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Should I Quit My Job?

Background:

The past three years or so I’ve talked myself out of quitting my job four times, managed two episodes of burnout, been in constant battle with the Resistance while taming a growing pressure to replace my main stream of income with “diversifed income streams”.

This is my latest attempt at clarifying my thoughts (i.e. overthinking) around in what ways am I still unhappy, what I want, and where I can go from here.

I have many scattered journal entries similar to this, but this time I decided to just share it. Perhaps it resonate and can help you think through your own situation.

It features rants about the hype of lifestyle business, personal branding, optionality, abundance of opportunities, being eaten alive by the thought of opportunity cost, and other patronising common sensical advices.

I’m not completely happy with the way it flows right now — strung together in a semi rambling stream of consciousness, but I want to learn to live with good enough. I plan to eventually revisit and edit this word vomit with a clear takeaways and conclusion once I let it cook a bit in the back of my mind. I’d like to 1) kill lots of darlings here, 2) rearrange and turn this into a more coherent and logically sound pieces, and 3) add more concrete personal stories to illustrate the points better.

Pardon the slight preachy tone. This is me talking to myself, really.

“I want to quit my job and do what I love”

Unclear thinking leads to hazardous decisions and lack of progress while clear thinking helps alleviate more pain than we expect.

In what ways is that sentence unclear? Let’s unpack.

Do you mean:

  • Quit this job // why? then what "job" would be a better option?
  • Quit all jobs and become self employed // what will you employ yourself for?
  • Quit working, take a break, and live off your savings for a while because you’re burned out // what exhausted you? how can you prevent it in the future?
  • Find a less demanding job that pays less. I’ll live off the grid grow my own plants and make money when I really need it, whatever. // sure, go do it. what's stopping you?
  • Save enough money, quit the rat race, then live the simple life // do you have any number for what is enough?
  • Build a company, make a nice exit, then retire early // you'll likely be miserable building a business for the sake of exiting it. if you love the thrill and the process of building and running a business then you'll be back in 6 months time with another venture. so don't BS yourself.
  • Quit and do whatever I want to. answer to no one. rebel against the capitalism and society. see through the invisible script. stop being a cog in the machine! // you'll always escape one game and step into another one.
  • I just want to able to spend more time doing my hobby. Getting a mini retirement trial run.
  • Quit your 9-5 and make money online. This guru says I can make money off the internet just travelling the world or selling stuff from China on Amazon? // but first "buy this ebook", "enroll in that course"?

Let’s start from the last point.

This idea of “escape the 9-5, stop building someone else’s empire and start building your empire” has always been fashionable. Selling the entrepreneurship dream. Do what you love. Find (and monetise!) your passion.

Oh the pressure and imprecise thinking in that whole idea!

As with many of you do, I am wary of people making money teaching other people how to “live your dream life doing what you love”. It’s a pitch. A pitch means we get presented a narrow slice of filtered view, in a certain frame, with the goal of winning you(r r) over. We reality framed in a certain way, with the goal of winning you(r resources, in this case: money) over.

We know one when we see one.

If I had to break it down, a couple of good heuristic to spot a pitch is to look at what it’s being sold and promised. If it’s too good to be true, then it most likely is. If it promised 100% guaranteed results, it’s likely snake oil salesmanship. If we’re only being presented the positives, the highlights and the glamorous aspects, and none of the unappealing drudgery as we often do ourselves when we share things in public, then take it with a grain of salt. There is no shortcut, no secret to “success” however we define it.

Don’t get me wrong, alternative ways of earning an income do exist. Traditional employment model is becoming less and less mandatory. It’s very likely that you’ll be able to find a way to make a decent (or even better) living doing things that are closer to your interests with less unnecessary stress than whatever you’re doing now. The future of work is here for us to embrace and define. Making money is not hard. What’s hard is making money in a way that aligns with what we imagine it should look like.

And if you define your dream life as “a life that aligns better with my values where I have the power and resource to set up a structure to keep me moving towards each meaningful goal in a sustainable and fulfilling way” then there are genuine products and services out there that will help you clarify your own decisions, and there is merit in investing your time, money, energy for some of the valuable insights and experience to guide you along your journey.

But I do get a bit worried whenever I see remarks along the lines of “I have finally quit my job and started my own YouTube channel wooo!”. I wonder how they’re doing now. There are many many things more interesting, more profitable, with much more earning potential than starting a YouTube channel or setting up your own online shop.

I think many would agree that becoming a full-time content creator with large social media following is one of the most overrated and overhyped approach to make money these days. It quickly became one of the widely adopted definition of “doing what you love”. It makes sense. Vanity metrics are easy to measure and provde instant gratification.

If you think you have a good understanding of how the attention / eyeball economy work — what are the constraints and risks; what drives it, and what it entails, then by all means go for it. They are all valid options. But just like entrepreneurship, it’s not for everyone. Many people are happier as an employee and many people squirm at the thought of self promotion.

