How I made a Principled decision to quit my Six Figure job


It has been about a month or so since I quit my Hedge Fund job and jumped right into building consumer facing web-products on my own. Today, the decision to quit feels like a no-brainer. As a matter of fact, I can’t even imagine how I ever put up with a standard 9 to 5 in the first place.

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Nevertheless, for the months leading up to me quitting, and for the time I actually made the decision to quit, absolutely nothing about it was easy. It was incredibly scary, it was hard, totally nerve wrecking. But through it all, I managed to organize my thinking process, and find a way to make a principled decision that carried me through what most would consider the craziest decision of my life. Here’s how I did it.

The old way of making important life decisions

The last few times I had to make decisions about my career, or even my life, the decisions felt easy. Selling the startup I co-founded during college to a company in Silicon Valley felt like a no-brainer; it was an OUT for us from Troy, NY to an amazing place where tech oozed out of every crevice. Later on, leaving a Silicon Valley company to move cross-country (again) and join a hedge fund with the promise of openness, honesty, and a highly lucrative business model seemed like an easy decision too. Similarly, marrying my wife (whom at the time I had dated for only about 8 months) also felt like an easy decision. All of these decisions were easy because the right choice always felt obvious. It was a clear step forward.


But this time around, when even though I should’ve felt like I had ‘made it’ with my six-figure job, cozy office, free lunch, dinner, snacks, awesome parties, an amazing Townhouse (albeit rented), and my 335xi, I still felt unfulfilled. Is this it I wondered? Everything that I had been gunning for since graduation I had achieved. But things still felt empty. When thinking about options available to me within my career, everything felt un-interesting.

You see, in my gut I knew, I knew that what I really wanted was something of my own. Something more cutting edge than Enterprise Products in a Financial Services Firm, and most importantly, something that had the potential to change the world, but that alone wasn’t enough for me to just quit my job and give up everything I had been working toward. I needed more. And even in needing more, there seemed like so many possibilities, that sense of “obvious next step” just wasn’t there. Do I keep working and grow my career? Do I quit and join a startup? Do I apply to YCombinator? Do I bootstrap? Do I do consulting? There were just so many factors, so many possible paths!

Making a principled and conscious life decision

Turth is, for one of the first times in my life, I realized that this was indeed a hard and tough decision. And unlike before, where I would’ve just gone with my gut and hoped for the best (like I always have), I was trying to make a more principled decision. It became apparent exactly how much I had grown as a person over the past few years, especially in the company culture my previous employer instilled — one of self reflection and principled decision making.

For probably the first time in my life, i was trying to make a principled and conscious life decision; instead of just choosing from the options that were obvious and in front of me, I was trying to figure out what I want.

Furthermore, I didn’t want just soft soul-searching, I wanted a raw and hard analytical assessment of what I wanted out of life and how I could go about attaining it.

Most importantly, I know a lot of people struggle through life without really figuring out what really makes them happy, so one of my goals of this exercise was to also extract some sort of repeatable framework out of it.

After a few sessions on the white board, some notes on my moleskine, I felt like I finally came up with a solid framework on how to think through this. Here’s what I ended up with:

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If you squint at the picture, you’ll see the rough process that I followed:

  • I started by answering “What are my values?”
  • Based on my values, I answered “What do I want my life to be about?”
  • I thought hard about what the first two columns meant and elaborated on the things that I thought had the likelihood of being buzz-wordy, undefined, or just plain untrue.

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  • You can’t see this part in the picture, but I then thought through where I am now in my life and reconciled the differences between what I want and where I am today.
  • Finally, I formulated a plan that would allow me to make the changes I need to make to my life to get to what I want in and out of my life.

It was a messy process, but it felt great. It helped me “try on” different things, it helped me realize how life can be a blank slate no matter where you are (if you want it to be), and that a lot of things are possible as long as you have the willingness to dream and the courage to take it on.

I Quit My Job

By following my framework, I realized explicitly that two of the most important things I value are my personal freedom and doing meaningful work. In order to feel fulfilled with my life, I realized that I need to have the freedom to express myself creatively, the freedom to work on things that I find meaningful, and most importantly, the freedom to work on things where I can see direct impact on society.

