How Much Must You Enjoy What You Do For A Living?

Ever head the phrase: “do what you love, and you’ll never work another day in your life”?

I appreciate the sentiment, but find it rather idealistic. The reality is that you’ll never enjoy every single aspect of what you do for a living. Work will always be… work.

I believe that the tribulations that come with a career — stress, tiredness, boredom, feeling overwhelmed — are all part of the process. Experiencing difficulties doesn’t necessarily mean that you’re in the wrong line of work. After all, everything you ever achieve comes at a cost.

It’s down to you to outline your career goals and determine how much you’re willing to sacrifice to achieve them.

The Perfect Job Doesn’t Exist

Even “dream jobs” fail to achieve the optimal balance of hours worked, job satisfaction, and the financial rewards that come with it. Take the following examples:


  • Pros: extremely well paid, fame & adoration, doing the art you enjoy most.
  • Cons: lack of privacy, immense pressure, loss of self (and the need to protect your image), exposure to drugs, fickle friendships, heavy criticisms.


  • Pros: extremely well paid, fame & adoration, good working hours, playing the sport you love.
  • Cons: injuries, always on the road, verbal abuse (including racial), career direction dictated by clubs, short career, unstable income, high rate of depression.


  • Pros: job satisfaction (saving lives), well paid, high social status, well respected by the public.
  • Cons: under appreciated by the state, highly stressful, over-worked, long hours.


  • Pros: well paid, high status, the ability to seek justice.
  • Cons: negative perceptions, long hours, stressful, highly competitive.


  • Pros: highly paid, seen as intelligent.
  • Cons: negatively perceived by the public, long hours, stressful, no tangible product (and perhaps less job satisfaction).

One of the main reasons I started writing this blog to begin with is that I felt that there was a need to present online business for what it really is: a huge challenge. The idyllic picture-perfect lifestyle that we so often see perpetuated on social media isn’t representative of the effort and sacrifice invested to achieve online success.

In my opinion, the best you can realistically expect is an idealjob, which aligns with all of your key values — regardless whether that’s at a company or in self-employment.

Put simply: not everything you do in your job will be fun.

What Do You Value?

Money earned, hours worked, distance to your place work, social status, human interaction, and stress levels experienced are just some of the common factors that make up one’s ideal job. But importantly, what do you value the most?

If, for example, you value hours worked above anything else, and wish to have more free time and holidays, then that’s likely to reduce your income. Are you happy to take the pay cut?

If you value recognition, power, prestige — then that’s likely to come with additional responsibilities. Are you up for the challenge? Can you handle more stress and extra commitment?

This all sounds obvious. But it’s surprisingly easy to lose sight of what you really want from your career. What might start out as a pursuit of a pay rise can spiral into a life of all work and no play; more money, but no time to enjoy it; perceived ‘success’, but internalising feelings of pressure and stress.

My Values

Personally I’ve always treated holiday time as mandatory; I don’t allow work to eat into travel.

I also value income enough to make sacrifices. I admit, there’s been periods where I’ve taken on more work than I could realistically manage, missed social gatherings, and neglected my free time, all for the chance to earn more money. It was far from ideal, but I did it because I have the following view:

Money cannot buy happiness. But it can buy stability, experiences, freedom, and opportunities. These things contribute to my level of happiness.

I still have this view. But in recent years I’ve made a conscious effort to invest more of my energy into improving my job itself — increasing efficiency, maximising productivity, unblocking bottlenecks — rather than purely chasing the money. In other words, I’m trying to earn as much money as possible with the least amount of time and stress involved.

How Close To Perfection Can An Online Business Become?

A huge advantage of running your own online business is having the ability to control your own destiny. After all, there’s a lot less interference — such as difficult bosses & colleagues, long commutes, and corporate decisions impacting your livelihood. So if you know what you value in a job, and accept the inevitable challenges along the way, you can work towards creating it.

Freedom — My Biggest Challenge Yet

I’ve tried to create my perfect job for over decade. It’s not easy.

One weaknesses I’ve had to overcome was the lack of “safety net”, and therefore very little freedom:

  • My business wasn’t very diverse, so I was heavily reliant on one income stream.
  • I didn’t have permanent employees or colleagues to back me up if I wasn’t physically at the desktop.
  • Many business tasks required constant attention, making it difficult to expand into new avenues.

So the power of being ‘free’ by running my own business didn’t happen on it’s own. Adaptation was required to achieve a much greater level of freedom.

The Need To Compromise

I’ve come to learn that even while running my own business, I simply can’t have everything my way. That’s not how it works.

I can’t spend all of my time doing only what I love; writing only about subjects I find interesting, developing only products that I like using, avoiding those “boring” marketing or admin tasks. To afford what I want, and have the free time I want, I have to look beyond what’s ‘fun’ to me.

While I always try to steer my businesses into fields I take a keen interest in (e.g. sports, football, analytics, developing interesting products) I can’t entirely dictate what the market wants, and what brings in the money. I have to do certain things that I don’t deem to be fun, for the greater good (in my case, more security). This has a positive impact on my life.

I take the approach of compromise:

  • Passion: I’m passionate about achieving happiness, but I accept that the vehicle can come in different forms to what I imagined.
  • Outsourcing: I outsource those tasks that make me miserable, but accept that it’s a business expense with limitations, and that I need to take on some of those tasks myself.
  • Automation: I know that times will get tough, but I try to reduce stress through automation and “streamlining”.
  • Passivity: I focus as much effort as possible on projects that can grow without requiring constant input. For example: affiliate marketing (along with evergreen content), and Amazon FBA as opposed to freelancing. This frees up time without loss of income.

While job perfection is impossible, I accept that to get anywhere close to it, I need to take the rough with the smooth. Rather than “never working another day in my life” I believe in another cliché: “everything worth having is worth fighting for”.

5 thoughts on “How Much Must You Enjoy What You Do For A Living?

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