The number of opportunities that open up with the technological advances, social infrastructure, and a vast abundant supply of audience and problems you can solve is beyond one’s comprehension — arguably to the point of paralysis for those who has yet developed a sense of who they are, who they are not, and is convinced that they can “do anything as long as they work hard for it”.

The more you learn about how the world works and what makes human tick, the more you see the different sub-universes containing infinite opportunities out there for you to take or create. There is a market for ANYTHING. The idea of 1000 true fans is real.

The sneaky paradox here is: knowing that these options exist makes you more unhappy about your life choices and situations than you should be. The idea that there is an alternate future where you could be earning at least double your current income while living in some tropical island if you decided to pursue it but there is no could be paralysing. // which btw, for me living in a tropical country, the dream is to go live in a cabin in a lake in Ontario or near mountains of Colorado. The grass is always greener folks....

Having an ideal means that you’re noticing all the ways your present is not ideal. You’re defining your now by all the things it’s not. It’s rooted in scarcity. You are focused on all the ways it’s lacking.

==You likely are thinking too small right now==. I remember back in 2013 I got a job offer that paid 70% more what I was making at that point. My baseline was so low and what I thought was possible was so limited that it never crossed my mind such opportunity exist — or that I deserve more. And to my surprise in the same month I got another offer for 100% the amount I was making, which I declined for the first offer as it is more aligned with where I wanted my career to go.

But once my mind opened up to that possibility, I can never go back. I keep expanding the horizon and the courage to entertain and explore the higher levels. If you told me that in 7 years I’d be stuck somewhat unhappy and resentful to only be earning 7x, I’ll call you crazy but you’d be amazed how small you are thinking right now. It is such a cliche but again and again I have observed that my world is really limited to what I dare to think of.

There will always be a better option out there. There is always a better view down the line. Don’t spend all your time and camera storage snapping all the pictures at this current viewpoint.

But it’s a challenge to manage that state and not being eaten alive by the thought of opportunity cost.

Ignorance is bliss and constraints are liberating.

The idea of quitting is enticing. There’s a big quick emotional payoff waiting for us if we were to pull the trigger. We daydream of that moment we gather up the courage, handed over our resignation letter, an implicit “eff this, I’m done“.

Starting something from scratch is exciting. Moving into a new city, starting fresh, no baggage, clean slate, reset the mess.

It’s dramatic, romantic, and epic.

Most people love intensity more than they can stand consistency. Easy sexy fixes and destinations over the boring process of showing up and building towards the new. We don’t have much patience these days, reinforced by the illusion and highlights we bombarded ourselves with on a daily basis.

But I think the hastiness, impulsiveness, and impatience that fuel these decision is not much different from the mindless uninformed decisions we made years ago when we were starting our career. We don’t know what the career will bring, so we just try. And that’s probably the right approach anyway, once we decide what “right” means for ourselves.

Again such a cliche, but life is what you make of it. It’s the story you tell yourself. And we’re so good at telling all sorts of stories to ourselves, so we can’t go wrong really.

Going back to the original statement: What exactly does “do what you love” mean to you?

Escaping from and escaping to is very different. Do you have a pull or do you only have a push?

I would guess most of us have push; things you’d like to escape from.

You could be in a job that:

  • is boring / not challenging anymore
  • is stressful, where you feel lack impact or control
  • is not a fit with your skills and interests
  • has toxic environment
  • you managed to use and drive yourself to burnout

But there’s some amount of pull keeping you from making the jump:

  • things are not perfect but the trade-offs are tolerable
  • there is hope of things improving
  • comfort zone, mediocre certainty
  • you got a chip on your shoulder, still something to prove
  • let me have the final bite of the carrot
  • complex dependencies and external considerations involving spouse and children

And not many people have strong enough external pull to snap them off the inertia. We don’t know what we’d like to escape to.

Well we might have an idea, but they either:
– is impractical // how so? have you done any calculation or tried to define how exactly is it impractical?
– is not socially acceptable // I find that this becomes less of a factor as you age.

When you have family to feed, your situation is seemingly more complicated. But on the flip side, I consider this as one of the best situations to be in. Constraints are liberating. And parenthood provides you with the privilege of dedicating your life for a bigger purpose than your own.

Different situation requires different way out. Identify clearly and plan accordingly.

I have a cousin who feels stuck in a dead end job she’s been in for 13 years. We talked it through, came up with some concrete sensible options. But she never got around to taking the actions or following through. Making big decisions are hard. Everything is so entangled, many unknowns and considerations.

Often a dream will always be a dream, and that’s fine. That’s probably the purpose — live your life right now and have a “point B” to aspire to. It keeps you going.

You’re not doing anything wrong or yourself any disservice if you’re not chasing your dream ASAP, RIGHT. NOW. You’re doing the best with what you think you have, within what you think is possible.

So: Are you doing your best? What do you think you have? What do you think is possible?

Chances are you are restless because you are not clear on some or all three.

Now, it’s worth making the distinction between a hobby, a job, a career, and a vocation.

