should ever be considered to be advice, research or an invitation to buy or sell any securities, please see my Terms & Conditions page for a full disclaimer.

15 Replies to “I Am 9 Months Away from Making Some Serious Financial Decisions”

  1. Great job on getting to the threshold of $100k. Your willingness to make nontraditional decisions and avoid the “follow your passion” advice so freely handed out is paying off and will continue to do so.

    1. Thanks, Mr. Grumby! I’m not quite there yet but I should be at $100k by the time summer ’18 rolls around. And I’ve always been wary about “follow your passion” advice. I think it has the right idea – to follow your true interests in life – but most people are too quick to chase after some passion without considering the financial costs.

      Thanks for the feedback 🙂

  2. Solid piece and all good questions there Zach. What is your top priority? Quitting ASAP or achieving some specific confidence level that you won’t have to go back to work (is it 80%, 90% or even 99%). This is a risk you are deciding to take and it can be quantified to some extent. The analytical way to approach this would be to break the choice down in to a series of cases and look at your expectancy for each case: (win rate x size of win) – (loss rate x size of loss). You won’t be right in your predictions but at least you know what the distribution of outcomes ‘could’ look like if your assumptions are close to the mark.
    Alternatively, as a mentor once told me: ‘you have no bad options here, your skills are in demand and there will always be opportunities that you can create for yourself. Stop screwing around with over-analyzing this stuff, pick the one that excites you most and froth on!’
    Great problem to have though 😉

    1. Great points, Mr Mofi. And it is a great problem to have vs. many other alternatives.

      Zach – related to Mr Mofi’s point his mentor – you’ll be able to experience various opportunities. With those opportunities, it’s sometimes easier to know what doesn’t make you happy so you know where to focus your time and efforts.

    2. I like that advice from your mentor. I do have a tendency to over-analyze even when all of my options are good options. My top priority is achieving some level of confidence where I don’t think I’ll have to go back to a traditional 9-5 again. The current job I have isn’t stressful or toxic at all, so I’m in a good situation if I do want to stick it out for a while. I just don’t want to get too comfortable and stay in a boring job for longer than I have to. I do like your analytical approach to figuring this situation out. I’ll be sure to give that a try and thanks for the feedback as always 🙂

  3. At your age, I was in a somewhat similar position. I benefitted greatest from a couple of month-to-month leases that let me get out at any time. I loved the places I was living and the people I was living with, but those arrangements made it possible to take a new job in a different state at the drop of a hat, which was a turning point for me. Good luck!

    1. I also like the flexibility of renting just because it gives me options to move around at a moment’s notice. I like the idea of being able to enjoy a place but still always have the option to leave and pursue something else if I feel inclined. Thanks for the kind words 🙂

  4. I definitely feel you on this one, Zach. I’m in a similar situation of being generally bored with a comfortable office job, but it’s hard to give up the solid income and fairly easy life for the big scary unknown. The struggle is real.

    Fortunately, you seem really good about designing a life based on your philosophy and goals; I expect by the time 9 months is up you’ll have arrived at a decision you feel good about.

    1. “It’s hard to give up the solid income and fairly easy life for the big scary unknown.”

      Those are my thoughts exactly. I don’t want to stick around for several more years when I could potentially be fine financially by quitting sooner. I also don’t want to leave too soon when I’m earning good money in a comfy situation. I’ll definitely put plenty of thought into this decision over the coming months. Thanks for the support 🙂

  5. Post-college life can be daunting, as you no longer have that set path in front of you. This is a very thoughtful post about what you’re feeling and the questions you’re trying to answer.

    It sounds like either way you choose you’ll be in good shape. Between blogging/freelance writing/tutoring you could easily make ends meet. What is more important to you in the near future, travel/freedom or a wife and kids? If a wife and kids are your main priority, I’d pick a place to grow your roots and then just utilize vacation days or negotiate a work from home arrangement to give you more flexibility.

    Your expenses will increase substantially with marriage/kids, and I’d say it’s better to save up for a couple more years now than risk having to go back to work further down the line.

    Interested to see how it all plays out for you these next 9 months, and you’re definitely creating a lot of exciting options for yourself by your dedication to savings!

    1. In the immediate future I’m more interested in freedom/travel but I would like to have a family one day when I’m older. I’m trying to find a nice balance between living for now while also being mindful of the future. I agree, I have some good options to choose from either way and I’ll be sure to keep the updates coming on this situation. Thanks for the kind words, Matt!

  6. Right now I feel like you’re being cautious in assessing your options, and by the time next summer rolls around you should be closer to feeling the emotions and excitement of whichever option you really want to do!

    At that point you won’t be wondering what to do, you’ll be figuring out how you can make that dream a reality! Good luck!!!

    1. Thanks for the kind words, Lady Dividend! I’m sure I’ll have a better idea of what I want to do as it gets closer and closer to the time when I have to make a decision. It all depends on what kind of income I’m earning outside of my day job at that point…so we’ll see 🙂

  7. Hi Zach,

    Make hay while it still shines. You have a good paying job with no “push” factor. It is more advisable to work for a few more years and build up your investment portfolio. You can also keep a lookout for potential job opportunities elsewhere.

    Ben

Leave a Reply

Your email address will not be published. Required fields are marked *