Although you can argue that I probably knew some of this in my gut, this picture showed me in cold hard details who I wanted to be.

Even worse, it showed me how far off my desired path I had gone. You see, there was also one more thing that was different about having this all written out. It made the difference between reality and what I want all that more clear. Reality was something I could see around me, and for the first time, I was able to compare what I saw around me to some depiction of what I always wanted in my head — essentially my definition of happiness and fulfillment.

And so, with the help of my framework, I discovered that I had to quit my job. It is scary as hell to be quitting a stable job with a great company in the middle of a recession — but whenever I feel that fear, I stare back at my picture. You get one life, about 80 years on Earth, I tell myself… “Why wouldn’t you spend every waking moment making that picture reality?”

I’ve outlined the steps of the framework I used below. Try it out — in my experience, it’s worth knowing whether you are really “all in” to your current life path — whether you truly know what you want out of life.

The Framework

Step 1 — What are my values? I quickly realized that my decision about what to do with my career transcended any concrete goal that I have now. I needed to go back to my core being. I started by answering “Who am I? what are my values?” All constraints, circumstances and situations barred, what’re the things that make me tick?

For me, this took quite some time (the picture shows the finished product). Eventually, I got to a list, neatly ordered in order of importance.

Step 2 — What do I want my life to be about? Armed with a set of values that deeply resonated with my whole being, I then ventured off to answer the question “What do I want?” — more concretely, given my values and the things that are important to me, what do I want to be doing on this planet?

Step 3 — Elaborate on what you want and value During my earlier iterations of this, I realized that society hardwires us to think about values and life purpose a certain way. Because of this, it’s highly likely that if you’re doing this exercise, you’ll end up with a ton of “buzzwords” both in your values and in what you want.

To compensate for this, I spent a good amount of time reflecting on what I wrote. I circled phrases and words that I thought were potential “buzzwords” and elaborated on what I thought they meant — both for my own clarity and also to stress test whether I was truly getting to what I want, or what I think society wants. If you can’t define something you’ve written, clearly it’s not something you truly value or want.

Step 4 — Compare/Contrast between your desired reality and your current So, now that I’ve elaborated and stress tested that I actually want these things, i moved on to compare my desires to my reality.

It’s up to you how much you choose to write down for this step, or how much you want to visualize. For me, it was more about looking at my current reality and visualizing what the reality that I wrote out in my picture would look like and comparing and contrasting between the two.

Step 5 — NOW, devise your plan Now that I’ve got a set of things that I want, a visualization of my current reality and an idea of the difference between the two, I personally felt ready to write out some real goals and plan around achieving them.

I ended up with goals around quitting my job, making sure I start making money independently so I can still pay the bills, and even goals around trimming down expenses for the time that I develop my own business.

What’s next for me

As I said in the beginning of this article, I left my job about a month ago and started my own company to focus full-time on developing my web-based products. For the time being, I’m bootstrapping my business.

I’m excited, I’m jazzed, and I’m also scared shitless. I think the key thing that gives me courage is the fact that I know that I am ALL IN on the path I have chosen.

I’ll write another blog entry reflecting on my first two months as an independent soon. But for those of you are interested, I started Braintrust & Co. a product design firm. I’m actively working on developing and building my three web-based products: Braintrust, Tout and Main Street with a few more ideas in the pipeline. I’m also taking on select clients to help prototype and test out potential web-products of their own.

Are you considering a switch? Did you just take the jump? I’d love to hear from you. Follow me on Twitter or e-mail me.

  • Josh

    You are affirming my coaching process with this post. This is almost the exact process I went through and I take my clients through. The process I use is: 1. Define your ideal life (when they mention an amount of money they want I ask them why until I get to the reason they want the money) 2. Define where you are now compared to each aspect of your ideal life 3. Define an action plan to get from where you are now to your ideal life.

    Josh Bulloc Kansas City, MO How can I help?