Which ones do you deal with in your life right now? How would you classify your different activities? Are they in the right places? Are you mixing any of them up? Do you have the right expectations for each of them?

No job, career, even vocation is perfect. There will always be some drudgery that comes with it. Even writers have to do taxes.

I call it “for later but never”. Khe calls it the “when-then trap”.

How many times have you arrived, hit your goal, and almost immediately launch upon the next thing?

How many “once I x then I’ll be happy”, “once I x then I can finally y” have you sifted through?

How many times have you thought “yes, this is it, after this I have proved I’ve made it” but apparently the goal comes with a sense of emptiness and their own baggage and messy circumstances?

If this struck a chord, I suggest you read about “arrival fallacy” and the mythology of Sisyphus.

The majority of us are in this state of being mildly dissatisfied, a little complacent, and slightly numb. Yes it’d be awesome if everyone could pursue their dreams, fulfill all our potentials, and get “there” RIGHT NOW. But it’s okay to not have 100% of your life highly optimised and maximised for “greatness”. It’s OK to only have fun on the weekends, travel 1-2 weeks a year, go through the mundane day to day, enjoy the occasional novelty, checking out the newest hyped food spot in your city, hanging out with your boring friends. It’s OK to work a boring corporate job with daily commute. It’s OK to be mediocre.

If you don’t like it then change it. You understand your situation and privilege best. You know how much power and potential you have. You know what fear and constraints you’re adopting. You can find out what frame you’re operating within. You know you and only you can get you unstuck.

If you don’t like it then change it, one by one. You get clear on the things and put one foot in front of the other.

Feeling guilty over these is OK but being manipulated into guilt by the “should and coulds” is not. Acknowledge and drop the guilt, then start working.

If you don’t know what you want, leaving what you don’t want will likely not lead you directly to things you want.

Leaving what you don’t want will lead you to things you want only if you keep track and learn from the “mistake”.

Now you say, how do you figure out what you want if you don’t have time and energy to think about it or try things out?

I’ve come to believe that: if you really want it, you will make time.

And an even more important point: know that it will take time. I’ve made the mistake of thinking I can figure everything out in one or two weekends. It’s not going to happen. And I’ve come to accept that you just can’t rush some things.

And to be precise, you’ll never “figure things out” because it’s not a state. It’s a process. You’ll just keep on “buffering” the next path to take.

Perhaps we know what we want but afraid to even admit it and be honest to ourselves. Perhaps we are not sure that it is a socially acceptable choice. But hey, what’s the worst thing that could happen?

I think where many people are also stuck at is with managing this expectation — frustrated they haven’t had the “aha moment”. As really, it’s not a single moment. It’s many many small moments that compounded.

So start asking yourself lots and lots of questions to clarify your own thoughts. Start holding those questions, get serious in seeking answers, and things will start getting clearer.

If I could summarise my thoughts so far:

  1. Develop self-awareness. Get honest with yourself. Ask what do you want, who do you want to be — instead of what you should or could want.
  2. Have the courage to ask. Two parts to this: First ask for permission to yourself to deserve, have, and pursue what you want. And then ask others for help to get what you want. Don’t mix the two.
  3. Be serious in seeking the answers. Feel free to keep switching the question until you can be serious with the quest. Don’t expect perfection. Iteration, not destination.
  4. Accept and own your current choices. What if you’re happy with what you have? Define what “enough” means to you.
  5. Learn how the world works. Notice the abundance of options, then ignore deliberately and aggressively.
  6. Manage your expectations. Know it’s a neverending journey. It takes time and you’ll never “arrive”. But start now.

So what to do concretely?

  1. Be clear on what you can and can’t live without. What you need for survival and what your real priorities are. Basic needs, minimum monthly income, emergency fund, emotional support, living situations.
  2. Do some thinking, confront your fears, lay out your assumptions, manage the risks, think it through, have a plan, pull the trigger, and own all the trade-offs. Know that whatever decision you make now you’ll be able to reverse, bounce back. That this is just one decision. It’s not going to be forever; it’s not permanent. Just keep learning and orienting yourself to navigate the adventure.

After thoughts

  1. If so many people are unhappy with their jobs then can we think about the problem from another angle: how can we help set up the structure around modern work life to allow more people to be able to enjoy and find fulfillment in their work? I have rambled above on how this could be done as an inside job but there must also be some ideas involving the way we structure education and employment — both are complex systems with entrenched history that require multiple attack points to unravel that I am not going to attempt to articulate here.
  2. If you go out “doing your own thing” before deciding on who you’re interested in helping and what problem you’re helping these people with, you’ll likely to fail. If you just make choices based on what you like, what you want, what you are good at, soon enough you’ll cave into the growing societal pressure and confusion and go back looking for employment. It is hard work to figure out which tree you’re here to help plant, who you’ll be able to invite to sit under the shade, and convice to reward you accordingly. Yes you start with what you have but you have to do it for someone.

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Also published on Medium.

Published by tre

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