  • Tawheed, thanks for sharing. The space between "Oh I could do this or that" and "I am going to to do something specific" is much wider than most give it credit for. Hats off to you for making the leap, I'm sure you'll inspire others to do the same.

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  • Allen

    I agree with the other readers, Tawheed this was a great article and insightful. I did the same thing recently; left a six figure corporate career to do my own thing, and you're right its exciting but quite scary at the same time. Different line of work all together than yours but a similar journey. I wish you all the best and wish you all the success in the world.

    Good luck.

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  • Viki

    Hi nice read. Any chance of a better pic of the whiteboard ? or a pdf version?

  • RawDiamond

    Good luck!

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  • Ahovan

    Hi Tawheed-

    Saw you at NYU the other night re Tout, really liked this blog post.

    I did a similar thing, left a pretty good (financially, not spiritually) career as a litigator to start working at a startup, SourcePad about a year ago. Am not sure I have found something I love, but am very sure that I am on a better path.

    Anyway, see you around.


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  • Cynthia Schames

    You have my utmost admiration! Thanks for walking us through this process; it’s great to have a peek inside the mind of a truly centered, courageous, and -thinking- entrepreneur.

  • If this post seriously doesn’t make you think hard at your own life, nothing else will. Awesome post TK. U sir, are an inspiration. I am at the same spot as you were. 6-figure job, (single though!), everything I had expected when I graduated. But after a few years the initial excitement died down, the world became much more clearer and sense of fulfillment vanished. I have rediscovered my spark by starting to build products on the sidelines though i still have my day IT consultant job. Good luck on ur startup adventures and I hope to join the bandwagon soon! Cheers!

  • your article could help many to take some valuable decision.

  • Thanks for the post TK. I went through a similar “quandary” before heading to the valley. Ultimately, it wasn’t much of a choice and while corporate may offer comfort, passion doesn’t go away. The biggest risk was not to listen…

  • Good luck! ย I did the same thing about 1 year ago. ย After having my two children, I really started to consider what kind of example I was setting for them. ย I mean, if I tell my son that he can do anything, he can find a career that will allow him to be happy, productive and empowered, then I should lead by example.

    It is a scary time but I haven’t looked back yet. I’ve learned so much in the last 10 months and even am working on some community volunteerism to support local high school and middle school teachers to embrace and understand FOSS.

    I’m loving life right now!

  • Anonymous

    Great post indeed which resonates with my current situation…

    I have two questions for you though:

    1) When you say “For me, this took quite some time (the picture shows the finished product)”, how long exactly? Weeks, months, years? 2) Do you have children? ๐Ÿ™‚

    Thanks for the insightful post!

  • I respect you for doing all this just to realize what you want in life. Some of the people I know don’t even bother to read such article as this. They simply wanna grind through their corporate life that they hate, just for the sake of money and safety.

    Hope you the best of luck in your career. ๐Ÿ™‚

  • Guillermo

    What you’ve done is incredibly inspiring. Your purpose has always been to shine and spread this to those around you. If everyone in this world thought and acted as you’ve done, there would be true world peace. What you’ve done is very important on a scale perhaps larger than you can imagine at this point. I wish you all the success–in every aspect…

  • really enjoyed reading your post. Very thought provoking, emotional & nicely written. I understand it was written quite sometime ago. Hope you are successful in the new endevour

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  • Good post, Austin! And congratulations on your marriage as well as your new business!

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  • Kumbho

    Your write-up has really opened doors for getting into some ventures, that had always been there, at the back of my mind. THANKS! All I need to do now is to organize myself….which is tough due to my laid back attitude. ๐Ÿ™‚

  • Good stuff mate. I left my job too, but instead of quitting, I engineered my layoff in order to get a severance and other benefits. I had been there for 11 years and didn’t want to leave so much on the table.

    Financial Samurai

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  • Tiffany Sun

    That’s brilliant! Taking the time to write on a whiteboard on what you really want in life and what you value. And I give you a lot of respect for making the tough decision in leaving a stable job for something more that you want to do. Definitely book-marking this article!

    Thanks for sharing your experience!

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  • happy fathers day

    nice article and good luck Film Dhamaka